CN1507852A - 抗坏血酸衍生物作为漂白剂的美容用途 - Google Patents
抗坏血酸衍生物作为漂白剂的美容用途 Download PDFInfo
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- CN1507852A CN1507852A CNA2003101246725A CN200310124672A CN1507852A CN 1507852 A CN1507852 A CN 1507852A CN A2003101246725 A CNA2003101246725 A CN A2003101246725A CN 200310124672 A CN200310124672 A CN 200310124672A CN 1507852 A CN1507852 A CN 1507852A
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Abstract
本发明涉及组合物中至少一种(I)式所示的化合物作为皮肤和/或头和/或其它毛发的褪色剂和/或漂白剂在美容或皮肤学方面的用途:本发明还涉及人类皮肤、头发或其它毛发的美容方法,包括将一种含有(I)式所示的上述化合物的美容组合物应用于皮肤或头发或其它毛发。
Description
技术领域
本发明涉及抗坏血酸酯在组合物,尤其是美容组合物中的用途,所述的抗坏血酸衍生物和/或所述组合物用于漂白人类皮肤、头发或其它毛发。
本发明还涉及抗坏血酸酯在制备用于人皮肤、头发或其它毛发褪色的组合物,尤其是皮肤学组合物中的用途。
背景技术
人皮肤的颜色依赖于很多不同的因素,特别是季节、人种和性别,它主要取决于黑素细胞产生的黑色素的性质和浓度。黑素细胞是特化细胞,它通过专门的细胞器官即黑素体合成黑色素。另外,在黑素体不同的生命阶段,特定个体的皮肤颜色会变深和/或在皮肤上产生色斑,尤其是在手部皮肤上,使得皮肤的颜色不一致。这些色斑也是由于皮肤表层角质细胞中高浓度的黑色素造成的。
同样地,头发和其它毛发的颜色也是由于黑色素造成的。当头发或其它毛发的颜色较深时,有些人希望能够将它们的颜色变浅。这对于浅色时tx深色时更不显眼的毛发来说是有利的。。
非常希望采用高效的无害局部褪色物质,来处理由于黑素细胞过度活跃造成的区域性过度色素沉积,如:怀孕期间产生的(“妊娠斑”或黄褐斑)或雌激素-孕激素避孕期间出现的特发性黑斑病,由良性黑素细胞过度活跃和增殖导致的局部过度色素沉积,如已知是光化性斑的老年色斑,可能由于光过敏作用或病变化愈合以及某些白斑病而导致的偶然性过度色素沉积,如:白癜风。对于后者,(愈合会导致疤痕,使这部分皮肤显得较白),由于无法再使已被破坏的这部分皮肤沉积色素,因此其余正常的皮肤需要进行褪色以赋予皮肤整体上均匀一致的肤色。
皮肤色素沉积形成的机理,即黑色素的形成,是特别复杂的,以图表的方式包括以下主要步骤:
酪氨酸→二羟基苯丙氨酸→多巴醌→多巴色素→黑色素
酪氨酸酶(单酚二羟基苯基丙氨酸:氧气氧化还原酶EC 1.14.18.1)是涉及该一系列反应中必不可少的酶。它通过其水解酶活性专门催化酪氨酸转化为多巴(二羟基苯丙氨酸)的反应,并通过其氧化酶活性专门催化多巴转化为多巴醌的反应。该酪氨酸酶仅在特定的生物学因素作用下,处于成熟态时才起作用。
表皮中,黑素细胞被包含在表皮黑色素单元中,该单元包括一个被约36个邻近的角质细胞包围着的黑素细胞。在光敏类型(photo tpye)方面没有差别的所有个体,在给定的皮肤区域,有着大致相同数量的黑素细胞。色素沉积的人种差别并不是由黑素细胞的数量,而是由其黑素体的性质而导致的。这些黑素体聚集成为联合体,并且其尺寸很小。它们是高度分化的细胞器官,其主要功能是产生黑色素。它们以称为前黑素体的球状液泡的形式从内质网中产生。该前黑素体包括一种无定形蛋白质基质,但是没有产生黑色素的酶。在前黑素体成熟过程中,该无定形蛋白质基质沿着黑素体纵轴方向呈纤维状结构排列。对应于黑素化程度,黑素体的发展可以区分为四个阶段。黑色素均匀地沉积在黑素体内部的纤维状网络结构上,细胞器官的不透明程度提高达到饱和点。随着黑素体中黑色素的逐渐形成,这些黑素体从细胞核周围区域迁移到黑素细胞树突的末端。通过噬菌作用,这些树突的末端被角质细胞俘获,膜被降解,黑素体重新分布在角质细胞中。这样,黑素细胞的树突延伸体在转移黑色素过程中起了重要的作用。
尽管黑色素的水平因人而异,但是在黑色或白色皮肤中,酪氨酸酶的量却并没有大的不同,并且酪氨酸酶信使RNA的水平也是完全相同的。由此,黑素形成的不同是由酪氨酸酶活性或角质细胞吞噬黑素细胞能力的不同而造成的,或者换句话说是由树突延伸体的数量而造成的。
如果一种物质能够直接对生成黑素的表皮黑素细胞的活力起作用,则该物质被认为可以用于褪色,例如,通过改变树突延伸体的形态,和/或通过抑制黑素形成中的一种酶或者作为化学物质的一种结构类似物插入到黑素合成链中,干扰黑素生物合成中的一个步骤,使得这个反应链被阻断,从而保证了褪色。
通常用作褪色剂的物质比较具体的是,对苯二酚及其衍生物,特别是其醚,如:对苯二酚单甲醚和单乙醚。尽管它们具有一定的功效,不幸的是这些化合物由于其毒性而难免有一些副作用,这使得它们使用起来很难,甚至会有危险。其毒性是由于它们通过杀死细胞而干扰了色素形成的基本机制,这会造成打乱其生物环境的危险,并随后迫使皮肤产生毒素以消除它们。
因此,对苯二酚是一种对黑素细胞特别有刺激性和细胞毒性的化合物,很多技术人员都设想到将其全部或部分替代。
因而需要寻求一种物质,该物质不涉及黑素形成机制,但是它可以在上游通过阻止酪氨酸酶的活化而对其产生作用,并且因此毒性较低。曲酸通常被用作酪氨酸酶活化抑制剂,这种酸能够螯合该酶活力中心的铜。不幸的是,该化合物在溶液中不稳定,这在某种程度上使得其组合物的生产复杂化了。
很多年来人们已经知道抗坏血酸或其某些衍生物在褪色方面具有活性。为了解释它们对于色素形成的作用,抗坏血酸对于酪氨酸酶的抑制效果已经得以证明(J.Soc.Cosmet.Chem.,42,1991,361-368页)。最近,研究也表明抗坏血酸磷酸镁对于黑色素转移有效果,并且能够减少黑素细胞的树突(Pigment.Cell.Res.,13,2000,89-98和190-192页),从而引发褪色的效果。这种效果可以与阿魏酸所取得的效果相媲美。
还需要一种用于漂白人类皮肤、头发和/或其它毛发的新型试剂,它的效果要像已知的试剂一样有效,但不具有那些已知试剂的缺点,即:对皮肤无刺激性、无毒和/或不过敏,同时在组合物中稳定,或选择性地具有增强的作用,以便于可以以较少的剂量使用,从而显著地减少可观察到的副作用。
基于上述考虑,本申请人意外惊人地发现,某些抗坏血酸酯衍生物即使在很低的浓度仍具有优良的褪色活性,而没有显示任何的细胞毒性。这些衍生物还具有同时对色素沉积机制的几个因素起作用的优点。它们通过抑制黑色素的生物合成和抑制黑素细胞树突而起作用,从而可以减少黑色素向邻近的角质细胞转移的数量。
发明内容
因此,本发明的一个主题是至少一种(I)式所示的化合物在组合物中作为皮肤和/或头发和/或其它毛发的漂白剂的美容用途:
其中,
R1和R4独立地表示一个氢原子或一个选自下列的基团:甲基、乙基、异丙基、阿魏基、苄基、三甲基甲硅烷基、三苯基甲硅烷基、叔丁基二甲基甲硅烷基、乙酰基、丙酰基、棕榈酰基、脂酰基、苯甲酰基,SO3H、O=P(OH)OH和CH3NHCO-,R2和R3独立地表示一个氢原子或一个选自下列的基团:甲基、乙基、异丙基、阿魏基、苄基、三甲基甲硅烷基、三苯基甲硅烷基、叔丁基二甲基甲硅烷基、乙酰基、丙酰基、棕榈酰基、脂酰基、苯甲酰基,SO3H、O=P(OH)OH和CH3NHCO-,或者,R2和R3与其连接的氧一起形成5元环或6元环基团,R2和R3中至少有一个不为氢原子。
本发明的一个有利的方面涉及R1表示一个氢原子的(I)式所示的化合物的用途。
在本发明的另一个有利的方面,所用的(I)式所示的化合物中R4表示一个氢原子或乙酰基。
优选的(I)式所示的化合物中R2和R3与其连接的氧一起形成异亚丙基。
特别适合用于本发明的(I)式所示的一种化合物是(A)式所示的5-(2,2-二甲基[1,3]二氧戊环-4-基)-4-羟基-2-氧代-2,5-二氢-3-呋喃基3-[(4-乙酸基-3-甲氧基)苯基]丙烯酸酯:
另一个特别适合用于本发明的(I)式所示的化合物是(B)式所示的5-(2,2-二甲基[1,3]二氧戊环-4-基)-4-羟基-2-氧代-2,5-二氢-3-呋喃基3-[(4-羟基-3-甲氧基)苯基]丙烯酸酯:
本领域熟练的技术人员可以通过常规手段合成(I)式所示的化合物,特别是可以使用专利申请EP0664290中描述的方法进行合成。化合物A在所述专利申请的实施例1第4步有所描述。
本发明还涉及至少一种上述定义的(I)式所示的化合物在组合物中作为皮肤防晒剂的美容用途。
本发明还涉及至少一种上述定义的(I)式所示的化合物在制备皮肤和/或头发和/或其它毛发褪色用皮肤病学组合物方面的用途。
本发明的主题还涉及漂白人类皮肤和/或头发和/或其它毛发的美容方法,包括将含有上述定义的(I)式所示化合物的美容组合物应用于皮肤和/或头发和/或其它毛发。
本发明中所述衍生物的用量显然取决于所希望获得的效果。
作为例子,该用量的范围例如为:以组合物总重量计0.001%-10%,优选0.01%-5%,特别地0.1%-2%。
本发明的组合物特别地可进行局部使用。它还包括生理学上可接受的介质,即:与皮肤,包括头皮、粘膜、头发、其它毛发和/或眼睛,相容的介质,并且特别地可以组成美容或皮肤病学组合物。
所述组合物可以继而包含任何通常应用于该用途的成分。
特别地应该提及的是水、溶剂、矿物油、动物和/或植物油、蜡、颜料、填料、表面活性剂、美容或皮肤活性剂、UV阻隔剂、聚合物、胶凝剂和防腐剂。
当本发明的组合物为乳液时,油相部分可以占组合物总重量的5-80%,优选5-50%。乳液组合物所用的油脂、乳化剂和共乳化剂选自本领域中通常使用的那些物质。组合物所用的乳化剂和共乳化剂占组合物总重量的0.3-30%,优选0.5-20%。
无需说明,本领域熟练技术人员会小心地选择这或这些任选的额外添加化合物和/或其用量,使得根据本发明得到的化合物的优点不会或基本不会受到拟加入的添加物的影响。
本发明的组合物可以采用任何通常用于美容和皮肤学的配药形式,特别地可以采用任选的凝胶水性或水-醇溶液、任选的两相洗液型分散液、水包油或油包水或多重乳液、水凝胶、借助于小球体将油分散在水相中的分散液,所述的小球体可能为聚集的纳米颗粒,如:纳米球体和纳米胶囊或最好是离子和/或非离子型的脂质囊泡(lipid vesicles)。
该组合物可以相对有流动性,外观为白色或有色的霜、油膏、乳液、洗剂、浆、膏或泡沫。它可以任选地以气雾剂的形式用于皮肤或头发。它也可以为固体的形式和,例如:棒条(stick)的形式。它可以用作护理品和/或化妆用品。它也可以为洗发剂或调节剂的形式。
所述组合物可以组成清洁、保护、处理或护理霜用于脸部、手部、脚部、主要的解剖学皱褶或身体(例如:日霜、晚霜、卸装霜、粉底霜或防晒霜);也可以是粉底液、卸装乳液、身体保护或护理乳液或防晒乳;还可以是护肤洗液、凝胶或摩丝,或作为清洁洗剂。
在本发明的一个有利的方面,所用的组合物还包含至少一种脱皮剂,和/或至少一种镇静剂和/或至少一种有机的光防护剂和/或至少一种矿物的光防护剂。
“脱皮剂”一词的含义是任何具有下列作用的化合物:
-通过促进脱落而直接对脱皮起作用,例如:β-羟基酸、特别是水杨酸及其衍生物(包括5-n-辛酰基水杨酸);α-羟基酸,例如:乙二醇酸、柠檬酸、乳酸、酒石酸、马来酸或扁桃酸;脲;2,5-二羟基苯甲酸;海藻寡糖;肉桂酸;日本山茶(Saphora japonoica)提取物;白藜芦醇;
-或者通过对脱皮或角质桥粒降解的酶、糖苷酸、角质层胰凝乳蛋白酶(SCCE),或其它蛋白酶(胰蛋白酶、类胰凝乳蛋白酶)起作用。可以提及的用作螯合矿物盐的试剂是:EDTA;N-酰基-N,N’,N’-乙二胺三乙酸;氨基磺酸化合物,特别是(N-2-羟基-乙基哌嗪-N-2-乙烷)磺酸(HEPES);2-氧代噻唑烷-4-羧酸的衍生物(原半胱氨酸);如氨基乙酸之类的α-氨基酸的衍生物(如EP0852949中描述的,和BASF公司出售的商品名为Trilon M的甲基氨基乙酸二醋酸钠);蜂蜜;糖衍生物,如:O-辛酰基-6-D-麦芽糖和N-乙酰基葡萄糖胺。
作为用于本发明的组合物中的镇静剂,可以提及的是:五环的三萜和含有它们的植物(例如:光果甘草)的提取物,如:β-甘草酸和其盐和/或衍生物(甘草亭酸monogluoronide,硬脂酰甘草亭酸酯或3-硬酯酰基-氧代甘草亭酸)、乌索酸和其盐、石竹素和其盐、桦木酸和其盐、牡丹和/或芍药的提取物、水杨酸盐特别是水杨酸锌、Godif公司的海藻糖、糖的海带提取物、低芥酸菜籽油、红没药醇和春黄菊的提取物、尿囊素、SEPPIC的海泡石(Sepivital)EPC(维他命E和C的磷酸二酯)、ω-3不饱和油脂如麝香玫瑰油、黑醋栗油、ecchium油、鱼油、浮游生物提取物、辛酰基氨基乙酸、SEPPIC的Seppicalm VG(棕榈酰脯氨酸和睡莲)、臀果木的提取物、印乳香的提取物、centipeda cunnighami的提取物、向日葵提取物、亚麻的提取物、生育三烯酚类(tocotrienols)、光滑可乐果的提取物、胡椒醛、丁子香提取物、柳兰的提取物、芦荟、假马齿苋的提取物、植物甾醇类、可的松、氢化可的松、吲哚美辛和倍它米松。
有机的光保护剂特别地选自氨茴酸酯;肉桂酸衍生物;二苯甲酰甲烷衍生物;水杨酸衍生物;樟脑衍生物;三嗪衍生物,例如那些在专利申请US4367390、EP863145、EP517104、EP570838、EP796851、EP775698、EP878469、EP933376、EP507691、EP507692、EP790243和EP944624中描述的;二苯(甲)酮衍生物;β,β-二苯基丙烯酸酯衍生物;苯并三唑衍生物;亚苄基丙二酸酯衍生物;苯并咪唑衍生物;咪唑啉;双吲哚衍生物,例如在专利申请EP669323和专利US2463264中描述的;对氨基苯甲酸(PABA)衍生物;亚甲基双(羟基苯基苯并三唑)衍生物,例如在专利申请US5237071、US5166355、GB2303549、DE19726184和EP893119中描述的;防晒聚合物和防晒硅酮,特别地例如那些在专利申请WO93/04665中描述的;α-烷基-苯乙烯衍生的二聚物,例如那些在专利申请DE19855649中描述的。
矿物的光保护剂选自涂覆或未涂覆的金属氧化物颜料或纳米颜料(指的是原始颗粒的尺寸一般在5nm至100nm之间,优选10nm至50nm之间),例如二氧化钛(无定形或金红石型和/或锐钛型晶体)、氧化铁、氧化锌、氧化锆、氧化铈的纳米颜料,它们本身就是已知的UV保护剂。标准的涂覆剂还有矾土和/或硬脂酸铝。所述的涂覆或未涂覆的金属氧化物纳米颜料特别地在专利申请EP518772和EP518773中有所描述。
根据本发明,光保护剂在组合物中的一般用量范围为组合物总重量的0.1%-20%,优选为0.2%-15%。
具体实施方式
下列实施例举例说明了本发明,但并不限制其保护范围。根据情况,列举的化合物使用其化学名称或CTFA(国际化妆品原料字典和手册)名称。
实施例1:关于对黑素形成起作用的证明
生物实验证明了如(I)式所示的抗坏血酸酯衍生物的褪色活性。
根据专利申请EP-0993826的方法测定了(I)式所示的化合物对黑素形成的调节效果,R.Schmidt,P.Krien和M.Régnier的文章Anal.Biochem.,235(2),113-18,(1996)中也记载了该方法。
每个测试的化合物都进行了以下测定:
-细胞毒性,通过评估与亮氨酸的结合情况,
-对于黑色素合成的抑制活性,通过评估与硫脲嘧啶和与亮氨酸结合程度的比,相对于对比例的100%(对比例无测试化合物),
-IC50值,该值为观察到抑制50%黑素形成的微摩尔(μM)浓度。
结果整理于下表中:
IC50(μM) | 细胞毒性 | 测试浓度(μM) | 抑制黑素形成的活性 | |
化合物T1 | 无效果 | 无 | 312 | 无效果 |
化合物T2 | 无效果 | 无 | 327 | 无效果 |
化合物A | 200 | 无 | 230 | -50% |
化合物B | 500 | 无 | 262 | -60% |
化合物T1:抗坏血酸的甲基2,3-双-醋酸酯
化合物T2:抗坏血酸基2-肉桂酸酯
化合物A和化合物B如上所述。
由此,与其他测试的抗坏血酸酯相比,(I)式所示的化合物对于抑制黑素形成非常有效。
实施例2:关于对黑素细胞树突起作用的证明
该测试的目的是表明根据本发明使用的化合物在黑素细胞的形态学调节方面的效果。
方法:
用本发明的化合物直接接种作用于黑素细胞7天,化合物的用量为100μg每毫升。
观察:
黑素细胞用NK1beteb抗体标记(绿色),用以确定黑素体成熟的各个阶段。所有细胞、黑素细胞和角质细胞的细胞核用碘化丙炔染色(红色)。
结果:
·不存在本发明的化合物时,共同培养基中的黑素细胞树突化的程度很高。色素明显地转移到临近的角质细胞中。
·存在本发明的化合物时,大多数的黑素细胞表现出树突减少,并且一些黑素细胞形成双极。
·较高的浓度时,大多数黑素细胞形成双极,并且转移到角质细胞中的色素的量减少。
观察结果总结于下表:
测试化合物 | 测试浓度(μM) | 树突 | 色素的转移 |
对比例 | - | 多极 | 多 |
化合物T1 | 312 | 多极 | 多 |
化合物T2 | 327 | 多极 | 多 |
化合物A | 230 | 双极 | 少量色素被转移 |
化合物B | 262 | 双极 | 少量色素被转移 |
对于对比例,测试在没有本发明化合物的情况下进行。
化合物T1:抗坏血酸的甲基2,3-双-醋酸酯
化合物T2:抗坏血酸基2-肉桂酸酯
化合物A和化合物B如上所述。观察表明,对于这些化合物,与对比例和参照的化合物T1和T2相比,黑素细胞形成双极,并且处理后角质细胞中的色素的量减少了。
实施例3:
制备了一种水包油乳液型面部护理漂白霜,包括(以重量百分比计):
-5-(2,2-二甲基[1,3]二氧戊环-4-基)-4-羟基-2-氧代-2,5-二氢-3-呋喃基3-[(4-乙酸
基-3-甲氧基)苯基]丙烯酸酯 0.005%
-硬脂酸甘油酯 2%
-多乙氧基醚60(ICI的吐温60) 1%
-硬脂酸 1.4%
-三乙醇胺 0.7%
-carbomer 0.4%
-牛油树脂的液体部分 12%
-全氢化鲨烯 12%
-抗氧化剂 0.05%
-香精、防腐剂 适量
-水 补足至100%
实施例4:
制备了一种皮肤褪色凝胶,包括(以重量百分比计):
-5-(2,2-二甲基[1,3]二氧戊环-4-基)-4-羟基-2-氧代-2,5-二氢-3-呋喃基3-[(4-羟基-
3-甲氧基)苯基]丙烯酸酯 2%
-羟丙基纤维素(Hercules的Klucel H) 1%
-抗氧化剂 0.05%
-异丙醇 40%
-香精、防腐剂 适量
-水 补足至100%
Claims (9)
1.至少一种(I)式所示的化合物在美容组合物中作为皮肤和/或头发和/或其它毛发的漂白剂的美容用途:
其中,
R1和R4独立地表示氢原子或选自下列的基团:甲基、乙基、异丙基、阿魏基、苄基、三甲基甲硅烷基、三苯基甲硅烷基、叔丁基二甲基甲硅烷基、乙酰基、丙酰基、棕榈酰基、脂酰基、苯甲酰基,SO3H、O=P(OH)OH和CH3NHCO-,R2和R3独立地表示氢原子或选自下列的基团:甲基、乙基、异丙基、阿魏基、苄基、三甲基甲硅烷基、三苯基甲硅烷基、叔丁基二甲基甲硅烷基、乙酰基、丙酰基、棕榈酰基、脂酰基、苯甲酰基,SO3H、O=P(OH)OH和CH3NHCO-,或者R2和R3与其连接的氧一起形成5元环或6元环基团,R2和R3中至少有一个不为氢原子。
2.如权利要求1所述的至少一种(I)式所示的化合物的用途,其用于制备皮肤和/或头发和/或其它毛发褪色用皮肤学组合物。
3.权利要求1或2的用途,其特征在于R1表示氢原子。
4.权利要求1至3任意一项的用途,其特征在于R4表示氢原子或乙酰基。
5.权利要求1至4任意一项的用途,其特征在于R2和R3与其连接的氧原子一起形成异亚丙基。
6.权利要求1至5任意一项的用途,其特征在于(I)式所示的化合物为5-(2,2-二甲基[1,3]二氧戊环-4-基)-4-羟基-2-氧代-2,5-二氢-3-呋喃基3-[(4-乙酸基-3-甲氧基)苯基]丙烯酸酯。
7.权利要求1至5任意一项的用途,其特征在于如(I)式所示的化合物为5-(2,2-二甲基[1,3]二氧戊环-4-基)-4-羟基-2-氧代-2,5-二氢-3-呋喃基3-[(4-羟基-3-甲氧基)苯基]丙烯酸酯。
8.如权利要求1所述的至少一种(I)式所示的化合物在组合物中作为防晒剂的美容用途。
9.漂白人皮肤和/或头发和/或其它毛发的美容方法,包括将含有如权利要求1所述的至少一种(I)式所示化合物的美容组合物应用于皮肤和/或头发和/或其它毛发。
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FR02/16109 | 2002-12-18 | ||
FR0216109A FR2848846B1 (fr) | 2002-12-18 | 2002-12-18 | Utilisation cosmetique de derives de l'acide ascorbique comme agents blanchissants |
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JP (1) | JP2004285050A (zh) |
KR (1) | KR100580348B1 (zh) |
CN (1) | CN1235560C (zh) |
AT (1) | ATE308970T1 (zh) |
DE (1) | DE60302200T2 (zh) |
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FR (1) | FR2848846B1 (zh) |
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FR2892923B1 (fr) | 2005-11-08 | 2009-01-16 | Engelhard Lyon Sa | Utilisatiion des derives de l'acide para-coumarique ou para- hydroxycinnamique dans des compositions cosmetiques ou dermatologiques. |
FR2894961B1 (fr) * | 2005-12-16 | 2008-05-16 | Oreal | Utilisation de ceramides pour depigmenter la peau |
FR2902999B1 (fr) | 2006-07-03 | 2012-09-28 | Oreal | Utilisation de derives c-glycoside a titre d'actif prodesquamant |
FR2921254B1 (fr) * | 2007-09-21 | 2009-11-13 | Oreal | Utilisation en depigmentation d'une association d'acide jasmonique et d'acide ascorbique |
FR2971940B1 (fr) | 2011-02-28 | 2015-04-03 | Am Phyto Conseil | Extrait de rameaux d'hippophae et son utilisation dans une composition cosmetique |
US20230398047A1 (en) | 2021-05-14 | 2023-12-14 | L'oreal | Composition comprising skin care active ingredient and two polyglyceryl fatty acid esters |
WO2023068069A1 (en) | 2021-10-21 | 2023-04-27 | L'oreal | Composition comprising two polyglyceryl fatty acid esters and skincare active agent |
FR3131198A1 (fr) | 2021-12-27 | 2023-06-30 | L'oreal | Composition comprenant deux esters de polyglycéryle d’acide gras et un agent actif de soin de la peau |
WO2023249912A1 (en) * | 2022-06-21 | 2023-12-28 | L'oreal | Cosmetic composition comprising hydrophilic antioxidants and thiopyridinone compounds |
WO2023245459A1 (en) * | 2022-06-21 | 2023-12-28 | L'oreal | Anti-oxidizing composition comprising a thiopyridinone compound |
WO2024014310A1 (en) | 2022-07-12 | 2024-01-18 | L'oreal | Composition comprising skin care active ingredient or cellulose compound |
FR3138614A1 (fr) | 2022-08-05 | 2024-02-09 | L'oreal | Composition comprenant un ingrédient actif pour soin de la peau |
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JP3330961B2 (ja) * | 1991-02-22 | 2002-10-07 | 株式会社創研 | 皮膚改善剤 |
JP3122182B2 (ja) * | 1991-09-19 | 2001-01-09 | ホーユー株式会社 | 毛髪脱色剤 |
JP3195835B2 (ja) * | 1992-11-17 | 2001-08-06 | ポーラ化成工業株式会社 | メラニン産生抑制剤及び皮膚外用剤 |
FR2715156B1 (fr) * | 1994-01-20 | 1996-03-01 | Oreal | Mono-esters d'acide cinnamique ou de ses dérivés et de vitamine C, leur procédé de préparation et leur utilisation comme anti-oxydants dans des compositions cosmétiques, pharmaceutiques ou alimentaires. |
FR2725897B1 (fr) * | 1994-10-24 | 1996-12-06 | Oreal | Produit pour application topique contenant une lipase et un precurseur d'actif |
FR2738743B1 (fr) * | 1995-09-19 | 1997-11-14 | Oreal | Utilisation de l'acide ascorbique comme actif pour le traitement de la seborrhee dans une composition cosmetique et/ou dermatologique |
DE19638534A1 (de) * | 1996-09-20 | 1998-03-26 | Beiersdorf Ag | Verwendung von Tocopherylferulat zur Hautaufhellung oder zur Verhinderung der Hautbräunung, insbesondere der durch UV-Strahlung hervorgerufenen Hautbräunung |
FR2807320B1 (fr) * | 2000-04-10 | 2002-05-24 | Oreal | Utilisation de derives d'acide ascorbique pour augmenter la synthese des creramides epidermiques |
JP2002179516A (ja) * | 2000-12-13 | 2002-06-26 | Pola Chem Ind Inc | 美白用組成物 |
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- 2003-11-28 ES ES03292981T patent/ES2252636T3/es not_active Expired - Lifetime
- 2003-11-28 AT AT03292981T patent/ATE308970T1/de not_active IP Right Cessation
- 2003-12-16 KR KR1020030091919A patent/KR100580348B1/ko not_active IP Right Cessation
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FR2848846B1 (fr) | 2005-01-28 |
DE60302200D1 (de) | 2005-12-15 |
FR2848846A1 (fr) | 2004-06-25 |
KR100580348B1 (ko) | 2006-05-16 |
EP1430883A1 (fr) | 2004-06-23 |
ES2252636T3 (es) | 2006-05-16 |
DE60302200T2 (de) | 2006-08-03 |
ATE308970T1 (de) | 2005-11-15 |
CN1235560C (zh) | 2006-01-11 |
JP2004285050A (ja) | 2004-10-14 |
KR20040054515A (ko) | 2004-06-25 |
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