CN1047304C - 补充矿质的牙齿保养制剂 - Google Patents
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Abstract
一种牙膏,含有普通成分和含有硅酸和二水合磷酸氢钙组合作为磨光剂。这种牙膏可使牙齿表面得到极好修复。这些效果通过控制的补充矿质,特别在擦痕及牙质孔洞方面得以实现。通过加入镁离子和/或氟磷酸离子这种效果被加强了。
Description
本发明涉及具有牙齿表面修复效果的牙齿保养制剂和一种修复牙齿表面的方法。
牙齿保养制剂首先用于清洁牙齿表面,去除脏物,食物残渣和固着的含菌牙垢,也曾尝试通过特殊的添加剂,如氟化合物或抗菌的物质,对于牙病如龋齿或牙周疾病给予预防。
龋齿的初级阶段呈现牙釉质受损和明晰的牙质细孔洞(Tomes浅坑),这是在产酸细菌影响下经过溶解过程形成的。这种牙质受损使牙颈对温度的敏感度明显增大,而加入脱敏活性物质仅起到减轻疼痛的作用。人们已经试验加入一些降低磷灰石溶解度的附加物去阻止牙齿表面损伤的形成。新近已提出用补充矿质的牙齿保养制剂来减轻现存损伤的建议。Chow和Brown在J.Dent.Res.54(1975)65-70上曾建议使用二水合磷酸氢钙给牙质补充矿质。从US,4,097,588中得知补充矿质的漱口水就含有饱和的二水合磷酸氢钙。
按此方法修复牙齿表面的已知试验,已导致牙齿表面上羟基磷灰石晶体无控生长,对牙齿表面以后的损坏几乎没有抵抗力。因此本发明的目的是研制一种具有可控制的补充矿质作用的牙膏,特别在划痕和牙质孔洞上进行补充矿质,基本上修复平整,使其形成密实平滑的牙面。
我们发现,借助于符合本发明的磨光材料的组合,这一目的在很大程度上实现了。
本发明涉及一种修复牙齿表面的牙膏,它含有磨光料,氟化物,保湿材料,粘合材料和水,其特征在于它含有硅酸和二水合磷酸氢钙作为磨光组分,两者的重量比为10∶1至1∶1。经观察,用这种牙膏有规律的处理牙齿,在广泛平整牙面的同时牙质孔洞被封闭了。
适合作擦拭物的硅酸磨光料,已知的有凝胶硅酸、水凝胶硅酸和沉淀硅酸。凝胶硅酸的产生是通过硅酸钠溶液与强的含水无机酸作用,经过水溶胶,老化成水凝胶,经洗涤干燥而成。保护条件下干燥至水含量为15%-35%(重量),即得已知的所谓水凝胶硅酸,如从US,4,153,680中了解的,干燥水含量低于15%(重量)的硅酸,原疏松结构的水凝胶不可逆地收缩成紧密结构的干凝胶,这种干凝胶硅酸在,例如,US,3,538,230中描述过。
更适宜的硅酸类磨光料组份是沉淀硅酸,这是将稀的碱金属硅酸盐溶液在一定条件下加入强酸得到的,在这种条件下不会发生溶胶和凝胶的聚集。沉淀硅酸的适宜生产方法在,例如,DE-OS2522486和DE-OS3114493中有述。最好的沉淀硅酸是按DE-OS3114493生产的,其BET表面积是15-110m2/g,颗粒尺寸为0.5-20μ,其中80%(重量)以上的颗粒在5μ以下。在甘油/水(1∶1)30%的分散体系中粘度为30-60Pa.S(20℃),沉淀硅酸在牙膏中含量为10-20%(重量),以整个牙膏计。
另外,最适宜的沉淀硅酸显示磨圆的棱角和边,可以买到,商标为Sident 12DS(DEGUSSA)。
为得到足够量的平均粒子尺寸低于5μ的硅酸,更具体地,是含有基本粒子大小在1-3μ的至少3%(重量)(以整个牙膏计)的硅酸,前述沉淀硅酸最好与一种BET表面积为150-250的精细型硅酸一起使用。合适的硅酸类型为,例如,Sipernat 22Ls(DFGUSSA),在牙膏中添加量为1-5%(重量),以整个牙膏计。
本发明的牙膏含有少量的新鲜沉淀硅酸,即在牙膏生产中就地制备的硅酸,经证明它对平滑牙表面特别有利。这是通过生产牙膏时,例如,加入柠檬酸把PH值调为3-5,然后加入少量硅酸钠水溶液将PH值提到7-7.5来实现。按照这种方法就地形成的硅酸颗粒极细,占牙膏重量的0.1%以下。
除硅酸磨光料外,还可少量的用其它已知的磨光料,例如氧化铝,以含有γ-和α-氧化铝成分的略加焙烧的矾土形式使用。这种氧化铝可以买到,商品名为Poliertonerde P10 feinst(Giulini化学公司产)。当然,任何这种附加的磨光料成分与硅酸磨料的重量比应不高于(1-15)∶100。
此外,第二种必备的磨料成分是二水合磷酸氢钙(CaHPO4·2H2O)它在自然界中以透钙磷石贮藏。二水合磷酸氢钙长期作为牙膏中的磨光材料,在市场上可买到1-50μ的适宜颗粒,加入的最佳重量为牙膏的1-5%。
按此发明的牙膏,应尽可能不含有其它形式钙离子的磨光成分,例如白垩成其它磷酸钙盐。
另外观察到镁离子对牙损伤处生长的羟基磷灰石的控制的晶体生长具有有利的影响,促进牙釉质加速固化,这对本发明要解决的课题给出了进一步的贡献。因此本发明还涉及含水溶性镁盐的牙膏,含镁量为0.1-0.5%(重量)。在20℃水中可溶解至少0.5%(重量)的任何盐都是合适的镁盐(按镁计算),如MgSO4,MgCl2和氟基磷酸镁(MgPO3F)。
另外已确定氟磷酸离子对羟基磷灰石的控制的晶体生长也具有有利影响,因此按本发明的这种牙膏最好含有氟基磷酸盐作为氟化物,含量满足0.2-2.0%(重量)(PO3F-)。例如,碱金属盐是适合于此目的。适合的碱金属盐的一个实例是商用的氟基磷酸钠。使用氟基磷酸镁作为氟化物就可获得特别有利的镁离子和氟磷酸离子含量。
保湿剂、粘结剂和水的组合适合于用作本发明牙膏的载体,基于本发明的磨光料的组合,载体可使得从管子、排放容器或软瓶中排放时具有合适的稠度。
作保湿剂的有,例如,甘油、山梨糖醇、木糖醇、丙二醇、聚乙二醇,尤其是那些平均分子量为200-800的。合适的稠度调节剂(或粘结剂)有,例如,天然和/或合成的水溶性聚合物,如藻酸盐,角又菜酸盐,黄蓍胶,淀粉和淀粉醚、纤维素醚类如羧甲基纤维素(钠盐),羟乙基纤维素、甲基羟丙基纤维素、瓜耳树胶、金合欢胶、琼脂、黄原酸酯胶、稻豆粉、果胶、水溶性的羧乙烯基聚合物(如Carbopol型)、聚乙烯醇,聚乙烯吡咯烷酮,聚乙二醇,特别是那些分子量为1500-1000000的。
其它适合作粘度调节剂的有,例如,层状硅酸盐类如蒙脱石粘土、胶状浓缩硅酸类如气凝胶硅酸,焦精硅酸,或是精磨的沉淀硅酸。为了生产含有发明的磨光料组合的牙膏,特别适用的载体含有:
15-25%(重量)甘油
10-20%(重量)山梨糖醇
1-5% (重量)聚乙二醇(分子量400)
1-5% (重量)浓缩硅酸
0.1-1%(重量)黄原酸酯胶
35-45%(重量)水
牙膏的粘度可调低为2000-10000m.Pa.S(25℃),使其成为一种液态牙齿清洁剂,能从软塑料瓶挤到牙刷上,渗入毛刷中,并且不会从牙刷上滴落。为此目的,适合作粘结剂的最佳配比是由0.1-1%(重量)的黄原酸酯胶和0.01-5%(重量)稳定粘度的添加剂组成。这些添加剂有羟丙基取代的水合胶体或聚乙二醇/聚丙二醇的共聚物,其平均分子量从1000到5000。
另一些常见的牙膏添加剂是,例如,表面活性剂以提高净化效果,在刷牙时产生泡沫,稳定载体中的磨光组分的分散,加入量总共可达牙膏组合物的约5%(重量)。适宜的表面活性剂有,例如,在烷基中含有12-18个碳原子的线性烷基硫酸钠。这种物质对牙垢上的细菌代谢也具有酶抑制作用。另一些适宜的表面活性剂是碱金属盐,较佳的是在线性烷基中带有12-16个碳原子和在分子中带有2-6个乙二醇醚基的烷基聚乙二醇醚硫酸钠盐、线性烷基(C12-C18)磺酸钠盐、磺基琥珀酸单烷基(C12-C18)酯钠盐、硫酸盐化的脂肪酸单甘油酯钠盐,硫酸盐化的脂肪酸链烷醇酰胺、磺基乙酸烷基(C12-C16)酯、酰肌氨酸、N-酰基乙磺酸胺(acyl taurides)和酰基羟乙磺酸酯(其中酰基带有8-18个碳原子)。同样,两性离子型的,两性的,非离子型的表面活性剂也适用,如脂肪酸单和双甘油酯的乙氧基酯,脂肪酸脱水山梨醇酯的乙氧基酯和烷基(寡)葡糖苷。
另一些常见的牙膏添加剂有:
——防腐剂和抗菌物质:例如,对羟基苯甲酸甲基、乙基或丙基酯、山梨酸钠、苯甲酸钠、溴氯酚、水杨酸苯酯、缩二胍、百里酚等。
——甜味剂:例如,糖精钠、环己烷氨基磺酸钠、蔗糖、乳糖、麦芽糖、果糖。
——颜料:例如,二氧化钛。
——染料
——缓冲剂:例如,伯、仲、叔式的碱金属磷酸盐、或柠檬酸/柠檬酸钠。
——促进伤口愈合和阻止发炎的物质:例如,尿囊素、尿素、甘菊兰、母菊属活性物质及乙酰水杨酸衍生物。
下述例子用于解释本发明:
实施例
制备按本发明的牙膏(例1、2、3)和一种对照牙膏(例V)(参看表1)
表1组份 1 2 3 V沉淀硅酸Sident 12 DS 12.0 12.0 12.0 12.0沉淀硅酸Sipernat 22 LS 3.0 3.0 3.0 6.0二水合磷酸氢钙 4.0 4.0 4.0 -MgSO4·7H20 1.4 1.4 - -氟基磷酸钠/NaPO3F 0.8 0.8 0.8 0.886%甘油,德国药典(以不含水计算) 18.0 18.0 18.0 18.070%山梨糖醇,德国药典(以不含水计算) 14.0 14.0 14.0 14.0聚乙二醇(分子量:400) 2.0 2.0 2.0 2.0浓缩硅酸(FK 320 DS) 1.0 1.33 1.33 1.33黄原酸酯胶(keltrol F) 0.54 0.54 0.54 0.71二氧化钛(锐锥石型) 1.0 1.0 1.0 1.0十二烷基磺酸钠(Texapon K 1296) 1.44 1.44 1.44 1.44硅酸钠(以Na2SiO3计算) 0.06 - - -氢氧化钠 - 0.01 0.01 0.01柠檬酸(·1 H2O) 0.03 0.03 0.03 0.03糖精 0.2 0.2 0.2 -调味剂 0.8 0.8 0.8 0.8水 39.73 39.45 40.85 41.88
下述是应用的商品名:Sident 12 DS:沉淀硅酸,法兰克福DEGUSSA公司产
BET表面积: 80m2/g
夯实堆积密度:220g/lSipernat 22 LS:沉淀硅酸,法兰克福DEGUSSA公司产
BET表面积: 190m2/g
夯实堆积密度:80g/l硅酸FK 320 DS:沉淀硅酸,法兰克福DEGUSSA公司产
BET表面积: 170m2/g
夯实堆积密度:80g/lKeltrol F: 黄原酸酯胶,布鲁塞尔KELCO公司产Texapon K 1296颗粒:十二烷基硫酸钠,杜塞尔多夫HENKEL公司产
效用证明:
用本发明的牙膏(例1)和对照的牙膏(例V,不含有二水合磷酸氢钙和硫酸镁)进行下列实验:
分别从一颗人牙的牙冠(为试验牙釉)和牙根部分(为试验牙质)锯下4×5毫米的切片,表面用湿砂纸打磨,然后用磨光膏磨光至平滑。这种釉质切片又在0.1克分子浓度的含水乳酸中腐蚀6小时,该乳酸的PH值为4.6/温度=37℃,含有500mg/l羟基磷灰石。
用试验的牙膏(用水稀释1∶1)擦刷上述制备好的试样,每天二次,每次5分钟。其余时间试样贮存在37℃的CaHPO4·2H2O悬浮液中,该悬浮液由沉淀(CaCl2+Na2HPO4→CaHPO4+2NaCl)制备,每天新配制二次(早上和晚上),这种牙齿处理进行了20天。
在处理前(样片磨光后)和处理结束后拍摄了试样表面的扫描电子显微镜照片,在附图1-6中给出的是5000∶1比例的图象。
附图1:未处理过的牙釉,
附图2:未处理过的牙质,
附图3:对照牙膏V处理过的牙釉,
附图4:对照牙膏V处理过的牙质,
附图5:用例1牙膏处理过的牙釉,由此发现在表面结构的沟槽中有析出的羟基磷灰石,
附图6:用例1牙膏处理过的牙质,清楚发现牙质孔洞被析出的羟基磷灰石广泛封闭了。
Claims (9)
1.一种修复牙齿表面的牙膏,它含有磨光料,氟化物,保湿材料,稠度调节剂和水,其特征在于,它包含重量比为从10∶1至1∶1的硅酸和二水合磷酸氢钙的组合作为磨光料的组分。
2.按照权利要求1的牙膏,其特征在于它含有水溶性镁盐,该镁盐的含量要满足有0.1-0.5%重量的镁。
3.按照权利要求1或2的牙膏,其特征在于它含有作为氟化物的氟基磷酸盐,该磷酸盐的含量要满足有0.2-2%重量的PO3F-。
4.按照权利要求2的牙膏,其特征在于它含有作为氟化物的氟基磷酸镁。
5.按照权利要求3的牙膏,其特征在于它含有作为氟化物的氟基磷酸镁。
6.按照权利要求1或2的牙膏,其特征在于它含有作为磨光料的沉淀硅酸和二水合磷酸氢钙,该沉淀硅酸的平均粒度为0.5-30μ,含量为10-20%重量,该二水合磷酸氢钙的含量为1-5%重量。
7.按照权利要求3的牙膏,其特征在于它含有作为磨光料的沉淀硅酸和二水合磷酸氢钙,该沉淀硅酸的平均粒度为0.5-30μ,含量为10-20%重量,该二水合磷酸氢钙的含量为1-5%重量。
8.按照权利要求4的牙膏,其特征在于它含有作为磨光料的沉淀硅酸和二水合磷酸氢钙,该沉淀硅酸的平均粒度为0.5-30μ,含量为10-20%重量,该二水合磷酸氢钙的含量为1-5%重量。
9.按照权利要求5的牙膏,其特征在于它含有作为磨光料的沉淀硅酸和二水合磷酸氢钙,该沉淀硅酸的平均粒度为0.5-30μ,含量为10-20%重量,该二水合磷酸氢钙的含量为1-5%重量。
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DEP4237500.2 | 1992-11-06 | ||
DE4237500A DE4237500A1 (de) | 1992-11-06 | 1992-11-06 | Remineralisierendes Zahnpflegemittel |
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CN1047304C true CN1047304C (zh) | 1999-12-15 |
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US (1) | US5605677A (zh) |
EP (1) | EP0666730B1 (zh) |
JP (1) | JPH08502988A (zh) |
KR (1) | KR100295937B1 (zh) |
CN (1) | CN1047304C (zh) |
AT (1) | ATE166225T1 (zh) |
BG (1) | BG99417A (zh) |
CA (1) | CA2148909C (zh) |
CZ (1) | CZ287746B6 (zh) |
DE (2) | DE4237500A1 (zh) |
DK (1) | DK0666730T3 (zh) |
ES (1) | ES2117153T3 (zh) |
FI (1) | FI952110A0 (zh) |
HR (1) | HRP931109A2 (zh) |
HU (1) | HU218972B (zh) |
LT (1) | LT3075B (zh) |
LV (1) | LV11427A (zh) |
NO (1) | NO308933B1 (zh) |
PL (1) | PL172151B1 (zh) |
SI (1) | SI9300478A (zh) |
SK (1) | SK280006B6 (zh) |
WO (1) | WO1994010969A1 (zh) |
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US5651958A (en) * | 1995-05-02 | 1997-07-29 | The Procter & Gamble Company | Dentifrice compositions |
US5589160A (en) * | 1995-05-02 | 1996-12-31 | The Procter & Gamble Company | Dentifrice compositions |
US5658553A (en) * | 1995-05-02 | 1997-08-19 | The Procter & Gamble Company | Dentifrice compositions |
US6036944A (en) * | 1995-08-08 | 2000-03-14 | Enamelon, Inc. | Processes for the remineralization and mineralization of teeth |
US6159449A (en) * | 1997-04-03 | 2000-12-12 | Enamelon, Inc. | Dentifrice products and methods for remineralizing and/or mineralizing teeth |
EP0870493A1 (en) * | 1997-04-11 | 1998-10-14 | Carter-Wallace, Inc. | Oral gel composition comprising hydrated silica |
CN1189153C (zh) * | 1997-05-19 | 2005-02-16 | 科尔加特·帕尔莫利弗公司 | 用于牙齿再矿化的口用组合物和再矿化方法 |
DE19740453A1 (de) * | 1997-09-15 | 1999-03-18 | Henkel Kgaa | Zahnreinigungsmittel |
US6294155B1 (en) * | 1998-04-08 | 2001-09-25 | W. R. Grace & Co. -Conn. | Abrasive silica compositions and dentifrice compositions prepared therefrom |
DE19831547A1 (de) * | 1998-07-14 | 2000-01-20 | Henkel Kgaa | Flüssige Zahnreinigungsmittel |
AUPP494798A0 (en) | 1998-07-29 | 1998-08-20 | Pacific Biolink Pty Limited | Protective protein formulation |
US7625855B2 (en) * | 1999-08-11 | 2009-12-01 | Gonzalez Gustavo M | Cleaning compositions for removing organic deposits in hard to reach surfaces |
US6303104B1 (en) | 1999-02-12 | 2001-10-16 | Enamelon, Inc. | Remineralizing/mineralizing oral products having improved whitening and stain removal properties |
US6485708B1 (en) | 1999-05-13 | 2002-11-26 | Church & Dwight Co. Inc. | Products and methods for the remineralization and prevention of demineralization of teeth |
US6685920B2 (en) * | 1999-11-12 | 2004-02-03 | The Procter & Gamble Company | Method of protecting teeth against erosion |
US6174515B1 (en) | 2000-06-05 | 2001-01-16 | Amway Corporation | Toothpaste composition |
US6652611B1 (en) * | 2000-08-18 | 2003-11-25 | J. M. Huber Corporation | Method for making abrasive compositions and products thereof |
US6372198B1 (en) | 2000-09-14 | 2002-04-16 | Joseph M. Abbate | Dentifrice for the mineralization and remineralization of teeth |
KR20030017797A (ko) * | 2001-08-22 | 2003-03-04 | (주) 시온텍 | 치아우식증(충치)예방을 위한 불소이온 용출 필터소재 및그 응용방법 |
DE10223157C1 (de) * | 2002-05-24 | 2003-10-23 | Max Planck Gesellschaft | Induzierte Remineralisation von humanem Zahnschmelz |
US20070053851A1 (en) | 2003-09-09 | 2007-03-08 | Maillan Philippe E | Orally effective, essentially water-free topical agent containing one or several oxidation-sensitive substances |
US20050084461A1 (en) * | 2003-10-16 | 2005-04-21 | Winston Anthony E. | Tooth enamel rejuvenating toothpaste |
US20070258916A1 (en) * | 2006-04-14 | 2007-11-08 | Oregon Health & Science University | Oral compositions for treating tooth hypersensitivity |
US20080267891A1 (en) * | 2007-04-30 | 2008-10-30 | Colgate-Palmolive Company | Oral Care Composition To Reduce Or Eliminate Dental Sensitivity |
US20090186090A1 (en) * | 2007-04-30 | 2009-07-23 | Colgate-Palmolive | Oral Care Composition to Reduce or Eliminate Dental Sensitivity |
US7850453B2 (en) * | 2007-08-08 | 2010-12-14 | Coll Partners Ltd. | Reshapable device for fixation at a dental site |
SG175785A1 (en) | 2009-05-18 | 2011-12-29 | Colgate Palmolive Co | Oral compositions containing polyguanidinium compounds and methods of manufacture and use thereof |
US8741268B2 (en) * | 2009-09-10 | 2014-06-03 | Preventive Technologies, Inc. | Dental prophylactic paste |
TWI499430B (zh) | 2009-12-17 | 2015-09-11 | Colgate Palmolive Co | 抗侵蝕的牙膏組成物 |
EP3409324B1 (en) | 2010-01-29 | 2023-11-29 | Colgate-Palmolive Company | Oral care product for sensitive enamel care |
GB201016970D0 (en) * | 2010-10-08 | 2010-11-24 | Univ Leeds | Composition |
US20150150973A1 (en) * | 2012-03-30 | 2015-06-04 | The Royal Institution For The Advancement Of Learning/Mcgill University | Magnesium phosphate gels |
DE102013109847A1 (de) | 2013-09-09 | 2015-03-12 | Heraeus Kulzer Gmbh | Formulierungen und Kit zur biomimetischen Abscheidung von Apatit auf Zähnen |
DE102013109848A1 (de) | 2013-09-09 | 2015-03-12 | Heraeus Kulzer Gmbh | Applikationssystem zur einfachen, 3-dimensionalen Anwendung von medizinischen, kosmetischen oder Arzneimittel enthaltenden Zahnpflegeprodukten |
DE102013109846A1 (de) | 2013-09-09 | 2015-03-12 | Heraeus Kulzer Gmbh | Formulierungen und Kit zur biomimetischen Abscheidung von Apatit auf Zähnen |
US9668844B2 (en) | 2013-11-06 | 2017-06-06 | Colldent Y.A Ltd | Device for fixation at a dental site |
CA3007064C (en) * | 2015-12-10 | 2023-01-24 | The Royal Institution For The Advancement Of Learning/Mcgill University | Magnesium phosphate hydrogels |
WO2019143746A1 (en) | 2018-01-17 | 2019-07-25 | The Procter & Gamble Company | Methods and compositions to increase the hardness and resistance of enamel |
CN111658561B (zh) * | 2019-03-08 | 2023-04-11 | 湖北中部医疗科技有限公司 | 一种抗牙齿敏感牙膏及其制备方法 |
CN115339121A (zh) * | 2021-05-12 | 2022-11-15 | 华侨大学 | 一种柔性溶胶凝胶抛光块体的制备方法 |
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US4024239A (en) * | 1975-07-03 | 1977-05-17 | Lever Brothers Company | Toothpaste composition |
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US3538230A (en) * | 1966-12-05 | 1970-11-03 | Lever Brothers Ltd | Oral compositions containing silica xerogels as cleaning and polishing agents |
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US4097588A (en) * | 1975-03-11 | 1978-06-27 | National Research Development Corporation | Mineralizing dental mouthrinse |
DE2526808A1 (de) * | 1975-06-16 | 1977-01-20 | Henkel & Cie Gmbh | Fluorhaltige zahnpasta fuer druckgasverpackung |
PH12522A (en) * | 1976-02-05 | 1979-04-26 | Grace W R & Co | Oral teeth-cleaning composition |
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US4183914A (en) * | 1977-12-19 | 1980-01-15 | Abdul Gaffar | Magnesium polycarboxylate complexes and anticalculus agents |
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US5037636A (en) * | 1989-10-23 | 1991-08-06 | Monsanto Chemical Company | Fluoride stability in dicalcium phosphate dihydrate composition |
-
1992
- 1992-11-06 DE DE4237500A patent/DE4237500A1/de not_active Withdrawn
-
1993
- 1993-08-09 HR HR931109A patent/HRP931109A2/hr not_active Application Discontinuation
- 1993-09-16 SI SI9300478A patent/SI9300478A/sl unknown
- 1993-10-28 KR KR1019950700803A patent/KR100295937B1/ko not_active IP Right Cessation
- 1993-10-28 CZ CZ19951172A patent/CZ287746B6/cs not_active IP Right Cessation
- 1993-10-28 EP EP93923565A patent/EP0666730B1/de not_active Expired - Lifetime
- 1993-10-28 US US08/433,391 patent/US5605677A/en not_active Expired - Fee Related
- 1993-10-28 DE DE59308590T patent/DE59308590D1/de not_active Expired - Lifetime
- 1993-10-28 DK DK93923565T patent/DK0666730T3/da active
- 1993-10-28 PL PL93308767A patent/PL172151B1/pl not_active IP Right Cessation
- 1993-10-28 ES ES93923565T patent/ES2117153T3/es not_active Expired - Lifetime
- 1993-10-28 JP JP6511652A patent/JPH08502988A/ja active Pending
- 1993-10-28 HU HU9501325A patent/HU218972B/hu not_active IP Right Cessation
- 1993-10-28 SK SK565-95A patent/SK280006B6/sk unknown
- 1993-10-28 WO PCT/EP1993/002991 patent/WO1994010969A1/de active IP Right Grant
- 1993-10-28 AT AT93923565T patent/ATE166225T1/de not_active IP Right Cessation
- 1993-10-28 CA CA002148909A patent/CA2148909C/en not_active Expired - Lifetime
- 1993-11-05 LT LTIP1437A patent/LT3075B/lt not_active IP Right Cessation
- 1993-11-05 CN CN93114226A patent/CN1047304C/zh not_active Expired - Fee Related
-
1995
- 1995-01-20 NO NO950229A patent/NO308933B1/no not_active IP Right Cessation
- 1995-02-13 BG BG99417A patent/BG99417A/bg unknown
- 1995-05-03 FI FI952110A patent/FI952110A0/fi unknown
- 1995-05-05 LV LV950124A patent/LV11427A/xx unknown
Patent Citations (4)
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US4024239A (en) * | 1975-07-03 | 1977-05-17 | Lever Brothers Company | Toothpaste composition |
US4348382A (en) * | 1980-12-05 | 1982-09-07 | Colgate-Palmolive Company | Dentifrice composition |
US4425324A (en) * | 1981-05-11 | 1984-01-10 | Colgate-Palmolive Company | Hazed toothpaste |
US4565692A (en) * | 1983-12-23 | 1986-01-21 | Colgate-Palmolive Company | Extrudable dentifrice |
Also Published As
Publication number | Publication date |
---|---|
DK0666730T3 (da) | 1999-03-08 |
EP0666730B1 (de) | 1998-05-20 |
NO950229D0 (no) | 1995-01-20 |
FI952110A (fi) | 1995-05-03 |
FI952110A0 (fi) | 1995-05-03 |
SK56595A3 (en) | 1997-01-08 |
CA2148909C (en) | 2003-06-10 |
CN1090751A (zh) | 1994-08-17 |
LV11427A (lv) | 1996-08-20 |
US5605677A (en) | 1997-02-25 |
CZ287746B6 (en) | 2001-01-17 |
HRP931109A2 (en) | 1995-06-30 |
NO950229L (no) | 1995-01-20 |
LT3075B (en) | 1994-11-25 |
JPH08502988A (ja) | 1996-04-02 |
HU218972B (hu) | 2001-01-29 |
PL172151B1 (pl) | 1997-08-29 |
HUT70078A (en) | 1995-09-28 |
EP0666730A1 (de) | 1995-08-16 |
WO1994010969A1 (de) | 1994-05-26 |
KR100295937B1 (ko) | 2001-11-14 |
HU9501325D0 (en) | 1995-06-28 |
PL308767A1 (en) | 1995-08-21 |
CZ117295A3 (en) | 1995-11-15 |
BG99417A (bg) | 1995-06-30 |
CA2148909A1 (en) | 1994-05-26 |
ES2117153T3 (es) | 1998-08-01 |
SI9300478A (en) | 1994-06-30 |
SK280006B6 (sk) | 1999-07-12 |
ATE166225T1 (de) | 1998-06-15 |
LTIP1437A (en) | 1994-05-15 |
DE59308590D1 (de) | 1998-06-25 |
DE4237500A1 (de) | 1994-05-11 |
NO308933B1 (no) | 2000-11-20 |
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