CN1072843A - 凝胶型化妆品组合物 - Google Patents
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Abstract
低pH水凝胶形式的护肤组合物,此组合物提供
了改善的皮肤感觉和残留特性并具有优越的增湿、润
肤、擦入和吸收特性。
Description
本发明涉及化妆品组合物,尤其是涉及水凝胶形式的稳定低pH化妆品组合物,该组合物提供了改善的皮肤感觉和残留特性并且具有改善的润湿、润肤、擦入和吸收特性。
多年以来,为达到保持皮肤光滑柔软状态的目标曾采用过各种各样的试剂来处理人的皮肤。暴露于低湿度状态或洗涤溶液相当一段时期,皮肤就趋于干燥。皮肤由几层覆盖和保护构成其结构骨架的角蛋白和胶原纤维蛋白的细胞组成,这些层的最外层,称之为角质层,已知是由80A厚的层包围的250A蛋白束所组成。阴离子表面活性剂和有机溶剂典型地穿透角质层膜,并且通过脱脂化作用(即是从角质层去除脂类)破坏其完整。皮肤表面构形的破坏导致粗糙的感觉并可能最终让表面活性剂或溶剂接触角蛋白,产生刺激感。
业已知道,保持穿过角质层的适当的水分梯度对其功能是重要的。这类水的很大部分来自体内,水有时被看作是角质层的增塑剂。如果湿度太低,象在寒冷的气候下,没有足够的水保留在角质层的外层以适当地增塑组织;并且皮肤开始起皮并且变得瘙痒。当没有充足的水分穿过角质层时,皮肤的透过性也在某种程度上降低。加一方面,皮肤的外层上的水太多会引起角质层最终吸收其自重三至五倍的结合水,这样便使皮肤膨胀和起皱,导至皮肤对水和其它极性分子的透过性增加约二至三倍。
常规的化妆品乳膏和洗剂组合物[例如,在Sagarin著的“化妆品科学和技术”,第2版,第1卷,Wiley Interscience出版(1972)和“化学技术百科全书”,第三版,第7卷中所描述的],业已知道提供了不同程度的润肤、防护和保水(湿润)效用。然而,它们也可能在皮肤感觉方面带来严重的副作用(即它们通常使皮肤感觉很滑腻),还可能具有不良的擦入、吸收和残留特性。其它的化妆品组合物公开于例如,在1989年6月16日出版的Georgalas等人的美国专利4,837,019号中和1989年9月5日出版的Deckner等人的美国专利4,863,725号中,这两篇专利引入本文作为参考。再则,人们希望从低pH载体释放许多化妆品成分和药物成分,然而,适合的低pH载体至今还未开发出来。还有,许多药物和化妆品活性成分需要低的pH环境以期有效和/或稳定。目前的低pH赋形剂含有天然树脂和无机粘土和粉料且并未令人满意。这些***表现出稳定性差和过分干燥皮肤且为化妆品所不期望的,即不美观。
众所周知用聚丙烯酸,例如carbomers增稠化妆品组合物,然而,这些增稠剂不能在低pH使用。因此迫切需要具有一种相对高的粘度能够用来释放药物和化妆品活性物的化妆优美和稳定低pH的化妆品组合物。
申请人已发现,在低pH化妆品组合物中使用特定的具高分子量的聚丙烯酰胺提供了优越的化妆效用,并且为低pH体系提供了改进的稳定性。再则,高含量的可能需要溶解活性物的溶剂象乙醇和其它水溶性成分可以包括在此组合物中。
因此,本发明提供了低pH凝胶型化妆品组合物,它是某些低pH化妆品成分和药物活性物的优越载体并且还具有高溶剂耐受性。
本发明还提供了稳定低pH凝胶型化妆品组合物,该组合物在吸收、残留和皮肤感觉特性上提供改善且不会损害短期或长期的润湿效果或润肤作用。
因此,本发明的一个目的是提供改善的化妆品组合物,它是某些低pH化妆品成分和药物活性物的优越载体并且降低了粘着性以及为使用者提供光滑的皮肤感觉。
以下的公开将使本发明的这些和其它目的变得明朗。
因此,本发明提供了一种水凝胶形式的护肤组合物,该组合物含有:约0.05%至约20%的分子量为约1,000,000至约30,000,000的非离子聚丙烯酰胺,其中所述的组合物pH低于大约4。
在此所用的所有的百分数和比率均为重量比,并且是在25℃测量的,除非另有说明。
本发明的低pH组合物是由非离子聚合物和pH值调至低于大约4的水(优选的是低于大约3.5,最优选的是低于约3.0)组合而成。除非另有说明,所有含量和比率都是以整个组合物的重量计。这些组合物还具有高溶剂耐受性,即高含量的溶剂象乙醇和其它水溶性组分(它们可能是溶解活性物所必需的)可以包括在该组合物中。
非离子聚丙烯酰胺对本发明有用的非离子聚合物为聚丙烯酰胺和被取代的支链或直链聚丙烯酰胺。这些聚合物为非离子水可分散聚合物,它们可以由包括未被取代或者被一个或二个烷基(优选C1-C5)取代的丙烯酰胺和甲基丙烯酰胺的各种单体组成。优选的为丙烯酰胺和甲基丙烯酰胺,其中酰胺氮未被取代或者被一个或二个C1-C5烷基(优选的为:甲基、乙基或丙基)取代,例如:丙烯酰胺、甲基丙烯酰胺、N-甲基丙烯酰胺、N-甲基甲基丙烯酰胺、N、N-二甲基甲基丙烯酰胺、N-异丙基丙烯酰胺、N-异丙基甲基丙烯酰胺和N、N-二甲基丙烯酰胺。这些单体一般性地公开于1990年10月16日出版的Bolich,Jr.等人的美国专利4,963,348号中,该专利全部引入本文作为参考。这些共聚物可以任意地使用常规中***联剂(象二链烯基化合物)构成。对于阳离子共聚物使用这类交联剂已经公开于1986年12月9日出版的Glover等人的美国专利4,628,078号中和1986年7月8日出版的Flesher等人的美国专利4,599,379号中,这两篇专利均引入本文作为参考。这些非离子共聚物的分子量大于约1,000,000。优选的为大于约1,500,000,并且范围上限达到约3,000,000。优选的是这些非离子聚丙烯酰胺在含有助于促进聚丙烯酰胺的水可分散性的高HLB表面活性剂(HLB从约7至约10)的、与水不可混溶的溶剂(如矿物油等)中预分散。最优选用于本发明的是CTFA牌的非离子聚合物:聚丙烯酰胺和异链烷烃和Laureth-7,可以从Seppic Corporation以Sepigel商标购得。
这些非离子聚丙烯酰胺的含量是约0.05%至约20%,优选的为约0.5%至10%,最优选的为约1%至约10%。
这些组合物优选的是与各种选择成分组合。最优选的是,这些凝胶用作药物活性物(最优选的是抗痤疮活性物)的载体。本发明组合物对于那些酸性或需要低pH以最佳释放或稳定的活性成分是最为有用的。
药物活性物本发明中有用的药物活性物包括任何适合于产生任何所期待的局部或***效果的局部给药的化学物质或化合物。这些活性物的含量约为0.1%至20%。这类药剂包括,但不限于:抗痤疮药、非甾类化合物消炎药、甾类化合物消炎药、无日光晒黑剂、防晒剂、伤口愈合剂、皮肤增白剂或增亮剂、抗组胺药、镇咳药、止痒药、抗类胆碱药、止吐药、抗晕眩药、厌食药、中枢刺激药、抗心律不齐药、B-肾上腺素能阻滞药、强心药、抗高血压药、利尿药、血管舒张药、血管收缩药、抗溃疡药、***、抗抑郁药、安定和镇静药、抗精神病药、抗微生物药、抗肿瘤药、抗疟药、肌肉松弛药、抗痉挛药、抗腹泻药和活骨药及其混合物。
在本发明中有用的还有无日光晒黑剂,包括:二羟基丙酮、甘油醛、吲哚和它们的衍生物等等。这些无日光晒黑剂还可以与常用的防晒剂组合使用,这些防晒剂是例如在Segarin等人著的“化妆品科学和技术”(第8章,从189页开始)中公开的那些,该文献引入本文作为参考,也可以与伤口愈合剂象肽衍生物、酵母、泛酰醇、Iamin和激动素组合使用。
其它的有用的皮肤活性物包括皮肤增白(或增亮)剂,包括但不限于氢醌、抗坏血酸、曲酸和焦亚硫酸钠。
最优选的药物活性成分是抗痤疮药。本发明所使用的优选的抗痤疮药包括角质层分离剂象水杨酸、硫黄、乳酸、乙醇酸、丙酮酸、尿素、间苯二酚、和N-乙酰半胱氨酸;视网膜样物质象视黄酸和它的衍生物(例如,顺式和反式);抗生素和抗微生物药象过氧苯甲酰、羟甲辛吡酮、红霉素、四环素、二氯苯氧氯酚、壬二酸及其衍生物、苯氧乙醇和苯氧丙醇、乙酸乙酯、氯洁霉素和甲基氯环素,sebostate象核黄素类物质,α和β羟酸,和胆汁盐象硫酸鲨胆甾醇及其衍生物、脱氧胆酸盐、和胆酸盐。
维生素各种维生素也可以包括在本发明组合物中。例如,抗坏血酸、panthorthenic acid、维生素E、生育酚等等。
水溶性湿润剂这些组合物还可以含有一种或多种湿润剂/增湿剂。可以采用各种湿润剂/增湿剂,其含量可以从约1%至约30%,更优选的为约2%至约8%最优选的为约3%至约5%。这些原料包括多元醇象山梨醇、甘油、己三醇、丙二醇、己二醇等等;聚乙二醇、糖和淀粉、糖和淀粉衍生物(例如,烷氧基化葡萄糖)D-泛酰醇,透明质酸,乳酰胺单乙醇胺,乙酰胺单乙醇胺,2-吡咯烷酮-5-羧酸,和它们的混合物。
本发明组合物中采用的优选的湿润剂/增湿剂为C3-C6二醇和三醇。特别优选的是三醇,甘油。本发明组合物还可以含有可药用的、改善组合物物理和/或治疗效果的任意成分。这类任意成分可以包括,例如,附加溶剂、乳化剂、胶凝剂、芳香剂、防腐剂和稳定剂。其它有用的湿润剂包括糖苷(例如,GlucamE10和E20,可从Ameychol Corporation购得)、乳酰胺单乙醇胺和乙酰胺单乙醇胺。
这些水溶性湿润剂的混合物也可以使用。
在本发明中,水溶性湿润剂含量占组合物重量的约0.5%至约20%,优选的是约1%至约10%,更优选的是约4%至约8%。
任意的亲水胶凝剂本发明低pH凝胶组合物还可以含有一种附加的亲水胶凝剂(它在低pH是稳定的),其含量优选的是从约0.05%至约1%,更优选的是从约0.1至约1%。此胶凝剂优选的为粘度在至少约4000厘泊(1%水溶液,20℃,Brookfield RVT),至优选的为至少约10,000厘泊,最优选的为至少50,000。
适合的亲水胶凝剂可以概括地描述为水溶性或胶态水溶性聚合物,包括纤维醚(例如,羟乙基纤维素、甲基纤维素)、羟丙基瓜耳树胶和黄原胶。有用的还有粘土如水辉石(Veegum)和膨润土。
润肤剂 本发明的组合物还可以包括至少一种润肤剂(在低pH稳定)。优选的润肤剂为挥发性硅酮油、非挥发性润肤剂及它们的混合物。本发明组合物更优选的是包含至少一种具液态润肤剂功能的挥发性硅酮油,或者特别是挥发性硅酮油和非挥发性润肤剂的混合物。在此采用的术语“挥发性”是指那些在室温具可测蒸气压的物质。
对本发明组合物有用的挥发性硅酮油优选的是含有约3至约9个硅原子的环状或直链聚二甲基硅氧烷,优选的是约4至约5个硅原子。下列结构式说明了在本发明组合物中适用的环状挥发性聚二甲基硅氧烷:
其中n等于约3至约7。直链聚二甲基硅氧烷每分子含有约3至约9个硅原子,它具有下列通式:
其中n等于约1至7。直链挥发性硅酮物质的粘度通常在25℃时为约0.5厘沲,而环状物质的粘度典型地小于约10厘沲。各种挥发性硅酮油的描述可见于Todd等人著的“化妆品用挥发性硅酮流体”一文(Cosmetics Toiletries,91,p27-32(1976)),其中公开内容全部引入本文作为参考。
本发明有用的优选挥发性硅酮油的实例包括:Dow Corning344、Dow Corning345和Dow Corning200(由Dow CorningCorp.生产),Silicone7207和Silicone7158(由Union Carbide Corp.生产),SF1202(由General Electric生产),和SWS-03314(由SWS Silicones,Inc.生产)。
本发明组合物还优选含有一种或多种非挥发性润肤剂。这类物质包括烃(例如,Permethyls)、丙氧基化乙醇、非挥发性硅酮油及其混合物。本发明这些有用的润肤剂描述于“化妆品科学和技术”第1卷27-104页(M.Balsam和E.Sagarin Ed.;1972)和1980年5月13日出版的Shelton的美国专利4,202,879号中(两篇文献均引入本文作为参考)。
适于作为润肤材料的非挥发性硅酮油包括聚烷基硅氧烷、聚烷基芳基硅氧烷、和聚醚硅氧烷共聚物。适于本发明的非挥发性聚烷基硅氧烷包括,例如,聚二甲基硅氧烷,其粘度在25℃时为约5至约100,000厘沲。适用于本发明组合物的优选的非挥发性润肤剂为在25℃时粘度为约10至约400厘沲的聚二甲基硅氧烷。这类聚烷基硅氧烷包括Vicasil系列(由General Electric Company出售)和Dow Corning200系列(由Dow Corning Corporation出售)。聚烷基芳基硅氧烷包括在25℃时粘度为约15至约65厘沲的聚甲基苯基硅氧烷。它们能购买到,例如,SF1075甲基苯基流体(由General Electric Company出售)和566化妆品级流体(由Dow Corning Corporation出售)。有用的聚醚硅氧烷共聚物包括,例如,一种在25℃粘度为约1200至1500厘沲的聚氧亚烷醚共聚物。这种流体可以以SF-1066有机硅酮表面活性剂的商品购买到(由General Electric Company出售)。聚硅氧烷乙二醇醚共聚物为本发明组合物采用的优选共聚物。
典型的润肤剂占本发明组合物总重量的约2%至约10%,最优选的为约2%至约6%。
一些附加的水溶性材料也可以加到本发明的组合物中。这类材料包括其他的湿润剂如山梨醇、丙二醇、甲氧基化葡萄糖和己三醇;角质层分离剂如水杨酸;蛋白质和多肽及其衍生物,水溶或可溶性防腐剂如Germall115、羟基苯甲酸的甲酯、乙酯、丙酯和丁酯、EDTA、Euxyl(RTM)K400,Bromopol(2-溴-2-硝基丙-1,3-二醇)、苯氧丙醇、DMDM乙内酰脲/氨基甲酸3-碘-2-丙炔基丁酯(以Glydant
和Glydant
Plus销售);抗菌素如Irgasan(RTM)和苯氧乙醇(优选的含量为0.5%至约5%);可溶性或胶态可溶性增湿剂如透明质酸、聚氨基葡糖和着色剂;香料和香料增溶剂等。还含有占本发明组合物重量约50%至约99.3%的水,优选为约80%至约95%。
其它任意组分 各种附加的成分可以被加入本发明的乳化组合物。这些附加成分包括有助于制剂的成膜性和直接性的各种聚合物、保持组合物抗菌力完好的防腐剂、抗氧化剂和为了达到麻醉目的的试剂如芳香剂、颜料和着色剂。
本发明的组合物为水凝胶形式,优选配制成粘度至少为约4,000、优选约4,00至约300,000厘泊、更优选约为20,000至约200,000厘泊特别是约80,000至约150,000厘泊(20℃,纯品,Brook field RVT)的产品。优选的组合物是可见的半透明物。组合物还大体上不含油,即,油含量小于1%,优选的是在10℃的水凝胶基质中不可溶的或非胶态可溶的物质少于约0.1%。“胶态可溶”在此处是指在通常的胶态大小范围的粒子,典型的是1至1000nm,特别是1至500nm。在最优选的实施例中,组合物大体上不含有在20℃的蒸馏水中不可溶的或非胶态可溶的物质。这类物质包括许多常规的润肤物质如烃油和蜡、脂肪醇、一些脂肪醇醚和从半毛脂中提取的甾醇、蜂蜡衍生物、植物蜡、甾醇和酰胺。然而,该组合物可以含有例如为视觉效果目的添加的低含量不可溶成分,例如,金黄色云母。
这些组合物可以包括附加的助溶剂如乙醇、异丙醇、丁二醇、己二醇、聚乙二醇、聚丙二醇。
本发明的组合物不需要附加的惯常添加入化妆品乳膏和洗剂组合物以便乳化水/可溶性油相的表面活性剂物质。
下列实施例进一步描述和说明在本发明范围内的实施方案。给出实施例只用于说明而非限制本发明,因此在不偏离本发明的精神和范围的前提下可以对其进行多种变化。
各成分依照化学或CTFA命名定义。
实施例
实施例1
采用常规的混合技术通过将下列成分组合制成抗痤疮组合物。
成分 (%重量/重量)
纯化水 54.0
Alcohol SD40 40.0
聚丙烯酰胺和C13-14
异链烷烃和Laureth-714.0
水杨酸 2.0
1 以Sepigel商标可以从Seppic Corporation购得。
将水加到大小适合的容器中。以中等速度(300rpm)混合,同时将polyquaternium-32和矿物油加到水中。单独将乙醇置入另一容器并加上盖。采用带有三个螺旋浆的Lightnin混合器,将水杨酸加入乙醇中并在低速度(100rpm)混合直至水杨酸溶解。将此乙醇缓慢地加入水相形成凝胶。所产生的凝胶以中等速度混合直至均匀。
该组合物显示出改善的皮肤感觉和残留特性并具有优越的增湿、润肤、擦入和吸收特性。
实施例2
无日光晒黑组合物采用上述实施例1所描述的常规混合技术组合下列成分制成。
成分 (%重量/重量)
纯化水 91.5
聚丙烯酰胺和C13-14
异链烷烃和Laureth-7 3.0
二羟基丙酮 3.0
苯甲醇 0.5
实施例3
抗痤疮组合物制备如实施例1,由下列成分组合而成。
成分 (%重量/重量)
纯化水 88.0
聚丙烯酰胺和C13-14
异链烷烃和Laureth-7 2.0
过氧苯甲酰 10.0
实施例4
局部止痛组合物由下列成分组合而成。
成分 (%重量/重量)
纯化水 52.395
Alcohol SD 40 40.000
聚丙烯酰胺和C13-14
异链烷烃和Laureth-7 4.000
布洛芬 5.000
甘油 1.000
Aloe Vera Gel 0.500
薄荷醇 0.100
EDTA二钠 0.005
将乙醇加到大小适当的容器中。采用带3个螺旋浆的Lightnin混合器,加布洛芬至乙醇中并以低速度(100rpm)混合直至布洛芬溶解。将薄荷醇加至乙醇中并混合直至溶解。单独将水加到一个大小适当的容器中。将Aloe vera gel和EDTA二钠加至水中并以低速度(100rpm)混合直至完全溶解。然后将水相加至乙醇相中并混合直至澄清。加甘油并混合直至澄清。以中等速度(300rpm)混合的同时,将聚丙烯酰胺和C13-14异链烷烃和Laureth-7加入形成凝胶。产生的凝胶以中等速度混合直至均匀。
实施例5
如实施例1所述将下列组分组合,用10%柠檬酸溶液调节pH至低于约4.0制备抗痤疮组合物。
成分 (%重量/重量)
纯化水 87.5
聚丙烯酰胺和C13-14
异链烷烃和Laureth-7 2.0
尿素 10.0
苯甲醇 0.5
实施例6
如实施例1所述由下列组分组合制备增湿组合物。
成分 (%重量/重量)
纯化水 93.5
聚丙烯酰胺和C13-14
异链烷烃和Laureth-7 2.0
甘油 3.0
苯甲醇 0.5
2-吡咯烷酮 5-羧酸 1.0
Claims (14)
1、一种水凝胶形式的护肤组合物,其特征在于它包含:约0.05%至约20%的分子量为约1,000,000至约30,000,000的非离子聚丙烯酰胺,其中所述组合物的pH低于大约4。
2、根据权利要求1的组合物,其中聚丙烯酰胺的特征在于它包含选自未被取代或被至少一个有约1至5个碳原子的烷基取代的丙烯酰胺和甲基丙烯酰胺单体。
3、根据权利要求2的组合物,其中聚丙烯酰胺的特征在于它包含选自丙烯酰胺、甲基丙烯酰胺、N-甲基丙烯酰胺、N-甲基甲基丙烯酰胺、N,N-二甲基甲基丙烯酰胺、N-异丙基丙烯酰胺、N-异丙基甲基丙烯酰胺和N,N-二甲基丙烯酰胺。
4、根据权利要求3的组合物,其中所述组合物的pH低于大约3.5。
5、根据权利要求4的组合物,其中所述组合物的进一步特征在于它含有湿润剂。
6、根据权利要求5的组合物,其中所述湿润剂选自多元醇、甘油、己三醇、丙二醇、己二醇、聚乙二醇、2-吡咯烷酮-5-羧酸、D-泛酰醇、透明质酸、乳酰胺单乙醇胺、乙酰胺单乙醇胺及其混合物。
7、根据权利要求6的组合物,其中所述乳液进一步的特征在于:它包含约0.1%至约20%的药物活性物。
8、根据权利要求7的组合物,其中所述的药物活性选自抗痤疮药、非甾类化合物消炎药、甾类化合物消炎药、无日光晒黑剂、防晒剂、伤口愈合剂、皮肤增白或增亮剂、抗组胺药、镇咳药、止痒药、抗类胆碱药、止吐药和抗晕眩药、厌食药、中枢刺激药、抗心律不齐药、β-肾上腺素能阻滞药、强心药、抗高血压药、利尿药、血管舒张药、血管收缩药、抗溃疡药、***、抗抑郁药、安定药和镇静药、精神抑郁药、抗菌药、抗肿瘤药、抗疟药、肌肉松弛药、抗痉挛药、抗腹泻药、活骨药及其混合物。
9、根据权利要求8的组合物,其中所述组合物进一步的特征在于它包含润肤剂。
10、根据权利要求9的组合物,其中所述润肤剂为选自聚烷基硅氧烷,聚烷基芳基硅氧烷、和聚醚硅氧烷共聚物的非挥发性硅酮油。
11、根据权利要求10的组合物,其中所述药物活性物是抗痤疮活性物:它选自水杨酸、硫黄、间苯二酚、N-乙酰半胱氨酸、羟甲辛吡酮、视黄酸及其衍生物、过氧苯甲酰、红霉素、四环素、壬二酸及其衍生物、苯氧乙醇和苯氧丙醇、乙酸乙酯、氯洁霉素、甲基氯环素、核黄素类物质乳酸、乙醇酸、丙酮酸、烟酸、尿素、硫酸鲨胆甾醇及其衍生物、脱氧胆酸盐和胆酸盐及其混合物。
12、根据权利要求11的组合物,其中所述药物活性物为抗痤疮活性物,它选自水杨酸、硫黄、间苯二酚、羟甲辛吡酮、视黄酸及其衍生物、过氧苯甲酰、红霉素、四环素及它们的混合物。
13、权利要求7的组合物,其中所述药物活性物为无日光晒黑剂,它选自二羟基丙酮、吲哚衍生物及其混合物。
14、权利要求13的组合物,它进一步的特征在于包含防晒活性物。
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- 1992-10-13 JP JP50777093A patent/JP3555762B2/ja not_active Expired - Lifetime
- 1992-10-13 WO PCT/US1992/008743 patent/WO1993007856A1/en not_active Application Discontinuation
- 1992-10-13 AT AT92922437T patent/ATE133560T1/de not_active IP Right Cessation
- 1992-10-13 BR BR9206630A patent/BR9206630A/pt not_active Application Discontinuation
- 1992-10-13 DK DK92922437.6T patent/DK0608353T3/da active
- 1992-10-13 CZ CS94904A patent/CZ90494A3/cs unknown
- 1992-10-13 DE DE69208098T patent/DE69208098T2/de not_active Expired - Lifetime
- 1992-10-13 AU AU28000/92A patent/AU675210B2/en not_active Ceased
- 1992-10-13 SK SK439-94A patent/SK43994A3/sk unknown
- 1992-10-13 CA CA002119636A patent/CA2119636C/en not_active Expired - Fee Related
- 1992-10-13 KR KR1019940701238A patent/KR100244554B1/ko not_active IP Right Cessation
- 1992-10-13 HU HU9401105A patent/HUT66957A/hu unknown
- 1992-10-13 ES ES92922437T patent/ES2083197T3/es not_active Expired - Lifetime
- 1992-10-15 MX MX9205905A patent/MX9205905A/es unknown
- 1992-10-15 PT PT100962A patent/PT100962B/pt not_active IP Right Cessation
- 1992-10-15 NZ NZ244744A patent/NZ244744A/en unknown
- 1992-10-16 TR TR92/1008A patent/TR26721A/xx unknown
- 1992-10-16 CN CN92113394A patent/CN1050283C/zh not_active Expired - Lifetime
-
1994
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- 1994-04-15 FI FI941769A patent/FI941769A0/fi not_active Application Discontinuation
- 1994-05-25 US US08/249,093 patent/US5707635A/en not_active Expired - Lifetime
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1996
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1998
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Cited By (14)
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US8241649B2 (en) | 2001-12-21 | 2012-08-14 | Galderma Research & Development | Dermatological/cosmetic gels comprising at least one retinoid and/or retinoid salt and benzoyl peroxide |
CN1329025C (zh) * | 2001-12-21 | 2007-08-01 | 盖尔德马研究及发展公司 | 包含至少一种类维生素a和过氧化苯甲酰的凝胶 |
US9814690B2 (en) | 2001-12-21 | 2017-11-14 | Galderma Research & Development | Gel composition for treatment of common acne comprising a combination of benzoyl peroxide and adapalene and/or adapalene salt |
US7820186B2 (en) | 2001-12-21 | 2010-10-26 | Galderma Research & Development | Gel composition for once-daily treatment of common acne comprising a combination of benzoyl peroxide and adapalene and/or adapalene salt |
US7964202B2 (en) | 2001-12-21 | 2011-06-21 | Galderma Research & Development, S.N.C. | Method for treatment of common acne |
US8105618B2 (en) | 2001-12-21 | 2012-01-31 | Galderma Research & Development | Dermatological/cosmetic gels comprising at least one retinoid and/or retinoid salt and benzoyl peroxide |
US8936800B2 (en) | 2001-12-21 | 2015-01-20 | Galderma Research & Development | Gel composition for treatment of common acne comprising a combination of benzoyl peroxide and adapalene and/or adapalene salt |
CN100446773C (zh) * | 2006-04-29 | 2008-12-31 | 王菊荣 | 复方痤疮微乳膏及制备方法 |
CN100463930C (zh) * | 2006-12-21 | 2009-02-25 | 天津大学 | 可再分散pH敏感型阳离子聚合物水凝胶亚微米粒及制备方法 |
US10925814B2 (en) | 2006-12-21 | 2021-02-23 | Galderma Research & Development | Cream gels comprising at least one retinoid and benzoyl peroxide |
CN104780902A (zh) * | 2012-10-29 | 2015-07-15 | 日本乐敦制药株式会社 | 外用组合物 |
CN108467464A (zh) * | 2018-04-02 | 2018-08-31 | 常熟理工学院 | 含壬二酸可见光固化水凝胶及其制备方法 |
CN108553411A (zh) * | 2018-07-25 | 2018-09-21 | 成都卓阳生物科技有限公司 | 壬二酸凝胶剂及其制备方法和应用 |
CN108553411B (zh) * | 2018-07-25 | 2020-05-12 | 成都卓阳生物科技有限公司 | 壬二酸凝胶剂及其制备方法和应用 |
Also Published As
Publication number | Publication date |
---|---|
PT100962B (pt) | 1999-07-30 |
HU9401105D0 (en) | 1994-07-28 |
SK43994A3 (en) | 1995-01-12 |
BR9206630A (pt) | 1995-04-25 |
JP3555762B2 (ja) | 2004-08-18 |
CN1050283C (zh) | 2000-03-15 |
MA22677A1 (fr) | 1993-07-01 |
CA2119636A1 (en) | 1993-04-29 |
US5707635A (en) | 1998-01-13 |
HK1007504A1 (en) | 1999-04-16 |
DE69208098T2 (de) | 1996-08-08 |
WO1993007856A1 (en) | 1993-04-29 |
KR100244554B1 (ko) | 2000-04-01 |
ES2083197T3 (es) | 1996-04-01 |
PT100962A (pt) | 1993-11-30 |
NZ244744A (en) | 1995-07-26 |
EP0608353A1 (en) | 1994-08-03 |
MX9205905A (es) | 1993-06-01 |
JPH07500593A (ja) | 1995-01-19 |
TR26721A (tr) | 1995-05-15 |
DE69208098D1 (de) | 1996-03-14 |
GR3018853T3 (en) | 1996-05-31 |
AU2800092A (en) | 1993-05-21 |
FI941769A (fi) | 1994-04-15 |
FI941769A0 (fi) | 1994-04-15 |
DK0608353T3 (da) | 1996-07-01 |
CA2119636C (en) | 1998-06-23 |
ATE133560T1 (de) | 1996-02-15 |
CZ90494A3 (en) | 1994-07-13 |
NO941318D0 (no) | 1994-04-13 |
EP0608353B1 (en) | 1996-01-31 |
HUT66957A (en) | 1995-01-30 |
NO941318L (no) | 1994-06-15 |
AU675210B2 (en) | 1997-01-30 |
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