KR100659139B1 - Oral composition having a good antibacterial effect - Google Patents

Oral composition having a good antibacterial effect Download PDF

Info

Publication number
KR100659139B1
KR100659139B1 KR1020060003151A KR20060003151A KR100659139B1 KR 100659139 B1 KR100659139 B1 KR 100659139B1 KR 1020060003151 A KR1020060003151 A KR 1020060003151A KR 20060003151 A KR20060003151 A KR 20060003151A KR 100659139 B1 KR100659139 B1 KR 100659139B1
Authority
KR
South Korea
Prior art keywords
composition
oral
zinc
weight
oral cavity
Prior art date
Application number
KR1020060003151A
Other languages
Korean (ko)
Inventor
김대경
강계홍
신계호
김기정
이병렬
Original Assignee
(주)아모레퍼시픽
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by (주)아모레퍼시픽 filed Critical (주)아모레퍼시픽
Priority to KR1020060003151A priority Critical patent/KR100659139B1/en
Application granted granted Critical
Publication of KR100659139B1 publication Critical patent/KR100659139B1/en

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/4906Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
    • A61K8/4926Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/19Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
    • A61K8/27Zinc; Compounds thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42Amides
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/60Sugars; Derivatives thereof
    • A61K8/602Glycosides, e.g. rutin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00Barrier 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
    • A61Q17/005Antimicrobial preparations
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/54Polymers characterized by specific structures/properties
    • A61K2800/542Polymers characterized by specific structures/properties characterized by the charge
    • A61K2800/5426Polymers characterized by specific structures/properties characterized by the charge cationic

Abstract

An oral composition having good antibacterial effects is provided to enhance antibacterial activity, prevent lowering of antibacterial activity, and bring up the antibacterial effects after its employment due to teethridge contraction and elasticity feeling. The oral composition having good antibacterial effects comprises 0.01-5 wt.% of cationic sterilizing agent, 4-10 wt.% of nonionic surfactant, and 0.01-2 wt.% of astringent, wherein the cationic sterilizing agent is cetyl pyridinium chloride; the nonionic surfactant is lauryl glucoside, cocamide DEA or polysorbate 20; and the astringent is a zinc compound such as zinc chloride, zinc oxide, zinc sulfate and zinc gluconate or a natural additive such as tannin.

Description

항균력이 우수한 구강용 조성물{Oral composition having a good antibacterial effect}Oral composition having a good antibacterial effect

본 발명은 양이온성 살균제, 비이온성 계면활성제 및 수렴제를 함유하는 구강용 조성물에 관한 것이다. 보다 상세하게는, 본 발명의 구강용 조성물은 양이온성 살균제와 이의 활성의 불활성화를 방지할 수 있는 특정의 비이온성 계면활성제를 최적의 배합농도로 함유하고, 사용 후 잇몸질환의 효능을 연상시키는 사용감을 주는 수렴제를 함유함으로써, 구강균에 대한 항균력이 더욱 증진되어 구강균에 의해 야기될 수 있는 각종 잇몸질환과 충치 등의 구강질환을 예방하고, 사용 후에도 이러한 효과를 연상하게 하는 연상 사용감을 나타낸다. The present invention relates to compositions for oral cavity containing cationic fungicides, nonionic surfactants and astringents. More specifically, the composition for oral cavity of the present invention contains a cationic fungicide and a specific nonionic surfactant which can prevent the inactivation of its activity at an optimum blending concentration, and reminiscent of the efficacy of gum disease after use. By containing astringents that give a feeling of use, the antibacterial activity against oral bacteria is further enhanced to prevent oral diseases such as various gum diseases and tooth decay, which can be caused by oral bacteria, and suggest a feeling of reminiscent of these effects even after use.

일반적으로 각종 구강 질환은 구강에 살고 있는 각종 세균들에 의해 발생한다. 상기 세균들은 충치를 발생시키는 세균과 잇몸질환을 유발시키는 세균으로 구분할 수 있으며, 각각 대표적으로 스트렙토코커스 뮤탄스(S. mutans)균과 치주질환 유발균인 포피로모나스 진지바리스(P. gingivalis)가 있다. 이러한 구강균을 제거하기 위해 각종 살균제들이 구강용 조성물에서 많이 사용되어져 왔다. 구강용 제품에 사용되는 살균제에는 염화세틸피리디늄, 염화헥살코늄, 염화벤잘코니움, 염화데 카리늄, 클로로헥시딘, 트리클로산, 티몰, 이소프로필메칠페놀, 염화알킬디아미노에칠글리산 등의 원료들과 천연추출 성분인 폴리페놀류, 그리고 은 성분 등이 있다.  이러한 살균제들은 세균 표면의 음이온성의 인산기나 카르복실기를 목표로 양이온성 살균제가 흡착하게 되고, 그 후 세포벽에 있는 효소가 저해되고 최후에는 세균의 세포벽을 파괴하여 살균을 하는 메카니즘을 따른다.In general, various oral diseases are caused by various bacteria living in the oral cavity. The bacteria may be classified into bacteria causing tooth decay and bacteria causing gum disease. Representatively, Streptococcus mutans and periodontal disease-inducing bacteria P. gingivalis have. Various fungicides have been used in oral compositions to remove such oral bacteria. Fungicides used in oral products include cetylpyridinium chloride, hexahalonium chloride, benzalkonium chloride, decarinium chloride, chlorohexidine, triclosan, thymol, isopropylmethylphenol and alkyldiaminoethylglycolic acid. Raw materials, natural extracts, polyphenols, and silver. These fungicides follow a mechanism in which cationic fungicides are adsorbed to target anionic phosphate groups or carboxyl groups on the surface of bacteria, and then enzymes in the cell wall are inhibited and finally destroys the cell wall of bacteria.

구강용 조성물에 관한 구체적인 기술로는 한국 공개특허 제 2005-0010082호에는 인체에 무해하면서 천연항생물질로 알려진 은용액, 은분말 또는 은박막편을 첨가하여 뛰어난 살균 효과 및 항균효과를 제공하게 되면서, 아울러 치아를 희게 하고 구강내를 상쾌하게 하는 구강용 조성물이 기재되어 있다. 또한, 한국 공개특허 제 2005-0035954호에는 충치 유발균인 스트렙토코커스 뮤탄스(S. mutans)균과 치주질환 유발균인 포피로모나스 진지바리스(P. gingivalis)에 대한 항균활성이 매우 높은 리그난 유도체를 함유하여 충치와 잇몸질환 예방에 효과적이고, 이를 항균제 뿐만 아니라 치약조성물, 구강 청정제, 검, 캔디 등 다양한 제형의 조성물에 이용하는 기술이 기재되어 있다. 또한, 한국 공개특허 제 2001-0001476호에는 구강 살균제, 치주질환 억제제, 플라보노이드를 함유하여 구강내 세균, 치주질환 및 악취 유발물질을 제거하여 구취를 억제하는 조성물이 기재되어 있다. 이때, 사용되는 구강 살균제로는 트리클로산, 세틸피리디늄클로라이드, 상귀나린, 티몰 등에서 선택된 1종 또는 2종 이상을 사용하고 있다. 또한, 한국 공개특허 제 2001-0026581호에는 정향 추출물을 함유하여 입안을 가글시 청량감을 제공할 뿐만 아니라 항균활성으로 인한 구취제거 및 잇몸질환을 예방하는데 뛰어난 효과가 있고, 기존의 청정 제가 지니지 못한 진통효과를 갖고 있는 조성물이 기재되어 있다. 또한, 한국 특허출원 제 1998-0014437호에는 다공성 탄산칼슘을 첨가하여 트리클로산과 같은 수불용성 비양이온계 살균제의 살균 활성 저하를 막아 치태제거, 구취방지 및 치아 착색물질의 제거에 효과적인 구강용 조성물이 기재되어 있다. As a specific technology related to the composition for oral cavity, Korean Patent Publication No. 2005-0010082 is a harmless to the human body while adding a silver solution, silver powder or silver thin film pieces known as natural antibiotics to provide excellent sterilization and antibacterial effect, Oral compositions for whitening teeth and refreshing the oral cavity are described. In addition, Korean Patent Laid-Open No. 2005-0035954 discloses lignan derivatives having high antimicrobial activity against S. mutans , a decay-causing bacterium, and P. gingivalis, a bacterium causing periodontal disease. It is effective in the prevention of tooth decay and gum disease, it is described as a technique for use in the composition of various formulations, such as toothpaste composition, mouthwash, gum, candy as well as antibacterial. In addition, Korean Patent Laid-Open Publication No. 2001-0001476 discloses a composition containing oral fungicides, periodontal disease inhibitors, and flavonoids to suppress bad breath by removing bacteria, periodontal disease and odor causing substances in the oral cavity. In this case, as the oral fungicide used, one or two or more selected from triclosan, cetylpyridinium chloride, sanguinarin, thymol and the like are used. In addition, Korean Laid-Open Patent Publication No. 2001-0026581 contains a clove extract, which not only provides a refreshing feeling when the mouth is gargled, but also has an excellent effect in preventing bad breath and gum disease due to antibacterial activity, and pain relief that does not have a conventional cleanser. A composition having an effect is described. In addition, Korean Patent Application No. 1998-0014437 discloses an oral composition effective for removing plaque, preventing bad breath and removing tooth coloring substances by preventing the degradation of the bactericidal activity of water-insoluble noncationic fungicides such as triclosan by adding porous calcium carbonate. It is.

상기의 기재와 같이, 구강용 조성물에 있어서 살균제 등이 충치예방, 잇몸질환 예방, 구취억제의 목적으로 배합되어 사용되어져 오고 있으나, 대개의 경우 빈약한 항균 효과를 나타내고 있으며 좋은 효과를 나타내는 경우에는 안정도에 좋지 않은 측면을 가지고 있어 구강용 조성물에 사용하는데 있어서 어려움이 있다. 또한, 실제로 좋은 효능 효과를 나타내면서도 소비자가 그 효능을 인지하지 못하여 제품에 대한 신뢰성을 잃는 경우가 많이 있다.As described above, in the oral composition, a disinfectant or the like has been used for the purpose of preventing tooth decay, preventing gum disease, and preventing bad breath, but in most cases, it shows poor antibacterial effect and stability in case of showing good effect. It is difficult to use in the composition for oral cavity because it has a bad side. In addition, there are many cases in which the consumer may not be aware of the efficacy while showing a good efficacy effect and thus lose the reliability of the product.

       

이에, 본 발명자들은 구강균에 대하여 강력한 항균효과를 갖는 조성성분들을 연구한 결과, 양이온성 암모늄염 살균제가 구강내 존재하는 구강균에 대해 강력한 항균력을 나타내고, 상기 살균제의 항균 활성 저하를 방지하는 비이온성 계면활성제가 그 종류 및 배합농도에 따라 항균력이 크게 차이가 있음을 밝혀내었다. 또한, 천연물질, 아연화합물 등이 구강용 조성물에서 잇몸질환 예방효과를 연상시키는 사용감을 나타냄을 확인하고, 본 발명을 완성하였다. Accordingly, the present inventors studied the components having a strong antimicrobial effect against oral bacteria, the cationic ammonium salt fungicide exhibits a strong antimicrobial activity against oral bacteria present in the oral cavity, non-ionic surfactant to prevent the antimicrobial activity of the fungicide deterioration The antimicrobial activity was found to vary greatly depending on the type and the concentration of the compound. In addition, it was confirmed that natural substances, zinc compounds, etc. exhibit a feeling reminiscent of gum disease prevention effect in the composition for oral cavity, and completed the present invention.

따라서, 본 발명의 목적은 구강균에 대하여 강력한 항균력을 나타내면서 사용후에도 잇몸수축감, 탄력감으로 그 효과를 연상하게 하는 사용감을 나타내는 구 강용 조성물을 제공하는 것이다. Accordingly, it is an object of the present invention to provide a composition for oral cavity showing a feeling of use that reminds the effect of gum shrinkage, elasticity even after use while showing a strong antibacterial activity against oral bacteria.

상기한 목적을 달성하기 위하여, 본 발명에 의한 구강용 조성물은 조성물 총 중량에 대하여 양이온성 살균제 0.01~5 중량%, 라우릴 글루코시드, 코카마이드 DEA 및 폴리솔베이트 20으로 이루어진 군에서 선택된 1종 이상의 비이온성 계면활성제 4~10 중량%을 함유함을 특징으로 한다. 또한, 상기 조성물에 수렴제 0.01~2.0 중량%를 더 함유하는 것을 특징으로 한다. In order to achieve the above object, the composition for oral cavity according to the present invention is selected from the group consisting of 0.01-5% by weight of cationic fungicide, lauryl glucoside, cocamide DEA and polysorbate 20 based on the total weight of the composition. It is characterized by containing 4 to 10% by weight of the above nonionic surfactant. In addition, the composition further comprises 0.01 to 2.0% by weight of astringent.

이하, 본 발명을 보다 상세히 설명한다. Hereinafter, the present invention will be described in more detail.

본 발명의 구강용 조성물에서 양이온성 살균제로는 양이온성 암모늄염 살균제의 일종인 염화세틸피리디늄을 사용한다. 이는 구강내 유해균을 살균함으로써 치면 세균막의 형성을 막아 프라그를 억제하고, 치은염, 치주염을 비롯한 각종 잇몸질환에 탁월한 효과를 나타내어 구강제품에 많이 사용되고 있는 성분이다. 또한, 적절한 낮은 농도에서 사용되는 경우에 안전하다고 알려져 있으며, 주로 마우스워시와 같은 구강 위생용품에서 안전하게 사용되고 있다. As the cationic fungicide in the composition for oral cavity of the present invention, cetylpyridinium chloride which is a kind of cationic ammonium salt fungicide is used. It sterilizes harmful bacteria in the oral cavity, prevents plaque from forming on the surface of the plaque, inhibits plaque, and shows excellent effects on various gum diseases including gingivitis and periodontitis. In addition, it is known to be safe when used at a suitable low concentration, and mainly used in oral hygiene products such as mouse wash.

본 발명의 구강용 조성물에서는 상기 염화세틸피리디늄을 조성물 총 중량에 대하여 0.01~5 중량%의 양으로 함유한다. 이는 염화세틸피리디늄이 원료 자체의 쓴 맛이 있기 때문에 5 중량%를 초과하는 경우에는 조성물의 쓴 맛이 너무 강해서 사용하기 어렵고, 0.01 중량% 미만에서는 항균효과를 기대할 수 없기 때문이다.  In the composition for oral cavity of the present invention, the cetylpyridinium chloride is contained in an amount of 0.01 to 5% by weight based on the total weight of the composition. This is because when the cetylpyridinium chloride has a bitter taste of the raw material itself, when the content exceeds 5% by weight, the bitter taste of the composition is too strong to be used, and when less than 0.01% by weight, antibacterial effect cannot be expected.

본 발명의 구강용 조성물에서 함유되는 비이온성 계면할성제는 기포제로 상 기 양이온성 살균제의 항균활성이 저하되는 것을 방지하기 위해 배합되는 것이다. 상기 비이온성 계면활성제의 경우에는 양이온성 살균제와 최적의 효과를 발휘할 수 있는 성분으로서 라우릴 글루코시드, 코카마이드 DEA 및 폴리솔베이트 20으로 이루어진 군에서 선택된 1종 이상을 사용한다. 상기의 비이온성 계면활성제는 조성물 총 중량에 대하여 4~10 중량%로 함유하는데, 10 중량%를 초과하는 경우에는 피부 안전성에 문제가 생길 수 있고 4 중량% 미만에서는 항균효과를 기대하기가 어렵다.The nonionic interfacial agent contained in the composition for oral cavity of this invention is a foaming agent, and is mix | blended in order to prevent the antimicrobial activity of the said cationic fungicide from falling. In the case of the nonionic surfactant, at least one selected from the group consisting of lauryl glucoside, cocamide DEA, and polysorbate 20 is used as a component capable of exhibiting an optimal effect with the cationic fungicide. The nonionic surfactant is contained in an amount of 4 to 10% by weight based on the total weight of the composition. When the amount is more than 10% by weight, it may cause a problem in skin safety.

본 발명의 구강용 조성물에서 함유되는 수렴제는 효과를 연상하게 하는 연상 사용감을 부여하는 성분이다. 구체적인 예로는 염화아연, 산화아연, 황산아연, 글루콘산아연 등의 아연 화합물, 탄닌 등의 천연첨가물을 포함한다. 상기 수렴제는 조성물 총 중량에 대하여 0.01~2 중량%, 바람직하게는 0.1~1 중량%로 함유하며, 단독 또는 2종 이상 혼합하여 사용한다. The astringent agent contained in the composition for oral cavity of this invention is a component which gives the associative usability which associates an effect. Specific examples include zinc compounds such as zinc chloride, zinc oxide, zinc sulfate, zinc gluconate, and natural additives such as tannin. The astringent is contained in an amount of 0.01 to 2% by weight, preferably 0.1 to 1% by weight, based on the total weight of the composition, and used alone or in combination of two or more thereof.

본 발명에 의한 구강용 조성물은 그 제형에 있어서 특별히 한정되지 않으며, 구체적인 예를 들면, 치약, 구강용세정제, 구강 청정제 등의 제형을 가질 수 있다.The composition for oral cavity according to the present invention is not particularly limited in the formulation, and may have a formulation such as toothpaste, mouthwash, oral cleanser, for example.

본 발명의 구강용 조성물이 치약의 제형일 경우, 연마제, 습윤제, 기포제, 결합제, 감미제, pH조절제, 방부제, 약효성분, 향료, 증백제, 색소, 용제 등을 함유할 수 있다.When the composition for oral cavity of the present invention is a toothpaste formulation, it may contain abrasives, wetting agents, foaming agents, binders, sweeteners, pH adjusting agents, preservatives, active ingredients, flavoring agents, brighteners, pigments, solvents and the like.

상기 연마제 성분으로는 탄산칼슘, 침강 실리카, 수산화알루미늄, 인산수소칼슘, 불용성 메타인산나트륨 등이 있으며, 이들 연마제는 단독 또는 2종 이상 혼합하여 조성물 총 중량에 대하여 1~60 중량%, 바람직하게는 10~50 중량%로 사용한다.The abrasive components include calcium carbonate, precipitated silica, aluminum hydroxide, calcium hydrogen phosphate, insoluble sodium metaphosphate, and these abrasives are used alone or in combination of two or more thereof, preferably 1 to 60% by weight, based on the total weight of the composition. 10 to 50% by weight is used.

상기 습윤제 성분으로는 글리세린, 소르비톨액, 폴리에칠렌글리콜, 프로필렌글리콜 등이 있으며, 단독 또는 2종 이상 혼합하여 조성물 총 중량에 대하여 20~60 중량%로 사용한다. The humectant component includes glycerin, sorbitol solution, polyethylene glycol, propylene glycol, and the like, or may be used alone or in combination of two or more kinds at 20 to 60 wt% based on the total weight of the composition.

상기 결합제로는 하이드록시에틸셀룰로오스, 하이드록시프로필셀룰로오스, 잔탄검, 카라기난, 알긴산 나트륨 등을 단독 또는 2종 이상 혼합하여 조성물 총 중량에 대하여 0.1~5 중량%, 바람직하게는 0.1~2 중량%로 사용한다.  The binder may be hydroxyethyl cellulose, hydroxypropyl cellulose, xanthan gum, carrageenan, sodium alginate, or the like, alone or in combination of two or more, and 0.1 to 5% by weight, preferably 0.1 to 2% by weight, based on the total weight of the composition. use.

상기 감미제로는 삭카린나트륨, 아스파탐, 스테비오사이드, 자일리톨, 감초산 등을 단독 또는 2종 이상 혼합하여 조성물 총 중량에 대하여 0.05~5 중량%로 사용한다. As the sweetener, sodium saccharin, aspartame, stevioside, xylitol, and licorice acid are used alone or in combination of two or more, and are used in an amount of 0.05 to 5% by weight based on the total weight of the composition.

상기 pH조절제로는 인산나트륨, 인산이나트륨, 인산삼나트륨, 피로인산나트륨, 구연산나트륨, 구연산, 주석산 등이 있고, 상기 방부제로는 파라옥시안신향산메칠(메칠파라벤), 파라옥시안식향산프로필, 안식향산나트륨을 단독 또는 2종 이상 혼합하여 사용한다.The pH regulators include sodium phosphate, disodium phosphate, trisodium phosphate, sodium pyrophosphate, sodium citrate, citric acid, tartaric acid, and the like. The preservatives include paraoxyancin methyl (methylparaben), paraoxybenzoic acid propyl, and benzoic acid. Sodium is used alone or in combination of two or more.

상기 약효성분으로는 불화나트륨, 일불소인산나트륨, 불화주석, 클로로헥시딘, 알란토인 클로로히드록시알루미네이트, 아미노카프론산, 트리클로산, 염산피리독신, 초산토코페롤 등을 단독 또는 2종 이상 혼합하여 사용하고, 상기 향료로는 페퍼민트오일, 스피아민트오일, 멘톨, 아네톨 등을 적당량 혼합하여 사용하며, 상기 증백제로는 이산화티탄, 색소로는 식용색소, 용제로 정제수, 에탄올 등을 사용하여 통상의 치약 제조방법에 따라 제조한다. As the active ingredient, sodium fluoride, sodium monofluorophosphate, tin fluoride, chlorohexidine, allantoin chlorohydroxy aluminate, aminocaproic acid, triclosan, pyridoxine hydrochloride, tocopherol acetate and the like are used alone or in combination of two or more thereof. , As a fragrance, peppermint oil, spearmint oil, menthol, anetol and the like are mixed and used in an appropriate amount, and as a brightener, titanium dioxide, food coloring as a pigment, purified water as a solvent, ethanol and the like to prepare a general toothpaste It is prepared according to the method.

이하, 실시예 및 비교예를 들어 본 발명을 보다 상세히 설명하지만, 본 발명이 이들 예로만 한정되는 것은 아니다. Hereinafter, although an Example and a comparative example are given and this invention is demonstrated in detail, this invention is not limited only to these examples.

[시험예 1] 비이온 계면활성제간 항균력 비교 [Test Example 1] Comparison of antimicrobial activity between nonionic surfactants

비이온성 계면활성제간의 항균력을 비교하기 위해, 비이온성 계면활성제의 경우 주로 사용되는 목적에 따라 세제, 가용화제, 유화제로 사용되는 것 중에서 선택하였다. 각각 대표적으로 사용되는 시료로 세제에서는 라우릴 글루코시드(Lauryl glucoside, Cognis社)와 코카마이드(Cocamide) DEA(태동화학), 가용화제에서는 PEG-60 경화 피마자유(Hydrogenated castor oil, Nihon Emulsion CO.), 유화제에서는 폴리솔베이트(Polysorbate) 20(Uniquema社)을 선정하였다. In order to compare the antimicrobial activity between nonionic surfactants, nonionic surfactants were selected from among those used as detergents, solubilizers, and emulsifiers, depending on the purpose of use. Representative samples are Lauryl glucoside (Cognis) and Cocamide (DEA) in detergents, and PEG-60 hydrogenated castor oil (Nihon Emulsion CO. ), Polysorbate 20 (Uniquema) was selected as the emulsifier.

상기 원료를 표준 시험법(SOP) M-3 MIC Test 중 액체배지 희석법(Broth dilution method)으로 수행하였으며, 실험에 사용된 구강균은 스트렙토코커스 뮤탄스(S. mutans)균을 선정하였다. 먼저, 시료를 시험하고자 하는 액체 배지(1L중 송아지뇌(Calf brain) 7.7 g, 소심장(Beef Heart) 9.8 g, 프로테오스 펩톤(Proteose peptone) 10 g, 덱스트로오스(Dextrose) 2 g, 염화나트륨(Sodium chloride) 5 g, 제2 인산나트늄(Disodium phosphate) 2.5 g)를 준비한 후, 각 원료를 준비한 액체 배지에 잘 섞어 1~2% 최초 농도로 준비한 다음 동일 배지와 동량 섞어 1/2 (2-1) 희석액을 준비하였다. 같은 방법으로 2-2, 2-3, 2- 4 으로 계속 순차적 희석(serial dilution)을 시행하였다. 시료가 첨가된 여러 농도의 배지에 스트렙토코커스 뮤탄 스(S. mutans)균액을 접종하여 항온 배양기에서 배양하였다. 시험균의 배양온도와 배양기간은 각각 37℃에서 48시간 동안 배양하였다. 배양 후 액체 배지의 현탁도로 미생물의 성장이 저해된 최소 농도(MIC)를 결정하고, 현탁도로 비교가 어려운 경우는 현미경으로 미생물의 생존여부를 확인하였다. 그 결과를 하기 표 1에 나타내었다. The raw material was performed by the broth dilution method in the standard test method (SOP) M-3 MIC Test, and the oral bacteria used in the experiment were selected from Streptococcus mutans . First, the liquid medium (1 g of Calf brain, 9.8 g of Beef Heart), 10 g of Proteose peptone, 2 g of Dextrose, After preparing 5 g of sodium chloride and 2.5 g of disodium phosphate, mix each raw material well to the prepared liquid medium, prepare 1 ~ 2% initial concentration, and mix the same amount with the same medium 1/2 (2 -1) of diluent was prepared. Continue was performed sequentially diluted (serial dilution) to 4 - the same method 2-2, 2-3, 2. S. mutans bacteria were inoculated into various concentrations of the medium to which the samples were added and cultured in an incubator. The culture temperature and incubation period of the test bacteria were incubated for 48 hours at 37 ℃. The minimum concentration (MIC) that inhibited the growth of microorganisms was determined by the suspension of the liquid medium after the culture, and in the case of difficulty in comparison with the suspension, the survival of the microorganisms was confirmed under a microscope. The results are shown in Table 1 below.

각 시료간 스트렙토코커스 뮤탄스 균에 대한 MIC 결과MIC results for Streptococcus mutans bacteria between samples 시료sample 라우릴 글루코시드Lauryl Glucoside 코카마이드 DEACocamide DEA PEG-60 경화피마자유PEG-60 Cured Castor Oil 폴리솔베이트 20Polysorbate 20 MICMIC <78.125ppm<78.125 ppm <78.125ppm<78.125 ppm >8%> 8% >8%> 8%

 

상기 표 1의 결과로부터, 세제로 사용되는 라우릴 글루코시드와 코카마이드 DEA의 경우가 상당히 높은 항균력을 나타내는 반면, 가용화제와 유화제로 사용되어지는 PEG-60 경화피마자유와 폴리솔베이트 20은 항균력이 없는 것을 확인하였다. From the results of Table 1, while lauryl glucoside and cocamide DEA used as detergents exhibited a very high antimicrobial activity, PEG-60 hardened castor oil and polysorbate 20 used as solubilizers and emulsifiers had antibacterial activity. It was confirmed that there was no.

[실시예 1~6 및 비교예 1~7][Examples 1-6 and Comparative Examples 1-7]

하기 표 2의 조성으로 실시예 1~6 및 비교예 1~7의 구강용 조성물을 제조하였다. To oral compositions of Examples 1 to 6 and Comparative Examples 1 to 7 were prepared by the composition of Table 2 below.

구분division 성분명 (함량; 중량%)Ingredient Name (Content; Weight%) 실시예Example 비교예Comparative example 1One 22 33 44 55 66 1One 22 33 44 55 66 77 연마제abrasive 인산수소칼슘Calcium hydrogen phosphate 3030 3030 3030 3030 3030 3030 3030 3030 3030 3030 3030 3030 3030 약효성분Active ingredient 일불소인산나트륨Sodium monofluorophosphate 0.760.76 0.760.76 0.760.76 0.760.76 0.760.76 0.760.76 0.760.76 0.760.76 0.760.76 0.760.76 0.760.76 0.760.76 0.760.76 약효성분Active ingredient 염화세틸피리디늄Cetylpyridinium Chloride 0.050.05 0.050.05 0.050.05 0.050.05 0.050.05 0.050.05 0.050.05 0.050.05 0.050.05 0.050.05 0.050.05 0.050.05 0.050.05 습윤제Humectant 소르비톨액Sorbitol solution 2020 2020 2020 2020 2020 2020 2020 2020 2020 2020 2020 2020 2020 결합제Binder 하이드록시에칠셀룰로오스Hydroxyethyl Cellulose 2.02.0 2.02.0 2.02.0 2.02.0 2.02.0 2.02.0 2.02.0 2.02.0 2.02.0 2.02.0 2.02.0 2.02.0 2.02.0 방부제antiseptic 메틸파라벤Methylparaben 0.20.2 0.20.2 0.20.2 0.20.2 0.20.2 0.20.2 0.20.2 0.20.2 0.20.2 0.20.2 0.20.2 0.20.2 0.20.2 약효성분Active ingredient 초산토코페롤Tocopherol Acetate 0.20.2 0.20.2 0.20.2 0.20.2 0.20.2 0.20.2 0.20.2 0.20.2 0.20.2 0.20.2 0.20.2 0.20.2 0.20.2 향료Spices 조합향료Combination spices 1.01.0 1.01.0 1.01.0 1.01.0 1.01.0 1.01.0 1.01.0 1.01.0 1.01.0 1.01.0 1.01.0 1.01.0 1.01.0 감미제Sweetener 삭카린 나트륨Zaccarin Sodium 0.30.3 0.30.3 0.30.3 0.30.3 0.30.3 0.30.3 0.30.3 0.30.3 0.30.3 0.30.3 0.30.3 0.30.3 0.30.3 pH조절제pH regulator 구연산 나트륨Sodium citrate 0.20.2 0.30.3 0.20.2 0.30.3 0.20.2 0.30.3 0.10.1 0.10.1 0.10.1 0.20.2 0.30.3 0.10.1 0.10.1 증백제Brightener 이산화티탄Titanium dioxide 0.30.3 0.30.3 0.30.3 0.30.3 0.30.3 0.30.3 0.30.3 0.30.3 0.30.3 0.30.3 0.30.3 0.30.3 0.30.3 기포제Foam 라우릴 글루코시드Lauryl Glucoside 44 88 -- -- -- -- -- 1One -- -- -- -- -- 기포제Foam PEG-60 경화피마자유PEG-60 Cured Castor Oil -- -- -- -- -- -- -- -- 1One 44 88 -- -- 기포제Foam 폴리솔베이트 20Polysorbate 20 -- -- 44 88 -- -- -- -- -- -- 1One -- 기포제Foam 코카마이드 DEACocamide DEA -- -- -- -- 44 88 -- -- -- -- -- 1One 용제solvent 정제수Purified water 잔량Remaining amount 잔량Remaining amount 잔량Remaining amount 잔량Remaining amount 잔량Remaining amount 잔량Remaining amount 잔량Remaining amount 잔량Remaining amount 잔량Remaining amount 잔량Remaining amount 잔량Remaining amount 잔량Remaining amount 잔량Remaining amount

[시험예 2] 비이온 계면활성제의 농도별 항균력 비교Test Example 2 Comparison of Antimicrobial Activity by Concentration of Nonionic Surfactant

상기 실시예 1~6 및 비교예 1~7의 구강용 조성물을 상기 시험예 1의 액체배지 희석법으로 측정하였다. 그 결과를 하기 표 3에 나타내었다. The oral compositions of Examples 1 to 6 and Comparative Examples 1 to 7 were measured by the liquid medium dilution method of Test Example 1. The results are shown in Table 3 below.

실시예 1~6 및 비교예 1~7의 MIC 비교MIC comparison of Examples 1-6 and Comparative Examples 1-7 실시예Example 비교예Comparative example 1One 22 33 44 55 66 1One 22 33 44 55 66 77 MIC MIC 625625 312.5312.5 625625 625625 312.5312.5 312.5312.5 12501250 12501250 12501250 12501250 12501250 12501250 12501250

상기 표 3의 결과로부터, 구강용 조성물에서 사용된 비이온성 계면활성제가 양이온성 살균제의 항균력을 떨어뜨리지 않는 것을 확인하였다. 그 중에서도 라우릴 글루코시드와 코카마이드 DEA의 경우는 1 중량% 농도까지는 항균력의 변화가 없었으나, 4 중량% 이상을 배합하면서 급격히 항균력이 높아지는 것으로 확인하였다. From the results of Table 3, it was confirmed that the nonionic surfactant used in the composition for oral cavity does not degrade the antimicrobial activity of the cationic fungicide. Among them, in the case of lauryl glucoside and cocamide DEA, there was no change in the antimicrobial activity up to 1 wt% concentration, but it was confirmed that the antimicrobial activity rapidly increased while blending 4 wt% or more.

코카마이드 DEA의 경우는 4 중량%를 배합한 결과와 8 중량%를 배합한 결과가 동일하였으며, 라우릴 글루코시드의 경우는 8 중량%를 배합한 결과가 4 중량%를 배합한 결과보다 더 높은 항균력 상승을 나타내었다. 한편, PEG-60 경화 피마자유는 원료 자체의 항균력이 없었으므로 8 중량%를 배합하여도 항균력의 변화가 없음을 확인하였다. In the case of cocamide DEA, the result of blending 4% by weight was the same as the result of blending 8% by weight. For lauryl glucoside, the result of blending 8% by weight was higher than the result of blending 4% by weight. An increase in antimicrobial activity was shown. On the other hand, since PEG-60 cured castor oil did not have the antibacterial activity of the raw material itself, it was confirmed that there was no change in the antibacterial activity even when 8% by weight was blended.

그러나, 폴리솔베이트 20의 경우는 원료 실험시 항균력을 나타내지 않았으나, 4 중량%이상을 배합했을 경우에 항균력이 높아지는 결과를 확인하였다. 상기의 결과로서 자체 항균력을 가진 라우릴 글루코시드와 코카마이드 DEA의 경우는 배합농도가 높아질수록 항균력도 높아짐을 확인할 수 있었으며, 폴리솔베이트 20의 경우는 자체 항균력이 없음에도 4%이상 배합했을 경우 항균제의 항균력을 증대시키는 것을 확인할 수 있었다. However, polysorbate 20 did not show antimicrobial activity during raw material experiments, but when 4 wt% or more were added, the antimicrobial activity was confirmed. As a result, in case of lauryl glucoside and cocamide DEA having antimicrobial activity, it was confirmed that the antimicrobial activity was increased as the concentration was increased. It was confirmed that the antimicrobial activity of the antimicrobial agent was increased.

[실시예 7] Example 7

하기 표 4의 조성으로 실시예 7의 구강용 조성물을 제조하였다. To oral composition of Example 7 was prepared in the composition of Table 4.

구분division 성분명(함량:중량%)Ingredient name (content: weight%) 실시예 7Example 7 연마제abrasive 인산수소칼슘Calcium hydrogen phosphate 3030 약효성분Active ingredient 일불소인산나트륨Sodium monofluorophosphate 0.760.76 약효성분Active ingredient 염화세틸피리디늄Cetylpyridinium Chloride 0.050.05 습윤제Humectant 소르비톨액Sorbitol solution 2020 결합제Binder 하이드록시에칠셀룰로오스Hydroxyethyl Cellulose 2.02.0 방부제antiseptic 메틸파라벤Methylparaben 0.20.2 약효성분Active ingredient 초산토코페롤Tocopherol Acetate 0.20.2 향료Spices 조합향료Combination spices 1.01.0 감미제Sweetener 삭카린 나트륨Zaccarin Sodium 0.30.3 pH조절제pH regulator 구연산 나트륨Sodium citrate 0.10.1 증백제Brightener 이산화티탄Titanium dioxide 0.30.3 기포제Foam 라우릴 글루코시드Lauryl Glucoside 44 수렴제Astringent 염화 아연Zinc chloride 0.50.5 용제solvent 정제수Purified water 잔량Remaining amount

[시험예 3] 연상효능 사용감에 대한 관능 평가Test Example 3 Sensory Evaluation on Associative Efficacy

상기 실시예 7 및 실시예 1의 구강용 조성물을 일정기간 사용한 후, 그 효능을 연상하게끔 하는 사용감을 느끼는 지에 대해 관능평가를 실시하였다. 비교적 동일한 환경에 있는 피검자 40명을 대상으로 실시하였으며, 두 그룹으로 나누어 한 그룹은 실시예 1의 일반 구강용 조성물을 사용하였고 다른 한 그룹은 실시예 7의 효능연상 사용감을 줄 수 있는 원료를 배합한 구강용 조성물을 사용하였다. 1일 3회, 2주간 사용하도록 하였으며, 1회 사용량은 2g정도씩 적용하도록 하였다. 단일 맹검법을 적용하였으며, 양치 시 잇몸질환 예방치약의 느낌이 드는 지와 양치 후 잇몸질환 예방에 효과가 있는 것으로 생각되는지, 그리고 양치 후 잇몸에 탄력감이 느껴지는 지에 대해서 5점 척도의 소비자 품평 조사를 이용하였다. 그 결과를 하기 표 5에 나타내었다. After using the composition for oral cavity of Example 7 and Example 1 for a period of time, the sensory evaluation was carried out to feel the feeling of reminiscent of the efficacy. Forty subjects in a relatively identical environment were administered to two groups, divided into two groups, one group used the general oral composition of Example 1, and the other group contained a raw material that can give a feeling of efficacy in Example 7. One oral composition was used. Three times a day, two weeks were to be used, once the amount was applied to about 2g. A single blind method was applied, and a five-point consumer review survey was conducted to determine whether you felt toothpaste-preventive toothpaste when you brushed your teeth, whether you think it is effective in preventing gum disease after brushing, and whether you feel elasticity in your gums after brushing your teeth. Was used. The results are shown in Table 5 below.

그룹group 양치시 잇몸질환 예방치약의 느낌Feeling of gum disease prevention toothpaste when brushing teeth 양치 후 잇몸질환 예방치약의 효능 인지Recognition of the efficacy of toothpaste prevention gum after brushing teeth 양치 후 잇몸탄력감Gum elasticity after brushing 실시예 7Example 7 3.53.5 3.63.6 3.53.5 실시예 1Example 1 2.92.9 2.82.8 2.62.6

상기 표 5의 결과로부터, 두 그룹간 사용감과 기포력 등 구강용 조성물의 기본 속성에 해당하는 평가부문은 동일한 결과를 나타내었으나, 잇몸질환 효능이 연상이 되는 사용감을 느낄 수 있는지에 대한 항목에 대해서는 효능 연상 사용감을 줄 수 있는 원료를 배합한 실시예 7이 실시예 1의 제품군보다 양치 시와 양치 후 각각 0.6, 0.8점 정도의 차이로 그러한 사용감을 느낀다는 응답이 더 많았다. From the results of Table 5, the evaluation section corresponding to the basic properties of the composition for oral cavity, such as feeling and foaming force between the two groups showed the same result, but for the item about whether the feeling of gum disease can be reminiscent of feeling Efficacy in Example 7, which contains a raw material that can give a feeling of associative feeling was more than the product of Example 1 in the case of brushing and after brushing, with a difference of about 0.6, 0.8 points, respectively, the response was more.

또한, 양치 후 잇몸탄력감을 느끼는 정도에 대해서도 0.9점 차이로 실시예에서 더욱 높게 잇몸탄력감을 느낄 수 있었음을 알 수 있었다. 실험의 결과로서 실시예 7이 실시예 1에 비해 효능을 연상할 수 있는 사용감을 고객이 더 많이 인지함을 확인할 수 있었다.In addition, the degree of feeling of gum elasticity after brushing was 0.9 points, it can be seen that the gum elasticity was felt higher in the embodiment. As a result of the experiment, it was confirmed that the customer perceived the feeling that Example 7 was reminiscent of efficacy compared to Example 1.

이상에서 설명한 바와 같이, 본 발명에 따른 구강용 조성물은 배합하는 비이온계면활성제의 종류 및 함량에 따라 단순히 살균제를 배합한 경우보다 매우 뛰어난 항균력을 나타냄을 확인할 수 있었으며, 잇몸수렴감과 탄력감을 제공함으로써 고객이 그 효능을 연상할 수 있는 제품 사용감을 제공할 수 있다.As described above, the composition for oral cavity according to the present invention was found to exhibit a very good antimicrobial activity than the case of simply compounding a fungicide according to the type and content of the non-ionic surfactant to be blended, by providing a feeling of gum convergence and elasticity It can provide a feeling of use of the product that the customer can associate with the efficacy.

Claims (5)

조성물 총 중량에 대하여 양이온성 살균제 0.01~5 중량%, 라우릴 글루코시드, 코카마이드 DEA 및 폴리솔베이트 20으로 이루어진 군에서 선택된 1종 이상의 비이온성 계면활성제 4~10 중량%을 함유하는 것을 특징으로 하는 항균용 구강용 조성물. 0.01 to 5% by weight of cationic fungicide, lauryl glucoside, cocamide DEA and polysorbate 20, based on the total weight of the composition, characterized in that it contains 4 to 10% by weight of at least one nonionic surfactant selected from the group consisting of Oral composition for antibacterial. 제 1항에 있어서, 상기 양이온성 살균제는 염화세틸피리디늄임을 특징으로 하는 구강용 조성물.The oral composition according to claim 1, wherein the cationic fungicide is cetylpyridinium chloride. 제 1항에 있어서, 상기 조성물에 조성물 총 중량에 대하여 수렴제 0.01~2 중량%를 더 함유함을 특징으로 하는 구강용 조성물.The composition for oral cavity according to claim 1, wherein the composition further contains 0.01 to 2% by weight of astringent based on the total weight of the composition.   제 3항에 있어서, 상기 수렴제는 염화아연, 산화아연, 황산아연, 및 글루콘산아연의 아연 화합물, 및 탄닌의 천연첨가물로 이루어진 군에서 선택된 1종 이상임을 특징으로 하는 구강용 조성물. 4. The composition for oral cavity according to claim 3, wherein the astringent is at least one selected from the group consisting of zinc chloride, zinc oxide, zinc sulfate, zinc gluconate, zinc compounds, and tannins.   제 3항 또는 제 4항에 있어서, 상기 조성물은 잇몸 수렴감과 탄력감을 제공하는 것을 특징으로 하는 구강용 조성물.The composition for oral cavity according to claim 3 or 4, wherein the composition provides a feeling of gum convergence and elasticity.
KR1020060003151A 2006-01-11 2006-01-11 Oral composition having a good antibacterial effect KR100659139B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR1020060003151A KR100659139B1 (en) 2006-01-11 2006-01-11 Oral composition having a good antibacterial effect

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
KR1020060003151A KR100659139B1 (en) 2006-01-11 2006-01-11 Oral composition having a good antibacterial effect

Publications (1)

Publication Number Publication Date
KR100659139B1 true KR100659139B1 (en) 2006-12-19

Family

ID=37814816

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1020060003151A KR100659139B1 (en) 2006-01-11 2006-01-11 Oral composition having a good antibacterial effect

Country Status (1)

Country Link
KR (1) KR100659139B1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102469323B1 (en) * 2022-02-09 2022-11-22 주식회사 고차원 Liquid composition for gargle containing clove oil

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS56139423A (en) 1980-04-02 1981-10-30 Toyo Seiyaku Kasei Kk Hemostatic agent for dental oral use
KR960000200A (en) * 1994-06-29 1996-01-25 다카하시 미치나오 Oral Composition
US5948390A (en) 1997-08-25 1999-09-07 Pfizer Inc. Stable zinc/citrate/CPC oral rinse formulations
US6086856A (en) 1994-03-28 2000-07-11 Oralcare Systems, Inc. System for delivering foamed oral hygiene compositions
KR20020013959A (en) * 1999-07-16 2002-02-21 고든 라이트 Titanium Derived Compounds, Preparation and Use Thereof
US6723305B2 (en) 2002-03-04 2004-04-20 Colgate Palmolive Company Anti-microbial breath freshening mouthrinse
KR20050013204A (en) * 2002-06-07 2005-02-03 산스타 가부시끼 가이샤 Compositions for oral cavity

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS56139423A (en) 1980-04-02 1981-10-30 Toyo Seiyaku Kasei Kk Hemostatic agent for dental oral use
US6086856A (en) 1994-03-28 2000-07-11 Oralcare Systems, Inc. System for delivering foamed oral hygiene compositions
KR960000200A (en) * 1994-06-29 1996-01-25 다카하시 미치나오 Oral Composition
US5948390A (en) 1997-08-25 1999-09-07 Pfizer Inc. Stable zinc/citrate/CPC oral rinse formulations
KR20020013959A (en) * 1999-07-16 2002-02-21 고든 라이트 Titanium Derived Compounds, Preparation and Use Thereof
US6723305B2 (en) 2002-03-04 2004-04-20 Colgate Palmolive Company Anti-microbial breath freshening mouthrinse
KR20050013204A (en) * 2002-06-07 2005-02-03 산스타 가부시끼 가이샤 Compositions for oral cavity

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102469323B1 (en) * 2022-02-09 2022-11-22 주식회사 고차원 Liquid composition for gargle containing clove oil

Similar Documents

Publication Publication Date Title
AU2006320846B2 (en) Vehicles for oral care with Magnolia Bark Extract
RU2535010C2 (en) Antibacterial composition, containing 4-isopropyl-3-methylphenol and zinc ions
CA2125957C (en) Dentifrice compositions
KR102401341B1 (en) Improved Mouthwash Preparation
JP5597970B2 (en) Dentifrice composition
EP2648681B1 (en) An oral care composition
US11471394B2 (en) Oral care compositions containing deoxy sugar antimetabolites
WO1992008441A1 (en) Improved anti-plaque compositions comprising a combination of morpholinoamino alcohol and metal salts
KR101780837B1 (en) Emulsion-type liquid composition for oral cavity, and process for production thereof
KR100637653B1 (en) Oral composition for inhibiting the halitosis
KR100659139B1 (en) Oral composition having a good antibacterial effect
CN111050747B (en) Dentifrice composition
JP7159265B2 (en) Anti-periodontal disease composition
KR102212634B1 (en) Oral composition
KR101818211B1 (en) Composition for prevention or treatment of oral disease comprising Arctill fructus Extract
KR102550067B1 (en) Oral Composition having policresulen and fluorine compound
JP2004026724A (en) Composition for oral cavity
EP3808327A1 (en) Oral care compositon
KR20180081271A (en) Oral composition for removing dental plaque containing alkyl glucoside
KR20070102184A (en) Oral composition with improved antimicrobial property
KR20170120404A (en) Composition for prevention or treatment of oral disease comprising 2-methoxycinnamaldehyde
KR20170120408A (en) Composition for prevention or treatment of oral disease comprising Qucercetin 3-glucoside
KR20170120416A (en) Composition for prevention or treatment of oral disease comprising Matairesinol
KR20170120399A (en) Composition for prevention or treatment of oral disease comprising Genistein
KR20170120414A (en) Composition for prevention or treatment of oral disease comprising Esculetin

Legal Events

Date Code Title Description
A201 Request for examination
N231 Notification of change of applicant
E701 Decision to grant or registration of patent right
GRNT Written decision to grant
FPAY Annual fee payment

Payment date: 20121127

Year of fee payment: 7

FPAY Annual fee payment

Payment date: 20131121

Year of fee payment: 8

LAPS Lapse due to unpaid annual fee