KR102320505B1 - Antibacterial Composition containing meso-2,3-butanediol - Google Patents

Antibacterial Composition containing meso-2,3-butanediol Download PDF

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KR102320505B1
KR102320505B1 KR1020140142817A KR20140142817A KR102320505B1 KR 102320505 B1 KR102320505 B1 KR 102320505B1 KR 1020140142817 A KR1020140142817 A KR 1020140142817A KR 20140142817 A KR20140142817 A KR 20140142817A KR 102320505 B1 KR102320505 B1 KR 102320505B1
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butanediol
composition
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백흥수
우병영
유세진
주영협
신송석
이존환
김서영
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지에스칼텍스 주식회사
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Priority to PCT/KR2015/011120 priority patent/WO2016064180A1/en
Priority to CN201580055329.0A priority patent/CN106794122B/en
Priority to ES15853159T priority patent/ES2836746T3/en
Priority to US15/518,428 priority patent/US10525017B2/en
Priority to JP2017521242A priority patent/JP6976169B2/en
Priority to EP15853159.0A priority patent/EP3195851B1/en
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    • 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
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/06—Unsaturated carboxylic acids or thio analogues thereof; Derivatives thereof
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    • 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
    • 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
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    • A61K8/345—Alcohols containing more than one hydroxy group
    • 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
    • A61Q19/10—Washing or bathing preparations
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions

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Abstract

본 발명은 2,3-부탄디올의 이성질체인 하기 화학식 1로 표현되는 메조(meso)-2,3-부탄디올을 함유함으로써 세균을 효과적으로 제어할 수 있으며, 적은 양으로도 우수한 항균 효과를 나타낼 수 있는 항균용 조성물에 관한 것이다.
[화학식 1]

Figure 112014100549693-pat00006
The present invention can effectively control bacteria by containing meso-2,3-butanediol represented by the following Chemical Formula 1, which is an isomer of 2,3-butanediol, and can exhibit excellent antibacterial effect even in a small amount. It relates to a composition for
[Formula 1]
Figure 112014100549693-pat00006

Description

메조-2,3-부탄디올을 함유하는 항균용 조성물{Antibacterial Composition containing meso-2,3-butanediol}Antibacterial composition containing meso-2,3-butanediol

본 발명은 2,3-부탄디올의 이성질체인 메조(meso)-2,3-부탄디올을 함유함으로써 세균을 효과적으로 제어할 수 있으며, 적은 양으로도 우수한 항균 효과를 나타낼 수 있는 항균용 조성물에 관한 것이다.
The present invention relates to an antibacterial composition capable of effectively controlling bacteria and exhibiting excellent antibacterial effect even in a small amount by containing meso-2,3-butanediol, which is an isomer of 2,3-butanediol.

미생물은 우리 주변에 항상 존재하고 있는 생명체로서, 인간에게 도움을 주는 유익한 미생물도 존재하지만, 한편으로는 질병을 유발하고 악취를 만들며, 미관상 혐오감을 주는 등의 문제를 일으키는 해로운 미생물도 존재한다. 특히, 머리카락(hair), 몸(body), 손(hand), 발(foot) 등의 신체에도 외부적인 환경에 의하여 미생물이 존재하며, 애완동물의 털 등에도 미생물이 다량으로 존재한다. 또한 야채, 과일, 어류 등의 식품, 식품의 조리기구, 식기류 또는 조리 장소에도 미생물이 존재하며, 화장실 등에도 미생물이 존재하는 등 미생물은 우리 주변의 곳곳에 항상 존재하고 있다. Microorganisms are living things that exist all the time around us, and there are beneficial microorganisms that help humans, but there are also harmful microorganisms that cause problems such as disease, odor, and aesthetic disgust. In particular, microbes exist in the body such as hair, body, hands, and feet due to the external environment, and microbes are also present in large amounts in the hair of pets. In addition, microorganisms are present in foods such as vegetables, fruits and fish, cooking utensils, tableware, or cooking places of food, and microorganisms are also present in toilets, etc. Microorganisms are always present everywhere around us.

이들 존재하는 미생물들로 인하여 인간의 생활은 위협받고 있으며, 안전하고 위생적인 생활을 위해서 미생물의 살균 및 세척을 위한 항균제의 필요성이 있고, 이에 따라 다양한 항균제의 개발이 이루어지고 있다.
Human life is threatened by these existing microorganisms, and there is a need for an antimicrobial agent for sterilization and washing of microorganisms for a safe and hygienic life, and accordingly, various antibacterial agents have been developed.

국내 특허공개 10-2011-0058237호(2011년 6월 1일 공개)Domestic Patent Publication No. 10-2011-0058237 (published on June 1, 2011)

이에 본 발명자들은 피부 및 주변 환경에 존재하는 세균을 효과적으로 제어할 수 있는 물질을 연구한 결과, 메조-2,3-부탄디올이 우수한 항균력을 가진다는 것을 발견하여 본 발명을 완성하게 되었다.Accordingly, the present inventors have completed the present invention by discovering that meso-2,3-butanediol has excellent antibacterial activity as a result of studying a material that can effectively control bacteria present in the skin and the surrounding environment.

따라서, 본 발명의 목적은 항균력이 높아 적은 양의 사용으로도 세균을 효과적으로 제어할 수 있는 항균용 조성물을 제공하는 것이다.
Accordingly, an object of the present invention is to provide an antibacterial composition that can effectively control bacteria even with a small amount of high antibacterial activity.

상기한 목적을 달성하기 위하여, 본 발명은 하기 화학식 1로 표현되는 메조-2,3-부탄디올을 함유하는 항균용 조성물을 제공한다.In order to achieve the above object, the present invention provides an antibacterial composition containing meso-2,3-butanediol represented by the following formula (1).

Figure 112014100549693-pat00001
Figure 112014100549693-pat00001

본 발명에 따른 메조-2,3-부탄디올을 함유하는 조성물은, 적은 양의 사용으로도 우수한 항균 효과를 나타내며, 이를 통해 세균 및 곰팡이에 의해서 감염되는 각종 습진 등의 피부 질환을 경감 및 개선할 수 있다.
The composition containing meso-2,3-butanediol according to the present invention exhibits an excellent antibacterial effect even when used in a small amount, thereby reducing and improving skin diseases such as various eczema infected by bacteria and fungi. have.

본 발명은 메조-2,3-부탄디올을 함유하는 항균용 조성물, 특히 항균용 세정제 조성물을 제공한다.The present invention provides an antibacterial composition containing meso-2,3-butanediol, in particular, an antibacterial detergent composition.

2,3-부탄디올은 일반적으로 발효에 의해 생산되는 것으로서, Klebsiella pneumoniae, Bacillus polymyxa, Enterobacter aerogenes 등의 박테리아에 의해 생산되기도 하고, 펜토스(Pentoses), 자일로스(Xylose) 및 아라비노스(Arabinose) 등을 원료로 하여 화학적으로 합성되기도 한다. 2,3-butanediol is generally produced by fermentation, Klebsiella pneumoniae , Bacillus polymyxa , Enterobacter It is sometimes produced by bacteria such as aerogenes, or it is chemically synthesized using pentoses, xylose, and arabinose as raw materials.

특히, 화장품 등의 피부 외용제에서 2,3-부탄디올은 통상적으로 피부연화제(emollient), 보습제(humectants) 또는 습윤제(wetting agent) 등의 성분으로 조성물에 포함되어 사용되어 왔다.In particular, in external preparations for skin such as cosmetics, 2,3-butanediol has been conventionally used as a component such as an emollient, humectants or wetting agent in the composition.

2,3-부탄디올은 입체 화학적으로 보면 세가지 이성질체들로 구분할 수 있다. 즉, 메조(Meso)-2,3-부탄디올, S,S-2,3-부탄디올, R,R-2,3-부탄디올로 구분할 수 있으며, 이들 각각의 구조는 하기 화학식 1 내지 3에 나타내어져 있다.2,3-butanediol can be classified into three isomers stereochemically. That is, it can be divided into meso-2,3-butanediol, S,S-2,3-butanediol, and R,R-2,3-butanediol, and their respective structures are shown in Formulas 1 to 3 below, have.

[화학식 1][Formula 1]

Figure 112014100549693-pat00002
Figure 112014100549693-pat00002

Figure 112014100549693-pat00003
Figure 112014100549693-pat00003

Figure 112014100549693-pat00004
Figure 112014100549693-pat00004

이러한 2,3-부탄디올의 3가지 입체 이성질체 중에서, 특히 메조-2,3-부탄디올은 다른 입체 이성질체에 비하여 항균력이 높다는 특성을 가진다.Among these three stereoisomers of 2,3-butanediol, meso-2,3-butanediol, in particular, has a high antibacterial activity compared to other stereoisomers.

따라서, 본 발명에 따른 조성물은 항균력이 있는 메조-2,3-부탄디올을 사용함으로써 적은 양의 사용으로도 우수한 항균력을 나타내는 조성물을 제공할 수 있다. Therefore, the composition according to the present invention can provide a composition exhibiting excellent antibacterial activity even with a small amount of meso-2,3-butanediol by using the antibacterial meso-2,3-butanediol.

본 발명에 있어서, “항균”이란, 박테리아, 곰팡이 및 효모 등의 오염 미생물 전부에 대한 저항성을 의미하는 것으로서, 즉 항세균, 항진균 등의 의미를 모두 포함하는 것이며, “항균력”이란, 이들 오염 미생물에 대한 방어력을 의미하는 것이다. In the present invention, "antibacterial" means resistance to all contaminating microorganisms such as bacteria, mold and yeast, that is, includes all meanings such as antibacterial and antifungal, and "antibacterial power" means these contaminating microorganisms It means defense against

본 발명에 있어서, 항균력을 유효하게 발휘시키기 위해서, 메조-2,3-부탄디올은 조성물 총 중량을 기준으로 0.001중량% 이상, 바람직하게는 0.5중량% 이상, 구체적으로는 1.0중량% 이상, 더 바람직하게는 2.0중량% 이상의 비율로 배합될 수 있다. 또한, 조성물 내의 다른 성분들의 유효 함량으로서의 배합 및 메조-2,3-부탄디올의 배합에 따른 효율성을 고려하여, 메조-2,3-부탄디올의 함량은 20중량% 이하, 또는 10중량% 이하로 제한될 수 있다.In the present invention, in order to effectively exhibit antibacterial activity, meso-2,3-butanediol is 0.001% by weight or more, preferably 0.5% by weight or more, more preferably 1.0% by weight or more, based on the total weight of the composition. For example, it may be blended in a proportion of 2.0% by weight or more. In addition, in consideration of the efficiency according to the formulation and the formulation of meso-2,3-butanediol as an effective content of the other components in the composition, the content of meso-2,3-butanediol is limited to 20 wt% or less, or 10 wt% or less can be

본 발명의 조성물에 사용되는 메조-2,3-부탄디올은, 통상의 공지 방법을 통해 제조되어 조성물 내에 배합될 수 있으며, 시판품을 조성물 내에 배합하는 것도 가능하다.The meso-2,3-butanediol used in the composition of the present invention may be prepared through a conventionally known method and blended into the composition, and a commercially available product may be blended into the composition.

본 발명의 조성물은 피부 외용제 조성물, 구체적으로 화장료 조성물, 약학 조성물 등일 수 있다. 또한, 상기 조성물은 예를 들어, 화장류, 크림, 로션, 파우더, 에센스 또는 팩 등의 형태로 제형화될 수 있으며, 그 제형이 특별히 한정되는 것은 아니다. 또한, 각각의 제형에 있어서, 다른 성분들은 기타 조성물의 종류 또는 사용목적 등에 따라 당업자가 어려움 없이 적의 선정하여 배합할 수 있다.The composition of the present invention may be a composition for external application to the skin, specifically, a cosmetic composition, a pharmaceutical composition, and the like. In addition, the composition may be formulated in the form of, for example, cosmetics, cream, lotion, powder, essence or pack, and the formulation is not particularly limited. In addition, in each formulation, other components may be appropriately selected and formulated by those skilled in the art without difficulty depending on the type or purpose of use of other compositions.

또한, 본 발명의 조성물은 바람직하게 세정제 조성물로 제형화될 수 있으며, 그 제형이 특별히 한정되는 것은 아니지만, 구체적으로는 손소독제, 핸드워시, 바디워시, 클렌징 크림, 클렌징 젤, 클렌징 폼, 클렌징 워터, 비누, 물티슈 등의 형태로 제형화될 수 있다.In addition, the composition of the present invention may be preferably formulated as a cleaning composition, and the formulation is not particularly limited, but specifically hand sanitizer, hand wash, body wash, cleansing cream, cleansing gel, cleansing foam, and cleansing water. , soap, wet tissue, and the like.

또한, 본 발명의 조성물은 주변 환경에의 적용이 용이한 형태, 예를 들어 스프레이, 물티슈 등의 형태로 제형화될 수 있다.
In addition, the composition of the present invention may be formulated in a form that is easy to apply to the surrounding environment, for example, in the form of a spray, wet tissue, and the like.

이하, 본 발명의 바람직한 시험예 등을 통해 본 발명을 더욱 상술하지만, 하기 시험예 등은 본 발명의 효과를 예시적으로 확인하기 위한 것이며, 본 발명의 범주가 이들만으로 한정되는 것은 아니다.
Hereinafter, the present invention will be described in more detail through preferred test examples of the present invention, but the following test examples and the like are for illustratively confirming the effects of the present invention, and the scope of the present invention is not limited thereto.

[시험예 1] 항균력 시험[Test Example 1] Antibacterial activity test

디올류(diol)의 히드록시기 위치와 입체적 배향에 따른 항균력을 비교하기 위하여 하기 표 1에 기재된 시료, 즉, 1,3-부탄디올 등 6종의 디올류들에 대한 항균력을 측정하였다. 항균력 측정 시험은, 대장균(Escherichia coli; ATCC 8739), 슈도모나스 애루지노사(Pseudomonas aeruginosa; ATCC 9027), 스타필로코쿠스 아우레우스(Staphlyococcus aureus; ATCC 6538), 칸디다 알비칸스(Candida albicans; ATCC 10231) 및 아스퍼질러스 니거(Aspergillus niger; ATCC 16404) 등의 박테리아, 효모 및 곰팡이에 대하여 실시하였다. 각 물질들을 0.01~10%의 농도로 트립틱 소이(Tryptic Soy broth) 배지 및 사부로덱스트로스(SD) 배지에 첨가한 후 배양액을 액상으로 제조하고, 상기한 박테리아, 효모 및 곰팡이균을 접종한 다음 25~32℃에서 24~72시간 동안 배양하고 균의 상태를 관찰하였다. 접종한 초기의 균수를 현저히 감소시키는 농도를 최소생육저해농도(MIC)로 하여 항균력을 측정하였으며, 그 결과를 하기 표 1에 나타내었다.In order to compare the antimicrobial activity according to the hydroxyl group position and three-dimensional orientation of the diol, the antimicrobial activity against the samples shown in Table 1 below, that is, 6 types of diols such as 1,3-butanediol, was measured. Antibacterial activity measurement test, Escherichia coli ; ATCC 8739), Pseudomonas aeruginosa aeruginosa ; ATCC 9027), Staphlyococcus aureus aureus ; ATCC 6538), Candida albicans (Candida albicans ; ATCC 10231) and Aspergillus niger niger ; ATCC 16404), et al., bacteria, yeast and mold. After adding each substance to a tryptic soy broth medium and saburodextrose (SD) medium at a concentration of 0.01 to 10%, the culture solution is prepared as a liquid, and the above-mentioned bacteria, yeast and mold are inoculated. It was cultured at 25-32°C for 24-72 hours and the state of the bacteria was observed. The antibacterial activity was measured by using the minimum growth inhibitory concentration (MIC) at the concentration that significantly reduced the number of inoculated initial bacteria, and the results are shown in Table 1 below.

시험물질test substance 대장균coli P. P. aeruginosaaeruginosa S. S. aureusaureus C. C. albicansalbicans A. A. nigerniger 1,3-부탄디올1,3-butanediol >10>10 >10>10 >10>10 >10>10 >10>10 1,2-부탄디올1,2-Butanediol 55 2.52.5 1.251.25 55 2.52.5 S,S-2,3-부탄디올S,S-2,3-butanediol 55 55 2.52.5 55 1.251.25 R,R-2,3-부탄디올R,R-2,3-butanediol 2.52.5 55 1010 55 55 메조-2,3-부탄디올Meso-2,3-butanediol 1.251.25 2.52.5 55 2.52.5 1.251.25 1,2-헥산디올1,2-Hexanediol 1.251.25 1.251.25 2.52.5 1.251.25 0.6250.625

상기 표 1의 결과를 보면, 디올류의 항균력이 히드록시기 위치에 따라 차이가 있는 것으로 나타났으며, 본 발명에서 사용되는 메조-2,3-부탄디올은 항균력이 우수한 것을 확인할 수 있다.Looking at the results of Table 1, it was found that the antimicrobial activity of diols differs depending on the position of the hydroxyl group, and it can be confirmed that the meso-2,3-butanediol used in the present invention has excellent antibacterial activity.

Claims (5)

하기 화학식 1로 표현되는 메조-2,3-부탄디올을 대장균, 슈도모나스 애루지노사(Pseudomonas aeruginosa) 및 칸디다 알비칸스(Candida albicans)로 구성되는 군으로부터 선택되는 하나 이상에 대한 항균제로서 함유하며, S,S-2,3-부탄디올 및 R,R-2,3-부탄디올은 항균제로서 함유하지 않는 항균용 조성물.
[화학식 1]
Figure 112021057161715-pat00005
Meso-2,3-butanediol represented by the following formula (1 ) is contained as an antibacterial agent for E. coli, Pseudomonas aeruginosa and at least one selected from the group consisting of Candida albicans, S, An antibacterial composition that does not contain S-2,3-butanediol and R,R-2,3-butanediol as an antibacterial agent.
[Formula 1]
Figure 112021057161715-pat00005
 제1항에 있어서, 상기 메조-2,3-부탄디올의 함량은 조성물 총 중량을 기준으로 0.001 내지 20중량%인 것을 특징으로 하는 조성물.The composition according to claim 1, wherein the content of meso-2,3-butanediol is 0.001 to 20% by weight based on the total weight of the composition. 제2항에 있어서, 상기 메조-2,3-부탄디올의 함량은 조성물 총 중량을 기준으로 2.0 내지 10중량%인 것을 특징으로 하는 조성물.The composition according to claim 2, wherein the content of meso-2,3-butanediol is 2.0 to 10% by weight based on the total weight of the composition. 제1항에 있어서, 상기 조성물은 세정제임을 특징으로 하는 조성물.The composition of claim 1, wherein the composition is a cleaning agent. 제1항 내지 제4항 중 어느 한 항에 있어서, 상기 조성물은 화장류, 크림, 로션, 파우더, 에센스, 팩, 손소독제, 핸드워시, 바디워시, 클렌징 크림, 클렌징 젤, 클렌징 폼, 클렌징 워터, 비누 또는 물티슈의 형태로 제형화됨을 특징으로 하는 조성물.According to any one of claims 1 to 4, wherein the composition is cosmetics, cream, lotion, powder, essence, pack, hand sanitizer, hand wash, body wash, cleansing cream, cleansing gel, cleansing foam, cleansing water , a composition characterized in that it is formulated in the form of a soap or wet tissue.
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