CN1662215A - 苯并噁唑和苯并二唑uv-a防晒剂 - Google Patents
苯并噁唑和苯并二唑uv-a防晒剂 Download PDFInfo
- Publication number
- CN1662215A CN1662215A CN038149613A CN03814961A CN1662215A CN 1662215 A CN1662215 A CN 1662215A CN 038149613 A CN038149613 A CN 038149613A CN 03814961 A CN03814961 A CN 03814961A CN 1662215 A CN1662215 A CN 1662215A
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- China
- Prior art keywords
- chemical compound
- acid
- ester
- benzal
- benzoxazole
- Prior art date
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- Granted
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- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 title abstract description 4
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- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D263/57—Aryl or substituted aryl radicals
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
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- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
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- C07F7/02—Silicon compounds
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- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
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- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
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Abstract
本发明涉及1,3-苯并噁唑或苯并二唑UV-A防晒剂并且涉及含有上述UV-A防晒剂的组合物,特别为局部组合物。
Description
本发明涉及新型UV-A防晒剂并涉及含有上述UV-A防晒剂的组合物、特别是局部组合物。
根据波长UV射线被指定为UV-A射线(320-400nm)和UV-B射线(280-320nm)。UV射线对人体皮肤的损伤作用随着波长的降低和暴露持续时间的增加而增加。因此UV射线会造成皮肤损伤,并且UV-B辐射可能会造成晒斑(红斑)直至非常严重的皮肤灼伤。阳光对皮肤非常频繁且无保护的照射同样会导致皮肤弹性的损失和皱纹形成的增加,总体来说会导致皮肤的过早老化。在极端情况下,会发生病态皮肤变化至皮肤癌。
UV-A辐射可导致皮肤迅速而微弱地直接形成色素。UV-A射线可穿入较深的皮肤层中并且会加速皮肤老化过程。UV-A辐射还会引起皮肤感光反应或光过敏反应。在UV-A照射和增加的皮肤癌危险之间存在着确定的联系。根据它们的最大吸收值的位置,用于化妆品和皮肤病制剂的UV吸收剂分为UV-A吸收剂和UV-B吸收剂。尽管存在大量安全而有效的UV-B吸收剂,但是适于保护人体皮肤的UV-A吸收剂很少,而且会受到重大缺陷的影响。
EP-A1-669323、DE-3644633、DE4107439公开了例如在UV-A范围内吸收的苯并二唑、苯并噻唑和/或苯并噁唑。根据这些现有技术文献的化合物的脂溶性低,其化学结构与根据本发明的那些化合物差别很大。这是重大缺点,因为通常必须将UV-防晒剂加入化妆品和/或皮肤病组合物的脂质相中以确保进入皮肤的最佳吸收作用。
此外,引用的现有技术的UV-A防晒剂通常不能显示出耐光性。由于当暴露于阳光下时它们会释放其活性,因而这是附加的缺点。
本发明的根本目的是提供可以克服上述缺点的UV-A防晒剂,即具有良好脂溶性和高耐光性的UV-A防晒剂。
可以通过提供通式I的化合物实现该目的
其中
R1和R2相互独立地为氢;卤素;羟基;(C1-C20)-烷基;(C2-C20)-烯基;或(C1-C20)-烷氧基;
X是氧或亚氨基,任选地被R1取代;
R3和R4相互独立地为氰基;-COOR5;-COR6;-CONH2;-CONHR7或-CONR8R9;
R5、R6、R7、R8和R9相互独立地为氢;(C1-C20)-烷基,其中一个或多个亚甲基任选地被氧代替;(C1-C20)-卤代烷基;(C2-C20)-烯基,任选地被三(C1-C5)-烷基甲硅烷基或三苯基甲硅烷基或者基团-Si[CH3]n[OSi(CH3)3]3-n取代,其中n为0、1、2或3。
通式I的化合物是重要的耐光制品,其最大吸收值处于UV-A范围内。此外,它们是亲脂性的,因此适于加入防晒剂的脂质相。
如这里所使用的,C1-C20-烷基表示具有1-20个碳原子的直链或支链烷基片断,例如甲基、乙基、丙基、异丙基、叔己基(=1,1,3,3-四甲基-丁基)、1,1,2-三甲基丙基、正丁基、仲丁基、叔丁基、戊基、新戊基、己基、2-乙基己基、辛基等。优选的是C1-C8-烷基。
C2-C20-烯基表示具有2-20个碳原子并且含有至少一个C-C双键的直链或支链烯基片断,例如乙烯基、烯丙基、2-丁烯基、甲代烯丙基、2-戊烯-3-基、3-己烯-2-基、3-庚烯-2-基、3-辛烯-2-基、1-辛烯-3-基和2-辛烯-1-基。优选的是C2-C8-烯基。
“其中一个或多个亚甲基任选地被氧代替的(C1-C20)-烷基”的实例是甲氧基甲基、4-氧杂-己基、4,7-二氧杂-壬基和4,7,10-三氧杂-十二烷基。
三(C1-C5)-烷基甲硅烷基片断是基团-SiRaRbRc,其中Ra、Rb和Rc分别独立地为C1-C5-烷基。优选的甲硅烷基片断是三甲基甲硅烷基、三乙基甲硅烷基、三丙基甲硅烷基、三异丙基甲硅烷基、二甲基叔丁基甲硅烷基、二甲基叔己基甲硅烷基等。优选的三取代的甲硅烷基是三甲基甲硅烷基、三乙基甲硅烷基和三苯基甲硅烷基。
通式I的化合物可以通过通式IIIa(如果X为O)或IIIb(如果X为NH或NR1)的化合物与通式IV的化合物缩合而制备,
其中R1、R2、R3和R4具有上文给出的含义。
在酸性催化剂存在下进行所述形成杂环的缩合反应。任何强无机或有机酸例如H2SO4、HCl、H3PO4、H3BO3或对-甲苯磺酸可以用于该目的。由该反应形成的水可以通过共沸蒸馏(例如使用甲苯或CH2Cl2作为溶剂)或者通过吸湿剂例如P2O5除去。反应温度可以为0℃-200℃并取决于所述酸的浓度和强度。
通式IV的起始物质可以通过Knoevenagel缩合而获得,即通过将通式V的化合物(任选地以与烷醇形成的酯形式)与通式VI的化合物反应而获得。
所述缩合反应可以例如在可与水形成共沸物的溶剂(如甲苯或氯仿)和水分离器存在下于共沸蒸馏下进行。酸和/或碱可以用作催化剂:酸类,例如醋酸、苯甲酸、甲苯磺酸、硫酸、BF3;或者碱类,例如吡啶、哌啶或吗啉。酸酐例如P2O5也可以催化该反应。
通式I的化合物也可以通过变换上面步骤的顺序而制备,即通过将通式VII的化合物与通式VI的化合物反应而制备。
按照其顺序,通式VII的化合物可以通过将通式IIIa(X=O)或IIIb(X=NH或NR1)的化合物与通式V的化合物反应而获得。一般反应条件与上文所述的闭环作用的相同。
优选的式I化合物是其中X为O的那些。另外,特别优选的化合物是其中R1和R2为氢的那些,以及其中R3为氰基和R4为-COOR5的那些。这些化合物的实例是:
2-氰基-3-{4-[5-叔丁基-苯并噁唑-2-基]-苯基}-丙烯酸2-乙基己酯和
2-氰基-3-{4-苯并噁唑-2-基-苯基}-丙烯酸2-乙基己酯。
另外优选其中R3和R4相互独立地为-COOR5的化合物。这些化合物的实例是:
2-(4-苯并噁唑-2-基-亚苄基)-丙二酸二乙酯;
2-(4-苯并噁唑-2-基-亚苄基)-丙二酸二丁酯;
3-{4-苯并噁唑-2-基-苯基}-2-丙酰基-丙烯酸2-乙基己酯;
2-(4-[6-羟基-苯并噁唑-2-基]-亚苄基)-丙二酸二乙酯;
2-(4-[6-{2-乙基-己氧基}-苯并噁唑-2-基]-亚苄基)-丙二酸二乙酯;和
2-(4-{6-[2-(2-乙氧基-乙氧基)-乙氧基]-苯并噁唑-2-基}-亚苄基)-丙二酸二乙酯。
另一方面,本发明涉及通式II的取代聚硅氧烷
(H3C)3Si-(B)q-OSi(CH3)3 II
其中
B是选自B1、B2、B3、B4和B5的片断;
W是选自W1、W2和W3的片断,
其中X、R1、R2、R3和R4如上文定义的;Y为氧、(C1-C20)-亚烷基、(C2-C20)-亚烯基或-O-(C1-C20)-亚烷基;Y’为(C1-C20)-亚烷基或(C2-C20)-亚烯基,
q为1-400的整数并且代表任意顺序的片断B1-B5的总和,
其中至少一个B为B1、B2、B3或B4,比值
(B1+B2+B3+B4)/(B1+B2+B3+B4+B5)不超过0.6。
优选的式II聚硅氧烷是其中q为2-100的那些。特别优选的式II聚硅氧烷是比值(B1+B2+B3+B4)/(B1+B2+B3+B4+B5)为0.01-0.4的那些。
优选的式II聚硅氧烷是
通式II的化合物可以通过将式VIII化合物
接枝到聚(甲基-氢硅氧烷)上而制备,
其中m+p=q,
q如上文定义的,
并且不同片断的顺序任意。
显然可以通过化合物IX的氢化物含量(即基团-Si[H][CH3]-O-的含量)确定反应组分的摩尔比。
通常,在纯聚硅氧烷中或者在例如甲苯、THF或异丙醇中的聚硅氧烷溶液中进行所述反应。所述反应可以在均相催化剂(Karstedt催化剂)或者非均相铂催化剂(氯铂酸)存在下于40-150℃、优选60-100℃下进行该反应2-48小时。
式VIIIaa和VIIIab的化合物可以通过在使用碱(例如KOH或K2CO3)的情况下于50-150℃在极性非质子溶剂例如N-甲基吡咯烷酮或丁酮中分别采用a)炔丙基溴或b)烯丙基溴处理其中R2为OH的式VII化合物而获得。这种新型的式VIIaa或VIIab化合物可以用如上所述的化合物VI处理。式VIIIba和VIIIbb化合物可以相应地在上述条件下从其中X为NH或NR1的化合物VII开始而获得。式VIIIca和VIIIcb化合物可以通过在将其中R3为CN和R4为COOR5的式VI化合物与如上所述的化合物VII反应之前,处理其中R3为CN和R4为COOR5的式VI化合物(化合物VI’)以分别得到式VI”或VI化合物而获得。
表示双或三键
为了获得化合物VI”,在室温下用干燥的HCl或浓H2SO4处理化合物VI’,接着分别加入炔丙醇或丙烯醇,并使所述铵盐中间体水解。分别使用过量的炔丙醇或丙烯醇通过酯交换作用由化合物VI’形成化合物VI。
本发明的另一方面涉及将一种或多种式I和/或II化合物用作UV-A防晒剂。特别地,通式I和/或II的化合物适于保护人体皮肤和/或人的毛发以防UV-A辐照,以及适于保护UV敏感的塑料材料和医用制品。
本发明的另一方面提供了含有一种或多种式I和/或II化合物和至少一种药学和/或化妆品可接受的赋形剂的组合物、特别是局部组合物。
含有一种或多种式I或II化合物的组合物特别适于局部施用于到人体皮肤和/或毛发上。因此,它们适于保护对紫外辐射特别是太阳辐射敏感的材料,并且包含有效光防护量的至少一种式I或II化合物。在本发明的一个优选实施方案中,这种组合物适于保护人体皮肤和/或人的毛发免受UV辐射的有害作用。在这种情况下,根据本发明的组合物是包含可局部施用的、化妆用可接受的赋形剂作为载体和稀释剂的化妆品和/或皮肤病组合物。
如果合适,可以将另外的UV-A和UV-B防晒剂加入本发明的化妆品和/或皮肤病组合物中。不同的UV防晒剂组合还可以表现出协同作用。
UV防晒剂的总量(即通式I和/或II化合物和另外的UV-A/B防晒剂的总量)不是关键所在。合适的量可以为所述组合物总量的0.5-20wt%,优选为0.5-12wt%。
可以加入本发明的UV-A防晒剂中的合适的UV-B防晒剂为下列有机和无机化合物:
·丙烯酸酯,例如2-乙基己基-2-氰基-3,3-二苯基丙烯酸酯(octocrylene,PARSOL340),2-氰基-3,3-二苯基丙烯酸乙酯等;
·樟脑衍生物例如4-甲基亚苄基樟脑(PARSOL5000)、3-亚苄基樟脑、樟脑苄烷铵硫酸甲酯、聚丙烯酰氨基甲基亚苄基樟脑、硫代亚苄基樟脑、硫代甲基亚苄基樟脑、对苯二叉基二樟脑磺酸(therephthalidenedicamphor sulfonic acid)等;
·肉桂酸酯衍生物例如甲氧基肉桂酸辛酯(PARSOLMCX)、甲氧基肉桂酸乙氧基乙酯、甲氧基肉桂酸二乙醇胺酯(PARSOLHydro)、甲氧基肉桂酸异戊酯等,以及连接到硅氧烷上的肉桂酸衍生物;
·对-氨基苯甲酸衍生物例如对-氨基苯甲酸、对-二甲基氨基苯甲酸2-乙基己酯、N-氧基丙烯化的对-氨基苯甲酸乙酯、对-氨基苯甲酸甘油酯;
·二苯酮例如二苯酮-3、二苯酮-4、2,2′,4,4′-四羟基-二苯酮、2,2′-二羟基-4,4′-二甲氧基二苯酮等;
·亚苄基丙二酸的酯例如4-甲氧基亚苄基丙二酸二(2-乙基己基)酯;
·2-(4-乙氧基-苯胺基亚甲基)-丙二酸的酯例如2-(4-乙氧基-苯胺基亚甲基)-丙二酸二乙酯(EP-A2-0895776);
·含有如欧洲专利公开EP-B1-0358584、EP-B1-0538431和EP-A1-0709080中描述的亚苄基丙二酸酯基团(benzmalonate)的有机硅氧烷化合物;
·苯并三唑三硅氧烷(drometrizole trisiloxane,Mexoryl XL);
·颜料例如微粒状TiO2等,术语“微粒状”是指约5nm-约200nm的颗粒尺寸,特别是约15nm-约100nm。TiO2颗粒也可以涂覆金属氧化物例如氧化铝或氧化锆,或者涂覆有机涂料例如多元醇、甲基硅油、硬脂酸铝、烷基硅烷等。这些涂料是现有技术中公知的。
·咪唑衍生物例如2-苯基苯并咪唑磺酸及其盐(PARSOLHS)。2-苯基苯并咪唑磺酸盐,例如碱金属盐如钠或钾盐、铵盐、吗啉盐、伯胺盐、仲胺盐和叔胺盐例如单乙醇胺盐、二乙醇胺盐等。
·水杨酸酯衍生物例如水杨酸异丙基苄酯、水杨酸苄酯、水杨酸丁酯、水杨酸辛酯(NEO HELIOPAN OS)、水杨酸异辛酯或水杨酸高孟酯(homosalate,HELIOPAN)等。
·三嗪酮衍生物例如辛基三嗪酮(UVINUL T-150)、二辛基丁酰氨基三嗪酮(UVASORB HEB)等。
可以加入本发明的UV-A防晒剂中的合适的常规UV-A防晒剂是下列有机和无机化合物:
·二苯甲酰甲烷衍生物例如4-叔丁基-4′-甲氧基二苯甲酰基-甲烷(PARSOL1789)、二甲氧基二苯甲酰基甲烷、异丙基二苯甲酰基甲烷等;
·苯并三唑衍生物例如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(TINOSORB M)等;
·亚苯基-1,4-二-苯并咪唑磺酸或盐例如2,2-(1,4-亚苯基)-二-(1H-苯并咪唑-4,6-二磺酸)(Neoheliopan AP);
·氨基取代的羟基二苯酮例如如欧洲专利公开EP1046391中描述的2-(4-二乙基氨基-2-羟基-苯甲酰基)-苯甲酸己酯;
·颜料例如微粒状ZnO等。术语“微粒状”是指约5nm-约200nm的颗粒尺寸,特别是约15nm-约100nm。ZnO颗粒也可以涂覆金属氧化物例如氧化铝或氧化锆,或者涂覆有机涂料例如多元醇、甲基硅油、硬脂酸铝盐、烷基硅烷等涂覆。这些涂料是现有技术中公知的。
由于二苯甲酰基甲烷衍生物是光不稳定的UV-A防晒剂,理想的是使其光稳定化。因此,术语“常规的UV-A防晒剂”还指通过例如下列物质稳定的二苯甲酰基甲烷衍生物例如PARSOL1789
·EP-B1-0514491和EP-A1-0780119中描述的3,3-二苯基丙烯酸酯衍生物;
·USP-5605680中描述的亚苄基樟脑衍生物;
·EP-B1-0358584、EP-B1-053843和EP-A1-0709080中描述的含有亚苄基丙二酸酯(benzmalonate)基团的有机硅氧烷;
本发明的组合物还可以含有常用的化妆品助剂和添加剂,例如防腐剂/抗氧化剂、脂肪物质/油、水、有机溶剂、聚硅氧烷、增稠剂、软化剂、乳化剂、附加的防晒剂、消泡剂、保湿剂、香料、表面活性剂、填料、螯合剂、阴离子聚合物、阳离子聚合物、非离子聚合物或两性聚合物或其混合物、推进剂、酸化剂或碱化剂、染料、着色剂、颜料或纳米颜料,特别是适于通过物理遮蔽紫外辐射提供附加光保护作用的那些,或者通常配入化妆品的任何其他成分,特别是用于制备防晒/抗光组合物的那些。技术人员可以容易地根据所需制品而选择化妆品和皮肤病用助剂和添加剂的必要量。
特别优选的抗氧化剂是选自以下物质的那些:氨基酸(例如甘氨酸、组氨酸、酪氨酸、色氨酸)和它们的衍生物;咪唑(例如尿刊酸)和衍生物;肽类,例如D,L-肌肽、D-肌肽、L-肌肽和衍生物(例如鹅肌肽);类胡萝卜素、胡萝卜素(例如β-胡萝卜素、γ-胡萝卜素、番茄红素)和衍生物;绿原酸和衍生物;脂酮酸和衍生物(例如二氢脂酮酸);硫代葡萄糖金、丙基硫尿嘧啶和其他硫醇(例如thioredoxine、谷胱甘肽、半胱氨酸、胱氨酸、胱胺和其糖基-、N-乙酰基-、甲基-、乙基-、丙基-、戊基-、丁基-和月桂基-、棕榈酰基-、油基-、γ-亚油基-、胆甾醇基-和甘油基酯)和其盐;二月桂基硫代二丙酸酯、二硬脂基硫代二丙酸酯、硫代二丙酸和其衍生物(酯、醚、肽、脂质、核苷酸、核苷和盐类)以及非常低的相容剂量(例如从pmol-μmol/kg)的亚砜胺化合物(例如丁硫氨酸亚砜胺、高半胱氨酸亚砜胺、丁硫氨酸砜、戊-、己-、庚-硫氨酸亚砜胺);附加的(金属)螯合剂(例如α-羟基脂肪酸、棕榈酸、肌醇六磷酸、乳铁蛋白);α-羟基酸(例如柠檬酸、乳酸、苹果酸)、huminic acid、没食子酸、没食子提取物(gallic extract)、胆红素、胆绿素、EDTA、EGTA和其衍生物;不饱和脂肪酸和其衍生物(例如γ-亚油酸、亚油酸、油酸);叶酸和其衍生物;泛醌和泛醇以及它们的衍生物;维他命C和衍生物(例如酸棕榈抗坏血酸酯、Mg-抗坏血酸磷酸酯、Na-抗坏血酸磷酸酯、醋酸抗坏血酸酯);生育酚和衍生物(例如维他命E醋酸酯);维他命A和衍生物(维他命A棕榈酯)以及松柏基苯甲酸酯、芸香亭酸和衍生物、α-糖基芸香苷、阿魏酸、亚糠基葡糖醇、肌肽、丁羟基甲苯、丁羟基茴香醚、三羟基丙基苯基酮、脲和其衍生物;甘露糖和衍生物;锌和衍生物(例如ZnO;ZnSO4);硒和衍生物(例如硒甲硫氨酸);芪和衍生物(例如氧化芪、反式-氧化芪)和提到的活性成分的合适衍生物(盐、酯、醚、糖、核苷酸、核苷、肽和脂质)。
防腐剂和/或抗氧化剂可以存在的量为所述组合物总重量的约0.01wt%-约10wt%。优选地,防腐剂和/或抗氧化剂存在的量为约0.1wt%-约1wt%。
根据本发明的组合物还可以含有乳化剂。乳化剂可以使两种或更多种不可混溶的液体均匀混合,同时提高该组合物的粘度。此外,乳化剂起到稳定所述组合物的作用。
可以根据本发明使用的形成O/W、W/O和/或O/W/O型制剂的乳化剂包括油酸失水山梨糖醇酯、倍半油酸失水山梨糖醇酯、异硬脂酸失水山梨糖醇酯、三油酸失水山梨糖醇酯、聚甘油基-3-二异硬脂酸酯、油酸/异硬脂酸的聚甘油酯、聚甘油基-6-六蓖麻油酸酯、聚甘油基-4-油酸酯、聚甘油基-4-油酸酯/PEG-8丙二醇椰酸酯、油酰胺DEA、TEA肉豆蔻酸酯、TEA硬脂酸酯、硬脂酸镁、硬脂酸钠、月桂酸钾、蓖麻油酸钾、椰酸钠、牛油酸钠、海狸香酸钾(potassium castorate)、油酸钠和其混合物。其他合适的乳化剂是磷酸酯和其盐,例如磷酸鲸蜡基酯、DEA磷酸鲸蜡基酯、磷酸十六烷基酯钾盐、油酸甘油酯磷酸钠(sodium glyceryl oleate phosphate)、氢化的植物甘油酯磷酸盐(glyceride phosphate)和其混合物。此外,一种或多种合成聚合物可以用作乳化剂。例如,PVP二十碳烯共聚物(PVPeicosanene copolymer)、丙烯酸酯/丙烯酸C10-C30烷基酯交叉聚合物(crosspolymer)、丙烯酸酯/甲基丙烯酸硬脂基酯共聚物、PEG-22/十二烷基二醇共聚物、PEG-45/十二烷基二醇共聚物和其混合物。优选的乳化剂是PVP二十碳烯共聚物、丙烯酸酯/丙烯酸C10-C30烷基酯交叉聚合物、PEG-20失水山梨糖醇异硬脂酸酯、异硬脂酸失水山梨糖醇酯和其混合物。
乳化剂存在的总量为所述组合物总重量的约0.01wt%-约15wt%,优选约0.1wt%-约3wt%。
脂肪/油相有利地选自:
·矿物油和矿物蜡;
·油例如癸酸或辛酸的三甘油酯,优选蓖麻油;
·天然或合成油,优选碳酸或脂肪酸与醇例如异丙醇、丙二醇或甘油的酯;
·苯甲酸烷基酯和
·聚硅氧烷例如二甲基聚硅氧烷、二乙基聚硅氧烷、二苯基聚硅氧烷和其混合物。
可以加入本发明组合物的油相的脂肪物质有利地选自:具有3-30个碳原子的饱和和/或不饱和的直链或支链烃基羧酸与具有3-30个碳原子的饱和和/或不饱和的直链和/或支链醇的酯,以及芳族羧酸和具有3-30个碳原子的饱和和/或不饱和的直链或支链醇的酯。这些酯可以有利地选自:棕榈酸辛酯、椰油酸辛酯、异硬脂酸辛酯、肉豆蔻酸辛基十二烷基酯、异壬酸鲸蜡基酯、肉豆蔻酸异丙酯、棕榈酸异丙酯、硬脂酸异丙酯、油酸异丙酯、硬脂酸正丁酯、月桂酸正己酯、油酸正癸酯、硬脂酸异辛酯、硬脂酸异壬酯、异壬酸异壬酯、棕榈酸2-乙基己酯、月桂酸2-乙基己酯、硬脂酸2-己基癸酯、棕榈酸2-辛基十二烷基酯、庚酸硬脂基酯、油酸油基酯、芥酸油基酯、油酸瓢菜心基酯、芥酸瓢菜心基酯、硬脂酸三癸酯、偏苯三酸三癸酯,以及选自这些酯的合成混合物、半合成混合物和天然混合物例如霍霍巴油。
适用于本发明组合物的其他脂肪组分包括极性油例如卵磷脂和脂肪酸三甘油酯,即8-24个碳原子、优选12-18个碳原子的饱和和/或不饱和的直链或支链含碳酸的三甘油酯,然而脂肪酸三甘油酯优选选自合成油、半合成油和天然油(例如椰油甘油酯、橄榄油、向日葵油、豆油、花生油、菜油、杏仁油、棕榈油、椰子油、蓖麻油、氢化蓖麻油、麦油、葡萄油和其他油);非极性油例如线型和/或支链烃和蜡,例如矿物油、凡士林(矿脂);石蜡、角鲨烷和角鲨烯、聚烯烃(有利的是聚癸烯)、氢化的聚异丁烯和异十六烷;二烷基醚例如二辛酰基醚;线型或环状硅油例如环甲基硅油、八甲基环状四聚硅氧烷、十六烷基二甲硅油、六甲基环三硅氧烷、聚二甲基硅氧烷、聚(甲基苯基硅氧烷)和其混合物。
可以有利地加入本发明组合物中的其他脂肪组分是异二十烷;二庚酸新戊二醇酯;二辛酸/二癸酸丙二醇酯;琥珀酸辛酯/癸酯/二甘油酯;辛酸/癸酸丁二醇酯;乳酸C12-13烷基酯;酒石酸二C12-13烷基酯;异甘油三硬脂酸酯;六辛酸/六癸酸二季戊四醇酯;单异硬脂酸丙二醇酯;甘油三辛酸酯;异山梨酸二甲酯。特别优选使用苯甲酸C12-15烷基酯和异硬脂酸2-乙基己酯的混合物、苯甲酸C12-15烷基酯和异壬酸异三癸酯的混合物以及苯甲酸C12-15烷基酯、异硬脂酸2-乙基己酯和异壬酸异三癸酯的混合物。
本发明组合物的油相还可以含有天然植物蜡或动物蜡例如蜂蜡、中国蜡、大黄蜂蜡和其他昆虫蜡以及牛油树脂。
本发明组合物可以另外含有一种或多种润肤剂。润肤剂为皮肤表面提供软化或平滑作用并且通常被认为就局部使用而言是安全的。润肤剂也有助于控制蒸发速率和所述组合物的粘性。优选的润肤剂包括矿物油、羊毛脂油、椰子油、可可脂、橄榄油、芦荟提取物、霍霍巴油、蓖麻油、脂肪酸例如油酸和硬脂酸、脂肪醇例如鲸蜡基醇和十六烷基醇、己二酸二异丙基酯、C9-C15醇的苯甲酸酯和羟基苯甲酸酯、异壬酸异壬酯、C15-C50烷烃、矿物油、硅氧烷例如二甲基聚硅氧烷、醚例如聚氧化丙烯丁醚和聚氧化丙烯鲸蜡基醚,和苯甲酸C2-C15烷基酯及其混合物。最优选的润肤剂是羟基苯甲酸酯、芦荟、苯甲酸C12-15烷基酯及其混合物。
润肤剂存在的量为所述组合物总重量的约1wt%-约20wt%,优选约2wt%-约15wt%,最优选约4wt%-约10wt%。
本发明制剂的水相可以含有常用的化妆品添加剂例如醇,尤其是低级醇,优选乙醇和/或异丙醇、低级烷基二醇或多元醇及其醚,优选丙二醇、丙三醇、乙二醇、乙二醇单乙醚或乙二醇单丁醚、丙二醇单甲醚、丙二醇单乙醚或丙二醇单丁醚、二甘醇单甲醚或单乙醚和类似制品、聚合物、泡沫稳定剂;电解质和尤其是一种或多种增稠剂。
可以用于本发明制剂的增稠剂包括二氧化硅类、硅酸镁和/或硅酸铝类、多糖和其衍生物例如透明质酸、黄原胶、羟丙基纤维素、丙烯酸酯共聚物,优选卡波姆类的聚丙烯酸酯例如980、981、1382、2984、5984型卡波姆。
保湿剂,例如湿润剂可以加入本发明的组合物中以减少皮肤角质层的经皮失水(TEWL)。合适的湿润剂包括甘油、乳酸、吡咯烷酮、碳酸、脲、聚乙二醇、聚丙二醇、失水山梨糖醇、PEG-4和其混合物。另外合适的保湿剂是水溶型聚合物保湿剂和/或遇水凝胶化的多糖例如透明质酸、壳聚糖和/或可从SOLABIA S获得的富含海藻糖的多糖例如Fucogel1000(CAS-Nr.178463-23-5)。任选存在的保湿剂的量为所述组合物总重量的约0.5wt%-约8wt%,优选约1wt%-约5wt%。
合适的中和剂也可以包含在本发明组合物中,例如乳化剂、泡沫清洁剂(foam builder)和稳定剂。合适的中和剂包括碱金属氢氧化物例如氢氧化钠或氢氧化钾;有机碱例如二乙醇胺、三乙醇胺、氨基甲基丙醇、亚乙基二胺四乙酸三钠;碱性氨基酸例如精氨酸和赖氨酸;以及上述任何物质的任意组合。任选存在的中和剂的量为所述组合物总重量的约0.01wt%-约8wt%,优选约1wt%-约5wt%。
优选向本发明组合物中加入电解质以改变疏水型乳化剂的性能。因此,本发明的微乳液优选含有具有阴离子的一种或几种盐的电解质,所述盐包括但不限于盐酸盐、硫酸盐、碳酸盐、硼酸盐和铝酸盐。其他合适的电解质可以基于有机阴离子,例如但不限于乳酸盐、醋酸盐、苯甲酸盐、丙酸盐、酒石酸盐和柠檬酸盐。优选的阳离子是铵离子、烷基铵离子、碱金属离子、镁离子、铁离子和锌离子。特别优选的盐是氯化钾和氯化钠、硫酸镁、硫酸锌和其混合物。电解质存在的量为所述组合物总重量的约0.01wt%-约8wt%。
本发明组合物可用于对人体表皮或毛发进行光保护以防紫外辐射的损伤作用,其可以作为抗光/防晒组合物或化妆品。这些组合物可以特别地以洗液、增稠洗液、凝胶、膏状物、乳状物、软膏、粉末或固体管棒的形式提供,并可以任选地包装成气溶胶,以及可以以摩丝、泡沫或喷射剂形式提供。它们可以呈溶剂中的悬浮液或分散液形式或者脂肪物质形式,或者作为选择地乳液形式(优选O/W型例如膏状物或乳状物、起泡分散体)、软膏、凝胶、固体管棒或者气溶胶摩丝形式。该乳液还可以含有阴离子、非离子、阳离子或两性表面活性剂。
当本发明的化妆品组合物用于保护毛发时,它们可以呈洗液、凝胶或清洗组合物例如香波或者护发剂形式,并可在用洗发之前或之后施用、在染色或漂色之前或之后施用、在进行持久卷发或拉直头发期间或之后施用,还可以呈定型液或处理液或者凝胶、吹干液或固发液或者凝胶、发胶、或者持久卷发、拉直、染色或漂色用组合物形式。
通过下列实施例进一步阐述本发明。
实施例1 2-(4-苯并噁唑-2-基-亚苄基)-丙二酸二乙酯
a)对-羧基-亚苄基丙二酸二乙酯
向装有具有水分离器的回流冷凝器和带有磁力搅拌器的油浴的500ml三颈反应烧瓶中装入300ml甲苯中的1.4g对-甲苯磺酸、24.8g(170mmol)4-羧基-苯甲醛(Fluka)、26.3g(170mmol)丙二酸二乙酯和1.3g吗啉。回流2小时后分离3ml水。用醋酸乙酯稀释该反应混合物并用NH4Cl和NaCl的水溶液清洗,用Na2SO4干燥并将其浓缩以得到褐色的蜜状物。从甲苯中重结晶提供18g褐色晶体。熔点100-102℃。UV(乙醇)286nm(E=24’800)
b)2-(4-苯并噁唑-2-基-亚苄基)-丙二酸二乙酯
在250ml圆底烧瓶中将10g五氧化磷、25ml六甲基二聚硅氧烷和50ml1,2-二氯苯混合并回流数分钟,直到该混合物变得澄清。
将1.5g上面获得的对-羧基-亚苄基丙二酸二乙基酯和0.66g 2-氨基苯酚溶解于15ml该澄清的五氧化磷混合物中并回流4小时。然后用150ml醋酸乙酯稀释所述冷反应混合物,并用1n NaOH和NaCl水溶液对其进行萃取。用Na2SO4干燥有机相,并将其浓缩以得到1g褐色晶体,在己烷∶醋酸乙酯=3∶1(v/v)中通过硅胶对其进行色谱分析,获得0.77g黄色晶体产物。熔点99-102℃。UV(CH2Cl2)331nm(E=1010);MS:365(M+),320、291、275、247、219(100%)。
溶解度测试
将分别含有Cétiol LC(椰油基辛酸酯癸酸酯)和Crodamol DA(己二酸二异丙酯)的过量UV防晒剂置于烧瓶中。混合该悬浮液并在超声浴中处理10分钟。于室温下静置18小时后,将残留晶体上的溶液通过微孔微型过滤器(孔径0.45μm)过滤。通过UV光谱法对比校正曲线确定该饱和溶液的浓度。
发现该产物在Cétiol LC中的溶解度为4.5%,在Crodamol DA中的溶解度为11%。
光稳定性:
使用带有Pyrex过滤器(2.3mm)的150W Heraeus Hg灯和内径0.3mm、总长10m的Teflon毛细管,在Hg灯/HPLC在线系统中测量光稳定性。将3.6mg样品溶解于10ml MeOH中,并将10μl该溶液注入。不分离降解产物。周期性地测量被辐照的溶液在波长358nm处的UV吸收度达14分钟,并将结果与丁基甲氧基二苯甲酰基甲烷的对应光稳定性作比较。检测到该产物>90%,这表示具有光稳定性,然而在14分钟辐照后仅仅可以检测到16%的丁基甲氧基二苯甲酰基甲烷。
作为选择,根据描述于International Journal of Cosmetic Science
18,167-177(1996)的规程进行该测量。
实施例2 2-氰基-3-{4-[5-叔丁基苯并噁唑-2-基]-苯基}-丙烯酸2-乙基己酯
a)2-氰基-{对-羧基苯基}-丙烯酸2-乙基己酯
向装有具有水分离器的回流冷凝器和带有磁力搅拌器的油浴的250ml三颈反应烧瓶中装入80ml甲苯和20ml二甲基甲酰胺中的0.25g对-甲苯磺酸、3.8g(25mmol)4-羧基-苯甲醛(Fluka)、6.8g(33mmol)氰基乙酸2-乙基己酯和0.3g二(2-羟丙基)胺。回流22小时后,用甲苯稀释该反应混合物,并用NH4Cl和NaCl水溶液清洗,用Na2SO4干燥并将其浓缩以得到6.2g(74%)的白色晶体。熔点159-162℃。UV(CH2Cl2)305nm(E=811)。
b)2-氰基-3-{4-[5-叔丁基-苯并噁唑-2-基]-苯基}-丙烯酸2-乙基己酯
将上面获得的3.6g 2-氰基-{对-羧基-苯基}-丙烯酸2-乙基己酯和2.5g 2-氨基-4-叔丁基苯酚溶解于16ml澄清的五氧化磷混合物(实施例1b中所描述的)并回流4小时。然后用100ml氯仿稀释所述冷反应混合物,并用1nNaOH萃取3次,用NaCl水溶液萃取1次。用Na2SO4干燥所述有机相,并将其浓缩以得到褐色的蜜状物,用戊烷洗涤该蜜状物并在高真空下干燥。获得1.02g褐色晶体。熔点80-81℃。UV(CH2Cl2)363nm(E=816);
MS:458(M+)、443(100%)、409、346、331。
测定该产物在Cétiol LC中的溶解度为3.8%,在Crodamol DA中的溶解度为7.4%。用Heraeus的150W Hg灯辐照高度稀释的该产物,并且表现出具有光稳定性。
实施例3 2-(4-苯并噁唑-2-基-亚苄基)-丙二酸二丁酯
a)2-对-甲苯甲酰基-苯并噁唑
在氮气氛下向350ml三颈反应烧瓶中装入120ml二甘醇二乙醚和30ml二甘醇二丁醚中的1.5g H3BO3、40.8g苯乙酸和33g邻-氨基苯酚。首先将该混合物加热到180℃直到开始缓慢蒸馏。然后将其进一步加热10小时至220℃,直到在薄层色谱上实际上观察不到起始物质。在该阶段将90ml溶剂蒸出。将冷的晶体残留物溶解于醋酸乙酯中,并随后用1n NaOH、1n HCl和饱和NaCl水溶液清洗。将该有机相干燥并浓缩。用己烷洗涤结晶物质,并在高真空下干燥以得到29.5g褐色晶体。熔点104-105℃。UV:(CH2Cl2)303nm(E=1323)。
b)4-苯并噁唑-2-基-苯甲醛
在氮气氛下向装有磁力搅拌器、回流冷凝器和冰冷却浴的750ml圆底烧瓶中装入溶于200ml乙酸酐中的22g 2-对-甲苯甲酰基-苯并噁唑。将该混合物冷却到-5℃,并通过滴液漏斗缓慢加入44.5ml浓硫酸,同时将温度保持在低于0℃。然后在相同温度下缓慢加入溶于200ml乙酸酐中的15.3gCrO3溶液。在搅拌下将该绿色混合物放置过夜,然后倾倒在冰上。滤出沉淀物,用水洗涤,并在高真空下干燥以得到结晶形式的18.6g醛,其含有一些痕量的起始物质。熔点162-163℃。UV(CH2Cl2)324nm(E=1233)。
当加入CrO3溶液后立即处理该反应混合物,主要获得(大约73%含量) 4-苯并噁唑-2-基-苯甲醛-二乙酰基缩羰酯(4-benzoxazol-2-yl-benzaldehyde-diacetylacylal)。UV(CH2Cl2)302nm(E=964)。
c)2-(4-苯并噁唑-2-基-亚苄基)-丙二酸二丁酯
向装有具有水分离器的回流冷凝器和带有磁力搅拌器的油浴的50ml三颈反应烧瓶中装入30ml二甲苯中的0.17g对-甲苯磺酸、2.3g(10mmol)4-苯并噁唑-2-基-苯甲醛、2.6g(1.1mmol)丙二酸二正丁酯和0.25ml吗啉。回流5天后,用HPLC检测所需的主要产物。用醋酸乙酯稀释该反应混合物,并用水和NaCl溶液清洗,用Na2SO4干燥,并将其浓缩以得到4.9g褐色的蜜状物。在己烷/醋酸乙酯(9∶1-1∶1,v/v)中进行色谱分析,并得到1.5g黄色液体。UV(乙醇)329nm(E=758),MS:421(M+,100%)。
该产物与Cétiol LC混溶。用Heraeus的150W Hg灯以高稀释度对其进行辐照,表现出是光稳定的。
实施例4 2-氰基-3-{4-苯并噁唑-2-基-苯基}-丙烯酸2-乙基己酯
向装有回流冷凝器和带有磁力搅拌器的油浴的50ml三颈反应烧瓶中装入15ml甲苯中的0.31g干燥的ZnCl2、2g 4-苯并噁唑-2-基-苯甲醛-二乙酰基缩羰酯(73%产物含量,在实施例3b中描述)和1.0ml氰基乙酸2-乙基己酯。将该混合物加热20小时至50℃。然后加入水和NaOH以达到pH为9。用醋酸乙酯稀释该有机相,并用水和NaCl溶液清洗,用Na2SO4干燥并浓缩。在己烷/醋酸乙酯(9∶1-1∶1,v/v)中对残留物进行色谱分析,然后从己烷和甲苯中重结晶,得到0.7g 2-氰基-3-{4-苯并噁唑-2-基-苯基}-丙烯酸2-乙基己酯的黄色晶体。熔点84-85℃。UV(CH2Cl2)355nm(E=964);MS:402(M+)、290(100%)、273、246。
测定该产物在Cétiol LC中的溶解度为1.6%,在Crodamol DA中的溶解度为2.8%。用Heraeus的150W Hg灯以高稀释度辐照该产物,并在E/Z异构化后表现出是光稳定的。
实施例5 3-{4-苯并噁唑-2-基-苯基}-2-丙酰基-丙烯酸2-乙基己酯
进行如实施例4中的相同反应,但使用3-氧代-戊酸乙基酯代替氰基乙酸-2-乙基己酯。色谱分析后获得E-和Z-产物。Z-产物的数据:熔点82-83℃;UV(CH2Cl2)334nm(E=1083);MS:349(M+)、334、320(100%)、292、252。
用Heraeus的150W Hg灯以高稀释度辐照该产物,并在E/Z异构化后表现出是光稳定的。
实施例6 2-(4-[6-羟基-苯并噁唑-2-基]-亚苄基)-丙二酸二乙酯
进行如实施例1b中相同的反应,但使用4-氨基间苯二酚代替2-氨基苯酚。不用色谱分析,将未经处理的物质从丙烯腈、己烷和CH2ClC2中重结晶三次以得到12%的黄色晶体。熔点153-55℃。UV(CH2Cl2)346nm(E=851);MS:381(M+,100%)、336、307、291、263、235。
测定该产物在Crodamol DA中的溶解度=1.6%。用Heraeus的150WHg灯以高稀释度辐照该产物,并表现出是光稳定的。
实施例7 2-(4-[6-{2-乙基-己氧基}-苯并噁唑-2-基]-亚苄基)-丙二酸二乙酯
向装有回流冷凝器和带有磁力搅拌器的油浴的50ml三颈反应烧瓶中装入10ml 1-甲基-2-吡咯烷酮中的0.5g无水Na2CO3、0.7g 2-(4-[6-羟基-苯并噁唑-2-基]-亚苄基)-丙二酸二乙酯(实施例6中所描述的)和0.34ml 2-乙基-己基-1-溴。加入各自微量的KJ和四丁基硫酸铵。在100℃下20小时后,在薄层色谱上看不到起始物质。用醋酸乙酯稀释该反应混合物,并用1n NaOH、水和NaCl溶液清洗,用Na2SO4干燥并浓缩。然后在己烷/醋酸乙酯(9∶1-1∶1,v/v)中对其进行色谱分析,并提供300mg浅黄色晶体。熔点50-52℃;UV(乙醇)352nm(E=695);MS:493(M+)、381(100%)、307、235。
测定该产物在Cétiol LC(椰油基辛酸酯癸酸酯)中的溶解度=10.2%。用Heraeus的150W Hg灯以高稀释对辐照该产物,并表现出是光稳定的。
实施例8 2-(4-{6-[2-(2-乙氧基-乙氧基)-乙氧基]-苯并噁唑-2-基}-亚苄基)-丙二酸二乙酯
进行与实施例7中相同的反应,但是用2-(2-乙氧基-乙氧基)-乙氧基-甲基磺酸酯代替2-乙基-己基-1-溴。处理后,用己烷/二乙醚(9∶1-1∶1,v/v)对该产物进行色谱分析以得到黄色的油状物,其仅在两个月后结晶。熔点43-45℃;UV(CH2Cl2)341nm(E=551);MS:497(M+,100%)、452、381。
测定该产物在Cétiol LC中的溶解度=4.6%。用Heraeus的150W Hg灯以高稀释度辐照该产物,并表现出是光稳定的。
实施例9 2-(4-{6-[2-(甲基-双(三甲基-甲硅氧基)-甲硅烷基)-丙-2-烯基氧基]-苯并噁唑-2-基}-亚苄基)-丙二酸二乙酯
a)2-(4-[6-{2-炔丙氧基}-苯并噁唑-2-基]-亚苄基)-丙二酸二乙酯
进行与实施例7中相同的反应,但是用炔丙基溴代替2-乙基-己基-1-溴。处理后,用己烷/醋酸乙酯(9∶1-1∶1,v/v)对该产物进行色谱分析以得到黄色晶体。熔点105-107℃;UV(CH2Cl2)345nm(E=875);MS:419(M+)、380(100%)、374、306、234。
b)2-(4-{6-[2-(甲基-双(三甲基甲硅烷基氧基)-甲硅烷基)-丙-2-烯基氧基]-苯并噁唑-2-基}-亚苄基)-丙二酸二乙酯(氢化硅烷化反应)
在氮气氛下将5ml甲苯中的催化量的二乙烯基-四甲基二硅氧烷铂配合物、200mg 2-(4-[6-{2-炔丙氧基}-苯并噁唑-2-基]-亚苄基)-丙二酸二乙酯(上文实施例9a)和125mg 1,1,1,3,5,5,5-七甲基三硅氧烷置于三颈反应烧瓶中,在80℃下搅拌20小时,然后回流2天。用水/甲醇混合物(1∶10,v/v)清洗该产物溶液并浓缩。在己烷/醋酸乙酯(9∶1,v/v)中对该产物进行色谱分析以得到蜜状液体。UV 348nm(E=535)。NMR表明邻位和孪位的氢化硅烷化产物的混合物=1.3。其在上文所测试的化妆品溶剂中具有无限溶解度和在高稀释度下具有出色的光稳定性。
实施例10 统计学上对应于下式的聚硅氧烷:
在惰性气氛下将10ml二甲苯中5%碳上催化量的铂、200mg 2-(4-[6-{2-炔丙氧基}-苯并噁唑-2-基]-亚苄基)-丙二酸二乙酯(上文实施例9a)和530mg Wacker-Chemie GmbH的聚硅氧烷Ae-151置于三颈反应烧瓶中,并加热5天到120℃。将该产物溶液通过Cellite过滤,用水/甲醇的混合物(1∶10,v/v)清洗并浓缩以得到褐色的油状物。UV 348nm(E=207),在Cétiol LC和Crodamol DA中具有无限的溶解度和在高稀释度下具有出色的光稳定性。
实施例11 O/W防晒液UV-B和UV-A的制备:
含有2%实施例1的化合物的宽光谱防晒液。
配方% 化合物 化学名称
A部分
2 PARSOL MCX 甲氧基肉桂酸乙基己酯
2 实施例1的产物
3 PARSOL 1789 4-叔丁基-4′-甲氧基-二苯甲酰基-甲烷
12 Cétiol LC 椰油基辛酸酯癸酸酯
4 Dermol 185 新戊酸异硬脂基酯
0.25 PEG-2-硬脂酸酯 单硬脂酸二甘醇酯
1 鲸蜡醇 鲸蜡醇
0.25 MPOB/PPOB 甲基-丙基对羟基苯甲酸酯
0.1 EDTA BD EDTA-钠盐
1 Amphisol DEA(Givaudan) 二乙醇胺十六烷基磷酸酯
部分B
0.2 Permulene TR-1 丙烯酸酯C10-C30烷基丙烯酸酯
68.4 去离子水
5 丙二醇 1,2-丙二醇
0.8 KOH(10%) 氢氧化钾
在反应器中将A部分加热到85℃。
在10分钟内缓慢加入B部分,接着加入KOH,冷却该乳液并对其脱气。
实施例12 制备保护性能强的防晒乳
成分
INCI命名
%w/w
A)
PARSOL SLX 聚二甲基硅烷醇二乙基亚苄基 6.00
丙二酸酯
实施例10的产物 6.00
Parsol 5000 4-甲基亚苄基樟脑 4.00
Parsol MCX 甲氧基肉桂酸乙基己酯 6.00
Uvinul T 150 2.00
Silicone DC200/350 cs 聚二甲基硅氧烷 1.00
Lanette O 鲸蜡醇 2.00
Softisan 100 氢化的椰油-甘油酯 3.00
Tegosoft TN 苯甲酸C12-15烷基酯 6.00
Cetiol B 己二酸二丁酯 7.00
Vitamin E acetate 醋酸生育基酯 2.00
Berkemyol(Grape seed) 棕榈酰基葡萄种子提取物 1.00
BHT BHT 0.05
Edeta BD 二钠EDTA 0.10
Phenonip 苯氧基乙醇、对羟基苯甲酸甲 0.60
酯、对羟苯甲酸乙酯、对羟苯甲
酸丙酯和对羟苯甲酸丁酯
AMPHISOL K 鲸蜡基磷酸钾 2.00
B)
去离子水 44.45
Propylen Glycol 丙二醇 5.00
Carbopol 980 卡波姆 0.30
C)
KOH(10%sol.) 氢氧化钾 1.50
Claims (19)
2.根据权利要求1的化合物,其中X为O。
3.根据权利要求1或2的化合物,其中R1和R2为氢。
4.根据权利要求1-3中任一项的化合物,其中R3为氰基和R4为-COOR5。
5.根据权利要求4的化合物,其中所述化合物为:
2-氰基-3-{4-[5-叔丁基-苯并噁唑-2-基]-苯基}-丙烯酸2-乙基己酯或者
2-氰基-3-{4-苯并噁唑-2-基-苯基}-丙烯酸2-乙基己酯。
6.根据权利要求1-3中任一项的化合物,其中R3和R4相互独立地为-COOR5。
7.根据权利要求6的化合物,其中所述化合物为:
2-(4-苯并噁唑-2-基-亚苄基)-丙二酸二乙酯;
2-(4-苯并噁唑-2-基-亚苄基)-丙二酸二丁酯;
3-{4-苯并噁唑-2-基-苯基}-2-丙酰基-丙烯酸2-乙基己酯;
2-(4-[6-羟基-苯并噁唑-2-基]-亚苄基)-丙二酸二乙酯;
2-(4-[6-{2-乙基-己氧基}-苯并噁唑-2-基]-亚苄基)-丙二酸二乙酯;或者
2-(4-{6-[2-(2-乙氧基-乙氧基)-乙氧基]-苯并噁唑-2-基}-亚苄基)-丙二酸二乙酯。
9.根据权利要求8的聚硅氧烷,其中q为2-100的整数。
10.根据权利要求8或9的聚硅氧烷,其中比值(B1+B2+B3+B4)/(B1+B2+B3+B4+B5)为0.01-0.4。
11.根据权利要求10的聚硅氧烷,其中所述聚硅氧烷为
12.根据权利要求1-11中任一项的化合物作为UV-A防晒剂的用途。
13.根据权利要求12的化合物的用途,其中所述用途在于保护人体皮肤或人的毛发。
14.根据权利要求12的化合物的用途,其中所述用途在于保护对UV辐射敏感的塑料材料和医用制品。
15.一种组合物,其包含一种或多种权利要求1-11中任一项的化合物和至少一种药学和/或化妆品可接受的赋形剂。
16.根据权利要求15的组合物,其中权利要求1-11中任一项的化合物存在的量为所述组合物总量的0.5-20wt%。
17.根据权利要求16的组合物,其中权利要求1-11中任一项的化合物存在的量为所述组合物总量的0.5-12wt%。
18.根据权利要求15、16或17的组合物,其中所述组合物为局部组合物。
19.尤其参照实施例的主要如上文所述的发明。
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EP2355791B1 (en) * | 2008-11-13 | 2016-09-28 | Basf Se | Benzylidene compounds comprising phosphono-groups |
KR102487937B1 (ko) | 2014-10-17 | 2023-01-13 | 디에스엠 아이피 어셋츠 비.브이. | 10-하이드록시스테아르산을 포함하는 화장품 조성물의 용도 |
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