CN1324610A - 氨基羟基二苯甲酮作光稳定紫外线滤光剂必要组分的防晒组合物在化妆品和药物中的应用 - Google Patents
氨基羟基二苯甲酮作光稳定紫外线滤光剂必要组分的防晒组合物在化妆品和药物中的应用 Download PDFInfo
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Abstract
含化合物A)和B)的防晒组合物在使人体皮肤和头发免受阳光晒伤的化妆品和药物制品中用作光稳定性紫外线滤光剂的用途,任选地与其它吸收紫外线的和化妆品和药物制品领域已知的化合物一起应用,A)为主要吸收UV-A区域紫外线的化合物,B)为其它吸收UV-A区域、UV-B区域紫外线和对两个区域紫外线均吸收的化合物,其中组分(A)含有式Ⅰ的羟基二苯甲酮和其它任选化合物,和组分B)选自式Ba)-Bh)的至少一种,式Ⅰ中R1、R2和R3及式Ba)-Bh)的含义见说明书。
Description
本发明涉及防晒组合物在保护人表皮或人头发免受UV尤其是波长范围为320-400nm的紫外线照射的化妆品和药物制品中的应用,所述组合物含有吸收UV-A区域紫外线的组分一氨基取代的羟基二苯甲酮,和至少一种其它吸收UV-A或UV-B区域紫外线或者对两个区域紫外线均吸收的选自下面详细定义的作为光稳定性UV滤光剂组合物。
在化妆品和药物制品中使用防晒剂的目的是预防或至少减少太阳光对人皮肤的有害作用。然而,这些防晒剂也起到了防止其它组分因UV照射而发生分解或降解的作用。在护发化妆品中,目的是减少UV射线对角蛋白纤维的损害。
到达地球表面的太阳光包含UV-B(波长为280-320nm)和UV-A(波长>320nm),它们紧紧靠近可见光区。紫外线对人皮肤的晒伤作用是明显的,尤其是UV-B。因而,工业上提供了大量的吸收UV-B的物质由此来避免皮肤被晒伤。
皮肤学研究业已证实:UV-A也可造成皮肤损伤及过敏,例如它可以损害角蛋白或弹性蛋白。这会降低皮肤的弹性和蓄水性,即皮肤变得粗糙并易于起皱纹。日照强的地区皮肤癌发生率显著高的事实表明,太阳光特别是UV-A对皮肤细胞的遗传信息也有损害作用。因此,所有这些发现均提示开发UV-A区域的有效滤光物质的必要性。
对用于化妆品和药品的防晒剂有着日益增长的需求,特别是最大吸收波长范围约320-380nm的可以作为UV-A滤光剂的防晒剂。为了以最小剂量应用即达到所需的效果,这类防晒剂应该另外具有高效的特异吸收。用于化妆品的防晒剂还需要满足许多其它的要求,比如在化妆品油脂中的良好溶解性、由其产生的乳液的高稳定性、可接受的毒性和其本身的无色无味。
对防晒剂的另一要求是,它必须具有足够强的光稳定性。然而,迄今可用的所有吸收UV-A的防晒剂仅仅能够部分确保光稳定性。
法国专利2440933号公开了4-(1,1-二甲基乙基)-4’-甲氧基二苯甲酰基甲烷作为UV-A滤光剂,该发明提出用这种特别的UV-A滤光剂(它已被GIVAUDAN以“PARSOL1789”为名出售)和不同的UV-B滤光剂联合以吸收波长为280-380nm的所有UV射线。
然而,这种UV-A滤光剂不具有足够强的光化学稳定性,在长时间日照期间,如果需要对皮肤进行免受所有UV损害的有效保护的话,为了确保持续地保护皮肤的作用,单独使用或联合UV-B滤光剂使用时,需要有规律地且以较短的间隔频繁敷用。
为此,EP-A-0514491公开了一种稳定这些没有足够光稳定性的UV-A滤光剂的方法:通过加入2-氰基-3,3-二苯基丙酸酯,这些化合物本身就起UV-B滤光剂的作用。
EP-A-0251398和EP-A-0416837也已进一步提出使用一个连接子将吸收UV-A和UV-B的生色团结合在一个分子中。这种方法的不足之处在于:在化妆品中,首先是UV-A和UV-B滤光剂的自由结合是不可能的;而且,由于化学方法连接生色团方面的困难而只限于为数不多的几种结合方式。
本发明的目的之一是提供化妆品用和药用的防晒剂,这些防晒剂在UV-A区域具有高效吸收性能,是光稳定性的,低的本色(即具有尖锐的谱带结构),以及具有由取代基决定的水溶性或脂溶性。
我们发现通过特定的防晒组合可以有利地达到本发明目的。
因此,通过在保护人体皮肤或头发免受太阳光晒伤的化妆品和药物制品中使用包括下述组分的防晒组合可以实现本发明目的:A)主要吸收UV-A区域紫外线的化合物,和B)其它吸收UV-A区域、UV-B区域紫外线和对两个区域紫外线均吸收的化合物,其中吸收UV-A区域紫外线的组分(A)包含有效量的至少Aa)一种式Ⅰ的羟基二苯甲酮,Ⅰ,式中,R1和R2各自独立地是氢、C1-C20-烷基、C3-C10-环烷基或C3-C10-环烯基,其中R1和R2可以与同它们相连的氮原子一起形成5-元或6-元环,R3是C1-C20-烷基,
和任选地其它添加组分Ab)式Ⅱ的4,4’-二芳基丁二烯Ⅱ,式中,R4和R5各自独立地是氢、C1-C20-烷基、C3-C10-环烷基或C3-C10-环烯基,和组分B)有效量的至少一种选自下述Ba)-Bh)的作为光稳定性滤光剂的化合物,任选地与其它吸收UV区域紫外线的以及那些已知的自身用于化妆品和药物制品的化合物一起应用:Ba)式Ⅲ的二苯甲酰基甲烷化合物Ⅲ,式中,R6是C1-C12-烷基,而R7是氢、C1-C12-烷基或C1-C12-烷氧基,Bb)式Ⅳ的三嗪衍生物式中,R8~R10各自独立地代表任选被取代的C1-C20-烷基、C5-C10-芳基、C5-C10-杂芳基或SpSil,其中Sp是一个间隔基,而Sil是硅烷、低聚硅氧烷或多聚硅氧烷基,X是二价基-O-或N-R11
其中R11是氢或任选被取代的C1-C20-烷基、C5-C10-芳基或C5-C10-杂芳基,Bc)式Ⅴ的三嗪衍生物Ⅴ,式中,具有1~20个碳原子的至少一个邻-羟基和至少一个对-烷氧基连接到苯环上,Bd)式Ⅵ的苯并三唑衍生物ⅥBe)式Ⅶ的苯并咪唑衍生物及其盐ⅦBf)式Ⅷ的苯并三唑衍生物ⅧBg)式Ⅸ的邻,邻’-对,对’-四羟基二苯甲酮Ⅸ,Bh)式Ⅹa的有机硅氧烷亚苄基丙二酸酯,或者式Ⅹa和Ⅹb的化合物的混合物,Ⅹa,式中,V1’是基团V1是甲基或V1’,或式ⅩbⅩb,其中V2’是结构为下式的基团V2是甲基或V2’,其中t值可高达100,u值高达20,前提是当V1=V1’和/或V2=V2’时u=0,而当V1=CH3和/或V2=CH3时u的值为1~20,
任选地,该组合物含有其它吸收UV光区和化妆品和药物制品领域已知的其它化合物。
尽管在防晒配制品中应当至少含有有效量的化合物(A)和(B),但是化合物(A)和(B)的防晒组合可以单独使用,或者与其它吸收UV的化合物联合使用。“有效量的化合物(A)和(B)”,一般指基于化妆品总量计,每一配制品中至少含有0.2重量%。
本发明防晒组合物中,吸收UV-B的化合物的量通常占主导地位。因此,基于(A)和(B)的防晒组合物总量计,吸收UV-A的化合物(A)的含量一般为5~50重量%,优选10~25重量%。
本发明(A)和(B)的防晒组合物在免遭太阳光损害的保护作用方面具有协同作用,因为联合应用时的保护作用大于各自组分作用的加和。
构成防晒组合基本成分的组分Aa)是前德国专利申请DE-A1191706的发明主题,在所述申请中详细公开了包括制备在内的有关内容。
R1、R2和/或R3的适宜烷基是支链或直链C1-C20-烷基链,优选是甲基、乙基、正丙基、1-甲基乙基、正丁基、1-甲基丙基、2-甲基丙基、1,1-二甲基乙基、正戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、2,2-二甲基丙基、1-乙基丙基、正己基、1,1-二甲基丙基、1,2-二甲基丙基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1,1-二甲基丁基、1,2-二甲基丁基、1,3-二甲基丁基、2,2-二甲基丁基、2,3-二甲基丁基、3,3-二甲基丁基、1-乙基丁基、2-乙基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基-1-甲基丙基、1-乙基-2-甲基丙基、正庚基、正辛基或2-乙基己基。
R1、R2或R3的优选烷基是甲基、乙基、正丙基、1-甲基乙基、正丁基、1-甲基丙基、2-甲基丙基、1,1-二甲基乙基、正戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、2,2-二甲基丙基和2-乙基己基。
R3的优选C3-C10-环烷基是环丙基、环戊基和环己基。
任选的化合物Ab),即式Ⅱ的4,4’-二芳基丁二烯由EPA916335公开。取代基R4和/或R5优选是C1-C8-烷基和C5-C8-环烷基,特别优选新戊基。Ⅱ,
化合物(B)全部是已知的,其特征详述如下:
(Ba)式Ⅲ的化合物由FR2440933可知。式Ⅲ的一个适宜且优选的化合物是对-甲氧基-对’-叔-丁基-二苯甲酰基甲烷(R6=甲氧基,R7=叔-丁基)。
(Bb)式Ⅳ中R8~R10为甲基、芳基或杂芳基的化合物由EP-A0796851、EP-A0087098和EP-A0850935可知。适宜的烷基是,尤其是直链或支链C1-C12烷基,特别是C1-C8烷基。芳基是,例如苯基或萘基,尤其是苯基。适宜的杂芳基是具有1个或多个杂芳原子的3-~6-元环的单环或稠和环系。环或环系中的杂原子可以是一个或多个氮、硫和/或氧原子。
具有SpSil的式Ⅳ化合物由EPA0933376已知。
术语间隔基Sp,是指在连接中将硅烷、低聚硅氧烷或多聚硅氧烷分子连接到三嗪基上的二价的支链或非支链C3-C12亚烷基链或亚烯基链。
C3-C12-亚烷基链的实例是亚丙基、2-甲基亚丙基、亚丁基、亚戊基和亚己基。
C3-C12-亚烯基链的实例是2-亚丙烯-2-基、2-甲基-3-亚丙烯基基、3-亚丁烯-3-基和4-亚戊烯-4-基。
优选的间隔基是-(CH2)3-、-(CH2)4-、-(CH2)5-、[CH(CH3)]-(CH2)-、-(CH2)2-CH=CH-、-C(=CH2)-CH2-、-C(=CH2)-(CH2)2-O-(CH2)4-、-(CH2)4-O-(CH2)2-。
连接中的术语硅烷代表基团是SiR12R13R14,其中R12、R13和R14各自独立地为C1-C6-烷基、C1-C6-烷氧基或苯基。
提到的实例是:Si(CH2-CH3)3、Si(CH2-CH2-CH3)3、Si(异丙基)3、Si(叔-丁基)3、Si(叔-丁基)(CH3)2、Si(CH3)2(己基)、Si(OCH3)3、Si(氧乙基)3、SiPh3。
术语低聚硅氧烷指具有下组通式中之一的基团:SiR15 m(OSiR15 3)n,其中m=0、1或2;n=3、2或1,而m+n=3,R15-[Si(R15)2-O-]r-Si(R15)2-A和R15-[Si(R15)2-O-]r-Si(A)(R15)-O-Si(R15)3,其中A是化学键或间隔基或者R15是C1-C6-烷基或苯基,而r的值为1~9。
术语多聚硅氧烷包括,例如具有下组通式中之一的基团:A-[Si(R16)2-O]s-Si(R16)2-A或(R16)3-Si-[O-Si(R16)2]t-[O-Si(R16)(A)]q-O-Si(R16)3,其中A是化学键或间隔基并且R16是C1-C6-烷基或苯基,s或t的值为4~250,而q的值为1~30。
(Bc)被至少一个邻-羟基和至少一个对-烷氧基取代的式Ⅴ的三苯基三嗪可由WO99/66896得知。
其中X是氢或羟基,Y是羟基,R17是氢或具有1~12个碳原子的烷氧基,R18和R19是具有1~12个碳原子的烷氧基。
(Bd)具有CAS号为103597-45-1的式Ⅵ化合物。
(Be)具有CAS号为180898-37-7的式Ⅶ化合物。
(Bt)具有CAS号为155633-54-8的式Ⅷ化合物。
(Bg)具有CAS号为131-55-5的式Ⅸ化合物。
(Bh)由EP-A0920859公开的式Ⅹa和Ⅹb化合物。
CAS号为208391-15-5、208391-15-5D、177955-90-7、177955-90-7D和177995-90-7DP的式Ⅹa和/或Ⅹb尤为适宜。
在本发明防晒组合物中,(Ba)~(Bh)的化合物不仅可以单独存在,而且可以以两种或多种化合物的混合物形式存在。
本发明进一步涉及含有基于化妆品和药物制品总重量计0.1~10重量%、优选1~7重量%防晒组合物的化妆品和药物制品,所述防晒组合物含有A)主要吸收UV-A区域紫外线的化合物,和B)其它吸收UV-A区域、UV-B区域紫外线和对两个区域紫外线均吸收的化合物,其中吸收UV-A区域紫外线的组分(A)包含有效量的至少Aa)一种式Ⅰ的羟基二苯甲酮,Ⅰ,式中,R1和R2各自独立地是氢、C1-C20-烷基、C3-C10-环烷基或C3-C10-环烯基,其中R1和R2可以与同它们相连的氮原子一起形成5-元或6-元环,R3是C1-C20-烷基,
和任选地其它化合物Ab)式Ⅱ的4,4’-二芳基丁二烯Ⅱ,式中,R4和R5各自独立地是氢、C1-C20-烷基、C3-C10-环烷基或C3-C10-环烯基,和组分B)有效量的至少一种选自下述Ba)-Bh)的作为光稳定性滤光剂的化合物,任选地与其它吸收UV区域紫外线的以及那些已知的自身用于化妆品和药物制品的化合物一起应用,其中吸收UV-A的化合物的量通常小于吸收UV-B的化合物的量:Ba)式Ⅲ的二苯甲酰基甲烷化合物Ⅲ,式中,R6是C1-C12-烷基,而R7是氢、C1-C12-烷基或C1-C12-烷氧基,Bb)式Ⅳ的三嗪衍生物式中,R8~R10各自独立地代表被任选取代的C1-C20-烷基、C5-C10-芳基、C5-C10-杂芳基或SpSil,其中Sp是一个间隔基,而Sil是硅烷、低聚硅氧烷或多聚硅氧烷基,X为二价基-O-或N-R11其中R11是氢或任选被取代的C1-C20-烷基、C5-C10-芳基或C5-C10-杂芳基,Bc)式Ⅴ的三嗪衍生物Ⅴ,式中,具有1~20个碳原子的至少一个邻-羟基和至少一个对-烷氧基连接到苯环上,Bd)式Ⅵ的苯并三唑衍生物ⅥBe)式Ⅶ的苯并咪唑衍生物及其盐ⅧBf)式Ⅷ的苯并三唑衍生物ⅧBg)式Ⅸ的邻,邻’-对,对’-四羟基二苯甲酮Ⅸ,Bh)式Ⅹa的有机硅氧烷亚苄基丙二酸酯,或者式Ⅹa和Ⅹb的化合物的混合物,Ⅹa,式中,V1’是基团V1是甲基或V1’,或式ⅩbⅩb,其中V2’是结构为下式的基团V2是甲基或V2’,其中t值可高达100,u值高达20,前提是当V1=V1’和/或V2=V2’时u=0,而当V1=CH3和/或V2=CH3时u的值为1~20。
吸收UV-A和UV-B和在化妆品和药物制品领域已知的用作防晒剂的任选的其它化合物,一般地,吸收UV-A的化合物用量比吸收UV-B的化合物用量更少。
作为原则,含防晒剂的化妆品或药物制品以包括至少一种油相的载体为基质。然而,如果使用具有亲水取代基的化合物,那么,配制品完全以水相为基质也是可能的。因此,油、水包油和油包水乳液、膏霜和糊剂、防护性棒剂组合物或脱脂凝胶均是合适的。
适宜的乳液也尤其是含有式Ⅰ氨基取代的羟基二甲苯酮的油/水粗乳液、油/水微乳液或油/水/油乳液分散形式,按照DE-A-19726121中所描述的相转换技术,可以得到所述乳液。
可适宜作为添加剂的惯常化妆品辅助剂,例如是,辅助乳化剂、脂肪和蜡、稳定剂、增稠剂、生物活性物质、成膜剂、香味剂、染料、珠光剂、防腐剂、颜料、电解质(如硫酸镁)和pH调节剂。适宜并优选的辅助乳化剂是已知的水/油和油/水乳化剂,如聚甘油酯、脱水山梨醇酯或部分酯化的甘油。典型的脂肪为甘油酯;上述的蜡尤其是指蜂蜡、石蜡和微晶蜡,它们可与亲水性蜡联合使用。所用的稳定剂可为脂肪酸的金属盐,如硬脂酸镁、硬脂酸铝和/或硬脂酸锌。适宜的增稠剂是例如交联的聚丙烯酸及其衍生物、多糖特别是黄原胶、瓜尔胶、琼脂凝胶、藻酸盐和tyloses、羧甲基纤维素和羟乙基纤维素,也可以是脂肪醇、单甘油酯和脂肪酸、聚丙烯酸酯、聚乙烯醇、聚乙烯吡咯烷酮。生物活性物质的实例是,如植物提取物、蛋白质水解物和维生素复合物。成膜剂的实例是,水胶体如聚氨基葡糖、微晶聚氨基葡糖和季铵化聚氨基葡糖、聚乙烯吡咯烷酮、乙烯吡咯烷酮/乙烯醋酸共聚物、丙烯酸系列的聚合物和季铵化纤维素的衍生物和类似物。适宜的防腐剂的实例是,如福尔马林溶液、对羟基苯甲酸酯或山梨酸。适宜的珠光剂的实例是,二硬脂酸乙二醇酯如二硬脂酸乙二醇酯,但是,也可以是脂肪酸和脂肪酸单乙二醇酯。可使用的染料是那些适宜并被批准用于化妆品的物质,例如在Verlag Chemie,Weinheim 1984年出版的由Farbstoffkommission derDeutschen Forschungsgemeinschaft[德国研究协会染料委员会(DyesCommission of German Research Society)]所著的出版物“KosmetischeFrbemittel”[化妆品着色剂(Cosmetic Colorants)]中所列出的物质。这些染料的正常使用浓度是基于混合物总重量的0.001~0.1%。
另外增加抗氧剂含量通常是优选的。因此,作为有利的抗氧剂而使用所有惯常的或适宜于化妆品和/或皮肤应用的抗氧剂是可能的。
抗氧剂选自下列物质是有益的:氨基酸(如,甘氨酸、组氨酸、酪氨酸、色氨酸)及其衍生物,咪唑类化合物(如咪唑丙烯酸)及其衍生物,肽类化合物如D,L-肌肽、D-肌肽、L-肌肽及其衍生物(如鹅肌肽),类胡萝卜素,胡萝卜素(如β-胡萝卜素、番茄红素)及其衍生物,绿原酸及其衍生物,硫辛酸及其衍生物(如二氢硫辛酸),金硫葡萄糖,丙基硫氧嘧啶,和其它硫醇化合物(如thiorodoxin、谷胱甘肽、半胱氨酸、胱氨酸、胱胺和它们的葡糖基酯、N-乙酰酯、甲基酯、乙基酯、丙基酯、戊基酯、丁基酯和月桂基酯、棕榈酰基酯、油醇酯、γ-亚油醇酯(γ-linoleyl)、胆甾醇酯和甘油酯)及其盐,硫代二丙酸二月桂基酯、硫代二丙酸二硬脂基酯、硫代二丙酸及其衍生物(酯、醚、肽、类脂、核苷酸、核苷及盐),以及极低耐受剂量(例如pmol-mol/kg)的磺基亚胺类(sulfoximines)化合物(如,四硫堇(buthionine)磺基亚胺、高半胱氨酸硫堇亚胺、四硫堇亚砜、五-、六-和七-硫堇亚胺磺基亚胺类),还有(金属)螯合剂(例如,α-羟基脂肪酸、棕榈酸、植酸和乳铁蛋白),α-羟基酸(例如柠檬酸、乳酸和苹果酸),腐植酸,胆汁酸,胆汁提取物,胆红素,胆绿素,EDTA及其衍生物,不饱和脂肪酸及其衍生物(例如,γ-亚麻酸、亚油酸和油酸),叶酸及其衍生物,泛醌和泛醌醇及其衍生物,维生素C及其衍生物(如,抗坏血酸棕榈酸盐(ascorbyl palmitate)、抗坏血酸磷酸镁和抗坏血酸醋酸盐),生育酚及其衍生物(如,醋酸生育酚、生育三烯醇(tocotrienol)),维生素A及其衍生物(如维生素A棕榈酸盐),和安息香树脂的苯甲酸松脂,芸香亭酸及其衍生物,α-葡糖基芸香苷(α-glycosylrutin),阿魏酸,furfurylideneglucitol,肌肽,丁羟基甲苯,丁羟基苯甲醚,去甲二氢愈创木脂酸,去甲二氢愈创木酸,三羟基丁酰苯,尿酸及其衍生物,甘露糖及其衍生物,锌及其衍生物(例如,ZnO,ZnSO4)、硒及其衍生物(例如硒代蛋氨酸)、二苯乙烯(stilbenes)及其衍生物(如,氧化二苯乙烯,反-氧化二苯乙烯)。
上述抗氧剂(一种或多种化合物)在配制品中的用量,优选占基于制剂总重量的0.001~30重量%,优选0.05-20%重量、特别优选1~10重量%。
如果维生素E和/或其衍生物作为抗氧剂的话,选择其特定浓度范围为基于制剂总重量的0.001~10重量%是有益的。
如果维生素A和/或其衍生物,或者胡萝卜素类作为抗氧剂的话,选择其特定浓度范围为基于制剂总重量的0.001~10重量%是有益的。
化妆品中常规用的油性组分是,例如,石蜡油、硬脂酸甘油酯、肉豆蔻酸异丙酯、己二酸二异丙酯、2-乙基己酸鲸蜡硬脂基酯、氢化聚异丁烯、凡士林、辛酸/癸酸甘油三酯、微晶蜡、羊毛脂和硬脂酸。
基于组合物总重量计,辅剂和添加剂的总量可以是1~80重量%,优选6~40重量%,而非水内容物(“活性物质”)的含量可以是20~80重量%,优选30~70重量%。可以通过已知的方式制备组合物,例如热、冷、热-热/冷或PIT乳化方式。这是纯粹的机械过程,无任何化学反应发生。
因此,此防晒配制品可以是液体、糊剂或固体剂型,例如,油包水膏霜剂、水包油膏霜和洗液、气溶胶泡沫乳、凝胶、油、眉笔、粉剂、喷雾剂或醇-水洗液。
最后,与其它已知的那些吸收UV区域紫外线并且本身与本发明所用UV滤光剂联合时在整个系统中稳定的物质共同使用也是可能的。
其它任何UV-A和UV-B滤光物质均适宜与本发明防晒组合物共同使用。其实例可例举如下:
编号 | 物质 | CAS号(=酸) |
1 | 4-氨基苯甲酸 | 150-13-0 |
2 | 3-(4-三甲基铵)亚苄基-2-茨酮-甲基硫酸盐 | 52793-97-2 |
3 | 3,3,5-三甲基环己基水扬酸酯(胡莫柳酯) | 118-56-9 |
4 | 2-羟基-4-甲氧基二苯酮(羟苯腙) | 13l-57-7 |
5 | 2-苯基苯并咪唑-5-硫酸及其钾盐、钠盐和三乙醇铵盐 | 27503-81-7 |
6 | 3,3’-(1,4-亚苯基二次甲基)双(7,7-二甲基-2-氧双环[2,2,1]庚烷-1-甲烷-硫酸)及其盐 | 90457-82-2 |
7 | 聚乙氧基乙基4-双(聚乙氧基)氨基苯甲酸酯 | 113010-52-9 |
8 | 4-二甲基氨基苯甲酸2-乙基己基酯 | 21245-02-3 |
9 | 水杨酸2-乙基己基酯 | 118-60-5 |
10 | 4-甲氧基肉桂酸异戊基酯 | 71617-10-2 |
11 | 4-甲氧基肉桂酸2-乙基己基酯 | 5466-77-3 |
12 | 2-羟基-4-甲氧基二苯酮-5-磺酸(即舒利苯酮)及其钠盐 | 4065-45-6 |
13 | 3-(4’-磺基)亚苄基-2-茨酮及其盐 | 58030-58-6 |
14 | 3-亚苄基-2-茨酮 | 16087-24-8 |
15 | 1-(4’-异丙基苯基)-3-苯丙烷-1,3-二酮 | 63260-25-9 |
16 | 水杨酸4-异丙基酯 | 94134-93-7 |
17 | 2,4,6-三苯胺(邻-羰-2’-乙基己基-1’-氧)-1,3,5-三嗪 | 88122-99-0 |
18 | 3-咪唑-4-基-丙烯酸及其乙酯 | 104-98-3 |
19 | 2-氰基-3,3-二苯基丙烯酸乙酯 | 5232-99-5 |
20 | 2-氰基-3,3-二苯基丙烯酸2’-乙基己基酯 | 6197-30-4 |
21 | 邻-氨基苯甲酸甲酯,或者5-甲基-2-(1-甲基乙基)-2-氨基苯甲酸酯 | 134-09-8 |
22 | 对-氨基苯甲酸甘油酯或4-氨基苯甲酸-1-甘油酯 | 136-44-7 |
23 | 2,2’-二羟基-4-甲氧基二苯酮(二羟苯腙) | 131-53-3 |
24 | 2-羟基-4-甲氧基-4’-甲基二苯酮(甲克酮) | 1641-17-4 |
25 | 水杨酸三乙醇铵 | 2174-16-5 |
26 | 二甲氧基苯基乙醛酸,或者3,4-二甲氧基苯基乙醛酸钠 | 4732-70-1 |
27 | 3-(4-磺基)亚苄基-2-茨酮及其盐 | 56039-58-8 |
28 | 4-叔丁基-4’-甲氧基二苯甲酰基甲烷 | 70356-09-1 |
29 | 2,2’4,4’-四羟基二苯酮 | 131-55-5 |
30 | 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] | 103597-45-1 |
31 | 2,2’-(1,4-亚苯基)-双-1H-苯并咪唑-4,6-二磺酸、钠盐 | 180898-37-7 |
32 | 2,4-双-[4-(2-乙基己基氧)-2-羟基]苯基-6-(4-甲氧基苯基)-(1,3,5)三嗪 | 187393-00-6 |
本发明化妆品和皮肤用配制品可以进一步含有基于金属氧化物的无机颜料和/或其它不溶于水或事实上不溶于水的金属化合物,尤其是下列金属的氧化物:钛(TiO2)、锌(ZnO)、铁(如,Fe2O3)、锆(ZrO2)、硅(SiO2)、锰(如MnO)、铝(Al2O3)、铈(如,Ce2O3),这些金属形形色色的氧化物,以及这些金属氧化物的混合物。尤其优选基于TiO2和ZnO的颜料。
为了本发明目的,无机颜料以疏水形式存在即表面处理以防水是特别优越的,但是并非强制性的。按照DE-A-331474.2所描述的,此种表面处理可涉及通过已知方式为颜料提供一薄的疏水层。
为保护人头发免受UV射线损害,本发明防晒组合物可以以0.1~10重量%、优选1~7重量%的浓度掺入到香波、洗剂、凝胶、喷发胶、气溶胶泡沫乳或乳液中。可以用于各种制剂,尤其是洗发、染发和头发定型制剂。
本发明防晒组合物能够很容易地在化妆品油中溶解并且很容易地掺入到化妆品制剂中。使用新的防晒组合物配制的乳液具有卓越的性能,尤其是其高稳定性,防晒组合物本身的高光稳定性和用防晒组合物制备的配制品用于皮肤后的舒爽感觉。
本发明防晒组合物中UV滤光剂的作用也可以用于稳定化妆品和药物制剂中的活性成分和辅剂。
下面的实施例详细描述本发明新防晒组合物的应用。
实施例
实施例1
测定光稳定性的标准方法(太阳光测试)
所用的测试液是5重量%的防晒剂乙醇溶液,用20μ1Eppendorf管将其置于一小块玻璃板的磨砂区域。由于乙醇的存在,溶液均匀分布在粗糙的玻璃表面。其用量与防晒霜中防晒剂达到平均防晒系数所需的用量相当。本试验中,每次照射4小块玻璃板,蒸发和照射的持续时间各为30分钟。照射期间通过装置底部的水冷凝系统缓缓地冷却玻璃板。照射期间,太阳测试装置内的温度为40℃。照射之后,用乙醇将试样洗入到50ml黑色量瓶中,用光度计测量。以同样方式将空白样品置于玻璃板上,室温下蒸发30分钟。同处理其它样品的过程类似,用乙醇洗涤后稀释至100ml进行测量。
化妆品乳液的一般制备方法
在一搅拌容器中,将所有脂溶性成分加热到85℃。当所有成分溶化或呈液相后,通过均质作用加入水相。乳液搅拌冷却至约40℃,再加入香料并均质化,继续搅拌冷却至25℃。
配制品
实施例2-润唇组合物含量(重量%)加至100 Eucerinum anhydricum10.00 甘油1.00 氧化钛,微粉化5.00 1%Aa(式Ⅰ,R=正己基)、1%Bb(式Ⅳa)和3%Bd(式Ⅵ)化合物的组合8.00 甲氧基肉桂酸辛酯5.00 氧化锌4.00 蓖麻油4.00 硬脂酸/癸酸/辛酸/己二酸的季戊四醇酯3.00 硬质酸甘油酯SE2.00 蜂蜡2.00 微晶蜡2.00 Quatemium-18膨润土1.50 PEG-45/十二烷基乙二醇共聚物
实施例3-润唇组合物含量(重量%)加至100 Eucerinum anhydricum10.00 甘油10.00 二氧化钛,微粉化5.00 1%Aa(式Ⅰ,R=正己基)、1%Ab(式Ⅱ,R=新戊基)和3%Bd(式Ⅵ)化合物的组合8.00 甲氧基肉桂酸辛酯5.00 氧化锌4.00 蓖麻油4.00 硬脂酸/癸酸/辛酸/己二酸的季戊四醇酯3.00 硬质酸甘油酯SE2.00 蜂蜡2.00 微晶蜡2.00 Quatemium-18膨润土1.50 PEG-45/十二烷基乙二醇共聚物实施例4-含有微细颜料的防晒组合物含量(重量%)加至100 水10.00 甲氧基肉桂酸辛酯6.00 PEG-7氢化蓖麻油6.00 氧化钛,微粉化5.00 2%Aa(式Ⅰ,R=正己基)、1%Bb(式Ⅳa)和2%Bd(式Ⅵ)化合物的组合5.00 矿物油5.00 对甲氧基肉桂酸异戊酯5.00 丙二醇3.00 西蒙得木油3.00 4-甲基亚苄基樟脑2.00 PEG-45/十二烷基乙二醇共聚物1.00 甲聚硅氧烷0.50 PEG-40氢化蓖麻油0.50 乙酸生育酚酯0.50 苯氧乙醇0.20 EDTA实施例4-含有微细颜料的防晒组合物含量(重量%)加至100 水10.00 甲氧基肉桂酸辛酯6.00 PEG-7氢化蓖麻油6.00 氧化钛,微粉化5.00 2%Aa(式Ⅰ,R=正己基)、1%Bb(式Ⅳa)和2%Bd(式Ⅵ)化合物的组合5.00 矿物油5.00 对甲氧基肉桂酸异戊酯5.00 丙二醇3.00 西蒙得木油3.00 4-甲基亚苄基樟脑2.00 PEG-45/十二烷基乙二醇共聚物1.00 二甲聚硅氧烷0.50 PEG-40氢化蓖麻油0.50 酸生育酚酯0.50 苯氧乙醇0.20 EDTA实施例5-含有微细颜料的防晒组合物含量(重量%)加至100 水10.00 甲氧基肉桂酸辛酯6.00 PEG-7氢化蓖麻油6.00 氧化钛,微粉化5.00 1.5%Aa(式Ⅰ,R=正己基)、1%Ab(式Ⅱ,R=新戊基)和2.5%Bb(式Ⅳb)化合物的组合5.00 矿物油5.00 对甲氧基肉桂酸异戊酯5.00 丙二醇3.00 西蒙得木油3.00 4-甲基亚苄基樟脑2.00 PEG-45/十二烷基乙二醇共聚物1.00 甲聚硅氧烷0.50 PEG-40氢化蓖麻油0.50 酸生育酚酯0.50 苯氧乙醇0.20 EDTA
实施例6-脱脂凝胶含量(重量%)加至100 水8.00 甲氧基肉桂酸辛酯7.00 氧化钛,微粉化5.00 1%Aa(式Ⅰ,R=正己基)、2%Bf(式Ⅷ)和2%Bc(式Ⅴb) 化合物的组合5.00 甘油5.00 PEG-25对氨基苯甲酸1.00 4-甲基亚苄基樟脑0.40 丙烯酸酯和C10-C30烷基丙烯酸酯的交联共聚物0.30 咪唑啉基脲0.25 羟乙基纤维素0.25 对羟基苯甲酸甲酯钠0.20 EDTA二钠0.15 香料0.15 对羟基苯甲酸丙酯钠0.10 氢氧化钠
实施例7-脱脂凝胶含量(重量%)加至100 水8.00 甲氧基肉桂酸辛酯7.00 二氧化钛,微粉化5.00 1%Aa(式Ⅰ,R=正己基)、1%Ab(式Ⅱ,R=新戊基)和3%Bf(式Ⅷ)化合物的组合5.00 甘油5.00 PEG-25对氨基苯甲酸1.00 4-甲基亚苄基樟脑0.40 丙烯酸酯和C10-C30烷基丙烯酸酯的交联共聚物0.30 咪唑啉基脲0.25 羟乙基纤维素0.25 对羟基苯甲酸甲酯钠0.20 EDTA二钠0.15 香料0.15 对羟基苯甲酸丙酯钠0.10 氢氧化钠
实施例8-防晒霜含量(重量%)加至100 水8.00 甲氧基肉桂酸辛酯8.00 二氧化钛,微粉化6.00 PEG-7氢化蓖麻油5.00 1.5%Aa(式Ⅰ,R=正己基)、1.5%Bg(式Ⅸ)和2%Bb(式Ⅳb)化合物的组合6.00 矿物油5.00 氧化锌5.00 棕榈酸异丙酯0.30 咪唑啉基脲3.00 西蒙得木油2.00 PEG-45/十二烷基二醇共聚物1.00 4-甲基亚苄基樟脑0.60 硬脂酸镁0.50 酸生育酚酯0.25 对羟基苯甲酸甲酯0.20 EDTA二钠0.15 对羟基苯甲酸丙酯
实施例9-防晒霜含量(重量%)加至100 水8.00 甲氧基肉桂酸辛酯8.00 氧化钛,微粉化6.00 PEG-7氢化蓖麻油5.00 2%Aa(式Ⅰ,R=正己基)、1%Be(式Ⅶ)和2%Bc(式Ⅴb)化合物的组合6.00 矿物油5.00 氧化锌5.00 棕榈酸异丙酯0.30 咪唑啉基脲3.00 西蒙得木油2.00 PEG-45/十二烷基二醇共聚物1.00 4-甲基亚苄基樟脑0.60 硬脂酸镁0.50 酸生育酚酯0.25 对羟基苯甲酸甲酯0.20 EDTA二钠0.15 对羟基苯甲酸丙酯
实施例10-防水防晒霜含量(重量%)加至100 水8.00 甲氧基肉桂酸辛酯5.00 PEG-7氢化蓖麻油5.00 丙二醇4.00 棕榈酸异丙酯4.00 癸酸/辛酸甘油三酯5.00 1%Aa(式Ⅰ,R=正己基)、1%Ab(式Ⅱ,R=新戊基)、1%Bb(式Ⅳa)和2%Bd(式Ⅵ)化合物的组合4.00 甘油3.00 西蒙得木油2.00 4-甲基亚苄基樟脑2.00 二氧化钛,微粉化1.50 PEG-45/十二烷基二醇共聚物1.50 甲聚硅氧烷0.70 硫酸镁0.50 硬脂酸镁0.15 香料
实施例11-防水防晒霜含量(重量%)加至100 水8.00 甲氧基肉桂酸辛酯5.00 PEG-7氢化蓖麻油5.00 丙二醇4.00 棕榈酸异丙酯4.00 癸酸/辛酸甘油三酯5.00 1%Aa(式Ⅰ,R=正己基)、1%Bb(式Ⅳa)和1%Ba(式Ⅲ,R6=叔丁基,R7=甲氧基)、2%Bb(式Ⅳb)化合物的组合4.00 甘油3.00 西蒙得木油2.00 4-甲基亚苄基樟脑2.00 二氧化钛,微粉化1.50 PEG-45/十二烷基二醇共聚物1.50 二甲聚硅氧烷0.70 硫酸镁0.50 硬脂酸镁0.15 香料
实施例12-防晒乳含量(重量%)加至100 水10.00 矿物油6.00 PEG-7氢化蓖麻油5.00 棕榈酸异丙酯3.50 甲氧基肉桂酸辛酯5.00 1%Aa(式Ⅰ,R=正己基)和4%Bb(式Ⅳb)化合物的组合3.00 癸酸/辛酸甘油三酯3.00 西蒙得木油2.00 PEG-45/十二烷基乙二醇共聚物0.70 硫酸镁0.60 硬脂酸镁0.50 酸生育酚酯3.00 甘油0.25 对羟苯甲酸甲酯0.15 对羟苯甲酸丙酯0.05 生育酚
实施例13-防晒乳含量(重量%)加至100 水10.00 矿物油6.00 PEG-7氢化蓖麻油5.00 棕榈酸异丙酯3.50 甲氧基肉桂酸辛酯5.00 0.5%Aa(式Ⅰ,R=正己基)、1%Bb(式Ⅳa)和3.5%Bc(式Ⅴb)化合物的组合3.00 癸酸/辛酸甘油三酯3.00 西蒙得木油2.00 PEG-45/十二烷基二醇共聚物0.70 硫酸镁0.60 硬脂酸镁0.50 酸生育酚酯3.00 甘油0.25 对羟苯甲酸甲酯0.15 对羟苯甲酸丙酯0.05 生育酚
Claims (14)
1.含有化合物A)和B)的防晒组合物在使人体皮肤和头发免受太阳光晒伤的化妆品和药物制品中用作光稳定性紫外线滤光剂的用途,A)主要吸收UV-A区域紫外线的化合物,B)其它吸收UV-A区域、UV-B区域紫外线和对两个区域紫外线均吸收的化合物,其中吸收UV-A区域紫外线的组分(A)包含有效量的至少Aa)一种式Ⅰ的羟基二苯甲酮,Ⅰ,式中,R1和R2各自独立地是氢、C1-C20-烷基、C3-C10-环烷基或C3-C10-环烯基,其中R1和R2可以与同它们相连的氮原子一起形成5-元或6-元环,R3是C1-C20-烷基,
和任选地其它化合物Ab)式Ⅱ的4,4’-二芳基丁二烯Ⅱ,式中,R4和R5各自独立地是氢、C1-C20-烷基、C3-C10-环烷基或C3-C10-环烯基,其中组分B)包含有效量的至少一种选自下述Ba)-Bh)的作为光稳定性滤光剂的化合物:Ba)式Ⅲ的二苯甲酰基甲烷化合物Ⅲ,式中,R6是C1-C12-烷基,而R7是氢、C1-C12-烷基或C1-C12-烷氧基,Bb)式Ⅳ的三嗪衍生物式中,R8~R10各自独立地代表任选被取代的C1-C20-烷基、C5-C10-芳基、C5-C10-杂芳基或SpSil,其中Sp是一个间隔基,而Sil是硅烷、低聚硅氧烷或多聚硅氧烷基,X是二价基-O-或N-R11
其中R11是氢或任选被取代的C1-C20-烷基、C5-C10-芳基或C5-C10-杂芳基,Bc)式Ⅴ的三嗪衍生物Ⅴ,式中,具有1~20个碳原子的至少一个邻-羟基和至少一个对-烷氧基连接到苯环上,Bd)式Ⅵ的苯并三唑衍生物ⅥBe)式Ⅶ的苯并咪唑衍生物及其盐ⅦBf)式Ⅷ的苯并三唑衍生物ⅧBg)式Ⅸ的邻,邻’-对,对’-四羟基二苯甲酮ⅨBh)式Ⅹa的有机硅氧烷亚苄基丙二酸酯,或者式Ⅹa和Ⅹb的化合物的混合物,Ⅹa,式中,V1’是基团V1是甲基或V1’,或式ⅩbⅩb,其中V2’是结构为下式的基团V2是甲基或V2’,其中t值可高达100,u值高达20,前提是当V1=V1’和/或V2=V2’时u=0,而当V1=CH3和/或V2=CH3时u的值为1~20,任选地与其它吸收UV区域紫外线的以及那些化妆品和药物制品领域已知的化合物一起应用。
2.权利要求1所述防晒组合物的用途,其中包括R3为正己基的权利要求l所述作为必要组分A)的式Ⅰ羟基二苯甲酮。
3.权利要求1所述的防晒组合物的用途,其中包括R4和/或R5为新戊基的式Ⅱ化合物。
4.权利要求1所述的防晒组合物的用途,其中包括取代基-X-R8~-X-R10为2-乙基己氧基的式Ⅳ的三嗪衍生物作为组分Bb)。
5.权利要求1所述的防晒组合物的用途,其中包括取代基-X-R8是叔丁氨基,-X-R9和-X-R10为2-乙基己氧基的式Ⅳ的三嗪衍生物作为组分Bb)。
6.权利要求1所述的防晒组合物的用途,基于防晒组合物总重量计,其中包括至少5重量%的式Ⅰ的必要组分Aa)。
7.权利要求1所述的防晒组合物的用途,B)中进一步包括氧化锌和二氧化钛形式的颜料。
8.含有保护人体皮肤和头发免受280nm~400nmUV光晒伤的防晒组合物的化妆品或药物制品,包括适于化妆品用和药用的载体,作为光稳定性UV滤光剂的有效量的含有化合物A)和B)的防晒组合物,任选地与其它吸收UV区域紫外线的以及那些已知的自身用于化妆品和药物制品的化合物一起应用,其中A)主要吸收UV-A区域紫外线的化合物,B)其它吸收UV-A区域、UV-B区域紫外线和对两个区域紫外线均吸收的化合物,其中吸收UV-A区域紫外线的组分(A)包含有效量的至少Aa)一种式Ⅰ的羟基二苯甲酮,Ⅰ式中,R1和R2各自独立地是氢、C1-C20-烷基或C3-C10-环烷基或C3-C10-环烯基,其中R1和R2可以与同它们相连的氮原子一起形成5-元或6-元环,R3是C1-C20-烷基,
和任选地其它化合物Ab)式Ⅱ的4,4’-二芳基丁二烯Ⅱ,式中,R4和R5各自独立地是氢、C1-C20-烷基、C3-C10-环烷基或C3-C10-环烯基,其中组分B)为有效量的至少一种选自下述Ba)-Bh)的作为光稳定性滤光剂的化合物:Ba)式Ⅲ的二苯甲酰基甲烷化合物Ⅲ,式中,R6是C1-C12-烷基,而R7是氢、C1-C12-烷基或C1-C12-烷氧基,Bb)式Ⅳ的三嗪衍生物式中,R8~R10各自独立地代表被任选取代的C1-C20-烷基、C5-C10-芳基、C5-C10-杂芳基或SpSil,其中Sp是一个间隔基,而Sil是硅烷、低聚硅氧烷或多聚硅氧烷基,X是二价基-O-或N-R11
其中R11是氢或任选被取代的C1-C20-烷基、C5-C10-芳基或C5-C10-杂芳基,Bc)式Ⅴ的三嗪衍生物Ⅴ,式中,具有1~20个碳原子的至少一个邻-羟基和至少一个对-烷氧基连接到苯环上,Bd)式Ⅵ的苯并三唑衍生物ⅥBe)式Ⅶ的苯并咪唑衍生物及其盐ⅦBf)式Ⅷ的苯并三唑衍生物ⅧBg)式Ⅸ的邻,邻’-对,对’-四羟基二苯甲酮ⅨBh)式Ⅹa的有机硅氧烷亚苄基丙二酸酯,或者式Ⅹa和Ⅹb的化合物的混合物,Ⅹa,式中,V1’是基团V1是甲基或V1’,或式ⅩbⅩb,其中V2’是结构为下式的基团V2是甲基或V2’,其中t值可高达100,u值高达20,前提是当V1=V1’和/或V2=V2’时u=0,而当V1=CH3和/或V2=CH3时u的值为1~20。
9.含有权利要求8所述防晒组合物的化妆品或药物制品,其中防晒组合物含有权利要求8中作为必要组分A)的通式Ⅰ中R3为正己基的羟基二苯甲酮。
10.含有权利要求8所述防晒组合物的化妆品或药物制品,其中防晒组合物含有R4和/或R5为新戊基的通式Ⅱ化合物。
11.含有权利要求8所述防晒组合物的化妆品或药物制品,其中防晒组合物含有作为组分Bb)的-X-R8~-X-R10为2-乙基己氧基的式Ⅳ三嗪衍生物。
12.含有权利要求8所述防晒组合物的化妆品或药物制品,其中防晒组合物含有作为组分Bb)的-X-R8为叔-丁氨基而-X-R9和-X-R10为乙基己氧基的式Ⅳ三嗪衍生物。
13.含有权利要求8所述防晒组合物的化妆品或药物制品,其中防晒组合物含有基于防晒组合物重量计至少5重量%的式Ⅰ的必要组分Aa)。
14.含有权利要求8所述防晒组合物的化妆品或药物制品,其中防晒组合物另外含有氧化锌或二氧化钛形式的B)颜料。
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EP0251398B1 (en) | 1986-06-27 | 1992-08-12 | The Procter & Gamble Company | Novel chromophores, sunscreen compositions and methods for preventing sunburn |
US5087445A (en) | 1989-09-08 | 1992-02-11 | Richardson-Vicks, Inc. | Photoprotection compositions having reduced dermal irritation |
FR2658075B1 (fr) | 1990-02-14 | 1992-05-07 | Oreal | Composition cosmetique filtrante photostable contenant un filtre uv-a et un beta,beta-diphenylacrylate ou alpha-cyano-beta,beta-diphenylacrylate d'alkyle. |
IT1289511B1 (it) | 1996-12-23 | 1998-10-15 | 3V Sigma Spa | Soluzioni concentrate di filtro solare derivato della 1,3,5- triazina e loro uso per la preparazione di composizioni cosmetiche |
DE19726121A1 (de) | 1997-06-20 | 1998-12-24 | Beiersdorf Ag | Kosmetische und dermatologische Lichtschutzformulierungen in Form von Emulsionen, insbesondere O/W-Makroemulsionen, O/W-Mikroemulsionen oder O/W/O-Emulsionen, mit einem Gehalt an Bis-Resorcinyltriazinderivaten |
GB9715751D0 (en) * | 1997-07-26 | 1997-10-01 | Ciba Geigy Ag | Formulations |
EP0916335B1 (de) | 1997-08-13 | 2004-11-03 | Basf Aktiengesellschaft | Photostabile UV-Filter enthaltende kosmetsche und pharmazeutische Zubereitungen |
EP0933376B1 (en) | 1998-01-02 | 2003-08-20 | F. Hoffmann-La Roche Ag | Silanyl-triazines as light screening compositions |
AU757342B2 (en) | 1998-06-22 | 2003-02-20 | Ciba Specialty Chemicals Holding Inc. | Sun screen formulations |
DE19917906A1 (de) | 1999-04-20 | 2000-10-26 | Basf Ag | Verwendung von aminosubstituierten Hydroxybenzophenonen als photostabile UV-Filter in kosmetischen und pharmazeutischen Zubereitungen |
-
2000
- 2000-03-15 DE DE10012408A patent/DE10012408A1/de not_active Withdrawn
-
2001
- 2001-03-01 EP EP01104958A patent/EP1133980A3/de not_active Withdrawn
- 2001-03-07 US US09/805,727 patent/US6387355B2/en not_active Expired - Fee Related
- 2001-03-13 JP JP2001070070A patent/JP2001261540A/ja not_active Withdrawn
- 2001-03-14 AU AU28003/01A patent/AU2800301A/en not_active Abandoned
- 2001-03-15 BR BR0101085-9A patent/BR0101085A/pt not_active IP Right Cessation
- 2001-03-15 CN CN01116869A patent/CN1324610A/zh active Pending
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101081900B (zh) * | 2005-06-01 | 2011-07-27 | 信越化学工业株式会社 | 含紫外线吸收性基团的有机聚硅氧烷、该聚硅氧烷的制法、及配合该聚硅氧烷的处理剂 |
CN105380810A (zh) * | 2009-01-29 | 2016-03-09 | 巴斯夫欧洲公司 | 化妆品组合物的稳定 |
CN105380810B (zh) * | 2009-01-29 | 2021-02-26 | 巴斯夫欧洲公司 | 化妆品组合物的稳定 |
CN110037932A (zh) * | 2019-04-10 | 2019-07-23 | 广东聚石化学股份有限公司 | 一种含羟基的紫外线吸收剂的制备方法和应用 |
CN110037932B (zh) * | 2019-04-10 | 2022-04-01 | 广东聚石化学股份有限公司 | 一种含羟基的紫外线吸收剂的制备方法和应用 |
Also Published As
Publication number | Publication date |
---|---|
US6387355B2 (en) | 2002-05-14 |
BR0101085A (pt) | 2001-11-06 |
AU2800301A (en) | 2001-09-20 |
EP1133980A3 (de) | 2004-01-02 |
DE10012408A1 (de) | 2001-09-20 |
EP1133980A2 (de) | 2001-09-19 |
JP2001261540A (ja) | 2001-09-26 |
US20020001570A1 (en) | 2002-01-03 |
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