CN1069189C - 口腔用组合物 - Google Patents
口腔用组合物 Download PDFInfo
- Publication number
- CN1069189C CN1069189C CN91104855A CN91104855A CN1069189C CN 1069189 C CN1069189 C CN 1069189C CN 91104855 A CN91104855 A CN 91104855A CN 91104855 A CN91104855 A CN 91104855A CN 1069189 C CN1069189 C CN 1069189C
- Authority
- CN
- China
- Prior art keywords
- cetylpyridinium chloride
- lower alkyl
- composition
- amino acid
- basic amino
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Fee Related
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
-
- 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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
-
- 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4926—Cosmetics 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cosmetics (AREA)
Abstract
口腔用组合物,其特征是由氯化十六烷基吡啶和Nα-长链酰基碱性氨基酸低级烷基酯或它的盐配合而成。
本发明的口腔用组合物能促进氯化十六烷基吡啶吸附到牙齿表面上、防止形成牙垢,对于预防龋齿具有良好效果。
Description
本发明涉及口腔用组合物,更具体地说,涉及一种能促进氯化十六烷基吡啶鎓(杀菌剂)吸附到牙齿表面上的口腔用组合物。
牙垢(plague)是由于突变种链球菌等口腔内的细菌吸附在牙齿表面上繁殖而形成的物质,众所周知,这种物质是造成龋齿的原因,此外人们还知道,它也是牙龈炎和齿槽脓漏的致病原因。因此,对于口腔卫生来说,除去牙垢及防止其附着(plaguecontrol)是十分重要的。
最常用的除牙垢方法是刷牙,也就是利用牙刷以机械方式除去牙垢。但是,要想通过刷牙彻底地除去牙垢,必须具有高超的刷牙技术,然而一般的人刷牙不十分仔细,因此牙垢的去除不彻底,尽管也经常刷牙,但龋齿、牙龈炎、齿槽脓漏等牙病的患病率却不见减少,这就是目前的现状。
因此,为了弥补刷牙的不足,或者作为替代刷牙的方法,人们一直在研究用化学方法去除或预防牙垢,比较有名的是具有C8-C18的直链或支链烷基的吡啶鎓翁化合物,其中,公认在临床应用上有效并且安全的化合物是氯化十六烷基呲啶鎓。
氧化十六烷基吡啶鎓是由下面的化学式表示的化合物已知这种化合物具有杀菌作用并且比较容易吸附在口腔粘膜和牙齿表面上,因此使用它来防止口腔内的细菌吸附到牙齿表面上,进而防止形成牙垢。但是,目前,关于促进这种氯化十六烷基吡啶鎓吸附到牙齿表面上、进一步提高其作用效果的研究工作还没有头绪。
本发明人为了促进氯化十六烷基吡啶鎓在口腔内的存留、尤其是使它吸附到牙齿表面上、以进一步提高其防止牙垢形成的效果这一目的,进行了精心的研究,结果发现,将氯化十六烷基吡啶鎓与Nα-长链酰基碱性氨基酸的低级烷基酯或它的盐组合起来,可以显著地促进氯化十六烷基吡啶鎓吸附到牙齿上,从而完成了本发明。
本发明提供了一种口腔用组合物,其特征在于,该组合物是将氯化十六烷基吡啶鎓与Nα-长链酰基碱性氨基酸低级烷基酯或它的盐配合在一起而构成的。本发明的口腔用组合物能促进氧化十六烷基吡啶鎓吸附到牙齿表面上,防止牙垢形成,因此对于预防龋齿有良好的效果。
在这一组合物中,氯化十六烷基吡啶鎓的配入量在0.0002%(重量)以上,最理想的配入量是在0.01%(重量)以上。就杀菌效果而言,对氯化十六烷基吡啶鎓的配入量的上限没有特别的限制,但由于氯化十六烷基吡啶鎓带有苦味,并且,如果用量过多有可能引起牙齿染色,此外,还由于考虑到对口腔粘膜的影响等,因此它的用量通常最好是在1%(重量)以下。
所使用的Nα-长链酰基碱性氨基酸低级烷基酯中的碱性氨基酸部分,最好是鸟氨酸、赖氨酸、精氨酸,它们可以是旋光体也可以是外消旋变体。其中的酰基是碳原子数为8-22的饱和的或不饱和的、天然的或合成的脂肪酸残基,例如月桂酰基、肉豆寇基、棕榈酰基、硬脂酰基等单一脂肪酸残基,此外,也可以是椰子油脂肪酸残基、牛油脂肪酸残基等天然的混合脂肪酸残基。低级烷基酯也是可以的,其中以甲酯、乙酯、丙酯较为适宜。
作为这些Nα-长链酰基碱性氨基酸低级烷基酯的盐,可以列举出:无机酸盐,例如盐酸盐、硫酸盐;或有机酸盐,例如醋酸盐、酒石酸盐、柠檬酸盐、对甲基苯磺酸盐、脂肪酸盐、酸性氨基酸盐等,尤其是以谷氨酸盐、焦谷氨酸盐、醋酸盐、柠檬酸盐最为适用。
在本发明中,Nα-长链酰基碱性氨基酸低级烷基酯及其盐是促进氯化十六烷基吡啶鎓吸附到牙齿表面上的成分,其配入量应至少相当于氯化十六烷基吡啶鎓重量的1/5,通常希望在1/5-10倍之间。若其含量过低,促进氯化十六烷基吡啶鎓吸附到牙齿上的效果就不够理想。
本发明的口腔用组合物,可按常规方法将所需成分混合,制成牙粉、牙膏、含漱剂、片剂等,也可以制成气溶胶喷入口腔内。此外,还可以制成牙齿涂敷剂,将其浸透用于清洁牙缝的扁平蜡渍线或牙签,然后再使用。
其它的配入成分,只要不妨碍氯化十六烷基吡啶鎓吸附到牙齿表面上及其杀菌作用,在此情况下,通常任何成分都可用于这种组合物中,不过,在使用发泡剂或增溶剂的情况下,阴离子型的发泡剂或增溶剂不甚理想,若使用非离子或阳离子型的发泡剂或增溶剂,特别是聚氧乙烯聚氧化丙二醇、亚乙基二胺四聚氧乙烯聚氧化丙二醇等,将能进一步提高氯化十六烷基吡啶鎓的效果。
下面通过实验及实施例进一步详细说明本发明,但本发明不受这些实施例的限制。实施例中的(%)都是指重量%。
实验1 氯化十六烷基吡啶鎓吸附到牙齿表面上的实验
牙齿表面珐琅质的成分是:97%无机物、1%有机物、2%水分,无机物的主要成分是被称为羟基磷灰石(Ca10(PO4)6(OH)2)的磷酸钙。
将羟基磷灰石盘状物(BiO-Gel HTP,美国Bio.Lad.Labora-tory,φ13mm、250mg、以150kg/cm2压制成片,在600下烧结6小时)在人的唾液中于37℃下浸渍18小时,然后用其作为牙齿珐琅质的模型。通过在唾液中浸渍,使羟基磷灰石表面上吸附了唾液粘蛋白,从而接近于被唾液浸湿的真实的牙齿珐琅质的状态。取上述用唾液处理过的羟基磷灰石放入试管中,加入1nl0.05%氯化十六烷基呲啶(Malk公司)水溶液,在37℃下浸荡30分钟,然后用6ml水洗涤,用萃取溶剂(50mM月桂基硫酸钠、40mM柠檬酸缓冲pH3.0/乙腈=30/70)萃取,将此提取液作为高速液相色谱法用的样品。高速液相色谱法采用在40℃保温的Lichrosorb R P select B、φ4.0mm×250mm作为分离柱、使用萃取溶剂作为洗脱液。洗脱液流速定为1ml/分钟,氯化十六烷基吡啶鎓的检测操作是利用在258nm处的吸光度来测定、再用由氯化十六烷基吡啶鎓作成的标准曲线进行定量。
同样地,将表1中所示的各种添加剂每种按0.1%添加到0.05%的氧化十六烷基吡啶鎓中,在所得混合溶液中浸渍经过唾液处理的磷灰石圆盘,然后对氯化十六烷基吡啶鎓进行定量。另外,在显示出提高氯化十六烷基吡啶鎓在磷灰石圆盘上吸附量的效果的添加剂中,对于N-可可酰基-L-精氨酸乙酯吡咯烷酮羧酸盐,改变其添加量使之分别为0.005%、0.01%、0.05%,研究其浓度对氯化十六烷基吡啶鎓吸附量的影响,所获结果示于表1中。
表1
| 化合物名称 | 氯化十六烷基吡啶含量(μg/圆盘) | |
| 最初 | 3小时后 | |
| 0.05%氯化十六烷基吡啶鎓 | 170 | 63 |
| ,,+0.1%N-可可酰基-L-精氨酸甲酯盐酸盐 | 411 | 321 |
| ,,+0.1% N-月桂酰基-L-精氨酸甲酯吡烷酮羧酸盐 | 436 | 336 |
| ,,+0.1% N-可可酰基-L-精氨酸乙酯吡烷酮羧酸盐 | 438 | 346 |
| ,,+0.1% N-棕榈酰基-L-赖氨酸甲酯醋酸盐 | 424 | 330 |
| ,,+0.1% N-月桂酰基甲胺基乙磺酸钠 | 59 | 18 |
| ,,+0.1% N-月桂酰基-甲基-β-丙氨酸钠 | 173 | 60 |
| ,,+0.005% N-可可酰基-精氨酸乙酯吡咯烷酮羧酸盐 | 175 | 119 |
| ,,+0.01%N-可可酰基-L-精氨酸乙酯吡咯烷酮羧酸盐 | 331 | 242 |
| ,,+0.05%N-可可酰基-L-精氨酸乙酯吡咯烷酮羧酸盐 | 392 | 294 |
如表1中所示,如果配入Nα-长链酰基碱性氨基酸低级烷基酯,就可使得氯化十六烷基吡啶鎓特别牢固地吸附到羧基磷灰石圆盘上,其浓度应至少相当于氯化十六烷基吡啶鎓重量的1/5。
实验2
氯化十六烷基吡啶鎓如果与酸性物质形成盐,就有可能失去活性,为此,对于杀菌活性的保持进行了如下实验。
对于利用添加Nα-长链酰基碱性氨基酸低级烷基酯来增加氯化十六烷基吡啶鎓向羧基磷灰石圆盘上吸附的试验样品,在试验时,将圆盘悬置于5%蔗糖BHI培养基中,放入一白金耳突变种链球菌,在37℃下培养18小时。实验结果,在羧基磷灰石上未发现噬菌区,这证实了吸附在羧基磷灰石圆盘上的氯化十六烷基吡啶鎓保持了抗菌活性。
实施例1
将下列各成分按常规方法脱气、拌合、搅拌、制成牙膏。
成分 量
聚氧化亚甲基磷酸氢钙 20.0%
聚氧化丙二醇 30.0%
丙三醇 10.0%
氯化十六烷基吡啶鎓 0.1%
N-月桂酰基-L-精氨酸
甲酯吡咯烷酮羧酸盐 0.05%
糖精钠 0.2%
香料 1.0%
净化水 余量
实施例2
将下列各成分按常规方法脱气、搅和、搅拌、制成牙膏。
成分 量
碳酸钙 35.0%
羟乙基纤维素 1.5%
亚乙基二胺四聚氧乙烯聚氧
化丙二醇 5.0%
山梨糖醇 30.0%
氯化十六烷基吡啶 0.01%
N-可可酰基-L-精氨酸
甲酯盐酸盐 0.01%
糖精钠 0.1%
香料 1.0%
净化水 余量
实施例3
将下列成分按常规方法混合搅拌、制成漱口液。
成分 量
乙醇 10.0%
丙三醇 10.0%
聚氧乙烯聚氧化丙二醇 1.5%
糖精钠 0.02%
氯化十六烷基吡啶鎓 0.05%
N-可可酰基-L-精氨酸乙酯
吡咯烷酮羧酸盐 0.1%
香料 0.3%
净化水 余量
实施例4
将若干根由尼龙-66制成的细纤度纤维搓成630旦尼尔的丝线,将其在下述混合液中浸渍,使之通过50℃的干燥管、蒸发掉乙醇,与此同时卷取到线轴上,制成清洁牙缝用的扁平的蜡渍线。
成分 量
氯化十六烷基吡啶鎓 5.0%
N-可可酰基-L-精氨酸乙酯
吡咯烷酮羧酸盐 10.0%
乙醇 85.0%
Claims (2)
1.一种口腔用组合物,其特征在于,该组合物含有十六烷基吡啶嗡氯化物和Nα-长链酰基碱性氨基酸低级烷基酯或其盐,其中,所述的长链酰基是C8-C22的饱和或不饱和的脂肪酸残基,所述的低级烷基酯是甲基酯、乙基酯或丙基酯,以及Nα-长链酰基碱性氨基酸低级烷基酯或其盐的配入量至少相当于氯化十六烷基吡啶鎓重量的1/5。。
2.根据权利要求1所述的口腔用组合物,其中,所述的十六烷基吡啶嗡氯化物的配合量为0.0002-1重量%,Nα-长链酰基碱性氨基酸低级烷基酯或其盐与十六烷基吡啶嗡氯化物的重量比为0.2~10倍。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP139125/1990 | 1990-05-29 | ||
| JP2139125A JPH0684294B2 (ja) | 1990-05-29 | 1990-05-29 | 口腔用組成物 |
| JP139125/90 | 1990-05-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1057582A CN1057582A (zh) | 1992-01-08 |
| CN1069189C true CN1069189C (zh) | 2001-08-08 |
Family
ID=15238097
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN91104855A Expired - Fee Related CN1069189C (zh) | 1990-05-29 | 1991-05-29 | 口腔用组合物 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US5266306A (zh) |
| EP (1) | EP0485616B1 (zh) |
| JP (1) | JPH0684294B2 (zh) |
| KR (1) | KR0167019B1 (zh) |
| CN (1) | CN1069189C (zh) |
| AT (1) | ATE126051T1 (zh) |
| AU (1) | AU633217B2 (zh) |
| CA (1) | CA2060895C (zh) |
| DE (1) | DE69111985T2 (zh) |
| DK (1) | DK0485616T3 (zh) |
| ES (1) | ES2078523T3 (zh) |
| GR (1) | GR3017090T3 (zh) |
| HK (1) | HK1001670A1 (zh) |
| MY (1) | MY106151A (zh) |
| WO (1) | WO1991018585A1 (zh) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2125483A1 (en) * | 1991-12-11 | 1993-06-24 | Mary Ann Hunter | Cetylpyridinium chloride and domiphen bromide in organic solvent |
| CN1034417C (zh) * | 1992-12-04 | 1997-04-02 | 福州人造板厂 | 中密度纤维板用脲醛树脂的制备方法 |
| CA2196525C (en) * | 1994-08-05 | 2004-05-11 | Jean-Paul Gerome | Tactile-acoustic information detecting and measuring apparatus and method |
| GB9611364D0 (en) * | 1996-05-31 | 1996-08-07 | Smithkline Beecham Plc | Composition |
| US5948390A (en) * | 1997-08-25 | 1999-09-07 | Pfizer Inc. | Stable zinc/citrate/CPC oral rinse formulations |
| US5874068A (en) * | 1997-12-08 | 1999-02-23 | Warner-Lambert Company | Stabilized antiplaque and antigingivitis oral compositions containing N.sup.α -alkyl-L-arginine alkyl ester salts |
| KR100308247B1 (ko) * | 1999-03-12 | 2001-09-26 | 신창국 | 구강 청정용 조성물 |
| KR100630512B1 (ko) * | 2000-06-13 | 2006-09-29 | 주식회사 엘지생활건강 | 감기와 인후두염의 예방 및 치료를 위한 구강청정제 조성물 |
| WO2002031105A1 (fr) * | 2000-10-12 | 2002-04-18 | Sapporo Immuno Diagnostic Laboratory | Procede et instrument de collecte de liquide dans la cavite orale |
| EP1380829A4 (en) | 2001-04-20 | 2009-12-30 | Sapporo Immuno Diagnostic Lab | APPARATUS FOR USE IN COLLECTING AND WINNING LIQUID SECRET IN MOUTHROOM |
| MXPA04001169A (es) | 2001-08-09 | 2005-02-17 | Miret Lab | Nuevos sistemas de conservacion y su uso en preparaciones cosmeticas. |
| BRPI0114147B1 (pt) | 2001-08-09 | 2017-06-27 | Laboratorios Miret, S.A. | Cosmetic or dermatological composition in the form of an emulsion understanding cationic surfaces |
| WO2003034842A1 (en) | 2001-10-25 | 2003-05-01 | Laboratorios Miret, S.A. | Use of cationic preservative in food products |
| AU2002218301A1 (en) * | 2001-11-15 | 2003-06-10 | Laboratorios Miret S.A. | Use of cationic surfactant as antimicrobial activity enhancer in deodorants and oral care |
| US6579513B1 (en) | 2002-01-03 | 2003-06-17 | Playtex Products, Inc. | Hygiene mouthspray composition |
| DE60229000D1 (de) | 2002-02-01 | 2008-10-30 | Miret Lab | Enzymatische synthese von n(alpha)-acyl-l-argininestern |
| WO2003094638A1 (en) | 2002-05-08 | 2003-11-20 | Laboratorios Miret, S.A. | New preservatives and protective systems |
| US6669929B1 (en) | 2002-12-30 | 2003-12-30 | Colgate Palmolive Company | Dentifrice containing functional film flakes |
| US6946119B2 (en) * | 2003-02-14 | 2005-09-20 | J.M. Huber Corporation | Precipitated silica product with low surface area, dentifrices containing same, and processes |
| US20040258632A1 (en) * | 2003-06-23 | 2004-12-23 | Boyd Thomas J. | Stable aqueous antiplaque oral compositions |
| WO2005000261A1 (en) * | 2003-06-23 | 2005-01-06 | Colgate-Palmolive Company | Mouth rinse compositions containing n-acyl-arginine alkyl ester salts |
| US20040258629A1 (en) * | 2003-06-23 | 2004-12-23 | Boyd Thomas J. | Antiplaque confectionery dental composition |
| EP1635774B2 (en) * | 2003-06-23 | 2011-01-26 | Colgate-Palmolive Company | Stable dentifrice compositions |
| US8287843B2 (en) | 2003-06-23 | 2012-10-16 | Colgate-Palmolive Company | Antiplaque oral care compositions |
| US9241885B2 (en) * | 2004-01-29 | 2016-01-26 | The Procter & Gamble Company | Oral care compositions comprising increased bioavailable levels of quaternary ammonium antimicrobials |
| US20070014740A1 (en) * | 2005-07-15 | 2007-01-18 | Colgate-Palmolive Company | Oral compositions having cationic active ingredients |
| US20080260836A1 (en) * | 2007-04-18 | 2008-10-23 | Thomas James Boyd | Films Comprising a Plurality of Polymers |
| SG191691A1 (en) * | 2008-02-08 | 2013-07-31 | Colgate Palmolive Co | Dental floss |
| CN102970969B (zh) | 2010-07-12 | 2015-03-11 | 花王株式会社 | 洁牙组合物 |
| CN102416011A (zh) * | 2011-10-10 | 2012-04-18 | 艾硕特生物科技(昆明)有限公司 | 一种广谱、高效的抗菌洗液 |
| EP4106716B1 (en) | 2020-02-18 | 2026-01-28 | Sunstar Americas, Inc. | Oral care composition |
| JP2023177682A (ja) * | 2022-06-02 | 2023-12-14 | サンスター株式会社 | プラーク形成抑制用組成物 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5386047A (en) * | 1976-12-27 | 1978-07-29 | Colgate Palmolive Co | Oral antiibacterial composition |
| EP0422803A2 (en) * | 1989-10-11 | 1991-04-17 | Beecham Group p.l.c. | Dentifrice comprising cationic antibacterial agent |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL104948C (zh) * | 1952-02-15 | |||
| US2772203A (en) * | 1952-04-03 | 1956-11-27 | Colgate Palmolive Co | Stable dental creams containing higher aliphatic acyl amide of aminocarboxxylic acid compound |
| US2757125A (en) * | 1952-05-16 | 1956-07-31 | Colgate Palmolive Co | N-higher alkyl-4-carboxy-2-pyrrolidones and compositions therewith |
| US2772204A (en) * | 1954-09-13 | 1956-11-27 | Colgate Palmolive Co | Dental preparations containing higher aliphatic acyl sarcoside compounds |
| US2909535A (en) * | 1955-03-15 | 1959-10-20 | Colgate Palmolive Co | Novel higher aliphatic acid derivatives and compositions containing the same |
| US2842479A (en) * | 1955-05-24 | 1958-07-08 | Colgate Palmolive Co | Nu-higher aliphatic acyl alpha-amino aryl acetic acids and compositions therewith |
| GB1352420A (en) * | 1971-06-18 | 1974-05-08 | Ajinomoto Kk | Arginine derivatives their production and their use |
| AU578392B2 (en) * | 1984-07-31 | 1988-10-20 | Lion Corporation | Toothpaste composition containing silica |
| JPS61126010A (ja) * | 1984-11-20 | 1986-06-13 | Lion Corp | 口腔用組成物 |
| JPH0720854B2 (ja) * | 1986-02-20 | 1995-03-08 | ライオン株式会社 | 口腔用組成物 |
| JPH085773B2 (ja) * | 1986-09-02 | 1996-01-24 | ライオン株式会社 | 口腔用組成物 |
| LU86587A1 (fr) * | 1986-09-15 | 1988-04-05 | Oreal | Dentifrice contenant un tensio-actif non ionique poly(hydroxypropylether)et un sel d'un derive specifique d'un produit de degradation des proteines |
| DE68914386T2 (de) * | 1988-10-20 | 1994-11-17 | Ajinomoto Kk | Zahnpastaähnliche Zusammensetzung. |
| JPH0825861B2 (ja) * | 1989-04-24 | 1996-03-13 | サンスター株式会社 | 歯磨組成物 |
| GB9008433D0 (en) * | 1990-04-12 | 1990-06-13 | Beecham Group Plc | Novel compositions |
-
1990
- 1990-05-29 JP JP2139125A patent/JPH0684294B2/ja not_active Expired - Lifetime
-
1991
- 1991-05-23 MY MYPI91000874A patent/MY106151A/en unknown
- 1991-05-23 HK HK98100745A patent/HK1001670A1/zh not_active IP Right Cessation
- 1991-05-23 AT AT91909703T patent/ATE126051T1/de not_active IP Right Cessation
- 1991-05-23 WO PCT/JP1991/000691 patent/WO1991018585A1/ja not_active Ceased
- 1991-05-23 AU AU78938/91A patent/AU633217B2/en not_active Ceased
- 1991-05-23 EP EP91909703A patent/EP0485616B1/en not_active Expired - Lifetime
- 1991-05-23 US US07/828,793 patent/US5266306A/en not_active Expired - Lifetime
- 1991-05-23 DE DE69111985T patent/DE69111985T2/de not_active Expired - Lifetime
- 1991-05-23 ES ES91909703T patent/ES2078523T3/es not_active Expired - Lifetime
- 1991-05-23 CA CA002060895A patent/CA2060895C/en not_active Expired - Lifetime
- 1991-05-23 DK DK91909703.0T patent/DK0485616T3/da active
- 1991-05-23 KR KR1019910701952A patent/KR0167019B1/ko not_active Expired - Fee Related
- 1991-05-29 CN CN91104855A patent/CN1069189C/zh not_active Expired - Fee Related
-
1995
- 1995-08-10 GR GR950401933T patent/GR3017090T3/el unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5386047A (en) * | 1976-12-27 | 1978-07-29 | Colgate Palmolive Co | Oral antiibacterial composition |
| EP0422803A2 (en) * | 1989-10-11 | 1991-04-17 | Beecham Group p.l.c. | Dentifrice comprising cationic antibacterial agent |
Also Published As
| Publication number | Publication date |
|---|---|
| AU7893891A (en) | 1991-12-31 |
| CA2060895A1 (en) | 1991-11-30 |
| CN1057582A (zh) | 1992-01-08 |
| ES2078523T3 (es) | 1995-12-16 |
| KR920702615A (ko) | 1992-10-06 |
| EP0485616A4 (en) | 1992-09-16 |
| JPH0684294B2 (ja) | 1994-10-26 |
| HK1001670A1 (zh) | 1998-07-03 |
| DE69111985T2 (de) | 1996-05-02 |
| KR0167019B1 (ko) | 1999-01-15 |
| JPH0436231A (ja) | 1992-02-06 |
| DK0485616T3 (da) | 1995-09-18 |
| ATE126051T1 (de) | 1995-08-15 |
| US5266306A (en) | 1993-11-30 |
| EP0485616B1 (en) | 1995-08-09 |
| AU633217B2 (en) | 1993-01-21 |
| MY106151A (en) | 1995-03-31 |
| EP0485616A1 (en) | 1992-05-20 |
| GR3017090T3 (en) | 1995-11-30 |
| WO1991018585A1 (fr) | 1991-12-12 |
| CA2060895C (en) | 2001-08-21 |
| DE69111985D1 (de) | 1995-09-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1069189C (zh) | 口腔用组合物 | |
| HK1001670B (zh) | 口腔结构 | |
| US4224307A (en) | Mouthwash and methods | |
| CN1169516C (zh) | 口腔清洁剂组成物及牙膏、牙粉组成物 | |
| EP0008295A1 (en) | Compositions and methods for inhibiting plaque formation | |
| US5032388A (en) | Method of preventing tartar formation | |
| US4477429A (en) | Oral compositions comprising N.sup.α -alkyl derivatives of arginine | |
| JP2005008579A (ja) | 口腔細菌の共凝集抑制剤 | |
| Van der Weijden et al. | The effectiveness of an electronic toothbrush in the removal of established plaque and treatment of gingivitis | |
| JP4452601B2 (ja) | 液体口腔用組成物 | |
| JP6077336B2 (ja) | 殺菌洗浄用組成物 | |
| JPH0684293B2 (ja) | 口腔用組成物 | |
| CN114948765B (zh) | 一种漱口水及其制备方法 | |
| JPS61200905A (ja) | 口腔用組成物 | |
| JP7391612B2 (ja) | 口腔用組成物 | |
| CN104188816A (zh) | 一种漱口水及其制备方法 | |
| DE3016359A1 (de) | Zahn- bzw. mundwasserloesung zur bildung von schutzfilem und hierfuer geeignetes verfahren | |
| KR20110112498A (ko) | 삼씨 기름을 함유하는 치약조성물 | |
| CN114681341B (zh) | 稳定的可除渍美白、减轻牙龈炎症的牙膏及其制备方法 | |
| JPH06287126A (ja) | 口腔用組成物 | |
| JPH0627062B2 (ja) | 口腔用組成物 | |
| CN109091434A (zh) | 一种具有防止牙龈出血功能的牙膏 | |
| JP3031785B2 (ja) | 口腔用組成物 | |
| RU2240777C1 (ru) | Композиция зубной пасты | |
| SU1342502A1 (ru) | Зубна паста |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C15 | Extension of patent right duration from 15 to 20 years for appl. with date before 31.12.1992 and still valid on 11.12.2001 (patent law change 1993) | ||
| OR01 | Other related matters | ||
| C19 | Lapse of patent right due to non-payment of the annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |