CN1265923A - 基于甘油脂肪酸酯的毫微乳液及其应用 - Google Patents
基于甘油脂肪酸酯的毫微乳液及其应用 Download PDFInfo
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- CN1265923A CN1265923A CN99126428A CN99126428A CN1265923A CN 1265923 A CN1265923 A CN 1265923A CN 99126428 A CN99126428 A CN 99126428A CN 99126428 A CN99126428 A CN 99126428A CN 1265923 A CN1265923 A CN 1265923A
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Abstract
一种油滴平均粒度小于100nm的毫微乳液,其含有一种当温度低于或等于45℃时为固体的选自甘油酯的表面活性剂和至少一种分子量大于400的油,油相含量与表面活性剂含量的重量比为2—10。所用表面活性剂如说明书中所述。所得乳液透明且储存稳定。在保持良好透明度和美容特性的同时,该乳液中可含有大量的油。本发明还涉及该毫微乳液在化妆品、皮肤学和眼科领域的应用。
Description
本发明涉及一种毫微乳液，该毫微乳液基于一种在温度低于或等于45℃时为固体的选自甘油脂肪酸酯的表面活性剂和至少一种分子量大于400的油，油相含量与表面活性剂含量的重量比为2-10。
本发明还涉及一种制备上述毫微乳液的方法及其在化妆品、皮肤学和/或眼科领域中的应用。该毫微乳液对储存稳定并且可以含有大量的油，同时保持良好的透明度和美容特性。
毫微乳液是水包油乳状液，其油滴具有极细的粒度，也就是说，数均粒度小于100nm。通常是在表面活性剂的存在下将存在于水相中的油相机械破裂来制备。对于毫微乳液，具体需要经过高压匀化器处理至少一次才能获得粒度极小的油滴。小粒度的油滴赋予毫微乳液区别于常规乳液的优越美容性质：透明并具有新质地。它们还可有效地容纳活性成分。
透明微乳液为所属技术领域所公知。与毫微乳液相反，微(滴)乳液严格来说不是乳液；它们是胶束被油溶胀的透明溶液，其中的油一般是链长很短的油(例如己烷或癸烷)，并且依赖同时存在的大量可形成胶束的表面活性剂和辅助表面活性剂来达到增溶。溶胀胶束的粒度很小，这是由于少量可增溶的油的缘故。胶束粒度极小是毫微乳液透明的原因。但是，与毫微乳液相反，微乳液可在组分混合时自发形成，除了简单的磁搅拌之外无需提供其他机械能。微乳液的主要缺点是其表面活性剂的比例高，以致用户难以忍受，并且在涂敷于皮肤上时产生粘着感。此外，其制剂范围一般很窄，而且它们对温度的稳定性很有限。
此外，已知在现有毫微乳液中含有由磷脂、水和油组成的两性脂质相。这些乳液的缺点表现在对常规储存温度(即0-45℃)储存不稳定。它们为黄色组合物并且散发出酸败气味，并在储存若干天后将更加严重。
已知可利用由亲水性表面活性剂和亲脂性表面活性剂的组合物制成的层状液晶涂层使毫微乳液稳定化。但是，这些组合物却难以制备。而且，所得毫微乳液表现出蜡质和成膜感，用户对此极感不适。
此外，文献EP-A-728,460公开了基于液态非离子两性脂质的毫微乳液。然而，这种毫微乳液的缺点表现在，当被涂敷于皮肤上时有粘着感。
所以需要使毫微乳液既不具有现有毫微乳液的缺点，又不出现上述微乳液的缺陷。
如今，本申请公司意外地发现，采用当温度低于或等于45℃时为固体的表面活性剂以及至少一种分子量大于400(＝400克/摩尔)的油可以制得新的毫微乳液，所述表面活性剂选自甘油脂肪酸酯，新的毫微乳液具有现有毫微乳液的全部优点并且克服了它们的缺点。
本发明的一个主题是一种含有分散在水相中的油相并且油滴数均粒度小于100nm的毫微乳液，其特征在于该毫微乳液含有一种当温度低于或等于45℃时为固体的选自甘油脂肪酸酯的表面活性剂和至少一种分子量大于400的油，其特征还在于，油相含量与表面活性剂含量的重量比例为2-10。
本发明所述的毫微乳液一般具有透明至蓝色的外观。对于其透明度，在600nm下测出的透光系数为10-90％，或用Hach Model 2100P便携式浊度计测出的浊度为60-600NTU，优选70-300NTU。
本发明毫微乳液的油滴的数均粒度小于100nm，优选为20-75nm，更优选40-60nm。减小油滴粒度能够促进活性成分渗透到皮肤表层中(载体作用)。
可用于本发明毫微乳液的、当温度低于或等于45℃时为固体的表面活性剂是甘油脂肪酸酯，这意味着本发明的毫微乳液只含有选自这些酯的表面活性剂，而不含有除甘油脂肪酸酯以外的其他任何表面活性剂。
可以在本发明毫微乳液中作为表面活性剂的甘油脂肪酸酯在低于或等于45℃的温度下为固体，并且，具体可选自由至少一种含有16-22个碳原子的饱和直链烷基链的酸与1-10个甘油单元形成的酯类化合物。本发明毫微乳液中可以采用一种或多种上述甘油脂肪酸酯。
上述酯具体可选自硬脂酸酯、山萮酸酯、花生酸酯、棕榈酸酯及其混合物。优选硬脂酸酯和棕榈酸酯。
作为可用于本发明毫微乳液的表面活性剂，值得提及的例子是：十甘油的单硬脂酸酯、二硬脂酸酯、三硬脂酸酯和五硬脂酸酯(CTFA名称：聚甘油基(Polyglyceryl)-10硬脂酸酯，聚甘油基-10二硬脂酸酯，聚甘油基-10三硬脂酸酯，聚甘油基-10五硬脂酸酯)，例如Nikko公司分别按商品名Nikkol Decaglyn 1-S、2-S、3-S和5-S出售的产品；二甘油单硬脂酸酯(CTFA名称：聚甘油基-2硬脂酸酯)，例如Nikko公司以商品名Nikkol DGMS出售的产品。
在本发明毫微乳液中，所述表面活性剂的用量可例如是0.2-15％(重量)，优选1-8％(重量)，以毫微乳液的总重量计。
油相含量对表面活性剂含量的重量比例是2-10，并优选3-6。术语“油相含量”应理解为油相组分的总量，其中不包括表面活性剂的量。
本发明的毫微乳液含有至少一种分子量大于400的油。分子量大于400的油选自动物油或植物油，矿物油，合成油和硅油，及其混合物。此类油中值得提及的例子是：棕榈酸异鲸蜡酯、硬脂酸异鲸蜡酯、鳄梨油或西蒙得木油。
此外，所述油相可任选地含有其它油类，特别是分子量小于400的油类。这些油也可以选自动物油或植物油、矿物油、合成油和硅油。作为分子量小于400的油，值得提及的例子是：异十二烷、异十六烷、挥发性硅油、肉豆蔻酸异丙酯、棕榈酸异丙酯或C11-C13异链烷烃。
所述油相除了上述油类以外还可以含有脂肪物质，例如脂肪醇，如硬脂醇、鲸蜡醇和山萮醇；脂肪酸，如硬脂酸、棕榈酸和山萮酸；氟化油类，蜡，树胶及其混合物。
本发明的毫微乳液含有占毫微乳液总重量2-40％(重量)的油相，更优选5-30％(重量)。分子量大于400的油在油相中的优选比例为至少为40％(重量)。
根据本发明的具体实施方案，本发明的毫微乳液还另外含有一种或多种离子两性脂质。
适用于本发明毫微乳液的离子两性脂质优选自阴离子两性脂质、阳离子两性脂质和烷基磺酸衍生物。
阴离子两性脂质更优选自：
-碱性联十六烷基和联十四烷基磷酸盐；
-碱性胆甾醇硫酸盐；
-碱性胆甾醇磷酸盐；
-脂酰氨基酸及其盐，例如酰基谷氨酸一钠盐和二钠盐，如由Ajinomoto公司以商品名称酰基谷氨酸盐HS21出售的N-硬脂酰基-L-谷氨酸二钠盐；
-磷脂酸钠盐；
-磷脂。
所述烷基磺酸衍生物更优选自下式(I)所示的烷基磺酸衍生物：
其中R代表含有16-22个碳原子的烷基基团，具体如C16H33和C18H37，该烷基可取混合烷基或独立烷基，并且M为碱金属，例如钠。
所述阳离子两性脂质更优选自：季铵盐、脂肪胺及其盐。
所述季铵盐可例如是：
-那些如通式(II)所示的季铵盐：
其中R1-R4基团可以相同或不同，代表含有1-30个碳原子的直链或支链脂族基，或芳香基团，如芳基或烷芳基。脂族基团可以含有杂原子，具体如氧、氮、硫或卤素。脂族基团例如可选自：烷基、烷氧基、聚氧化(C2-C6)亚烷基、烷基酰氨基、(C12-C22)烷基酰氨基(C2-C6)烷基、乙酸(C12-C22)烷基酯或含有约1-30个碳原子的羟烷基；X是阴离子，选自卤素阴离子、磷酸根、乙酸根、乳酸根、(C2-C6)烷基硫酸根、或烷基或烷芳基磺酸根。另一方面，作为式(II)的季铵盐，还优选四烷基氯化铵类化合物，例如氯化二烷基二甲基铵或氯化烷基三甲基铵，其中所述烷基含有约12-22个碳原子，具体如氯化山萮基三甲基铵、氯化二硬脂基二甲基铵、氯化鲸蜡基三甲基铵和氯化苄基二甲基硬脂基铵，或，氯化硬脂基酰氨丙基二甲基(乙酸肉豆蔻酯)铵(由Van Dyk公司以商品名称《Ceraphyl 70》出售)。
-咪唑啉鎓季铵盐，例如是那些如下式(III)所示的咪唑啉鎓季铵盐：
其中R5代表含有8-30个碳原子的链烯基或烷基，例如衍生自牛油脂肪酸的基团；R6代表氢原子、含有1-4个碳原子的烷基或含有8-30个碳原子的链烯基或烷基；R7代表含有1-4个碳原子的烷基；R8代表氢原子或含有1-4个碳原子的烷基；和X是阴离子，选自卤素阴离子、磷酸根、乙酸根、乳酸根、烷基硫酸根、或烷基或烷芳基磺酸根。优选R5和R6代表含有12-21个碳原子的链烯基或烷基的混合物，例如衍生自牛油脂肪酸的基团；优选R7代表甲基并且R8代表氢。这种产品可例如是Rewo公司以商品名《Rewoquat W 75》出售的产品。
-如下式(IV)所示的季二铵盐：
其中R9代表含有约16-30个碳原子的脂族基团；R10、R11、R12、R13和R14选自氢或含有1-4个碳原子的烷基；和X是阴离子，选自卤素阴离子、乙酸根、磷酸根、硝酸根和甲基硫酸根。
所述季二铵盐具体包括二氯化丙烷牛油二铵。
根据本发明的一个优选实施方案，使用脂酰氨基酸作为离子两性脂质。
可以将所述离子两性脂质引入毫微乳液两相中的一个相内。当它们存在于本发明毫微乳液中时，优选其浓度是毫微乳液总重量的0.01-5％(重量)，更优选0.25-1％(重量)。
本发明所述的乳液可以含有用于改进制剂透明度的添加剂。
这些添加剂优选选自：
-含有1-8个碳原子，优选2-6个碳原子的低级醇，如乙醇；
-二醇类化合物，例如甘油、丙二醇、1，3-丁二醇、一缩二丙二醇、戊二醇、异戊二烯二醇，和含有4-16个，优选8-12个环氧乙烷单元的聚乙二醇；
-糖类，例如葡萄糖、果糖、麦芽糖、乳糖或蔗糖。
上述添加剂也可以作为混合物使用。当本发明毫微乳液含有上述添加剂时，优选所用添加剂的浓度是毫微乳液总重量的0.01-3％(重量)，更优选是毫微乳液总重量的5-20％(重量)。优选上述醇类和/或糖类的用量是毫微乳液总重量的5-20％(重量)，并且优选二醇(类)的用量是毫微乳液总重量的5-15％(重量)。
此外，上述醇类化合物的用量大于或等于15％(重量)时可得到无防腐剂乳液。
可将定义如上的毫微乳液应用于对此类组合物有效的任何领域。它们可以组成具体的局部用组合物，特别是化妆品或皮肤用组合物。也可以将其用作眼科赋形剂。此外，在制药领域，它们可以构成经口服、非肠道或透皮给药的药物组合物。
因此，本发明的另一个主题是一种局部用组合物，其特征在于含有如上定义的毫微乳液。
一种局部或药用组合物，其中含有生理可接受介质，也就是与皮肤、粘膜、头皮、眼睛和/或头发相容的介质。
本发明的又一个主题是一种眼科赋形剂，其特征在于含有如上定义的毫微乳液。
本发明的另一个主题是一种药物组合物，其特征在于含有如上定义的毫微乳液。
本发明所述的毫微乳液可以含有具有美容、皮肤或眼科作用的水溶性或脂溶性活性成分。脂溶性活性成分存在于乳液的油滴内，而水溶性活性成分存在于乳液的水相中。值得提及的活性成分例如是：维生素，如维生素E及其衍生物，具体如其酯类化合物；维生素原，如泛醇；湿润剂和防晒剂。
作为眼用活性成分，值得提及的例如是：青光眼治疗药，如倍他洛尔；抗生素，如无环鸟苷；抗变态反应药；抗炎药，如布洛芬及其盐，双氯芬酸及其盐，或消炎痛；或抗病毒药。
本发明的毫微乳液可以以洗液、浆液、霜剂、奶液或花露水形式提供，并且含有常用于化妆品、皮肤用和眼科领域的辅料，例如胶凝剂、防腐剂、抗氧剂和香料。它们还可以是洗眼液形式，尤其是用于眼科应用。
在所用胶凝剂中值得提及的是纤维素衍生物、藻类衍生物，天然树胶及合成聚合物，例如羧乙烯酸的聚合物和共聚物，如Goodrich公司以商品名Carbopol出售的那些产品。
本发明的另一个主题是一种制备如上定义的毫微乳液的方法，该方法包括，在10-80℃的温度下经剧烈搅拌将水相和油相混合，然后在6×107Pa-18×107Pa(高压匀化器)的适当压力下将上述化合物匀化。优选的剪切为2×106s-1-5×108s-1，更优选1×108s-1-3×108s-1(s-1代表秒-1)。
可将本发明的毫微乳液用于例如皮肤、面部和/或头皮的护理、处理或化妆。
所以，本发明的另一个主题是如上定义的毫微乳液在用于护理、处理和/或化妆皮肤、面部和/或头皮中的美容用途。
此外，也可以用本发明的毫微乳液护理和/或处理头发。它可以将油沉积在头发上，从而赋予后者光泽并对美发更耐受，且没有使头发稀少。作为预处理，所述毫微乳液能够改进染色或长效卷发的效果。
所以，本发明的另一个主题是如上定义的毫微乳液在头发护理和/或处理中的美容用途。
本发明的毫微乳液尤其可使皮肤、粘膜和/或头皮更湿润，并且更适合用来处理干性皮肤。
因此，本发明的另一个主题是一种护理和/或润湿皮肤、粘膜和/或头皮的美容方法，其特征在于将如上定义的毫微乳液涂敷在皮肤、粘膜和/或头皮上。
本发明还涉及本发明的毫微乳液在制造用于处理干性皮肤的皮肤用组合物中的应用。
最后，本发明还涉及本发明的毫微乳液在制造眼用组合物中的应用。
下列实施例可以使本发明更易于理解，但是它们不起限定作用。所示的量为重量百分数。
实施例1：流体卸妆剂
油相
-Nikkol Decaglyn 3-S(Nikko公司) 4.5％
-N-硬脂酰基-L-谷氨酸二钠盐
(Ajinomoto公司出售的酰基谷氨酸盐HS21) 0.5％
-硬脂酸异鲸蜡酯(分子量＝508) 10％
-肉豆蔻酸异丙酯(分子量＝270) 5％水相-甘油 5％-一缩二丙二醇 10％-水 65％得到一种透明的毫微乳液，液滴粒度为50nm，浊度为176 NTU。实施例2：保湿流体油相-Nikkol Decaglyn 2-S(Nikko公司) 4％-N-硬脂酰基-L-谷氨酸二钠盐(Ajinomoto公司出售的酰基谷氨酸盐HS21) 0.5％-霍霍巴油(分子量，900级) 9％-挥发性硅油 6％-硬脂酸异鲸蜡酯(分子量＝508) 9％水相-甘油 5％-一缩二丙二醇 10％-水 55％得到一种透明的毫微乳液，液滴粒度为52nm，浊度为230 NTU。
Claims (27)
1.含有分散在水相中的油相并且油滴数均粒度小于100nm的毫微乳液，其特征在于该毫微乳液含有一种当温度低于或等于45℃时为固体的选自甘油脂肪酸酯的表面活性剂和至少一种分子量大于400的油，其特征在于，油相含量与表面活性剂含量的重量比例为2-10。
2.权利要求1所述的毫微乳液，其特征在于该毫微乳液的浊度为60-600NTU。
3.权利要求1或2所述的毫微乳液，其特征在于所述表面活性剂的量是该毫微乳液总重量的0.2-15％(重量)，并且优选1-8％(重量)。
4.上述权利要求任一项所述的毫微乳液，其特征在于油相含量和表面活性剂含量的重量比例为3-6。
5.上述权利要求任一项所述的毫微乳液，其特征在于油滴的平均粒度为20-75nm。
6.上述权利要求任一项所述的毫微乳液，其特征在于所述表面活性剂选自由至少一种含有16-22个碳原子的饱和或不饱和、直链或支链烷基链的酸与1-10个甘油单元形成的酯。
7.上述权利要求任一项所述的毫微乳液，其特征在于所述表面活性剂选自十甘油的单硬脂酸酯、二硬脂酸酯、三硬脂酸酯和五硬脂酸酯以及双甘油单硬脂酸酯。
8.上述权利要求任一项所述的毫微乳液，其特征在于所述的分子量大于400的油选自动物油或植物油，矿物油，合成油和硅油，及其混合物。
9.上述权利要求任一项所述的毫微乳液，其特征在于所述油相还含有至少一种分子量小于400的油。
10.上述权利要求任一项所述的毫微乳液，其特征在于所述油相含有至少占所述油相总重量40％(重量)的分子量大于400的油。
11.上述权利要求任一项所述的毫微乳液，其特征在于油相的含量是该毫微乳液总重量的2-40％(重量)。
12.上述权利要求任一项所述的毫微乳液，其特征在于该毫微乳液中还含有至少一种离子两性脂质，所述脂质选自阴离子两性脂质、阳离子两性脂质和烷基磺酸衍生物。
13.前述权利要求所述的毫微乳液，其特征在于所述离子两性脂质选自：
-碱性联十六烷基和联十四烷基磷酸盐；
-碱性胆甾醇硫酸盐；
-碱性胆甾醇磷酸盐；
-脂酰氨基酸盐；
-磷脂酸钠盐；
-磷脂；
-式(I)所示的烷基磺酸衍生物：
其中R代表C16-C22烷基基团，该烷基是混合烷基或独立烷基，和M为碱金属；
-季铵盐，脂肪胺及其盐；
及其混合物。
14.权利要求12或13所述的毫微乳液，其特征在于离子两性脂质的量是毫微乳液总重量的0.01-5％(重量)。
15.上述权利要求任一项所述的毫微乳液，其特征在于其含有能够改进透明度的添加剂，所述添加剂选自低级醇类、二醇类、糖类及其混合物。
16.前述权利要求所述的毫微乳液，其特征在于所述添加剂的浓度是毫微乳液总重量的5-20％(重量)。
17.上述权利要求任一项所述的毫微乳液，其特征在于其含有美容、皮肤用或眼科用活性成分。
18.局部用组合物，其特征在于其含有权利要求1-17任一项所述的毫微乳液。
19.眼科用赋形剂，其特征在于其含有权利要求1-17任一项所述的毫微乳液。
20.药物组合物，其特征在于其含有权利要求1-17任一项所述的毫微乳液。
21.权利要求1-17任一项所述的毫微乳液在皮肤、面部和/或头皮的护理、处理和/或化妆中的美容用途。
22.权利要求1-17任一项所述的毫微乳液在护理和/或处理头发中的美容用途。
23.一种护理和/或湿润皮肤、粘膜和/或头皮的美容方法，其特征在于将权利要求1-17任一项所述的毫微乳液涂敷在皮肤、粘膜和/或头皮上。
24.权利要求1-17任一项所述的毫微乳液在制造用于处理干性皮肤的皮肤组合物中的应用。
25.权利要求1-17任一项所述的毫微乳液在制造眼用组合物中的应用。
26.一种制备权利要求1-17任一项所述的毫微乳液的方法，该方法包括，在10-80℃的环境温度下经剧烈搅拌将水相和油相混合，然后在6×107Pa-18×107Pa的压力下将上述化合物匀化。
27.前述权利要求所述的方法，其特征在于所述剪切为2×106s-1-5×108s-1。
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| FR9815950A FR2787326B1 (fr) | 1998-12-17 | 1998-12-17 | Nanoemulsion a base d'esters gras de glycerol, et ses utilisations dans les domaines cosmetique, dermatologique et/ou ophtalmologique |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPS54134793A (en) † | 1978-04-12 | 1979-10-19 | Sumitomo Chem Co Ltd | Preparation of vinyl chloride resin |
| EP0041703B1 (en) † | 1980-06-05 | 1985-05-08 | Sumitomo Naugatuck Co., Ltd. | Process for preparing copolymers |
| DE3421468A1 (de) * | 1984-06-08 | 1985-12-19 | Dr. Rentschler Arzneimittel Gmbh & Co, 7958 Laupheim | Lipidnanopellets als traegersystem fuer arzneimittel zur peroralen anwendung |
| IE60024B1 (en) † | 1987-02-03 | 1994-05-18 | Stiefel Laboratories Ltd | Microemulsions |
| CH677886A5 (zh) † | 1989-06-26 | 1991-07-15 | Hans Georg Prof Dr Weder | |
| JP2785981B2 (ja) * | 1989-11-20 | 1998-08-13 | 株式会社資生堂 | 乳化組成物 |
| DE4039063A1 (de) † | 1990-12-07 | 1992-06-11 | Wella Ag | Haarkurmittel in form einer mikroemulsion |
| DE69328368T2 (de) † | 1992-08-28 | 2000-08-10 | Pharmos Corp., New York | Emulsionen im submikron-bereich als vehikel zur arzneistoffverabreichung am auge |
| AU6712394A (en) † | 1993-04-23 | 1994-11-21 | Croda, Inc. | Microemulsified hair treatment products and methods of making same |
| US5576016A (en) * | 1993-05-18 | 1996-11-19 | Pharmos Corporation | Solid fat nanoemulsions as drug delivery vehicles |
| FR2709666B1 (fr) † | 1993-09-07 | 1995-10-13 | Oreal | Composition cosmétique ou dermatologique constituée d'une émulsion huile dans eau à base de globules huileux pourvus d'un enrobage cristal liquide lamellaire. |
| ES2094688B1 (es) † | 1994-08-08 | 1997-08-01 | Cusi Lab | Manoemulsion del tipo de aceite en agua, util como vehiculo oftalmico y procedimiento para su preparacion. |
| FR2725369B1 (fr) † | 1994-10-07 | 1997-01-03 | Oreal | Composition cosmetique ou dermatologique constituee d'une emulsion huile dans eau a base de globules huileux pourvus d'un enrobage cristal liquide lamellaire |
| FR2730932B1 (fr) * | 1995-02-27 | 1997-04-04 | Oreal | Nanoemulsion transparente a base de lipides amphiphiles non-ioniques fluides et utilisation en cosmetique ou en dermopharmacie |
| DE19509079A1 (de) † | 1995-03-15 | 1996-09-19 | Beiersdorf Ag | Kosmetische oder dermatologische Mikroemulsionen |
| AU6614296A (en) † | 1995-07-22 | 1997-02-18 | Ciba Specialty Chemicals Holding Inc. | Sunscreen compositions |
| JP3489703B2 (ja) † | 1995-10-23 | 2004-01-26 | 株式会社ノエビア | 微細エマルション組成物 |
| FR2741263B1 (fr) † | 1995-11-22 | 1997-12-26 | Oreal | Composition comprenant une dispersion aqueuse de vesicules lipidiques encapsulant un filtre uv a fonction acide et utilisations en application topique |
| US5766575A (en) † | 1996-06-14 | 1998-06-16 | Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. | Method and composition for skin lightening |
| ES2256868T3 (es) † | 1996-07-25 | 2006-07-16 | Beiersdorf Aktiengesellschaft | Preparado para el cuidado del cabello en forma de microemulsion transparente o translucida del tipo aceite-en-agua. |
| DE19641672A1 (de) † | 1996-10-10 | 1998-04-16 | Beiersdorf Ag | Kosmetische oder dermatologische Zubereitungen auf der Basis von ethylenoxidfreien und propylenoxidfreien Emulgatoren zur Herstellung von Mikroemulsionsgelen |
| WO1998047464A1 (en) † | 1997-04-18 | 1998-10-29 | Avon Products, Inc. | Water-thin emulsion formed by high pressure homogenization process |
-
1998
- 1998-12-17 FR FR9815950A patent/FR2787326B1/fr not_active Expired - Lifetime
-
1999
- 1999-11-23 EP EP99402915.5A patent/EP1010416B2/fr not_active Expired - Lifetime
- 1999-11-23 ES ES99402915T patent/ES2167993T3/es not_active Expired - Lifetime
- 1999-11-23 DE DE69900328.8T patent/DE69900328T3/de not_active Expired - Lifetime
- 1999-11-23 AT AT99402915T patent/ATE206300T1/de not_active IP Right Cessation
- 1999-12-08 BR BR9907333-1A patent/BR9907333A/pt not_active IP Right Cessation
- 1999-12-13 KR KR1019990057231A patent/KR100358548B1/ko not_active IP Right Cessation
- 1999-12-13 JP JP35375299A patent/JP3618613B2/ja not_active Expired - Fee Related
- 1999-12-16 US US09/461,753 patent/US6541018B1/en not_active Expired - Lifetime
- 1999-12-16 CA CA002292797A patent/CA2292797C/fr not_active Expired - Fee Related
- 1999-12-16 CN CNB991264282A patent/CN1155365C/zh not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107485602A (zh) * | 2009-12-03 | 2017-12-19 | 爱尔康研究有限公司 | 眼用乳剂 |
Also Published As
| Publication number | Publication date |
|---|---|
| US6541018B1 (en) | 2003-04-01 |
| DE69900328T3 (de) | 2016-11-03 |
| BR9907333A (pt) | 2001-02-06 |
| CA2292797C (fr) | 2003-04-15 |
| ATE206300T1 (de) | 2001-10-15 |
| FR2787326B1 (fr) | 2001-01-26 |
| FR2787326A1 (fr) | 2000-06-23 |
| EP1010416B1 (fr) | 2001-10-04 |
| EP1010416B2 (fr) | 2015-02-11 |
| DE69900328T2 (de) | 2002-04-25 |
| CN1155365C (zh) | 2004-06-30 |
| ES2167993T3 (es) | 2002-05-16 |
| JP3618613B2 (ja) | 2005-02-09 |
| EP1010416A1 (fr) | 2000-06-21 |
| CA2292797A1 (fr) | 2000-06-17 |
| DE69900328D1 (de) | 2001-11-08 |
| KR100358548B1 (ko) | 2002-10-25 |
| JP2000178132A (ja) | 2000-06-27 |
| KR20000048108A (ko) | 2000-07-25 |
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