CN1205913C - 含有视黄醇和能够掩蔽uva辐射的化合物的组合物、特别是化妆品组合物 - Google Patents
含有视黄醇和能够掩蔽uva辐射的化合物的组合物、特别是化妆品组合物 Download PDFInfo
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- CN1205913C CN1205913C CNB01138512XA CN01138512A CN1205913C CN 1205913 C CN1205913 C CN 1205913C CN B01138512X A CNB01138512X A CN B01138512XA CN 01138512 A CN01138512 A CN 01138512A CN 1205913 C CN1205913 C CN 1205913C
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Abstract
本发明涉及含有药学上可接受的介质、视黄醇和能够掩蔽UVA辐射的相应于式(I)化合物的组合物。该化合物优选苯-1，4-二(3-亚甲基-10-樟脑磺酸)。本发明还涉及该组合物的应用，特别是用于预防或治疗内在的或光诱导的皮肤老化症状。本发明的组合物中，式(I)化合物具有掩蔽UVA辐射的作用，且不导致视磺醇的分解。
Description
发明领域
本发明的主题是新的化妆品和/或皮肤病用的组合物，特别是用于保护皮肤的组合物，包括药学上可接受的介质、视黄醇和能够掩蔽UVA辐射的化合物。
背景技术
近年来基于视色素的化妆品和/或皮肤病用的组合物由于其溶角蛋白剂作用已经经历了重大发展，特别是用于痤疮和皮肤病的治疗，以及用于预防和治疗内在的或光诱导的皮肤老化的某些症状，例如皱纹的形成和皮肤紧致性和弹性的降低。
在视色素族的衍生物中，也通称为维生素A的视黄醇具有很特别的优点。这是因为视黄醇是人体自然内生的成分，用于皮肤时可很好地被耐受，达到比视黄酸高得多的程度。
然而，当将视黄醇引入到局部应用的化妆品或皮肤病用的组合物中时，它将在光、氧气、金属离子、氧化剂或水的作用下，或特别是在温度升高的作用下迅速分解。在J.Soc.Cosm.Chem.，46，191-198(1995年7-8月)公开的研究主题即为视黄醇的热分解。
而且本申请人公司已经注意到将一些UVA掩蔽剂引入到含有视黄醇的化妆品组合物中，一段时间内将导致视黄醇的分解，并且不能清楚地鉴别出分解的原因。
这对于想用于预防和治疗光老化皮肤症状的组合物来说是特别不利的，至于在这些组合物中，将特别是在胶原合成方面的视黄醇的生物作用同吸收UVA辐射的防晒剂的作用结合通常是有利的。这是因为这些掩蔽剂有可能帮助细胞自身抵御过多的光诱导自由基和防止由于UVA的辐射而引起的胶原纤维的分解。这样它们就具有了同视黄醇的防老作用互补的抗老化作用。
因此认为得到含有视黄醇和紫外掩蔽剂、特别是UVA掩蔽剂的组合物、特别是化妆品组合物是重要的，在该组合物中视黄醇不被掩蔽剂分解。
发明概述
实际上，本申请人公司已经惊奇地发现可将所给出的一类UVA掩蔽剂引入含有视黄醇的组合物中而不导致后者的分解。这样，这些化妆品和/或皮肤病用组合物可保存数月，而其效果没有降低。
技术内容
因而本发明的主题是一种含有药学上可接受的介质、视黄醇和能够掩蔽UVA辐射的化合物的组合物，特征在于所述化合物相应于式(I)：
其中
-Z表示下式的基团：
-R2表示-H或-SO3H；
-n表示0或大于或等于1且小于或等于4的整数；
-R1表示一个或多个相同或不同的和直链或支链的含有1-4个碳原子的烷基或烷氧基，
-两个亚甲基樟脑基在苯环上彼此呈间位或对位。
任选地，式(I)化合物的磺酸官能团能全部或部分地被碱金属或碱土金属氢氧化物、铵或有机碱中和。
在专利US-4585597和专利申请FR2236515、2282426、2645148、2430938和2592380中分别公开上面的式(I)化合物。
特别优选的式(I)化合物是式(II)苯-1，4-二(3-亚甲基樟脑基-10-磺酸)：
或者，在本发明中使用时可以采用该化合物的一种碱金属、碱土金属或铵盐或者是该化合物的一种有机碱盐。
这是一种防晒物，能吸收波长为280-400nm、在320-400nm、特别是在345nm的附近有最大吸收的紫外线。
正如申请EP-0671160所表明的那样，当该化合物含有至少一个至少部分未被中和的磺酸官能团的时候，其具有防止皮肤内在老化的特性。
就较好预防紫外线辐射方面来说，除了上面提到的式(I)UVA掩蔽剂之外，本发明组合物还包括至少一种能掩蔽UVB辐射的化合物和/或至少另一种能掩蔽UVA辐射的化合物和/或至少一种任选包覆的无机颜料。
作为能够掩蔽UVB辐射的化合物可特别提及的是：
(1)水杨酸衍生物，特别是水杨酸高薄荷酯和水杨酸辛酯；
(2)肉桂酸衍生物，特别是对甲氧基肉桂酸2-乙基-己酯，来自Givaudan，商品名为Parsol MCX；
(3)液态β，β’-二苯基丙烯酸酯衍生物，特别是α-氰基-β，β’-二苯基丙烯酸2-乙基-己酯，或氰双苯丙烯酸辛酯(octocrylene)，来自BASF，商品名为Uvinul N539；
(4)对氨基苯甲酸衍生物；
(5)4-甲基苯亚甲基樟脑，来自Merck，商品名为Eusolex 6300；
(6)2-苯基苯并咪唑-5-磺酸，由Merck出售，商品名为“Eusolex232”；
(7)1，3，5-三嗪衍生物，特别是：
-2，4，6-三[4-(乙基己氧基羰基)苯氨基]-1，3，5-三嗪，来自BASF，商品名为Uvinul T150，和
-相应于下式的化合物：
其中R’表示2-乙基-己基和R表示叔丁基，来自Sigma 3V，商品名为Uvasorb HEB；
(8)它们的混合物。
作为其它的能够掩蔽UVA辐射的化合物可特别提及的是
(1)二苯酮衍生物，例如：
-2，4-二羟基二苯酮(二苯酮-1)；
-2，2’4，4’-四羟基二苯酮(二苯酮-2)；
-2-羟基-4-甲氧基二苯酮(二苯酮-3)，来自BASF，商品名为Uvinul M40；
-2-羟基4-甲氧基二苯酮-5-磺酸(二苯酮-4)及其磺酸酯的形式(二苯酮-5)，来自BASF，商品名为Uvinul MS40；
-2，2’-二羟基-4，4’-二甲氧基二苯酮(二苯酮-6)；
-5-氯-2-羟基二苯酮(二苯酮-7)；
-2，2’-二羟基-4-甲氧基二苯酮(二苯酮-8)；
-2，2’-二羟基-4，4’-二甲氧基二苯酮-5，5’-二磺二酸的二钠盐(二苯酮-9)；
-2-羟基-4-甲氧基-4’-甲基二苯酮(二苯酮-10)；
-二苯酮-11；
-2-羟基-4-(辛氧基)二苯酮(二苯酮-12)，
优选二苯酮-3和二苯酮-5；
(2)三嗪衍生物，特别是2，4-二[4-(2-乙基己氧基)-2-羟苯基]-6-(4-甲氧基苯基)-1，3，5-三嗪，来自Ciba-Geigy，商品名为Tinosorb S，以及2，2’-亚甲基二[6-(2H-苯并三唑-2-基)-4-(1，1，3，3-四甲基丁基)苯酚]，来自Ciba-Geigy，商品名为Tinosorb M；
(3)它们的混合物。
术语“任选包覆的无机颜料”具体可理解为表示包覆的或非包覆的金属氧化物纳米颜料(平均初级粒径：一般在5-100nm之间，优选在10-50nm之间)，例如二氧化钛(以金红石和/或锐钛矿形式的无定形或晶体)、氧化铁、氧化锌、二氧化锆或二氧化铈纳米颜料，其本身为熟知的紫外光防护剂。此外常规的涂敷剂是氧化铝和/或硬脂酸铝。在专利申请EP-A-0518772和EP-A-0518773中特别公开了这样的包覆的或非包覆的金属氧化物纳米颜料。
本发明的组合物优选倾向于化妆或皮肤病方面的应用，有利的是化妆用途。该组合物倾向于局部的应用，因此一般含有药物上可接受的介质，也就是与皮肤相适的介质。
本发明的组合物一般含有有效量的视黄醇以产生希望的效果，例如基于组合物总量的0.01-0.2重量％，优选0.01-0.15重量％。该组合物还含有足够量的式(I)UVA掩蔽剂以提供其所期望的防晒指数，例如基于组合物总量的0.5-5重量％、优选0.7-3重量％的式(I)UVA掩蔽剂。
该组合物可以任何一种在化妆和皮肤病领域中常用的药用剂型使用，特别是以任选被凝胶化的含水溶液、洗剂型分散体、任选具有两相通过脂肪相在含水相中分散(O/W)或相反地分散(W/O)所获得的乳液、三相乳液(W/O/W或O/W/O)或起泡的离子和/或非离子型分散体的形式。这些组合物按常规方法制备。优选本发明组合物是水包油乳液形式。
该组合物可以是或多或少呈液态、外观为白色或彩色的霜剂、软膏、乳液、洗液、清液、糊剂或泡沫。该组合物任选可以气溶胶形式用于皮肤。也可以提供固体的形式，特别是唇膏的形式。该组合物可作为皮肤的护理品和/或化妆品。
按照公知的方法，本发明组合物还可以含有化妆品领域中常规的调节剂，例如亲水的或亲油的胶凝剂、亲水的或亲油的活化成分、防腐剂、抗氧化剂、溶剂、香料、填料、颜料、气味吸收剂和着色材料。这些各种各样调节剂的量是在该领域的常规用量，例如组合物总量的0.01-20重量％。可将取决于其性质的这些调节剂加入脂肪相、含水相、脂囊泡和/或纳米颗粒中。无论怎样，选择的调节剂及其比例不应损害所期望的本发明组合物的特性。
当本发明组合物是乳液的时候，基于组合物总量的脂肪相的比例范围是5-80重量％，优选5-50重量％。以乳液的形式用于该组合物中的油、乳化剂和辅助乳化剂选自该领域中常用的那些。该组合物中存在的乳化剂和辅助乳化剂比例范围为基于组合物总量的0.3-30重量％，优选0.5-20重量％。
作为本发明所使用的油类，可以提及的是矿物油(液态凡士林)、植物油(鳄梨油、豆油)、动物油(羊毛脂)、合成油(全氢化角鲨烯)、硅油(环甲基硅酮)和氟化油(全氟化聚醚)。也可以使用脂肪醇(十六醇)、十六酸或蜡类(巴西棕榈蜡、地蜡)作为脂肪物质。
作为用于本发明的乳化剂和辅助乳化剂，可以提及的是例如诸如PEG-100硬脂酸酯的聚酯肪酸乙二醇酯和诸如甘油硬脂酸酯的甘油脂肪酸酯。
作为亲水胶凝剂，可以提及的是羧基乙烯基聚合物(carbomer)，丙烯酸系共聚物，如丙烯酸酯/烷基丙烯酸酯共聚物，聚丙烯酰胺，聚糖类，天然树胶和粘土；作为亲油胶凝剂，可以提及的是改性粘土，如膨润土，脂肪酸金属盐，亲水二氧化硅和聚乙烯。
本发明还涉及上述组合物作为化妆品的应用，特别是用于预防或治疗内在的或光诱导的皮肤老化症状。
最佳实施方案
依据下面的实施例将较好地理解本发明，更加清楚地突出本发明的优点，下面给出的实施例是对本发明的解释，并不限制本发明。
实施例
实施例1：化妆品组合物
A相
甘油硬脂酸酯和PEG-100硬脂酸酯 2.1％
Polysorbate 60 0.9％
十六醇 2.6％
氢化的聚异丁烯 12％
己基癸醇 8％
BHT 0.1％
防腐剂 0.15％
B相
水 适量的直到100％
甘油 3％
防腐剂 0.55％
乙二胺四亚甲基膦酸的五钠盐 0.07％
C相
黄原酸胶 0.1％
Carbomer 0.4％
D相
水 5％
三乙醇胺 0.38％
E相
苯-1，4-二(3-亚甲基-10-樟脑-磺酸) 1％
三乙醇胺 0.19％
F相
视黄醇 0.1％
以下述方式制备上面的组合物。
将A和B相在75℃各自加热搅拌直到完全溶解。在室温下分别搅拌来制备D和E相。随后在75℃、搅拌下、在5-10分钟的范围内将A相滗析入B相，然后将合并的混合物冷却到50℃。随后在50℃搅拌下将C相的组分引入A和B相的混合物中，在完全均化之后，搅拌下连续地加入D和E相。将混合物冷却到室温。在用氮气惰性化之后，搅拌下将F相引入容器中。
该组合物可作为日霜每天使用，以预防和防止皱纹和调理皮肤。
实施例2：视黄醇稳定性的证明
以下面的三种组合物A-C来评价视黄醇的稳定性：
组合物A：没有E相的实施例1组合物
组合物B：实施例1的组合物
组合物C：没有E相以及在A相中具有1％的4-叔丁基-4’-甲氧基二苯甲酰基甲烷(Givaudan出售的名为Parsol 1789)的实施例1的组合物。
测定视黄醇分别存在于上面的组合物A-C中的重量，首先是在室温下，在这些组合物的制备之后立即进行测量(To)，其次是在45℃储藏二个月之后进行测量(T2m)。
用高压液相色谱进行测量，使用标准的在四氢呋喃中的16μg/ml的视黄醇溶液，该溶液是由来自BASF出售的Retinol 10S样品以10％视黄醇油溶液的方式来制备的。
得到的结果如下：
| To | T2m | |
| 组合物A | 0.108％ | 0.102％ |
| 组合物B | 0.108％ | 0.097％ |
| 组合物C | 0.105％ | 0.071％ |
考虑到所使用的定量测量方法的精确性，从此可以推出含有苯-1，4-二(3-甲基亚基-10-樟脑磺酸)作为UVA掩蔽剂的组合物B与不含有UV掩蔽剂的组合物A一样稳定，而明显地比含有另一种UVA掩蔽剂的组合物C更稳定。
Claims (12)
1.一种组合物，其包括药学上可接受的介质、基于组合物的总重量，0.01-0.2重量％视黄醇和0.5-5重量％能够掩蔽UVA辐射的化合物，特征在于所述化合物相应于式(I)：
其中
—Z表示下式的基团：
—R2表不-H或-SO3H；
—n表示0或大于或等于1且小于或等于4的整数；
—R1表示一个或多个相同或不同的和直链或支链的含有1-4个碳原子的烷基或烷氧基，
—两个亚甲基樟脑基在苯环上彼此形成间位或对位，式(I)化合物的磺酸官能团全部或部分地被碱金属或碱土金属氢氧化物、氨或有机碱中和或未被中和。
2.权利要求1的组合物，特征在于式(I)化合物是苯-1，4-二(3-亚甲基-10-樟脑磺酸)或是该化合物的碱金属、碱土金属或铵盐中的一种或者是该化合物与有机碱所成盐中的一种。
3.权利要求1的组合物，特征在于该组合物含有基于组合物总量的0.01-0.15重量％的视黄醇。
4.权利要求1-3任何一项的组合物，特征在于该组合物含有基于组合物总量的0.7-3重量％的式(I)化合物。
5.权利要求1-3任何一项的组合物，特征在于该组合物是水包油乳液的形式。
6.权利要求1-3任何一项的组合物，特征在于该组合物还含有至少一种能掩蔽UVB辐射的化合物和/或至少另一种能掩蔽UVA辐射的化合物和/或至少一种包覆或未包覆的无机颜料。
7.权利要求6的组合物，特征在于能够掩蔽UVB辐射的所述化合物选自：
(1)水杨酸衍生物，
(2)肉桂酸衍生物
(3)液态β，β’-二苯基丙烯酸酯衍生物
(4)对氨基苯甲酸衍生物；
(5)4-甲基苯亚甲基樟脑；
(6)2-苯基苯并咪唑-5-磺酸；
(7)1，3，5-三嗪衍生物
(8)它们的混合物。
8.权利要求6的组合物，特征在于能够掩蔽UVB辐射的所述化合物选自：
(1)水杨酸高薄荷酯和水杨酸辛酯，
(2)2-乙基己基-对甲氧基肉桂酸酯，
(3)2-乙基己基-α-氰基-β，β’-二苯基丙烯酸酯，或氰双苯丙烯酸辛酯，
(4)4-甲基苯亚甲基樟脑，
(5)2-苯基苯并咪唑-5-磺酸，
(6)2，4，6-三[4-(乙基己基氧羰基)苯氨基]-1，3，5-三嗪
(7)相应于下式的化合物：
其中R’表示2-乙基己基和R表示叔丁基。
9.权利要求6的组合物，特征在于能够掩蔽UVA辐射的所述另一种化合物选自：
(1)二苯酮衍生物，
(2)三嗪衍生物，和
(3)它们的混合物。
10.权利要求7-9任何一项的组合物，特征在于能够掩蔽UVA辐射的所述其它化合物选自：
(1)2-羟基-4-甲氧基二苯酮(二苯酮-3)和2-羟基4-甲氧基二苯酮-5-磺酸，和，
(2)2，4-二[4-(2-乙基己氧基)-2-羟苯基]-6-(4-甲氧基苯基)-1，3，5-三嗪和2，2’-亚甲基二[6-(2H-苯并三唑-2-基)-4-(1，1，3，3-四甲基丁基)苯酚]。
11.权利要求6的组合物，特征在于所述无机颜料选自二氧化钛、氧化铁、氧化锌、二氧化锆或二氧化铈纳米颜料，用氧化铝和/或硬脂酸铝包覆或未包覆。
12.权利要求1-11任何一项组合物在制备用于预防或治疗内在的或光诱导的皮肤老化症状的化妆品中的应用。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0013285A FR2815252B1 (fr) | 2000-10-17 | 2000-10-17 | Composition, notamment cosmetique, renfermant du retinol et un compose capable de filtrer le rayonnement uva |
| FR00/13285 | 2000-10-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1368044A CN1368044A (zh) | 2002-09-11 |
| CN1205913C true CN1205913C (zh) | 2005-06-15 |
Family
ID=8855434
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB01138512XA Expired - Fee Related CN1205913C (zh) | 2000-10-17 | 2001-10-16 | 含有视黄醇和能够掩蔽uva辐射的化合物的组合物、特别是化妆品组合物 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US20020137795A1 (zh) |
| EP (1) | EP1199066B1 (zh) |
| JP (1) | JP2002167320A (zh) |
| CN (1) | CN1205913C (zh) |
| AT (1) | ATE271851T1 (zh) |
| DE (1) | DE60104504T2 (zh) |
| ES (1) | ES2223752T3 (zh) |
| FR (1) | FR2815252B1 (zh) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10229997A1 (de) * | 2002-07-03 | 2004-01-15 | Beiersdorf Ag | Kosmetische oder dermatologische Zubereitung zum Schutz fotolabiler Wirkstoffe |
| DE10247357A1 (de) * | 2002-10-10 | 2004-04-22 | Beiersdorf Ag | Fettfreie Sonnenschutzmittel |
| DE10328547A1 (de) * | 2003-06-24 | 2005-01-13 | Basf Ag | Mischung bestehend aus einem UV-A- und einem UV-B-Filter |
| US20120156146A1 (en) * | 2010-11-19 | 2012-06-21 | Tomohiro Hakozaki | Compositions and Methods for Improving the Appearance of Facial Texture |
| CA2817729C (en) * | 2010-11-19 | 2016-05-10 | The Procter & Gamble Company | Compositions and methods for improving the appearance of facial pores |
| US11534381B2 (en) | 2020-06-30 | 2022-12-27 | L'oreal | Cosmetic composition for improved penetration |
| US11865197B2 (en) | 2020-06-30 | 2024-01-09 | L'oreal | Cosmetic compositions having stabilized retinol |
| US11819560B2 (en) | 2020-08-31 | 2023-11-21 | L'oreal | Cosmetic compositions, kits thereof, and methods for making and using the same |
| US12083207B2 (en) | 2020-08-31 | 2024-09-10 | L'oreal | Cosmetic compositions, kits thereof, and methods for making and using the same |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2642968B1 (fr) * | 1989-02-15 | 1991-06-07 | Oreal | Utilisation en cosmetique de diorganopolysiloxanes a fonction benzotriazole et nouvelles compositions cosmetiques contenant ces composes, destinees a la protection de la peau et des cheveux |
| FR2695560B1 (fr) * | 1992-09-17 | 1994-11-04 | Oreal | Composition cosmétique filtrante photostable contenant un filtre UV-A et un polymère filtre du type silicone benzotriazole. |
| 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. |
| FR2717078B1 (fr) * | 1994-03-08 | 1996-12-13 | Oreal | Utilisation des acides sulfoniques comme agents antivieillissement dans une composition cosmétique ou dermatologique. |
| TWI234467B (en) * | 1997-06-04 | 2005-06-21 | Univ Michigan | Composition for inhibiting photoaging of skin |
| FR2779060B1 (fr) * | 1998-05-26 | 2003-05-02 | Oreal | Association d'un retinoide avec un derive d'histidine |
-
2000
- 2000-10-17 FR FR0013285A patent/FR2815252B1/fr not_active Expired - Fee Related
-
2001
- 2001-10-03 ES ES01402552T patent/ES2223752T3/es not_active Expired - Lifetime
- 2001-10-03 AT AT01402552T patent/ATE271851T1/de not_active IP Right Cessation
- 2001-10-03 EP EP01402552A patent/EP1199066B1/fr not_active Expired - Lifetime
- 2001-10-03 DE DE60104504T patent/DE60104504T2/de not_active Expired - Fee Related
- 2001-10-16 CN CNB01138512XA patent/CN1205913C/zh not_active Expired - Fee Related
- 2001-10-16 JP JP2001318624A patent/JP2002167320A/ja active Pending
- 2001-10-17 US US09/978,027 patent/US20020137795A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| FR2815252B1 (fr) | 2002-12-20 |
| FR2815252A1 (fr) | 2002-04-19 |
| ES2223752T3 (es) | 2005-03-01 |
| JP2002167320A (ja) | 2002-06-11 |
| EP1199066B1 (fr) | 2004-07-28 |
| DE60104504T2 (de) | 2005-09-01 |
| DE60104504D1 (de) | 2004-09-02 |
| CN1368044A (zh) | 2002-09-11 |
| US20020137795A1 (en) | 2002-09-26 |
| EP1199066A1 (fr) | 2002-04-24 |
| ATE271851T1 (de) | 2004-08-15 |
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