CN102281862A - 包含膦酰基的亚苄基化合物 - Google Patents
包含膦酰基的亚苄基化合物 Download PDFInfo
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- CN102281862A CN102281862A CN2009801543055A CN200980154305A CN102281862A CN 102281862 A CN102281862 A CN 102281862A CN 2009801543055 A CN2009801543055 A CN 2009801543055A CN 200980154305 A CN200980154305 A CN 200980154305A CN 102281862 A CN102281862 A CN 102281862A
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- Prior art keywords
- wat
- alkyl
- sol
- aryl
- substituted
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- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 title description 22
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- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 125000003118 aryl group Chemical group 0.000 claims abstract description 20
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
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- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61K8/55—Phosphorus compounds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Dermatology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
Abstract
本发明涉及式(1)化合物在保护人和动物毛发和皮肤以防UV辐射中的用途,其中R1和R2相互独立地为氢;未被取代或取代的C1-C12烷基;未被取代或取代的C3-C12环烷基;未被取代或取代的C6-C20芳基;或未被取代或取代的C2-C20链烯基;R3为PO3R1R2;COOR6;COR7;CONR7R8;-SO2R6;CN;未被取代或取代的C6-C20芳基;R4为未被取代的C6-C20芳基;或被至少一个C1-C18烷基、C1-C18烷氧基、C3-C12环烷基、羟基、氨基、单-或二-C1-C18烷基氨基、-NR10COR11或式(1a)的基团取代的C6-C20芳基;或未被取代或取代的C4-C20杂芳基;R5为氢;取代或未被取代的C1-C20烷基;未被取代或取代的C3-C12环烷基;未被取代或取代的C6-C20芳基;或未被取代或取代的C4-C20杂芳基;或R4和R5形成脂环族环;R6、R7和R8相互独立地为氢;可以被一个或多个E取代,和/或间隔有一个或多个D的C1-C18烷基或C3-C12环烷基;或可被G取代的C6-C20芳基;或R7和R8一起形成5或6元环;D为-CO-;-COO-;-S-;-SO-;-SO2-;-O-;-NR9-;-SiR12R13-;-POR14-;-CR15=CR16-;或-C≡C-;E为-OR17;-SR17;-NR10R11;-NR10COR11;-COR11;-COOR11;-CONR10R11;-CN;卤素;SO3R18;SO2R18;PO3(R18)2;或PO2(R18)2;G为E;任选间隔有D的C1-C18烷基;C1-C18全氟烷基;任选被E取代和/或间隔有D的C1-C18烷氧基;其中R9、R10和R11相互独立地为氢;任选被C1-C18烷基或C1-C18烷氧基取代的C6-C18芳基;任选间隔有-O-的C1-C18烷基;或R10和R11一起形成5或6元环;R12和R13相互独立地为氢;C1-C18烷基;或任选被C1-C18烷基取代的C6-C18芳基;R14为C1-C18烷基;或任选被C1-C18烷基取代的C6-C18芳基;R15和R16相互独立地为氢;任选被C1-C18烷基或C1-C18烷氧基取代的C6-C18芳基;或任选间隔有-O-的C1-C18烷基;R17为H;任选被C1-C18烷基或C1-C18烷氧基取代的C6-C18芳基;或任选间隔有-O-的C1-C18烷基;且R18为氢;任选被C1-C18烷基或C1-C18烷氧基取代的C6-C18芳基;或任选间隔有-O-的C1-C18烷基。本发明UV过滤剂代表有利地吸收UV-A和UV-B区的油溶性物质。
Description
本发明涉及包含膦酰基的亚苄基化合物在化妆品制剂中的用途。
熟知紫外辐射(光)对人皮肤有害。取决于UV辐射的波长,导致不同类型的皮肤损害。UV-B辐射(约290nm至约320nm)是造成晒斑的原因,并可导致皮肤癌。UV-A辐射(约320nm至约400nm),同时产生皮肤晒黑,还有助于晒斑和诱发皮肤癌。此外,UV-A可加剧UV-B辐射的有害效果。
因此,有效的防晒配制剂优选包含至少一种UV-A和UV-B过滤剂和覆盖约290nm至400nm全部范围的宽频带UV过滤剂以防止人皮肤被日光损害。
不幸的是,许多有效的有机UV过滤剂在一定浓度下具有差的油溶性并倾向于结晶。因此,UV保护效力明显降低。
此外,油溶性UV过滤剂应包括在化妆品防晒护理产品中而对乳液的感官特征不具有任何影响。为此,应保证UV吸收剂在涂布以后留在皮肤上的水脂膜中的最佳分布。
因此,本发明的目的是找到具有关于UV吸收剂的改进性能的UV吸收剂配制剂。
令人惊讶地发现特殊的包含膦酰基的亚苄基化合物具有非常好的作为化妆品UV吸收剂的性能。
因此,本发明涉及式(1)化合物在保护人和动物毛发和皮肤以防UV辐射中的用途:
其中:
R1和R2相互独立地为氢;未被取代或取代的C1-C12烷基;未被取代或取代的C3-C12环烷基;未被取代或取代的C6-C20芳基;或未被取代或取代的C2-C20链烯基;
R3为PO3R1R2;COOR6;COR7;CONR7R8;-SO2R6;CN;未被取代或取代的C6-C20芳基;
R4为未被取代的C6-C20芳基;或被至少一个C1-C18烷基、C1-C18烷氧基、C3-C12环烷基、羟基、氨基、单-或二-C1-C18烷基氨基、-NR10COR11或式(1a)
的基团取代的C6-C20芳基;或未被取代或取代的C4-C20杂芳基;
R5为氢;取代或未被取代的C1-C20烷基;未被取代或取代的C3-C12环烷基;未被取代或取代的C6-C20芳基;或未被取代或取代的C4-C20杂芳基;或
R4和R5形成脂环族环;
R6、R7和R8相互独立地为氢;可以被一个或多个E取代和/或间隔有一个或多个D的C1-C18烷基或C3-C12环烷基;或可被G取代的C6-C20芳基;或
R7和R8一起形成5或6元环;
D为-CO-;-COO-;-S-;-SO-;-SO2-;-O-;-NR9-;-SiR12R13-;-POR14-;-CR15=CR16-;或-C≡C-;
E为-OR17;-SR17;-NR10R11;-NR10COR11;-COR11;-COOR11;-CONR10R11;-CN;卤素;SO3R18;SO2R18;PO3(R18)2;或PO2(R18)2;
G为E;任选间隔有D的C1-C18烷基;C1-C18全氟烷基;任选被E取代和/或间隔有D的C1-C18烷氧基;其中:
R9、R10和R11相互独立地为氢;任选被C1-C18烷基或C1-C18烷氧基取代的C6-C18芳基;任选间隔有-O-的C1-C18烷基;或
R10和R11一起形成5或6元环;
R12和R13相互独立地为氢;C1-C18烷基;或任选被C1-C18烷基取代的C6-C18芳基;
R14为C1-C18烷基;或任选被C1-C18烷基取代的C6-C18芳基;
R15和R16相互独立地为氢;任选被C1-C18烷基或C1-C18烷氧基取代的C6-C18芳基;或任选间隔有-O-的C1-C18烷基;
R17为H;任选被C1-C18烷基或C1-C18烷氧基取代的C6-C18芳基;或任选间隔有-O-的C1-C18烷基;且
R18为氢;任选被C1-C18烷基或C1-C18烷氧基取代的C6-C18芳基;或任选间隔有-O-的C1-C18烷基。
优选下述式(1)化合物,其中:
R1和R2相互独立地为氢;或C1-C12烷基。
还优选下述式(1)化合物,其中:
R3为PO3R1R2;COOR6;COR7;或SO2R6;其中:
R1和R2相互独立地为氢;或未被取代或取代的C1-C12烷基;且
R6和R7相互独立地为未被取代或取代的C1-C18烷基或C6-C20芳基。
还优选下述式(1)化合物,其中:
R1和R2相互独立地为未被取代的C1-C12烷基;
R3为COOR6;且
R6为C1-C5烷基。
还优选下述式(1)化合物,其中:
R5为氢;或C1-C20烷基。
最优选式(2)的化合物:
其中:
R1和R2相互独立地为C1-C5烷基;
R3为-COOR6;SO2R6;PO3R1R2;COR6;未被取代的C6-C10芳基;或被C1-C5烷基或C1-C5烷氧基取代的C6-C10芳基;
R6为C1-C5烷基;或C6-C10芳基;
R19、R20和R21相互独立地为氢;C1-C5烷基;C1-C5烷氧基;氨基;C1-C5二烷基氨基;苯基;或式
的基团。
对应于式(1)的化合物可以为它们的顺式或反式和/或可以为它们的质子化或去质子化形式。
C1-C12烷基表示直链和直链烃基,例如甲基、乙基、丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、2-乙基丁基、正戊基、异戊基、1-甲基戊基、1,3-二甲基丁基、正己基、1-甲基己基、正庚基、异庚基、1,1,3,3-四甲基丁基、1-甲基庚基、3-甲基庚基、正辛基、2-乙基己基、1,1,3-三甲基己基、1,1,3,3-四甲基戊基、壬基、癸基、十一烷基、1-甲基十一烷基或十二烷基。
C1-C12烷氧基为直链或直链基团如甲氧基、乙氧基、丙氧基、丁氧基、戊氧基、己氧基、庚氧基、辛氧基、异辛氧基、壬氧基、十一烷氧基或十二烷氧基。
C3-C12环烷基为未被取代或被一个或多个C1-C4烷基取代的C3-C12环烷基,例如环丙基、环丁基、环戊基、环庚基、环辛基、环壬基、环癸基、环十一烷基、环十二烷基、1-异丙基-4-甲基环己基(DL-薄荷基),最优选环己基。
杂-C3-C12芳基优选为吡啶基、嘧啶基、三嗪基、吡咯基、呋喃基、噻吩基或喹啉基。
C2-C20链烯基例如为烯丙基、异丙烯基、2-丁烯基、3-丁烯基、异丁烯基、正戊-2,4-二烯基、3-甲基-丁-2-烯基、正辛-2-烯基、正十二碳-2-烯基、异十二碳烯基、正十二碳-2-烯基或正十八碳-4-烯基。
C6-C20芳基例如为萘基,优选苯基或联苯基。
各个烷基可以为线性或支化的。各个烷基或环烷基可以为饱和或不饱和的。
各个烷基、环烷基或烷氧基可优选被一个或多个E取代和/或间隔有一个或多个D。
各个芳基可优选被G取代。
各个杂芳基可优选被G、C2-C18链烯基、C2-C18炔基、C7-C25芳烷基或CN取代。
本发明膦酰基化合物的实例列于下表1中:
膦酰基UV吸收剂可根据W.Lehnert在期刊“Tetrahedron”第30卷(1974),第301-305页中描述的程序通过使式(1a)的酮或醛与通式(1b)的膦酰基化合物在四氯化钛和有机碱的存在下反应而制备,其中基团R如上定义。
式(1a)羰基化合物与式(1b)膦酸酯的反应优选在不存在溶剂或在如下溶剂的存在下进行:有机溶剂,更优选醚溶剂如二乙醚、二
烷和四氢呋喃;卤化溶剂如四氯甲烷、氯仿或二氯甲烷,芳族溶剂如甲苯、二甲苯、均三甲基苯和苯;烃溶剂如庚烷,和石油醚,酯溶剂如乙酸乙酯和乙酸甲酯;醇溶剂,例如叔丁醇、正辛醇-(1)和乙二醇;和酰胺溶剂,例如二甲基甲酰胺、二甲基乙酰胺、二乙基乙酰胺、二乙基丙酰胺和1-甲基吡咯烷酮。极性溶剂如二甲亚砜以及这些溶剂的混合物也是合适的。最优选,溶剂选自四氢呋喃、二
烷、四氯甲烷、氯仿和甲苯及其混合物。
缩合反应通过使用四氯化钛或其它合适的路易斯酸促进。路易斯酸的实例例如为三氯化铝、氟化钾、三氯化钛或氯化锌。
在本发明制备方法中,式(1b)亚甲基活性化合物在无机或有机碱的存在下反应。有机碱的典型实例为胺,例如N-甲基吗啉、吗啉、三乙胺、Hünig碱、DBU(1,8-二氮杂双环[5.4.0]十一碳-7-烯)、DBN(1,5-二氮杂双环[4.3.0]壬-5-烯)、对二甲基氨基吡啶和N,N,N’,N’-四甲胍。合适的碱还有醇盐(例如甲醇钠、乙醇钠、叔丁醇钾)。无机碱如NaH、LiOH、碳酸钠、碳酸氢钾和碳酸钾也是合适的。优选使用胺,如N-甲基吗啉、三乙胺、DBU和Hünig碱。
反应温度可以为-78℃至所用溶剂的沸点之间,但优选-10℃至50℃,更优选0-20℃。
式(1b)膦酰基试剂的摩尔比可以为相对于式(1a)羰基衍生物0.1-100倍,优选0.5-10倍,更优选1-2倍。
四氯化钛与式(1b)膦酰基试剂的摩尔比可以为0.5-10倍,优选0.9-5倍,更优选1-2倍。
溶剂的量(质量)可以与式(1a)羰基衍生物质量的0.5-100倍,优选1-50倍,更优选1-10倍一样多。
反应终点可例如通过薄层色谱法、气相色谱法或高效液相色谱法确认。在反应以后,产物式(1)膦酰基衍生物可通过产物分离,例如通过液-液分离、柱色谱,或通过将不良溶剂加入反应混合物中结晶,或通过蒸馏由反应混合物得到。
根据式(1)的膦酰基亚苄基化合物尤其适用作UV过滤剂,即用于保护对紫外线敏感的有机材料,尤其是人和动物皮肤和毛发以防UV辐射作用。这种化合物因此适用作化妆品、药物和兽医学制剂中的光保护剂。这种化合物优选以溶解状态使用。
因此,本发明还涉及一种包含至少一种式(1)化合物和化妆品耐受载体或辅助剂的化妆品制剂。
除本发明UV吸收剂外,化妆品制剂还可包含以下物质类别的一种或多种其它UV保护剂:
1.对氨基苯甲酸衍生物,例如4-二甲基氨基苯甲酸2-乙基己酯;
2.水杨酸衍生物,例如水杨酸2-乙基己酯;
3.二苯甲酮衍生物,例如2-羟基-4-甲氧基二苯甲酮及其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-乙基己基酯和2-氰基丙烯酸3-(苯并呋喃基)酯;
6.3-咪唑-4-基丙烯酸和酯;
7.苯并呋喃衍生物,尤其是2-(对氨基苯基)苯并呋喃衍生物,其描述于EP-A-582 189、US-A-5 338 539、US-A-5 518 713和EP-A-613 893中;
8.聚合UV吸收剂,例如EP-A-709080所述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-乙基己酯和异戊基酯或US-A-5601 811和WO 97/00851所公开的肉桂酸衍生物;
10.樟脑衍生物,例如3-(4′-甲基)亚苄基-莰烷-2-酮、3-亚苄基莰烷-2-酮、N-[2(和4)-2-氧基冰片-3-亚基-甲基)苄基]丙烯酰胺聚合物、3-(4′-三甲基铵)亚苄基-莰烷-2-酮甲基硫酸盐、3,3′-(1,4-亚苯基-二次甲基)-双(7,7-二甲基-2-氧代-双环[2.2.1]庚烷-1-甲烷磺酸)和盐、3-(4′磺基)亚苄基-莰烷-2-酮和盐;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-双(2′-羟基-4′-正辛氧基苯基)-1,3,5-三嗪;2,4-双{[4-(3-(2-丙氧基)-2-羟基-丙氧基)-2-羟基]-苯基}-6-(4-甲氧基苯基)-1,3,5-三嗪;2,4-双{[4-(2-乙基-己氧基)-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-双{[4-(三(三甲基甲硅烷基氧基-甲硅烷基丙氧基)-2-羟基]-苯基}-6-(4-甲氧基苯基)-1,3,5-三嗪;2,4-双{[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-双{[4-(1′,1′,1′,3′,5′,5′,5′-七甲基三甲硅烷基-2″-甲基-丙氧基)-2-羟基]-苯基}-6-(4-甲氧基苯基)-1,3,5-三嗪;2,4-双{[4-(3-(2-丙氧基)-2-羟基-丙氧基)-2-羟基]-苯基}-6-[4-乙基羧基)-苯基氨基]-1,3,5-三嗪;
13.三苯胺基-s-三嗪衍生物,例如2,4,6-三苯胺-(对羰基-2′-乙基-1′-氧基)-1,3,5-三嗪和US-A-5 332 568、EP-A-517 104、EP-A-507 691、WO93/17002和EP-A-570 838所公开的UV吸收剂;
14.2-苯基苯并咪唑-5-磺酸及其盐;
15.邻氨基苯甲酸薄荷酯;
16.TiO2(各种包封的)、ZnO和云母。
“Sunscreens”,N.J.Lowe、N.A.Shaath、Marcel Dekker编辑,Inc.,New York和Basle或Cosmetics&Toiletries(107),第55及随后各页(1992)所述的UV吸收剂也可用作其它UV保护物质。
具体参考下表所述光保护剂:
上述光保护剂,尤其是上表中作为优选描述的光保护剂可以与本发明的UV吸收剂的混合物使用。应当理解除本发明UV吸收剂外,也可使用大于一种其它光保护剂,例如2、3、4、5或6种其它光保护剂。优选使用基于重量1∶99-99∶1,尤其是1∶95-95∶1,优选10∶90-90∶10的本发明UV吸收剂/其它光保护剂的混合比。具有特殊意义的是20∶80-80∶20,尤其是40∶60-60∶40,优选约50∶50的混合比。这种混合物可尤其用于改善溶解性或提高UV吸收。
合适的混合物可尤其有利地用于本发明化妆品组合物中。
合适的新UV过滤剂列于表1中(化合物P-01至P-14)。
这种配制剂中的其它典型成分为防腐剂、杀菌剂和抑菌剂、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制剂的其它典型成分,例如醇、多元醇、聚合物、电解质、有机溶剂、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、防刺激剂和抗炎剂等。
所述化妆品或药物制剂以优异地保护人皮肤以防日光的损害效果而著名。
以下可溶性UV过滤剂的混合物(表2)可与本发明亚苄基化合物一起混合:
以下油溶混性有机UV过滤剂的混合物(表3)可与本发明亚苄基化合物一起混合:
以下水溶性或分散性UV过滤剂的混合物(表4)可与本发明亚苄基化合物一起混合:
UV过滤剂组合实例
在先前表“X”中所列的所有UV过滤剂组合代表具体的UV过滤剂。各个具体UV吸收剂的重量比(基于组合中所有UV吸收剂的重量)可例如为0.01-0.99,尤其是0.1-0.9,优选0.2-0.8(例如0.3)。
其它UV过滤剂组合实例如下:
在先前所列的所有UV过滤剂组合中,UV吸收剂的重量比(基于组合中所有UV吸收剂的重量)为:
(a)对于两种UV吸收剂的组合:
1∶1或1∶2或2∶1或1∶3或3∶1。
(b)对于三种UV吸收剂的组合:
1∶1∶1或1∶2∶1或1∶1∶2或2∶1∶1或1∶2∶2或2∶1∶2或2∶2∶1或1∶3∶1或1∶1∶3或3∶1∶1或1∶3∶3或3∶1∶3或3∶3∶1或1∶2∶3或1∶3∶2或2∶1∶3或2∶3∶1或3∶1∶2或3∶2∶1。
(c)对于四种UV吸收剂的组合:
1∶1∶1∶1或1∶1∶2∶1或1∶1∶1∶2或1∶2∶1∶1或2∶1∶1∶1或1∶1∶1∶3或1∶1∶3∶1或1∶3∶1∶1或3∶1∶1∶1或1∶2∶2∶1或2∶1∶2∶1或2∶2∶1∶1或2∶1∶1∶2或1∶3∶31或3∶1∶3∶1或3∶3∶1∶1或3∶1∶1∶3或1∶2∶3∶1或1∶3∶2∶1或1∶1∶2∶3或1∶1∶3∶2或2∶1∶1∶3或2∶1∶3∶1或2∶3∶1∶1或3∶1∶1.2或3∶2∶1∶1或3∶1∶2∶1。
配制剂实例
在以下配制剂实例中:
新UV过滤剂可以为(如表1所述)P-01或P-02或P-03或P-04或P-05或P-06或P-07或P-08或P-09或P-10或P-11或P-12或P-13或P-14或P-15或P-16。
“UV SOL”可以为(如表2所述)UV SOL 1,或UV SOL 2,或UV SOL3,或UV SOL 4,或UV SOL 5,或UV SOL 6,或UV SOL 7,或UV SOL8,或UV SOL 9,或UV SOL 10,或UV SOL 11,或UV SOL 12,或UVSOL 13,或UV SOL 14,或UV SOL 15,或UV SOL 16,或UV SOL 17,或UV SOL 18,或UV SOL 19,或UV SOL 20,或UV SOL 21,或UV SOL22,或UV SOL 23,或UV SOL 24,或UV SOL 25,或UV SOL 26,或UV SOL 27,或UV SOL 28,或UV SOL 29,或UV SOL 30,或UV SOL31,或UV SOL 32,或UV SOL 33,或UV SOL 34,或UV SOL 35,或UV SOL 36,或UV SOL 37,或UV SOL 38,或UV SOL 39,或UV SOL40,或UV SOL 41,或UV SOL 42,或UV SOL 43,或UV SOL 44,或UV SOL 45,或UV SOL 46,或UV SOL 47,或UV SOL 48,或UV SOL49,或UV SOL 50,或UV SOL 51,或UV SOL 52,或UV SOL 53,或UV SOL 54,或UV SOL 55,或UV SOL 56,或UV SOL 57,或UV SOL58,或UV SOL 59,或UV SOL 60,或UV SOL 61,或UV SOL 62,或UV SOL 63,或UV SOL 64,或UV SOL 65,或UV SOL 66,或UV SOL67,或UV SOL 68,或UV SOL 69,或UV SOL 70,或UV SOL 71,或UV SOL 72,或UV SOL 73,或UV SOL 74,或UV SOL 75,或UV SOL76,或UV SOL 77,或UV SOL 78,或UV SOL 79,或UV SOL 80,或UV SOL 81,或UV SOL 82,或UV SOL 83,或UV SOL 84,或UV SOL85,或UV SOL 86,或UV SOL 87,或UV SOL 88,或UV SOL 89,或UV SOL 90,或UV SOL 91,或UV SOL 92,或UV SOL 93,或UV SOL94,或UV SOL 95,或UV SOL 96,或UV SOL 97,或UV SOL 98,或UV SOL 99,或UV SOL 100,或UV SOL 101,或UV SOL 102,或UV SOL103,或UV SOL 104,或UV SOL 105,或UV SOL 106,或UV SOL 107,或UV SOL 108,或UV SOL 109,或UV SOL 110,或UV SOL 111,或UV SOL 112,或UV SOL 113,或UV SOL 114,或UV SOL 115,或UVSOL 116,或UV SOL 117,或UV SOL 118,或UV SOL 119,或UV SOL120,或UV SOL 121,或UV SOL 122,或UV SOL 123,或UV SOL 124,或UV SOL 125,或UV SOL 126,或UV SOL 127,或UV SOL 128,或UV SOL 129,或UV SOL 130,或UV SOL 131,或UV SOL 132,或UVSOL 133,或UV SOL 134,或UV SOL 135,或UV SOL 136,或UV SOL137,或UV SOL 138,或UV SOL 139,或UV SOL 140,或UV SOL 141,或UV SOL 142,或UV SOL 143,或UV SOL 144,或UV SOL 145,或UV SOL 146,或UV SOL 147,或UV SOL 148,或UV SOL 149,或UVSOL 150,或UV SOL 151,或UV SOL 152,或UV SOL 153,或UV SOL154,或UV SOL 155,或UV SOL 156,或UV SOL 157,或UV SOL 158,或UV SOL 159,或UV SOL 160,或UV SOL 161,或UV SOL 162,或UV SOL 163,或UV SOL 164,或UV SOL 165,或UV SOL 166,或UVSOL 167,或UV SOL 168,或UV SOL 169,或UV SOL 170,或UV SOL171,或UV SOL 172,或UV SOL 173,或UV SOL 174,或UV SOL 175,或UV SOL 176,或UV SOL 177,或UV SOL 178,或UV SOL 179,或UV SOL 180,或UV SOL 181,或UV SOL 182,或UV SOL 183,或UVSOL 184,或UV SOL 185,或UV SOL 186,或UV SOL 187,或UV SOL188,或UV SOL 189,或UV SOL 190,或UV SOL 191,或UV SOL 192,或UV SOL 193,或UV SOL 194,或UV SOL 195,或UV SOL 196,或UV SOL 197,或UV SOL 198,或UV SOL 199,或UV SOL 200,或UVSOL 201,或UV SOL 202,或UV SOL 203,或UV SOL 204,或UV SOL205,或UV SOL 206,或UV SOL 207,或UV SOL 208,或UV SOL 209,或UV SOL 210,或UV SOL 211,或UV SOL 212,或UV SOL 213,或UV SOL 214,或UV SOL 215,或UV SOL 216,或UV SOL 217,或UVSOL 218,或UV SOL 219,或UV SOL 220,或UV SOL 221,或UV SOL222,或UV SOL 223,或UV SOL 224,或UV SOL 225,或UV SOL 226,或UV SOL 227,或UV SOL 228,或UV SOL 229,或UV SOL 230,或UV SOL 231,或UV SOL 232,或UV SOL 233,或UV SOL 234,或UVSOL 235,或UV SOL 236,或UV SOL 237,或UV SOL 238,或UV SOL239,或UV SOL 240,或UV SOL 241,或UV SOL 242,或UV SOL 243,或UV SOL 244,或UV SOL 245,或UV SOL 246,或UV SOL 247,或UV SOL 248,或UV SOL 249,或UV SOL 250,或UV SOL 251,或UVSOL 252,或UV SOL 253;
“UV LIQ”可以为(如表3所述)UV LIQ 1,或UV LIQ 2,或UV LIQ3,或UV LIQ 4,或UV LIQ 5,或UV LIQ 6,或UV LIQ 7,或UV LIQ8,或UV LIQ 9,或UV LIQ 10,或UV LIQ 11,或UV LIQ 12,或UV LIQ13,或UV LIQ 14,或UV LIQ 15,或UV LIQ 16,或UV LIQ 17,或UVLIQ 18,或UV LIQ 19,或UV LIQ 20,或UV LIQ 21,或UV LIQ 22,或UV LIQ 23,或UV LIQ 24,或UV LIQ 25,或UV LIQ 26,或UV LIQ27,或UV LIQ 28,或UV LIQ 29,或UV LIQ 30,或UV LIQ 31,或UVLIQ 32,或UV LIQ 33,或UV LIQ 34,或UV LIQ 35,或UV LIQ 36,或UV LIQ 37,或UV LIQ 38,或UV LIQ 39,或UV LIQ 40,或UV LIQ41,或UV LIQ 42,或UV LIQ 43,或UV LIQ 44,或UV LIQ 45,或UVLIQ 46,或UV LIQ 47,或UV LIQ 48,或UV LIQ 49,或UV LIQ 50,或UV LIQ 51,或UV LIQ 52,或UV LIQ 53,或UV LIQ 54,或UV LIQ55,或UV LIQ 56,或UV LIQ 57,或UV LIQ 58,或UV LIQ 59,或UVLIQ 60,或UV LIQ 61,或UV LIQ 62,或UV LIQ 63,或UV LIQ 64,或UV LIQ 65,或UV LIQ 66,或UV LIQ 67,或UV LIQ 68,或UV LIQ69,或UV LIQ 70,或UV LIQ 71,或UV LIQ 72,或UV LIQ 73,或UVLIQ 74,或UV LIQ 75,或UV LIQ 76,或UV LIQ 77,或UV LIQ 78,或UV LIQ 79,或UV LIQ 80,或UV LIQ 81,或UV LIQ 82,或UV LIQ83,或UV LIQ 84,或UV LIQ 85,或UV LIQ 86,或UV LIQ 87,或UVLIQ 88,或UV LIQ 89,或UV LIQ 90,或UV LIQ 91,或UV LIQ 92,或UV LIQ 93,或UV LIQ 94,或UV LIQ 95,或UV LIQ 96,或UV LIQ97,或UV LIQ 98,或UV LIQ 99,或UV LIQ 100,或UV LIQ 101,或UV LIQ 102,或UV LIQ 103,或UV LIQ 104,或UV LIQ 105,或UV LIQ106,或UV LIQ 107,或UV LIQ 108,或UV LIQ 109,或UV LIQ 110,或UV LIQ 111,或UV LIQ 112,或UV LIQ 113,或UV LIQ 114,或UVLIQ 115,或UV LIQ 116,或UV LIQ 117,或UV LIQ 118,或UV LIQ 119,或UV LIQ 120,或UV LIQ 121,或UV LIQ 122,或UV LIQ 123;
“UV WAT”可以为(如表4所述)UV WAT 1,或UV WAT 2,或UVWAT 3,或UV WAT 4,或UV WAT 5,或UV WAT 6,或UV WAT 7,或UV WAT 8,或UV WAT 9,或UV WAT 10,或UV WAT 11,或UV WAT12,或UV WAT 13,或UV WAT 14,或UV WAT 15,或UV WAT 16,或UV WAT 17,或UV WAT 18,或UV WAT 19,或UV WAT 20,或UV WAT 21,或UV WAT 22,或UV WAT 23,或UV WAT 24,或UV WAT25,或UV WAT 26,或UV WAT 27,或UV WAT 28,或UV WAT 29,或UV WAT 30,或UV WAT 31,或UV WAT 32,或UV WAT 33,或UV WAT 34,或UV WAT 35,或UV WAT 36,或UV WAT 37,或UV WAT38,或UV WAT 39,或UV WAT 40,或UV WAT 41,或UV WAT 42,或UV WAT 43,或UV WAT 44,或UV WAT 45,或UV WAT 46,或UV WAT 47,或UV WAT 48,或UV WAT 49,或UV WAT 50,或UV WAT51,或UV WAT 52,或UV WAT 53,或UV WAT 54,或UV WAT 55,或UV WAT 56,或UV WAT 57,或UV WAT 58,或UV WAT 59,或UV WAT 60,或UV WAT 61,或UV WAT 62,或UV WAT 63,或UV WAT64,或UV WAT 65,或UV WAT 66,或UV WAT 67,或UV WAT 68,或UV WAT 69,或UV WAT 70,或UV WAT 71,或UV WAT 72,或UV WAT 73,或UV WAT 74,或UV WAT 75,或UV WAT 76,或UV WAT77,或UV WAT 78,或UV WAT 79,或UV WAT 80,或UV WAT 81,或UV WAT 82,或UV WAT 83,或UV WAT 84,或UV WAT 85,或UV WAT 86,或UV WAT 87,或UV WAT 88,或UV WAT 89,或UV WAT90,或UV WAT 91,或UV WAT 92,或UV WAT 93,或UV WAT 94,或UV WAT 95,或UV WAT 96,或UV WAT 97,或UV WAT 98,或UV WAT 99,或UV WAT 100,或UV WAT 101,或UV WAT 102,或UV WAT 103,或UV WAT 104,或UV WAT 105,或UV WAT 106,或UV WAT 107,或UV WAT 108,或UV WAT 109,或UV WAT 110,或UV WAT 111,或UV WAT 112,或UV WAT 113,或UV WAT 114,或UV WAT 115,或UV WAT 116,或UV WAT 117,或UV WAT 118,或UV WAT 119,或UV WAT 120,或UV WAT 121,或UV WAT 122,或UV WAT 123,或UV WAT 124,或UV WAT 125,或UV WAT 126,或UV WAT 127,或UV WAT 128,或UV WAT 129,或UV WAT 130,或UV WAT 131,或UV WAT 132,或UV WAT 133,或UV WAT 134,或UV WAT 135,或UV WAT 136,或UV WAT 137,或UV WAT 138,或UV WAT 139,或UV WAT 140,或UV WAT 141,或UV WAT 142,或UV WAT 143,或UV WAT 144,或UV WAT 145,或UV WAT 146,或UV WAT 147,或UV WAT 148,或UV WAT 149,或UV WAT 150,或UV WAT 151,或UV WAT 152,或UV WAT 153,或UV WAT 154,或UV WAT 155,或UV WAT 156,或UV WAT 157,或UV WAT 158,或UV WAT 159,或UV WAT 160,或UV WAT 161,或UV WAT 162,或UV WAT 163,或UV WAT 164,或UV WAT 165,或UV WAT 166,或UV WAT 167,或UV WAT 168,或UV WAT 169,或UV WAT 170,或UV WAT 171,或UV WAT 172,或UV WAT 173,或UV WAT 174,或UV WAT 175,或UV WAT 176,或UV WAT 177,或UV WAT 178,或UV WAT 179,或UV WAT 180,或UV WAT 181,或UV WAT 182,或UV WAT 183,或UV WAT 184,或UV WAT 185,或UV WAT 186,或UV WAT 187,或UV WAT 188,或UV WAT 189,或UV WAT 190,或UV WAT 191,或UV WAT 192,或UV WAT 193,或UV WAT 194,或UV WAT 195,或UV WAT 196,或UV WAT 197,或UV WAT 198,或UV WAT 199,或UV WAT 200,或UV WAT 201,或UV WAT 202,或UV WAT 203,或UV WAT 204,或UV WAT 205,或UV WAT 206,或UV WAT 207,或UV WAT 208,或UV WAT 209,或UV WAT 210,或UV WAT 211,或UV WAT 212,或UV WAT 213,或UV WAT 214,或UV WAT 215,或UV WAT 216,或UV WAT 217,或UV WAT 218,或UV WAT 219,或UV WAT 220,或UV WAT 221,或UV WAT 222,或UV WAT 223,或UV WAT 224,或UV WAT 225,或UV WAT 226,或UV WAT 227,或UV WAT 228,或UV WAT 229,或UV WAT 230,或UV WAT 231,或UV WAT 232,或UV WAT 233,或UV WAT 234,或UV WAT 235,或UV WAT 236,或UV WAT 237,或UV WAT 238,或UV WAT 239,或UV WAT 240,或UV WAT 241,或UV WAT 242,或UV WAT 243,或UV WAT 244,或UV WAT 245,或UV WAT 246,或UV WAT 247,或UV WAT 248,或UV WAT 249,或UV WAT 250,或UV WAT 251,或UV WAT 252,或UV WAT 253,或UV WAT 254,或UV WAT 255,或UV WAT 256,或UV WAT 257,或UV WAT 258,或UV WAT 259,或UV WAT 260,或UV WAT 261,或UV WAT 262,或UV WAT 263,或UV WAT 264,或UV WAT 265,或UV WAT 266,或UV WAT 267,或UV WAT 268,或UV WAT 269,或UV WAT 270,或UV WAT 271,或UV WAT 272,或UV WAT 273,或UV WAT 274,或UV WAT 275,或UV WAT 276,或UV WAT 277,或UV WAT 278,或UV WAT 279,或UV WAT 280,或UV WAT 281,或UV WAT 282,或UV WAT 283,或UV WAT 284,或UV WAT 285,或UV WAT 286,或UV WAT 287,或UV WAT 288,或UV WAT 289,或UV WAT 290,或UV WAT 291,或UV WAT 292,或UV WAT 293,或UV WAT 294,或UV WAT 295,或UV WAT 296,或UV WAT 297,或UV WAT 298,或UV WAT 299,或UV WAT 300,或UV WAT 301,或UV WAT 302,或UV WAT 303,或UV WAT 304,或UV WAT 305,或UV WAT 306,或UV WAT 307,或UV WAT 308,或UV WAT 309,或UV WAT 310,或UV WAT 311,或UV WAT 312,或UV WAT 313,或UV WAT 314,或UV WAT 315,或UV WAT 316,或UV WAT 317,或UV WAT 318,或UV WAT 319,或UV WAT 320,或UV WAT 321,或UV WAT 322,或UV WAT 323,或UV WAT 324,或UV WAT 325,或UV WAT 326,或UV WAT 327,或UV WAT 328,或UV WAT 329,或UV WAT 330,或UV WAT 331,或UV WAT 332,或UV WAT 333,或UV WAT 334,或UV WAT 335,或UV WAT 336,或UV WAT 337,或UV WAT 338,或UV WAT 339,或UV WAT 340,或UV WAT 341,或UV WAT 342,或UV WAT 343,或UV WAT 344,或UV WAT 345,或UV WAT 346,或UV WAT 347,或UV WAT 348,或UV WAT 349,或UV WAT 350,或UV WAT 351,或UV WAT 352,或UV WAT 353,或UV WAT 354,或UV WAT 355,或UV WAT 356,或UV WAT 357,或UV WAT 358,或UV WAT 359,或UV WAT 360,或UV WAT 361,或UV WAT 362,或UV WAT 363,或UV WAT 364,或UV WAT 365,或UV WAT 366,或UV WAT 367,或UV WAT 368,或UV WAT 369,或UV WAT 370,或UV WAT 371,或UV WAT 372,或UV WAT 373,或UV WAT 374,或UV WAT 375,或UV WAT 376,或UV WAT 377。
配制剂实例:
本发明还涉及包含至少一种本发明UV吸收剂的化妆品组合物。化妆品组合物尤其适用作UV过滤剂,即用于保护对紫外线敏感的有机材料,尤其是皮肤和毛发以防UV辐射的有害作用。
UV吸收剂可以以溶解状态或以微粉化状态使用。
化妆品组合物含例如基于组合物的总重量为0.1-30重量%,优选0.1-15重量%,尤其是0.5-10重量%一种或多种UV吸收剂和至少一种化妆品耐受辅助剂。
化妆品组合物可通过使用常规方法,例如通过将各个组分一起简单地搅拌,尤其是通过使用已知化妆品UV吸收剂如OMC,尤其是水杨酸异辛酯的溶解性能将UV吸收剂与辅助剂物理混合而制备。UV吸收剂可例如不进一步处理地,或以微粉化状态,或以粉末形式使用。
化妆品组合物可例如为霜、凝胶、洗剂、醇和水/醇溶液、乳液、蜡/脂肪组合物、棒制剂、粉或软膏。
作为含水和含油乳液(例如W/O、O/W、O/W/O和W/O/W乳液或微乳液),组合物含例如基于组合物的总重量为0.1-30重量%,优选0.1-15重量%,尤其是0.5-10重量%一种或多种UV吸收剂,基于组合物的总重量为1-60重量%,尤其是5-50重量%,优选10-35重量%至少一种油组分,基于组合物的总重量为0-30重量%,尤其是1-30重量%,优选4-20重量%至少一种乳化剂,基于组合物的总重量为10-90重量%,尤其是30-90重量%水,和0-88.9重量%,尤其是1-50重量%其它化妆品耐受辅助剂。
作为含油组合物(例如油、W/O、O/W、O/W/O和W/O/W乳液或微乳液)的油组分,例如考虑基于具有6-18个,优选8-10个碳原子的脂肪醇的Guerbet醇,线性C6-C24脂肪酸与线性C3-C24醇的酯,支化C6-C13羧酸与线性C6-C24脂肪醇的酯,线性C6-C24脂肪酸与支化醇,尤其是2-乙基己醇的酯,羟基羧酸与线性或支化C6-C22脂肪醇的酯,尤其是苹果酸二辛酯,线性和/或支化脂肪酸与多元醇(例如丙二醇、二聚物二醇或三聚物三醇)和/或Guerbet醇的酯,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,C6-C24脂肪醇和/或Guerbet醇与芳族羧酸,尤其是苯甲酸的酯,C2-C12二羧酸与具有1-22个碳原子的线性或支化醇或具有2-10个碳原子和2-6个羟基的多元醇的酯,植物油(例如向日葵油、橄榄油、豆油、菜子油、杏仁油、霍霍巴油、橙油、小麦胚芽油、桃仁油和椰子油的液体组分),支化伯醇,取代的环己烷,线性和支化C6-C22脂肪醇碳酸酯,Guerbet碳酸酯,苯甲酸与线性和/或支化C6-C22醇的酯(例如TN),具有总计12-36个碳原子,尤其是12-24个碳原子的线性或支化、对称或不对称二烷基醚,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、硅油和/或脂族或环烷烃的开环产物。重要的还有脂肪酸与具有3-24个碳原子的醇的单酯。该组物质包括具有8-24个碳原子的脂肪酸如己酸、辛酸、2-乙基己酸、癸酸、月桂酸、异十三烷酸、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(gadoleic acid)、山萮酸和芥酸及其工业级混合物(例如在压力除去天然脂肪和油中,在由Roelen氧化合成还原醛中,或在不饱和脂肪酸二聚中得到的)与醇,例如异丙醇、己醇、辛醇、2-乙基己醇、癸醇、月桂醇、异十三醇、肉豆蔻醇、鲸蜡醇、棕榈油醇、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(gadoleic acid)、山萮醇、芥醇和二十二碳烯醇及其工业级混合物(例如在基于脂肪酸和油或醛的工业级甲基酯高压氢化中由Roelen氧化合成,和在不饱和脂肪醇二聚中作为单体馏分得到的)的酯化产物。尤其重要的是肉豆蔻酸异丙酯、异壬酸C16-C18烷基酯、硬脂酸2-乙基己酯、油酸鲸蜡酯、三辛酸甘油酯、椰油脂肪醇癸酸酯/辛酸酯和硬脂酸正丁酯。可使用的其它油组分为二羧酸酯,例如己二酸二正丁酯、己二酸二(2-乙基己基)酯、琥珀酸二(2-乙基己基)酯和乙酸二异十三烷基酯,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。优选的单-或多元醇为乙醇、异丙醇、丙二醇、己二醇、甘油和山梨醇。也可使用一种或多种烷基羧酸的二-和/或三价金属盐(碱土金属,尤其是Al3+)。
油组分可以以例如基于组合物的总重量为1-60重量%,尤其是5-50重量%,优选10-35重量%的量使用。
任何常用乳化剂可用于组合物。
作为乳液,例如考虑以下组的非离子表面活性剂:
-2-30摩尔氧化乙烯和/或0-5摩尔氧化丙烯与具有8-22个碳原子的线性脂肪醇,与具有12-22个碳原子的脂肪酸,和与烷基中具有8-15个碳原子的烷基苯酚的加成产物,例如鲸蜡硬脂基聚氧乙烯醚-20或鲸蜡硬脂基聚氧乙烯醚-12。
-1-30摩尔氧化乙烯与具有3-6个碳原子的多元醇,尤其是与甘油的加成产物的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及其氧化乙烯加成产物的甘油单酯和二酯和脱水山梨醇单酯和二酯,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硬脂酸脱水山梨醇酯;
-C8-C22烷基-单-和-低聚葡糖苷及其乙氧基化类似物,低聚度为1.1-5,尤其是1.2-1.4是优选的,葡糖优选作为糖组分;
-2-60摩尔,尤其是15-60摩尔氧化乙烯与蓖麻油和/或氢化蓖麻油的加成产物;
-聚酯,尤其是聚甘油酯,例如二异硬脂酰基聚甘油基-3-二异硬脂酸酯、聚甘油基-3-二异硬脂酸酯、二硬脂酸三甘油酯、聚甘油基-2-倍半异硬脂酸酯或聚甘油基二聚酸酯。来自那些物质类中多个的化合物的混合物也是合适的;
-基于线性、支化、不饱和或饱和C6-C22脂肪酸、蓖麻油酸以及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)、烷基糖苷(例如甲基糖苷、丁基糖苷、月桂基糖苷)以及聚糖苷(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-2-蓖麻油酸酯;
-单-、二-和三-烷基磷酸酯以及单-、二-和三-PEG-烷基磷酸酯及其盐;
-羊毛蜡醇;
-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,例如聚硅氧烷多元醇;
-聚硅氧烷/聚烷基/聚醚共聚物和对应的衍生物,例如鲸蜡基聚甲基硅氧烷共聚醇;
-季戊四醇、脂肪酸、柠檬酸和脂肪醇的混合酯(参见DE-A-1 165 574)和/或具有6-22个碳原子的脂肪酸、甲基糖苷和多元醇,优选甘油或聚甘油的混合酯,例如聚甘油基-3-葡糖二硬脂酸酯、聚甘油基-3-葡糖二油酸酯、甲基葡糖二油酸酯或二椰油酰基季戊四醇二硬脂基柠檬酸酯以及
-聚亚烷基二醇。
氧化乙烯和/或氧化丙烯与脂肪醇、脂肪酸、烷基苯酚、脂肪酸的甘油单-和二酯以及脱水山梨醇单-和二酯,或与蓖麻油的加成产物是已知的市售产品。它们通常为同系混合物,其平均烷氧基化度相当于氧化乙烯和/或氧化丙烯与进行其它反应的基质之比。氧化乙烯与甘油的加成产物的C12-C18脂肪酸单-和二酯例如作为化妆品制剂用的脂肪恢复物质由DE-A-2024 051中已知。
C8-C18烷基-单-和-低聚葡糖苷,它们的制备和它们的用途由现有技术已知。它们尤其通过使葡糖或低聚糖与具有8-18个碳原子的伯醇反应而制备。合适的糖苷基包括其中环状糖基配糖键合在脂肪醇上的单糖苷,以及低聚度为至多优选约8的低聚葡糖苷。低聚度为基于常用于这种工业级产品的同系物分布的统计平均值。
也可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”尤其表示分子中带有至少一个季铵基团和至少一个羧酸根和/或硫酸根基团的表面活性化合物。尤其合适的两性离子表面活性剂为所谓的甜菜碱,例如N-烷基-N,N-二甲基铵甘氨酸盐,例如椰油烷基二甲基铵甘氨酸盐,N-酰基氨基丙基-N,N-二甲基铵甘氨酸盐,例如椰油酰基氨基丙基二甲基铵甘氨酸盐,和烷基或酰基中各自具有8-18个碳原子的2-烷基-3-羧甲基-3-羟基乙基咪唑啉,以及椰油酰基氨基乙基羟基乙基羧甲基甘氨酸盐。尤其优选通过CTFA名椰油酰胺丙基甜菜碱已知的脂肪酸酰胺衍生物。同样适用作乳化剂的还有两性表面活性剂。两性表面活性剂应当理解尤其意指除含有C8-C18烷基或-酰基外,分子中还含有至少一个游离氨基和至少一个-COOH或-SO3H基团且能形成内盐的那些。合适的两性表面活性剂包括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-烷基酰胺基丙基甘氨酸、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,其烷基中各自具有约8-18个碳原子。
尤其优选的两性表面活性剂为N-椰油烷基氨基-丙酸盐、椰油酰基氨基乙基氨基丙酸盐和C12-C18酰基肌氨酸。除两性乳化剂外,还考虑季铵乳化剂,尤其优选季酯型的那些,优选甲基季铵化二脂肪酸三乙醇胺酯盐。
非离子乳化剂是优选的。在所述非离子乳化剂中,尤其优选具有8-22个碳原子和4-30个EO单元的乙氧基化脂肪醇。
乳化剂可以以基于组合物的总重量为1-30重量%,尤其是4-20重量%,优选5-10重量%的量使用。然而,原则上也可省去乳化剂的使用。
本发明组合物,例如霜、凝胶、洗剂、醇和水/醇溶液、乳液、蜡/脂肪组合物、棒制剂、粉或如软膏可另外含温和表面活性剂、富脂剂、珠光蜡、稠度调节剂、增稠剂、聚合物、聚硅氧烷化合物、脂肪、蜡、稳定剂、生物源活性成分、除臭活性成分、去头屑剂、成膜剂、膨润剂、其它UV光保护因子、抗氧化剂、水溶助长剂、防腐剂、昆虫驱避剂、自美黑剂、增溶剂、芳香油、着色剂、抑菌剂等作为其它辅助剂和添加剂。
适用作富脂剂的物质例如为羊毛脂和卵磷脂以及聚乙氧基化或丙烯酸化羊毛脂和卵磷脂衍生物、多元醇脂肪酸酯、单酸甘油酯和脂肪酸链烷醇酰胺,后者同时充当泡沫稳定剂。
合适温和表面活性剂,即皮肤尤其好地耐受的表面活性剂的实例包括脂肪醇聚乙二醇醚硫酸盐、单酸甘油酯硫酸盐、磺基琥珀酸单-和/或二-烷基酯、脂肪酸羟乙基磺酸盐、脂肪酸肌氨酸盐、脂肪酸牛磺酸盐、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、烷基酰胺基甜菜碱和/或蛋白质脂肪酸缩合物,后者优选基于小麦蛋白。
作为珠光蜡,考虑例如:亚烷基二醇酯,尤其是乙二醇二硬脂酸酯;脂肪酸链烷醇酰胺,尤其是椰油脂肪酸二乙醇酰胺;偏甘油酯,尤其是硬脂酸单酸甘油酯;多价未被取代或羟基取代的羧酸与具有6-22个碳原子的脂肪醇的酯,尤其是酒石酸的长链酯;脂肪物质,例如总计具有至少24个碳原子的脂肪醇、脂肪酮、脂肪醛、脂肪醚和脂肪碳酸酯,尤其是月桂酮和二硬脂醚;脂肪酸,例如硬脂酸、羟基硬脂酸或山萮酸、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个羟基的多元醇的开环产物,及其混合物。
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,还有偏甘油酯,脂肪酸和羟基脂肪酸。优选这类物质与烷基低聚葡糖苷和/或相同链长的脂肪酸N-甲基葡糖酰胺和/或聚甘油聚-12-羟基硬脂酸酯的组合。
合适的增稠剂例如包括硅胶类型(亲水性硅酸)、多糖,尤其是黄原胶、瓜尔胶、琼脂、海藻酸和甲基纤维素、羧甲基纤维素和羟甲基纤维素,还有相对高分子量脂肪酸聚乙二醇单-和二酯、聚丙烯酸酯(例如来自Goodrich的
或来自Sigma的
)、聚丙烯酰胺、聚乙烯醇和聚乙烯吡咯烷酮,表面活性剂,例如乙氧基化脂肪酸甘油酯,脂肪酸与多元醇如季戊四醇或三羟甲基丙烷的酯,具有限定同系物分布的脂肪醇乙氧基化物和烷基低聚葡糖苷,以及电解质,例如氯化钠或氯化铵。
合适的阳离子聚合物例如为阳离子纤维素衍生物,例如可在PolymerJR
名下由Amerchol得到的季铵化羟甲基纤维素,阳离子淀粉,二烯丙基铵盐与丙烯酰胺的共聚物,季铵化乙烯基吡咯烷酮/乙烯基咪唑聚合物,例如
(BASF),聚乙二醇与胺的缩合物,季铵化骨胶原多肽,例如月桂基二甲基铵羟丙基水解胶原(
L/Grünau),季铵化小麦多肽,聚乙烯亚胺,阳离子聚硅氧烷聚合物,例如酰胺基聚甲基硅氧烷,己二酸与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),例如如FR-A-2 252 840所述的聚氨基聚酰胺,及其交联的水溶性聚合物,阳离子几丁质衍生物,例如任选作为微晶分布的季铵化壳聚糖;二卤代烷基,例如二溴丁烷与双二烷基胺如双二甲基氨基-1,3-丙烷的缩合物,阳离子瓜尔胶,例如来自Celanese的
C-17、C-16,季铵盐聚合物,例如来自Miranol的
A-15、AD-1、
AZ-1。
作为阴离子、两性离子、两性和非离子聚合物,考虑例如乙酸乙烯酯/巴豆酸共聚物、乙烯基吡咯烷酮/乙酸乙烯酯共聚物、乙酸乙烯酯/马来酸丁酯/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、未交联聚丙烯酸和与多元醇交联的聚丙烯酸、丙烯酰胺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酯/甲基丙烯酸2-羟基丙酯、聚乙烯吡咯烷酮、乙烯基吡咯烷酮/乙酸乙烯酯共聚物、乙烯基吡咯烷酮/甲基丙烯酸二甲基氨基乙基酯/乙烯基己内酰胺三聚物以及任选衍生的纤维素醚和聚硅氧烷。
合适的聚硅氧烷化合物例如为二甲基聚硅氧烷、甲基苯基聚硅氧烷、环状聚硅氧烷以及氨基-、脂肪酸-、醇-、聚醚-、环氧-、氟-、糖苷-和/或烷基-改性的聚硅氧烷化合物,其在室温下可以为液体或树脂形式。合适的还有水合硅石聚甲基硅氧烷,其为平均链长为200-300个二甲基硅氧烷单元的聚甲基硅氧烷与氢化硅酸盐的混合物。合适的挥发性聚硅氧烷的详查可另外在Todd等人,Cosm.Toil.91,27(1976)中找到。
脂肪的典型实例为甘油酯,作为蜡,尤其考虑蜂蜡、巴西棕榈蜡、小烛树蜡、褐煤蜡、石蜡、氢化蓖麻油和脂肪酸酯,或在室温下任选与亲水性蜡组合的微晶蜡固体,例如鲸蜡硬脂醇或偏甘油酯。脂肪酸的金属盐,例如镁、铝和/或锌硬脂酸盐或蓖麻油酸盐可用作稳定剂。
生物源活性成分应当理解意指例如生育酚、生育酚乙酸酯、生育酚棕榈酸酯、抗坏血酸、脱氧核糖核酸、松香油、红没药醇、尿囊素、植烷三醇、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配合物。
作为除臭活性成分,考虑例如止汗药,例如水合氯化铝(参见J.Soc.Cosm.Chem.24,281(1973))。在Hoechst AG,Frankfurt(FRG)的商标下,存在市售的,例如对应于式Al2(OH)5Cl×2.5H2O的水合氯化铝,尤其优选使用它(例如参见J.Pharm.Pharmacol.26,531(1975))。除氯水合物外,还可使用羟基乙酸铝和酸性铝/锆盐。酯酶抑制剂可作为其它除臭活性成分加入。这类抑制剂优选为柠檬酸三烷基酯,例如柠檬酸三甲酯、柠檬酸三丙酯、柠檬酸三异丙酯、柠檬酸三丁酯,以及尤其是柠檬酸三乙酯(
CAT,Henkel KGaA,Düsseldorf/FRG),其抑制酶活性,因此降低气味形成。作为酯酶抑制剂考虑的其它物质为甾醇硫酸盐或磷酸盐,例如羊毛甾醇、胆固醇、菜油甾醇、豆甾醇和谷甾醇硫酸盐或磷酸盐,二羧酸及其酯,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、丙二酸和丙二酸二乙基酯,和羟基羧酸及其酯,例如柠檬酸、苹果酸、酒石酸或酒石酸二乙基酯。影响微生物菌丛和杀灭或抑制汗分解细菌生长的抗菌活性成分同样可存在于制剂(尤其是棒制剂)中。实例包括壳聚糖、苯氧基乙醇和氯己定葡糖酸盐。5-氯-2-(2,4-二氯苯氧基)-苯酚(
Ciba Specialty Chemicals Inc.)也证明尤其有效。
作为去头屑剂,可例如使用氯咪巴唑、吡罗克酮乙醇胺盐和吡硫鎓锌。常用成膜剂包括例如壳聚糖、微晶壳聚糖、季铵化壳聚糖、聚乙烯吡咯烷酮、乙烯基吡咯烷酮/乙酸乙烯酯共聚物、含高比例丙烯酸的季纤维素衍生物的聚合物、骨胶原、透明质酸及其盐和类似化合物。作为水相溶胀剂,可使用蒙脱石、粘土矿物、Pemulen以及烷基改性型Carbopol(Goodrich)。其它合适的聚合物和溶胀剂可在Cosm.Toil.108,95(1993)通过R.Lochhead审查中找到。
除主要光保护物质外,还可使用抗氧化剂种类的次要光保护物质,当UV辐射透过皮肤或毛发时,其干扰触发的光化学反应链。这类抗氧化剂的典型实例为氨基酸(例如甘氨酸、组氨酸、酪氨酸、色氨酸)及其衍生物,咪唑(例如尿刊酸)及其衍生物,肽,例如D,L-肌肽、D-肌肽、L-肌肽及其衍生物(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)及其衍生物,绿原酸及其衍生物,硫辛酸及其衍生物(例如二氢硫辛酸),硫代葡糖金、硫尿嘧啶和其它硫醇(例如硫氧环蛋白、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、月桂基、棕榈酰基、油基、γ-亚油基、胆甾醇基和甘油基酯)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、类脂、核苷酸、核苷和盐),以及非常小耐受量(例如pmol-μmol/kg)的亚砜亚胺化合物(例如丁硫氨酸亚砜亚胺、高半胱氨酸亚砜亚胺、丁硫氨酸砜、五-、六-、七-硫氨酸亚砜亚胺),以及(金属)螯合剂(例如α-羟基脂肪酸、棕榈酸、植酸、乳铁传递蛋白),α-羟基烃酸(例如柠檬酸、乳酸、苹果酸),腐植酸、胆汁酸、胆汁提取物、胆红素、胆绿素、EDTA、EGTA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、油酸),叶酸及其衍生物,泛醌和醌醇及其衍生物,维生素C和衍生物(例如抗坏血酸棕榈酸酯、抗坏血酸磷酸镁、抗坏血酸乙酸酯),生育酚和衍生物(例如乙酸维生素E),维生素A和衍生物(例如棕榈酸维生素A),以及苯偶姻的松柏基苯甲酸酯,云香亭酸及其衍生物,α-糖基芸香苷,阿魏酸,亚糠基葡糖醇,肌肽,丁基羟基甲苯,丁基羟基茴香醚,树脂去甲二氢愈创木酸,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,超氧物歧化酶,N-[3-(3,5-二-叔丁基-4-羟基苯基)丙酰基]磺胺酸(及其盐,例如钠盐),锌及其衍生物(例如ZnO、ZnSO4),硒及其衍生物(例如蛋氨酸硒),茋及其衍生物(例如氧化茋、反氧化茋),那些所述活性成分的根据本发明合适的衍生物(盐、酯、醚、糖、核苷酸、核苷、肽和类脂)。也可提到HALS(=“受阻胺光稳定剂”)。存在的抗氧化剂的量通常为基于UV吸收剂的重量0.001-30重量%,优选0.01-3重量%。
为改进流动行为,还可使用水溶助长剂,例如乙醇、异丙醇或多元醇。为此考虑的多元醇优选具有2-15个碳原子和至少两个羟基。
多元醇还可含其它官能团,尤其是氨基,和/或可被氮改性。典型实例如下:
-甘油;
-亚烷基二醇,例如乙二醇、二甘醇、丙二醇、丁二醇、己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,例如二甘油含量为40-50重量%的工业二甘油混合物;
-羟甲基化合物,尤其例如三羟甲基乙烷、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,尤其是烷基中具有1-8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、戊二醇或山梨酸和the Cosmetics Regulations中表6,A部分和B所列的其它物质类别。
作为芳香油,可提到天然和/或合成芳香物质的混合物。天然芳香物质例如为来自花(百合、薰衣草、玫瑰、茉莉、橙花、依兰树)、茎和叶(天竺葵、广藿香、苦柑)、果实(茴香子、芫荽、葛缕子、刺柏)、果皮(香柠檬、柠檬、橙子)、根(肉豆蔻树、当归、芹菜、小豆蔻、芸香木、蔷薇木)、药草和禾草(龙蒿、柠檬草、鼠尾草、百里香)、针叶和嫩枝(云杉、松树、欧洲赤松、中欧山松)、树脂和香脂(阿魏脂、揽香脂、安息香、没药树脂、乳香、防风根)的提取物。还考虑动物原料,例如麝猫香和海狸香。典型的合成芳香物质例如为酯、醚、醛、酮、醇和烃类型的产品。
酯型芳香物质化合物例如为乙酸亚苄酯、异丁酸苯氧基乙酯、乙酸对叔丁基环己酯、乙酸里哪醇酯、乙酸二甲基苄基原酯、乙酸苯基乙酯、苯甲酸里哪醇酯、甲酸苄酯、甘氨酸乙基甲基苯酯、丙酸烯丙基环己酯、丙酸苏合香酯和水杨酸苄酯。醚包括例如苄基乙基醚;醛包括例如具有8-18个烃原子的线性烷醛、柠檬醛、香茅醛、香茅基氧基乙醛、兔耳草醛、羟基柠檬醛、铃兰醛和波洁洪醛(bourgeonal);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、子丁香酚、异子丁香酚、香叶醇、里哪醇、苯乙醇和双缩松油醇;烃主要包括萜烯和香脂。然而,优选使用一起产生吸引人气味的各种芳香物质的混合物。主要用作芳香组分的具有相对低挥发性的香精油也适用作芳香油,例如鼠尾草油、春黄菊油、丁香油、蜂花油、肉桂叶的油、梨莓花油、杜松子油、香根草油、乳香油、格蓬油、岩蔷薇油和杂薰衣草油。优选使用佛手柑油、二氢月桂烯醇、铃兰醛、新铃兰醛、香茅醇、苯乙醇、α-己基肉桂醛、香叶醇、苄基丙酮、兔耳草醛、里哪醇、乙氧基甲氧基环十一烷(boisambrene forte)、龙诞呋喃(ambroxan)、吲哚、二氢茉莉酮酸甲酯(hedione)、sandelice、柠檬油、红桔油、橙油、戊基甘醇酸烯丙酯、cyclovertal、杂薰衣草油、香紫苏油、β-大马酮、波旁天竺葵油、水杨酸环己酯、vertofix coeur、iso-E-Super、Fixolide NP、橡苔、γ-异甲基紫罗兰酮(iraldein gamma)、苯乙酸、乙酸香叶酯、乙酸苄酯、玫瑰醚、romillat、irotyl和floramat单独或为彼此的混合物。
可用作着色剂的是适于并为化妆品目的允许的物质,例如如汇编于出版物“Kosmetische
”of the Farbstoffkommission der DeutschenForschungsgemeinschaft,Verlag Chemie,Weinheim,1984,第81-106页中。着色剂通常以基于总混合物0.001-0.1重量%的浓度使用。
抑菌剂的典型实例为对革兰氏阳性菌具有特效作用的防腐剂,例如2,4,4′-三氯-2′-羟基二苯醚、氯己定(1,6-二(4-氯苯基-双胍基)己烷)或TCC(3,4,4′-三氯碳酰苯胺)。
大量芳香物质和香精油也具有杀菌性能。典型实例为活性成分子丁香酚、薄荷醇和丁香油中的百里酚、薄荷油和百里香油。有意义的天然除臭剂为萜烯醇法呢醇(3,7,11-三甲基-2,6,10-十二碳三烯-1-醇),其存在于梨莓花油中。甘油单月桂酯也证明是抑菌剂。其它抑菌剂存在的量通常基于制剂的固体内容物为0.1-2重量%。
此外,化妆品组合物可含以下组分作为辅助剂:消泡剂,例如聚硅氧烷,表面活性剂,例如马来酸,增溶剂,例如乙二醇、丙二醇、甘油或二甘醇,遮光剂,例如胶乳、苯乙烯/PVP或苯乙烯/丙烯酰胺共聚物,络合剂,例如EDTA、NTA、β-丙氨酸二乙酸或膦酸,推进剂,例如丙烷/丁烷混合物、N2O、二甲醚、CO2、N2或空气,所谓的耦合剂和显色剂组分,例如氧化染料前体,还原剂,例如巯基乙酸及其衍生物、巯基乳酸、半胱胺、巯基苹果酸或α-巯基乙烷磺酸,或氧化剂,例如过氧化氢、溴酸钾或溴酸钠。
作为昆虫驱避剂,考虑例如N,N-二乙基-间-甲苯酰胺、1,2-戊二醇或昆虫驱避剂3535;合适的自美黑剂例如为二羟基丙酮、赤藓酮糖或二羟基丙酮与赤藓酮糖的混合物。
本发明化妆品配制剂含在广泛的化妆品制剂领域中。考虑例如,尤其如下制剂:
-皮肤护理制剂,例如片形式或液体皂、合成清洁剂或洗涤膏形式的皮肤洗涤和清洁制剂,
-沐浴制剂,例如液体(泡沫浴、牛奶浴、淋浴制剂)或固体沐浴制剂,例如洗浴香精块和浴盐;
-皮肤护理制剂,例如护肤乳、多重乳液或护肤油;
-化妆品个人护理制剂,例如日霜或粉霜形式的面部化妆品、扑面粉(疏松或压实的)、胭脂或霜粉底,眼部护理制剂,例如眼影制剂、睫毛油、眼线笔、眼霜或眼部修护霜;唇部护理制剂,例如唇膏、润唇膏、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;
-脚部护理制剂,例如浴足剂、足粉、护足霜或护足膏、专用除臭剂和止汗药或去茧制剂;
-光保护制剂,例如防晒乳、洗剂、霜或油、防晒制剂或防酷热制剂、预鞣制剂或晒后制剂;
-皮肤美黑制剂,例如自美黑霜;
-脱色制剂,例如用于漂白皮肤的制剂或除斑制剂;
-昆虫驱避剂,例如昆虫趋避油、洗剂、喷雾或棒;
-除臭剂,例如除臭喷雾、泵型喷雾、除臭凝胶、棒或滚珠;
-止汗药,例如止汗棒、霜或滚珠;
-用于有斑皮肤清洁和护理的制剂,例如合成清洁剂(固体或液体)、去皮或洗擦制剂或去皮面膜;
-化学形式的脱毛制剂(脱毛),例如脱毛粉、液体脱毛制剂、霜-或糊形式的脱毛制剂、凝胶形式的脱毛制剂或气溶胶泡沫;
-剃须制剂,例如剃须皂、起泡剃须霜、无泡剃须霜、泡沫和凝胶、干剃须用须前制剂、须后制剂或须后水;
-芳香制剂,例如香水(古龙香水、淡香水、香水、清淡香水、香精)、芳香油或香膏;
-化妆品头发处理制剂,例如洗发水和护发素形式的洗发制剂,护发制剂,例如预处理制剂,生发油、定型霜、定型凝胶、润发油、润发精、发膜、头发深层修复制剂、头发结构用制剂,例如用于永久性烫发(热烫、温和烫、冷烫)的烫发制剂,头发拉直制剂、液体头发固定制剂、发用泡沫、发用喷雾、漂白制剂如过氧化氢溶液、亮发洗发水、漂白霜、漂白粉、漂白膏或油,临时性、半永久性或永久性染发剂、含自氧化染料的制剂,或天然染发剂如指甲花或甘菊。
所列最终配制剂可以以广泛的表达形式存在,例如:
-作为W/O、O/W、O/W/O、W/O/W或PIT乳液和所有类型的微乳液的液体制剂形式,
-凝胶形式,
-油、霜、乳或露的形式,
-粉、漆、片剂或粉底的形式,
-棒形式,
-喷雾剂(具有推进气体的喷雾剂或泵型喷雾剂)或气溶胶的形式,
-泡沫形式,或
-糊形式。
作为皮肤用化妆品组合物尤其重要的是光保护制剂,例如防晒乳、洗剂、霜、油、防晒制剂或防酷热制剂、预鞣制剂或晒后制剂,还有皮肤美黑制剂,例如自美黑霜。特别有意义的是防晒霜、防晒露、防晒油、防晒乳和喷雾剂形式的防晒制剂。
作为发用化妆品组合物尤其重要的是上述头发护理制剂,尤其是洗发水、护发素形式的洗发制剂,护发制剂,例如预处理制剂,生发油、定型霜、定型凝胶、润发油、润发精、发膜、头发深层修复制剂、头发拉直制剂、液体头发固定制剂、发用泡沫和发用喷雾。尤其有意义的是洗发水形式的洗发制剂。
洗发水例如具有以下组成:0.01-5重量%本发明UV吸收剂、12.0重量%月桂基聚氧乙烯醚-2硫酸钠、4.0重量%椰油酰胺基丙基甜菜碱、3.0重量%氯化钠,和水加至100%。
例如,尤其可使用以下发用化妆品配制剂:
a1)由本发明UV吸收剂、PEG-6-C10羰基合成醇和脱水山梨醇倍半油酸酯组成的自乳化储存配制剂,向其中加入水和任何所需季铵化合物,例如4%貂油酰胺丙基-二甲基-2-羟乙基氯化铵或季铵盐80;
a2)由本发明UV吸收剂、柠檬酸三丁酯和PEG-20-脱水山梨醇单油酸酯组成的自乳化储存配制剂,向其中加入水和任何所需季铵化合物,例如4%貂油酰胺丙基-二甲基-2-羟乙基氯化铵或季铵盐80;
b)本发明UV吸收剂在三甘醇单丁醚和柠檬酸三丁酯中的季铵盐掺杂溶液;
c)本发明UV吸收剂与正烷基吡咯烷酮的混合物或溶液。
本发明化妆品制剂含基于组合物总重量为0.1-15重量%,优选0.5-10重量%式(1)UV吸收剂或UV吸收剂与化妆品耐受辅助剂的混合物。
化妆品制剂可通过使用常规方法,例如通过将各个组分一起搅拌而将一种或多种UV吸收剂与辅助剂物理混合。
本发明化妆品制剂可配制成油包水或水包油乳液、醇包油洗剂、离子或非离子两性类脂的多孔分散体、凝胶、固体棒或气溶胶配制剂。
作为油包水或水包油乳液,化妆品耐受辅助剂优选含5-50%油相、5-20%乳化剂和30-90%水。油相可包含适于化妆品配制剂的任何油,例如一种或多种烃油、蜡、天然油、硅油、脂肪酸酯或脂肪醇。优选的一元醇或多元醇为乙醇、异丙醇、丙二醇、己二醇、甘油和山梨醇。
对于本发明化妆品制剂,也可使用任何常用乳化剂,例如一种或多种天然衍生物的乙氧基化酯,例如氢化蓖麻油的聚乙氧基化酯,或硅油乳化剂,例如聚硅氧烷多元醇;未乙氧基化或乙氧基化脂肪酸皂;乙氧基化脂肪醇;未乙氧基化或乙氧基化脱水山梨醇酯;乙氧基化脂肪酸;或乙氧基化甘油酯。
化妆品制剂还可包含其它组分,例如软化剂、乳液稳定剂、皮肤保湿剂、皮肤美黑促进剂、增稠剂如黄原胶、保湿剂如甘油、防腐剂、芳香物质和着色剂。
本发明化妆品制剂的特征是对皮肤的优异保护以防日光的损害效果。
本发明膦酰基亚苄基化合物也可用于稳定上述化妆品配制剂的常用成分。例如,本发明膦酰基亚苄基化合物可用于稳定其它UV吸收剂如UV-A过滤剂丁基甲氧基二苯甲酰基甲烷(Parsol 1789,CAS号70356-09-1)。
式(1)的膦酰基亚苄基化合物尤其适用作保护聚合材料的UV过滤剂。UV过滤剂优选用于如WO2006/058856,第4页第20行至第10页第15行所公开的聚合基质中。
本发明聚合基质可包括例如:
单烯烃和二烯烃的聚合物及其混合物,单烯烃和二烯烃相互或与其它乙烯基单体的共聚物,烃树脂,聚苯乙烯,衍生自乙烯基芳族单体的芳族均聚物和共聚物,衍生自聚合物氢化的氢化芳族聚合物,衍生自所述聚合物氢化的氢化芳族聚合物,乙烯基芳族单体的接枝共聚物,含卤素聚合物,例如衍生自α,β-不饱和酸及其衍生物的聚合物、衍生自不饱和醇和胺或其酰基衍生物或缩醛的聚合物,环状醚的均聚物和共聚物,聚缩醛,聚苯醚和聚苯硫醚,和聚苯醚与苯乙烯聚合物或聚酰胺的混合物,聚氨酯,聚酰胺和共聚酰胺,聚脲,聚酰亚胺,聚酰胺-酰亚胺,聚醚酰亚胺,聚酯酰亚胺,聚乙内酰脲和聚苯并咪唑,聚酯,聚碳酸酯和聚酯碳酸酯,聚酮,聚砜,聚醚砜和聚醚酮,衍生自一方面醛,另一方面苯酚、脲和三聚氰胺的交联聚合物,干性和非干性醇酸树脂,衍生自饱和和不饱和二羧酸与多元醇的共聚酯和乙烯基化合物作为交联剂的不饱和聚酯树脂,及其低可燃性含卤素改性物,衍生自取代丙烯酸酯的可交联丙烯酸树脂,例如环氧丙烯酸酯、氨基甲酸酯丙烯酸酯或聚酯丙烯酸酯,与三聚氰胺树脂交联的醇酸树脂、聚酯树脂和丙烯酸树脂,脲树脂,异氰酸酯,异氰脲酸酯,多异氰酸酯或环氧树脂,衍生自脂族、脂环族、杂环或芳族缩水甘油基化合物或天然聚合物的交联环氧树脂。
本发明聚合基质例如用于模制品、滚塑制品、注塑制品、吹塑制品、膜、带、单丝、纤维、无纺布、板型、粘合剂或油灰、表面涂料等中。
例如,本发明PVC应用用于结构制品如屋顶和墙板。本发明聚合基质用于汽车挡风玻璃、其它汽车玻璃和家用和办公室窗户中的聚合物膜中。
本发明亚苄基化合物还用于稳定身体护理和家用产品中,特别用于皮肤护理产品、盆浴和淋浴添加剂、含芳香剂和有气味物质的制剂、护发产品、洁牙剂、除臭和止汗药制剂、装饰性制剂、光保护制剂和含活性成分的制剂中。
身体护理产品可以为霜、膏、糊、泡沫、凝胶、洗剂、粉、粉底、喷雾、棒或气溶胶的形式。它们优选含本发明亚苄基化合物,并任选为与其它光稳定剂在油相或水相或水/醇相中的混合物。
下表列出本发明身体护理产品的典型实例和它们的成分:
身体护理产品 | 成分 |
保湿霜 | 植物油、乳化剂、增稠剂、香料、水、UV吸收剂 |
洗发水 | 表面活性剂、乳化剂、防腐剂、香料、UV吸收剂 |
牙膏 | 清洁剂、增稠剂、增甜剂、芳香剂、着色剂、UV吸收剂 |
润唇膏 | 植物油、蜡、TiO2、UV吸收剂 |
新型家用清洁和处理剂的典型实例为:
家用清洁/家用处理剂 | 成分 |
浓缩洗洁精 | 表面活性剂混合物、乙醇、UV吸收剂、水 |
鞋油 | 蜡、蜡乳化剂、UV吸收剂、水、防腐剂 |
含蜡地板清洁剂 | 乳化剂、蜡、氯化钠、UV吸收剂、水、防腐剂 |
亚苄基化合物通常通过溶于油相或醇或水相中而掺入,其中需要在升高的温度下。
参考以下实施例更具体地描述本发明,然而,这不意欲限制本发明的范围。
在以下实施例中,百分数涉及重量。所用亚苄基的量涉及纯物质。
A.膦酰基UV吸收剂的制备实例
制备化合物(P-1):
膦酰基化合物P-1根据W.Lehnert的Tetrahedron,第30卷,第305页所述方法(A)合成。通过使用6.95g对茴香醛和11.56g膦酰基乙酸三乙酯,以95%(16.32g)的收率得到作为淡黄色的油的所需产物。
制备化合物(P-2):
膦酰基化合物P-2根据W.Lehnert的Tetrahedron,第30卷,第305页所述方法(A)合成。通过使用6.71g对酞醛和23.11g膦酰基乙酸三乙酯,以89%(24.43g)的收率得到作为浅褐色油的所需产物。
制备化合物(P-3):
膦酰基化合物P-3根据W.Lehnert的Tetrahedron,第30卷,第305页所述方法(A)合成。通过使用9.04g 4-二乙基氨基-苯甲醛和12.71g膦酰基乙酸三乙酯,以17%(4.71g)的收率得到作为黄色油的所需产物。
制备化合物(P-4):
膦酰基化合物P-4根据W.Lehnert的Tetrahedron,第30卷,第305页所述方法(A)合成。通过使用9.11g丁香醛和12.33g膦酰基乙酸三乙酯,以40%(7.81g)的收率得到作为淡黄色油的所需产物。熔点:109.6℃。
制备化合物(P-6):
膦酰基化合物P-6根据W.Lehnert的Tetrahedron,第30卷,第305页所述方法(A)合成。通过使用0.85g 4-甲氧基-苯甲醛和2.00g亚甲基二膦酸四乙酯,得到作为浅橙色油的所需产物。
制备化合物(P-7):
膦酰基化合物P-7根据W.Lehnert的Tetrahedron,第30卷,第305页所述方法(A)合成。通过使用4.56g联苯-4-甲醛和6.17g膦酰基乙酸三乙酯,得到作为淡褐色油的所需产物。
制备化合物(P-5):
膦酰基化合物P-5根据W.Lehnert的Tetrahedron,第30卷,第305页所述方法(A)合成。通过使用1.14g联苯-4-甲醛和2.00g亚甲基二膦酸四乙酯,得到0.3g橙褐色晶体的所需产物。
制备化合物(P-17):
膦酰基化合物P-17根据W.Lehnert的Tetrahedron,第30卷,第305页所述方法(A)合成。通过使用5.00g 4-乙酰胺基苯甲醛和6.96g膦酰基乙酸三乙酯,得到4.67g淡黄色液体的所需产物。
制备化合物(P-19):
膦酰基化合物P-20根据W.Lehnert的Tetrahedron,第30卷,第305页所述方法(A)合成。通过使用4.2g 4,4-联苯二甲醛和9.86g膦酰基乙酸三乙酯,得到5.1g米色晶体的所需产物。
制备化合物(P-20):
膦酰基化合物P-21根据W.Lehnert的Tetrahedron,第30卷,第305页所述方法(B)合成。通过使用9.01g 9-芴酮和22.42g膦酰基乙酸三乙酯,得到6.0g黄色晶体的所需产物。
制备化合物(P-21):
膦酰基化合物P-22根据W.Lehnert的Tetrahedron,第30卷,第305页所述方法(A)合成。通过使用5.00g香草醛和7.44g膦酰基乙酸三乙酯,得到6.37g橙褐色晶体的所需产物。
制备化合物(P-22):
膦酰基化合物P-23根据W.Lehnert的Tetrahedron,第30卷,第305页所述方法(A)合成。通过使用8.50g 3,4,5-三甲氧基-苯甲醛和9.71g膦酰基乙酸三乙酯,得到11.78g无色晶体的所需产物。
耐光性
耐光性的测量
用于评估耐光性的方法基于照射高度稀释的UV过滤剂溶液。在特定剂量的照射以后通过UV光谱进行分析。将乙醇中UV吸收剂的浓度调整1·10-5与1·10-6摩尔/升之间的值,使得在1cm光程长度的吸收池中溶液的吸收率等于或小于0.2。在这种条件下可排出过滤剂分子的互防。图1显示照射试样的实验装置。
在照射试样以前,用UV-辐射计(RM-12,Dr.
Electronic GmbH)测量试样位置上的UVB强度。将该辐射计通过与使用波长分解辐射计(Gamma C11)测量金属卤化物灯(包括光导和截止滤波器)的光谱输出而标定。因此,RM-12辐射计的读数与对应灯的光谱输出的关系是已知的,人们能通过测量UVB强度确定波长分解强度。通过改变光导与吸收池末端之间的距离,UVB强度可在100-4500μW/cm2范围内变化。
对于试样照射,使用可能的最高强度(4.5mW/cm2UVB强度,用Macam103辐射计测量的)。照射时间为由0至180分钟变化。在180分钟以后试样接收的剂量相当于60MED。在照射期间搅拌试样。在特定照射间隔以后,在UV光谱仪(Perkin Elmer,Lambda 16)中分析试样。
可使用朗伯-比尔定律由各个照射剂量下的吸收率值计算浓度。为得到物质的半衰期,将一级动力学模型拟合实验数据。由于灯的UV光谱和COLIPA标准日光的UV光谱是已知的,人们可计算出在COLIPA标准日光照射条件下相应的UV吸收剂半衰期[Bernd Herzog,Stefan Müller,Myriam Sohn,Uli Osterwalder,“New Insight and Prediction ofPhotostablity of Sunscreens”,
Journal 133,26-36(2007)]。
某些具体苯并环庚三烯酚酮的评估半衰期数值和照射(10MED)后的回收率列于下表中:
化合物编号 | 半衰期[小时] | 10MED以后的回收率[%] |
(P-1) | 14311 | 100 |
(P-2) | 172 | 98.8 |
(P-3) | 320 | 99.5 |
(P-4) | 100 | 98.3 |
(P-5) | 7 | 78 |
(P-6) | 11285 | 99.98 |
(P-7) | 466.6 | 99.6 |
(P-17) | 947.6 | 99.8 |
(P-19) | 220.6 | 99.2 |
(P-20) | 449.2 | 99.6 |
(P-22) | 262.8 | 99.3 |
本发明化合物P-1、P-2、P-3、P-4、P-6和P-7具有非常高的耐光性,在一些情况下大于98%膦酸亚芳基酯在10MED照射后被回收。对于化合物P-1和P-7,在10MED照射后,甚至没有观察到光降解。
UV屏蔽性能
通过测量它们在乙醇中的UV光谱评估双联苯三嗪衍生物的UV屏蔽性能。在下表中列出所评估的最大吸收(λ最大)以及对应的A1% 1cm值。
本发明膦酰基化合物P-1、P-2、P-3、P-6和P-7在UV区中具有良好的屏蔽性能,如500以上的A1% 1cm值所示。膦酰基化合物P-1、P-2、P-3、P-4、P-5、P-6和P-7显示出宽吸收带,因此覆盖UV范围的宽区域并提供对UV范围的宽区域的保护。
应用实施例
应用实施例1:
O/W防晒配制剂A
生产指导:
分别制备A部分和B部分并加热至75℃。在提高的搅拌下,将B部分掺入A部分中并用Ultra Turrax以10000rpm均化10秒。在搅拌下冷却至室温。在室温下将pH调整至5.80-6.20。
通过将乳液在石英板上涂布成20μm厚的膜测定丁基甲氧基二苯甲酰基甲烷的耐光性。使用太阳模拟器照射膜2小时(5400kJ/m2)。在照射以后,将石英板投入5ml四氢呋喃中。然后使用高性能液相色谱测定UV-A过滤剂丁基甲氧基二苯甲酰基甲烷的量。测定残余丁基甲氧基二苯甲酰基甲烷为42%。
O/W防晒配制剂B(比较)
配制剂如关于配制剂A所述制备。
如关于配制剂A所述测定比较配制剂B中丁基甲氧基二苯甲酰基甲烷的耐光性。测定残余丁基甲氧基二苯甲酰基甲烷为4%。这意味着通过膦酰基亚苄基化合物(P-01)显著稳定丁基甲氧基二苯甲酰基甲烷至少10个因子。
应用实施例2:
O/W防晒配制剂A
生产指导:
分别制备A部分和B部分并加热至75℃。在提高的搅拌下,将B部分掺入A部分中并用Ultra Turrax以10000rpm均化10秒。在搅拌下冷却至室温。在室温下将pH调整至5.80-6.20。
通过将乳液在石英板上涂布成20μm厚的膜测定UV-B过滤剂甲氧基肉桂酸乙基己酯的耐光性。使用太阳模拟器照射膜4小时(10800kJ/m2)。在照射以后,将石英板投入5ml四氢呋喃中。然后使用高性能液相色谱测定UV-B过滤剂甲氧基肉桂酸乙基己酯的量。测定残余甲氧基肉桂酸乙基己酯为59%。
O/W防晒配制剂B(比较)
配制剂如关于配制剂A所述制备。
如以上关于配制剂A所述测定比较配制剂B中甲氧基肉桂酸乙基己酯的耐光性。测定残余甲氧基肉桂酸乙基己酯为38%。这意味着通过膦酰基亚苄基化合物(P-01)显著稳定甲氧基肉桂酸乙基己酯至少1.55个因子。
Claims (9)
1.式(1)化合物在保护人和动物毛发和皮肤以防UV辐射中的用途:
其中:
R1和R2相互独立地为氢;未被取代或取代的C1-C12烷基;未被取代或取代的C3-C12环烷基;未被取代或取代的C6-C20芳基;或未被取代或取代的C2-C20链烯基;
R3为PO3R1R2;COOR6;COR7;CONR7R8;-SO2R6;CN;未被取代或取代的C6-C20芳基;
R4为未被取代的C6-C20芳基;或被至少一个C1-C18烷基、C1-C18烷氧基、C3-C12环烷基、羟基、氨基、单-或二-C1-C18烷基氨基、-NR10COR11或式(1a)
的基团取代的C6-C20芳基;或未被取代或取代的C4-C20杂芳基;
R5为氢;取代或未被取代的C1-C20烷基;未被取代或取代的C3-C12环烷基;未被取代或取代的C6-C20芳基;或未被取代或取代的C4-C20杂芳基;或
R4和R5形成脂环族环;
R6、R7和R8相互独立地为氢;可以被一个或多个E取代和/或间隔有一个或多个D的C1-C18烷基或C3-C12环烷基;或可被G取代的C6-C20芳基;或
R7和R8一起形成5或6元环;
D为-CO-;-COO-;-S-;-SO-;-SO2-;-O-;-NR9-;-SiR12R13-;-POR14-;-CR15=CR16-;或-C≡C-;
E为-OR17;-SR17;-NR10R11;-NR10COR11;-COR11;-COOR11;-CONR10R11;-CN;卤素;SO3R18;SO2R18;PO3(R18)2;或PO2(R18)2;
G为E;任选间隔有D的C1-C18烷基;C1-C18全氟烷基;任选被E取代和/或间隔有D的C1-C18烷氧基;其中:
R9、R10和R11相互独立地为氢;任选被C1-C18烷基或C1-C18烷氧基取代的C6-C18芳基;任选间隔有-O-的C1-C18烷基;或
R10和R11一起形成5或6元环;
R12和R13相互独立地为氢;C1-C18烷基;或任选被C1-C18烷基取代的C6-C18芳基;
R14为C1-C18烷基;或任选被C1-C18烷基取代的C6-C18芳基;
R15和R16相互独立地为氢;任选被C1-C18烷基或C1-C18烷氧基取代的C6-C18芳基;或任选间隔有-O-的C1-C18烷基;
R17为H;任选被C1-C18烷基或C1-C18烷氧基取代的C6-C18芳基;或任选间隔有-O-的C1-C18烷基;且
R18为氢;任选被C1-C18烷基或C1-C18烷氧基取代的C6-C18芳基;或任选间隔有-O-的C1-C18烷基。
2.根据权利要求1的用途,其中:
R1和R2相互独立地为氢;或C1-C12烷基。
3.根据权利要求1或2的用途,其中:
R3为PO3R1R2;COOR6;COR7;或SO2R6;其中:
R1和R2相互独立地为氢;或未被取代或取代的C1-C12烷基;且
R6和R7相互独立地为未被取代或取代的C1-C18烷基或C6-C20芳基。
5.根据权利要求1-4中任一项的用途,其中:
R5为氢;或C1-C20烷基。
7.包含至少一种或多种根据权利要求1的式(1)化合物以及化妆品耐受载体或辅助剂的化妆品制剂。
8.根据权利要求7的制剂,其包含其它UV保护剂。
9.根据权利要求1-6中任一项的用途,其中式(1)化合物在化妆品配制剂中用于稳定其它UV过滤剂。
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CH558203A (de) | 1971-06-23 | 1975-01-31 | Ciba Geigy Ag | Verfahren zum schuetzen von nicht-textilen materialien gegen ultraviolettstrahlung. |
ZA941088B (en) * | 1993-02-19 | 1995-09-27 | Symphar Sa | Substituted ketophosphonates the processes for their preparation and pharmaceutical compositions containing them |
EP1515694A1 (en) | 2002-06-25 | 2005-03-23 | DSM IP Assets B.V. | Benzoxazole and benzodiazole uv-a sunscreens |
AU2003270693A1 (en) | 2002-09-19 | 2004-04-08 | Ilex Oncology Research, Sarl | Substituted ketophosphonate compounds having bone anabolic activity |
US7618956B2 (en) * | 2005-05-31 | 2009-11-17 | The Gillette Company | Reduction of hair growth |
-
2009
- 2009-11-04 US US13/127,988 patent/US8529877B2/en not_active Expired - Fee Related
- 2009-11-04 ES ES09744413.7T patent/ES2609291T3/es active Active
- 2009-11-04 KR KR1020117013301A patent/KR101550085B1/ko active IP Right Grant
- 2009-11-04 EP EP09744413.7A patent/EP2355791B1/en active Active
- 2009-11-04 BR BRPI0922089A patent/BRPI0922089B1/pt not_active IP Right Cessation
- 2009-11-04 KR KR1020137023077A patent/KR20130103633A/ko not_active Application Discontinuation
- 2009-11-04 CN CN200980154305.5A patent/CN102281862B/zh not_active Expired - Fee Related
- 2009-11-04 JP JP2011535966A patent/JP5559186B2/ja not_active Expired - Fee Related
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN105669746A (zh) * | 2016-01-13 | 2016-06-15 | 高廷梅 | 一种二芳基磷酸酯类化合物的合成方法 |
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JP2012508712A (ja) | 2012-04-12 |
KR101550085B1 (ko) | 2015-09-03 |
BRPI0922089A2 (pt) | 2015-12-15 |
KR20110086728A (ko) | 2011-07-29 |
ES2609291T3 (es) | 2017-04-19 |
EP2355791B1 (en) | 2016-09-28 |
WO2010054966A3 (en) | 2011-08-11 |
BRPI0922089B1 (pt) | 2017-05-16 |
KR20130103633A (ko) | 2013-09-23 |
JP5559186B2 (ja) | 2014-07-23 |
US8529877B2 (en) | 2013-09-10 |
US20110212039A1 (en) | 2011-09-01 |
WO2010054966A2 (en) | 2010-05-20 |
CN102281862B (zh) | 2015-04-15 |
EP2355791A2 (en) | 2011-08-17 |
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