CN1117737C - 对称三嗪衍生物 - Google Patents
对称三嗪衍生物 Download PDFInfo
- Publication number
- CN1117737C CN1117737C CN97199778A CN97199778A CN1117737C CN 1117737 C CN1117737 C CN 1117737C CN 97199778 A CN97199778 A CN 97199778A CN 97199778 A CN97199778 A CN 97199778A CN 1117737 C CN1117737 C CN 1117737C
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- China
- Prior art keywords
- hair
- formula
- glue
- usefulness
- washing lotion
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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Abstract
本发明描述了式(1)的对称三嗪衍生物,式中R1和R2各分别为氢;C1-C12烷基,C1-C12烷氧基;和R3是C1-C12烷基或C1-C12烷氧基。易于获得的所述三嗪衍生物适用于保护紫外线敏感物质特别是人类和动物的皮肤和毛发免受紫外辐射的有害影响。
Description
技术领域
本发明涉及对称三嗪衍生物,涉及这些化合物的制备以及涉及其保护有机材料免受紫外辐射的有害影响的用途。
背景技术
含有至少一个邻位羟基或至少两个烷氧基苯基取代基的邻位烷基化邻羟苯基三嗪(HPT)是例如从EP-A-0,743,309已知的,作为具有良好的光谱性质和良好的工业应用性能的化妆品紫外线吸收剂。但是,这类源于下列不对称基本结构:的三嗪衍生物的制备需要用多步骤合成方法。在上式中,Ra和Rb是一个反应基,具体是一个被羟基单取代或多取代的苯基。
可从下列对称基本结构制备的对称三嗪化合物:更易于通过简单的一浴(one-bach)法合成。
这种“三嗪基本结构”可例如通过相应的苄腈化合物的三聚或使用氰尿酰氯为原料,通过格利雅反应或弗瑞德-克来福特烷基化来制备。游离OH基的随后醚化使得可以制备可用两步反应制备的所需的三嗪衍生物。
发明内容
因此,本发明涉及下式的对称三嗪衍生物:
式中
R1和R2各分别代表氢;C1-C12烷基;或C1-C12烷氧基;和R3是C1-C12烷基或C1-C12烷氧基。
C1-C12烷基或C1-C12烷氧基是直链或支链烷基,典型的有甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基、戊基、异戊基或叔戊基、庚基、辛基、异辛基、壬基、癸基、十一基或十二基、或甲氧基、乙氧基、丙氧基、丁氧基、戊氧基、己氧基、庚氧基、辛氧基、壬氧基、癸氧基、十一烷氧基或十二烷氧基。
特别优选的化合物是那些式(1)的化合物,式中
R3是C1-C12烷氧基,特别是C5-C12烷氧基;和
R1和R2具有式(1)中所给的意义。
式中
R4和R5各分别代表氢;C1-C12烷基;或C1-C12烷氧基;和R6是C1-C12烷基或C1-C12烷氧基。
重要的化合物具体是那些式(2)的化合物,其中
R4是氢;和
R5和R6是C5-C12烷氧基;
或者是那些式(2)的化合物,其中
R4和R5是C5-C12烷基;和
R6是氢。
式中
R7是C5-C12烷氧基;和
C8是氢或C1-C5烷基。
本发明的三嗪衍生物可以单个化合物形式使用或者以相互不同的单个化合物的混合物形式使用。
在式(4)中
R10为氢;C6-C12烷基或C2-C6链烯基;和
R11是C1-C12烷氧基。
C2-C6链烯基是例如烯丙基、甲基烯丙基、异丙烯基、2-丁烯基、3-丁烯基、异丁烯基、正戊-2,4-二烯基或3-甲基-丁-2-烯基。
式(1)和式(4)三嗪化合物的混合物是本发明的另一要点。
式(1)的新的三嗪衍生物可用不同方式制备。例如在格利雅反应中,1摩尔氰尿酰氯与3摩尔相应的溴化苯基镁化合物(其根据式(1)的R1、R2和R3的意义,可包含一个烷基和/或一个或几个游离羟基)反应。制备这种中间体的方法是已知的并且特别说明于EP-A-0,557,559中。
这种中间体也可通过在路易斯酸(优选氯化铝)的存在下,使氰尿酰氯与相应的苯基化合物(其根据式(1)的R1、R2和R3的意义,可包含一个烷基和/或一个或几个游离羟基)弗瑞德-克来福特烷基化来获得。
按照A.Ninagawa,M.Kawanoe,H.Matsuada,Makromol.Chem.180,(1979),2123,这种中间体也可通过一种苄腈化合物(其根据式(1)的R1、R2和R3的意义,含一个烷基和/或一个或多个羟基)的环三聚获得。
可在第二个反应步骤中,通过按照常规方法烷基化,将在第一步骤中获得的中间体的羟基醚化,获得相应于式(1)的终产物。
本发明的再一个要点涉及所述新的三嗪衍生物的制备方法。
本发明的式(1)的对称三嗪衍生物或者这些化合物与式(4)三嗪化合物的混合物以及下式的化合物:
式中
Ar是一个下式的基团:
R1是氢;羟基;C1-C12烷基;或C1-C12烷氧基;
R2是羟基;C1-C12烷氧基;或苄氧基;
R3是羟基;C1-C12烷基;或C1-C12烷氧基;和
R4是氢;或C1-C12烷氧基;或
R1和R2与所述苯基一起是一个与苯稠合的杂环五员环,优选式(5)的一个基团:特别适合作为紫外线(UV)滤除剂,即用于保护紫外线敏感的有机物质,特别是用于保护人类和动物的皮肤和毛发免受紫外辐射的有害影响。
因此,这些化合物适合于在化妆品、药用和兽用制品中作为光稳定剂。它们可以溶解形式获得,或者如果它们只微溶或不溶,那么可以平均粒径0.02-2、优选0.05-1.5和最优选0.1-1.0μm的微粒形式混入到制剂中。
因此,本发明的另一个目标是提供用于皮肤和毛发的化妆品制剂,它包括至少一种式(1)或(5)的化合物以及用于化妆品上适合于皮肤和毛发的载体和辅剂,或者是提供一种用于皮肤和毛发的化妆品制剂,它包括一种下列物质的混合物:
a)至少一种或一种以上的式(1)或(5)的化合物,和
b)一种式(4)的化合物以及化妆品学上适合于皮肤和毛发的载体和辅剂。
除了所述新的UV吸收剂外,所述化妆品制剂也可包含一种或多种下列UV防护物质:
1.对氨基苯甲酸衍生物,典型有4-二甲基氨基苯甲酸2-乙基己酯;
2.水杨酸衍生物,典型有水杨酸2-乙基己酯;
3.二苯酮衍生物,典型有2-羟基-4-甲氧基二苯酮和其5-磺酸衍生物;
4.二苯甲酰基甲烷衍生物,典型有1-(4-叔丁基苯基)-3-(4-甲氧基苯基)-丙烷-1,3-二酮;
5.二苯基丙烯酸酯,典型有2-乙基己基-2-氰基-3,3-二苯基丙烯酸酯和3-(苯并呋喃基)-2-氰基丙烯酸酯;
6.3-咪唑-4-基-丙烯酸和3-咪唑-4-基丙烯酸酯;
7.苯并呋喃衍生物,优选公开于EP-A-582,189、US-A-5,338,539、US-A-5,518,713和EP-A-613,893中的2-(对氨基苯基)苯并呋喃衍生物;
8.聚合的UV吸收剂,诸如特别描述于EPA-709,080中的丙二酸二苄酯衍生物;
9.肉桂酸衍生物,典型有2-乙基己醇的4-甲氧基肉桂酸酯或异戊酸酯或特别公开于US-A-5,601,811和WO97/00851中的肉桂酸衍生物;
10.樟脑衍生物,典型有3-(4'-甲基)亚苄基莰-2-酮、3-亚苄基莰-2-酮、N-[2(和4)-2-氧基亚莰-3-基甲基)苄基]丙烯酰胺聚合物、3-(4’-三甲基铵)亚苄基莰2-酮甲基硫酸酯、3,3’-(1,4-苯二次甲基)-双(7,7-二甲基-2-氧代-双环-[2.2.1]庚烷-1-甲磺酸)和其盐、3-(4’-磺基)亚苄基莰-2-酮和其盐;
11.三苯胺基-s-三嗪衍生物,典型有2,4,6-三苯胺-(对羰基-2’-乙基-1’-氧基(oxi))-1,3,5-三嗪以及公开于US-A-5,332,568、EP-A-517,104、EP-A-507,691、WO93/17002和EP-A-570,838中的UV吸收剂;
12.2-羟基苯基苯并三唑衍生物;
13.2-苯基苯并咪唑5-磺酸和其盐;
14.对氨基苯甲酸酯;
15.TiO2(不同涂层)、ZnO和云母。
在“Sunscreens”,Eds.N.J.Lowe,N.A.Shaath,Marcel Dekker,Inc.,New York and Basel或在Cosmetics & Toiletries(107),50et seq.(1992)中所述的UV吸收剂也可在本发明的制剂中用作另外的UV保护剂。
所述化妆品制剂也可与已知的抗氧化剂诸如维生素E、类胡萝卜素或HALS化合物一起使用。
所述新的化妆品制剂通常包括基于制剂总重量0.1-25%、优选0.5-10%(重量)的式(1)或(5)的UV吸收剂或式(1)和(4)的UV吸收剂的混合物以及化妆品学上适用的辅剂。
所述化妆品制剂可通过用常规方法(诸如将各组分一起搅拌)物理混合所述UV吸收剂和辅剂来制备。
本发明的化妆品制剂可制成油包水或水包油乳液、醇包油洗液、离子或非离子两亲脂质的多泡分散体(vesicular dispersion)、胶、固体棒(solid stick)或气溶胶制剂。
作为油包水或水包油乳液,所述化妆品学上适用的辅剂优选包括5-50%的油相、5-20%的乳化剂和30-90%的水。所述油相可包含任何适用于化妆品制剂的油例如一种或几种烃油、蜡、天然油、硅油、脂肪酸酯或脂肪醇。优选的一元醇或多元醇是乙醇、异丙醇、丙二醇、己二醇、甘油和山梨醇。
用于毛发的化妆品制剂的可以下列形式使用:
以调理(rinsing)用的洗发液、洗液、胶或乳液形式(在洗发前或后、染色或脱染前或后、烫发或拉直处理前或后使用);
以定型或护理(treating)用的洗液、泡沫剂或胶形式;
以梳理(brushing)或卷发用的洗液和胶形式;
以发蜡的形式;
以用于烫发或直发的组合物、用于染色和脱染的组合物的形式。
可以使用例如下列用于毛发的化妆品制剂:
a1)充入水和任何季铵化合物(诸如4%氯化貂酰胺基(minkalmido)丙基二甲基-2-羟乙基铵或Quaternium 80)且包括所述UV吸收剂、PEG-6 C10羰基合成醇和脱水山梨糖醇esquioleate的自发乳化贮备制剂;
a2)充入水和任何季铵化合物(诸如4%氯化貂酰胺基丙基二甲基-2-羟乙基铵或Quaternium 80)且包括所述UV吸收剂、柠檬酸三丁酯、PEG-20脱水山梨糖醇单油酸酯的自发乳化贮备制剂;
b)所述UV吸收剂在丁基三甘醇和柠檬酸三丁酯中的掺有季铵化合物(quat)的溶液。
c)在水性制剂中的通过已知方法(从溶液或溶液的混合物沉淀,研磨)获得的微粒化UV吸收剂[在APG(如Plantaren)和一种季铵化合物(quat)(如貂酰胺基丙基二甲基-2-羟乙基铵)中的平均粒径为0.05-1.0微米]的分散体;
d)所述UV吸收剂和正烷基吡咯烷酮的混合物或溶液。
所述用于皮肤或毛发的化妆品制剂也可包含其它组分,诸如润肤剂、乳液稳定剂、皮肤湿润剂、晒黑促进剂、增稠剂诸如黄原胶、保湿剂诸如甘油、防腐剂、香料和着色剂。
所述用于皮肤和毛发的新的化妆品制剂具有出色的保护人类皮肤和毛发免受阳光的有害影响的特征。
具体实施方式
在100-105℃,将5.36g式(101a)的化合物溶解于50ml二甲基甲酰胺(DMF)中,并加入6.53g细粉状碳酸钾。将混合物在100-105℃搅拌30分钟后,再用30分钟时间滴加8.23g溶解于10ml DMF中的3-(氯甲基)庚烷。用6小时将温度缓慢升到135℃。冷却到100℃后,加入50ml甲苯并且过滤去除沉淀的盐。将滤液蒸发浓缩到干,并且残留物用50ml甲苯和100ml水溶解、经酸化后摇晃萃取。经干燥的有机相通过蒸发浓缩。粗产物(约7g)通过柱层析(硅胶,环己烷/甲苯7∶3)纯化。
式(102a)的基本结构通过例如在弗瑞德-克来福特条件下2,6-二甲基苯酚与氰尿酰氯的反应(参见DE-A-2,219,012)获得。
在100-105℃将6.62g式(102a)的化合物溶解于70ml二甲基甲酰胺(DMF)中,并加入6.53g细粉状碳酸钾。将混合物在100-105℃搅拌30分钟后,再用60分钟时间滴加11.65g溶解于10mlDMF中的3-(氯甲基)庚烷。将温度保持在100-105℃3小时。冷却到100℃后,加入50ml甲苯并且过滤去除沉淀的盐。将滤液蒸发浓缩到干,并且向残留物加入50ml甲苯和100ml水溶解、经酸化后摇晃萃取。有机层用水洗至中性,经分离和干燥后通过蒸发浓缩。粗产物(约10g)通过柱层析(硅胶,环己烷/甲苯65∶35)纯化。
收率:4.7g无色结晶,熔点83-84℃,(理论值的40%)。实施例3:
式(103)的化合物:可按一般类似实施例1的步骤制备。应用实施例: 实施例4:一种油/水乳液的制备配方(按照CTFA或INCI命名):
(a1)ceteareth6(和)十八烷醇 2.0%
(a2)ceteareth25 2.0%
(a3)cetearyl醇 5.0%
(a4)辛酸/癸酸三甘油酯 5.0%
(a5)cetearyl辛酸酯 10.0%
(a6)凡士林 5.0%
(a7)式(101)的化合物 4.0%
(b1)丙二醇 3.0%
(b2)carbopol 934 0.2%
(b3)H2O 63.53%
(c)三乙醇胺 0.27%
将组分(a1)-(a7)(=相A)和(b1)-(b3)(=相B)加热到75-80℃。然后将相B加到相A并均化。然后加入组分(c)并再均化。
使用一台SPF(防晒因子)分析仪(Optometrix,SPF290),通过Diffey and Robson,J.Soc.Cosmet.Chem.
40,127-133(1989)的方法测定防晒因子。
这种油/水乳液的防晒因子为7.8。
实施例5:晒黑膏的制备:
配方(各组分按照CTFA或INCI命名):
相A:
(a1)dimethicone 2.0%
(a2)肉豆蔻酸异丙酯 9.0%
(a3)十八烷醇 10.0%
(a4)硬脂酸 4.0%
(a5)式(102)的化合物 4.0%
(a6)微粒化的2,4-二(苯基)-6-(2-羟基-4-
甲氧基苯基)-1,3,5-三嗪(φ0.25μm) 3.2%
(b1)三乙醇胺 1.2%
(b2)carbomer 934 5.0%
(b3)H2O 61.6%
单独和非常小心地将组分(a1-a6)(=相A)均化,然后象组分(b1)-(b3)(=相B)那样单独加热到75-80℃。然后在剧烈搅拌下将相B加入到相A。在搅拌下让混合物冷却。
这种晒黑膏的防晒因子为11。
Claims (10)
3.根据权利要求1式(2)的对称三嗪衍生物的用途,用于保护人类毛发和皮肤免受紫外线的不良影响。
4.一种用于皮肤和毛发的化妆品制剂,其中包括与化妆品学上适合于毛发和皮肤的载体和辅剂一起的至少一种或一种以上式(2)的化合物。
5.一种用于皮肤和毛发的化妆品制剂,其中包括与化妆品学上适合于皮肤和毛发的载体和辅剂一起的一种下列物质的混合物:
a)至少一种式(2)的化合物,和
b)一种式(4)的化合物。
6.一种根据权利要求4或5的用于皮肤和毛发的化妆品制剂,其包括基于制剂总重量0.1-25%重量的式(2)UV吸收剂或式(2)和(4)的UV吸收剂的混合物以及至少一种适用于皮肤和毛发的辅剂。
7.用于保护头发免受紫外辐射损害的按照权利要求4的毛发化妆品制剂的用途,在洗发前或后、染色或脱除染料前或后、烫发或拉直处理前或后,以调理用的洗发液、洗液、胶或乳液形式;以定形或护发用的洗液、泡沫剂或胶形式;以梳理或卷发用的洗液和胶形式;以发蜡的形式;以用于烫发或直发的组合物、用于染色和脱染的组合物的形式获得。
8.用于保护头发免受紫外辐射损害的按照权利要求5的毛发化妆品制剂的用途,在洗发前或后、染色或脱除染料前或后、烫发或拉直处理前或后,以调理用的洗发液、洗液、胶或乳液形式;以定形或护发用的洗液、泡沫剂或胶形式;以梳理或卷发用的洗液和胶形式;以发蜡的形式;以用于烫发或直发的组合物、用于染色和脱染的组合物的形式获得。
9.用于保护头发免受紫外辐射损害的按照权利要求6的毛发化妆品制剂的用途,在洗发前或后、染色或脱除染料前或后、烫发或拉直处理前或后,以调理用的洗发液、洗液、胶或乳液形式;以定形或护发用的洗液、泡沫剂或胶形式;以梳理或卷发用的洗液和胶形式;以发蜡的形式;以用于烫发或直发的组合物、用于染色和脱染的组合物的形式获得。
10.保护人发免受紫外辐射的有害影响的非治病的处理方法,其中包括将头发用下列制剂处理:在洗发前或后、染色或脱除染料前或后、烫发或拉直处理前或后使用调理用的洗发液、洗液、胶或乳液,定形用的洗液、泡沫剂或胶,梳理或卷发用的洗液和胶,发蜡,用于烫发或直发的组合物、用于染色和脱染的组合物;所述洗发液、洗液、胶、乳液、泡沫剂、发蜡或用于烫发、直发、染发或脱染的组合物包含至少一种式(2)的紫外线吸收剂或式(2)和式(4)紫外线吸收剂的混合物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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CH2865/1996 | 1996-11-20 | ||
CH2865/96 | 1996-11-20 | ||
CH286596 | 1996-11-20 |
Publications (2)
Publication Number | Publication Date |
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CN1237966A CN1237966A (zh) | 1999-12-08 |
CN1117737C true CN1117737C (zh) | 2003-08-13 |
Family
ID=4243329
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CN97199778A Expired - Fee Related CN1117737C (zh) | 1996-11-20 | 1997-11-10 | 对称三嗪衍生物 |
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US (1) | US6217856B1 (zh) |
EP (1) | EP0941217B1 (zh) |
JP (1) | JP4252627B2 (zh) |
KR (1) | KR100514940B1 (zh) |
CN (1) | CN1117737C (zh) |
AT (1) | ATE250040T1 (zh) |
AU (1) | AU736424B2 (zh) |
BR (1) | BR9713109B1 (zh) |
DE (1) | DE69724992T2 (zh) |
ES (1) | ES2205268T3 (zh) |
ID (1) | ID21704A (zh) |
IL (1) | IL129644A0 (zh) |
RU (1) | RU2191178C2 (zh) |
WO (1) | WO1998022447A1 (zh) |
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FR2789580A1 (fr) * | 1999-02-12 | 2000-08-18 | Oreal | Compositions cosmetiques antisolaires a base d'un melange synergique de filtres et utilisations |
FR2789581B1 (fr) | 1999-02-12 | 2001-05-04 | Oreal | Compositions photoprotectrices contenant un derive de benzotriazole, un derive de bis-resorcinyl triazine et un compose a groupements benzoazolyle ou benzodiazolyle |
FR2789583B1 (fr) * | 1999-02-12 | 2002-02-01 | Oreal | Compositions cosmetiques antisolaires a base d'un melange synergique de filtres et utilisations |
EP1068866A3 (de) | 1999-07-12 | 2004-03-17 | Ciba SC Holding AG | Verwendung von Mischungen aus Mikropigmenten zur Bräunungsverhinderung und Aufhellung der Haut und Haare |
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FR2833164B1 (fr) | 2001-12-07 | 2004-07-16 | Oreal | Compositions cosmetiques antisolaires a base d'un melange synergique de filtres et utilisations |
EP1371355B1 (en) | 2002-06-03 | 2006-08-02 | Ciba SC Holding AG | UV-protection formulations |
MXPA05002191A (es) | 2002-08-30 | 2005-06-08 | Ciba Sc Holding Ag | Pigmentos brillantes coloreadas que tienen al menos un revestimiento de siox, con x= 0.03 a 0.95 para el u so en formulaciones cosmeticas y de cuidado personal. |
BRPI0406835A (pt) * | 2003-01-20 | 2005-12-27 | Ciba Sc Holding Ag | Derivados de triazina como absorvedores de uv |
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JP4764817B2 (ja) * | 2003-03-24 | 2011-09-07 | チバ ホールディング インコーポレーテッド | 対称性トリアジン誘導体 |
EP1648400A1 (en) * | 2003-07-16 | 2006-04-26 | Ciba SC Holding AG | Use of halogenated hydroxydiphenyl ether compounds for the treatment of the skin |
JP5204766B2 (ja) | 2006-06-13 | 2013-06-05 | チバ ホールディング インコーポレーテッド | トリカチオン性染料 |
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EP2667947B1 (en) | 2011-01-28 | 2018-07-25 | Momentive Performance Materials GmbH | Uv-photo-protecting cosmetic composition |
JP6100897B2 (ja) | 2012-07-13 | 2017-03-22 | ロレアル | 複合顔料及びその調製方法 |
US11266584B2 (en) | 2012-07-13 | 2022-03-08 | L'oreal | Cosmetic composition comprising composite sunscreen particles |
WO2014010099A1 (en) | 2012-07-13 | 2014-01-16 | L'oreal | Composite pigment and method for preparing the same |
JP6096897B2 (ja) | 2012-07-13 | 2017-03-15 | ロレアル | 化粧料組成物 |
FR2993176B1 (fr) | 2012-07-13 | 2014-06-27 | Oreal | Composition cosmetique contenant des particules composites filtrantes de taille moyenne superieure a 0,1 micron et des particules de filtre inorganique et une phase aqueuse |
MX354866B (es) | 2013-01-21 | 2018-03-23 | Oreal | Composicion cosmetica o dermatologica que comprende una merocianina y un agente de filtro ultravioleta (uv) organico insoluble y/o un agente de filtro ultravioleta (uv) inorganico insoluble. |
KR102244166B1 (ko) | 2013-09-02 | 2021-04-26 | 로레알 | 양이온성 스티릴 디술파이드 염료를 사용하는 케라틴 섬유 염색 방법, 및 상기 염료를 포함하는 조성물 |
CN106163492B (zh) | 2014-04-11 | 2019-12-13 | 巴斯夫欧洲公司 | 化妆品uv吸收剂的混合物 |
WO2016030839A1 (fr) | 2014-08-28 | 2016-03-03 | L'oreal | Composition gel/gel comprenant un filtre uv |
EP3223777A1 (fr) | 2014-11-24 | 2017-10-04 | L'Oréal | Composition cosmetique comprenant un phyllosilicate synthetique et un polyol et/ou un filtre uv |
FR3037243B1 (fr) | 2015-06-11 | 2018-11-16 | L'oreal | Composition comprenant un filtre uv, un polymere hydrophile reticule anionique, un tensioactif ayant une hlb inferieure ou egale a 5 et un copolymere silicone |
FR3073408B1 (fr) | 2017-11-15 | 2019-10-11 | L'oreal | Compositions comprenant au moins un polymere acrylique et au moins un filtre organique insoluble |
FR3083093A1 (fr) | 2018-06-28 | 2020-01-03 | L'oreal | Composition photoprotectrice comprenant des particules de silice colloidale |
CN109053609B (zh) * | 2018-08-03 | 2020-10-09 | 浙江工业大学 | 一种三苯胺-三嗪衍生物及其制备方法与应用 |
FR3090329B1 (fr) | 2018-12-21 | 2020-12-04 | Oreal | Composition comprenant un filtre UV, un polymère hydrophile réticulé anionique, un tensioactif ayant une HLB inférieure ou égale à 5 et un alcane non volatil |
FR3103705B1 (fr) | 2019-11-29 | 2021-12-17 | Oreal | Composition comprenant un filtre UV, un polymère séquencé à groupe acide phosphonique et une huile hydrocarbonée |
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Also Published As
Publication number | Publication date |
---|---|
AU736424B2 (en) | 2001-07-26 |
US6217856B1 (en) | 2001-04-17 |
KR100514940B1 (ko) | 2005-09-15 |
RU2191178C2 (ru) | 2002-10-20 |
CN1237966A (zh) | 1999-12-08 |
ATE250040T1 (de) | 2003-10-15 |
ID21704A (id) | 1999-07-15 |
DE69724992D1 (de) | 2003-10-23 |
BR9713109A (pt) | 2000-04-11 |
DE69724992T2 (de) | 2004-07-22 |
AU5320198A (en) | 1998-06-10 |
ES2205268T3 (es) | 2004-05-01 |
JP2001504126A (ja) | 2001-03-27 |
IL129644A0 (en) | 2000-02-29 |
BR9713109B1 (pt) | 2009-05-05 |
KR20000069055A (ko) | 2000-11-25 |
JP4252627B2 (ja) | 2009-04-08 |
EP0941217A1 (en) | 1999-09-15 |
WO1998022447A1 (en) | 1998-05-28 |
EP0941217B1 (en) | 2003-09-17 |
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