CN106999393B - 用于牙齿美白的口腔组合物 - Google Patents
用于牙齿美白的口腔组合物 Download PDFInfo
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- CN106999393B CN106999393B CN201480084070.8A CN201480084070A CN106999393B CN 106999393 B CN106999393 B CN 106999393B CN 201480084070 A CN201480084070 A CN 201480084070A CN 106999393 B CN106999393 B CN 106999393B
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Abstract
一种牙齿美白口腔护理组合物,其通过将包括水溶性美白薄膜的薄片、在CIELAB体系中具有在200度至320度范围内的色调角的染料和口腔可接受的载体媒介的成分合并而制备。所述水溶性美白薄膜的所述薄片包含:(a)含羟烷基纤维素的成膜聚合物,其中所述羟烷基纤维素具有约1毫帕秒(mPa.s)至约1000毫帕秒的粘度,如在20℃下使用乌式管粘度计以所述成膜聚合物的2重量%水溶液所测定;和(b)在CIELAB体系中具有在200度至320度范围内的色调角的颜料。
Description
背景技术
本公开涉及一种用于美白牙齿的口腔护理组合物。
许多人并不满意他们现在的牙齿颜色。因此,希望可通过使用牙齿美白产品来实现的更白的牙齿。美白效果可通过在化学上改变或移除污垢和/或改变牙齿颜色的视觉感知来产生。
在文献中已知的是,对白色物质的视觉感知可通过光学增亮剂、蓝色颜料或蓝色染料的沉积来改变,所述光学增亮剂、蓝色颜料或蓝色染料尤其是反射光或发射光的色调角(在CIELAB标度中的色调角)在200度至320度之间的一种。这种效果常用于衣物洗涤剂产品中以便使得白色衣物对人眼来讲呈现为“更白的”。
相同概念已被应用于牙齿美白。牙齿的自然灰白色或黄色可通过在牙齿上沉积蓝色物质而呈现为更白的。EP1935395B1中公开了在牙膏中使用具有沉积助剂的颜料来使得牙齿看上去更白,所述沉积助剂诸如为(马来酸酐与甲基乙烯基醚的共聚物)或羟丙基甲基纤维素。
染料在本领域中也已知用于美白牙齿。例如,美国专利6,030,222公开了当与载体共混时在牙齿上沉积染料以实现美白。美国专利申请公布2012/0093905公开了与某些聚合物偶合的染料以用于美白牙齿。然而,染料具有与颜料明显不同的性质。具体地讲,染料在水中的溶解性远高于颜料。染料的溶解性使得它们在水合环境中沉积并保持在牙齿上要更困难,如例如在EP1935395B1中所述。
本领域中新增另外的牙齿美白组合物将是受人欢迎的。
发明内容
本公开的实施方案涉及一种牙齿美白口腔护理组合物。该口腔护理组合物通过将包括水溶性美白薄膜的薄片、在CIELAB体系中具有在200度至320度范围内的色调角的染料和口腔可接受的载体媒介的成分合并而制备。水溶性美白薄膜的薄片包含:(a)含羟烷基纤维素的成膜聚合物,其中羟烷基纤维素具有约1毫帕秒(mPa.s)至约1000毫帕秒的粘度,如在20℃下使用乌式管粘度计以成膜聚合物的2重量%水溶液所测定;和(b)在CIELAB体系中具有在200度至320度范围内的色调角的颜料。
由下文所提供的详细说明,本发明的其他适用领域将变得显而易见。应了解,详细说明和特定实例虽然指示本发明的优选实施方案,但旨在仅用于说明的目的而无意限制本发明的范围。
具体实施方式
以下对于优选实施方案的描述在性质上仅是示例性的,并且绝不应限制本发明、其应用或用途。
通篇使用的范围用作描述范围内的每个值的简略表达方式。范围内的任何值可选为范围终点。另外,本文引用的所有参考文献据此全文以引用方式并入。如果本公开中的定义和所引用参考文献的定义发生冲突,则以本公开为准。
除非另外规定,否则本文和在本说明书中其他处表达的所有百分比和量应理解为是指重量百分比。给定的量是基于材料的活性重量计。
本公开的实施方案涉及一种牙齿美白口腔护理组合物。该组合物通过将包括水溶性聚合物薄片、在CIELAB体系中具有在约200度至约320度范围内的色调角的至少一种染料和口腔可接受的载体媒介的成分合并而制备。水溶性聚合物薄片包含:(a)含羟烷基纤维素的成膜聚合物,其中羟烷基纤维素具有约1毫帕秒(mPa.s)至小于约1000毫帕秒的粘度,如在20℃下使用乌式管粘度计以聚合物的2重量%水溶液所测定;和(b)在CIELAB体系中具有在约200度至约320度范围内的色调角的至少一种颜料。
含颜料的薄片
薄片可以按所需的方式制备。在一个实施方案中,薄片可由水溶性薄膜制成,在本文有时也称为“薄膜薄片”。该薄片包含基质材料,基质材料包含水溶性羟烷基纤维素聚合物,而颜料则分散在该聚合物中。在制备根据本公开的薄膜薄片中,将羟烷基纤维素和颜料溶于可相容的溶剂(例如,水、乙酸乙酯、丙酮、诸如乙醇的醇,或其混合物)中以形成成膜组合物。任选地,可添加其他成分,例如,风味剂、湿润剂(例如,丙二醇)、表面活性剂(例如,Tween 80)、甜味剂、活性剂等等。任选成分可存在于薄膜中,存在于口腔组合物的非薄膜部分中或两者中,下文提供此类任选成分的更详细描述。将成膜组合物浇注在可释放的载体上并且干燥以形成薄膜基质材料片。载体材料必须具有一定的表面张力,该表面张力允许薄膜溶液在整个预期载体宽度上均匀分布,而不浸泡来在薄膜与载体衬底之间形成破坏键。适合的载体材料的实例包括玻璃、不锈钢、特氟隆和聚乙烯浸渍的纸。可在高温下使用干燥烘箱、干燥终端、真空干燥器或任何其他适合的干燥设备来进行薄膜的干燥,所述干燥设备不会不利地影响构成薄膜的成分。
可以采用任何合适的薄膜厚度。合适的厚度的实例在约1密耳至约5密耳、或约1密耳至约4密耳、或约1.5密耳至约5密耳、或约1.5密耳至约3密耳、或约2密耳至约3密耳或约2密耳的范围内。
一旦形成薄膜,就由薄膜来制成薄膜薄片,例如通过将薄膜冲压或切割成各种成形薄片来制成,所述成形薄片诸如为心形、正方形、矩形、三角形、星形、菱形、圆形等等。任选地,可使用本领域中已知的常规研磨技术将薄膜研磨成不规则形状。在一个实施方案中,薄膜薄片的粒度使得大于90%的颗粒都通过50目过滤器。在一些实施方案中,粒度在30目至100目之间,或在30目至80目之间,或在50目至80目之间。薄膜薄片相对于口腔组合物的总重量按以下浓度掺入本公开的口腔组合物中:约0.05重量%至5.0重量%,诸如约0.05重量%至2重量%,在另一个实施方案中约0.05重量%至1重量%,以及在另一个实施方案中约0.1重量%至约0.5重量%。
本公开的薄膜薄片具有快速溶解速率,例如,约30秒或更短,在另一个实施方案中约1秒至30秒,在另一个实施方案中约1秒至25秒,在另一个实施方案中约1秒至20秒,在另一个实施方案中约2秒至15秒。出于本公开的目的,溶解速率定义为:薄膜薄片在刷牙过程中崩解并释放出可观察到的颜色所花的平均时长,如在包括8名或更多名使用包含薄膜薄片的牙膏的受试者的体内研究中所测定。
用于制备本公开的薄膜基质的成膜聚合物是水溶性羟烷基纤维素,诸如羟丙基甲基纤维素、羟乙基丙基纤维素和羟丁基甲基纤维素。烷基可以是例如C1-5烷基,诸如C1-4烷基。成膜纤维素聚合物是低粘度聚合物。低粘度意思是粘度在约1毫帕秒(mPa.s)至小于约1000毫帕秒的范围内,如在20℃下使用乌式管粘度计以聚合物的2重量%水溶液所测定。在更特定实施方案中,聚合物的粘度在20℃为约1mPa.s至约100mPa.s、更具体地讲约1mPa.s至约20mPa.s并且在特定实施方案中约1mPa.s至约10mPa.s。在优选实施方案中,羟烷基纤维素聚合物是羟丙基甲基纤维素聚合物(HPMC)。
HPMC可以商标名称Methocel E5 LV购自Dow Chemical Company。Methocel E5 LV是USP级的低粘度HPMC,其具有29.1%的甲氧基基团和9%的羟丙基基团取代。它为白色或灰白色自由流动的干燥粉末。如利用乌式管粘度计以2重量%水溶液所测量,它在20℃下具有5.1mPa.s的粘度。
羟烷基纤维素以在薄膜的约10重量%至约80重量%并优选地约30重量%至约60重量%范围内的量掺入薄膜中。按组合物的重量计,羟烷基纤维素聚合物以例如约0.01%至约10%,诸如约0.05%至约5%,或约0.1%至约1%的量掺入口腔组合物中。
如在共同待审的申请No.PCT/US2013/77373(其公开内容全文以引用方式并入本文)中所讨论,HPMC聚合物能够在掺入洁齿剂配方中时将蓝色颜料递送到牙齿。然而,当HPMC在本公开的薄片中与蓝色颜料预混并浓缩时,HPMC递送蓝色颜料的能力似乎增强。当薄片溶解时,蓝色颜料和HPMC在薄膜薄片中保持在一起直到刷动时。
在一个实施方案中,按本公开的口腔组合物的重量计,薄膜薄片占约0.01%至约5%或更多,诸如约0.015%至约5%,或约0.015%至约3%。
本公开的薄膜基质在使用期间溶解在水或水溶液(诸如唾液)中。在刷牙期间,机械动作有助于薄膜薄片的破裂,这使得薄膜薄片更易于溶解在水性环境中。在本公开的上下文中,“可溶性”羟烷基纤维素是可溶于水的材料。例如,按重量计,在25℃下,羟烷基纤维素可具有0.5%或更大,诸如5%或更大的溶解性。另外,这样的材料在从溶液状态干燥后保持可溶性,也就是说,其可在干燥后再次溶解。此类材料是成膜聚合物。需要水溶性以便避免聚合物堆积在牙齿上。
羟烷基纤维素聚合物是沉积助剂。也就是说,它能够增强颜料在牙齿上的沉积或放置,并因而增强由颜料导致的颜色变化。
可以采用任何合适量的颜料。口腔组合物中颜料的量可以为例如约0.01重量%至约0.3重量%、更具体地讲约0.02重量%至约0.1重量%并且更具体地讲约0.03重量%至约0.08重量%。颜料可在整个组合物中均匀分布,或颜料可分散于第二相(例如,单独的部分)中,诸如分散于条带或其他共挤出的第二相中。这种“双相”组合物具有的优点在于,各相可为不同的颜色,从而向消费者呈现视觉上更引入注意的产品。
在一个实施方案中,颜料具有蓝绿色或紫红色颜色,诸如蓝绿色至蓝紫色,或蓝色。已知适用于本公开的配方的颜料在Colour Index International中列出。此类颜料的实例以颜料紫1直至颜料紫56和颜料蓝1至83来列出。颜料紫的实例是颜料紫1、1:1、1:2、2、3、5:1、13、19、23、25、27、31、32、37、39、42、44和50。颜料蓝的实例是颜料蓝1、2、9、10、14、15、15:1、15:2、15:3、15:4、15:6、16、18、19、24:1、25、56、60、61、62和66。其他适合的颜料是颜料群青蓝和群青紫。颜料可在CIELAB体系中具有约200度至约320度诸如约250度与约290度之间的色调角h。对色调角的详细描述可在由Wiley-VCH出版的H.Zollinger著的ColourChemistry第3版的第57页上找到。
虽然优选的单一颜料是蓝色或紫色的,但是可通过混合在这个h范围外的颜料来实现相同的效果;例如,这个色调角也可通过将红色颜料和蓝色颜料混合以产生蓝色或蓝紫色着色颜料而获得。在一个实施方案中,颜料是颜料蓝15,诸如颜料蓝15:1、15:2、15:3、15:4、15:5或15:6中的一种或多种。颜料蓝15:1-15:6系列的色调角和颜色如在“ThePorphyrin Handbook”第19卷,Applications of Phthalocyanines,第133-134页中所述而定义,该文献的公开内容据此全文以引用方式并入。颜料可以能够反射足够的光以使得可感知到所处理的牙齿比其初始颜色更白。优选地,颜料是有色的以使得其天然颜色在紫红色至绿蓝色内,诸如从紫色至蓝色。
在一个实施方案中,除了绿蓝色至紫红色颜料外,还使用红色颜料。如果使用红色颜料,则红色染料可按约0.1∶1至约1∶1的红色颜料∶绿蓝色至紫红色颜料的重量比存在,比如约0.1∶1至约1∶1的红色颜料∶蓝色颜料比。红色颜料的实例包括红30、红40等等。
颜料通常应被理解成改变反射光的颜色并且在相关温度下不溶于相关介质中的材料。这与可溶性染料形成对比。在本公开的上下文中,“相关介质”是人类唾液(或许与水混合),它是组合物所用到的液体介质,并且“相关温度”是在刷牙过程中的口腔温度,诸如高达约37℃。作为合理的近似,相关介质可被视为水且相关温度为25℃。
薄膜薄片中的羟烷基纤维素有助于颜料在牙齿上沉积,以使得与用对照配方以等效方式处理的牙齿所获得的值相比,牙齿表面美白度提高至少20%,更优选地至少100%,所述对照配方在不存在羟烷基纤维素的情况下使用相同量的颜料。在实施例中描述用于测定牙齿美白度的方法。
Δb*是沿黄-蓝轴的颜色改变的量值,负Δb*对应于降低的黄度。
染料
将染料与本公开的颜料组合物一起使用以实现改善的美白并不是简单的事情。这至少是因为染料与颜料的性质明显不同。具体地讲,染料在水中的溶解性远高于颜料。染料的溶解性使得它们沉积并保持在牙齿上要更困难,特别是在具有约20重量%至约30重量%的水或更多的水的水含量相对高的配方中。例如,EP1935395(其公开内容全文以引用方式并入本文)讨论了在染料从牙齿洗掉的情况下将染料用作美白剂可能是无效的。诸如PVM/MA的聚合物已用于帮助将蓝色染料沉积在牙齿上。
本公开的颜料配方在另一方面采用水溶性聚合物薄片。薄片在刷动下溶解,并且据发现有助于将颜料沉积在牙齿表面上。配方中相对高含量的水使得薄片在施加到牙齿的过程中(诸如在刷牙过程中)快速溶解。这是因为配方中的含水量虽然不足以实质性溶解薄片,但是接近溶解点,以使得在刷牙过程中当将水和/或唾液引入时,薄片快速溶解。用在这些配方中的高含量的水通常认为与染料的使用不相容,特别是在不存在聚合物粘合剂助剂诸如PVM/MA的情况下。然而,申请人已出人意料地发现,染料与本公开的颜料的组合可使美白效果强于单独的颜料或染料。
在本公开的组合物中使用的染料可以是将会提供所需美白效果的任何染料。在一个实施方案中,染料在CIELAB体系中具有约200度至约320度诸如约250度至约290度的色调角h。色调角的详细说明可见于由Wiley-VCH(2001)出版的H.Zollinger编著的ColorChemistry(Synthesis,Properties,and Applications of Organic Dyes and Pigments)第3版第57页。在一个实施方案中,染料具有蓝色至蓝紫色。虽然优选的单一染料是蓝色或紫色的,但是可通过混合在这个h范围外的染料来实现相同的效果;例如,这个色调角也可通过将红色染料和蓝色染料混合以产生蓝色或蓝紫色着色染料而获得。染料可以能够反射足够的光以使得人眼感知到所处理的牙齿比其初始颜色更白。例如,用于实现这一效果的染料可以是有色的以使得其天然颜色在紫红色至绿蓝色内,诸如从紫色至蓝色。
如上所述,染料是水溶性的。在这种特定情形中,术语“水溶性的”通常意思是染料具有在25℃下至少10g/L、最优选地在25℃至少100g/L的水溶解度(其中溶解度在未缓冲的蒸馏水中测定)。三芳基甲烷染料是适用于本公开的组合物的水溶性染料的实例。在一些实施方案中,适用于本文中的染料是阴离子三苯基甲烷染料,尤其是含有两个至四个磺酸根基团的二氨基三苯基甲烷染料,诸如对应于通式(I)的那些染料:
其中R1、R2、R3和R4是一价部分,其各自独立地选自氢(-H)、羟基(-OH)、卤素(例如-Cl)和磺酸根(-SO3 -)基团,前提条件是R1至R4中的至少两个是磺酸根基团。
本文中适用的染料的实例是FD&C蓝#1(也称为亮蓝FCF(蓝1))以及对应于通式(I)的其他商业名称,其中R2为-H并且R1、R3和R4为磺酸根基团。FD&C蓝#1(CAS号[3844-45-9])是引起食品和其他物质的颜色变化的着色剂。它由E数E133表示并且具有42090的颜色指数(CI 42090)。它具有淡红蓝色粉末的外观。它可溶于水,并且溶液在约628纳米的波长下具有最大吸收。它是使用来自石油的芳族烃产生的合成染料。它通常为二钠盐。二铵盐(D&C蓝#4)具有CAS号[2650-18-2]。钙盐和钾盐也是已知的。适用于本文的其他染料为FD&C蓝#2(靛胭脂,CI 73015,CAS号[860-22-0])、CI食品蓝5(CI 42051;也称为酸性蓝3,CAS号[3536-49-0])、酸性蓝1(CI 42045,CAS号[129-17-9])等。在一些实施方案中,染料为FD&C蓝#1、FD&C蓝#2、D&C蓝#4、CI食品蓝5、酸性蓝1或其混合物。
也可使用染料的混合物,甚至当单种染料具有在所需范围之外的色调角时,只要染料的混合物将在该范围内即可。例如,可以使用红色染料,例如FD&红#3、FD&C红#40等。在一个实施方案中,FD&C蓝#1与FD&C红#40结合使用。
可将任何合适量的染料用于口腔护理组合物中。示例量可以为约0.001重量%至约2重量%、约0.002重量%至约1.5重量%、约0.003重量%至约1.25重量%、约0.004重量%至约1重量%、约0.005重量%至约0.5重量%、约0.0075重量%至约0.25重量%、约0.01重量%至约0.1重量%、约0.02重量%至约0.07重量%或约0.03重量%至约0.05重量%。在一些实施方案中,染料在口腔护理组合物中的量为约0.03重量%。在一些实施方案中,染料在口腔护理组合物中的量为约0.05重量%。染料可在整个组合物中均匀分布,或染料可分散于第二相或部分中,诸如分散于条带或其他共挤出的第二相中。这种“双相”组合物具有的优点在于,各相可为不同的颜色,从而向消费者呈现视觉上更引入注意的产品。
美白增强粘合材料
已令人惊讶地发现,许多成分当存在于本公开的组合物中时会增加染料沉积、附着和伴随的牙齿美白。此类成分在本文称为“美白增强生物粘合材料”。
在本公开的组合物中,这些美白增强生物粘合材料可以是磷酸化丙烯酸共聚物、或乙烯基醚与马来酸或马来酸酐的共聚物。在一些实施方案中,乙烯基醚与马来酸或马来酸酐的共聚物为乙烯基甲基醚与马来酸的共聚物(“PVM/MA”)。不同于使用染料和粘合材料的现有技术组合物,在本公开的组合物中,染料不共价键合到美白增强生物粘合材料(参见例如美国专利申请公布2012/0093905)。也就是说,可能的是,羟烷基纤维素用作本公开组合物中的染料的生物粘合剂。因此,在一个实施方案中,口腔护理组合物不含超过微量的生物粘合剂聚合物,其中生物粘合剂聚合物不同于羟烷基纤维素。
本公开的美白增强材料可有助于染料沉积到牙齿上,以使得与用对照配方以等效方式处理的牙齿所获得的美白度值相比,牙齿表面美白度提高至少20%或至少100%或至少400%,所述对照配方在不存在美白增强材料的情况下使用相同量的染料。在实施例中描述用于测定牙齿美白度的方法。
在一些实施方案中,乙烯基醚与马来酸或马来酸酐的共聚物在组合物中的量为0.001重量%至10重量%、0.01重量%至6重量%、0.01重量%至5重量%、0.05重量%至5重量%、0.1重量%至5重量%、0.5重量%至5重量%、1重量%至4重量%、1重量%至2重量%共聚物、或约2重量%。本公开的其他组合物包含0.3重量%至0.8重量%的共聚物,更具体地讲包含0.3重量%至0.6重量%的共聚物。
在一个实施方案中,美白增强材料是乙烯基甲基醚与马来酸的共聚物。在一些实施方案中,此类共聚物为马来酸与甲基乙烯基醚的1∶4至4∶1共聚物,其分子量(MW)为30,000道尔顿至1,000,000道尔顿、最优选地30,000道尔顿至500,000道尔顿。这些共聚物可例如作为系列共聚物而获得。尤其优选的共聚物包括S-96和S-97,其可以粉末和溶液的形式获得。当使用溶液形式时,可添加适当计算的较高的量,以使得可以维持活性成分的水平。
在一个实施方案中,美白增强材料是磷酸化丙烯酸聚合物。在一些实施方案中,组合物包含0.001重量%至10重量%、0.01重量%至6重量%、0.01重量%至5重量%、0.05重量%至5重量%、0.1重量%至5重量%、0.5重量%至5重量%、1重量%至4重量%、1重量%至2重量%的共聚物、或约2重量%的磷酸化丙烯酸聚合物。
在一个实施方案中,仅微量的、或无任何本文所述的美白增强生物粘合剂材料被包含在本公开的配方中。出于本公开的目的,术语“微量”定义为相对于组合物的总重量而言低于0.0001重量%。
口腔可接受的载体媒介
本公开的口腔护理组合物包含将薄膜薄片掺入其中的媒介或基料。口腔可接受的载体媒介的实例包括载体聚合物、湿润剂、水、磨料、增稠剂诸如二氧化硅或其两种或更多种的任何组合。术语“口腔可接受的”指的是可在正常使用期间以安全方式用到或施加到口腔的聚合物或成分。
载体聚合物
载体聚合物可包括一种或多种阴离子或非离子聚合物,并且还可包括另外的聚合物以调整配方的粘度或增强其他成分的溶解度。
适合的载体聚合物包括聚乙二醇、多糖(例如,纤维素衍生物,例如羧甲基纤维素;或多糖胶,例如黄原胶或角叉菜胶)。酸性聚合物(例如聚丙烯酸酯凝胶)可以其游离酸或者部分或完全中和的水溶性碱金属(例如钾和钠)或铵盐的形式提供。本文中适用的阴离子聚合物可增强水溶性美白复合物的效果,所述阴离子聚合物的量例如为组合物的约0.001%至约5%、更具体地讲约0.01%至5%、更具体地讲约0.05%至4%、更具体地讲约0.05%至3%。此类试剂的实例在美国专利No.5,188,821和5,192,531中进行了教导;并且包括合成的阴离子聚合聚碳酸酯,诸如马来酸酐或马来酸与另一可聚合烯属不饱和单体的1∶4至4∶1共聚物,优选具有约30,000至约1,000,000、最优选约300,000至约800,000的分子量(M.W.)的甲基乙烯基醚/马来酸酐。这些共聚物可例如作为获得,例如,可得自ISPTechnologies,Inc.,Bound Brook,N.J.08805的AN 139(M.W.500,000)、AN 119(M.W.250,000)和优选的S-97药物级(M.W.700,000)。其他起作用的聚合物包括诸如马来酸酐与丙烯酸乙酯、甲基丙烯酸羟乙酯、N-乙烯基-2-吡咯烷酮或乙烯的1∶1共聚物的那些,后者可例如以Monsanto EMA编号1103、M.W.10,000以及EMA等级61获得;以及丙烯酸与甲基丙烯酸甲酯或甲基丙烯酸羟乙酯、丙烯酸甲酯或丙烯酸乙酯、异丁基乙烯醚或N-乙烯基-2-吡咯烷酮的1∶1共聚物。一般来讲,适合的是含有活性碳-碳烯属双键和至少一个羧基的聚合的烯属或烯系不饱和羧酸,即含有因为在相对于羧基的α-β位置中或作为未端亚甲基群组的一部分存在于单体分子中而容易在聚合中起作用的烯属双键的酸。此类酸的例证为丙烯酸、甲基丙烯酸、乙基丙烯酸、α-氯代丙烯酸、巴豆酸、β-丙烯酰氧基丙酸、山梨酸、α-氯代山梨酸、肉桂酸、β-苯乙烯基丙烯酸、粘糠酸、衣康酸、柠康酸、中康酸、戊烯二酸、乌头酸、α-苯基丙烯酸、2-苯甲基丙烯酸、2-环己基丙烯酸、当归酸、伞形酸、富马酸、马来酸以及酸酐。可与此类含羧基单体共聚的其他不同的烯属单体包括乙烯基乙酸酯、氯乙烯、马来酸二甲酯等。共聚物可包含对于水溶性来讲足够的含羧基盐基团。另一类聚合剂包括含有取代丙烯酰胺的均聚物和/或不饱和磺酸及其盐的均聚物的组合物,特别地其中聚合物是分子量为约1,000至约2,000,000的基于选自丙烯酰胺基烷基磺酸(诸如2-丙烯酰胺2甲基丙烷磺酸)的不饱和磺酸,其在授予Zahid的于1989年6月27日的美国专利No.4,842,847(全文以引用方式并入本文)中进行了描述。另一类适用的聚合剂包括含有成比例的阴离子表面活性氨基酸的聚氨基酸,所述氨基酸诸如为天冬氨酸、谷氨酸和磷酸丝氨酸(除碱性氨基酸聚合物之外),例如,如授予Sikes等人(全文以引用方式并入本文)的美国专利No.4,866,161中所公开。
在制备口腔护理组合物中,有时必须添加一些增稠材料来提供合乎需要的稠度或者稳定或增强配方的性能。在某些实施方案中,增稠剂是羧基乙烯基聚合物、角叉菜胶、羟乙基纤维素和纤维素醚的水溶性盐,诸如羧甲基纤维素钠和羧甲基羟乙基纤维素钠。羟烷基甲基纤维素也可存在于口腔组合物的非薄膜部分中。也可将天然胶诸如刺梧桐胶、阿拉伯树胶和黄芪胶掺入。胶态硅酸镁铝或细分二氧化硅可用作增稠组合物的组分以便进一步改善组合物的质地。在某些实施方案中,使用量为总组合物的约0.05重量%至5重量%、更具体地讲约0.5重量%至5重量%的增稠剂。用于本公开的口腔可接受的载体聚合物可以为水溶性的。适用于本公开的口腔可接受的载体聚合物通常将在25℃的温度下在水中溶解或分散。除薄膜薄片中的羟烷基甲基纤维素之外,某些口腔可接受的载体聚合物也能够帮助颜料在牙齿上的沉积,以使得牙齿表面美白得以增强。
无论增强剂、沉积助剂、增稠剂等等还是其组合,本公开的组合物中的口腔可接受的载体媒介聚合物的量适合在约0.001%至约10%、更具体地讲约0.005%至约5%、更具体地讲约1%至约5%并且更具体地讲约1%至约3%的范围内。
湿润剂
在口腔组合物的某些实施方案内,掺入湿润剂来防止组合物在暴露于空气之后硬化也是合乎需要的。某些湿润剂也可将合乎需要的甜味或风味赋予洁齿剂组合物。以纯的湿润剂计,湿润剂通常在一个实施方案中占洁齿剂组合物的约15%至约70%或在另一个实施方案中占约30%至约65%。适合的湿润剂包括可食用的多羟基醇,诸如甘油、山梨糖醇、木糖醇、丙二醇以及其他多元醇和这些湿润剂的混合物。甘油和山梨糖醇的混合物可用于某些实施方案以作为本文中的牙膏组合物的湿润剂组分。
磨料
组合物可包含磷酸钙磨料,例如,磷酸三钙(Ca3(PO4)2)、羟磷灰石(Ca10(PO4)6(OH)2)或磷酸二钙二水合物(CaHPO4·2H2O,本文中也有时称为DiCal)或焦磷酸钙。除了磷酸钙磨料外还可使用的或可代替磷酸钙磨料使用的其他磨料包括例如二氧化硅磨料,诸如具有最多约20微米的平均粒度的沉淀二氧化硅,诸如由J.M.Huber出售的Zeodent其他适用的磨料也包括偏磷酸钠、偏磷酸钾、硅酸铝、煅烧氧化铝、膨润土或其他硅质材料或其组合。本文中适用的二氧化硅磨料抛光材料以及其他磨料通常具有在约0.1微米与约30微米之间、在约5微米与约15微米之间的范围内的平均粒度。二氧化硅磨料可来自沉淀二氧化硅或二氧化硅凝胶,诸如在授予Pader等人的美国专利No.3,538,230和授予Digiulio的美国专利No.3,862,307中所述的二氧化硅干凝胶,两篇专利均以引用方式并入本文。特定的二氧化硅干凝胶由W.R.Grace&Co.Davison Chemical Division以商标名出售。沉淀二氧化硅材料包括由J.M.Huber Corp.以商标名出售的那些,包括带有标示Zeodent 115和119的二氧化硅。这些二氧化硅磨料在授予Wason的美国专利No.4,340,583中有所描述,该专利以引用方式并入本文。在某些实施方案中,适用于口腔护理组合物的实践的磨料材料包括二氧化硅凝胶和沉淀非晶形二氧化硅,其具有小于约100cc/100g二氧化硅并且在约45cc/100g二氧化硅至约70cc/100g二氧化硅范围内的吸油值。吸油值使用ASTA Rub-Out Method(擦掉法)D281来测量。在某些实施方案中,二氧化硅是具有约3微米至约12微米和约5微米至约10微米的平均粒度的胶态颗粒。市售低吸油量二氧化硅磨料的实例以商标名Sylodent 由W.R.Grace&Co.,Baltimore,Md.21203的DavisonChemical Division销售。Sylodent 650是低吸油量二氧化硅磨料的实例,其为由胶态二氧化硅的颗粒构成的二氧化硅水凝胶,所述颗粒具有的水含量为29重量%,直径平均为约7微米至约10微米,并且吸油量低于约70cc/100g二氧化硅。磨料以例如约10重量%至约60重量%,在其他实施方案中约20重量%至约45重量%,以及在另一个实施方案中约30重量%至约50重量%的浓度存在于口腔护理组合物中。
水
水也存在于本公开的口腔组合物中。用于商业口腔组合物的制备的水可以为去离子的并且不含有机杂质。按口腔组合物的重量计,水的量可在18%或更多,诸如约20%至约35%,诸如约20%至约30%的范围内。该量的水包括所添加的游离水加上与如山梨糖醇或本公开的任何组分的其他材料一起引入的量的水。在一个实施方案中,不包括添加的水。
产品形式
用于本公开的组合物的适合产品形式的实例包括洁齿剂、口香糖和锭剂。
本公开的产品形式的类型是洁齿剂。术语“洁齿剂”通常表示用于清洁口腔的表面的配方。洁齿剂为不是故意吞下达到治疗剂的全身施用的目的而是施加到口腔用于处理口腔并随后吐出的口腔组合物。洁齿剂可与诸如牙刷的清洁工具结合使用,通常通过将洁齿剂施加到牙刷的刷毛并随后刷动口腔的可接近表面来使用。优选地,洁齿剂呈糊剂或凝胶(或其组合)的形式。
活性剂
在本文中供任选使用的活性成分的有效浓度将取决于所使用的特定药剂和递送系统。应当理解的是,牙膏可在使用时用水稀释。浓度还将取决于所选择的确切的盐或聚合物。例如,在以盐形式提供活性剂的情况下,抗衡离子将影响盐的重量,以使得如果抗衡离子较重,则将需要以重量计更多的盐来在最终产品中提供相同浓度的活性离子。活性剂可包括氟离子源、防牙结石剂、氨基酸、美白剂、抗菌剂等等中的一种或多种。
当存在时,精氨酸可以例如约0.1重量%至约20重量%(表示为游离碱的重量)的水平存在,例如,针对消费者牙膏来说约1重量%至约10重量%,或针对专业或处方治疗产品来说,约7重量%至约20重量%。
抗菌剂可包含在本公开的口腔组合物中,并且尤其是根据有效性和安全性的考虑是合乎需要的非阳离子卤代二苯基醚药剂,所述药剂诸如为2′,4,4′三氯-2羟基-二苯基醚(三氯生)和2,2′-二羟基-5,5′二溴苯基醚。当存在于口腔组合物中时,抗菌剂以约0.05重量%至约2重量%并优选地0.1重量%至约1重量%的浓度存在。抗菌剂的水平将发生变化。举例来说,三氯生牙膏可含有约0.3重量%的三氯生。
用于降低牙齿敏感度的药剂也可以约0.1重量%至约10重量%的浓度包含在本公开的口腔组合物,所述药剂诸如为氯化钾、硝酸钾和柠檬酸钾。
氟离子源
口腔护理组合物还可以包含一种或多种氟离子源,例如,可溶性氟化物盐。可采用多种产氟离子的物质作为本发明组合物中的可溶性氟化物的来源。合适的产氟离子的物质的实例见于授予Briner等人的美国专利No.3,535,421、授予Parran,Jr.等人的美国专利No.4,885,155和授予Widder等人的美国专利No.3,678,154,这些专利以引用方式并入本文。代表性氟离子源包括但不限于氟化亚锡、氟化钠、氟化钾、单氟磷酸钠、氟硅酸钠、氟硅酸铵、胺氟化物、氟化铵及其组合。在某些实施方案中,氟离子源包括氟化亚锡、氟化钠和单氟磷酸钠及其混合物。在某些实施方案中,本公开的口腔护理组合物也可含有提供氟离子或氟的成分的来源,所述来源的量足以供应约25ppm至约25,000ppm的氟离子,通常为至少约500ppm,例如,约500ppm至约2000ppm,例如,约1000ppm至约1600ppm,例如,或约1450ppm。氟化物的适当含量将取决于特定应用。供一般消费者使用的牙膏可具有例如约1000ppm至约1500ppm,其中儿童牙膏略低。供专业应用的洁牙剂或涂布剂可具有例如多达约5,000或甚至约25,000ppm的氟化物。氟离子源可按以下水平添加到本公开的组合物中:在一个实施方案中约0.01重量%至约10重量%,或约0.03重量%至约5重量%,以及在另一个实施方案中约0.1重量%至约1重量%。用于提供适当水平的氟离子的氟化物盐的重量将基于盐中的抗衡离子的重量而明显地变化。
发泡剂
本公开的口腔护理组合物还可包含当刷动口腔时增加所产生的泡沫的量的试剂。增加泡沫量的试剂的说明性实例包括但不限于聚氧乙烯和某些聚合物,包括但不限于海藻酸盐聚合物。聚氧乙烯可增加由本公开的口腔护理载体组分所产生的泡沫的量和泡沫的浓密程度。聚氧乙烯也通常被称为聚乙二醇(“PEG”)或聚环氧乙烷。适合于本公开的聚氧乙烯将具有约200,000至约7,000,000的分子量。在一个实施方案中,分子量将为约600,000至约2,000,000,以及在另一个实施方案中约800,000至约1,000,000。是由UnionCarbide生产的高分子量聚氧乙烯的商标名。按本公开的口腔护理组合物的口腔护理载体组分的重量计,聚氧乙烯可以约1%至约90%,在一个实施方案中约5%至约50%,以及在另一个实施方案中约10%至约20%的量存在。口腔护理组合物中起泡剂的量为约0.01重量%至约0.9重量%、约0.05重量%至约0.5重量%以及在另一个实施方案中约0.1重量%至约0.2重量%。
防牙结石剂
口腔组合物可以包含至少一种防牙结石组合物,诸如在题为″AntibacterialAnti-plaque Anticalculus Oral Composition″的美国专利No.5,292,526中所列举的防牙结石组合物中的一种或多种,该专利以引用方式并入本文。在各种实施方案中,防牙结石组合物包含一种或多种多磷酸盐。防牙结石组合物可包含以有效防牙结石量存在于口腔组合物中的至少一种完全或部分中和的碱金属或铵三聚磷酸盐或六偏磷酸盐。防牙结石组合物也可包含在防牙结石量下有效的至少一种水溶性、线型、分子脱水多磷酸盐。防牙结石组合物也可包含钾盐和钠盐的混合物,所述钾盐和钠盐中的至少一种作为多磷酸盐防牙结石剂以有效防牙结石量存在。防牙结石组合物也可含有以钠盐和钾盐的混合物存在的有效防牙结石量的线型分子脱水多磷酸盐防牙结石剂。其他适用的防牙结石剂包括聚羧酸酯聚合物和聚乙烯基甲基醚/马来酸酐(PVME/MA)共聚物,诸如GANTREZ.RTM。
表面活性剂
适用于本公开的组合物可含有阴离子和/或非离子表面活性剂,例如:
i.高级脂肪酸单硫酸单甘油酯的水溶性盐,诸如氢化椰子油脂肪酸的单硫酸化单甘油酯的钠盐,诸如N-甲基N-椰油基牛磺酸钠、椰油酸单甘油酯硫酸钠,
ii高级烷基硫酸盐,诸如月桂基硫酸钠,
iii.高级烷基醚硫酸盐,例如,式CH3(CH2)mCH2(OCH2CH2)nOSO3X的高级烷基醚硫酸盐,其中m为6-16,例如10,n为1-6,例如2、3或4,并且X为Na或K,例如月桂基聚氧乙烯(2)醚硫酸钠(CH3(CH2)10CH2(OCH2CH2)2OSO3Na),
iv.高级烷基芳基磺酸盐,诸如月桂基苯磺酸钠(月桂基苯磺酸钠),
v.高级烷基磺基乙酸盐,如月桂基磺基乙酸钠(月桂基磺基乙酸钠)、1,2二羟基丙烷磺酸的高级脂肪酸酯、磺基月桂酸盐(sulfocolaurate)(N-2-乙基月桂酸钾磺基乙酰胺)和月桂基肌氨酸钠。
“高级烷基”意思是例如C6-30烷基。在特定实施方案中,阴离子表面活性剂选自月桂基硫酸钠和月桂基醚硫酸钠。阴离子表面活性剂可以有效的(例如,大于配方的0.01重量%),但不处于将刺激口腔组织的浓度下(例如,小于10%)的量存在,并且最佳浓度取决于特定配方和特定表面活性剂。在一个实施方案中,阴离子表面活性剂以约0.3重量%至约4.5重量%(例如,约1.5重量%)存在于牙膏中。
非离子表面活性剂包括非阴离子聚氧乙烯表面活性剂,诸如泊洛沙姆407、硬脂基聚氧乙烯30、聚山梨醇酯20和PEG-40蓖麻油;以及两性表面活性剂,诸如椰油酰胺丙基甜菜碱(tegobaine)和椰油酰胺丙基甜菜碱月桂基葡糖苷,氧化乙烯与各种含氢化合物的缩合产物,所述含氢化合物可与氧化乙烯反应并具有疏水性长链(例如,约12至20个碳原子的脂族链),所述缩合产物(“乙沙姆”)含有亲水性聚氧乙烯部分,诸如聚(氧化乙烯)与脂肪酸、脂肪醇、脂肪酰胺和其他脂肪部分的缩合产物,以及与氧化丙烯和聚氧化丙烯的缩合产物(例如,Pluronic.RTM.材料)。
本公开的组合物可任选地含有表面活性剂的混合物,例如,包含阴离子表面活性剂和可为阴离子、阳离子、两性离子或非离子的其他表面活性剂。通常,表面活性剂是在宽的pH范围内合理稳定的那些表面活性剂。表面活性剂更全面地例如在授予Agricola等人的美国专利No.3,959,458、授予Haefele的美国专利No.3,937,807和授予Gieske的美国专利No.4,051,234中进行了描述,这些专利以引用方式并入本文。在某些实施方案中,适用于本文中的阴离子表面活性剂包括在烷基中具有约10至约18个碳原子的烷基硫酸酯的水溶性盐以及具有约10至约18个碳原子的脂肪酸的磺化单甘油酯的水溶性盐。月桂基硫酸钠、月桂酰肌氨酸钠以及椰子基单甘油酯磺酸钠为这一类型的阴离子表面活性剂的实例。在一个实施方案中,组合物包含月桂基硫酸钠。
表面活性剂或相容表面活性剂的混合物可以按总组合物的重量计以约0.1%至约5.0%,在另一个实施方案中约0.3%至约3.0%,以及在另一个实施方案中约0.5%至约2.0%存在于本公开的组合物中。
调味剂
本公开的口腔护理组合物也可包含调味剂。用于本公开的实践中的调味剂包括但不限于精油以及各种调味醛、酯、醇以及类似物质。精油的实例包括留兰香、胡椒薄荷、冬青、黄樟、三叶草、鼠尾草、桉树、牛至属植物、肉桂、柠檬、酸橙、柚子和橙的油。诸如薄荷醇、香芹酮以及茴香脑等化学品也适用。某些实施方案采用薄荷油和绿薄荷油。调味剂可以按约0.1重量%至约5重量%和约0.5重量%至约1.5重量%的浓度掺入口腔组合物中。单个口腔护理组合物中调味剂的剂量为约0.001重量%至0.05重量%以及在另一个实施方案中约0.005重量%至约0.015重量%。
其他任选成分
除上述组分之外,本公开的实施方案还可以含有多种任选的洁齿剂成分,其中一些在下文描述。任选成分包括例如但不限于气泡剂、甜味剂和另外的着色剂。这些和其他任选的组分在授予Majeti的美国专利No.5,004,597、授予Agricola等人的美国专利No.3,959,458和授予Haefele的美国专利No.3,937,807中有进一步描述,所有这些专利均以引用方式并入本文。
在一个实施方案中,该薄片相对于其总重量具有小于1重量%的淀粉,诸如0.1%或更低、或0.01%或更低。术语“不含淀粉”在本文定义为表示不向成膜成分添加淀粉,并且所得的薄膜不含可测量的淀粉量。
本公开也包括用于暂时美白牙齿的方法,其包括将有效量的本公开的组合物施用于有需要的受试者的口腔。组合物的美白效果被视为暂时的,因为其美白效果将例如在施加之后的约两周内,在不做另外处理的情况下随着时间明显减弱。
通过以下非限制性实施例,进一步示出与本公开一致的实施方案。
实施例
实施例1-制备包令颜料的薄片
将表1所示列表的成分混合在一起以形成液体成膜组合物。通过成膜组合物,浇注包含蓝色颜料15的含颜料的薄膜。配方中的唯一成膜材料是HPMC聚合物,具体地讲以商标名Methocel E5由Dow Corning销售的HPMC聚合物。Methocel E5是一种低分子量HPMC,其在20℃和10s-1的剪切速率下具有4-6mPa.s的粘度(对于2%的溶液来说)。
表1
成分 | 重量% |
HPMC E5 | 55.2 |
蓝色颜料15 | 16.9 |
红30 | 3.4 |
丙二醇 | 20.7 |
Tween 80 | 3.8 |
在浇注后,将所得的薄膜研磨成包含颜料的小薄片。
实施例2-洁齿剂配方制备
将实施例1的小薄片掺入由表2中所列的成分制备的洁齿剂配方。
表2:配方组成
制备了表2的包含蓝色颜料HMPC薄膜(0.05%蓝色颜料)的洁齿剂基料组合物的三个单独的样品。样品1不含添加的FD&C蓝#1,并用作对照样品。FD&C蓝#1分别以0.05%和0.10%的量添加到样品2和3。
实施例3-美白测试
移除人的第三磨牙的牙根,并且将每颗牙齿从冠部到根部对分。使用热压印化合物将每一半牙齿安装在甲基丙烯酸酯树脂中,然后固定在刷盘中,使釉质侧面朝外。每个托盘安装四颗牙齿。将牙齿用1∶2(w/w)的二氧化硅牙膏浆液刷10分钟以移除任何外在表面污垢、用去离子水冲洗并用冷空气干燥。利用分光光度计(Spectroshade Micro,MHTtechnologies)记录基线CieLab测量值。
然后将如上准备的牙齿浸入唾液(每个托盘9mL)并在37℃和温和搅拌下老化15分钟。然后将得自以上样品1至3中每一个的测试牙膏(6g)添加到已含9ml唾液的单独的托盘。将牙齿用每种样品牙膏刷2分钟,用100mL去离子水冲洗,用冷空气干燥,并记录CieLab测量值。
在刷动后,将牙齿再次在唾液中老化。在唾液中老化10分钟和30分钟后记录CieLab测量值。冲洗牙齿,用冷空气干燥,然后在浸泡循环中的每个时间点记录CieLab测量值。报告Δb*,其为在CieLab色空间中在黄-蓝轴上的变化。这是可借以量化蓝色试剂的沉积的量度。下表3中报告的Δb*是移除表面污垢后牙齿的b*值与用得自以上样品1、2和3中每一者的产品刷动后的b*值之差。还报告了美白度指数(WIO)的变化来证实蓝色试剂的沉积引起牙齿美白度的增加。
表3
向具有由HMPC薄膜提供的0.05%蓝色颜料15的口腔护理组合物添加FD&C蓝#1增加了配方的整体美白效力,如从表3中的数据所见。这种美白增强是令人惊讶的,因为已知单独的蓝色染料在具有相对高水含量的配方(诸如像上述配方一样含有约20%或更多的水)中在不使用诸如PVM/MA的聚合物的情况下并不能良好地粘附到牙齿。
因此,上述实施例证实了含有FD&C蓝#1染料和HPMC聚合物薄膜中的颜料15的口腔护理组合物(其中该组合物不含PVM/MA共聚物)与包含单独的蓝色颜料的相同口腔组合物相比提供了优异的蓝色化合物向牙齿表面的沉积,并因而改善了美白。
Claims (16)
1.一种通过将包括以下的成分合并而制备的牙齿美白口腔护理组合物:
(i)水溶性美白薄膜的薄片,其包含:
(a)含羟烷基纤维素的成膜聚合物,其中所述羟烷基纤维素是羟丙基甲基纤维素聚合物;其中所述羟烷基纤维素具有低粘度,其中所述低粘度是指在20℃下使用乌式管粘度计以所述成膜聚合物的2重量%水溶液所测定的1毫帕秒(mPa.s)至1000毫帕秒的粘度;和
(b)在CIELAB体系中具有在200度至320度范围内的色调角的至少一种颜料,其中所述颜料选自颜料蓝#15、红30及其混合物;
其中所述薄片通过冲压、切割或研磨而从所述成膜聚合物制备,使得超过90%的颗粒通过50目过滤器或者使得粒度在30目至100目之间;
(ii)在CIELAB体系中具有在200度至320度范围内的色调角的至少一种染料,其中所述染料为FD&C蓝#1;以及
(iii)口腔可接受的载体媒介;并且
其中所述口腔护理组合物包含相对于所述组合物的总重量而言量在20重量%至35重量%范围内的水。
2.根据权利要求1所述的口腔护理组合物,其中所述颜料为颜料蓝#15和红30的混合物。
3.根据权利要求1所述的口腔护理组合物,其中所述口腔护理组合物包含相对于所述组合物的总重量而言低于0.0001重量%的生物粘合剂聚合物,其中所述生物粘合剂聚合物不同于羟烷基纤维素。
4.根据权利要求1所述的口腔护理组合物,其中所述口腔护理组合物包含相对于所述组合物的总重量而言低于0.0001重量%的甲基乙烯基醚/马来酸酐共聚物。
5.根据权利要求1所述的口腔护理组合物,其中所述口腔可接受的载体媒介包含湿润剂。
6.根据权利要求1所述的口腔护理组合物,其中所述口腔组合物还包含选自防龋剂和防牙结石剂的至少一种活性剂。
7.根据权利要求1所述的口腔护理组合物,其中所述口腔护理组合物为牙膏或牙凝胶。
8.根据权利要求1所述的口腔护理组合物,其中所述薄片的粒度使得超过90%的所述薄片能够通过50目过滤器。
9.根据权利要求1所述的口腔护理组合物,其中按所述口腔护理组合物的重量计,所述薄片的量为0.01至5%。
10.根据权利要求1所述的口腔护理组合物,其中所述薄片不含淀粉。
11.根据权利要求1所述的口腔护理组合物,其中所述薄片还包含湿润剂或表面活性剂中的至少一种。
12.根据权利要求1所述的口腔护理组合物,其中所述口腔可接受的载体媒介包含选自载体聚合物、湿润剂、水、磨料和增稠剂的至少一种成分。
13.根据权利要求1所述的口腔护理组合物,还包含有效量的另一药剂,所述药剂选自氟化物、呈游离或口腔可接受的盐形式的精氨酸、除镓盐和碱性氨基酸聚合物之外的抗菌剂、抗炎剂、美白剂和其两种或更多种的组合。
14.根据权利要求1所述的口腔护理组合物,其中口腔护理组合物为洁齿剂。
15.根据权利要求1所述的口腔护理组合物,其中所述口腔护理组合物为包含水、磨料、表面活性剂、发泡剂、维生素、聚合物、酶、湿润剂、增稠剂、抗微生物剂、防腐剂、调味剂、着色剂中的一种或多种和/或其两种或更多种的组合的牙膏。
16.一种用于暂时美白牙齿的方法,包括将有效量的根据权利要求1所述的口腔护理组合物施用于受试者的口腔。
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- 2014-12-19 BR BR112017012109-3A patent/BR112017012109B1/pt not_active IP Right Cessation
- 2014-12-19 MX MX2017007696A patent/MX367955B/es active IP Right Grant
- 2014-12-19 RU RU2017121319A patent/RU2677886C2/ru active
- 2014-12-19 US US15/533,466 patent/US10512596B2/en active Active
- 2014-12-19 CA CA2971166A patent/CA2971166C/en active Active
- 2014-12-19 EP EP14825553.2A patent/EP3223785B1/en active Active
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- 2014-12-19 AU AU2014413970A patent/AU2014413970B2/en not_active Ceased
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2017
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RU2677886C2 (ru) | 2019-01-22 |
MX367955B (es) | 2019-09-12 |
EP3223785A1 (en) | 2017-10-04 |
CA2971166C (en) | 2021-11-09 |
US20170326039A1 (en) | 2017-11-16 |
CA2971166A1 (en) | 2016-06-23 |
AU2014413970A1 (en) | 2017-06-08 |
RU2017121319A3 (zh) | 2019-01-21 |
EP3223785B1 (en) | 2021-07-21 |
RU2017121319A (ru) | 2019-01-21 |
IL252344A0 (en) | 2017-07-31 |
CN106999393A (zh) | 2017-08-01 |
BR112017012109A2 (pt) | 2018-07-03 |
MX2017007696A (es) | 2017-10-27 |
US10512596B2 (en) | 2019-12-24 |
AU2014413970B2 (en) | 2018-07-05 |
WO2016099544A1 (en) | 2016-06-23 |
BR112017012109B1 (pt) | 2020-08-25 |
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