WO2018048042A1 - Antiseptic and antibacterial composition for external application, containing glycerin lactic acid ester as active ingredient - Google Patents

Antiseptic and antibacterial composition for external application, containing glycerin lactic acid ester as active ingredient Download PDF

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Publication number
WO2018048042A1
WO2018048042A1 PCT/KR2017/001620 KR2017001620W WO2018048042A1 WO 2018048042 A1 WO2018048042 A1 WO 2018048042A1 KR 2017001620 W KR2017001620 W KR 2017001620W WO 2018048042 A1 WO2018048042 A1 WO 2018048042A1
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composition
antiseptic
lactic acid
antimicrobial
acid ester
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PCT/KR2017/001620
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French (fr)
Korean (ko)
Inventor
배대호
이고은
Original Assignee
주식회사 가나씨앤에이치
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Publication of WO2018048042A1 publication Critical patent/WO2018048042A1/en

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
    • A01N31/02—Acyclic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/045—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates
    • A61K31/047—Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates having two or more hydroxy groups, e.g. sorbitol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/34—Alcohols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Definitions

  • the present invention relates to a topical composition for antiseptic and antibacterial, comprising glycerin lactic acid ester as an active ingredient.
  • the cosmetic composition is mainly composed of oil or water, and glycerin, sugars, amino acids, proteins, etc., which are nutrients of microorganisms, are often blended therein.
  • glycerin, sugars, amino acids, proteins, etc. which are nutrients of microorganisms, are often blended therein.
  • water since the water itself is a basic ingredient for the growth and proliferation of microorganisms, all substances using water have a fundamental inherent potential for contamination by microorganisms.
  • household goods composition generally refers to dishwashing detergent, wet tissue, mask, sheet, feminine cleaning agent, mouthwash, toothpaste, etc.
  • these products also microbial contamination during manufacturing, microorganism contamination or use of the skin surface by skin contact during use Heavy water pollution may occur.
  • the possibility of contamination by microorganisms is inherent by water used in the manufacture of these products.
  • compositions usually contain preservatives for the purpose of suppressing the growth of microorganisms and making them aseptic as they are completely killed over time.
  • preservatives such as parabens such as paraoxybenzoic acid esters, and preservatives such as imidazolidinyl urea, phenoxy ethanol, and isothiazoline series are used.
  • composition prepared without using these preservatives is also possible, but in that case, there is a significant reduction in aseptic manufacturing or shelf life, a change in physical properties, and an inherent resistance to microbial contamination by external factors. It is believed to have many drawbacks.
  • the diol-based antiseptic function composition has been used in recent years, but the problem of the skin irritation and in particular the problem of lowering the viscosity of the cosmetic composition has a limit of the amount of use.
  • the problem of its use is limited due to problems such as miscibility.
  • the miscibility to water is inferior, and only a limited application of emulsifiers is used.
  • antiseptic or antimicrobial components used in external preparations such as cosmetics used directly on the human body should exhibit sufficient antiseptic and antimicrobial effects against various strains even with a small amount of use, and do not affect the active ingredients used together. It is particularly important to be able to use them in a variety of formulations without compromising, and also not to compromise the properties of the external preparation such as viscosity, color.
  • the present inventors have tried to develop an antiseptic and antimicrobial external preparation composition having such characteristics, in particular, an antiseptic and antimicrobial external composition having excellent compatibility while retaining antimicrobial activity against various formulations.
  • this invention was completed by developing the antiseptic and antimicrobial external preparation composition excellent in miscibility, showing the outstanding antiseptic activity independently, without mix
  • an object of the present invention is to provide an antiseptic and antimicrobial external preparation composition containing glycerin lactic acid ester as an active ingredient and having excellent antimicrobial activity and excellent miscibility.
  • the present invention provides a topical composition for antiseptic and antibacterial comprising a glycerin lactic acid ester compound represented by the following formula (1) as an active ingredient.
  • the external preparation composition is antiseptic against microorganisms selected from the group consisting of Escherichia, Pseudomonas, Staphylococcus, Candida and Aspergillus. It exhibits antimicrobial activity.
  • the topical composition is particularly Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Candida albicans and Aspergillus niger. It shows excellent antiseptic and antimicrobial activity against microorganisms selected from the group consisting of:
  • the external preparation composition is characterized in that it has a formulation of water (water type), oil in water (oil in water type) or water in oil type (water in oil type).
  • the compound of Formula 1 contains 0.1 to 10.0% (w / w) based on the total weight of the external preparation composition.
  • the external composition is characterized in that the pharmaceutical composition, cosmetic composition or household composition.
  • the external composition comprising a glycerin lactic acid ester as an active ingredient provides a broad antimicrobial spectrum and miscibility.
  • the external preparation composition of the present invention exhibits excellent antimicrobial activity even at low concentrations as compared with conventional preservatives.
  • a technical feature of the present invention is to provide an external preparation composition which maintains antiseptic function and has excellent miscibility without using preservatives or diols which are display designated ingredients.
  • the term “preservative” refers to an activity of increasing the shelf life by preventing the decay or alteration caused by the growth of microorganisms.
  • antibacterial refers to an activity that inhibits or kills the growth of microorganisms.
  • Glycerin lactic acid ester which is an active ingredient of the external preparation composition of the present invention, is prepared by esterifying a glycerin with lactic acid.
  • Glycerin is mainly used as a moisturizer in cosmetics, and is often used in food and favorite food groups.
  • the molecular formula of glycerin is C 3 H 8 O 3
  • the structural formula is shown in the formula (2) below.
  • Lactic acid is widely used as a major and secondary ingredient in foods, medicines, and various organic compounds, and in recent years, the demand for biodegradable and bioactive polymers has increased.
  • the production of lactic acid uses a microbial fermentation or chemical synthesis method, and most of the total production is currently proceeding with a microbial fermentation method.
  • the main raw material for lactic acid production by the microbial fermentation method is glucose from lactose or starch.
  • the molecular formula of lactic acid is C 3 H 6 O 3
  • the structural formula is shown in the formula (3) below.
  • glycol lactic acid ester refers to 2-hydroxy-2,3-dihydroxypropyl ester.
  • 2-hydroxy-2,3-dihydroxypropyl ester of the formula (1) is 1 to 2 mol of glycerin and lactic acid, respectively: It is prepared by inducing an esterification reaction by mixing in a ratio of 1 mol and acid catalyst treatment.
  • glycerin and lactic acid are mixed in a 1: 1 to 2: 1 molar ratio, respectively, and an acid catalyst or salt thereof corresponding to 0.1 to 1 part by weight of the weight of lactic acid, which is an organic acid, for example, PTSA (Para Toluene Sulfonic Acid). ), Hydrochloric acid, sulfuric acid, phosphoric acid, hypophosphorous acid, sodium hypophosphite, and the like are added and mixed properly.
  • the mixed raw materials are dehydrated at 120-200 ° C. for 5-10 hours under nitrogen conditions.
  • the remaining glycerin and lactic acid are removed by distillation under reduced pressure.
  • the ester of the present invention is prepared by filtration of glycerine lactic acid ester from which unreacted material is removed to remove foreign substances.
  • One of the main features of the present invention is the antimicrobial activity against microorganisms.
  • pharmaceuticals, quasi-drugs, cosmetics, and the like there is a possibility that the contaminated microorganisms multiply. Microbial contamination can degrade the formulation and adversely affect the health of the consumer. Manufacturers should therefore suppress microbial contamination of raw materials, containers, packaging and end products as low as possible to ensure the quality, safety and efficacy of the preparation.
  • the external preparation composition of the present invention provides effective antimicrobial activity at a lower concentration than conventional preservative compounds.
  • the antimicrobial and antiseptic external preparation composition of the present invention may be of the genus Escherichia, Pseudomonas, Staphylococcus, Candida, and Aspergillus. (Aspergillus) exhibits antimicrobial activity against microorganisms selected from the group consisting of.
  • composition of the present invention is Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Candida albicans and Aspergillus. It exhibits better antimicrobial activity against microorganisms selected from the group consisting of Aspergillus niger.
  • the glycerin lactic acid ester compound of Formula 1 contains 0.1 to 10.0% (w / w) based on the total weight of the external preparation composition.
  • the active ingredient of the present invention 2-hydroxy-2,3-dihydroxypropyl ester (2-hydroxy-2,3-dihydroxypropyl ester) dissolution activity for various formulations It has a point.
  • the external preparation composition may be prepared in various formulations of water type, oil in water type or water in oil type.
  • the external preparation composition of the present invention maintains excellent antiseptic and antimicrobial activity even when prepared in water, oil-in-water and water-in-oil type preparations, and does not affect the stability of the formulation and thus shows excellent miscibility.
  • the glycerin lactic acid ester of the present invention has many differences and advantages from glycerin fatty acid esters, typically glycerin caprylic acid ester, which are frequently used in conventional preservative formulations.
  • Glycerin fatty acid ester series such as glycerin caprylic acid ester, in external preparations, especially in cosmetic compositions, are esters of glycerin as an aqueous composition and fatty acids as an oil-based composition as an emulsifier. These materials are emulsifiers or surfactants having inherent Hydrophilic-Lipophilic Balance (HLB) values, and when they are not compatible with the HLB of the cosmetic composition, cases of destabilizing the emulsification state of the cosmetics occur.
  • HLB Hydrophilic-Lipophilic Balance
  • the viscosity drop of about 10 to 20% occurs as in the viscosity measurement value in the following test example.
  • the glycerin lactic acid ester of the present invention is an ester of lactic acid, which is an aqueous composition similar to glycerin, an aqueous composition, and thus does not affect HLB in external preparations, especially cosmetic compositions, because HLB does not exist as other glycerin fatty acid esters. It does not occur if it inhibits.
  • composition of the present invention is applied as an external application (external application), in the present specification, the term “external agent” refers to a formulation for delivering the desired material to the body by applying to the external use of the human body, such as skin, oral cavity.
  • the external preparation composition of the present invention may be prepared as a cosmetic composition.
  • the glycerin lactic acid ester of Formula 1 may be used in place of cosmetic preservatives because it prevents the cosmetic composition from being altered by bacteria.
  • the composition of the present invention may include the components commonly used in cosmetic compositions, as well as glycerin lactic acid esters, their solvates or hydrates thereof, such as antioxidants. , Conventional adjuvants such as stabilizers, solubilizers, vitamins, pigments and flavorings, and carriers.
  • the topical composition of the present invention may be prepared in any formulation conventionally prepared in the art, for example, solutions, suspensions, emulsions, pastes, gels, creams, lotions, powders, soaps, surfactant-containing cleansing , Oils, powders, foundations, emulsion foundations, wax foundations and sprays and the like can be formulated, but is not limited thereto. More specifically, it may be prepared in the form of a flexible lotion, nutrition lotion, nutrition cream, massage cream, essence, eye cream, cleansing cream, cleansing foam, cleansing water, pack, spray or powder.
  • the formulation of the present invention is a paste, cream or gel, animal oils, vegetable oils, waxes, paraffins, starches, trachants, cellulose derivatives, polyethylene glycols, silicones, bentonites, silicas, talc or zinc oxide may be used as carrier components.
  • animal oils, vegetable oils, waxes, paraffins, starches, trachants, cellulose derivatives, polyethylene glycols, silicones, bentonites, silicas, talc or zinc oxide may be used as carrier components.
  • animal oils vegetable oils, waxes, paraffins, starches, trachants, cellulose derivatives, polyethylene glycols, silicones, bentonites, silicas, talc or zinc oxide
  • cellulose derivatives polyethylene glycols
  • silicones bentonites
  • silicas talc or zinc oxide
  • lactose, talc, silica, aluminum hydroxide, calcium silicate or polyamide powder may be used, in particular in the case of a spray, additionally chlorofluorohydrocarbon, propane Propellant such as butane or dimethyl ether.
  • a solvent, solubilizer or emulsifier is used as the carrier component, such as water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1 Fatty acid esters of, 3-butylglycol oil, glycerol aliphatic ester, polyethylene glycol or sorbitan.
  • liquid carrier diluents such as water, ethanol or propylene glycol
  • suspending agents such as ethoxylated isostearyl alcohol, polyoxyethylene sorbitol ester and polyoxyethylene sorbitan ester, microcrystals Soluble cellulose, aluminum metahydroxy, bentonite, agar or tracant and the like can be used.
  • the carrier component is aliphatic alcohol sulfate, aliphatic alcohol ether sulfate, sulfosuccinic acid monoester, isethionate, imidazolinium derivative, methyltaurate, sarcosinate, fatty acid amide.
  • Ether sulfates, alkylamidobetaines, aliphatic alcohols, fatty acid glycerides, fatty acid diethanolamides, vegetable oils, lanolin derivatives or ethoxylated glycerol fatty acid esters and the like can be used.
  • the components included in the external preparation composition for skin of the present invention include components conventionally used in the external preparation composition for skin, in addition to the active ingredient and the carrier component, for example, such as antioxidants, stabilizers, solubilizers, vitamins, pigments and perfumes. Phosphorus adjuvant.
  • the external composition of the present invention having broad antimicrobial, antiseptic spectrum and miscibility can be widely used to achieve the purpose of antimicrobial, sterilization, disinfection, antiseptic, etc. in medicinal products, cosmetics, household goods, as well as quasi-drugs and pesticides. have.
  • 2-hydroxy-2,3-dihydroxypropyl ester was prepared by esterification under an acid catalyst of glycerin and lactic acid.
  • glycerin 99.9%, Aekyung emulsification
  • lactic acid 95%, large purified gold
  • PTSA acid catalyst
  • the crude ester after the reaction was removed by distillation under reduced pressure of the remaining glycerin and lactic acid.
  • the unreacted glycerol lactic acid ester was filtered through diatomaceous earth to remove foreign substances to prepare 2-hydroxy-2,3-dihydroxypropyl ester.
  • Example 1 An aqueous composition containing the glycerin lactic acid ester prepared in Example 1 was prepared according to the composition of Table 1 in a conventional manner.
  • the antiseptic force in the aqueous composition of the glycerin lactic acid ester prepared in Example 1 was evaluated.
  • An antiseptic test was conducted using a glycerin caprylic acid ester-containing aqueous composition having a preservative activity (Comparative Example 1) and an aqueous composition containing a representative antiseptic composition 1,2-hexanediol (Comparative Example 2). .
  • the type of strain used and the number of initial bacteria (unit: CFU / ml) are as follows.
  • Example 2 Comparative Example 1 and Comparative Example 2 were each divided into 20 strains and mixed with five strains. Colonies were counted on day 7, 14, 21 and 28 and 10-fold serial dilution.
  • the dilution ratio in the above table indicates the contents of diluting the sample of each compound in 1/10 (volume ratio) units with sterile 0.85% NaCl saline to facilitate the measurement of the number of bacteria after one unit of culture. Since it is difficult to accurately count thousands or tens of thousands of colonies in culture media with a diameter of 90 mm, the colonies are diluted in units of 1/10, 1/100, and 1/1000, and the colonies are 10 to 300 CFU /. Cultured in ml and counted.
  • glycerin caprylic acid esters were found to be incompatible with water and precipitated in an oily or solid phase, and their use in aqueous compositions was extremely limited.
  • composition of the 0 / W formulation containing the glycerin lactic acid ester prepared in Example 1 was prepared in a conventional manner according to the composition of Table 5.
  • the antiseptic power of the O / W formulation composition of the glycerin lactic acid ester prepared in Example 3 was evaluated.
  • Antiseptic force against glycerine caprylic acid ester-containing O / W composition (Comparative Example 3) having antiseptic activity and O / W composition (Comparative Example 4) containing 1,2-hexanediol as a representative antiseptic composition The test was conducted.
  • Example 3 Comparative Examples 3 and 4 the antiseptic test was conducted in the same manner as in Test Example 1.
  • the type of strain used and the number of initial bacteria (unit: CFU / ml) are as follows.
  • Example 3 The lotion of the O / W formulation of Example 3 containing the glycerin lactic acid ester of the present invention as an active ingredient was compared to the lotion of Comparative Example 3 containing the glycerin caprylic acid ester and the comparative example 4 containing 1,2-hexanediol. Better antiseptic activity was shown. In addition, Comparative Examples 3 and 4 showed a disadvantage that the viscosity of the lotion formulation is low (Table 5).
  • the BB cream of the W / O formulation containing the glycerin lactic acid ester prepared in Example 1 was prepared in a conventional manner according to the composition of Table 9 below.
  • the antiseptic power of the W / O formulation composition of the glycerin lactic acid ester prepared in Example 4 was evaluated.
  • Example 4 Comparative Examples 5 and 6, the antiseptic test was conducted in the same manner as in Test Example 1.
  • the type of strain used and the number of initial bacteria (unit: CFU / ml) are as follows.
  • Aspergillus niger (ATSC No.16404) 2.2 ⁇ 10 5
  • the composition of the W / O formulation of Example 4 containing the present invention glycerin lactic acid ester as an active ingredient contains Comparative Example 5, 1,2-hexanediol containing glycerin caprylic acid ester It showed more excellent antiseptic activity compared to Comparative Example 6.
  • the glycerol lactic acid ester-containing BB cream of Example 4 compared to the BB cream without preservative prescription was maintained a constant viscosity, it was confirmed that the viscosity of the other two preservatives drops sharply.
  • the external preparation composition containing 2-hydroxy-2,3-dihydroxypropyl ester of the present invention as an active ingredient may be prepared in water, oil-in-water and water-in-oil type preparations. Even when prepared, excellent antiseptic and antimicrobial activity is maintained, and especially, it does not affect the stability of the formulation, and shows excellent miscibility.
  • the external preparation composition of the present invention having a wide range of antimicrobial, antiseptic spectrum and miscibility can be widely used to achieve the purpose of antibacterial, sterilization, disinfection, antiseptic, etc. in medicinal products, cosmetics, household goods as well as quasi-drugs, pesticides and the like.

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Abstract

The present invention relates to an antiseptic and antimicrobial composition for external application, containing glycerin lactic acid ester as an active ingredient. As an active ingredient, the glycerin lactic acid ester of the present invention provides a broad antimicrobial spectrum and miscibility and exhibits excellent antiseptic and antimicrobial activity even at a concentration lower than that of conventional antiseptic agents.

Description

글리세린 젖산 에스테르를 유효성분으로 하는 방부 및 항균용 외용제 조성물Antiseptic and antibacterial external preparation composition containing glycerin lactic acid ester as an active ingredient
본 발명은 글리세린 젖산 에스테르를 유효성분으로 하는 방부 및 항균용 외용제 조성물에 관한 것이다.The present invention relates to a topical composition for antiseptic and antibacterial, comprising glycerin lactic acid ester as an active ingredient.
일반적으로 화장료 조성물은 기름이나 물을 주성분으로 하며 거기에 미생물의 영양성분이 되는 글리세린, 당 계열, 아미노산계, 단백질 등이 배합되는 경우가 대부분이다. 또한 사용하는 물 자체가 미생물의 생장 및 증식에 기본이 되는 성분이므로 물을 사용하는 모든 물질은 미생물에의 오염 가능성을 기본적으로 내재하고 있다 볼 수 있다.In general, the cosmetic composition is mainly composed of oil or water, and glycerin, sugars, amino acids, proteins, etc., which are nutrients of microorganisms, are often blended therein. In addition, since the water itself is a basic ingredient for the growth and proliferation of microorganisms, all substances using water have a fundamental inherent potential for contamination by microorganisms.
또한 생활용품 조성물은 일반적으로 주방세제, 물티슈, 마스크, 시트, 여성청결제, 구강세정제, 치약 등을 말하는 것으로 이들 제품도 제조 중의 미생물 오염, 사용 중의 피부접촉에 의한 피부 표면의 미생물에 의한 오염 또는 사용 중 물에 의한 오염이 발생할 수 있다. 또한 이들 제품을 제조하는 과정에서 사용되는 물에 의해 기본적으로 미생물에 의한 오염 가능성이 내재되어 있음을 알 수 있다.In addition, household goods composition generally refers to dishwashing detergent, wet tissue, mask, sheet, feminine cleaning agent, mouthwash, toothpaste, etc., these products also microbial contamination during manufacturing, microorganism contamination or use of the skin surface by skin contact during use Heavy water pollution may occur. In addition, it can be seen that the possibility of contamination by microorganisms is inherent by water used in the manufacture of these products.
이에 이들 조성물은 통상 미생물의 증식을 억제하고 보존 시간의 경과에 따라 이들 미생물을 완전히 사멸하여 무균상태로 만들어 제품의 보존성을 향상시키는 것을 목적으로 방부제가 함유되어 있다. 이러한 방부제로서 파라옥시안식향산에스테르와 같은 파라벤류의 방부제나 이미다졸리디닐우레아, 페녹시 에탄올, 이소치아졸린계열 등의 방부제가 사용된다.Therefore, these compositions usually contain preservatives for the purpose of suppressing the growth of microorganisms and making them aseptic as they are completely killed over time. As such preservatives, preservatives such as parabens such as paraoxybenzoic acid esters, and preservatives such as imidazolidinyl urea, phenoxy ethanol, and isothiazoline series are used.
물론 이들 방부제를 사용하지 않고 제조되는 조성물도 가능하지만, 그럴 경우, 무균제조나 유통기한의 대폭적인 감소, 물성의 변화, 또한 외부에 의한 미생물 오염불안의 내재성이 있기 때문에 경제적 문제점 및 실용적인 부분에서 많은 단점을 가지고 있다 여겨진다.Of course, a composition prepared without using these preservatives is also possible, but in that case, there is a significant reduction in aseptic manufacturing or shelf life, a change in physical properties, and an inherent resistance to microbial contamination by external factors. It is believed to have many drawbacks.
또한 일부 디올 계열의 방부 기능 조성물이 근래 사용되어지고 있으나 피부 자극성의 문제와 특히 화장료 조성물의 점도를 떨어뜨리는 문제점을 내재하고 있어 사용량의 제한을 두고 있는 실정이다. 또한 더불어 혼화성 등의 문제로 그 사용 용도가 한정되어 있는 문제도 가지고 있다. 특히 물에의 혼화성이 떨어지는 경우가 많아 유화제 사용 경우 등의 한정적인 적용만 되고 있다.In addition, some of the diol-based antiseptic function composition has been used in recent years, but the problem of the skin irritation and in particular the problem of lowering the viscosity of the cosmetic composition has a limit of the amount of use. In addition, there is a problem that its use is limited due to problems such as miscibility. In particular, the miscibility to water is inferior, and only a limited application of emulsifiers is used.
그러므로 인체에 직접적으로 사용되는 화장품과 같은 외용제에 사용되는 방부 내지 항균용 성분은 적은 양의 사용으로도 다양한 균주에 대하여 충분한 방부 및 항균 효과를 나타내어야 하며, 함께 사용되어지는 활성성분에 영향을 주지 않으면서 다양한 종류의 제형에 사용 가능하여야 하고, 또한, 점도, 색상과 같은 외용제 제형의 특성을 해하지 않는 것이 특히 중요하다.Therefore, antiseptic or antimicrobial components used in external preparations such as cosmetics used directly on the human body should exhibit sufficient antiseptic and antimicrobial effects against various strains even with a small amount of use, and do not affect the active ingredients used together. It is particularly important to be able to use them in a variety of formulations without compromising, and also not to compromise the properties of the external preparation such as viscosity, color.
본 발명자들은 이러한 특성을 가지는 방부 및 항균용 외용제 조성물, 특히 다양한 제형에 대하여 항균력을 보유하면서 우수한 혼화성을 갖는 방부 및 항균용 외용제 조성물을 개발하고자 노력하였다. 그 결과, 화학방부제나 디올류를 배합하지 않고 단독으로 우수한 방부 활성을 나타내면서 혼화성이 뛰어난 방부 및 항균용 외용제 조성물을 개발함으로써, 본 발명을 완성하였다.The present inventors have tried to develop an antiseptic and antimicrobial external preparation composition having such characteristics, in particular, an antiseptic and antimicrobial external composition having excellent compatibility while retaining antimicrobial activity against various formulations. As a result, this invention was completed by developing the antiseptic and antimicrobial external preparation composition excellent in miscibility, showing the outstanding antiseptic activity independently, without mix | blending a chemical preservative or diols.
따라서, 본 발명은 글리세린 젖산 에스테르를 유효성분으로 함유하여 항균력이 우수하며 혼화성이 뛰어난 방부 및 항균용 외용제 조성물을 제공하는 것을 목적으로 한다.Therefore, an object of the present invention is to provide an antiseptic and antimicrobial external preparation composition containing glycerin lactic acid ester as an active ingredient and having excellent antimicrobial activity and excellent miscibility.
상기 목적을 달성하기 위하여 본 발명에 따르면, 본 발명은 하기 화학식 1로 표시되는 글리세린 젖산 에스테르 화합물을 유효성분으로 포함하는 방부 및 항균용 외용제 조성물이 제공된다.According to the present invention in order to achieve the above object, the present invention provides a topical composition for antiseptic and antibacterial comprising a glycerin lactic acid ester compound represented by the following formula (1) as an active ingredient.
[화학식 1][Formula 1]
Figure PCTKR2017001620-appb-I000001
Figure PCTKR2017001620-appb-I000001
상기 외용제 조성물은 이스케리치아(Escherichia) 속, 슈도모나스(Pseudomonas) 속, 스태필로코커스(Staphylococcus) 속, 칸디다(Candida) 속 및 아스퍼질러스(Aspergillus) 속으로 구성된 군으로부터 선택되는 미생물에 대하여 방부, 항균 활성을 나타낸다.The external preparation composition is antiseptic against microorganisms selected from the group consisting of Escherichia, Pseudomonas, Staphylococcus, Candida and Aspergillus. It exhibits antimicrobial activity.
상기 외용제 조성물은 특히 이스케리치아 콜리(Escherichia coli), 슈도모나스 애루지노사(Pseudomonas aeruginosa), 스태필로코커스 아우레우스(Staphylococcus aureus), 칸디다 알비칸스(Candida albicans) 및 아스퍼질러스 니거(Aspergillus niger)로 구성된 군으로부터 선택되는 미생물에 대하여 우수한 방부, 항균 활성을 나타낸다.The topical composition is particularly Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Candida albicans and Aspergillus niger. It shows excellent antiseptic and antimicrobial activity against microorganisms selected from the group consisting of:
상기 외용제 조성물은 수형(water type), 수중유형(oil in water type) 또는 유중수형(water in oil type)의 제형을 가지는 것임을 특징으로 한다.The external preparation composition is characterized in that it has a formulation of water (water type), oil in water (oil in water type) or water in oil type (water in oil type).
상기 화학식 1 화합물은 외용제 조성물 총중량에 대하여 0.1~10.0%(w/w) 함유된다. 상기 외용제 조성물은 약학 조성물, 화장료 조성물 또는 생활용품 조성물인 것을 특징으로 한다.The compound of Formula 1 contains 0.1 to 10.0% (w / w) based on the total weight of the external preparation composition. The external composition is characterized in that the pharmaceutical composition, cosmetic composition or household composition.
본 발명, 글리세린 젖산 에스테르를 유효성분으로 포함하는 외용제 조성물은 넓은 항균 스펙트럼 및 혼화성을 제공한다. 또한 본 발명 외용제 조성물은 종래의 방부제와 비교하여 낮은 농도에서도 우수한 항균 활성을 나타낸다.The present invention, the external composition comprising a glycerin lactic acid ester as an active ingredient provides a broad antimicrobial spectrum and miscibility. In addition, the external preparation composition of the present invention exhibits excellent antimicrobial activity even at low concentrations as compared with conventional preservatives.
이하, 본 발명을 더욱 상세하게 설명한다.Hereinafter, the present invention will be described in more detail.
본 발명은 표시지정성분인 방부제나 디올류를 사용하지 않고서도 방부 기능이 유지되며, 동시에 혼화성도 우수한 외용제 조성물을 제공하는 것을 기술적 특징으로 한다.A technical feature of the present invention is to provide an external preparation composition which maintains antiseptic function and has excellent miscibility without using preservatives or diols which are display designated ingredients.
특히 화장료 조성물 및 생활용품 조성물에 파라벤류, 이미다졸리디닐우레아, 페녹시 에탄올, 이소치아졸린계의 방부제나 디올류를 배합하지 않고도, 방부력이 우수하면서 사용성 및 안정성도 우수한 외용제 조성물을 제공하고자 한다.In particular, to provide an external preparation composition having excellent antiseptic properties and excellent usability and stability without blending parabens, imidazolidinyl urea, phenoxy ethanol, and isothiazoline-based preservatives or diols in cosmetic compositions and household compositions. do.
본 명세서에서 용어 "방부"는 미생물의 증식에 의한 부패나 변질을 방지하여 저장기간을 늘리는 활성을 의미한다. 본 명세서에서 용어 "항균"은 미생물의 성장을 저지하거나 사멸시키는 활성을 의미한다.As used herein, the term "preservative" refers to an activity of increasing the shelf life by preventing the decay or alteration caused by the growth of microorganisms. As used herein, the term "antibacterial" refers to an activity that inhibits or kills the growth of microorganisms.
본 발명 외용제 조성물의 유효성분인 글리세린 젖산 에스테르는 글리세린과 젖산을 에스테르화 반응시켜 제조한다.Glycerin lactic acid ester, which is an active ingredient of the external preparation composition of the present invention, is prepared by esterifying a glycerin with lactic acid.
글리세린은 화장품에서 보습제로 주로 사용되고 있으며 식품 및 기호식품군 등에 자주 사용되고 있다. 글리세린의 분자식은 C3H8O3로서 그 구조식은 아래 화학식 2와 같다.Glycerin is mainly used as a moisturizer in cosmetics, and is often used in food and favorite food groups. The molecular formula of glycerin is C 3 H 8 O 3 The structural formula is shown in the formula (2) below.
[화학식 2][Formula 2]
Figure PCTKR2017001620-appb-I000002
Figure PCTKR2017001620-appb-I000002
젖산(lactic acid)은 식품, 의약품 및 각종 유기화합물의 주, 부원료로 광범위하게 사용되고 있으며, 특히 최근에는 생분해성 및 생체활성고분자 등의 원료로 그 수요의 증대가 이루어지고 있다. 젖산의 제조는 미생물발효 혹은 화학적 합성방법을 사용하고 있으며, 현재 전체 생산의 대부분을 미생물발효방법으로 진행하고 있다. 미생물 발효방법에 의한 젖산 생산의 주 원료는 락토스(Lactose) 혹은 전분 유래의 글루코스(Glucose) 이다. 젖산의 분자식은 C3H6O3로 그 구조식은 아래 화학식 3과 같다.Lactic acid is widely used as a major and secondary ingredient in foods, medicines, and various organic compounds, and in recent years, the demand for biodegradable and bioactive polymers has increased. The production of lactic acid uses a microbial fermentation or chemical synthesis method, and most of the total production is currently proceeding with a microbial fermentation method. The main raw material for lactic acid production by the microbial fermentation method is glucose from lactose or starch. The molecular formula of lactic acid is C 3 H 6 O 3 The structural formula is shown in the formula (3) below.
[화학식 3][Formula 3]
Figure PCTKR2017001620-appb-I000003
Figure PCTKR2017001620-appb-I000003
본 명세서에서 용어 "글리세린 젖산 에스테르"는 2-하이드록시-2,3-다이하이드록시프로필 에스테르(2-hydroxy-2,3-dihydroxypropyl ester)를 나타낸다.As used herein, the term "glycerine lactic acid ester" refers to 2-hydroxy-2,3-dihydroxypropyl ester.
본 발명의 일 구체예에 따르면, 하기 화학식 1의 2-하이드록시-2,3-다이하이드록시프로필 에스테르(2-hydroxy-2,3-dihydroxypropyl ester)는 글리세린 및 젖산을 각각 1~2몰:1몰의 비율로 혼합하고 산촉매 처리하여 에스테르화 반응을 유도하여 제조한다.According to one embodiment of the invention, 2-hydroxy-2,3-dihydroxypropyl ester of the formula (1) is 1 to 2 mol of glycerin and lactic acid, respectively: It is prepared by inducing an esterification reaction by mixing in a ratio of 1 mol and acid catalyst treatment.
[화학식 1][Formula 1]
Figure PCTKR2017001620-appb-I000004
Figure PCTKR2017001620-appb-I000004
보다 구체적으로는 글리세린과 젖산을 각각 1:1 몰비 내지는 2:1 몰비로 혼합하고, 유기산인 젖산 중량의 0.1~1중량부에 해당하는 산촉매 또는 그 염, 예를 들면, PTSA(Para Toluene Sulfonic Acid), 염산, 황산, 인산, 차아인산, 차아인산나트륨 등의 촉매를 투입하여 적절히 혼합한다. 혼합된 원료들을 질소조건하에 120~200℃에서 5~10시간 탈수반응을 진행한다. 남아있는 글리세린과 젖산을 감압증류하여 제거한다. 미반응물이 제거된 글리세린 젖산 에스테르를 규조토에 여과하여 이물질을 제거함으로써, 본 발명의 에스테르를 제조한다.More specifically, glycerin and lactic acid are mixed in a 1: 1 to 2: 1 molar ratio, respectively, and an acid catalyst or salt thereof corresponding to 0.1 to 1 part by weight of the weight of lactic acid, which is an organic acid, for example, PTSA (Para Toluene Sulfonic Acid). ), Hydrochloric acid, sulfuric acid, phosphoric acid, hypophosphorous acid, sodium hypophosphite, and the like are added and mixed properly. The mixed raw materials are dehydrated at 120-200 ° C. for 5-10 hours under nitrogen conditions. The remaining glycerin and lactic acid are removed by distillation under reduced pressure. The ester of the present invention is prepared by filtration of glycerine lactic acid ester from which unreacted material is removed to remove foreign substances.
본 발명의 주요한 특징 중 하나는 미생물에 대한 항균활성이다. 일반적으로 의약품, 의약외품, 화장품 등의 제제는 오염된 미생물이 증식할 가능성이 있다. 미생물 오염은 제제의 품질을 떨어뜨리고 소비자의 건강에 나쁜 영향을 미칠 수 있다. 그러므로 제조자는 제제의 품질, 안전성, 유효성을 확보하기 위하여 원료, 용기, 포장 및 최종제품의 미생물 오염을 최대한 낮게 억제해야 한다.One of the main features of the present invention is the antimicrobial activity against microorganisms. In general, pharmaceuticals, quasi-drugs, cosmetics, and the like, there is a possibility that the contaminated microorganisms multiply. Microbial contamination can degrade the formulation and adversely affect the health of the consumer. Manufacturers should therefore suppress microbial contamination of raw materials, containers, packaging and end products as low as possible to ensure the quality, safety and efficacy of the preparation.
본 발명의 외용제 조성물은 기존의 방부제 화합물보다 적은 농도에서 유효한 항균 활성을 제공한다.The external preparation composition of the present invention provides effective antimicrobial activity at a lower concentration than conventional preservative compounds.
본 발명의 일 구현예에 따르면, 본 발명의 항균 및 방부용 외용제 조성물은 이스케리치아(Escherichia) 속, 슈도모나스(Pseudomonas) 속, 스태필로코커스(Staphylococcus) 속, 칸디다(Candida) 속 및 아스퍼질러스(Aspergillus) 속으로 구성된 군으로부터 선택되는 미생물에 대하여 항균 활성을 나타낸다.According to one embodiment of the present invention, the antimicrobial and antiseptic external preparation composition of the present invention may be of the genus Escherichia, Pseudomonas, Staphylococcus, Candida, and Aspergillus. (Aspergillus) exhibits antimicrobial activity against microorganisms selected from the group consisting of.
더욱 구체적으로는, 본 발명의 조성물은 이스케리치아 콜리(Escherichia coli), 슈도모나스 애루지노사(Pseudomonas aeruginosa), 스태필로코커스 아우레우스(Staphylococcus aureus), 칸디다 알비칸스(Candida albicans) 및 아스퍼질러스 니거(Aspergillus niger)로 구성된 군으로부터 선택되는 미생물에 대하여 더욱 우수한 항균 활성을 나타낸다.More specifically, the composition of the present invention is Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Candida albicans and Aspergillus. It exhibits better antimicrobial activity against microorganisms selected from the group consisting of Aspergillus niger.
상기 화학식 1의 글리세린 젖산 에스테르 화합물은 외용제 조성물 총중량에 대하여 0.1~10.0%(w/w) 함유된다. The glycerin lactic acid ester compound of Formula 1 contains 0.1 to 10.0% (w / w) based on the total weight of the external preparation composition.
본 발명의 주요한 특징 중 다른 하나는, 본 발명의 활성성분인 상기 2-하이드록시-2,3-다이하이드록시프로필 에스테르(2-hydroxy-2,3-dihydroxypropyl ester)는 다양한 제형에 대하여 용해 활성을 갖는 점이다.Another one of the main features of the present invention, the active ingredient of the present invention 2-hydroxy-2,3-dihydroxypropyl ester (2-hydroxy-2,3-dihydroxypropyl ester) dissolution activity for various formulations It has a point.
본 발명의 일 구현예에 따르면, 상기 외용제 조성물은 수형(water type), 수중유형(oil in water type) 또는 유중수형(water in oil type)의 다양한 제형으로 제조될 수 있다.According to an embodiment of the present invention, the external preparation composition may be prepared in various formulations of water type, oil in water type or water in oil type.
하기 시험예에서 입증되는 바와 같이, 본 발명의 외용제 조성물은 수형, 수중유형 및 유중수형 제제로 제조되는 경우에도 우수한 방부, 항균활성이 유지되며 제형의 안정성에 영향을 주지 않아 우수한 혼화성을 나타낸다.As demonstrated in the following test examples, the external preparation composition of the present invention maintains excellent antiseptic and antimicrobial activity even when prepared in water, oil-in-water and water-in-oil type preparations, and does not affect the stability of the formulation and thus shows excellent miscibility.
본 발명의 글리세린 젖산 에스테르는 기존의 방부 처방으로 자주 사용되는 글리세린 지방산 에스테르, 대표적으로 글리세린 카프릴릭산 에스테르와 많은 차이와 장점이 있다. 외용제, 특히 화장료 조성물에 있어서 글리세린 카프릴릭산 에스테르와 같은 글리세린 지방산 에스테르 계열은 일종의 유화제로서 수계 조성물인 글리세린과 유계 조성물인 지방산의 에스테르이다. 이러한 물질은 고유의 HLB(Hydrophilic-Lipophilic Balance)값을 가지는 유화제 내지는 계면활성제로서 화장료 조성물의 HLB와 적합하지 않은 경우, 화장료의 유화상태를 불안정하게 만드는 사례가 발생한다. 그러다 보니 하기의 시험예에서의 점도 측정값과 같이 10~20% 가량의 점도 저하 현상이 발생하게 된다. 하지만 본 발명의 글리세린 젖산 에스테르는 수계 조성물인 글리세린과 마찬가지의 수계 조성물인 젖산의 에스테르로서 다른 글리세린 지방산 에스테르와 같은 HLB가 존재하지 않기 때문에 외용제, 특히 화장료 조성물에서의 HLB에 영향을 미치지 않아 물성의 안정성을 저해하는 경우가 발생하지 않는다. 마찬가지 수계 조성물인 1, 2-헥산디올의 경우에는 디올류 특유의 점도 저하 현상이 존재하는데 본 발명의 글리세린 젖산 에스테르는 그러한 디올류와도 달라 안정성을 저해하지 않는다.The glycerin lactic acid ester of the present invention has many differences and advantages from glycerin fatty acid esters, typically glycerin caprylic acid ester, which are frequently used in conventional preservative formulations. Glycerin fatty acid ester series, such as glycerin caprylic acid ester, in external preparations, especially in cosmetic compositions, are esters of glycerin as an aqueous composition and fatty acids as an oil-based composition as an emulsifier. These materials are emulsifiers or surfactants having inherent Hydrophilic-Lipophilic Balance (HLB) values, and when they are not compatible with the HLB of the cosmetic composition, cases of destabilizing the emulsification state of the cosmetics occur. As a result, the viscosity drop of about 10 to 20% occurs as in the viscosity measurement value in the following test example. However, the glycerin lactic acid ester of the present invention is an ester of lactic acid, which is an aqueous composition similar to glycerin, an aqueous composition, and thus does not affect HLB in external preparations, especially cosmetic compositions, because HLB does not exist as other glycerin fatty acid esters. It does not occur if it inhibits. Similarly, in the case of 1, 2-hexanediol, which is a water-based composition, there is a viscosity drop phenomenon peculiar to diols, but the glycerin lactic acid ester of the present invention does not impair stability unlike such diols.
본 발명의 조성물은 외용제(external application)로 적용되며, 본 명세서에서, 용어 "외용제"는 피부, 구강 등 인체 외용에 적용하여 체내로 목적하는 물질을 전달하기 위한 제제를 의미한다.The composition of the present invention is applied as an external application (external application), in the present specification, the term "external agent" refers to a formulation for delivering the desired material to the body by applying to the external use of the human body, such as skin, oral cavity.
본 발명의 외용제 조성물은 화장료 조성물로 제조될 수 있다. 본 발명의 조성물이 화장료 조성물로 제조될 경우, 화학식 1의 글리세린 젖산 에스테르는 세균에 의해 화장료 조성물이 변질되는 것을 예방하므로 화장품 방부제를 대체하여 사용될 수 있다. 본 발명의 조성물이 화장료 조성물로 제조되는 경우, 본 발명의 조성물은 상기 유효성분인 글리세린 젖산 에스테르, 그들의 용매화물 또는 수화물뿐만 아니라, 화장료 조성물에 통상적으로 이용되는 성분들을 포함할 수 있으며, 예컨대 항산화제, 안정화제, 용해화제, 비타민, 안료 및 향료와 같은 통상적인 보조제, 그리고 담체를 포함할 수 있다.The external preparation composition of the present invention may be prepared as a cosmetic composition. When the composition of the present invention is made of a cosmetic composition, the glycerin lactic acid ester of Formula 1 may be used in place of cosmetic preservatives because it prevents the cosmetic composition from being altered by bacteria. When the composition of the present invention is made of a cosmetic composition, the composition of the present invention may include the components commonly used in cosmetic compositions, as well as glycerin lactic acid esters, their solvates or hydrates thereof, such as antioxidants. , Conventional adjuvants such as stabilizers, solubilizers, vitamins, pigments and flavorings, and carriers.
본 발명의 외용제 조성물은 당 업계에서 통상적으로 제조되는 어떠한 제형으로도 제조될 수 있으며, 예를 들어, 용액, 현탁액, 유탁액, 페이스트, 겔, 크림, 로션, 파우더, 비누, 계면활성제-함유 클렌징, 오일, 분말, 파운데이션, 유탁액 파운데이션, 왁스 파운데이션 및 스프레이 등으로 제형화될 수 있으나, 이에 한정되는 것은 아니다. 보다 상세하게는, 유연 화장수, 영양 화장수, 영양 크림, 마사지 크림, 에센스, 아이 크림, 클렌징 크림, 클렌징 포옴, 클렌징 워터, 팩, 스프레이 또는 파우더의 제형으로 제조될 수 있다.The topical composition of the present invention may be prepared in any formulation conventionally prepared in the art, for example, solutions, suspensions, emulsions, pastes, gels, creams, lotions, powders, soaps, surfactant-containing cleansing , Oils, powders, foundations, emulsion foundations, wax foundations and sprays and the like can be formulated, but is not limited thereto. More specifically, it may be prepared in the form of a flexible lotion, nutrition lotion, nutrition cream, massage cream, essence, eye cream, cleansing cream, cleansing foam, cleansing water, pack, spray or powder.
본 발명의 제형이 페이스트, 크림 또는 겔인 경우에는 담체 성분으로서 동물성유, 식물성유, 왁스, 파라핀, 전분, 트라칸트, 셀룰로오스 유도체, 폴리에틸렌 글리콜, 실리콘, 벤토나이트, 실리카, 탈크 또는 산화아연 등이 이용될 수 있다.When the formulation of the present invention is a paste, cream or gel, animal oils, vegetable oils, waxes, paraffins, starches, trachants, cellulose derivatives, polyethylene glycols, silicones, bentonites, silicas, talc or zinc oxide may be used as carrier components. Can be.
본 발명의 제형이 파우더 또는 스프레이인 경우에는 담체 성분으로서 락토스, 탈크, 실리카, 알루미늄 히드록시드, 칼슘 실리케이트 또는 폴리아미드 파우더가 이용될 수 있고, 특히 스프레이인 경우에는 추가적으로 클로로플루오로히드로카본, 프로판/부탄 또는 디메틸 에테르와 같은 추진체를 포함할 수 있다.When the formulation of the present invention is a powder or a spray, lactose, talc, silica, aluminum hydroxide, calcium silicate or polyamide powder may be used, in particular in the case of a spray, additionally chlorofluorohydrocarbon, propane Propellant such as butane or dimethyl ether.
본 발명의 제형이 용액 또는 유탁액인 경우에는 담체 성분으로서 용매, 용해화제 또는 유탁화제가 이용되고, 예컨대 물, 에탄올, 이소프로판올, 에틸 카보네이트, 에틸 아세테이트, 벤질 알코올, 벤질 벤조에이트, 프로필렌글리콜, 1,3-부틸글리콜 오일, 글리세롤 지방족 에스테르, 폴리에틸렌 글리콜 또는 소르비탄의 지방산 에스테르가 있다.When the formulation of the present invention is a solution or emulsion, a solvent, solubilizer or emulsifier is used as the carrier component, such as water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, propylene glycol, 1 Fatty acid esters of, 3-butylglycol oil, glycerol aliphatic ester, polyethylene glycol or sorbitan.
본 발명의 제형이 현탁액인 경우에는 담체 성분으로서 물, 에탄올 또는 프로필렌 글리콜과 같은 액상의 희석제, 에톡실화 이소스테아릴 알코올, 폴리옥시에틸렌 소르비톨 에스테르 및 폴리옥시에틸렌 소르비탄 에스테르와 같은 현탁제, 미소결정성 셀룰로오스, 알루미늄 메타히드록시드, 벤토나이트, 아가 또는 트라칸트 등이 이용될 수 있다.When the formulation of the present invention is a suspension, liquid carrier diluents such as water, ethanol or propylene glycol, suspending agents such as ethoxylated isostearyl alcohol, polyoxyethylene sorbitol ester and polyoxyethylene sorbitan ester, microcrystals Soluble cellulose, aluminum metahydroxy, bentonite, agar or tracant and the like can be used.
본 발명의 제형이 계면-활성제 함유 클렌징인 경우에는 담체 성분으로서 지방족 알코올 설페이트, 지방족 알코올 에테르 설페이트, 설포숙신산 모노에스테르, 이세티오네이트, 이미다졸리늄 유도체, 메틸타우레이트, 사르코시네이트, 지방산 아미드 에테르 설페이트, 알킬아미도베타인, 지방족 알코올, 지방산 글리세리드, 지방산 디에탄올아미드, 식물성 유, 라놀린 유도체 또는 에톡실화 글리세롤 지방산 에스테르 등이 이용될 수 있다.When the formulation of the present invention is a surfactant-containing cleansing, the carrier component is aliphatic alcohol sulfate, aliphatic alcohol ether sulfate, sulfosuccinic acid monoester, isethionate, imidazolinium derivative, methyltaurate, sarcosinate, fatty acid amide. Ether sulfates, alkylamidobetaines, aliphatic alcohols, fatty acid glycerides, fatty acid diethanolamides, vegetable oils, lanolin derivatives or ethoxylated glycerol fatty acid esters and the like can be used.
본 발명의 피부 외용제 조성물에 포함되는 성분은 상기 유효 성분 및 담체 성분 이외에, 피부 외용제 조성물에 통상적으로 이용되는 성분들을 포함하며, 예컨대 항산화제, 안정화제, 용해화제, 비타민, 안료 및 향료와 같은 통상적인 보조제를 포함할 수 있다.The components included in the external preparation composition for skin of the present invention include components conventionally used in the external preparation composition for skin, in addition to the active ingredient and the carrier component, for example, such as antioxidants, stabilizers, solubilizers, vitamins, pigments and perfumes. Phosphorus adjuvant.
상기한 바와 같이 광범위한 항균, 방부 스펙트럼　및 혼화성을 갖는 본 발명의 외용제 조성물은 의약, 화장품, 생활용품 뿐 아니라 의약외품, 농약 등에서 항균, 살균, 소독, 방부 등의 목적을 달성하기 위해 광범위하게 사용될 수 있다.As described above, the external composition of the present invention having broad antimicrobial, antiseptic spectrum and miscibility can be widely used to achieve the purpose of antimicrobial, sterilization, disinfection, antiseptic, etc. in medicinal products, cosmetics, household goods, as well as quasi-drugs and pesticides. have.
이하, 실시예를 통하여 본 발명을 더욱 상세히 설명하고자 한다. 이들 실시예는 오로지 본 발명을 보다 구체적으로 설명하기 위한 것으로, 본 발명의 요지에 따라 본 발명의 범위가 이들 실시예에 의해 제한되지 않는다는 것은 당 업계에서 통상의 지식을 가진 자에게 있어서 자명할 것이다.Hereinafter, the present invention will be described in more detail with reference to Examples. These examples are only for illustrating the present invention in more detail, it will be apparent to those skilled in the art that the scope of the present invention is not limited by these examples in accordance with the gist of the present invention. .
실시예 1: 글리세린 젖산 에스테르의 제조Example 1 Preparation of Glycerin Lactic Acid Ester
글리세린과 젖산의 산촉매 하에서 에스테르화 반응을 통해 2-하이드록시-2,3-다이하이드록시프로필 에스테르(2-hydroxy-2,3-dihydroxypropyl ester)를 제조하였다.2-hydroxy-2,3-dihydroxypropyl ester was prepared by esterification under an acid catalyst of glycerin and lactic acid.
먼저 글리세린(99.9%, 애경유화)과 젖산(95%, 대정화금)을 각각 1~2:1 몰비로 혼합하고, 유기산인 젖산 중량의 0.1~1중량부에 해당하는 산촉매(PTSA)를 투입하여 혼합하였다. 혼합된 원료들을 질소조건하에 120~200℃에서 5~10시간 탈수반응을 진행하였다. 에스테르 반응을 통해 생성되는 물은 냉각콘덴서를 통해 분리하고 반응을 유지하였다.First, glycerin (99.9%, Aekyung emulsification) and lactic acid (95%, large purified gold) are mixed at a molar ratio of 1 to 2: 1, respectively, and an acid catalyst (PTSA) corresponding to 0.1 to 1 parts by weight of lactic acid, which is an organic acid, is added. And mixed. The mixed raw materials were dehydrated at 120-200 ° C. for 5-10 hours under nitrogen conditions. Water produced through the ester reaction was separated through a cooling capacitor and maintained the reaction.
반응이 종료된 조에스테르는 남아있는 글리세린과 젖산을 감압증류하여 제거하였다. 미반응물이 제거된 글리세린 젖산 에스테르를 규조토에 여과하여 이물질을 제거하여 2-하이드록시-2,3-다이하이드록시프로필 에스테르(2-hydroxy-2,3-dihydroxypropyl ester)를 제조하였다.The crude ester after the reaction was removed by distillation under reduced pressure of the remaining glycerin and lactic acid. The unreacted glycerol lactic acid ester was filtered through diatomaceous earth to remove foreign substances to prepare 2-hydroxy-2,3-dihydroxypropyl ester.
실시예 2: 수계 조성물 제조Example 2: Preparation of Aqueous Composition
상기 실시예 1에서 제조된 글리세린 젖산 에스테르를 함유하는 수계조성물을 하기 표 1의 조성에 따라 통상의 방법으로 제조하였다.An aqueous composition containing the glycerin lactic acid ester prepared in Example 1 was prepared according to the composition of Table 1 in a conventional manner.
시험예 1: 방부력 평가Test Example 1: Evaluation of Antiseptic Force
상기 실시예 1에서 제조된 글리세린 젖산 에스테르의 수계조성물에서의 방부력을 평가하였다. 방부 활성을 가지고 있는 글리세린 카프릴릭산 에스테르 함유 수계조성물(비교예 1) 및 대표적인 방부조성물인 1,2-헥산디올을 함유하는 수계조성물(비교예 2)을 비교 대상으로 하여 방부력 시험을 진행하였다.The antiseptic force in the aqueous composition of the glycerin lactic acid ester prepared in Example 1 was evaluated. An antiseptic test was conducted using a glycerin caprylic acid ester-containing aqueous composition having a preservative activity (Comparative Example 1) and an aqueous composition containing a representative antiseptic composition 1,2-hexanediol (Comparative Example 2). .
Figure PCTKR2017001620-appb-T000001
Figure PCTKR2017001620-appb-T000001
사용된 균주의 종류 및 초기 균수(단위; CFU/㎖)는 다음과 같다.The type of strain used and the number of initial bacteria (unit: CFU / ml) are as follows.
이스케리치아 콜리(Escherichia coli ATCC No.8739) 2.0×106 Escherichia coli ATCC No.8739 2.0 × 10 6
슈도모나스 애루지노사(Pseudomonas aeruginosa ATCC No.10145) 5.0×106 Pseudomonas aeruginosa ATCC No.10145 5.0 × 10 6
스태필로코커스 아우레우스(Staphylococcus aureus ATCC No.6538) 1.6×106 Staphylococcus aureus ATCC No.6538 1.6 × 10 6
칸디다 알비칸스(Candida albicans ATCC No.10231) 1.9×105 Candida albicans ATCC No.10231 1.9 × 10 5
아스퍼질러스 니거(Aspergillus niger ATCC No.16404) 4.8×105 Aspergillus niger ATCC No.16404 4.8 × 10 5
실시예 2, 비교예 1 및 비교예 2의 조성물을 각각 20g씩 나누어 5종 균주와 혼합하였다. 7, 14, 21 및 28일째에 샘플링하고 10배 계열희석하여 콜로니를 계수하였다.The compositions of Example 2, Comparative Example 1 and Comparative Example 2 were each divided into 20 strains and mixed with five strains. Colonies were counted on day 7, 14, 21 and 28 and 10-fold serial dilution.
방부력 시험 결과는 아래 표 2 내지 4와 같다.Antiseptic test results are shown in Tables 2 to 4 below.
Figure PCTKR2017001620-appb-T000002
Figure PCTKR2017001620-appb-T000002
Figure PCTKR2017001620-appb-T000003
Figure PCTKR2017001620-appb-T000003
Figure PCTKR2017001620-appb-T000004
Figure PCTKR2017001620-appb-T000004
상기 표의 희석 비율은 일 단위의 배양 후 균수를 측정하기 용이하게 하기 위하여, 각 배합의 시료를 멸균된 0.85% NaCl 생리식염수로 1/10(부피비율)단위로 희석한 내용을 표기한 것이다. 직경 90㎜의 배양배지에 수 천, 수 만개의 균수(Colony)를 정확히 계수한다는 것이 어려우므로, 1/10, 1/100, 1/1000 단위로 희석을 진행하여 그 콜로니를 10 내지 300 CFU/㎖로 배양하여 계수하였다.The dilution ratio in the above table indicates the contents of diluting the sample of each compound in 1/10 (volume ratio) units with sterile 0.85% NaCl saline to facilitate the measurement of the number of bacteria after one unit of culture. Since it is difficult to accurately count thousands or tens of thousands of colonies in culture media with a diameter of 90 mm, the colonies are diluted in units of 1/10, 1/100, and 1/1000, and the colonies are 10 to 300 CFU /. Cultured in ml and counted.
상기 표에서 확인되는 바와 같이, 수계조성물에서의 글리세린 카프릴릭산 에스테르와 1,2-헥산디올의 방부력은 양호하지만, 본 발명의 글리세린 젖산 에스테르는 더욱 우수한 방부력을 나타내었다.As can be seen from the above table, although the preservatives of the glycerin caprylic acid ester and 1,2-hexanediol in the aqueous composition were good, the glycerin lactic acid ester of the present invention exhibited better preservation.
그런데 글리세린 카프릴릭산 에스테르는 물과의 혼용성이 떨어져 기름상으로 부유 또는 고체상으로 침전되는 것이 확인되었으며, 수계 조성물에서의 사용은 극히 제한적임을 알 수 있었다.However, glycerin caprylic acid esters were found to be incompatible with water and precipitated in an oily or solid phase, and their use in aqueous compositions was extremely limited.
실시예 3: O/W 제형 로션의 제조Example 3: Preparation of O / W Formulation Lotion
상기 실시예 1에서 제조된 글리세린 젖산 에스테르를 함유하는 0/W 제형의 조성물을 하기 표 5의 조성에 따라 통상의 방법으로 제조하였다.The composition of the 0 / W formulation containing the glycerin lactic acid ester prepared in Example 1 was prepared in a conventional manner according to the composition of Table 5.
시험예 2: 방부력 평가Test Example 2: Evaluation of Antiseptic Force
상기 실시예 3에서 제조된 글리세린 젖산 에스테르의 O/W 제형 조성물의 방부력을 평가하였다. 방부 활성을 가지고 있는 글리세린 카프릴릭산 에스테르 함유 O/W 조성물(비교예 3) 및 대표적인 방부조성물인 1,2-헥산디올을 함유하는 O/W 조성물(비교예 4)을 비교 대상으로 하여 방부력 시험을 진행하였다.The antiseptic power of the O / W formulation composition of the glycerin lactic acid ester prepared in Example 3 was evaluated. Antiseptic force against glycerine caprylic acid ester-containing O / W composition (Comparative Example 3) having antiseptic activity and O / W composition (Comparative Example 4) containing 1,2-hexanediol as a representative antiseptic composition The test was conducted.
Figure PCTKR2017001620-appb-T000005
Figure PCTKR2017001620-appb-T000005
상기 실시예 3, 비교예 3, 4에 대하여 상기 시험예 1과 동일하게 방부력 시험을 진행하였다.In Example 3, Comparative Examples 3 and 4, the antiseptic test was conducted in the same manner as in Test Example 1.
사용된 균주의 종류 및 초기 균수(단위; CFU/㎖)는 다음과 같다.The type of strain used and the number of initial bacteria (unit: CFU / ml) are as follows.
이스케리치아 콜리(Escherichia coli ATCC No.8739) 2.5×106 Escherichia coli ATCC No.8739 2.5 × 10 6
슈도모나스 애루지노사(Pseudomonas aeruginosa ATCC No.10145) 1.8×106 Pseudomonas aeruginosa ATCC No.10145 1.8 × 10 6
스태필로코커스 아우레우스(Staphylococcus aureus ATCC No.6538) 3.2×106 Staphylococcus aureus ATCC No.6538 3.2 × 10 6
칸디다 알비칸스(Candida albicans ATCC No.10231) 2.2×105 Candida albicans ATCC No.10231 2.2 × 10 5
아스퍼질러스 니거(Aspergillus niger ATCC No.16404) 5.0×105 Aspergillus niger ATCC No.16404 5.0 × 10 5
그 결과는 아래 표 6 내지 8과 같다.The results are shown in Tables 6 to 8 below.
Figure PCTKR2017001620-appb-T000006
Figure PCTKR2017001620-appb-T000006
Figure PCTKR2017001620-appb-T000007
Figure PCTKR2017001620-appb-T000007
Figure PCTKR2017001620-appb-T000008
Figure PCTKR2017001620-appb-T000008
본 발명 글리세린 젖산 에스테르를 유효성분으로 함유하는 실시예 3의 O/W 제형의 로션은 글리세린 카프릴릭산 에스테르를 함유하는 비교예 3, 1,2-헥산디올을 함유하는 비교예 4의 로션에 비하여 더욱 우수한 방부활성을 나타내었다. 또한 비교예 3, 4의 경우 로션 제형의 점도가 떨어진다는 단점을 나타내었다(표 5).The lotion of the O / W formulation of Example 3 containing the glycerin lactic acid ester of the present invention as an active ingredient was compared to the lotion of Comparative Example 3 containing the glycerin caprylic acid ester and the comparative example 4 containing 1,2-hexanediol. Better antiseptic activity was shown. In addition, Comparative Examples 3 and 4 showed a disadvantage that the viscosity of the lotion formulation is low (Table 5).
실시예 4: W/O 제형 비비크림의 제조Example 4: Preparation of W / O Formulation BB Cream
상기 실시예 1에서 제조된 글리세린 젖산 에스테르를 함유하는 W/O 제형의 비비크림을 하기 표 9의 조성에 따라 통상의 방법으로 제조하였다.The BB cream of the W / O formulation containing the glycerin lactic acid ester prepared in Example 1 was prepared in a conventional manner according to the composition of Table 9 below.
시험예 3: 방부력 평가Test Example 3: Evaluation of Antiseptic Force
상기 실시예 4에서 제조된 글리세린 젖산 에스테르의 W/O 제형 조성물의 방부력을 평가하였다. 방부 활성을 가지고 있는 글리세린 카프릴릭산 에스테르 함유 W/O 조성물(비교예 5) 및 대표적인 방부조성물인 1,2-헥산디올을 함유하는 W/O 조성물(비교예 6)을 비교 대상으로 하여 방부력 시험을 진행하였다.The antiseptic power of the W / O formulation composition of the glycerin lactic acid ester prepared in Example 4 was evaluated. Antiseptic force against W / O composition containing glycerin caprylic acid ester having antiseptic activity (Comparative Example 5) and W / O composition containing comparative antiseptic composition 1,2-hexanediol (Comparative Example 6) The test was conducted.
Figure PCTKR2017001620-appb-T000009
Figure PCTKR2017001620-appb-T000009
상기 실시예 4, 비교예 5, 6에 대하여 상기 시험예 1과 동일하게 방부력 시험을 진행하였다.In Example 4, Comparative Examples 5 and 6, the antiseptic test was conducted in the same manner as in Test Example 1.
사용된 균주의 종류 및 초기 균수(단위; CFU/㎖)는 다음과 같다.The type of strain used and the number of initial bacteria (unit: CFU / ml) are as follows.
이스케리치아 콜리(Escherichia coli ATCC No.8739) 1.5×106 Escherichia coli ATCC No.8739 1.5 × 10 6
슈도모나스 애루지노사(Pseudomonas aeruginosa ATCC No.10145) 2.1×106 Pseudomonas aeruginosa ATCC No.10145 2.1 × 10 6
스태필로코커스 아우레우스(Staphylococcus aureus ATCC No.6538) 1.8×106 Staphylococcus aureus ATCC No.6538 1.8 × 10 6
칸디다 알비칸스(Candida albicans ATCC No.10231) 1.5×105 Candida albicans ATCC No.10231 1.5 × 10 5
아스퍼질러스 니거(Aspergillus niger ATCC No.16404) 2.2×105 Aspergillus niger (ATSC No.16404) 2.2 × 10 5
그 결과는 아래 표 10 내지 12와 같다.The results are shown in Tables 10 to 12 below.
Figure PCTKR2017001620-appb-T000010
Figure PCTKR2017001620-appb-T000010
Figure PCTKR2017001620-appb-T000011
Figure PCTKR2017001620-appb-T000011
Figure PCTKR2017001620-appb-T000012
Figure PCTKR2017001620-appb-T000012
상기 표들에서 확인되는 바와 같이 본 발명 글리세린 젖산 에스테르를 유효성분으로 함유하는 실시예 4의 W/O 제형의 조성물은 글리세린 카프릴릭산 에스테르를 함유하는 비교예 5, 1,2-헥산디올을 함유하는 비교예 6에 비하여 더욱 우수한 방부활성을 나타내었다. 또한 표 9에서 확인되는 바와 같이, 방부 처방을 하지 않은 비비크림 대비 실시예 4의 글리세린 젖산 에스테르 함유 비비크림은 일정한 점도가 유지되나, 다른 두 방부 처방은 점도가 급격히 떨어짐이 확인되었다.As confirmed in the above tables, the composition of the W / O formulation of Example 4 containing the present invention glycerin lactic acid ester as an active ingredient contains Comparative Example 5, 1,2-hexanediol containing glycerin caprylic acid ester It showed more excellent antiseptic activity compared to Comparative Example 6. In addition, as confirmed in Table 9, the glycerol lactic acid ester-containing BB cream of Example 4 compared to the BB cream without preservative prescription was maintained a constant viscosity, it was confirmed that the viscosity of the other two preservatives drops sharply.
이와 같이, 본 발명의 2-하이드록시-2,3-다이하이드록시프로필 에스테르(2-hydroxy-2,3-dihydroxypropyl ester)를 유효성분으로 함유하는 외용제 조성물은 수형, 수중유형 및 유중수형 제제로 제조되는 경우에도 우수한 방부, 항균활성이 유지되며, 특히 제형의 안정성에 영향을 주지 않아 우수한 혼화성을 나타내었다.As such, the external preparation composition containing 2-hydroxy-2,3-dihydroxypropyl ester of the present invention as an active ingredient may be prepared in water, oil-in-water and water-in-oil type preparations. Even when prepared, excellent antiseptic and antimicrobial activity is maintained, and especially, it does not affect the stability of the formulation, and shows excellent miscibility.
이상으로 본 발명의 특정한 부분을 상세히 기술하였는바, 당 업계의 통상의 지식을 가진 자에게 있어서 이러한 구체적인 기술은 단지 바람직한 구현예일 뿐이며, 이에 본 발명의 범위가 제한되는 것이 아닌 점은 명백하다. 따라서 본 발명의 실질적인 범위는 첨부된 청구항과 그의 등가물에 의하여 정의된다고 할 것이다.As described above in detail specific parts of the present invention, it is apparent to those skilled in the art that these specific techniques are merely preferred embodiments, and thus the scope of the present invention is not limited thereto. Therefore, the substantial scope of the present invention will be defined by the appended claims and equivalents thereof.
광범위한 항균, 방부 스펙트럼　및 혼화성을 갖는 본 발명의 외용제 조성물은 의약, 화장품, 생활용품 뿐 아니라 의약외품, 농약 등에서 항균, 살균, 소독, 방부 등의 목적을 달성하기 위해 광범위하게 사용될 수 있다.The external preparation composition of the present invention having a wide range of antimicrobial, antiseptic spectrum and miscibility can be widely used to achieve the purpose of antibacterial, sterilization, disinfection, antiseptic, etc. in medicinal products, cosmetics, household goods as well as quasi-drugs, pesticides and the like.

Claims (6)

  1. 하기 화학식 1로 표시되는 글리세린 젖산 에스테르 화합물을 유효성분으로 포함하는 방부 및 항균용 외용제 조성물.An external preparation composition for antiseptic and antibacterial comprising a glycerin lactic acid ester compound represented by the following Formula 1 as an active ingredient.
    [화학식 1][Formula 1]
    Figure PCTKR2017001620-appb-I000005
    Figure PCTKR2017001620-appb-I000005
  2. 제1항에 있어서, 상기 외용제 조성물은 이스케리치아(Escherichia) 속, 슈도모나스(Pseudomonas) 속, 스태필로코커스(Staphylococcus) 속, 칸디다(Candida) 속 및 아스퍼질러스(Aspergillus) 속으로 구성된 군으로부터 선택되는 미생물에 대하여 방부, 항균 활성을 나타내는 것을 특징으로 하는 방부 및 항균용 외용제 조성물.The method of claim 1, wherein the external composition is selected from the group consisting of the genus Esccherichia, Pseudomonas, Staphylococcus, Candida, and Aspergillus. Antiseptic and antimicrobial external preparation composition characterized by showing antiseptic and antimicrobial activity against the microorganisms.
  3. 제2항에 있어서, 상기 조성물은 이스케리치아 콜리(Escherichia coli), 슈도모나스 애루지노사(Pseudomonas aeruginosa), 스태필로코커스 아우레우스(Staphylococcus aureus), 칸디다 알비칸스(Candida albicans) 및 아스퍼질러스 니거(Aspergillus niger)로 구성된 군으로부터 선택되는 미생물에 대하여 방부, 항균 활성을 나타내는 것을 특징으로 하는 방부 및 항균용 외용제 조성물.The composition of claim 2, wherein the composition is Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Candida albicans and Aspergillus sniger. (Aspergillus niger) antiseptic and antimicrobial external preparation composition characterized by showing antiseptic and antimicrobial activity against a microorganism selected from the group consisting of.
  4. 제1항에 있어서, 상기 방부 및 항균용 외용제 조성물은 수형(water type), 수중유형(oil in water type) 또는 유중수형(water in oil type)의 제형을 가지는 것임을 특징으로 하는 방부 및 항균용 외용제 조성물.The antiseptic and antibacterial external preparation according to claim 1, wherein the antiseptic and antimicrobial external preparation composition has a water type, an oil in water type or a water in oil type formulation. Composition.
  5. 제1항에 있어서, 상기 글리세린 젖산 에스테르 화합물은 외용제 조성물 전체 중량에 대하여 0.1~10.0%(w/w)포함되는 것임을 특징으로 하는 방부 및 항균용 외용제 조성물.According to claim 1, wherein the glycerin lactic acid ester compound is an external preparation for antiseptic and antimicrobial composition, characterized in that 0.1 to 10.0% (w / w) based on the total weight of the external preparation composition.
  6. 제1항에 있어서, 상기 방부 및 항균용 조성물은 약학 조성물, 화장료 조성물 또는 생활용품 조성물인 것을 특징으로 하는 방부 및 항균용 외용제 조성물.The antiseptic and antimicrobial external preparation composition according to claim 1, wherein the antiseptic and antimicrobial composition is a pharmaceutical composition, a cosmetic composition or a household composition.
PCT/KR2017/001620 2016-09-12 2017-02-15 Antiseptic and antibacterial composition for external application, containing glycerin lactic acid ester as active ingredient WO2018048042A1 (en)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6977082B2 (en) * 2001-03-29 2005-12-20 The Dial Corporation High efficacy antibacterial compositions having enhanced esthetic and skin care properties
KR20080009479A (en) * 2006-07-24 2008-01-29 정병윤 The eco-friendly preventive composition of vermin and disease in the crops
KR20080067814A (en) * 2007-01-17 2008-07-22 주식회사 엘지생활건강 Transparent soap composition
US20120029075A1 (en) * 2009-03-16 2012-02-02 Fernando Cantini Compositions containing c1 to c7 organic acid monoglycerides and glycerol, their preparation and use as antibacterials and anti-mould agents
KR20160025034A (en) * 2008-10-17 2016-03-07 페레르 인터내쇼날 에스.에이. Pharmaceutical topical compositions

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6977082B2 (en) * 2001-03-29 2005-12-20 The Dial Corporation High efficacy antibacterial compositions having enhanced esthetic and skin care properties
KR20080009479A (en) * 2006-07-24 2008-01-29 정병윤 The eco-friendly preventive composition of vermin and disease in the crops
KR20080067814A (en) * 2007-01-17 2008-07-22 주식회사 엘지생활건강 Transparent soap composition
KR20160025034A (en) * 2008-10-17 2016-03-07 페레르 인터내쇼날 에스.에이. Pharmaceutical topical compositions
US20120029075A1 (en) * 2009-03-16 2012-02-02 Fernando Cantini Compositions containing c1 to c7 organic acid monoglycerides and glycerol, their preparation and use as antibacterials and anti-mould agents

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