CN1889920A - 具有uv滤光活性的微胶囊及其制备方法 - Google Patents
具有uv滤光活性的微胶囊及其制备方法 Download PDFInfo
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- CN1889920A CN1889920A CNA2004800361343A CN200480036134A CN1889920A CN 1889920 A CN1889920 A CN 1889920A CN A2004800361343 A CNA2004800361343 A CN A2004800361343A CN 200480036134 A CN200480036134 A CN 200480036134A CN 1889920 A CN1889920 A CN 1889920A
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Abstract
本发明提供一种制备具有UV滤光活性的微胶囊的方法,其中使至少一种具有UV-A和/或UV-B和/或 UV-C滤光活性的可交联发色团和任选的至少一种不具有UV-A和/或UV-B和/或UV-C滤光活性的可交联单体在缺少具有UV-A和/或UV-B和/或UV-C滤光活性的不可交联的发色团的情况下进行交联反应以及通过该方法获得的微胶囊。
Description
本发明涉及基于微胶囊的新UV滤光剂、其制备方法以及它们尤其在防止日光有害影响的制剂中的应用。
在暴露于越来越多的损伤性阳光的人群中,对防晒剂(sunscreenprotecting agent)存在着持续增长的需求。反复的日光照射可以引起被称为光老化皮肤的皮肤改变。光老化皮肤所呈现的临床变化不同于身体上受到防日光保护部位的正常老化的皮肤。皮肤受到大规模日光照射后引起的损伤结果包括皱纹增多、弹性组织变性、色素改变(pigmentary changes)、癌变前及癌性皮肤病损等。
在过去已经开发了许多遮光剂化学品来防止UV-A(320-400nm)和/或UV-B(290-320nm)波长甚至更短波长(UV-C)的有害影响。这些化学品通常单独或彼此结合掺入公知的和广泛使用的化妆品或药物制剂中。
用于遮光组合物中的大多数UV滤光剂(UV filter)为单体化合物,因而存在这类化合物可以穿透皮肤屏障的内在危险,这是非常不期望的。聚硅氧烷型的UV滤光剂可以是直链或者环状,例如在WO 93/04665、WO 94/06404、EP-A 538431、EP-A 392883和EP-A 358584中描述的。这些聚硅氧烷皮肤穿透的危险较低,但有时由于不相容问题难以将这些聚硅氧烷掺入遮光组合物(sunscreen composition)中,不相容问题因与聚硅氧烷共价键接的UV活性发色团而有差别。
目前已知的UV滤光剂存在的其它问题是它们易于相互作用,在一些遮光组合物包含一种以上UV滤光剂的情况下会产生这样的情形:一种或两种UV滤光剂的UV滤光活性(filter activity)在贮存期间或施加至皮肤后降低。人们已经尝试通过将一种UV滤光剂或两种或多种存在于遮光组合物中的UV滤光剂包胶以使贮存期间和施加至皮肤时UV滤光剂的接触减到最小,从而解决该问题。已公开了,随着时间推移,微胶囊释放UV滤光剂,其它的被设计成能持久地包胶UV滤光剂。包胶(Encapsulation)技术描述于,例如FR 2642 329、DE-A 195 37 415、EP-A 509 904、FR 2 726 760和FR 2 687 914以及WO 00/71084、US-A 6,303,149、WO 98/31333、US-A 5,876,699和WO00/72806中。
一些微囊化的UV滤光剂设计成能以控释方式从微胶囊中释放UV滤光剂,以维持遮光组合物中UV滤光剂的恒定浓度。因而,遮光组合物中的活性UV滤光剂还是高活动的单体化合物,其在施加后具有穿透皮肤的内在危险。而且,在这些实施方案中还可能存在UV滤光剂的失活,为了维持遮光组合物中的恒定浓度,微胶囊需要具有高的初始装载量。最后,确保UV滤光剂从微胶囊中控制释放也很难。
在另一实施方案中,微胶囊被设计成应当持久包胶UV滤光剂,这些微胶囊通常是通过溶胶凝胶法来制备的。然而,难以制备不渗漏(leak)UV滤光剂的微胶囊,在实践中已经表明UV滤光剂之间的相互作用可以通过将它们包胶,例如用溶胶凝胶法包胶来减少,但这只能减缓UV滤光剂的失活而不能充分地阻止其失活。
WO 98/31333公开了遮光剂掺杂的溶胶-凝胶物质,其用于保护身体组织及其它表面不受日光辐射。该溶胶-凝胶物质通过用溶胶凝胶法将UV滤光剂发色团包胶来制备。还公开了,用于包胶发色团的单体可以是通式M(R)n(P)m的化合物,其中M为金属或半金属元素,R为可水解的取代基,n为2-6的整数,P为不能聚合的取代基(non-polymerizable substituent)或遮光剂基团(sunscreenning moiety)且m为0-6的整数。因此,该文献认为可使用单体配制微胶囊的基质,单体本身具有遮光活性(没有公开这类单体的任何实例)。然而,这些单体还用于形成将单体发色团包胶的基质,其中发色团与基质物质不是共价键接,并且在该文献中公开的制备微胶囊的各种方法中不能聚合的单体发色团通过溶胶凝胶法包胶。因此WO 98/31333中公开的微胶囊都包含包胶过的发色团,其与基质物质不是化学连接的,显然若在微胶囊内没有包胶发色团,那么提供具有足够遮光活性的微胶囊是不可能的。因此,WO98/31333中公开的微胶囊还显示出上述讨论到的问题。
EP-A 1 205 178和EP-A 1 205 177建议通过固定存在于皮肤用组合物或化妆品组合物中的活性成分或UV滤光剂来降低活性成分如UV滤光剂穿透进入皮肤之内的危险和可能的皮肤损伤或由此产生的过敏性反应。这些文献公开了一种包含无机颜料和基于有机化合物的活性成分的缀合物(conjugate),其中有机化合物通过间隔基团(spacer group)与无机颜料共价键接。这些文献中公开的缀合物因此包含无机颜料和并与这类颜料发色团的表面化学连接。由于有这样的结构,活性成分穿透进入皮肤之内的问题被解决,不过还存在活性成分彼此相互作用的危险,这可导致遮光组合物中的UV滤光活性失活,因为所有的发色团都在无机颜料的表面上。
本发明要解决的问题是提供不显示上述现有技术中的缺点的新UV滤光剂。该UV滤光剂应具有优良的UV滤光活性,容易得到并且与化妆品和皮肤用组合物中的其它常用成分相容。
令人惊奇地发现一种新型UV滤光剂,它以微胶囊的形式存在并可通过下述的方法获得,在该方法中使至少一种具有UV-A和/或UV-B和/或UV-C滤光活性的可交联单体和任选的至少一种不具有UV-A和/或UV-B和/或UV-C滤光活性的可交联单体在缺少具有UV-A和/或UV-B和/或UV-C滤光活性的不可交联的发色团(non-crosslinkable chromophore)的情况下进行交联反应。
与现有技术中的观点(例如WO 98/31333中表达的观点)相反,发现下述微胶囊具有足够UV滤光活性,所述微胶囊只包含与微胶囊聚合物基质共价键接的具有UV滤光活性的发色团,并且不必将没有与聚合物基质物质共价键接但包胶于微胶囊中的其它单体发色团掺入这些微胶囊中。因此,本发明的微胶囊不包含被包胶的具有UV滤光活性的单体发色团,但本发明的微胶囊中存在的所有发色团都与构成基质的聚合物共价键接。
本文中所用的术语“UV滤光活性”包括UV-A、UV-B和UV-C滤光活性,优选UV-A和UV-B滤光活性。假如术语“UV滤光剂”或“UV滤光活性”使用时没有另外的解释,则它指具有UV-A或者UV-B或UV-C滤光活性的化合物或组合物或基团,以及指兼有UV-A和UV-B滤光活性的化合物或组合物或基团或同时具有UV-A、UV-B和UV-C滤光活性的化合物或组合物或基团,以及指兼有UV-B和UV-C滤光活性的化合物或组合物或基团。优选地,术语“UV滤光剂”或“UV滤光活性”用于指具有UV-A或UV-B滤光活性的化合物、组合物或基团,或用于指兼有UV-A和UV-B滤光活性的化合物、组合物或基团。
本发明还涉及制备这类具有UV滤光活性的新微胶囊的方法、包含该微胶囊的遮光组合物以及该微胶囊用于制备遮光组合物的应用。
本发明采用的制备微胶囊的方法是本领域公知的且在过去已经用于制备包胶的UV滤光剂。不过,与现有技术技术相反,按照本发明所有具有UV滤光活性的化合物与构成微胶囊基质的单体共价键接。这种微胶囊形式的新UV滤光剂兼有现有技术的UV滤光剂不能达到的若干优点。尤其是不再存在单体UV滤光剂渗漏导致穿透进入皮肤之内的危险以及过敏性反应或皮肤病。而且,由于大部分具有UV滤光活性的发色团在微胶囊内共价键接并只有少量的具有UV滤光活性的发色团存在微胶囊的表面上,因而没有下述危险:微胶囊的大量UV滤光剂活性部位与不相容的组分(如其它UV滤光活性分子)接触,这可导致UV滤光活性的失活,这也是EP-A1 205 177和EP-A1205178中公开的UV滤光剂存在的问题。
本发明的微胶囊及其制备方法的一个重要特征是:在微胶囊的形成过程中例如在溶胶凝胶法的过程中不存在具有UV滤光活性的单体不可交联的发色团。因此,能确保存在于如此制得的微胶囊中的所有具有UV滤光活性的发色团与微胶囊的聚合物基质都是共价键接。由于与本发明不相关的未反应的可交联发色团可能存在少量杂质,应尽可能避免。优选地,本发明的微胶囊不含任何未反应的具有UV滤光活性的可交联发色团。
具有UV滤光活性的可交联发色团为新化合物,本发明还涉及那些可交联的发色团。
对本发明具有UV滤光活性的可交联发色团的类型没有特别限制。最优选的发色团为式M(R)n(P)m(Q)q的发色团
其中
M为金属或半金属元素(如硅、钛、锌、铝或锆,优选硅),优选地,M为硅
R为具有优选不多于10个碳原子的可水解取代基(如烃氧基化物(alkoxide)、芳氧基化物(aryloxide)、羧酸酯、酰氧基、二酮基(diketonato)、可水解的含氮基团(aza group)或氯),更优选具有不多于10个碳原子的烃氧基化物或酰氧基,尤其是C1-C6烃氧基化物如甲氧基化物或乙氧基化物;
Q为不可水解的基团(non-hydrolysable group),优选具有不多于10个碳原子的烃基,如C1-C6烷基,例如甲基或乙基,
n为整数2或3,优选3,
m为整数1或2,以及q为整数的0或1,以及
n+m+q=4。
P为提供UV滤光活性的分子基团且优选具有通式A-(B)b(C)c(D)d(E)e-,其与M化学键合
其中
A为具有UV-A和/或UV-B滤光活性的发色团且-(B)b(C)c(D)d(E)e-为间隔基团,其中
B为具有最多20个、优选1-12个、最优选3-12个碳原子的直链或支链亚烷基
C为O、S或NH
D为CONH-基团
E为具有最多20个、优选1-12个、最优选3-12个碳原子的直链或支链亚烷基或亚烯基,以及
b为0或1,
c为0或1,
d为0或1,以及
e为0或1。
优选地,M为硅,R具有不多于10个碳原子,且为烃氧基化物、芳氧基化物或酰氧基,更优选具有不多于10个碳原子的烃氧基化物或酰氧基,尤其是C1-C6烃氧基化物如甲氧基化物或以氧化物,n为整数2或3,尤其是3,P为具有UV-A和/或UV-B滤光活性的残基A,它通常经间隔基团与M化学键合(P为A和间隔基团的结合),m为1。间隔基团优选具有1-10个碳原子,任选地具有1-3个杂原子如氮或氧原子,优选为如上定义的式-(B)b(C)c(D)d(E)e-。
具有UV滤光活性的可交联发色团的制备在了解了本发明说明书的本领域普通技术人员的知识范围内,一些优选的实例通常为下列的公开:
在上述方案中,残基A为提供UV滤光活性的残基P的一部分,残基P通常由残基A和任选的间隔基团构成,所述间隔基团用于将残基A与金属或半金属M结合,尤其与硅结合,符号o为0-6,优选0、1、2或3。
在上述方案中,已经示例了本发明的优选实施方案,其中残基M为硅,所有的残基R为氯或乙氧基化物。特别优选的实施方案中n为3且m为1。当然,该方法也适用于其它实施方案,尤其适用于其它的烃氧基化物。
残基A是优选的已知紫外光吸收剂,这类已知的紫外光吸收剂优选由官能化的硅烷(functional silane)改性,所述硅烷例如甲基二氯甲硅烷、三氯甲硅烷、三乙氧基甲硅烷、3-(异氰酸根合丙基)三乙氧基甲硅烷或3-(氯丙基)-三乙氧基甲硅烷或3-(氨丙基)-三乙氧基甲硅烷,但不限于这些,例如改性的方式包括:
-烯丙基或炔丙基封端的分子A和三乙氧基甲硅烷、甲基二氯甲硅烷(MDClS)或三氯甲硅烷(TClS)之间的氢化硅烷化。该偶合反应结果形成C-Si硅键;
-将羟基或氨基封端的分子A加成至3-(异氰酸基丙基)三乙氧基甲硅烷(ICPTEOS)上,形成氨基甲酸酯或尿烷连接(urethane link);
-利用3-(氨丙基)-三乙氧基甲硅烷(APTEOS)对酰基氯封端的分子M进行酰胺化。
-用伯胺或仲胺(其中胺可为杂环成员)进行氯的亲核取代,如3-(氯丙基)-三乙氧基甲硅烷(CPTEOS)。
与微胶囊共价键接的紫外光吸收剂部分(absorber moiety)A包括吸收波长范围在400-320nm(UVA)和320-290(UVB)或者甚至更短波长(UVC)的光且是化学品UV滤光剂或可以用作化学品UV滤光剂的所有基团。例如这些基团为例如,属于丙烯酸酯类、对氨基苯甲酸酯类、樟脑衍生物(如苯亚甲基樟脑型衍生物(benzylidene camphor type))、肉桂酸酯类、二苯甲酮类、亚苄基丙二酸酯类(esters ofbenzalmalonic acid)、2-(4-乙氧基苯胺基亚甲基)丙二酸酯类(esters of 2-(4-ethoxy anilinomethylene)propandioic)、咪唑衍生物、水杨酸酯类、三嗪酮衍生物、三唑衍生物、二苯甲酰基甲烷类、氨基取代的羟基二苯甲酮类、苯基-苯并咪唑类、氨基苯甲酸酯类(anthranilates)、苯基-苯并唑类、1,4-二氢吡喃化合物的残基以及其它代表现有技术且本领域的技术人员已经知道具有高活性的化合物残基。
丙烯酸酯类的实例包括2-氰基-3,3-二苯基丙烯酸2-乙基己基酯(氰双苯丙烯酸辛酯,PARSOL340)和2-氰基-3,3-二苯基丙烯酸乙酯;
对氨基苯甲酸酯类的实例包括4-氨基苯甲酸、4-氨基苯甲酸-2,3-二羟基丙基酯、4-(双(2-羟丙基)氨基)苯甲酸乙酯、4-(二甲氨基)苯甲酸-2-乙基己基酯(例如Eusolex6007)以及乙氧基化4-氨基苯甲酸乙酯(例如UvinulP25)。
樟脑衍生物的实例包括4-甲基苯亚甲基樟脑(PARSOL5000)、3-苯亚甲基樟脑、樟脑苯甲烃铵甲基硫酸盐(camphor benzalkonium methosulfate)、多丙烯酰氨基甲基苯亚甲基樟脑、磺基苯亚甲基樟脑、磺基甲基苯亚甲基樟脑以及对苯二亚甲基二樟脑磺酸(therephthalidene dicamphor sulfonic acid);
肉桂酸酯的实例包括甲氧基肉桂酸辛酯(PARSOLMCX)、甲氧基肉桂酸乙氧乙酯、二乙醇胺甲氧基肉桂酸酯(PARSOLHydro)以及甲氧基肉桂酸异戊酯。
二苯甲酮类的实例包括二苯甲酮-3、二苯甲酮-4、2,2′,4,4′-四羟基-二苯甲酮以及2,2′-二羟基-4,4′-二甲氧二苯甲酮;
亚苄基丙二酸酯类的实例包括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)丙二酸酯类的实例包括欧洲专利公布EP 0895776中描述的2-(4-乙氧基苯胺基亚甲基)丙二酸二乙酯;
咪唑衍生物的实例包括2-苯基苯并咪唑磺酸及其盐(PARSOLHS)。例如2-苯基苯并咪唑磺酸的盐有碱金属盐如钠盐或钾盐、铵盐、吗啉盐、伯胺、仲胺和叔胺的盐如单乙醇胺盐和二乙醇胺盐。;
水杨酸酯衍生物的实例包括水杨酸异丙基苄酯、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三甲环己酯(homomenthyl salicylate)(胡莫柳酯,HELIOPAN);
三嗪酮衍生物的实例包括辛基三嗪酮(UVINUL T-150)、二辛基丁酰氨基三嗪酮(UVASORB HEB)。
三唑衍生物的实例包括苯并三唑类如2-(2-羟基-5-甲基苯基)苯并三唑、2,2′-亚甲基-双-(6-(2H-苯并三唑-2-基)-4-(1,1,3,3,-四甲基丁基)-苯酚(TINOSORB M)以及EP-A-893119中描述的三唑类
二苯甲酰基甲烷衍生物的实例包括诸如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以及异丙基二苯甲酰基甲烷的化合物;
氨基取代的羟基二苯甲酮的实例包括诸如欧洲专利公布EP 1046391中描述的2-(4-二乙氨基-2-羟基-苯甲酰基)-苯甲酸己酯的化合物。
优选的残基A是
二笨甲酮衍生物如
对氨基苯甲酸衍生物如
苯并唑衍生物如
樟脑衍生物如
肉桂酸或亚苄基丙二酸酯衍生物如
苯并咪唑衍生物如
氰双苯丙烯酸酯衍生物如
苯并三唑衍生物如
二氢吡啶衍生物如
叔丁基二苯甲酰基甲烷衍生物如
其中R’为氢、羟基、直链或支链C1-20-烷基、直链或支链C1-20-烷氧基或C2-20-链烯基。
优选地,具有UV滤光活性的可交联发色团可通过使硅烷分子例如式Si(R)r(Q)qS和相应的含发色团的分子反应获得,在Si(R)r(Q)qS中R为如上定义的可水解的基团,尤其是具有10个或小于10个碳原子的烷氧基或酰氧基,Q为如上定义的不能水解的基团,尤其是C1-C6烷基,例如甲基,S为能够与发色团反应的反应性基团,尤其是氢原子、基团-(CH2)o-NCO、基团-(CH2)o-Cl或基团-(CH2)o-NH2,r为2或3,q为0或1以及o为1-6,如
其中Alk为C1-C6烷基,优选甲基或乙基,
所述发色团选自例如
其中R′为氢、羟基、直链或支链C1-20-烷基、直链或支链C1-20-烷氧基或C2-20-链烯基,但不限于这些。
还可以通过使一种或多种可水解的金属或半金属化合物(尤其是上述的硅烷化合物)互相聚合或与其它单体(如下面定义的没有UV滤光活性的可交联单体)聚合来制备可交联发色团。在这种情况下,可交联的发色团为包含一个或多个UV滤光活性的基团A的低聚物。通常这种低聚物由50个或小于50个单体单元构成,优选由20个单体单元或更少单体单元构成,更优选由10个或更少单体单元构成。优选这样一种低聚物可交联发色团包含5个或更少UV滤光活性基团A,更优选包含3个或更少UV滤光活性基团A,最优选包含1个UV滤光活性基团A。
具有UV滤光活性的可交联发色团自身可进行交联反应,或者它们可在不具有UV滤光活性的可交联单体的存在下进行交联反应。优选地,具有UV滤光活性的可交联发色团与没有UV滤光活性的可交联单体进行交联反应,因为这样容易调节最终的微胶囊中UV滤光活性基团的量。或者,还可以通过如上所述使具有UV滤光活性的单体和没有UV滤光活性的单体制得的低聚物交联,来调节最终微胶囊中UV滤光活性基团的量。
没有UV滤光活性的可交联单体优选为式M(R)n(Q)q化合物,其中M为金属或半金属元素如硅、钛、锌、铝或锆,优选硅,R为如上定义的可水解取代基,优选不多于10个碳原子,如烃氧基化物、芳氧基化物、羧酸酯、酰氧基、二酮基、可水解的含氮基团或氯原子,优选为烃氧基化物、芳氧基化物或酰氧基,更优选具有10个或小于10个碳原子的烃氧基化物或芳氧基,尤其是C1-C6烃氧基化物,最优选甲氧基化物或乙氧基化物,n为2-4的整数,优选3或4,最优选4。Q如上定义且q为0或1,n+q=4。
尤其优选的是诸如四乙氧基甲硅烷(TEOS)、四甲氧基甲硅烷(TEMOS)、甲基三乙氧甲硅烷(METEOS)或其部分水解的和/或部分缩合的聚合物(低聚物)或上述物质的混合物的可交联单体。适宜的可交联单体还公开于,例如EP-A 216 278、以及下文中所列的其它文献中,这些文献公开了溶胶凝胶法的细节,引入本文作为参考。
尽管对制备本发明微胶囊的方法没有特别的限制,原则上对技术人员来说所有熟知的方法都可以运用,但优选通过溶胶凝胶法制备微胶囊,尤其当可交联单体为如上定义的金属的或半金属化合物时。用于制备微胶囊的溶胶凝胶法为本领域普通技术人员所公知。在溶胶-凝胶法中,在高剪切力下,在水中乳化可交联单体、优选如上定义的有和没有UV滤光活性的硅烷,所述水溶液含有助于使乳化液稳定的表面活性剂(如十六烷基三甲基氯化铵等)和/或保护性胶体(如PVP(聚乙烯吡咯烷酮)、PVA(聚乙烯醇)等)。将所获得的乳化液在适当地选择的pH值(碱性、中性或酸性)下与水溶液混合直到球体形成。然后在Si-O-Si键形成期间,使球体交联,例如通过加热或改变pH值进行,并形成三维网络结构。该方法的细节是公知的,例如可参考WO 00/09652和WO 00/72806,其内容在涉及制备微胶囊方法的的范围内引入本文中作为参考。可通过溶胶-凝胶法制备微胶囊的其它方法例如在DE 41 24 588和EP216278中有描述。关于溶胶凝胶法也可以参考例如Colloid Polym.Sci.(2003)281:19-26,DE-A 195 37 415。
关于通过溶胶-凝胶法制备微胶囊的工艺步骤和工艺条件也可以涉及EP-A 216 278、WO 98/31333、US 6,303,149、EP-A 281 034和EP-A 941 761,其中有关溶胶凝胶法的内容引入本文作为参考。特别优选EP-A 216 278和US 6,303,149中公开的方法,其内容引入本文作为参考。特别优选的方法还公开于实施例中。
通过溶胶凝胶法制备本发明的微胶囊有下列好处,即:通过该方法获得的产品已经是混悬液的形式,其中混悬液含约1-80%由0.01-10μm的球体颗粒构成的固体物,其可直接用于本发明的药物组合物中。如果有利的话,也可以将该产品干燥且该产品也可以以干粉的形式使用。
优选地,本发明的微胶囊的粒径为0.01-100μm,更优选为0.01-10μm。微胶囊中UV滤光活性基团的量为10-80%w/w,更优选25-50%w/w。上述百分比涉及UV滤光活性基团A在基质材料中的重量并且是以基质材料的总重量为基准。粒径为平均粒径dv(0.5),除非另有说明。
本发明的微胶囊可包含两种或更多类型的发色团,而不存在发色团基团之间失活的危险,这是因为发色团基团与基质共价键接,因此发色团基团之间接触的危险性低。在本发明具体的优选的实施方案中,一种或两种可交联发色团进行交联反应,尤其是溶胶凝胶法,最优选与至少一种不具有任何UV滤光活性的可交联单体一起进行交联反应。因此,本发明的微胶囊优选包含一种或两种不同上述UV滤光活性基团A;在优选的实施方案中,只包含一种如上定义的发色团基团,其与不具有任何UV滤光活性的可交联单体之比为1∶10至10∶1,更优选7∶3至3∶7,尤其约1∶1。该比值基于重量比重量基准。
本发明的微胶囊可用技术人员熟知的方法掺入遮光组合物内。遮光组合物通常为局部用遮光组合物。
令人惊奇的是,用本发明微胶囊制备的遮光组合物具有优良的防晒因子(sunprotective factor,SPF),它在整个贮存期间或在应用于皮肤之后只轻微地减少,即使存在两种或更多不同的通常相互失活的UV滤光活性组分。
关于局部用遮光组合物的制备,尤其是皮肤和/或化妆品用的制剂如日用化妆品的皮肤防护和遮光制剂的制备,可将载有共价键合的UV滤光剂的微胶囊掺入助剂中,例如通常用于这种制剂的化妆品基质中。在方便的情况下,还可以加入其它常规的UV-A和/或UV-B和/或广谱遮光剂(broad-spectrumscreening agent)。UV遮光剂的组合可以表现出协同效应。载有共价键接的UV滤光剂和其它已知的UV遮光剂的微胶囊的量并不关键。载有共价键接的UV滤光剂的微胶囊的合适的量为约10至约50%重量(取决于微胶囊的有效负载(payload)和体积分数)和约0.5至12%重量的至少一种另外的亲水性和/或亲脂性UV-A或UV-B或广谱遮光剂。这些另外的遮光剂有利地选自下列化合物,但不限于这些:
可考虑用于与本发明的化合物进行组合物的UVB或广谱遮光剂,即吸收峰在约290-340nm之间的物质,其实例包括例如以下的有机和无机化合物:
---丙烯酸酯类如2-氰基-3,3-二苯基丙烯酸2-乙基己基酯(氰双苯丙烯酸辛酯,PARSOL340)、2-氰基-3,3-二苯基丙烯酸乙酯;
---樟脑衍生物如4-甲基苯亚甲基樟脑(PARSOL5000)、3-苯亚甲基樟脑、樟脑苯甲烃铵甲硫酸盐(methosulfate)、多丙烯酰氨基甲基苯亚甲基樟脑、磺基苯亚甲基樟脑、磺基甲基苯亚甲基樟脑、对苯二亚甲基二樟脑磺酸等;
---肉桂酸酯衍生物如甲氧基肉桂酸辛酯(PARSOLMCX)、甲氧基肉桂酸乙氧乙酯、二乙醇胺甲氧基肉桂酸酯(PARSOLHydro)、甲氧基肉桂酸异戊酯等以及与硅氧烷键合的肉桂酸衍生物;
---对氨基苯甲酸衍生物,如对氨基苯甲酸、对二甲氨基苯甲酸2-乙基己基酯、N-氧化丙烯酸化对氨基苯酸乙酯(N-oxypropylenated ethylp-aminobenzoate)、对氨基苯甲酸甘油基酯,
---二苯甲酮类如二苯甲酮-3、二苯甲酮-4、2,2′,4,4′-四羟基-二苯甲酮、2,2′-二羟基-4,4′-二甲氧二苯甲酮等;
---亚苄基丙二酸酯类如4-甲氧基-苯亚甲基丙二酸二(2-乙基己基)酯;
---2-(4-乙氧基-苯胺基亚甲基)丙二酸酯类如欧洲专利公布EP 0 895 776中描述的2-(4-乙氧基-苯胺基亚甲基)丙二酸二乙酯;
---含亚苄基丙二酸酯(benzmalonate)基团的有机硅氧烷化合物,如欧洲专利公布EP 0 358584 B1、EP 0538431 B1和EP 0709080 A1中描述的;
---甲酚曲唑三硅氧烷(Mexoryl XL);
---颜料如微粒化的TiO2等。术语“微粒化的”是指粒径为约5nm至约200nm,特别是约15nm至约100nm。TiO2颗粒也可以涂覆有其它金属氧化物(如氧化铝或氧化锆),或有机涂料(如多元醇、聚甲基硅氧烷(methicone)、硬脂酸铝、烷基硅烷)。这种涂覆是在本技术领域所公知的。
---咪唑衍生物如2-苯基苯并咪唑磺酸及其盐(PARSOLHS)。2-苯基苯并咪唑磺酸的盐例如包括碱金属盐如钠盐或钾盐、铵盐、吗啉盐、伯胺、仲胺、叔胺的盐如单乙醇胺盐、二乙醇胺盐。
---水杨酸酯衍生物如水杨酸异丙基苄基酯、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三甲环己酯(胡莫柳酯,HELIOPAN)等;
---三嗪酮衍生物如辛基三嗪酮(UVINUL T-150)、二辛基丁酰氨基三嗪酮(UVASORB HEB)、双乙氧苯酚甲氧苯基三嗪(Tinosorb S)等。
可考虑用于与本发明的化合物进行组合物的广谱或UVA遮光剂,即吸收峰在约320-400nm之间的物质,其实例为例如以下的有机和无机化合物:
---二苯甲酰基甲烷衍生物如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、二异丙基二苯甲酰基甲烷等;
---苯并三唑衍生物如2,2′-亚甲基-双-(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-双苯并咪唑磺酸或盐如2,2-(1,4-亚苯基)双-(1H-苯并咪唑-4,6-二磺酸)(Neoheliopan AP);
---氨基取代的羟基二苯甲酮如欧洲专利公布EP 1046391中描述的2-(4-二乙氨基-2-羟基-苯甲酰基)-苯甲酸己酯。
---颜料如微粒化的ZnO或TiO2等。术语“微粒化的”是指粒径为约5nm至约200nm,特别是约15nm至约100nm。TiO2颗粒也可以涂覆有其它金属氧化物(如氧化铝或氧化锆),或有机涂料(如多元醇、聚甲基硅氧烷、硬脂酸铝、烷基硅烷)。这种涂覆是在本技术领域所公知的。
由于二苯甲酰基甲烷衍生物具有有限的光稳定性因此使这些UV-A遮光剂光稳定化可能是需要的。因此,术语“常规的UV-A遮光剂”还涉及二苯甲酰基甲烷衍生物如例如PARSOL1789,其由例如下列化合物稳定:
---欧洲专利公布EP 0 514 491 B1和EP 0 780 119 A1中描述的3,3-二苯基丙烯酸酯衍生物;
---美国专利5,605,680中描述的苯亚甲基樟脑衍生物;
---含亚苄基丙二酸酯基团的有机硅氧烷,如欧洲专利公布EP 0358584B1、EP 0538431 B1和EP 0709080 A1中描述的。
本发明的组合物也可以含有通常的化妆品助剂及添加剂。载体化合物及通常的助剂及添加剂包括防腐剂/抗氧化剂、脂肪物质/油类、水、有机溶剂、硅酮、增稠剂、软化剂、乳化剂、其它遮光剂、消泡剂、增湿剂、香料、表面活性剂、填料、螯合剂、阴离子性、阳离子性或两性聚合物或其混合物、挥发剂(propellant)、酸化或碱化剂、染料、着色剂、颜料或纳米颜料,特别是那些适合于通过物理遮挡紫外线而提供光防护作用的物质,或通常配入化妆品,特别是用于生产遮光剂/防晒组合物的任何其它成分。该化妆品及皮肤学助剂及添加剂的必要量可以基于预期产品由本领域技术人员进行容易地选择,将在实施例中进行说明,但并不局限于实施例。
额外量的抗氧化剂/防腐剂通常是优选的。根据本发明,可以使用通常配入化妆品时使用的所有已知抗氧化剂。特别优选的是选自以下物质的抗氧化剂:氨基酸(例如,甘氨酸、组氨酸、酪氨酸、色氨酸)及它们的衍生物、咪唑(例如,咪唑丙烯酸)及衍生物、肽如D,L-肌肽、D-肌肽、L-肌肽及衍生物(例如,鹅肌肽)、类胡萝卜素、胡萝卜素(例如,α-胡萝卜素、β-胡萝卜素、番茄红素)及衍生物、绿原酸及衍生物、硫辛酸及衍生物(例如,二氢硫辛酸)、硫代葡萄糖金、丙基硫氧嘧啶及其它硫醇(例如,硫代还蛋白、谷胱甘肽、半胱氨酸、胱氨酸、胱胺及其糖基-、N-乙酰基-、甲基-、乙基-、丙基-、戊基-、丁基-及月桂基-、棕榈酰基-;油基-、y-亚油基-、胆甾醇基-及甘油基酯)及其盐、硫代二丙酸二月桂酯、硫代二丙酸二硬脂酯、硫代二丙酸及其衍生物(酯、醚、肽、脂质、核苷酸、核苷及盐)以及极低的相容性剂量(例如,pmol bisμmol/kg)的磺基肟化合物(如,丁硫氨酸磺基肟(buthioninsulfoximine)、高半胱氨酸磺基肟(homocysteinsulfoximine)、丁硫氨酸砜(buthioninsulfone)、五-、六-、七硫氨酸磺基肟(penta-,hexa-,heptathioninsulfoximine)),另外还有(金属)螯合剂(如,α-羟基脂肪酸、棕榈酸、肌醇六磷酸、乳铁蛋白)、β-羟酸(如,柠檬酸、乳酸、苹果酸)、腐殖酸(huminic acid)、没食子酸、五倍子提取物、胆红素、胆绿素、EDTA、EGTA及其衍生物、不饱和脂肪酸及它们的衍生物(如,γ-亚油酸、亚油酸、油酸)、叶酸及其衍生物、泛醌(ubiquinone)和泛醇(ubiquinol)及它们的衍生物、维生素C及衍生物(如,抗坏血酸棕榈酸酯及抗坏血酸四异棕榈酸酯、抗坏血酸磷酸镁、抗坏血酸磷酸钠、抗坏血酸醋酸盐)、生育酚(tocopherole)及衍生物(如,醋酸维生素E)、天然维生素E、维生素A及衍生物(维生素A-棕榈酸盐及醋酸盐)的混合物,以及苯甲酸松柏醇酯(coniferylbenzoat)、芸香酸(rutininc acid)及衍生物、a-糖芦丁(a-glycosylrutin)、阿魏酸、亚糠基葡萄糖醇(furfurylidenglucitol)、肌肽、丁羟基甲苯、丁羟基苯甲醚、三羟基丁酰苯、脲及其衍生物、甘露糖及衍生物、锌及衍生物(例如,ZnO、ZnSO4)、硒及衍生物(例如,蛋氨酸硒)、均二苯代乙烯及衍生物(例如,氧化二苯代乙烯、反式氧化二苯代乙烯)及所述活性成分的适宜衍生物(盐、酯、醚、糖、核苷酸、核苷、及脂质)。一种或多种防腐剂/抗氧化剂的存在量可以为本发明的组合物总重量的约0.01wt.%至约10wt.%。优选防腐剂/抗氧化剂的存在量为约0.1wt.%至约1wt.%。
组合物中通常还含有表面活性成分,如乳化剂、增溶剂等。乳化剂能使得两种或更多种不混溶成分进行均匀地混合。而且,乳化剂还能稳定组合物。可用于本发明的、用于形成O/W、W/O、O/W/O或W/O/W乳液/微乳液的乳化剂包括在实施例的表中提及的那些种类及脱水山梨醇油酸酯、脱水山梨醇倍半油酸酯、脱水山梨醇异硬脂酸酯、脱水山梨醇三油酸酯、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-6-六蓖麻酸酯(polyglyceryl-6 hexaricinolate)、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(potassium ricinoleate)、椰酸钠(sodiumcocoate)、牛酸钠(sodium tallowate)、蓖麻酸钾、油酸钠及其混合物。其它的适宜乳化剂为磷酸酯及其盐,如磷酸鲸蜡酯(AmphisolA)、二乙醇胺磷酸鲸蜡酯(Amphisol)、鲸蜡基磷酸钾(AmphisolK)、油酸甘油酯磷酸钠、氢化植物甘油酯磷酸酯及其混合物。此外,可以使用一种或多种合成聚合物作为乳化剂。例如,PVP二十烯共聚物、丙烯酸酯/C10-30烷基丙烯酸酯交联共聚物、丙烯酸酯/硬脂醇醚-20甲基丙烯酸酯共聚物、PEG-22/十二烷基二醇共聚物、PEG-45/十二烷基二醇共聚物及它们的混合物。优选的乳化剂为磷酸鲸蜡酯(AmphisolA)、二乙醇胺磷酸鲸蜡酯(Amphisol)、鲸蜡基磷酸钾(AmphisolK)、PVP二十烯共聚物、丙烯酸酯/C10-30烷基丙烯酸酯交联共聚物、PEG-20脱水山梨糖醇异硬脂酸酯、脱水山梨糖醇异硬脂酸酯及其混合物。一种或多种乳化剂的存在总量可以为本发明组合物总重量的约0.01wt.%至约20wt.%。优选使用约0.1wt.%至约10wt.%的乳化剂。
本发明组合物的脂质相可有利地选自:
矿物油及矿物蜡;
油类,如癸酸或辛酸的甘油三酯,优选蓖麻油;
油类或蜡及其它的天然或合成油,在优选实施方案中脂肪酸与醇(例如异丙醇、丙二醇、甘油)的酯,或脂肪醇与碳酸或脂肪酸的酯;
苯甲酸烷基酯;和/或
硅油类,如二甲基聚硅氧烷、二乙基聚硅氧烷、二苯基聚硅氧烷、环甲硅油及其混合物。
可以掺入到本发明的乳液、微乳液、油凝胶(oleo gel)、水分散体、脂质分散体的油相中的典型脂肪物质有利地选自带有3至30个碳原子的饱和和/或不饱、直链或支链烷基羧酸与具有3至30个碳原子的饱和和/或不饱和、直链和/或支链醇的酯,以及芳香族羧酸和具有3-30个碳原子的饱和和/或不饱和的直链或支链醇的酯。这种酯可以有利地选自:棕榈酸辛酯、椰酸辛酯、异硬脂酸辛酯、辛基十二烷基肉豆蔻酸酯、异壬酸鲸蜡硬脂基酯(cetearylisononanoate)、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、油酸油酯、芥酸油酯(oleylerucate)、油酸芥酯(erucyloleate)、芥酸芥酯(erucylerucate)、硬脂酸三癸酯,偏苯三酸三癸酯以及合成酯、半合成酯或这些酯的天然混合物,例如希蒙德木油(jojoba oil)。
适用于本发明组合物的其它脂肪成分包括极性油,如卵磷脂及脂肪酸甘油三酯,即具有8至24个碳原子(优选12至18个碳原子)的饱和和/或不饱和、直链或支链羧酸的三甘油酯,因此脂肪酸甘油三酯优选选自合成油、半合成油或天然油类(例如,椰酸甘油(Cocoglyceride)、橄榄油、葵花油、豆油、花生油、菜籽油、甜杏仁油、棕榈油、椰子油、蓖麻油、氢化蓖麻油、麦油、葡萄籽油、澳洲坚果油等);非极性油,如直链和/或支链链烃及蜡,例如矿物油、凡士林(矿脂);石蜡、角鲨烷及角鲨烯、聚烯烃、氢化聚异丁烯及异十六烷,优选的聚烯烃是聚癸烯;二烷基醚,如二辛基醚(dicaprylyl ether);直链或环状硅油,如优选环甲硅油(八甲基环四硅氧烷;十六烷基二甲硅油(cetyldimethicone)、六甲基环三硅氧烷、聚二甲基硅氧烷、聚(甲基苯基硅氧烷)及其混合物。
可有利地掺入本发明组合物中的其它脂肪成分是异二十烷;二庚酸新戊二醇酯;二辛酸丙二醇酯/二癸酸丙二醇酯;辛酸/癸酸/琥珀酸二甘油酯;辛酸丁二醇酯/癸酸丁二醇酯;C12-13烷基乳酸酯;二C12-13烷基酒石酸酯;甘油三异硬脂酸酯(triisostearin);六辛酸二季戊四醇酯/六癸酸二季戊四醇酯;单异硬酯酸丙二醇酯;甘油三辛酸酯;二甲基异山梨醇。特别有利的是使用C12-15烷基苯甲酸酯与2-乙基己基异硬酯酸酯的混合物、C12-15烷基苯甲酸酯与异三癸基异壬酸酯的混合物、以及C12-15烷基苯甲酸酯、2-乙基己基异硬酯酸酯及异三癸基异壬酸酯的混合物。
本发明组合物中的油相还可以含有天然植物或动物蜡,如蜂蜡、白蜡(china wax)、大蜂蜡及其它昆虫蜡,以及牛油树脂和可可脂。
可以在本发明的组合物中掺入增湿剂以保持皮肤的水化和再水化。那些通过提供防护层来防止水从皮肤蒸发的增湿剂被称为润肤剂(emollient)。另外,润肤剂为皮肤表面提供软化或抚慰作用,通常被认为对局部使用是安全的。优选的润肤剂包括矿物油、羊毛脂、矿脂、癸酸/辛酸三甘油醛、胆固醇、硅酮,如二甲硅油、环甲硅油、杏仁油、希蒙德木油、鳄梨油、蓖麻油、芝麻油、葵花油、椰子油及葡萄籽油、可可脂、橄榄油、芦荟提取物、脂肪酸,如油酸及硬脂酸、脂肪醇,如鲸蜡醇及十六烷醇(ENJAY)、己二酸二异丙酯、羟基苯甲酸酯、C9-15醇的苯甲酸酯、异壬酸异壬酯、醚,如聚氧化丙烯丁基醚及聚氧化丙烯鲸蜡基醚、和C12-15烷基苯甲酸酯,以及它们的混合物。最优选的润肤剂为羟基苯甲酸酯、芦荟油(aloe vera)、C12-15烷基苯甲酸酯及其混合物。润肤剂的存在量为组合物总重量的约1wt.%至约20wt.%。润肤剂的优选量为约2wt.%至约15wt.%,最优选约4wt.%至约10wt.%。
在皮肤表面结合水并从而保持水的增湿剂被称为湿润剂(humectant)。可以在本发明的组合物中引入适宜的润湿剂,如甘油、聚丙二醇、聚乙二醇、乳酸、吡咯烷酮羧酸、脲、磷脂、胶原蛋白、弹性蛋白、神经酰胺、卵磷脂山梨糖醇、PEG-4及其混合物。其它的适宜增湿剂是以下的聚合物增湿剂:水溶性和/或可溶胀和/或具有水凝胶化多糖的聚合物增湿剂,如透明质酸、壳聚糖和/或富岩藻糖的多糖,例如可以作为Fucogel1000(CAS-Nr.178463-23-5)从SOLABIA S获得。在本发明的组合物中,可任选地按以下量存在一种或多种润湿剂:约0.5wt.%至约8wt.%,优选约1wt.%至约5wt.%。
本发明组合物中水相可以含有通常的化妆品添加剂,如醇,特别是低级醇,优选乙醇和/或异丙醇,低级二醇或多元醇及它们的醚,优选丙二醇、甘油、乙二醇、乙二醇单乙基醚或乙二醇单丁基醚、丙二醇单甲基醚或丙二醇单乙基醚或丙二醇单丁基醚、二甘醇单甲基醚或二甘醇单乙基醚及类似产品、聚合物、泡沫稳定剂;电解质,特别是一种或多种增稠剂。可用于本发明组合物中促进产品的稠度的适宜增稠剂包括卡波姆、二氧化硅、硅酸镁和/或硅酸铝、蜂蜡、硬脂酸、硬脂醇多糖及它们的衍生物,如黄原胶、羟丙基纤维素、聚丙烯酰胺、丙烯酸酯交联共聚物(优选卡波姆,如单独的980、981、1382、2984、5984各型号的carbopole及其混合物)。可包括在本发明的组合物中用于中和诸如乳化剂或成泡剂/泡沫稳定剂(foam builder/stabilizer)的成分的适宜中和剂包括但不局限于碱金属氢氧化物,如氢氧化钠及氢氧化钾;有机碱,如二乙醇胺(DEA)、三乙醇胺(TEA)、氨甲基丙醇及其混合物;氨基酸,如精氨酸和赖氨酸,及上述物质的任何组合。在本发明的组合物中,可任选地按以下量存在中和剂:约0.01wt.%至约8wt.%,优选约1wt.%至约5wt.%。
在本发明的组合物中添加电解质对于改变憎水乳化剂的性能可能是必需的。因此,本发明的乳液/微乳液可以优选含有一种或几种电解质盐,包括阴离子,如氯化物、硫酸盐、碳酸盐、硼酸盐及铝酸盐,但并不局限于此。其它的适宜电解质可以是基于有机阴离子的物质,例如但不局限于乳酸盐、醋酸盐、苯甲酸盐、丙酸盐、酒石酸盐及柠檬酸盐。作为阳离子,优选选择铵、烷基铵、碱或碱土金属、镁-、铁-、或锌离子。特别优选的盐是氯化钾及氯化钠、硫酸镁、硫酸锌及其混合物。电解质在组合物中的存在量为约0.01wt.%至约8wt.%。
作为遮光组合物,本发明的化妆品组合物可用作保护人类表皮或毛发免受紫外线照射破坏作用的光防护组合物。特别是可以按下述形态提供这种组合物:洗液、增稠洗液、凝胶、乳膏、乳、软膏、粉末或固体管棒(solid tubestick),并且可以任选地包装为气雾剂,以及以摩丝、泡沫或喷雾剂的形式提供。当本发明的化妆品组合物是用于防护人类表皮免受紫外辐射或作为遮光组合物时,它们可为溶剂或脂肪物质中的悬混液或分散液的形式,或者可采取乳液或微乳液的形态(特别是O/W或W/O型、O/W/O或W/O/W型),如乳膏或乳、泡状分散体,及采取软膏、凝胶、固体管棒或气雾剂摩丝的形态。乳液也可以含有阴离子、非离子、阳离子或两性表面活性剂。
下列实施例用于对本发明的方法和组合物作进一步地说明。这些例子仅为说明性的,绝不是用于对本发明的范围进行限定。
实施例1
a)4-(2-苯并唑基)-苯酚
向配备有与水分离器组合的回流冷凝器和带有磁力搅拌器的油浴的250ml三口反应烧瓶中装入在150ml 1,2-二氯苯中的16.4g(150mmol)的2-氨基苯酚(Fluka)、20.8g(150mmol)的4-羟基苯甲酸和1.2g的硼酸。在回流18小时后,分离出5ml的水。在薄层层析(己烷/乙酸乙酯=3∶2)上没有观察到起始原料。将反应混合物冷却并用己烷稀释。产生晶体,将其滤出、用己烷洗涤并在60℃下真空干燥,得到31.3g(99%)产物。M.p.242-245℃。UV(乙醇)306nm(31′831)。
b)2-(4-烯丙氧基苯基)-苯并唑
向配备有回流冷凝器和带有磁力搅拌器的油浴的500ml圆底烧瓶中装入在300ml的1-甲基-2-吡咯烷酮中的13.94g的上述4-(2-苯并唑基)-苯酚、9.7g的烯丙基溴和17.5g的无水Na2CO3。加入痕量的KJ。在110℃下5h小时后在薄层层析上没有观察到起始原料。将反应混合物用乙酸乙酯稀释并用1N NaOH、水和NaCl溶液洗涤,用Na2SO4干燥、浓缩并由己烯重结晶,得到14.3g(86%)的2-(4-丙-2-烯氧基-苯基)-苯并唑。M.p.95-96℃,UV(乙醇)308nm(26′184)。
c)(4-(3-(三乙氧甲硅烷基)丙氧基])苯基)-苯并唑
在氮气氛下,向配备有回流冷凝器和带有磁力搅拌器的油浴的250ml圆底烧瓶中装入在100ml甲苯中的4.0g(22mmol)三乙氧基甲硅烷和5.0g(20mmol)的上述2-(4-烯丙氧基苯基)-苯并唑。将反应混合物加热至70℃并加入催化量的二乙烯基-四甲基二硅氧烷铂络合物。反应混合物加热2小时后,加入额外的1.8g(11mmol)的三乙氧基甲硅烷并将反应混合物搅拌过夜。将产物溶液蒸发,用甲苯稀释并在硅藻土(Celite)上过滤,得到8g(96%)粗产物(4-(3-(三乙氧甲硅烷基)丙氧基])苯基)-苯并唑。UV(乙醇)308nm(23′468)。
实施例2
(4-(3-(三乙氧甲硅烷基)丙基]氨基]羰基]氧])苯基)-苯并唑
在氮气氛下,向搅拌过的按照实施例1中的描述制备的0.5g(2.4mmol)4-(2-苯并唑基)-苯酚在10ml四氢呋喃和几滴二月桂酸二丁基锡催化剂中的溶液中,加入0.6g(2.52mmol)的ICTEOS。将混合物在30℃下搅拌18h。在除去溶剂后,将产物用己烷沉淀、过滤和干燥得到0.99g(90%)的(4-(3-(三乙氧甲硅烷基)丙基]-氨基]羰基]氧])苯基)-苯并唑。M.p.141-142℃;UV(乙醇)304nm(24′630)。
实施例3
2-[[4-[3-(三甲氧甲硅烷基)丙氧基]苯亚甲基]-丙二酸二乙酯
在氮气氛下,向配备有回流冷凝器和带有磁力搅拌器的油浴的250ml圆底烧瓶中装入在100ml甲苯中的10.0g(82mmol)三甲氧基甲硅烷和5.0g(16.4mmol)的2-[[4-(丙-2-烯氧基)苯亚甲基]-丙二酸二乙酯。将反应混合物加热至70℃并加入催化量的二乙烯基-四甲基二硅氧烷铂络合物。将反应混合物加热2小时后,将溶液浓缩、过滤在硅藻土上过滤得到6.2g(88%)黄色油状粗产物2-[[4-[3-(三甲氧甲硅烷基)丙氧基]苯亚甲基]-丙二酸二乙酯。UV(乙醇)312nm(24′793)。
实施例4
2-[[4-[2-(三甲氧甲硅烷基)-丙-2-烯氧基]苯亚甲基]-丙二酸二乙酯
在氮气氛下,向配备有回流冷凝器和带有磁力搅拌器的油浴的250ml圆底烧瓶中装入在100ml甲苯中的2.2g(18mmol)三甲氧基甲硅烷和5.0g(16.5mmol)丙二酸[[4-(2-丙炔氧基)苯基]亚甲基]二乙酯。将反应混合物加热至70℃并加入催化量的二乙烯基-四甲基二硅氧烷铂络合物。将反应混合物加热2小时后,将溶液浓缩并在硅藻土上过滤得到7.1g(100%)黄色油状物2-[[4-[2-(三甲氧甲硅烷基)-丙-2-烯氧基]苯亚甲基]-丙二酸二乙酯。UV(乙醇)312nm(24′623)。
实施例5
2-[[4-[2-(三乙氧甲硅烷基)-丙-2-烯氧基]苯亚甲基]-丙二酸二乙酯
在氮气氛下,向配备有回流冷凝器和带有磁力搅拌器的油浴的1000ml圆底烧瓶中装入在500ml甲苯中的72g(0.44mol)三乙氧基甲硅烷和120g(0.4mmol)丙二酸[[4-(2-丙炔氧基)苯基]亚甲基]二乙酯。将反应混合物加热至70℃并加入催化量的二乙烯基-四甲基二硅氧烷铂络合物。反应混合物加热20小时后,加入额外的6.6g(0.04mol)的三乙氧基甲硅烷并将混合物再搅拌4h。然后,将该溶液浓缩、溶于二氯甲烷中并用水洗两次。经Na2SO4干燥后,将有机相浓缩并通过柱色谱纯化(己烷/EtOAc),得到35.4g(19%)黄色油状物2-[[4-[2-(三乙氧甲硅烷基)-丙-2-烯氧基]苯亚甲基]-丙二酸二乙酯。UV(乙醇)314nm(23′926)。
实施例6
将1.5g按照实施例5中的描述制备的2-[[4-[2-(三乙氧甲硅烷基)-丙-2-烯氧基]苯亚甲基]-丙二酸二乙酯溶于7.5g四乙氧基甲硅烷中。使用Ultra Tourrax T-25basic,以17500rpm的转速在高剪切力下将有机相乳化在50g含1%十六烷基三甲基氯化铵(CETAC)的水溶液中。然后将该乳液在60℃下倾入装有50g pH11的NaOH水溶液的250ml圆底烧瓶中并搅拌3天。最终的混悬液含载有20%w/w发色团的微胶囊,微胶囊的粒径dv(0.5)=5μm。将得到的粉末掺入实施例7中描述的乳液中,在实验条件下的SPF值为5。
实施例7--W/O型遮光乳液
% | ||
A) | Brij 721 | 2.00 |
Brij 72 | 2.00 | |
鲸蜡醇 | 2.00 | |
硬脂醇(Lanette 18) | 1.00 | |
Lanette 22 | 1.00 | |
Myritol 318 | 11.20 | |
Tegosoft TN | 2.00 | |
Arlamol HD(异十六烷) | 3.00 | |
BHT | 0.05 |
Phenonip | 1.00 | |
B) | 水 | 58.50 |
甘油 | 5.00 | |
Edeta BD | 0.10 | |
C) | KOH 10% | 0.15 |
D) | Sepigel 305 | 1.00 |
E) | 实施例6的微胶囊 | 10.00 |
100.00 |
分别将A)和B)部分加热至85℃,同时搅拌。在搅拌下将B)部分加入到A)部分中。冷却至约45℃,同时搅拌;然后加入C)部分。在40℃下加入D)部分。冷却至环境温度,同时搅拌。加入E)部分。再次匀化以获得小的粒径。
实施例8--O/W型含颜料的防晒乳(sun milk)
成分 | INCI名称 | %w/w | |
A) | PARSOL SLX | 聚硅酮-15 | 6.00 |
Neo Heliopan AP | 3.00 | ||
Tinosorb S | 氢化椰酸甘油 | 3.00 | |
Lanette O | 鲸蜡硬脂醇(Cetearyl Alcohol) | 2.00 | |
Myritol 318 | 辛酸/癸酸甘油三酯 | 6.00 | |
矿物油 | 矿物油 | 2.00 | |
维生素E醋酸酯 | 醋酸生育酚 | 1.00 | |
Prisorine 3515 | 异硬脂醇 | 4.00 | |
B) | Edeta BD | EDTA二钠 | 0.10 |
Phenonip | 苯氧乙醇 & 对羟基苯甲酸甲酯 & 对羟基苯甲酸乙酯 & 对羟基苯甲酸丙酯 & 对羟基苯甲酸丁酯 | 0.60 | |
Amphisol K | 鲸蜡基磷酸钾 | 2.00 | |
去离子水 | 水 | 至100 | |
1,2-丙二醇 | 丙二醇 | 5.00 | |
Carbopol 981 | 卡波姆 | 0.30 | |
Tinosorb M | 亚甲基双-苯并三唑基四甲基丁基苯酚 | 6.00 | |
10%KOH溶液 | 氢氧化钾 | 2.10 | |
C) | 本发明的微胶囊 | 1-50% |
步骤:
将A)和B)部分加热至85℃,同时搅拌。均匀后,在搅拌下将B)部分加入到A)部分中。冷却至环境温度,同时搅拌,加入C)部分。匀化以获得小的粒径。
实施例9--防水性防晒乳
成分 | INCI名称 | %w/w | |
A) | PARSOL SLX | 聚硅酮-15 | 6.00 |
PARSOL 1789 | 丁基甲氧基二苯甲酰基甲烷 | 2.00 | |
PARSOL 5000 | 4-甲基苯亚甲基樟脑 | 4.00 | |
Uvinul T 150 | 乙基己基三嗪酮 | 2.00 | |
硅酮DC 200/350cs | 二甲硅油 | 1.00 | |
Lanette O | 鲸蜡硬脂醇 | 2.00 | |
Softisan 100 | 氢化的椰油基(Coco)-甘油酯 | 3.00 | |
Tegosoft TN | C12-15烷基苯甲酸酯 | 6.00 | |
Cetiol B | 己二酸二丁酯 | 7.00 | |
维生素E醋酸酯 | 醋酸生育酚 | 2.00 | |
BHT | BHT | 0.05 | |
Edeta BD | EDTA二钠 | 0.10 | |
Phenonip | 苯氧乙醇 & 对羟基苯甲酸甲酯 & 对羟基苯甲酸乙酯 & 对羟基苯甲酸丙酯 & 对羟基苯甲酸丁酯 | 0.60 | |
Amphisol | 鲸蜡基磷酸DEA | 2.00 | |
B) | 去离子水 | 水 | 至100 |
丙二醇 | 丙二醇 | 5.00 | |
Carbopol 980 | 卡波姆 | 0.30 | |
KOH(10%sol.) | 氢氧化钾 | 1.50 | |
C) | 本发明的微胶囊 | 1-50% |
步骤:
将A)和B)部分加热至85℃,同时搅拌。均匀后,在搅拌下将B)部分加入到A)部分中。冷却至环境温度,同时搅拌,加入C)部分。匀化以获得小的粒径。
实施例10--用于婴儿和儿童的防晒乳
成分 | INCI名称 | %w/w | |
A) | 二氧化钛 | 二氧化钛细粉(microfine) | 4.00 |
Tegosoft TN | C12-15烷基苯甲酸酯 | 5.00 | |
硅酮2503化妆蜡 | 十八烷基二甲硅油 | 2.00 |
鲸蜡醇 | 鲸蜡醇 | 1.00 | |
丁基化羟基甲苯 | BHT | 0.05 | |
Estol GMM 3650 | 豆蔻酸甘油酯 | 4.00 | |
Edeta BD | EDTA二钠 | 0.10 | |
Phenonip | 苯氧乙醇 & 对羟基苯甲酸甲酯 & 对羟基苯甲酸乙酯 & 对羟基苯甲酸丙酯 & 对羟基苯甲酸丁酯 | 0.60 | |
Amphisol A | 鲸蜡基磷酸酯 | 2.00 | |
B) | 去离子水 | 水 | 至100 |
Carbopol 980 | 卡波姆 | 0.6 | |
甘油 | 甘油 | 3.00 | |
10%KOH溶液 | 氢氧化钾 | 2.4 | |
C) | 本发明的微胶囊 | 1-50% |
步骤:
将A)和B)部分加热至85℃,同时搅拌。均匀后,在搅拌下将B)部分加入到A)部分中。冷却至环境温度,同时搅拌,加入C)部分。匀化以获得小的粒径。
实施例11--高保护性防晒乳
成分 | INCI名称 | %w/w | |
A ) | PARSOL SLX | 聚硅酮-15 | 6.00 |
PARSOL 1789 | 丁基甲氧基二苯甲酰基甲烷 | 2.00 | |
PARSOL 5000 | 4-甲基苯亚甲基樟脑 | 4.00 | |
Uvinul T 150 | 2.00 | ||
硅酮DC 200/350cs | 二甲硅油 | 1.00 | |
Lanette O | 鲸蜡硬脂醇 | 2.00 | |
Softisan 100 | 氢化椰酸甘油 | 3.00 | |
Tegosoft TN | C12-15烷基苯甲酸酯 | 6.00 | |
Cetiol B | 己二酸二丁酯 | 7.00 | |
维生素E醋酸酯 | 醋酸生育酚 | 2.00 | |
BHT | BHT | 0.05 | |
Edeta BD | EDTA二钠 | 0.10 | |
Phenonip | 苯氧乙醇 & 对羟基苯甲酸甲酯 & 对羟基苯甲酸乙酯 & 对羟基苯甲酸丙酯 & 对羟基苯甲酸丁酯 | 0.60 | |
Amphisol K | 鲸蜡基磷酸钾 | 2.00 |
B) | 去离子水 | 水 | 至100 |
丙二醇 | 丙二醇 | 5.00 | |
Carbopol 980 | 卡波姆 | 0.30 | |
KOH(10%的溶液) | 氢氧化钾 | 1.50 | |
C) | 本发明的微胶囊 | 1-50% | |
D) | 香料 | 香料 | 适量 |
步骤:
将A)和B)部分加热至85℃,同时搅拌。均匀后,在搅拌下将B)部分加入到A)部分中。冷却至环境温度,同时搅拌,加入C)和D)部分。匀化以获得小的粒径。
实施例12--无水防晒凝胶
成分 | INCI名称 | %w/w | |
A) | PARSOL MCX | 甲氧基肉桂酸乙基己基酯 | 6.00 |
PARSOL 1789 | 丁基甲氧基二苯甲酰基甲烷 | 4.00 | |
PARSOL 5000 | 4-甲基苯亚甲基樟脑 | 4.00 | |
Uvasorb HEB | 二乙基己基丁酰氨基三嗪酮 | 1.50 | |
Uvinul A plus | 2.00 | ||
维生素E醋酸酯 | 醋酸生育酚 | 1.50 | |
Tegosoft TN | C12-15烷基苯甲酸酯 | 9.00 | |
Elefac I-205 | 乙基己基十二烷基新戊酸酯 | 2.00 | |
乙醇 | 乙醇 | 至100 | |
异丙醇 | 异丙醇 | 20.00 | |
B) | Klucel MF | 羟丙基纤维素 | 2.00 |
C) | 本发明的微胶囊 | 1-50% | |
D) | 香料 | 适量 |
步骤:
混合A)和B)部分,同时搅拌。均匀后,在搅拌下加入C)和D部分。
实施例13--防晒凝胶
成分 | INCI名称 | %w/w | |
A ) | Pemulen TR-2 | 丙烯酸酯/C10-30烷基丙烯酸酯交联聚合物 | 0.604 |
Phenonip | 苯氧乙醇 & 对羟基苯甲酸甲酯 & 对羟基苯甲酸乙酯& 对羟基苯甲酸丙酯 & 对羟基苯甲酸丁酯 | 0.60 | |
Edeta BD | EDTA二钠 | 0.1 | |
水 | 水 | 至100 | |
B) | PARSOL 1789 | 丁基甲氧基二苯甲酰基甲烷 | 4.00 |
PARSOL 340 | 氰双苯丙烯酸辛酯 | 3.00 | |
Tegosoft TN | C12-15烷基苯甲酸酯 | 15.00 | |
Antaron V-216 | PVP/十六碳烯共聚物 | 1.00 | |
维生素E醋酸酯 | 醋酸生育酚 | 0.50 | |
Uvinul TiO2 | 二氧化钛 | 5.00 | |
丁基化羟基甲苯 | BHT | 0.05 | |
Cremophor RH 410 | PEG-40氢化蓖麻油 | 0.50 | |
Tris Amino | 氨基丁三醇 | 0.50 | |
C) | 本发明的微胶囊 | 1-50% | |
D) | 香料 | 香料 | 适量 |
步骤:
将A)和B)部分加热至85℃,同时搅拌。均匀后,在搅拌下将B)部分加入到A)部分中。冷却至环境温度,同时搅拌,加入C)和D)部分。匀化以获得小的粒径。
实施例14--高保护性WO防晒乳
成分 | INCI名称 | %w/w | |
A) | PARSOL 1789 | 丁基甲氧基二苯甲酰基甲烷 | 2.00 |
PARSOL 5000 | 4-甲基苯亚甲基樟脑 | 4.00 | |
Uvinul T 150 | 乙基己基三嗪酮 | 2.00 | |
Uvinul TiO2 | 二氧化钛和三甲氧辛基甲硅烷 | 5.00 | |
Arlacel P 135 | PEG-30双多羟基硬脂酸酯 | 2.00 | |
Tegosoft TN | C12-15烷基苯甲酸酯 | 5.00 | |
Cosmacol EMI | 二-C12-13烷基苹果酸酯 | 6.00 | |
Miglyol 840 | 丙二醇二辛酸酯/二癸酸酯 | 6.00 | |
丁基化羟基甲苯 | BHT | 0.05 | |
Phenonip | 苯氧乙醇 & 对羟基苯甲酸甲酯 & 对羟基苯甲酸乙酯 & 对羟基苯甲酸丙酯 & 对羟基苯甲酸丁酯 | 0.60 | |
B) | 去离子水 | 水 | 至100 |
甘油 | 甘油 | 5.00 | |
Edeta | EDTA二钠 | 0.1 |
NaCl | 氯化钠 | 0.30 | |
C) | PARSOL HS | 苯基苄咪唑磺酸 | 4.00 |
水 | 水 | 20.00 | |
三乙醇胺99%. | 三乙醇胺 | 2.50 | |
D) | 本发明的微胶囊 | 1-50% | |
E) | 香料 | 适量 |
步骤:
将A)、B)和C)部分加热至85℃,同时搅拌。均匀后,在搅拌下将B)和C)部分加入到A)部分中。冷却至环境温度,同时搅拌,加入D)和E)部分。匀化以获得小的粒径。
实施例15-O/W型含颜料的乳
成分 | INCI名称 | %w/w | |
A) | Cremophor WO 7 | PEG-7氢化蓖麻油 | 6.00 |
Elfacos ST 9 | PEG-45/十二烷二醇共聚物 | 2.00 | |
PARSOL 1789 | 丁基甲氧基二苯甲酰基甲烷 | 3.00 | |
Tinosorb S | 5.00 | ||
PARSOL 5000 | 4-甲基苯亚甲基樟脑 | 4.00 | |
Uvinul TiO2 | 二氧化钛 | 2.00 | |
ZnO细粉 | 氧化锌 | 2.00 | |
微晶蜡 | 微晶蜡 | 2.00 | |
Miglyol 812 | 辛酸/癸酸甘油三酯 | 5.00 | |
维生素E醋酸酯 | 醋酸生育酚 | 1.00 | |
希蒙得木油 | 希蒙得木种子油 | 5.00 | |
Edeta BD | EDTA二钠 | 0.10 | |
丁基化羟基甲苯 | BHT | 0.05 | |
Phenonip | 苯氧乙醇 & 对羟基苯甲酸甲酯 & 对羟基苯甲酸乙酯 & 对羟基苯甲酸丙酯 & 对羟基苯甲酸丁酯 | 0.60 | |
B) | 去离子水 | 水 | 至100 |
甘油 | 甘油 | 5.00 | |
C) | Neo Heliopan AP | 2.00 | |
去离子水 | 水 | 20.00 | |
10%KOH溶液 | 氢氧化钾 | 4.00 | |
D) | 本发明的微胶囊 | 1-50% | |
E) | 香料 | 香料 | 适量 |
步骤:
将A)、B)和C)部分加热至85℃,同时搅拌。均匀后,在搅拌下将B)和C)部分加入到A)部分中。冷却至环境温度,同时搅拌,加入D)和E)部分。匀化以获得小的粒径。
实施例16--保护性含维生素C的日用乳膏
成分 | INCl名称 | %w/w | |
A) | PARSOL SLX | 聚硅酮-15 | 4.00 |
PARSOL 1789 | 丁基甲氧基二苯甲酰基甲烷 | 1.50 | |
豆蔻酸甘油酯 | 豆蔻酸甘油酯 | 2.00 | |
鲸蜡醇 | 鲸蜡醇 | 0.50 | |
Mvritol 318 | 辛酸/癸酸甘油三酯 | 5.00 | |
Crodamol DA | 己二酸二异丙基酯 | 5.00 | |
维生素E醋酸酯 | 醋酸生育酚 | 2.00 | |
丁基化羟基甲苯 | BHT | 0.05 | |
Phenonip | 苯氧乙醇 & 对羟基苯甲酸甲酯 & 对羟基苯甲酸乙酯 & 对羟基苯甲酸丙酯 & 对羟基苯甲酸丁酯 | 0.60 | |
EdetaBD | EDTA二钠 | 0.10 | |
Amphisol K | 鲸蜡基磷酸钾 | 2.00 | |
B) | 去离子水 | 水 | 至100 |
1,2-丙二醇 | 丙二醇 | 2.00 | |
D-泛醇75L | 泛醇 | 2.00 | |
乙醇 | 乙醇 | 5.00 | |
尿囊素 | 尿囊素 | 0.20 | |
Carbopol ETD 2001 | 卡波姆 | 0.30 | |
KOH 10%的溶液 | 氢氧化钾 | 1.50 | |
C) | 水 | 水 | 10.00 |
Stay-C 50 | 抗坏血酸磷酸钠 | 0.50 | |
D) | 本发明的微胶囊 | 1-50% | |
E) | 香料 | 香料 | 适量 |
步骤:
将A)、B)和C)部分加热至85℃,同时搅拌。均匀后,在搅拌下将B)和C)部分加入到A)部分中。冷却至环境温度,同时搅拌,加入D)和E)部分。匀化以获得小的粒径。
Claims (25)
1.制备具有UV滤光活性的微胶囊的方法,其中使至少一种具有UV-A和/或UV-B和/或UV-C滤光活性的可交联发色团和任选的至少一种不具有UV-A和/或UV-B和/或UV-C滤光活性的可交联单体在缺少具有UV-A和/或UV-B和/或UV-C滤光活性的不可交联的发色团的情况下进行交联反应。
2.权利要求1所述的制备具有UV滤光活性的微胶囊的方法,其中使至少一种具有UV-A和/或UV-B和/或UV-C滤光活性的可交联发色团和至少一种不具有UV-A和/或UV-B和/或UV-C滤光活性的可交联单体在缺少具有UV-A和/或UV-B和/或UV-C滤光活性的不可交联的发色团的情况下进行交联反应。
3.权利要求1或权利要求2所述的制备具有UV滤光活性的微胶囊的方法,其中微胶囊是通过溶胶-凝胶法制备的。
4.权利要求1-3中任一项所述的制备具有UV滤光活性的微胶囊的方法,其中至少一种具有UV-A和/或UV-B和/或UV-C滤光活性的可交联发色团为式M(R)n(P)m(Q)q的单体,其中M为金属或半金属元素,R为可水解的基团,P为具有UV-A、UV-B和/或UV-C滤光活性的发色团,Q为不可水解的基团,n为2或3,m为1或2且q为0或1,其中n+m+q=4。
5.权利要求4所述的制备具有UV滤光活性的微胶囊的方法,其中发色团P的通式为A-(B)b(C)c(D)d(E)e-,其与M化学键合
其中
A为具有UV-A和/或UV-B滤光活性的发色团且-(B)b(C)c(D)d(E)e-为间隔基团,其中
B为具有最多20个碳原子的直链或支链亚烷基
C为O、S或NH
D为CONH-基团
E为具有最多20个碳原子的直链或支链亚烷基或亚烯基,以及
b为0或1,
c为0或1,
d为0或1,以及
e为0或1。
6.权利要求4或5所述制备具有UV滤光活性的微胶囊的方法,其中金属或半金属元素M为硅。
7.权利要求4或5所述的制备具有UV滤光活性的微胶囊的方法,其中所有用于制备微胶囊的可交联的化合物为含硅的单体。
8.权利要求1-7中任一项所述的制备具有UV滤光活性的微胶囊的方法,其中至少一种具有UV-A和/或UV-B和/或UV-C滤光活性的可交联发色团为包含至少两个C1-6-烷氧基的硅烷单体。
9.权利要求8所述的制备具有UV滤光活性的微胶囊的方法,其中所有用于制备微胶囊的单体为包含至少两个C1-6-烷氧基的硅烷单体。
10.权利要求1-9中任一项所述的制备具有UV滤光活性的微胶囊的方法,其中微胶囊的粒径为0.01-100μm。
11.权利要求1-10中任一项的制备具有UV滤光活性的微胶囊的方法,其中具有UV-A和/或UV-B和/或UV-C滤光活性的可交联发色团的量为使得在最终的微胶囊中UV吸收剂部分的浓度为10-80w/w%的量。
12.按照权利要求1-11中任一项的方法获得的具有UV滤光活性的微胶囊。
13.包含权利要求12中定义的微胶囊的遮光组合物。
14.权利要求12中定义的微胶囊用于制备遮光组合物的用途。
15.具有UV-A和/或UV-B和/或UV-C滤光活性的可交联发色团,其为下式的单体
M(R)n(P)m(Q)q
其中
M为金属或半金属元素,
R为可水解的基团,
Q为不可水解的基团,
n为2或3,m为1或2且q为0或1,其中n+m+q=4,以及
P是具有UV-A、UV-B和/或UV-C滤光活性的发色团,其具有通式A-(B)b(C)c(D)d(E)e-,且与M化学键合
其中
A为具有UV-A和/或UV-B滤光活性的发色团且-(B)b(C)c(D)d(E)e-为间隔基团,其中
B为具有最多20个碳原子的直链或支链亚烷基
C为O、S或NH
D为CONH-基团
E为具有最多20个碳原子的直链或支链亚烷基或亚烯基,以及
b为0或1,
c为0或1,
d为0或1,以及
e为0或1。
16.权利要求15所述的可交联发色团,其中金属或半金属元素M为硅。
17.权利要求15或16所述的可交联发色团,其中基团A为选自丙烯酸酯、对氨基苯甲酸酯、樟脑衍生物、肉桂酸酯、二苯甲酮类、亚苄基丙二酸酯、2-(4-乙氧基苯胺基亚甲基)丙二酸酯、咪唑衍生物、水杨酸酯、三嗪酮衍生物、三唑衍生物、二苯甲酰基甲烷、氨基取代的羟基二苯甲酮、苯基-苯并咪唑、邻氨基苯甲酸酯、苯基-苯并唑和1,4-二氢吡喃的发色团。
19.权利要求15-18所述的可交联发色团,其可通过使式Si(R)r(Q)qS的硅烯与具有UV-A、UV-B和/或UV-C滤光活性的发色团反应而获得,其中R和Q如权利要求15-18任一项中的定义,S为氢原子,-(CH2)o-NCO基团或-(CH2)o-NH2基团,r为2或3,q为0或1且o为1-6。
20.权利要求19所述的可交联发色团,其中硅烷选自
其中Alk为C1-C6烷基。
23.制备权利要求15-21任一项中定义的可交联单体的方法,包括使硅烷分子与发色团反应的步骤。
24.权利要求23所述的制备可交联单体方法,其中硅烷分子如权利要求19或20中的定义。
25.如权利要求23或权利要求24中定义的制备可交联单体的方法,其中发色团如权利要求22中的定义。
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Publication number | Priority date | Publication date | Assignee | Title |
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- 2004-12-02 WO PCT/EP2004/013734 patent/WO2005053631A1/en active Application Filing
- 2004-12-02 CN CN2004800361343A patent/CN1889920B/zh not_active Expired - Fee Related
- 2004-12-02 EP EP04803467A patent/EP1722863B1/en not_active Not-in-force
- 2004-12-02 KR KR1020067011002A patent/KR101123520B1/ko active IP Right Grant
- 2004-12-02 AT AT04803467T patent/ATE544493T1/de active
- 2004-12-02 US US10/581,511 patent/US20070190325A1/en not_active Abandoned
- 2004-12-02 JP JP2006541904A patent/JP4966667B2/ja active Active
-
2011
- 2011-08-02 US US13/195,991 patent/US8765967B2/en not_active Expired - Fee Related
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101328313B (zh) * | 2007-05-16 | 2012-07-18 | 埃姆斯·帕特恩特股份有限公司 | Uv吸收剂在透明聚酰胺模制品制备中的用途 |
CN105534733A (zh) * | 2014-10-28 | 2016-05-04 | 富士胶片株式会社 | 防晒化妆品 |
CN105534733B (zh) * | 2014-10-28 | 2020-02-28 | 富士胶片株式会社 | 防晒化妆品 |
CN107005642A (zh) * | 2014-12-15 | 2017-08-01 | 三星电子株式会社 | 图像捕获设备与感测保护设备 |
CN107005642B (zh) * | 2014-12-15 | 2020-06-12 | 三星电子株式会社 | 图像捕获设备与感测保护设备 |
US10905331B2 (en) | 2014-12-15 | 2021-02-02 | Samsung Electronics Co., Ltd. | Image capturing device and sensing protection device |
CN112203629A (zh) * | 2018-05-14 | 2021-01-08 | 强生消费者公司 | 保湿霜和乳液 |
CN112203629B (zh) * | 2018-05-14 | 2023-08-11 | 强生消费者公司 | 保湿霜和乳液 |
Also Published As
Publication number | Publication date |
---|---|
JP4966667B2 (ja) | 2012-07-04 |
CN1889920B (zh) | 2011-04-13 |
ATE544493T1 (de) | 2012-02-15 |
WO2005053631A1 (en) | 2005-06-16 |
US20070190325A1 (en) | 2007-08-16 |
EP1722863A1 (en) | 2006-11-22 |
KR101123520B1 (ko) | 2012-03-13 |
US20120022265A1 (en) | 2012-01-26 |
US8765967B2 (en) | 2014-07-01 |
EP1722863B1 (en) | 2012-02-08 |
KR20060124606A (ko) | 2006-12-05 |
JP2007519617A (ja) | 2007-07-19 |
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