KR940006065B1 - Dentifrice compositions for using carious tooth tooth root disease - Google Patents
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Abstract
Description
[발명의 명칭][Name of invention]
충치 및 치주질환에 유효한 치약 조성물Toothpaste composition effective for caries and periodontal disease
[발명의 상세한 설명]Detailed description of the invention
본 발명은 몰약(또는 Myrrh Oil), 상백피, 승마 및 녹차로부터 얻은 추출물을 배합한 치약 조성물에 관한 것이며, 보다 상세하게는 충치원인균<Streptococcus mutans(ATCC 27607, ATCC 27351, ATCC 25175, NRRL 10449), Streptococcus sanguis, Streptococcus salivarius> 및 치주병원인균(Actinomyces viscous, Actinomyces naeslundi, Bacteroides gingvalis, Bacteroides forsythus, Bacteroides intermedius)에 대하여 항균작용을 가지며, 충치원인균의 균제외 효소 글루코실트랜스퍼레이즈(Glucosyltransferase ; GTase)의 활성을 억제함으로서 프라그형성에 의한 충치 및 치주질환을 예방하기 위한 구강용 조성물, 특히 치약 조성물에 관한 것이다.The present invention relates to a toothpaste composition comprising a extract from myrrh oil (or Myrrh Oil), lettuce, horse riding and green tea, and more specifically, the causative agent of Streptococcus mutans (ATCC 27607, ATCC 27351, ATCC 25175, NRRL 10449), Streptococcus sanguis, Streptococcus salivarius> and actinomycetes viscous, Actinomyces naeslundi, Bacteroides gingvalis, Bacteroides forsythus, Bacteroides intermedius, and antibacterial glucosyl glucose glucosyltransase (Glucose gluase) It relates to a composition for oral cavity, in particular toothpaste composition for preventing tooth decay and periodontal disease caused by plaque formation by inhibiting.
일반적으로 충치는 음식물에 함유되어 있는 설탕이 여러 종류의 구강내 세균에 의해 작용을 받아 점착성 다당류를 생성하게 되어 각 세균이 치아표면에 부착되기 쉽게 되고, 세균이 모인 치태를 형성하며, 여기에 모인 세균은 당류를 분해하여 산을 생성시키고, 이 산이 치아의 에나멜 표면을 탈회시켜 충치를 진행시킨다. 치태가 한층 더 진행되어 치석으로 발전하면 치육염, 치은염, 치조농루의 치주질환을 유발하게 된다.In general, tooth decay is caused by various kinds of oral bacteria to produce cohesive polysaccharides, so that each bacteria easily adheres to the tooth surface, and bacteria form the plaque, Bacteria break down sugars to produce acids, which demineralize the tooth's enamel surface to advance tooth decay. As plaque further progresses to calculus, it causes gingivitis, gingivitis, and periodontal disease of alveolar pylori.
이러한 구강질환을 예방하기 위한 방법으로 항생제, 살균제등을 사용하는 경우 여러가지 부작용이 있는 것으로 보고되어 있다<J. Dent. Res., 25, 441(1946), J. Dent. Res., 31, 421(1966), J. Oral Ther. Pharmacol., 3, 157(1966), J. Am. Dent. Ass., 87 1006(1973)>.It is reported that there are various side effects when using antibiotics, fungicides, etc. as a method for preventing such oral diseases. Dent. Res., 25, 441 (1946), J. Dent. Res., 31, 421 (1966), J. Oral Ther. Pharmacol., 3, 157 (1966), J. Am. Dent. Ass., 87 1006 (1973)>.
이에 본 발명자는 각종 식물추출물의 항균 효과 및 프라그 형성 억제 효과에 대하여 탐색한 결과, 몰약, 상백피, 승마, 녹차의 혼합식물추출물이 충치원인균 및 치주질환원인균에 대해 기존의 식물추출물들<JP 84-134729(A)(감초, 상백피), JP 88-253019(A)(고추나물), JP 83-39614(A)(살비아, 로즈마리)>보다 뛰어난 항균효과를 나타내었고, 프라그형성에 중요한 역할을 하는 S. mutans의 균체외 효소 GTase에 대해 기존의 식물추출물들<JP 평1-190624(A)(녹차, 우롱차, 홍차), JP 87-48616(A)(박하, 로즈마리), JP 87-58331(B2)(세네가, 개암나무)보다 더 우수한 GTase 저해효과를 갖고 있는 것을 확인하였다. 이러한 혼합식물 추출물들을 각종 구강용 조성물에 배합할 경우에도 충치 및 치주병 원인균에 대한 항균효과와 GTase 저해효과를 나타내어 충치 및 치주질환예방을 목적으로 하는 구강용 조성물을 얻을 수 있음을 발견하고 본 발명을 완성하였다.Therefore, the present inventors have investigated the antibacterial and plaque formation inhibitory effects of various plant extracts. As a result, the mixed plant extracts of myrrh, baekryepi, horseback riding, and green tea are known to be used as the conventional plant extracts against caries and periodontal disease. 134729 (A) (Liquorice, Morus bark), JP 88-253019 (A) (Pepper Sprouts), JP 83-39614 (A) (Salvia, Rosemary)> showed superior antibacterial effects and played an important role in plaque formation. Existing Plant Extracts for the Extracellular Enzyme GTase of S. mutans <JP Hei 1-90624 (A) (Green Tea, Oolong Tea, Black Tea), JP 87-48616 (A) (Mint, Rosemary), JP 87- It was confirmed that 58331 (B 2 ) (Senega, hazel) has a superior GTase inhibitory effect. When the mixed plant extracts are formulated in various oral compositions, they show antimicrobial and GTase inhibitory effects on caries and periodontal disease-causing bacteria, thereby finding that oral compositions for the purpose of preventing caries and periodontal disease can be obtained. Was completed.
몰약은 Commphora molmol Engl. 및 동속식물(감람나무과 Burseraceae)의 껍질부위의 상처에서 얻은 고무수지로 진통, 방부작용이 있어 아구창, 치은염 및 구강세제에 사용되어 왔고, 상백피는 Morus alba L. 또는 동속식물(뽕나무과 Moraceae)의 뿌리껍질로 혈압강하, 소염, 치육종통작용이 있다. 승마는 Cimicifuga heracleifolia komarov 또는 그 밖의 동속식물(미나리아재비과 Ranunculaceae)의 뿌리줄기로 진통 및 해열작용이 있어서 치통 및 구강내의 염증에 대한 한방의학서 처방에 널리 사용되어 왔다. 녹차는 Camellia sinensis 및 동속식물의 잎으로 고대로부터 기호품으로 음용되어 왔으며, 동경 의대 치과대학 마사오 교수는 국민학교 아동 300명에 대하여 급식 후 차를 마시게 한 아동들이 차를 마시지 않은 아동들에 비해 충치발생율이 적게 나타났다는 차와 충치와의 관계를 암시하는 보고를 발표하여 차가 충치균에 대한 항균작용이 있음을 증명하였고<Fragrance J., p48(1990)>, 차에는 입안의 구취를 제거하는 효과도 있는 것으로 보고되어 있다.<Fragrance J., p37(1990)>Myrrh is Commphora molmol Engl. It is a rubber resin obtained from wounds of the bark of the same plant (Oliveaceae Burseraceae). It has been used for thrush, gingivitis and oral detergent due to its analgesic and antiseptic effect, and the cedar is the root of Morus alba L. or the same plant (Moraceae). The shell has a blood pressure drop, anti-inflammatory, and tooth pain. Horseback riding is a root stem of Cimicifuga heracleifolia komarov or other similar plants (Muniaceae, Ranunculaceae). It has been widely used in prescription of Chinese medicine for toothache and oral inflammation due to analgesic and antipyretic effects. Green tea has been used as a favorite product since ancient times as a leaf of Camellia sinensis and the same plant. Professor Masao of the Tokyo University School of Dentistry has taught that 300 children of the national school had children who had tea after feeding, compared to children who did not drink tea. A report suggesting the relationship between car and tooth decay has been published, demonstrating that tea has antimicrobial activity against caries (Fragrance J., p48 (1990)), and tea also has the effect of eliminating bad breath in the mouth. Fragrance J., p 37 (1990).
이하 본 발명을 상세히 설명하면 다음과 같다.Hereinafter, the present invention will be described in detail.
본 발명은 치약, 구강세정제, 캔디 및 츄잉껌등 각종 구강용 조성물중에 몰약(또는 Myrrh Oil), 상백피, 승마, 녹차로부터 얻은 혼합추출물들을 배합하는 것에 관한 것이며, 특히 충치 및 치주질환에 유효한 치약 조성물에 관한 것이다. 상기 식물의 추출시 사용한 용매로는 물, 메탄올, 에탄올, 아세톤등의 극성 용매로 식물원료에 대해 2-10배로 추출 용매를 가하여 침적 추출한후, 여과액을 농축 건조하여 농축물을 얻었다. 그리고 이 농축물을 적당한 용제로 용해시킨 현탁액을 이용할 수도 있다. 이렇게 하여 얻어진 혼합식물추출물들을 각종 형태의 제품에 응용하여 구강내에 적용하면 충치 및 치주질환의 예방이 가능하게 된다. 이 식물추출물액의 구강용 조성물에의 배합량은 각각 전체의 0.001-10%(w/w), 특히 0.01-3%(w/w)로 하는 것이 좋으며, 응용할 수 있는 구강용 조성물로는 각종 치약, 구강세정제, 캔디류 및 츄잉껌이 될 수 있다.The present invention relates to the combination of extracts derived from myrrh oil (or Myrrh Oil), baekryepi, horse riding, green tea in various oral compositions such as toothpaste, mouthwash, candy and chewing gum, and particularly effective in toothpaste compositions effective against caries and periodontal disease. It is about. The solvent used for the extraction of the plant was extracted by adding the extraction solvent 2-10 times with respect to the plant material with a polar solvent such as water, methanol, ethanol, acetone, etc., and the filtrate was concentrated to dryness to obtain a concentrate. And the suspension which melt | dissolved this concentrate with the suitable solvent can also be used. The mixed plant extracts thus obtained are applied to various types of products and applied in the oral cavity to prevent tooth decay and periodontal disease. It is preferable that the compounding amount of the plant extract solution to the oral composition is 0.001-10% (w / w), especially 0.01-3% (w / w), of the total, and various toothpastes are applicable as an oral composition that can be applied. , Mouthwashes, candies and chewing gum.
본 발명을 실시하기 위한 각종 구강용 조성물은 그 종류에 따라 적당한 성분을 사용하여 제조해야 하는데, 예를들면 치약의 경우에는 제2인산칼슘, 탄산칼슘, 피로인산칼슘, 메타인산칼슘, 실리카류, 알루미늄실리케이트, 수산화알루미늄등의 연마제(본품 10-60%), 카르복시메틸셀룰로오스, 하이드록시메틸셀룰로오스, 알긴산염, 카라기난, 아라비아껌, 폴리비닐알콜등의 접증제(0.4-5%), 폴리에틸렌글리콜류, 솔비톨, 글리세린 폴리비닐알콜 등의 습윤제, 라우릴황산나트륨, 소디움라우릴사르코시네이트, 모노글리세라이드설페이트, 자당지방산에스테르, 폴리옥시에틸렌경화피마자유, 폴리옥시에틸렌폴리옥시프로필렌공중합체, 폴리옥시에틸렌소르비탄지방산에스테르등의 발포제외에 향료, 사카린, 스테비오사이드 등의 감미제, 방부제등의 성분을 물과 혼합하여 통상의 치약 제조방법에 따라 제조한다. 본 발명에 의하여 식물추출물을 첨가하여 제조한 치약에는 불화나트륨, 모노플로로인산나트륨, 소금, 알란토인, 피로인산염, 아미노카로익산, 비타민류, 동크로로필나트륨, 트라네사믹산, 염화아연, 트리클로산, 염화세틸피리디움, 비닐메틸에테르/말레인산 공중합체등 치약에 통상 사용되고 있는 각종 유효성분의 첨가도 가능하다. 또 구강세정제, 캔디류 및 츄잉껌등의 제품도 그 제법에 따라 각종 성분을 적당히 배합하여 제조가 가능하다.Various oral compositions for carrying out the present invention should be prepared using suitable ingredients according to the type thereof, for example, in the case of toothpaste, dicalcium phosphate, calcium carbonate, calcium pyrophosphate, calcium metaphosphate, silicas, Abrasives (0.4-10%) such as aluminum silicate, aluminum hydroxide, carboxymethyl cellulose, hydroxymethyl cellulose, alginate, carrageenan, gum gum, polyvinyl alcohol, etc. Humectants such as sorbitol, glycerin polyvinyl alcohol, sodium lauryl sulfate, sodium lauryl sarcosinate, monoglyceride sulfate, sucrose fatty acid ester, polyoxyethylene hardened castor oil, polyoxyethylene polyoxypropylene copolymer, polyoxyethylene In addition to foaming agents such as sorbitan fatty acid esters, water, ingredients such as flavoring agents, saccharin, stevioside, sweeteners, and preservatives Mixture will be prepared according to conventional toothpaste preparation. Toothpaste prepared by the addition of plant extracts according to the present invention include sodium fluoride, sodium monofluorophosphate, salt, allantoin, pyrophosphate, aminocaroroic acid, vitamins, doncrorophyll sodium, tranesamic acid, zinc chloride, triclosan Also, various active ingredients commonly used in toothpaste, such as cetylpyridium chloride and vinyl methyl ether / maleic acid copolymer, can be added. In addition, products such as mouthwashes, candies and chewing gum can be prepared by appropriately blending various ingredients according to the manufacturing method.
본 발명의 추출물 제조 실시예를 나타내면 다음과 같다.Representative examples of extract preparation of the present invention are as follows.
[추출물 제조 실시예]Extract Preparation Example
건조 생약재(녹차)를 분쇄한 것 50g에 70% 에탄올 500ml를 가하여 실온에서 10일간 침적하여 추출여과한 후, 그 여과액을 완전히 감압농축하여 농축물을 20.02g 얻었다. 그 밖의 건조 생약제(몰약, 상백피, 승마)를 상기의 기술된 방법에 따라 추출하여 각각 6.1g, 5.2g, 4.8g의 농축물을 얻었다. 그리고 이들 농축물에 70% 에탄올을 가하여 50%(w/w) 농도의 추출액을 얻었다.To 50 g of the dried herbal medicine (green tea) was added 500 ml of 70% ethanol, which was immersed at room temperature for 10 days, and filtered. The filtrate was concentrated under reduced pressure to give 20.02 g of a concentrate. Other dry herbal medicines (myrrh, zinnia, horseback) were extracted according to the method described above to give a concentrate of 6.1 g, 5.2 g and 4.8 g, respectively. Then, 70% ethanol was added to these concentrates to obtain an extract having a concentration of 50% (w / w).
[실시예 1.]Example 1.
[치약베이스에서의 항균력 측정][Antibacterial Activity Measurement in Toothpaste Base]
1) 조성물의 제조1) Preparation of the Composition
추출물 제조 실시예의 방법에 따라 제조한 생약추출물을 배합한 아래 처방의 치약을 통상의 제조방법에 따라 제조하였다.Toothpaste of the following formulation was prepared according to the conventional method of formulating the herbal extract prepared according to the method of extract preparation example.
2) 실험방법2) Experiment Method
상기 처방에 따라 제조된 치약 각각 10g을 2% 설탕을 함유한 브레인 허트 인퓨전 브로스(BHI) 10ml에 첨가하여 완전히 분산시킨 후, 이를 치약 농도 0.06-0.18%까지 BHI 브로스로 희석시킨 다음, 충전원인균(S. mutans ; ATCC 25175)과 치주병 원인균(Actinomyces vicosus) ; ATCC 15987)을 접종하고 37℃ 인큐베이터에서 24시간 배양하였다. 배양후, 치약 농도와 생약추출물 농도에 따른 두가지 종류의 균에 대한 항균력 실험을 하여 표 1, 2와 같은 결과를 얻었다.10 g of each toothpaste prepared according to the prescription was added to 10 ml of Brain Hert Infusion Broth (BHI) containing 2% sugar, completely dispersed, diluted with BHI broth to 0.06-0.18% of toothpaste concentration, S. mutans (ATCC 25175) and periodontal disease-causing bacteria (Actinomyces vicosus); ATCC 15987) was inoculated and incubated for 24 hours in a 37 ° C. incubator. After incubation, the antimicrobial activity of the two types of bacteria according to the toothpaste concentration and the herbal extract concentration was obtained as shown in Table 1, 2.
[표 1]TABLE 1
치약베이스에서의 식물추출물에 의한 충치원인균(S. mutans ; ATCC 25175)에 대한 향균력 효과Antimicrobial Effects of S. mutans (ATCC 25175) by Plant Extracts in Toothpaste Base
(+ : 균의 증식, - : 균의 비증식)(+: Growth of bacteria,-: non-growth of bacteria)
[표 2]TABLE 2
치약베이스에서의 식물추출물에 의한 치주병 원인균(Actinomyces viscosus ; ATCC 1578)에 대한 항균력효과Antimicrobial Effect of Periodontal Disease-causing Bacteria (Actinomyces viscosus; ATCC 1578) by Plant Extracts in Toothpaste Base
(+ : 균의 증식, - : 균의 비증식)(+: Growth of bacteria,-: non-growth of bacteria)
라우릴황산나트륨은 치약에서 발포제로서 전체 함량중 1-2%를 치약에 배합하는데 그 자체도 어느 정도의 항균력이 있는 것으로 알려져 있다. 표 1, 2에서 보는 바와 같이 몰약, 상백피, 승마, 녹차의 혼합추출물을 치약 조성물중에 배합한 경우 라우릴황산나트륨만을 배합한 경우에 비해 훨씬 좋은 항균력을 나타내었다.Sodium lauryl sulfate is a foaming agent in toothpaste, 1-2% of the total content in the toothpaste, which itself is known to have some antimicrobial activity. As shown in Tables 1 and 2, when the mixed extract of myrrh, baekryepi, horse riding, and green tea was blended in the toothpaste composition, the antimicrobial activity was much higher than that of sodium lauryl sulfate alone.
[실시예 2.]Example 2.
[치약베이스에서의 GTase 저해효과 측정][Measurement of GTase Inhibitory Effect in Toothpaste Base]
1) 조성물의 제조1) Preparation of the Composition
실험예 1에서와 동일한 방법으로 조성물을 제조하여 실험에 사용한다.The composition was prepared in the same manner as in Experimental Example 1, and used in the experiment.
2) 실험방법2) Experiment Method
① GTase 분리 및 정제① GTase Separation and Purification
스트렙토코커스 뮤탄스 ATCC 25175를 3리터의 BHI 브로스에 접종하여 37℃ 인큐베이터에서 18시간 배양한 후, 원심분리(3000rpm 20분)하여 균체를 제거하고, 그 상층액을 황산암모늄으로 60-70% 포화시킨 후, 4℃에서 18시간 방치하였다. 이렇게 하여 생성된 침전물을 원심분리(3000rpm, 20분)하여 인산칼륨 완충용액(0.05M, pH 6.5) 200ml에 용해한 후 동일 완충용액으로 24시간 투석시켰다. 투석이 완료된 액을 다시 원심분리하여 불용물을 제거하고, 얻은 조효소 용액을 하이드록시아파타이트(Hydroxyapatite)로 충진된 컬럼에 주입시킨후, 이온강도가 다른 동일 완충용액을 단계적으로 용출시켜 정제된 Gtase를 얻었다.Streptococcus mutans ATCC 25175 was inoculated in 3 liters of BHI broth and incubated for 18 hours in a 37 ° C incubator, followed by centrifugation (3000 rpm for 20 minutes) to remove the cells, and the supernatant was saturated with ammonium sulfate 60-70%. After making it stand, it was left to stand at 4 degreeC for 18 hours. The precipitate thus produced was centrifuged (3000 rpm, 20 minutes), dissolved in 200 ml of potassium phosphate buffer (0.05 M, pH 6.5), and dialyzed with the same buffer for 24 hours. The dialysis solution was centrifuged again to remove insoluble matters, and the obtained coenzyme solution was injected into a column filled with hydroxyapatite, and the same buffer solution having different ionic strengths was eluted step by step to purify purified Gtase. Got it.
② GTase 저해 활성 측정② Measurement of GTase Inhibition Activity
상기 방법에 의해 제조된 GTF 50-100㎍, 설탕 70㎍ 및 0.02% NaN3를 함유하는 0.05M 인산칼륨 완충용액(pH 6.5) 4ml에 상기 처방에 따라 제조된 치약 각각 10g을 증류수로 치약 농도 20%까지 희석한 다음, 원심분리(3000rpm, 20분)를 하여 상등액을 얻었다. 이 액을 치약 농도 0.67, 1.5%까지 재희석한 후, 완충용액에 가하고 37℃에서 18시간 동안 항온기를 반응시킨 후, 생성된 글루칸의 양을 스펙트로포토메터에서의 흡광도(660nm)로서 측정하였다. 이 파장에서 흡광도의 감소는 글루칸의 생성억제, 즉 GTase 저해도에 비례한다. GTase 저해 활성도는 다음식에 의해 구하였으며 대조용액의 흡광도는 식물추출액을 제외한 반응액의 흡광도이다.4 g of 0.05 M potassium phosphate buffer solution (pH 6.5) containing 50 to 100 μg of GTF prepared by the above method, 70 μg of sugar and 0.02% NaN 3 , each of 10 g of the toothpaste prepared according to the above formulation was used as distilled water. After diluting to%, centrifugation (3000 rpm, 20 minutes) was carried out to obtain a supernatant. The solution was rediluted to a toothpaste concentration of 0.67 and 1.5%, then added to a buffer solution and allowed to react with an incubator at 37 ° C. for 18 hours. The amount of glucan produced was measured as absorbance (660 nm) in a spectrophotometer. The decrease in absorbance at this wavelength is proportional to the inhibition of glucan production, ie GTase inhibition. The GTase inhibitory activity was determined by the following equation. The absorbance of the control solution was that of the reaction solution except the plant extract.
상기 방법에 의해 표 3과 같은 결과를 얻었다.The result shown in Table 3 was obtained by the said method.
[표 3]TABLE 3
치약베이스에서 식물추출물에 의한 GTase 저해효과GTase Inhibitory Effect of Plant Extracts on Toothpaste Base
치약에 배합되는 라우릴황산나트륨은 약간의 GTase 저해효과가 있지만 충치예방을 위해서 만족할 만한 것이 못되므로 다른 GTase 저해 물질을 첨가할 필요가 있다. 표 3에서와 같이 치약이 처방상에 몰약, 상백피, 승마, 녹차와 같은 식물추출물들을 배합한 경우 라우릴황산나트륨을 함유한 경우와 비하여 훨씬 좋은 효과를 나타내었으므로 실제 치약에 상기 추출물들을 첨가하면 GTase 저해효과에 의해 충치예방 효과를 나타낼 것으로 기대된다.Sodium lauryl sulfate in toothpaste has a slight GTase inhibitory effect, but it is not satisfactory to prevent tooth decay, so it is necessary to add another GTase inhibitor. As shown in Table 3, when toothpaste was formulated with plant extracts such as myrrh, baekryepi, horse riding, and green tea on the prescription, it showed a much better effect than when sodium lauryl sulfate was contained. The inhibitory effect is expected to have caries prevention effect.
표 1-3의 결과에서 보는 바와 같이 치약 처방상에 몰약, 상백피, 승마, 녹차의 혼합식물추출물들을 배합한 경우, 혼합식물추출물들을 배합하지 않는 치약의 경우에 비해 훨씬 좋은 충치원인균 및 치주질환원인균에 대한 항균효과 및 GTase 저해효과를 나타내었다. 따라서 본 발명에 의한 혼합식물추출물들은 우수한 충치 및 치주질환예방 효과를 기대할 수 있다.As shown in the results of Table 1-3, when the mixed tooth extracts of myrrh, lettuce, horseback riding and green tea were mixed in the toothpaste prescription, they were much better than the toothpaste and periodontal pathogens compared to the toothpaste without the mixed plant extracts. It showed antimicrobial and GTase inhibitory effects. Therefore, the mixed plant extracts according to the present invention can expect excellent caries and periodontal disease prevention effect.
본 발명의 구체적인 실시예를 나타내면 아래와 같다.Specific embodiments of the present invention are as follows.
[실시예 1]Example 1
[실시예 2]Example 2
[실시예 3]Example 3
[실시예 4]Example 4
[실시예 5]Example 5
[실시예 6]Example 6
[실시예 7]Example 7
[실시예 8]Example 8
[실시예 9]Example 9
Claims (1)
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
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KR1019910010742A KR940006065B1 (en) | 1991-06-27 | 1991-06-27 | Dentifrice compositions for using carious tooth tooth root disease |
DE4221103A DE4221103A1 (en) | 1991-06-27 | 1992-06-26 | Compsns. contg. herbal extracts - of myrrh, mulberry bark, cimicifuga and/or green tea, esp. for oral hygiene |
FR9207904A FR2678170B1 (en) | 1991-06-27 | 1992-06-26 | ORAL COMPOSITIONS FOR THE PREVENTION OF ODONTONECROSE AND PARADENTARY DISEASE. |
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KR1019910010742A KR940006065B1 (en) | 1991-06-27 | 1991-06-27 | Dentifrice compositions for using carious tooth tooth root disease |
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KR930000105A KR930000105A (en) | 1993-01-15 |
KR940006065B1 true KR940006065B1 (en) | 1994-07-06 |
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KR1019910010742A KR940006065B1 (en) | 1991-06-27 | 1991-06-27 | Dentifrice compositions for using carious tooth tooth root disease |
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KR (1) | KR940006065B1 (en) |
DE (1) | DE4221103A1 (en) |
FR (1) | FR2678170B1 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20000030529A (en) * | 2000-03-06 | 2000-06-05 | 김지홍 | tooth brush pubic hairs production process |
KR101350397B1 (en) * | 2012-05-18 | 2014-01-17 | 주식회사 명성생명공학 | Toothpaste Compositions For Treatment Of Gums Disorder |
CN104095929A (en) * | 2014-07-29 | 2014-10-15 | 桂林实力科技有限公司 | Decayed-tooth-resistant chewing gum |
Families Citing this family (10)
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ITSA990018A1 (en) * | 1999-10-25 | 2001-04-25 | Univ Degli Studi Salerno | NATURAL RESIN SOLUTION FOR THE EXTENSION OF THE SHELF-LIFE CUT DIFIORI. |
AU2002308717A1 (en) | 2001-05-15 | 2002-11-25 | The Procter And Gamble Company | Confectionery compositions |
WO2002092028A2 (en) | 2001-05-15 | 2002-11-21 | The Procter & Gamble Company | Oral care compositions |
WO2002091848A1 (en) | 2001-05-15 | 2002-11-21 | The Procter & Gamble Company | Confectionery compositions |
CA2451833C (en) | 2001-05-15 | 2009-08-18 | The Procter & Gamble Company | Confectionery compositions comprising two metal cations |
MXPA03010455A (en) | 2001-05-15 | 2004-03-09 | Procter & Gamble | Oral care compositions. |
US6767560B2 (en) | 2002-01-22 | 2004-07-27 | Paul H Paek | Fabrication method of oral care composition |
BRPI0413535A (en) * | 2003-09-09 | 2006-10-10 | Dsm Ip Assets Bv | essentially anhydrous topical agent with oral activity comprising one or more oxidation sensitive substances |
US20060140881A1 (en) * | 2004-12-22 | 2006-06-29 | Guofeng Xu | Oral care compositions containing flavonoids and flavans |
US20060141072A1 (en) * | 2004-12-29 | 2006-06-29 | Arvanitidou Evangelia S | Oxidation resistant dentifrice compositions |
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DE3642426C1 (en) * | 1986-12-11 | 1988-02-11 | Wolfgang Schuster | Liquid impregnating composition for dental prostheses and parts thereof |
JPH0253717A (en) * | 1988-08-18 | 1990-02-22 | Momotani Jiyuntenkan:Kk | Dentifrice or mouth wash |
-
1991
- 1991-06-27 KR KR1019910010742A patent/KR940006065B1/en not_active IP Right Cessation
-
1992
- 1992-06-26 DE DE4221103A patent/DE4221103A1/en not_active Ceased
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR20000030529A (en) * | 2000-03-06 | 2000-06-05 | 김지홍 | tooth brush pubic hairs production process |
KR101350397B1 (en) * | 2012-05-18 | 2014-01-17 | 주식회사 명성생명공학 | Toothpaste Compositions For Treatment Of Gums Disorder |
CN104095929A (en) * | 2014-07-29 | 2014-10-15 | 桂林实力科技有限公司 | Decayed-tooth-resistant chewing gum |
Also Published As
Publication number | Publication date |
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DE4221103A1 (en) | 1993-01-07 |
FR2678170B1 (en) | 1994-12-23 |
KR930000105A (en) | 1993-01-15 |
FR2678170A1 (en) | 1992-12-31 |
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