CN107669503A - 硅烷‑和硅氧烷‑二(二苯基)三嗪衍生物作为uv吸收剂的用途 - Google Patents
硅烷‑和硅氧烷‑二(二苯基)三嗪衍生物作为uv吸收剂的用途 Download PDFInfo
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- CN107669503A CN107669503A CN201711046655.2A CN201711046655A CN107669503A CN 107669503 A CN107669503 A CN 107669503A CN 201711046655 A CN201711046655 A CN 201711046655A CN 107669503 A CN107669503 A CN 107669503A
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Abstract
本发明涉及式(1)的硅烷‑和硅氧烷‑二(二苯基)三嗪衍生物作为UV吸收剂的用途,其中n是1‑4的数;若n=1,则X是*‑L‑Sil;或式(11’)基团,L是选自式(2)基团的连接基;R1、R2、R3各自是C1‑C22烷基、C6‑C20芳基、C1‑C22烷氧基或O‑C6‑C20芳基;R4、R5、R6和R7各自是氢、C1‑C22烷基,C6‑C20芳基、C1‑C22烷氧基或O‑C6‑C20芳基;b是0‑30的数;c是0‑6的数;d是0‑1的数;p是1‑250的数;q是0‑250的数;Sil、Sil1和Sil2各自是硅烷、低聚硅氧烷或聚硅氧烷结构部分;若n=2,则X是式(1a)或(1b)的二价基团;x是2‑250的数;y是0‑250的数;z是1‑50的数;若n=3,则X是含有硅烷、低聚硅氧烷或聚硅氧烷结构部分的三价基团;若n=4,则X是式(1c)四价基团;A是式(111’)基团。
Description
本申请是中国专利申请201180061750.4的分案申请,该中国专利申请的申请日为2011年10月20日,发明名称是“硅烷-和硅氧烷-二(二苯基)三嗪衍生物作为UV吸收剂的用途”。
技术领域
本发明涉及新型硅烷-、硅氧烷-或聚硅氧烷-二(二苯基)三嗪衍生物作为UV吸收剂的用途,以及它们在防晒组合物和/或化妆品组合物中的用途。
背景技术
众所周知,紫外辐照(光)对人的皮肤有害。根据波长,UV辐照引起不同类型的皮肤损伤。UV-B辐照(约290-320nm)会引起晒伤并能引起皮肤癌。UV-A辐照(约320-400nm)在使皮肤变黑的同时,也会引起晒伤,并引起皮肤癌。此外,UV-B辐照的有害作用会由UV-A辐照加重。
所以,有效的防晒配料优选同时含有至少一种UV-A和UV-B滤光剂和宽带UV滤光剂以覆盖约290-400nm的整个范围,从而防止人的皮肤受到日光的有害影响。
除了它们对太阳辐照的屏蔽作用之外,UV滤光剂必须还具有优良的耐水性和耐汗性以及满意的光稳定性。
不幸的是,许多有效的有机UV滤光剂在特定浓度下具有不良的油溶性,并倾向于结晶。因此,UV防护效率显著降低。
已经知道有亲油性UV滤光剂,例如丁基甲氧基二苯甲酰基甲烷(以商品名“Parsol1789”由DSM销售),其具有细节,其缺点是在环境温度下是固体。结果,它们在防晒化妆品组合物中的应用受到在其配方和应用方面的一些限制,尤其是在选择特定的合适化妆品溶剂方面,所述溶剂能提供对这些滤光剂的适当溶解性。因此,UV滤光剂应当显示在常规化妆油中的高溶解性,或应当是对于其它的显示不良油溶解性的UV滤光剂而言的良溶剂。
此外,油溶性UV滤光剂应当包含在化妆品防晒产品中且不会对乳液的感官性能有任何影响。所以,应当确保在涂布之后UV吸收剂在留在皮肤上的亲水-亲油膜内的最佳分布。
所以,本发明的目的是提供UV吸收剂配料,其具有关于UV吸收剂的改进的性能。
发明内容
惊奇的是,发现特定的硅烷-和硅氧烷-二(二苯基)三嗪衍生物具有作为化妆品UV-B吸收剂的非常好的性能。
所以,本发明涉及由以下通式(1)表示的硅烷-和硅氧烷-二(二苯基)三嗪衍生物作为UV吸收剂的用途:
其中
n是1-4的数;
如果n=1,
则X是*-L-Sil;或下式的基团:
L是选自式(2)基团的连接基:
R1、R2、R3各自独立地是C1-C22烷基;C6-C20芳基;C1-C22烷氧基;或O-C6-C20芳基;
R4、R5、R6和R7各自独立地是氢;C1-C22烷基;C6-C20芳基;C1-C22烷氧基;或O-C6-C20芳基;
b是0-30的数;
c是0-6的数;和
d是0-1的数;
p是1-250的数;
q是0-250的数;和
Sil、Sil1和Sil2各自独立地是硅烷结构部分、低聚硅氧烷结构部分或聚硅氧烷结构部分;
如果n=2,
则X是式(1a)或(1b)的二价基团:
x是2-250的数;
y是0-250的数;和
z是1-50的数;
如果n=3,
则X是含有硅烷结构部分、低聚硅氧烷结构部分或聚硅氧烷结构部分的三价基团;
如果n=4,
则X是式(1c)的四价基团:
和
A是下式的基团:
优选的是式(1)的化合物,其中:
n是1-4的数;
如果n=1,
则X是*-L-Sil;
L是选自式(2)基团的连接基:
R4、R5、R6和R7各自独立地是氢;C1-C22烷基;C6-C20芳基;C1-C22烷氧基;或O-C6-C20芳基;
b是0-30的数;
c是0-6的数;和
d是0-1的数;
Sil、Sil1和Sil2各自独立地是硅烷结构部分、低聚硅氧烷结构部分或聚硅氧烷结构部分;
R1、R2、R3各自独立地是C1-C22烷基;C6-C20芳基;C1-C22烷氧基;或O-C6-C20芳基;
x是2-250的数;
y是0-250的数;和
z是1-50的数;
如果n=3,
则X是含有硅烷结构部分、低聚硅氧烷结构部分或聚硅氧烷结构部分的三价基团;
如果n=4,
则X是式(1c)的四价基团。
优选,Sil是选自Si(R1)m[OSi(R2)]o的低聚硅氧烷结构部分;其中:
m是0、1或2,
o是3、2或1;
m和o的总和是3;和
R1和R2各自独立地是C1-C22烷基;C6-C20芳基;C1-C22烷氧基;或O-C6-C20芳基。
优选的硅烷基团是三甲基硅烷、三乙基硅烷、三丙基硅烷、三异丙基硅烷、二甲基叔丁基硅烷、二甲基己基硅烷、三苯基硅烷、二甲基苯基硅烷等。
其它优选的是使用这里所述的二(二苯基)三嗪的混合物。
优选的是式(2)的化合物,其中
R4和R5各自独立地是氢;或C1-C22烷基;
b是1-30的数;和
c和d是0。
甚至更优选的是式(2)的化合物,其中R4和R5各自独立地是氢或C1-C5烷基;或式(2)的化合物,其中R4和R5各自独立地是氢或甲基。
最优选的是式(2)的化合物,其中b是1-5的数。
最优选的是式(1)的化合物,其中X对应于下式(3):
其中
“亚烷基”表示直链或支化的C2-C12亚烷基;
R8、R9和R10各自独立地是C1-C22烷基;或C1-C22烷氧基;或式(3a)的基团:
R11和R12和R13各自独立地是C1-C22烷基;或C1-C22烷氧基;和e是0-30的数。
也优选的是式(1)的化合物,其中:
X是下式的基团:
其中
p和q各自独立地是1-20的数;最优选是3-15。
根据本发明的二(二苯基)三嗪化合物的例子列在下表1中:
式(1)的化合物是新的。
所以,本发明还涉及式(1)的硅烷-和硅氧烷-二(二苯基)三嗪衍生物:
其中
n是1-4的数;
如果n=1,
则X是*-L-Sil;或下式的基团:
L是选自式(2)基团的连接基:
R4、R5、R6和R7各自独立地是氢;C1-C22烷基;C6-C20芳基;C1-C22烷氧基;或O-C6-C20芳基;
b是0-30的数;
c是0-6的数;和
d是0-1的数;
p是1-250的数;
q是0-250的数;和
Sil、Sil1和Sil2各自独立地是硅烷结构部分、低聚硅氧烷结构部分或聚硅氧烷结构部分;
如果n=2,
则X是式(1a)或(1b)的二价基团:
R1,R2,R3各自独立地是C1-C22烷基;C6-C20芳基;C1-C22烷氧基;或O-C6-C20芳基;
x是2-250的数;
y是0-250的数;和
z是1-50的数;
如果n=3,
则X是含有硅烷结构部分、低聚硅氧烷结构部分或聚硅氧烷结构部分的三价基团;
如果n=4,
则X是式(1c)的四价基团:
和
A是下式的基团
式(1)的化合物可以通常从通式(1)的化合物进行氢化甲硅烷基化反应获得,其中基团X含有能随后被氢化甲硅烷基化的不饱和C-C键。这些化合物例如对应于式(3)。
更优选,基团X是烯丙基。
氢化甲硅烷基化反应是在不饱和化合物与含SiH的硅烷、低聚硅氧烷和聚硅氧烷之间按照以下的反应路线进行的:
其中
R8是氢;C1-C22烷基;C6-C20芳基;C1-C22烷氧基;或O-C6-C20芳基;
b是0-30的数;
c是0-6的数;和
d是0-1的数;其中c或d中的至少一个不是0。
氢化甲硅烷基化反应是在氢化甲硅烷基化催化剂的存在下进行的。
优选,催化剂是铂(0)催化剂,最优选的催化剂是所谓的Karstedt催化剂。
一般,形成了氢化甲硅烷基化加合物的相应区域异构体的混合物。
以下反应路线例示了氢化甲硅烷基化反应。
根据式(1)的硅烷-和硅氧烷-二(二苯基)三嗪衍生物可以有利地在化妆品制剂中用作活性物质,所述化妆品制剂另外含有化妆品可接受的载体或助剂。
除了根据式(1)的硅烷-和硅氧烷-二(二苯基)三嗪衍生物之外,根据本发明的化妆品制剂可以另外含有下述类别的一种或多种的其它UV防护剂:
1.p-氨基苯甲酸衍生物,例如4-二甲基氨基苯甲酸2-乙基己基酯;
2.水杨酸衍生物,例如水杨酸2-乙基己基酯;
3.二苯酮衍生物,例如2-羟基-4-甲氧基二苯酮及其5-磺酸衍生物;
4.二苯甲酰基甲烷衍生物,例如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,例如2-氰基-3,3-二苯基丙烯酸2-乙基己基酯,以及2-氰基丙烯酸3-(苯并呋喃基)酯;
6.3-咪唑-4-基丙烯酸及其酯;
7.苯并呋喃衍生物,尤其是2-(p-氨基苯基)苯并呋喃衍生物,描述在EP-A-582189、US-A-5 338 539、US-A-5 518 713和EP-A-613 893中;
8.聚合物UV吸收剂,例如在EP-A-709 080中描述的亚苄基丙二酸酯衍生物;
9.肉桂酸衍生物,例如4-甲氧基肉桂酸2-乙基己基酯和异戊基酯,或在US-A-5601 811和WO97/00851中公开的肉桂酸衍生物;
10.樟脑衍生物,例如3-(4'-甲基)亚苄基-硼烷-2-酮,3-亚苄基硼烷-2-酮,N-[2(和4)-2-氧基亚硼烷-3-基-甲基)-苄基]丙烯酰胺聚合物,3-(4'-三甲基铵)-亚苄基-硼烷-2-酮甲基硫酸酯,3,3'-(1,4-亚苯基二次甲基)-二(7,7-二甲基-2-氧-二环[2.2.1]庚烷-1-甲烷磺酸)及其盐,3-(4'-磺基)亚苄基-硼烷-2-酮及其盐;樟脑苯扎铵甲基硫酸盐;
11.羟基苯基三嗪化合物,例如2-(4'-甲氧基苯基)-4,6-二(2'-羟基-4'-正辛基氧基苯基)-1,3,5-三嗪;2,4-二{[4-(3-(2-丙基氧基)-2-羟基-丙基氧基)-2-羟基]-苯基}-6-(4-甲氧基苯基)-1,3,5-三嗪;2,4-二{[4-(2-乙基-己基氧基)-2-羟基]-苯基}-6-[4-(2-甲氧基乙基-羧基)-苯基氨基]-1,3,5-三嗪;2,4-二{[4-(三(三甲基甲硅烷基氧基-甲硅烷基丙基氧基)-2-羟基]-苯基}-6-(4-甲氧基苯基)-1,3,5-三嗪;2,4-二{[4-(2"-甲基丙烯基氧基)-2-羟基]-苯基}-6-(4-甲氧基苯基)-1,3,5-三嗪;2,4-二{[4-(1',1',1',3',5',5',5'-七甲基三甲硅烷基-2"-甲基-丙基氧基)-2-羟基]-苯基}-6-(4-甲氧基苯基)-1,3,5-三嗪;2,4-二{[4-(3-(2-丙基氧基)-2-羟基-丙基氧基)-2-羟基]-苯基}-6-[4-乙基羧基)-苯基氨基]-1,3,5-三嗪;
12.苯并三唑化合物,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:
13.三苯胺基-s-三嗪衍生物,例如2,4,6-三苯胺-(p-碳-2'-乙基-1'-氧基)-1,3.5-三嗪以及在US-A-5 332 568、EP-A-517 104、EP-A-507 691、WO 93/17002和EP-A-570838中公开的UV吸收剂;
14.2-苯基苯并咪唑-5-磺酸及其盐;
15.邻-氨基苯甲酸孟基酯;
16.TiO2(不同包封的)、ZnO和云母。
在“防晒剂(Sunscreens)”,Eds.N.J.Lowe,N.A.Shaath,Marcel Dekker,Inc.,NewYork和Basle或在Cosmetics&Toiletries(107),50ff(1992)中描述的UV吸收剂也可以用作另外的UV保护物质。
特别优选的是列在下表中的光防护剂:
每种上述光防护剂、尤其是在上表所列出的优选的光防护剂,可以作为与本发明的硅烷-和硅氧烷-二(二苯基)三嗪衍生物的混合物使用。应当理解的是,在本发明中,除了本发明的二(二苯基)三嗪衍生物的混合物之外,还可以使用多于一种的额外光防护剂,例如2、3、4、5或6种其他光防护剂。
在这些配料中的其它典型成分是防腐剂、杀菌剂和抗菌剂,香料,染料,颜料,增稠剂,保湿剂,润湿剂,脂肪,油,蜡,或化妆品和个人护理配料中的其它典型成分,例如醇、多元醇、聚合物、电解质、有机溶剂、有机硅衍生物、软化剂、乳化剂或乳化表面活性剂、表面活性剂、分散剂、抗氧化剂、抗刺激剂和抗炎剂等。
化妆品组合物含有例如基于组合物总重量计的0.1-30重量%、优选0.1-15重量%和尤其0.5-10重量%的式(1)的硅烷-和硅氧烷-二(二苯基)三嗪衍生物和至少一种化妆品可接受的助剂。
化妆品组合物可以通过使用常规方法将式(1)的硅烷-和硅氧烷-二(二苯基)三嗪衍生物与助剂进行物理混合制备,例如通过将各组分简单地一起搅拌,尤其是利用已知的化妆品UV吸收剂的溶解性能,例如OMC、水杨酸异辛基酯。UV吸收剂可以例如在不经过进一步处理的情况下使用,或以超微细化状态使用,或以粉末的形式使用。
化妆品组合物可以例如是乳霜、凝胶、洗剂、醇溶液和水/醇溶液、乳液、蜡/脂肪组合物、棒状制剂、粉末或软膏。
作为含有水和油的乳液(例如W/O、O/W、O/W/O和W/O/W乳液或微乳液),所述组合物含有例如基于组合物总重量计的0.1-30重量%、优选0.1-15重量%和尤其0.5-10重量%的式(1)的硅烷-和硅氧烷-二(二苯基)三嗪衍生物,基于组合物总重量计的1-60重量%、尤其5-50重量%和优选10-35重量%的至少一种油组分,基于组合物总重量计的0-30重量%、尤其1-30重量%和优选4-20重量%的至少一种乳化剂,基于组合物总重量计的10-90重量%、尤其30-90重量%的水,以及0-88.9重量%、尤其1-50重量%的其它化妆品可接受的助剂。
作为含油的组合物(例如油,W/O,O/W,O/W/O和W/O/W乳液或微乳液)中的油组分,可以考虑例如:基于具有6-18、优选8-10个碳原子的脂肪醇的格尔伯特醇,直链C6-C24脂肪酸与直链C3-C24醇形成的酯,支化C6-C13羧酸与直链C6-C24脂肪醇形成的酯,直链C6-C24脂肪酸与支化醇形成的酯,尤其2-乙基己醇,羟基羧酸与直链或支化C6-C22脂肪醇形成的酯,尤其马来酸二辛酯,直链和/或支化脂肪酸与多元醇(例如丙二醇、二聚体二醇或三聚体三醇)和/或格尔伯特醇形成的酯,基于C6-C10脂肪酸的甘油三酯,基于C6-C18脂肪酸的液体单/二/三甘油酯混合物,C6-C24脂肪醇和/或格尔伯特醇与芳族羧酸、尤其苯甲酸形成的酯,C2-C12二羧酸与具有1-22个碳原子的直链或支化醇或与具有2-10个碳原子和2-6个羟基的多元醇形成的酯,植物油(例如向日葵油、橄榄油、豆油、菜籽油、杏仁油、霍霍巴油、橙油、麦芽油、桃壳油,以及椰子油的液体组分),支化的伯醇,取代的环己烷,直链和支化的C6-C22脂肪醇碳酸酯,格尔伯特碳酸酯,苯甲酸与直链和/或支化C6-C22醇形成的酯(例如TN),直链或支化的、对称或不对称的具有总共12-36个碳原子、尤其12-24个碳原子的二烷基醚,例如二正辛基醚、二正癸基醚、二正壬基醚、二正十一烷基醚、二正十二烷基醚、正己基正辛基醚、正辛基正癸基醚、正癸基正十一烷基醚、正十一烷基正十二烷基醚、正己基正十一烷基醚、二叔丁基醚、二异戊基醚、二-3-乙基癸基醚、叔丁基正辛基醚、异戊基正辛基醚和2-甲基戊基正辛基醚,环氧化脂肪酸酯与多元醇形成的开环产物,硅油和/或脂族烃或环烷烃。也重要的是脂肪酸与具有3-24个碳原子的醇形成的单酯。这类物质包含具有8-24个碳原子的脂肪酸与醇形成的酯化产物,所述脂肪酸例如是己酸、辛酸、2-乙基己酸、癸酸、月桂酸、异十三酸、肉豆蔻酸、棕榈酸、棕榈油酸、硬脂酸、异硬脂酸、油酸、反油酸,岩芹酸,亚油酸,亚麻酸,桐酸,花生酸,鳕烯酸,山嵛酸和芥酸,以及它们的工业级混合物(例如在压力去除天然脂肪和油中、在来自Roelen羰基合成的醛的还原中或在不饱和脂肪酸的二聚中获得),醇例如是异丙醇、己醇,辛醇,2-乙基己基醇,癸醇,月桂醇,异十三醇,肉豆蔻醇,十六醇,棕榈醇,硬脂醇,异硬脂醇,油醇,反油醇,岩芹醇,亚油醇,亚麻醇,桐醇,花生醇,鳕烯醇,山嵛醇,芥醇和巴惟醇,以及它们的工业级混合物(例如在基于脂肪和油的工业级甲基酯的高压氢化中或来自Roelen羰基合成的醛和作为在不饱和脂肪醇的二聚中的单体级分获得)。特别重要的是:肉豆蔻酸异丙基酯,异壬酸C16-C18烷基酯,硬脂酸2-乙基己基酯,油酸十六烷基酯,三辛酸甘油酯,椰油脂肪醇辛酸酯/癸酸酯和硬脂酸正丁基酯。其它可以使用的油组分是二羧酸酯,例如二正丁基己二酸酯,二(2-乙基己基)-己二酸酯,二(2-乙基己基)-琥珀酸酯和二异十三烷基乙酸酯,以及二醇酯,例如乙二醇二油酸酯,乙二醇二异十三烷酸酯,丙二醇二(2-乙基己酸酯),丙二醇二异硬脂酸酯,丙二醇二壬酸酯,丁二醇二异硬脂酸酯和新戊二醇二辛酸酯。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。也可以使用一种或多种烷基羧酸的二价和/或三价金属盐(碱土金属,尤其是Al3 +)。
油组分的用量可以是例如1-60重量%,尤其是5-50重量%,优选是10-35重量%,基于组合物的总重量计。
任何常规可用的乳化剂可以用于所述组合物。
作为乳化剂,可以考虑选自下组的非离子表面活性剂:
-2-30摩尔环氧乙烷和/或0-5摩尔环氧丙烷与具有8-22个碳原子的直链脂肪醇、与具有12-22个碳原子的脂肪酸和与在烷基中具有8-15个碳原子的烷基酚的加成产物,例如Ceteareth-20或Ceteareth-12;
-1-30摩尔环氧乙烷与具有3-6个碳原子的多元醇、尤其与甘油形成的加成产物的C12-C22脂肪酸单酯和二酯;
-具有6-22个碳原子的饱和和不饱和脂肪酸的甘油单酯和二酯和脱水山梨醇单酯和二酯及其环氧乙烷加成产物,例如硬脂酸甘油酯、异硬脂酸甘油酯、油酸甘油酯、油酸脱水山梨醇酯或倍半油酸脱水山梨醇酯;
-C8-C22烷基-单-和低聚-糖苷及其乙氧基化类似物,低聚度是1.1-5,尤其优选是1.2-1.4,其中葡萄糖优选用作糖组分;
-2-60摩尔、尤其15-60摩尔的环氧乙烷与蓖麻油和/或氢化蓖麻油的加成产物;
-多元醇酯和尤其是聚甘油酯,例如二异硬脂酰基聚甘油基-2-二异硬脂酸酯,聚甘油基-3-二异硬脂酸酯,三甘油基二异硬脂酸酯,聚甘油基-2-倍半异硬脂酸酯或聚甘油基二聚物。多种这些物质的混合物也是合适的;
-基于直链、支化、不饱和或饱和C6-C22脂肪酸、蓖麻酸和12-羟基硬脂酸和基于甘油、聚甘油、季戊四醇、二季戊四醇、糖醇(例如山梨醇)、烷基葡糖苷(例如甲基葡糖苷、丁基葡糖苷、月桂基葡糖苷)和聚葡糖苷(例如纤维素)的偏酯,例如聚甘油基-2-二羟基硬脂酸酯或聚甘油基-3-二蓖麻酸酯;
-单烷基、二烷基和三烷基磷酸酯,以及单-、二-和/或三-PEG-烷基磷酸酯及其盐;
-羊毛脂蜡醇;
-天然衍生物的一种或多种乙氧基化酯,例如氢化蓖麻油的聚乙氧基化酯;
-硅油乳化剂,例如硅氧烷多元醇;
-聚硅氧烷/聚烷基/聚醚共聚物和相应的衍生物,例如十六烷基聚二甲基硅氧烷共聚多元醇;
-季戊四醇、脂肪酸酯、柠檬酸和脂肪醇的混合酯(参见DE-A-1 165574)和/或具有6-22个碳原子的脂肪酸、甲基葡萄糖和多元醇、优选甘油或聚甘油的混合酯,例如聚甘油基-3-葡萄糖二硬脂酸酯、聚甘油基-3-葡萄糖二油酸酯、甲基葡萄糖二油酸酯或二椰油基季戊四醇基二硬脂基柠檬酸酯,和
-聚亚烷基二醇。
环氧乙烷和/或环氧丙烷与脂肪醇、脂肪酸、烷基酚、脂肪酸的甘油单酯和二酯以及脱水山梨醇单酯和二酯或与蓖麻油形成的加成产物是公知的、可商购的产品。它们通常是均匀混合物,其烷氧基化平均度对应于环氧乙烷和/或环氧丙烷和要发生加成反应的基质之间的比率。环氧乙烷与甘油的加成产物的C12-C18脂肪酸单酯和二酯是公知的,例如参见DE-A-2 024051,作为用于化妆品制剂的脂肪储存物质。
C8-C18烷基-单-和低聚-糖苷、其制备方法及其用途可以从现有技术知道。它们尤其通过葡萄糖或低聚糖与具有8-18个碳原子的伯醇反应制备。合适的糖苷基团包括单糖苷,其中环状糖基团按照糖苷形式与脂肪醇连接,以及具有最多优选约8的低聚度的低聚糖苷。低聚度是基于常规用于这种工业级产品的均匀分布的统计平均值。
也可以使用两性离子表面活性剂作为乳化剂。术语“两性离子表面活性剂”尤其表示在分子中带有至少一个季铵基团和至少一个羧酸盐和/或磺酸盐基团的表面活性化合物。尤其合适的两性离子表面活性剂是所谓的甜菜碱,例如N-烷基-N,N-二甲基甘氨酸铵,例如椰油烷基二甲基甘氨酸铵,N-酰基氨基丙基-N,N-二甲基甘氨酸铵,例如椰油酰基氨基丙基二甲基甘氨酸铵,和2-烷基-3-羧基甲基-3-羟基-乙基咪唑啉,其在烷基或酰基中各自具有8-18个碳原子,以及椰油酰基氨基乙基羟基乙基羧基甲基甘氨酸。特别优选CTFA名称为“椰油酰氨基丙基甜菜碱”的脂肪酸酰氨衍生物。也适合作为乳化剂的是两亲性表面活性剂。两亲性表面活性剂理解为表示尤其是这样的,其中除了含有C8-C18烷基或酰基之外,还在分子中含有至少一个游离的氨基和至少一个-COOH或-SO3H基团,并且能形成内盐。合适的两亲性表面活性剂的例子包括N-烷基甘氨酸、N-烷基丙酸、N-烷基氨基丁酸、N-烷基亚氨基二丙酸、N-羟基乙基-N-烷基酰氨基丙基甘氨酸、N-烷基牛磺酸、N-烷基肌氨酸、2-烷基氨基丙酸和烷基氨基乙酸,其各自在烷基中具有约8-18个碳原子。
特别优选的两亲性表面活性剂是N-椰油烷基氨基-丙酸酯、椰油酰基氨基乙基氨基丙酸酯和C12-C18酰基肌氨酸。除了两亲性乳化剂之外,还可以考虑季铵乳化剂,尤其优选酯季铵化物类型的那些,优选甲基季铵化的二脂肪酸三乙醇胺酯盐。
非离子乳化剂是优选的。在提到的非离子乳化剂中,特别优选具有8-22个碳原子和4-30个EO单元的乙氧基化脂肪醇。
乳化剂的用量可以是例如1-30重量%,尤其是4-20重量%,优选5-10重量%,基于组合物的总重量计。但是,也可以原则上省略使用乳化剂。
本发明的组合物,例如乳霜、凝胶、洗剂、醇溶液和水/醇溶液、乳液、蜡/脂肪组合物、棒状制剂、粉末或软膏,可以另外含有作为其它助剂和添加剂的以下物质:温和表面活性剂,超加脂剂,珠光蜡,稠度调节剂,增稠剂,聚合物,有机硅化合物,脂肪,蜡,稳定剂,生物源活性成分,去味活性成分,去头皮屑剂,成膜剂,溶胀剂,其它UV光保护因素,抗氧化剂,水溶助长剂,防腐剂,昆虫驱除剂,自晒黑剂,增溶剂,芳香油,着色剂,细菌抑制剂等。
适合用做超加脂剂的物质是例如羊毛脂、卵磷脂,和聚乙氧基化或丙烯酰基化的羊毛脂和卵磷脂衍生物,多元醇脂肪酸酯,单甘油酯和脂肪酸链烷醇酰胺,后者也同时用作泡沫稳定剂。
合适的温和表面活性剂的例子,也就是说尤其能被皮肤良好接受的表面活性剂,包括脂肪醇聚二醇醚硫酸盐,单甘油酯硫酸盐,单-和/或二-烷基磺基琥珀酸盐,脂肪酸羟乙基磺酸盐,脂肪酸肌氨酸盐,脂肪酸氨基乙磺酸盐,脂肪酸谷氨酸盐,α-烯烃磺酸盐,醚羧酸,烷基低聚葡糖苷,脂肪酸葡糖酰胺,烷基酰氨基甜菜碱,和/或蛋白质脂肪酸缩合产物,后者优选是基于小麦蛋白。
作为珠光蜡,可以考虑例如:亚烷基二醇酯,特别是乙二醇二硬脂酸酯;脂肪酸链烷醇酰胺,特别是椰油脂肪酸二乙醇酰胺;偏甘油酯,特别是硬脂酸单甘油酯;多价的、未取代或被羟基取代的羧酸与具有6-22个碳原子的脂肪醇形成的酯,特别是酒石酸的长链酯;脂肪物质,例如脂肪醇、脂肪酮、脂肪醛、脂肪醚和脂肪碳酸酯,其具有总共至少24个碳原子,特别是月桂酮和二硬脂基醚;脂肪酸,例如硬脂酸、羟基硬脂酸或山嵛酸,具有12-22个碳原子的烯烃环氧化物与具有12-22个碳原子的脂肪醇和/或具有2-15个碳原子和2-10个羟基的多元醇形成的开环产物,以及它们的混合物。
作为稠度调节剂,尤其考虑具有12-22个碳原子、优选16-18个碳原子的脂肪醇或羟基脂肪醇,以及偏甘油酯、脂肪酸和羟基脂肪酸。优选这些物质与烷基低聚葡糖苷和/或相同链长的脂肪酸N-甲基谷氨酸和/或聚甘油聚-12-羟基硬脂酸酯的组合物。合适的增稠剂包括例如Aerosil类型(亲水性硅酸),多糖,尤其是黄原胶、瓜尔胶、藻酸、藻酸盐和Tyloses,羧基甲基纤维素和羟基甲基纤维素,以及较高分子量的脂肪酸聚乙二醇单酯和二酯,聚丙烯酸酯(例如来自Goodrich的或来自Sigma的),聚丙烯酰胺,聚乙烯基醇和聚乙烯基吡咯烷酮,表面活性剂,例如乙氧基化脂肪酸甘油酯,脂肪酸与多元醇形成的酯,例如季戊四醇或三羟甲基丙烷,具有受限均匀分布的脂肪醇乙氧基化物,以及烷基低聚葡糖苷,以及电解质例如氯化钠或氯化铵。
合适的阳离子聚合物是例如阳离子纤维素衍生物,例如季化羟基甲基纤维素,可以以商品名Polymer JR从Amerchol获得;阳离子淀粉,二烯丙基铵盐和丙烯酰胺的共聚物,季化乙烯基吡咯烷酮/乙烯基咪唑聚合物,例如(BASF),聚二醇和胺的缩合产物,季化胶原多肽,例如月桂基二甲基铵羟基丙基水解胶原(L/Grünau),季化小麦多肽,聚乙烯亚胺,阳离子有机硅聚合物,例如酰胺基聚甲基硅氧烷,己二酸和二甲基氨基羟基丙基二亚乙基三胺的共聚物(Sandoz),丙烯酸与二甲基二烯丙基氯化铵的共聚物(550/Chemviron),聚氨基聚酰胺,例如参见FR-A-2 252840,以及它们的交联的水溶性聚合物,阳离子壳多糖衍生物,例如季化脱乙酰壳多糖,任选作为微晶分布;二卤代烷基化物的缩合产物,例如二溴丁烷,以及二烷基胺,例如双二甲基氨基-1,3-丙烷,阳离子瓜尔胶,例如来自Celanese公司的Jaguar C-17、Jaguar C-16,季铵盐聚合物,例如来自Miranol公司的Mirapol A-15、Mirapol AD-1、Mirapol AZ-1。
作为阴离子、两性离子、两亲性和非离子性聚合物,可以考虑例如乙酸乙烯基酯/巴豆酸共聚物,乙烯基吡咯烷酮/丙烯酸乙烯基酯共聚物,乙酸乙烯基酯/马来酸丁基酯/丙烯酸异冰片酯共聚物,甲基乙烯基醚/马来酸酐共聚物及其酯,未交联的聚丙烯酸和用多元醇交联的聚丙烯酸,丙烯酰氨基丙基-三甲基氯化铵/丙烯酸酯共聚物,辛基丙烯酰胺/甲基丙烯酸甲酯/甲基丙烯酸叔丁基氨基乙基酯/甲基丙烯酸2-羟基丙基酯共聚物,聚乙烯基吡咯烷酮,乙烯基吡咯烷酮/乙酸乙烯基酯共聚物,乙烯基吡咯烷酮/甲基丙烯酸二甲基氨基乙基酯/乙烯基己内酰胺三元共聚物以及任选衍生化的纤维素醚和有机硅。
合适的有机硅化合物例如是:二甲基聚硅氧烷,甲基苯基聚硅氧烷,环硅氧烷,以及氨基-、脂肪酸-、醇-、聚醚-、环氧基-、氟-、糖苷-和/或烷基-改性的硅化合物,它们在室温下可以是液体或树脂形式。也合适的是硅酸盐聚甲基硅氧烷,它们是平均链长度为200-300个二甲基硅氧烷单元的聚二甲基硅氧烷与氢化硅酸盐的混合物。关于合适的挥发性硅氧烷的详细信息,可以参见Todd等,Cosm.Toil.91,27(1976)。
脂肪的典型例子是甘油酯,以及作为蜡,可以考虑尤其是蜂蜡、巴西棕榈蜡,小烛树蜡,褐煤蜡,石蜡,氢化蓖麻油和脂肪酸酯,或在室温下为固体的微晶蜡,其任选地与亲水性蜡组合使用,例如十六烷基十八烷基醇或偏甘油酯。脂肪酸的金属盐可以用作稳定剂,例如镁、铝和/或锌的硬脂酸盐或蓖麻酸盐。
生物源活性成分理解为表示例如生育酚、乙酸生育酚、棕榈酸生育酚、抗坏血酸、脱氧核糖核酸、视黄醇、红没药醇、尿囊素、植三醇、泛醇、AHA酸、氨基酸、神经酰胺、假神经酰胺、精油、植物提取物和维生素复合物。
作为去味活性成分,可以考虑例如防汗剂,例如氯代水合铝(参见J.Soc.Cosm.Chem.24,281(1973))。以商品名例如Hoechst AG的Frankfurt(FRG),可以例如对应于式Al2(OH)5Cl x 2.5H2O的氯代水合铝,尤其优选使用它们(参见J.Pharm.Pharmacol.26,531(1975))。除了氯代水合物之外,也可以使用羟基乙酸铝和酸性铝/锆盐。酯酶抑制剂可以作为其它去味活性成分。这些抑制剂优选是柠檬酸三烷基酯,例如柠檬酸三甲基酯、柠檬酸三丙基酯、柠檬酸三异丙基酯、柠檬酸三丁基酯,特别是柠檬酸三乙基酯(CAT,Henkel kGaA,Dusseldorf/FRG),这些物质抑制酶的活性,从而减少气味的形成。其它适合作为酯酶抑制剂的物质是胆固醇硫酸酯或磷酸酯,例如羊毛甾醇,胆固醇,菜油甾醇,豆甾醇和谷甾醇的硫酸酯或磷酸酯;二羧酸和其酯,例如戊二酸、戊二酸单乙基酯、戊二酸二乙基酯、己二酸、己二酸单乙基酯、己二酸二乙基酯、丙二酸、丙二酸二乙基酯;羟基羧酸和其酯,例如柠檬酸、苹果酸、酒石酸或酒石酸二乙基酯。在制剂中(尤其在棒状制剂中)也可以存在抗菌活性成分,其影响菌落并杀死或抑制分解汗液的细菌的生长。例子包括脱乙酰壳多糖、苯氧基乙醇和氯己定葡糖酸盐。已经证明尤其有效的是5-氯-2-(2,4-二氯苯氧基乙醇)-苯酚(Ciba Specialty Chemicals Inc.)。
作为抗头皮屑剂,可以提到例如甘宝素、吡啶酮乙醇胺盐(Octopirox)和2-巯基吡啶氧化锌。常规的成膜剂包括例如脱乙酰壳多糖,微晶脱乙酰壳多糖,季化脱乙酰壳多糖,聚乙烯基吡咯烷酮,乙烯基吡咯烷酮/乙酸乙烯酯共聚物,含高比例丙烯酸的季化纤维素衍生物的聚合物,胶原,透明质酸和其盐,以及相似的化合物。作为用于水相的溶胀剂,可以使用蒙脱土、粘土物质、Pemulen以及烷基改性类型的Carbopol(Goodrich)。其它合适的聚合物和溶胀剂可以参见R.Lochhead在Cosm.Toil.108,95(1993)中的综述。
除了主要的光防护物质之外,也可以使用抗氧化剂类型的辅助光防护物质,其当UV辐照穿透皮肤或头发时能干扰引起的光化学反应链。这些抗氧化剂的典型例子是:氨基酸(例如甘氨酸、组氨酸、酪氨酸、色氨酸)以及它们的衍生物,咪唑(例如咪唑丙烯酸)以及它们的衍生物,肽,例如D,L-肌肽、D-肌肽、L-肌肽和它们的衍生物(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)和它们的衍生物,绿原酸和它们的衍生物,硫辛酸和它们的衍生物(例如二氢硫辛酸),金硫葡糖,丙基硫尿和它们的硫醇(例如硫氧还蛋白、谷胱甘肽、半胱氨酸、胱氨酸、胱胺和它们的葡糖基酯、N-乙酰基酯、甲酯、乙酯、丙酯、戊酯、丁酯和月桂基酯、棕榈酰酯、油基酯、γ-亚油基酯、胆固醇酯和甘油酯)以及它们的盐,硫代二丙酸二月桂基酯,硫代二丙酸二硬脂基酯,硫代二丙酸和它们的衍生物(酯、醚、肽、类脂、核苷酸、核苷和盐),以及非常少量(例如pmol至μmol/kg)的磺基肟化合物(例如丁基硫堇亚胺、同型半胱氨酸硫堇亚胺、丁硫氨酸砜、五-、六-和七硫堇亚胺),以及(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)、腐殖酸、胆酸、胆酸提取物、胆红素、胆绿素、EDTA、EDDS、EGTA和它们的衍生物,不饱和脂肪酸以及它们的衍生物(例如γ-亚麻酸、亚油酸、油酸),叶酸和它们的衍生物,泛醌和泛醌醇以及它们的衍生物,维生素C和衍生物(例如棕榈酸抗坏血酸基酯、抗坏血酸基磷酸镁、乙酸抗坏血酸基酯),生育酚和衍生物(例如维生素E乙酸酯),维生素A和衍生物(例如维生素A棕榈酸酯),以及苯偶姻树脂的苯甲酸酯,芸香亭酸和它们的衍生物,α-葡糖基芦丁,阿魏酸,亚呋喃基山梨醇,肌钛,丁基羟基甲苯,丁基羟基甲苯茴香醚,树脂状去甲二氢愈创木酸,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,超氧化物歧化酶,N-[3-(3,5-二叔丁基-4-羟基苯基)丙酰基]丙氨酸(及其盐,例如二钠盐),锌及其衍生物(例如ZnO,ZnSO4),硒及其衍生物(例如硒代甲硫酸氨),1,2-二苯乙烯及其衍生物(例如1,2-二苯乙烯氧化物,反式1,2-二苯乙烯氧化物),以及根据本发明合适的这些活性成分的衍生物(盐、酯、醚、糖、核苷酸、肽和类脂)。也可以提到HALS(=“位阻胺光稳定剂”)化合物。抗氧化剂的存在量通常是0.001-30重量%,优选0.01-3重量%,基于式(1)的UV吸收剂的重量计。
为了改进流动行为,也可以使用水溶助长剂,例如乙醇、异丙醇或多元醇。为此目的,可以考虑优选具有2-15个碳原子和至少两个羟基的多元醇。
多元醇也可以含有其它官能团,尤其是氨基,和/或可以用氮改性。典型的例子如下:
-甘油;
-亚烷基二醇,例如乙二醇、二甘醇、丙二醇、丁二醇、亚己基二醇以及平均分子量为100-1000道尔顿的聚乙二醇;
-固有缩合度为1.5-10的工业低聚甘油混合物,例如双甘油含量为40-50重量%的工业双甘油混合物;
-羟甲基化合物,例如尤其是三羟甲基乙烷、三羟甲基丙烷、三羟甲基丁烷、季戊四醇和二季戊四醇;
-低级烷基葡糖苷,尤其是在烷基中具有1-8个个碳原子的那些,例如甲基和丁基葡糖苷;
-具有5-12个碳原子的糖醇,例如山梨醇或甘露醇;
-具有5-12个碳原子的糖,例如葡萄糖或蔗糖;
-氨基糖,例如葡糖胺;
-二醇胺,例如二乙醇胺或2-氨基-1,3-丙二醇。
合适的防腐剂包括例如苯氧基乙醇、甲醛溶液、对羟基苯甲酸酯、戊二醇或山梨酸,以及在“化妆品规章(Cosmetics Regulations)”,部分A和B,列表6(Schedule 6)中列出的其它物质类型。
作为芳香油,可以提到天然和/或合成的芳族物质的混合物。天然的芳族物质是例如来自以下的提取物:花(百合,薰衣草,玫瑰,茉莉,橙花,依兰),根和叶子(天竺葵,广藿香,苦橙叶),果实(八角,香菜,百里香,杜松),果皮(佛手柑,柠檬,橙子),根(肉豆蔻,当归,芹菜,豆蔻,广木香,鹫尾,菖蒲),木材(松木,檀香,愈创木,雪松,红木),草本植物和草(茵陈篙,柠檬草,鼠尾草,麝香草),来自枝叶(云杉,松,苏格兰松,山松),来自树脂和香脂(白松香,榄香,茴香醚,没药,乳香,红没药)。也可以考虑动物原料,例如果子狸和海狸香。典型的合成芳族物质是例如酯、醚、醛、酮、醇或烃类型的产物。
酯类型的芳族物质是例如乙酸苄基酯,异丁酸苯氧基乙基酯,乙酸对-叔丁基环己基酯,乙酸里哪基酯,乙酸二甲基苄基甲基酯,乙酸苯基乙基酯,苯甲酸里哪基酯,甲酸苄基酯,乙基甲基苯基甘氨酸酯,丙酸烯丙基环己基酯,丙酸苯乙烯基酯和水杨酸苄基酯。醚包括例如苄基乙基醚;醛包括例如具有8-18个烃原子的直链醛,柠檬醛,香茅醛,香茅基氧基乙醛,仙客来醛,羟基香茅醛,铃兰醛和波吉洪醛;酮包括例如紫罗兰酮、α-异甲基紫罗兰酮和甲基柏木酮;醇包括例如茴香脑,香茅醇,丁香油,异丁香油,香叶醇,里哪醇,苯基乙基醇和萜品醇;烃主要包括萜烯和香脂。但是优选使用各种芳族物质的混合物,它们一起产生吸引人的气味。具有较低挥发性的醚合物油也适合作为芳香油,它们主要用做芳香组分,例如鼠尾草油,甘菊油,丁香油,柠檬草油,肉桂叶油,莱姆花油,杜松子油,香根草油,乳香油,白松香油,岩蔷薇油和薰衣草油。优选使用佛手柑油,二氢月桂烯醇,铃兰醛,新铃兰醛,香茅醇,苯基乙基醇,α-己基肉桂醛,香叶醇,苄基丙酮,仙客来醛,里哪醇,乙氧基甲氧基环十一烷,龙延呋喃,吲哚,二氢茉莉酮酸甲酯,三得利则,柠檬油,红橘油,橙油,烯丙基戊基乙二醇酯,硬脂酸钙,薰衣草油,香紫苏油,β-突厥酮,香叶油,环己基水杨酸酯,甲基柏木烯酮,异-E-Super,Fixolide NP,橡苔,甲基α-紫罗兰酮(iraldeingamma),苯基乙酸,乙酸香叶酯,乙酸苄基酯,玫瑰醚,罗米亚(romillat),2-乙基己酸乙基酯(Irotyl)和2-叔丁基环己基乙基碳酸酯(Floramat),它们单独使用或作为彼此的混合物使用。
可以用作着色剂的并且适合用于化妆品目的的物质例如汇总在出版物"Kosmetische",Farbstoffkommission der DeutschenForschungsgemeinschaft,Verlag Chemie,Weinheim,1984,第81-106页中。着色剂的浓度通常是0.001-0.1重量%,基于全部混合物计。
细菌抑制剂的典型例子是能抵抗格兰氏阳性菌的物质,例如2,4,4'-三氯-2'-羟基二苯基醚,氯己定(1.6-二(4-氯苯基-双胍基)己烷)或TCC(3,4,4'-三氯-N-碳酰苯胺)。
大量的芳族物质和醚合物油也具有抗菌性能。典型的例子是在丁香油、薄荷油和百里香油中的活性成分丁香油、薄荷醇和百里酚。感兴趣的天然去味剂是萜烯醇金合欢醇(3,7,11-三甲基-2,6,10-十二碳三烯-1-醇),其存在于莱姆花油中。甘油单月桂酸酯也用做抗菌剂。额外抗菌剂的存在量一般是0.1-2重量%,基于制剂的固含量计。
化妆品组合物还可以含有以下物质作为助剂:消泡剂,例如有机硅;结构剂,例如马来酸;增溶剂,例如乙二醇、丙二醇、甘油或二甘醇;不透明剂,例如乳胶、苯乙烯/PVP或苯乙烯/丙烯酰胺共聚物;配合剂,例如EDTA、NTA、β-苯胺二乙酸或膦酸;推进剂,例如丙烷/丁烷混合物、N2O、二甲基醚、CO2、N2或空气;所谓的偶合剂和显影剂组分作为氧化染料前体;还原剂,例如硫代乙醇酸及其衍生物,硫代乳酸,半胱胺,硫代苹果酸或α-巯基乙磺酸;或氧化剂,例如过氧化氢、溴化钾或溴化钠。
可以考虑的驱虫剂是例如N,N-二乙基-间-甲苯酰胺、1,2-戊二醇或驱虫剂3535;合适的自晒黑剂是例如二羟基丙酮,赤藓酮糖,或二羟基丙酮和赤藓酮糖的混合物。
根据本发明的化妆品配料包含在许多化妆品制剂中。可以例如考虑尤其以下制剂:
-皮肤护理制剂,例如皮肤洗涤和清洁制剂,是片剂或液体皂、合成洗涤
剂或洗涤浆料的形式,
-洗浴制剂,例如液体(泡泡浴、乳剂、淋浴制剂)或固体洗浴制剂,例如洗浴块料和浴盐;
-皮肤护理制剂,例如护肤乳液、多重乳液或润肤油;
-化妆品个人护理制剂,例如日霜或粉霜形式的面部粉底,粉底(松散或压紧形式),胭脂或霜剂粉底,眼部护理制剂,例如眼影制剂,腮红,眼线笔、眼霜或眼部定妆剂;唇部护理制剂,例如唇膏、唇彩、唇线笔,指甲护理制剂,例如指甲油、指甲油去除剂、指甲硬化剂或角质去除剂;
-足部护理制剂,例如足部洗浴用品、足粉、护足霜或护足膏,特殊除味剂和防汗剂或去足底老茧制剂;
-光防护制剂,例如防晒乳、防晒液、防晒霜或油,防晒隔离剂或局部用品,预晒黑制剂或晒后制剂;
-皮肤晒黑制剂,例如自晒黑乳剂;
-脱色制剂,例如用于漂白皮肤的制剂或皮肤光亮制剂;
-驱虫剂,例如驱虫油、洗剂、喷雾或棒;
-去味剂,例如去味喷雾、泵式作用喷雾、去味凝胶、棒或走珠;
-防汗剂,例如防汗棒、乳霜或走珠;
-用于清洁和护理粗糙皮肤的制剂,例如合成洗涤剂(固体或液体),剥离式或洗涤式制剂,或剥离式面膜;
-化学形式的头发去除制剂(脱发),例如去发粉、液体脱发制剂,乳霜或糊料形式的去发制剂,凝胶或气溶胶泡沫形式的去发制剂;
-剃须制剂,例如剃须皂、发泡剃须乳、非发泡剃须乳、泡沫和凝胶,剃须钱用于干燥剃须的制剂,剃须后制剂或须后水;
-芳香制剂,例如香料(古龙水,香氛,淡香精,盥用水,香水),芳香油或香料乳;
-化妆用头发处理制剂,例如洗发剂和调理剂形式的洗发制剂,头发护理制剂,例如预处理制剂,头发强壮剂,定型乳,定型凝胶,发油,洗发剂,处理小包,深层头发处理,头发结构化制剂,例如用于永久卷曲的烫发制剂(热烫,温和烫,冷烫),头发拉直制剂,液体头发定型制剂,头发泡沫,头发喷雾剂,漂白制剂,例如过氧化氢溶液,增白洗发剂,漂白乳剂,漂白粉,漂白浆料或油;临时、半永久或永久头发着色剂,含有自氧化染料的制剂,或天然头发着色剂,例如指甲花或甘菊。
所列出的最终配料可以以各种存在形式存在,例如:
-液体制剂的形式,作为W/O、O/W、O/W/O、W/O/W或PIT乳液和所有种类的微乳液,
-凝胶的形式,
-油、乳剂、奶或洗剂的形式,
-粉末、清漆、片剂或粉底的形式,
-棒状物的形式,
-喷雾(带有推进剂气体或起泵作用的喷雾)或气溶胶的形式,
-泡沫的形式,或
-糊料的形式。
特别重要作为用于皮肤的化妆品制剂是光防护制剂,例如防晒奶、洗剂、乳剂、油,日晒隔离或局部用品,预晒黑制剂或晒后制剂,以及皮肤晒黑制剂,例如自晒黑乳。特别感兴趣的是防晒乳、防晒液、防晒油、防晒奶和喷雾形式的防晒制剂。
特别重要的用于头发的化妆品制剂是上述用于头发处理的制剂,尤其是洗发剂形式的头发洗涤制剂,头发调理剂,头发护理制剂例如预处理制剂,头发强壮剂,定型乳,定型凝胶,发油,头发清洗剂,处理小包,深层头发处理剂,头发拉直制剂,液体头发定型制剂,头发泡沫和头发喷雾剂。特别感兴趣的是洗发剂形式的头发洗涤制剂。
洗发剂具有例如以下组成:0.01-5重量%的本发明UV吸收剂,12.0重量%的月桂醇聚醚-2-硫酸钠,4.0重量%的椰油酰胺基丙基甜菜碱,3.0重量%的氯化钠,以及加到100%的水。
例如,尤其可以使用以下头发化妆品配料:
a1)自发乳化原料配料,包含根据本发明的UV吸收剂、PEG-6-C10羰基合成醇和脱水山梨醇倍半油酸酯,其中加入水和任何所需的季铵化合物,例如4%酰胺基丙基二甲基-2-羟基乙基氯化铵或季铵盐(Quaternium)-80;
a2)自发乳化原料配料,包含根据本发明的UV吸收剂、三丁基柠檬酸酯和PEG-20-脱水山梨醇单油酸酯,其中加入水和任何所需的季铵化合物,例如4%酰胺基丙基二甲基-2-羟基乙基氯化铵或季铵盐-80;
b)根据本发明的UV吸收剂在丁基三乙二醇和三丁基柠檬酸酯中的四份掺杂的溶液;
c)根据本发明的UV吸收剂与N-烷基吡咯烷酮的混合物或溶液。
附图说明
图1显示了在光稳定性检测中用于辐照样品的实验设置。
以下实施例用于说明本发明,但不限制本发明的范围。
实施例1:合成硅氧烷二(二苯基)三嗪S-1
在65℃下,将0.72g(0.00315mol,97%)的1,1,1,3,5,5,5-七甲基三硅氧烷加入1.60g(0.003mol)的对应于下式的烯丙基二(二苯基)三嗪2-[4,6-二([1,1’-二苯基]-4-基)-1,3,5-三嗪-2-基]-5-(2-丙烯-1-基氧基)-苯酚(CAS-No.357436-15-8;B-19),
和15滴的铂(0)-1,3-二乙烯基-1,1,3,3-四甲基二硅氧烷配合物(在聚(二甲基硅氧烷)中的溶液,乙烯基封端的,购自Aldrich公司)溶解于25ml甲苯中的混合物中。在120℃下继续加热18小时。在加入25mL乙醇和1g焦炭之后,将混合物于80℃搅拌1小时。过滤出固体,并有少量的1/1乙醇/甲苯混合物洗涤。滤液在真空下浓缩,在70-80℃下干燥,得到高度粘稠的油,其在静置时固化。
得到1.709g(75%产率)的浅黄色粉末。
UV(四氢呋喃):λmax=319nm;ε=72200M-1cm-1。
实施例2:合成硅烷二(二苯基)三嗪S-2
按照与实施例1相似的方式,通过使1.60g(3mmol)的烯丙基二(二苯基)三嗪B-19、0.39g(3.3mmol)三乙基硅烷和15滴的铂(0)-催化剂在25ml甲苯中反应来制备产物。
得到1.55g(80%产率)的黄色树脂,其在数小时之后固化。在研磨时,得到浅黄色粉末。
UV(四氢呋喃):λmax=319nm,ε=76300M-1cm-1。
实施例3:合成硅氧烷二(二苯基)三嗪S-3
按照与实施例1相似的方式,通过使1.60g(3mmol)的烯丙基二(二苯基)三嗪B-19、5.42g(3.3mmol)聚(二甲基硅氧烷)(单-氢和单正丁基封端的,平均Mw=1000道尔顿,产品商品名是Silaplane FM-0111,购自Chisso Corp.)和15滴的铂(0)-催化剂在25ml甲苯中反应来制备产物。
得到4.07g(~88%产率)的黄色蜡。
UV(四氢呋喃):λmax=319nm,ε=68200M-1cm-1。
实施例4:合成硅氧烷二(二苯基)三嗪S-4
按照与实施例1相似的方式,通过使1.60g(3mmol)的烯丙基二(二苯基)三嗪B-19、0.82g(0.5mmol)聚(二甲基硅氧烷-共聚-甲基氢硅烷)(三甲基甲硅烷基封端的,平均Mw=1500道尔顿,33mol%MeHSiO)和15滴的铂(0)-催化剂在25ml甲苯中反应来制备产物。
得到1.13g(~50%产率)的黄色树脂,其在数小时之后固化。在研磨时,得到浅黄色粉末。
UV(四氢呋喃):λmax=316nm,ε=35650M-1cm-1。
实施例5:合成硅氧烷二(二苯基)三嗪S-5
按照与实施例1相似的方式,通过使1.60g(3mmol)的烯丙基二(二苯基)三嗪B-19、0.96g(1.7mmol)聚(二甲基硅氧烷)(氢化物封端的,平均Mn~580,CAS No.70900-21-9,购自Aldrich)和15滴的铂(0)-催化剂在25ml甲苯中反应来制备产物。
得到1.88g(76%产率)的黄色树脂,其在数小时之后固化。在研磨时,得到浅黄色粉末。
熔点:46.8℃。
UV(四氢呋喃):λmax=319nm,ε=118100M-1cm-1。
实施例6:合成硅氧烷二(二苯基)三嗪S-6
按照与实施例1相似的方式,通过使1.15g(2.2mmol)的烯丙基二(二苯基)三嗪B-19、0.15g(0.6mmol)2,4,6,8-四甲基环四硅氧烷和15滴的铂(0)-催化剂在25ml甲苯中反应来制备产物。
得到0.34g的黄色树脂,其在数小时之后固化。在研磨时,得到浅棕色粉末。
熔点:115.5℃。
UV(四氢呋喃):λmax=319nm,ε=29300M-1cm-1。
实施例7:合成硅氧烷二(二苯基)三嗪S-7
按照与实施例1相似的方式,通过使1.15g(2.2mmol)的烯丙基二(二苯基)三嗪B-19、0.71g(0.5mmol)的聚(二甲基硅氧烷-共聚-甲基氢硅烷)(三甲基甲硅烷基封端的,Mw=1500道尔顿,24mol%MeHSiO)和15滴的铂(0)-催化剂在25ml甲苯中反应来制备产物。
得到1.44g的浅棕色树脂,其在数小时之后固化。在研磨时,得到米色粉末。
熔点:79.7℃。
UV(四氢呋喃):λmax=318nm,ε=31300M-1cm-1.
实施例8:合成硅氧烷二(二苯基)三嗪S-8
按照与实施例1相似的方式,通过使1.15g(2.2mmol)的烯丙基二(二苯基)三嗪B-19、0.56g(3.3mmol)三乙氧基硅烷和15滴的铂(0)-催化剂在25ml甲苯中反应来制备产物。
得到0.57g的浅黄色树脂,其在数小时之后固化。在研磨时,得到浅黄色粉末。
熔点:62.23℃。
UV(四氢呋喃):λmax=320nm,ε=75800M-1cm-1。
溶解度:
溶解度的检测:
化合物编号 | 在癸酸/辛酸甘油三酯中的溶解度[重量%] |
(S-1) | 11.7 |
(S-2) | 22.8 |
(S-3) | 26.4 |
(S-5) | 21.7 |
根据本发明的含有硅烷和/或硅氧烷基团的二(二苯基)三嗪衍生物S-1、S-2、S-3和S-5的溶解度数据显示新的二(二苯基)三嗪衍生物是特别高度油溶性的UV吸收剂。
光稳定性:
光稳定性的检测:
评价光稳定性的方法是基于辐照UV-滤光剂的高度稀释的溶液。在一定剂量的辐照之后进行的分析是通过UV光谱法进行的。将UV吸收剂在乙醇中的浓度调节到1·10-5和1·10-6mol/l之间的值,使得在1cm光程长度的吸收池中的溶液的吸收率等于或小于0.2。滤光剂分子的相互保护可以在这些条件下排除。图1显示了用于辐照样品的实验设置,其中:
1:金属卤化物灯(Macam Flexicure),
2:液体导光片,
3:光学试验台,
4:截止滤光片,对于λ>290nm是透明的,
5:装有UV吸收剂溶液的闭合的吸收池,
6:磁力搅拌器
在辐照样品之前,用UV辐照计(RM-12,Dr.Electronic GmbH)检测在样品位置上的UVB强度。这种辐照计是通过使用波长分辨的辐照计(Gamma C11)与金属卤化物灯的光谱输出的检测进行对比来校准的(包括导光片和截止滤光片)。所以,RM-12辐照计的读数与所述灯的相应光谱输出之间的关系是已知的,本领域技术人员能通过检测UVB强度来确定波长分辨的强度。通过改变在导光片末端和吸收池之间的距离,UVB强度可以在100μW/cm2至4500μW/cm2的范围内变化。
对于样品的辐照,使用最高的可能强度(用Macam 103辐照计测得4.5mW/cm2UVB强度)。辐照时间是在0-180分钟内变化。样品在180分钟后接收的剂量对应于60MED。在辐照期间,样品进行搅拌。在特定的辐照间隔之后,在UV光谱仪(Perkin Elmer,Lambda 16)中分析样品。
从在每个辐照剂量下的吸收值,可以使用Lambert-Beer法则计算浓度。为了得到物质的半衰期,对于实验数据进行一级动力学模型的拟合。因为灯的UV光谱和COLIPA标准日光的UV光谱是已知的,可以计算出UV吸收剂在COLIPA标准日光辐照条件下的相应半衰期[Bernd Herzog,Stefan Müller,Myriam Sohn,Uli Osterwalder,“防晒剂的光稳定性的新研究和预测(New Insight and Prediction of Photostablity of Sunscreens)”,Journal 133,26–36(2007)]。
对于一些苯并卓酚(benzotropolone)研究的半衰期值和在辐照(10MED)之后的回收率列在下表中:
化合物编号 | 半衰期[小时] | 在10MED之后的回收率[%] |
(S-1) | 444.4 | 99.6 |
(S-2) | 412.1 | 99.6 |
(S-3) | 282.0 | 99.4 |
(S-4) | 390.7 | 99.6 |
(S-5) | 326.2 | 99.5 |
(S-6) | 363.7 | 99.5 |
(S-7) | 207.7 | 99.2 |
(S-8) | 342.2 | 99.5 |
根据本发明方法的化合物编号S-1,S-2,S-3,S-4,S-5,S-6,S-7和S-8具有高的光稳定性,并且在所有情况下,在10MED的辐照之后回收得到大于99%的硅烷和硅氧烷。
UV屏蔽性能
二(二苯基)三嗪衍生物的UV屏蔽性能是通过检测它们在乙醇中的UV光谱研究的。在下表中,一起列出了研究的吸收最大值(λmax)与相应的A1% 1cm值。
根据本发明的二(二苯基)三嗪化合物编号S-1、S-2、S-3、S-4、S-5、S-6、S-7和S-8在UV区域中具有高屏蔽性能,这由A1% 1cm值大于700表示。
Claims (13)
1.由式(1)表示的硅烷-和硅氧烷-二(二苯基)三嗪衍生物作为UV吸收剂的用途:
(1)
其中
n是1-4的数;
如果n=1,
则X是*-L-Sil;或下式的基团:
L是选自式(2)基团的连接基:
(2)
R1、R2、R3各自独立地是C1-C22烷基;C6-C20芳基;C1-C22烷氧基;
或O-C6-C20芳基;
R4、R5、R6和R7各自独立地是氢;C1-C22烷基;C6-C20芳基;C1-C22烷氧基;或O-C6-C20芳基;
b是0-30的数;
c是0-6的数;和
d是0-1的数;
p是1-250的数;
q是0-250的数;和
Sil、Sil1和Sil2各自独立地是硅烷结构部分、低聚硅氧烷结构部分或聚硅氧烷结构部分;
如果n=2,
则X是式(1a)或(1b)的二价基团:
(1a)或
(1b)
x是2-250的数;
y是0-250的数;和
z是1-50的数;
如果n=3,
则X是含有硅烷结构部分、低聚硅氧烷结构部分或聚硅氧烷结构部分的三价基团;
如果n=4,
则X是式(1c)的四价基团:
(1c)和
A是下式的基团:
2.权利要求1的用途,其中在式(1)中:
n是1-4的数;
如果n=1,
则X是*-L-Sil;
L是选自式(2)基团的连接基:
(2)
R4、R5、R6和R7各自独立地是氢;C1-C22烷基;C6-C20芳基;C1-C22烷氧基;或O-C6-C20芳基;
b是0-30的数;
c是0-6的数;和
d是0-1的数;
Sil、Sil1和Sil2各自独立地是硅烷结构部分、低聚硅氧烷结构部分或聚硅氧烷结构部分;
如果n=2,
则X是式(1a)或(1b)的二价基团:
(1a)或
(1b)
R1、R2、R3各自独立地是C1-C22烷基;C6-C20芳基;C1-C22烷氧基;或O-C6-C20芳基;
x是2-250的数;
y是0-250的数;和
z是1-50的数;
如果n=3,
则X是含有硅烷结构部分、低聚硅氧烷结构部分或聚硅氧烷结构部分的三价基团;
如果n=4,
则X是式(1c)的四价基团:
(1c)和
A是下式的基团:
3.权利要求1或2的用途,其中Sil、Sil1和Sil2各自独立地是选自Si(R1)m[OSi(R2)]o的低聚硅氧烷结构部分;其中:
m是0、1或2,
o是3、2或1;
m和o的总和是3;和
R1和R2各自独立地是C1-C22烷基;C6-C20芳基;C1-C22烷氧基;或O-C6-C20芳基。
4.权利要求1-3中任一项的用途,其中硅烷基团是选自三甲基硅烷、三乙基硅烷、三丙基硅烷、三异丙基硅烷、二甲基叔丁基硅烷、二甲基己基硅烷、三苯基硅烷和二甲基苯基硅烷。
5.权利要求1-4中任一项的用途,其中在式(2)中:
R4和R5各自独立地是氢或C1-C22烷基;
b是1-30的数;和
c和d是0。
6.权利要求5的用途,其中在式(2)中,R4和R5各自独立地是氢或C1-C5烷基。
7.权利要求5或6的用途,其中在式(2)中,R4和R5各自独立地是氢或甲基。
8.权利要求5-7中任一项的用途,其中在式(2)中,b是1-5的数。
9.权利要求1-8中任一项的用途,其中X对应于下式(3):
(3)
其中
“亚烷基”表示直链或支化的C2-C12亚烷基;
R8、R9和R10各自独立地是C1-C22烷基;或C1-C22烷氧基;或式(3a)的基团:
(3a)
R11和R12和R13各自独立地是C1-C22烷基,或C1-C22烷氧基;和e是0-30的数。
10.权利要求1-9中任一项的用途,其中X是下式的基团:
其中
p和q各自独立地是1-20的数。
11.权利要求10的用途,其中p和q各自独立地是3-15的数。
12.由式(1)表示的化合物:
(1)
其中
n是1-4的数;
如果n=1,
则X是*-L-Sil;或下式的基团:
L是选自式(2)基团的连接基:
(2)
R4、R5、R6和R7各自独立地是氢;C1-C22烷基;C6-C20芳基;C1-C22烷氧基;或O-C6-C20芳基;
b是0-30的数;
c是0-6的数;和
d是0-1的数;
p是1-250的数;
q是0-250的数;和
Sil、Sil1和Sil2各自独立地是硅烷结构部分、低聚硅氧烷结构部分或聚硅氧烷结构部分;
如果n=2,
则X是式(1a)或(1b)的二价基团:
(1a)或
(1b)
R1、R2、R3各自独立地是C1-C22烷基;C6-C20芳基;C1-C22烷氧基;或O-C6-C20芳基;
x是2-250的数;
y是0-250的数;和
z是1-50的数;
如果n=3,
则X是含有硅烷结构部分、低聚硅氧烷结构部分或聚硅氧烷结构部分的三价基团;
如果n=4,
则X是式(1c)的四价基团:
(1c)和
A是下式的基团:
13.一种化妆品组合物,其含有根据权利要求1的式(1)的三嗪衍生物和至少一种化妆品可接受的载体。
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