CN101932302B - 微粉化有机紫外线吸收剂的研磨助剂 - Google Patents
微粉化有机紫外线吸收剂的研磨助剂 Download PDFInfo
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- CN101932302B CN101932302B CN2008801257218A CN200880125721A CN101932302B CN 101932302 B CN101932302 B CN 101932302B CN 2008801257218 A CN2008801257218 A CN 2008801257218A CN 200880125721 A CN200880125721 A CN 200880125721A CN 101932302 B CN101932302 B CN 101932302B
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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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- 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
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Abstract
制备包含(a)微粉化的不溶性有机紫外线吸收剂的组合物的方法,该方法包括在研磨装置中在研磨助剂存在下研磨粗粒形式的该不溶性有机紫外线吸收剂,所述研磨助剂选自(b1)羧酸及其盐;(b2)脂肪酸酯;(b3)烷基磷酸盐或磷酸酯;(b4)乙氧基化的羧酸或聚乙二醇(PEG)酯;(b5)脂肪醇的脂肪醇聚乙二醇(PEG)醚;(b6)饱和或不饱和的C4-C28脂肪酸的聚乙二醇/聚丙二醇醚;(b7)乙氧基化的烷基酚或乙氧基化的烷基苯基醚;(b8)多元醇的酯和单酸甘油酯、甘油二酯或甘油三酯;(b9)脂肪酸和蔗糖的酯;(b10)饱和和/或不饱和的C6-C22脂肪酸和环氧乙烷基团的失水山梨糖醇单酯和二酯;和(b11)主要充当清洁剂或净化剂的表面活性剂。
Description
本发明涉及制造紫外线吸收剂的新型制剂的方法和它们在防晒组合物中的用途,所述防晒组合物又特别可用于保护人皮肤。
长期已知的是,长期暴露在到达地表的紫外线辐射中会导致形成红斑或光皮肤病,以及提高的皮肤癌发生率或加速的皮肤老化。
已经提出包括旨在对抗紫外线辐射的材料的各种防晒制剂,由此抑制对皮肤的所述不合意的作用。
许多化合物已被提议用作防晒制剂中的紫外线防护剂,尤其是可溶性有机紫外线吸收剂和不溶性微粉化无机化合物,特别是氧化锌和二氧化钛。
不溶性无机化合物(例如氧化锌和二氧化钛)的高比重造成含有它们的制剂的稳定性降低。此外,已经指出,这类无机化合物在光的影响下产生有毒的自由基(″Redox Mechanisms in Heterogeneous Photocatalysis″,Serpone等人,Electrochemistry in Colloids and Dispersions,编辑Mackay和Texter,VCH Publishers Inc.,NewYork 1992)。
微粉化的不溶性有机紫外线吸收剂在用在防晒制剂中时提供了优异的紫外线防护,并具有高SPF指数。此外,微粉化的不溶性有机紫外线吸收剂没有表现出在光的影响下产生可破坏人皮肤或使人皮肤变敏感的自由基的趋势。
因此,本发明提供了制备包含(a)微粉化的不溶性有机紫外线吸收剂的组合物的方法,该方法包括在研磨装置中在研磨助剂(b)存在下研磨粗粒形式的该不溶性有机紫外线吸收剂,所述研磨助剂(b)选自由下述物质组成的组:
(b1)羧酸及其盐;
(b2)脂肪酸酯;
(b3)烷基磷酸盐或磷酸酯;
(b4)乙氧基化的羧酸或聚乙二醇(PEG)酯;
(b5)脂肪醇的脂肪醇聚乙二醇(PEG)醚;
(b6)饱和或不饱和的C4-C28脂肪酸的聚乙二醇/聚丙二醇醚;
(b7)乙氧基化的烷基酚或乙氧基化的烷基苯基醚;
(b8)多元醇的酯和单酸甘油酯、甘油二酯或甘油三酯;
(b9)脂肪酸和蔗糖的酯;
(b10)饱和和/或不饱和的C6-C22脂肪酸和环氧乙烷基团的失水山梨糖醇单酯和二酯;和
(b11)主要充当清洁剂或净化剂的表面活性剂。
优选地,所述微粉化的不溶性有机紫外线吸收剂选自下式的化合物:
R1和R5彼此独立地为氢;C1-C18烷基;或C6-C12芳基;
R2、R3和R4彼此独立地为氢;或式(1c)的基团,其中基团R2、R3和R4中的至少一个是式(1c)的基团;
R6、R7、R8、R9和R10彼此独立地为氢;羟基;卤素;C1-C18烷基;C1-C18烷氧基;C6-C12芳基;联苯基;C6-C12芳氧基;C1-C18烷基硫代;羧基;-COOM;C1-C18-烷基羧基;氨基羰基;或单-C1-C18烷基氨基或二-C1-C18烷基氨基;C1-C10酰氨基;-COOH;
M是碱金属离子;
x是1或2;且
y是2至10的数。
更优选地,所述不溶性紫外线吸收剂选自式(2)的化合物,
R1、R5、R6、R7和R8如式(1)中所定义,且R1和R5优选是氢。
优选地,在式(1)和(2)中,R6和R8是氢;且
R7是氢;羟基;C1-C5烷基;C1-C5烷氧基;-COOM;-COOH;或COOR10;
M是碱金属离子;且
R10是C1-C5烷基。
在本发明的方法中最优选的是式(3)的化合物:
此外,本发明中所用的微粉化的不溶性紫外线吸收剂选自下式的化合物:
T1是任选被苯基取代的C1-C18烷基;更优选是C1-C8烷基。
最优选的是下式的微粉化的紫外线吸收剂:
此外,本发明中所用的微粉化的不溶性紫外线吸收剂选自下式的化合物:
R11和R12彼此独立地为C1-C20烷基;C2-C20链烯基;C3-C10环烷基;C3-C10环烯基;或R11和R12与连接的氮原子一起形成5元或6元杂环;
n1是1至4的数;
当n1=1时,
R13是饱和或不饱和的杂环基团;羟基-C1-C5烷基;任选被一个或多个C1-C5烷基取代的环己基;任选被杂环基团、氨基羰基或C1-C5烷基羧基取代的苯基;
当n1是2时,
n2是1至3的数;
当n1是3时,
R13是烷三基(alkantriyl)基团;
当n1是4时,
R13是烷四基(alkantetrayl)基团;
A2是-O-;或-N(R15)-;且
R15是氢;C1-C5烷基;或羟基-C1-C5烷基。
在本发明的方法中最优选的是下式的微粉化的不溶性紫外线吸收剂:
其中
C1-20烷基是指直链或支链的、未取代或取代的烷基,例如甲基、乙基、丙基、异丙基、正丁基、正己基、环己基、正癸基、正十二烷基、正十八烷基、二十烷基、甲氧基乙基、乙氧基丙基、2-乙基己基、羟乙基、氯丙基、N,N-二乙基氨基丙基、氰基乙基、苯乙基、苄基、对叔丁基苯乙基、对叔辛基苯氧基乙基、3-(2,4-二-叔戊基苯氧基)-丙基、乙氧基羰基甲基-2-(2-羟基乙氧基)乙基或2-呋喃基乙基。
C2-C20链烯基有例如烯丙基、甲代烯丙基、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、正十二-2-烯基、异十二烯基、正十二-2-烯基或正十八-4-烯基。
C3-C10环烷基有例如环丙基、环丁基、环戊基、环庚基、环辛基、环壬基或环癸基,且优选是环己基。这些基团可以例如被一个或多个相同或不同的C1-C4烷基、优选甲基、和/或羟基取代。如果环烷基被一个或多个基团取代,它们优选被一个、两个或四个、优选被一个或两个相同或不同的基团取代。
C3-C10环烯基有例如环丙烯基、环丁烯基、环戊烯基、环庚烯基、环辛烯基、环壬烯基或环癸烯基,优选是环己烯基。这些基团可以被一个或多个相同或不同的C1-C4烷基、优选甲基、和/或羟基取代。如果环烯基被一个或多个基团取代,它们优选被一个、两个、三个或四个、优选被一个或两个相同或不同的基团取代。
羟基取代的C1-C5烷基有例如羟甲基、羟乙基、羟丙基、羟丁基或羟戊基。
亚烷基优选是C1-C12亚烷基,例如亚甲基、亚乙基、亚丙基、亚丁基、亚己基或亚辛基。
该亚烷基可任选被一个或多个C1-C5烷基取代。
如果R1和R2是杂环基团,它们包含一个、两个、三个或四个相同或不同的环杂原子。特别优选的是含有一个、两个或三个、尤其是一个或两个相同或不同的杂原子的杂环。该杂环可以是单环或多环的,例如单环、双环或三环的。它们优选是单环或双环的,尤其是单环的。这些环优选含有5、6或7个环元。作为式(1)或(2)化合物中出现的基团的来源的单环和双环杂环体系的实例有例如吡咯、呋喃、噻吩、咪唑、吡唑、1,2,3-三唑、1,2,4-三唑、吡啶、哒嗪、嘧啶、吡嗪、吡喃、噻喃、1,4-二氧杂环己烷、1,2-噁嗪、1,3-噁嗪、1,4-噁嗪、吲哚、苯并噻吩、苯并呋喃、吡咯烷、哌啶、哌嗪、吗啉和硫代吗啉。
本发明中所用的微溶性有机化合物以微粉态存在,并优选通过湿磨法制备。
作为用于制备该微溶性微粉化有机化合物的研磨装置,可以使用,例如,喷射磨机、球磨机、振动磨机或锤磨机,优选高速混合磨机。再更优选的磨机是现代球磨机;这些类型的磨机的制造商是例如Netzsch(LMZ磨机)、Drais(DCP-Viscoflow或Cosmo)、Bühler AG(离心磨机)或Bachhofer。
优选在研磨助剂存在下将本发明中所用的不溶性有机紫外线吸收剂微粉化。
优选可用的研磨助剂是可用作分散剂的任何表面活性成分。这类表面活性成分可包含阴离子型、非离子型或两性或/和阳离子型表面活性剂,或其混合物。
基于紫外线防护组合物的总重量,研磨助剂优选以0.1至20重量%、优选1至15重量%的浓度使用。
优选的研磨助剂是羧酸及其盐(b1),例如:
-有机基皂,例如直链C6-C24脂肪酸(癸酸/辛酸、肉豆蔻酸、棕榈油酸、异硬脂酸、亚油酸、花生酸、山萮酸、芥酸)或支链羧酸或羟基羧酸;
最优选的是月桂酰乳酰乳酸钠(sodium lauroyl lactylate)。
其它优选的研磨助剂是脂肪酸酯(b2),例如:
-直链C3-C7或C23-C24脂肪醇与烷基中具有6至11个碳原子或多于22个碳原子的直链脂肪酸的酯。
最优选的是异硬脂酸异十六烷基酯或油酸乙二醇酯。
另一优选的研磨助剂(b3)是烷基磷酸盐或磷酸酯;例如油基聚氧乙烯(3)醚磷酸酯DEA盐。
另一优选的研磨助剂(b4)是乙氧基化的羧酸或聚乙二醇(PEG)酯,例如PEG-n酰化产物,除PEG-n硬脂酸酯、PEG-n油酸酯、PEG-n椰油酸酯外,其中羧酸具有含8至22个碳原子的乙氧基化或未乙氧基化的烷基,例如丁酸、己酸、辛酸、癸酸、月桂酸、肉豆蔻酸、肉豆蔻脑酸、棕榈酸、棕榈油酸、亚油酸、花生酸、花生四烯酸、山萮酸、二十碳五烯酸、芥酸或二十碳六烯酸。
最优选的是月桂酸聚乙二醇(20)酯。
另一优选的研磨助剂(b5)是脂肪醇的脂肪醇聚乙二醇(PEG)醚。
其中直链或支链脂肪醇具有8至22个碳原子(异丙基、乙基己基、癸酰基/辛酰基、异十三烷基、十四烷基、十六烷基(palmoleyl)、异十八烷基、十八碳二烯基(linoyl)、十八碳三烯基(linolenyl)、二十烷基、二十二烷基或二十二碳烯基(erucyl))。
最优选的是十六烷基聚氧乙烯(10)醚、月桂基聚氧乙烯(7)醚或山萮基聚氧乙烯(10)醚(山萮醇聚醚-10)。
另一优选的研磨助剂(b7)是乙氧基化的烷基酚或乙氧基化的烷基苯基醚,例如壬基酚聚氧乙烯(10)醚。
另一优选的研磨助剂(b8)是多元醇的酯和单酸甘油酯、甘油二酯或甘油三酯,例如PEG-10聚甘油-2月桂酸酯。
另一优选的研磨助剂(b9)是脂肪酸和蔗糖的酯,例如PEG-120甲基葡萄糖二油酸酯或聚甘油-3甲基葡萄糖二硬脂酸酯。
另一优选的研磨助剂(b10)是饱和和/或不饱和脂肪酸的失水山梨糖醇单酯和二酯,例如失水山梨糖醇聚氧乙烯(20)醚异硬脂酸酯和失水山梨糖醇聚氧乙烯(20)醚油酸酯。
另一优选的研磨助剂(b11)是通常充当清洁剂或净化剂的表面活性剂。下面列出实例:
A.阴离子型表面活性剂
阴离子型表面活性剂由于存在带负电荷的脂肪部分而获此名。这类离子化残基可以是羧酸根、硫酸根、磺酸根或磷酸根。
阴离子型表面活性剂的通式是:
RX-M+,其中
R是指碳链长度;
X:是带负电荷的物类,例如羧酸根(RCOO-)、硫酸根(ROSO2O-)、磺酸根(RSO2O-)或磷酸根(ROPO(OH)O-)
M是中和基团,如钠、铵、TEA或镁。
a.硫酸酯;硫酸和盐
最优选的是二椰油酰乙二胺PEG-15硫酸钠(sodium dicocoylethylenediamine PEG-15 sulfate)。
b.磺酸酯;磺酸和盐
酰基羟乙基磺酸盐,例如酰基羟乙基磺酸钠、椰油基羟乙基磺酸钠、烷基芳基磺酸盐,例如烷基苯磺酸钠、十二烷基苯磺酸钠;烷基磺酸盐,例如烷基醚磺酸钠(C12-15 pareth-15磺酸钠);C14-C16烯烃磺酸钠、癸基葡糖苷羟丙基磺酸钠,或十二烷基葡糖苷羟丙基磺酸钠。
最优选的是羟丙基磺酸盐。
c.磺基丁二酸酯;磺基丁二酸和盐
最优选的是烷基酰氨基PEG-n磺基丁二酸二钠(油酰氨基MEA-磺基丁二酸二钠)。
d.磷酸酯;磷酸和盐
PEG-n烷基磷酸盐,例如油醇聚醚-10磷酸酯DEA盐、二PEG-n烷基磷酸盐(二酯),例如二月桂基聚氧乙烯(4)醚磷酸酯。
e.酰氨基酸和盐
酰基谷氨酸盐,例如二-TEA棕榈酰天冬氨酸盐、氢化牛脂谷氨酸钠;硬脂酰谷氨酸钠;酰基肽,例如棕榈酰基水解乳蛋白、椰油基水解大豆蛋白钠、TEA-椰油基水解胶原;肌氨酸盐或acyl sarcosides,例如肉豆蔻酰肌氨酸、月桂酰肌氨酸钠、肉豆蔻酰肌氨酸钠、TEA-月桂酰肌氨酸盐;牛磺酸盐和甲基酰基牛磺酸钠,例如月桂酰牛磺酸钠或甲基椰油基牛磺酸钠。
B.非离子型表面活性剂
氧化胺
实例是椰油酰氨基丙基胺氧化物或月桂基胺氧化物。
C.两性或两性离子表面活性剂
在强酸性介质中带有正电荷、在强碱性介质中带有负电荷并在中间pH值下形成两性离子物类的表面活性剂。
a.酰基/二烷基乙二胺
实例是酰基两性二丙酸二钠、酰基两性羟丙基磺酸钠、酰基两性二乙酸二钠、酰基两性丙酸钠。
D.阳离子型表面活性剂
带有正电荷的表面活性剂;由于调理和抗静电作用,是主要的有用的护发品。
a.烷基胺
例如二甲基烷基胺(二甲基月桂胺)、二羟乙基烷基胺二油酸酯、酰氨基丙基二甲基胺月桂酸酯(椰油酰氨基丙基二甲基胺月桂酸酯)
b.烷基咪唑啉
例如烷基羟乙基咪唑啉、乙基羟甲基油基噁唑啉、烷基氨基乙基咪唑啉
c.季化合物
实例是二烷基二甲基氯化铵(羟乙基鲸蜡基二甲基氯化铵)、烷基酰氨基丙基烷基二甲基铵甲苯磺酸盐(椰油酰氨基丙基乙基二甲基铵乙基硫酸盐)。
另一优选的研磨助剂(b12)是有机硅或有机取代的聚硅氧烷,即,具有直链或环状、支链或交联结构、不定的分子量并基本基于其中硅原子通过氧原子彼此连接(硅氧烷键SiOSi)的重复结构单元的任何有机硅聚合物或低聚物,任选取代的烃基经由碳原子直接连接到硅原子上。
D.含硅的化合物
a.硅烷醇化合物或聚二甲基硅氧烷醇
下述通式的被羟基(-OH)封端的二甲基硅氧烷:
b.有机硅弹性体及树脂
硅氧烷结构的交联,例如聚二甲基硅氧烷
弹性体:中等交联,具有允许分子伸长/变形的密度。我们不得不排除PEG-改性的聚二甲基硅氧烷交联聚合物。
树脂:高度交联,具有为该分子提供一定刚度的密度。
c.作为辅助乳化剂体系的有机硅弹性体
在环五硅氧烷中的聚二甲基硅氧烷交联聚合物;DC 9045有机硅弹性体掺混物(Dow Corning);在聚二甲基硅氧烷中的聚二甲基硅氧烷交联聚合物;DC 9041有机硅弹性体掺混物(Dow Corning);与C3至C20烷基聚二甲基硅氧烷/乙烯基聚二甲基硅氧烷交联聚合物交联的聚二甲基硅氧烷(q.v.)的聚合物;DC 9506粉末(Dow Corning);在环五硅氧烷中的聚二甲基硅氧烷/乙烯基聚二甲基硅氧烷交联聚合物;SFE 839(GEsilicones)或KSG 15(Shin-Etsu);与乙烯基二甲基聚硅氧烷交联的二甲基聚硅氧烷的共聚物。
d.树脂有机硅
实例是分散剂,例如KP-545(Shin-Etsu);在环五硅氧烷中的丙烯酸酯/聚二甲基硅氧烷共聚物;聚二甲基硅氧烷和一种或多种单体(丙烯酸、甲基丙烯酸或它们的简单酯之一)的共聚物;甲硅烷氧基硅酸盐,例如三甲基甲硅烷氧基硅酸盐;T-树脂;T-单元的支链聚合物;Q-树脂;Q-单元的支链聚合物:
成膜和抗水剂,例如三甲基甲硅烷氧基硅酸盐;SR 399(GE Silicones)或Wacker-Belsil TMS803(Wacker Chemie);来自Dow Corning的混合物,如DC 749美容液(在环五硅氧烷中的三甲基甲硅烷氧基硅酸盐)或DC 593液(在聚二甲基硅氧烷中的三甲基甲硅烷氧基硅酸盐);烷基改性的硅氧烷(AMS);AMS改进可涂铺性和抗洗除性。
对于无机防晒剂,其改进粒子分散,减轻再附聚和改善在皮肤上的持久效果。
下述通式的烷基聚二甲基硅氧烷:
其中
R是-(CH2)n-CH3
例如:双-苯基丙基聚二甲基硅氧烷(SF 1555液;GE Silicone)下述通式的烷基聚甲基硅氧烷:
R是-(CH2)n-CH3。
有机硅蜡,如DC 2503美容蜡(Dow Corning);硬脂酰聚二甲基硅氧烷;DC 2502液(Dow Corning);鲸蜡基聚二甲基硅氧烷;DC AMS-C30蜡(Dow Corning);C30-C45烷基聚甲基硅氧烷;DC 580蜡(DowCorning);硬脂氧基三甲基硅烷和硬脂醇
同样合适的是simethicones,其是平均链长为200至300个二甲基硅氧烷单元的聚二甲基硅氧烷与氢化的硅酸酯/盐的混合物。另外,在Cosm.Toil.91,27(1976)中可以找到Todd等人关于合适的挥发性有机硅的详细综述。
特别适用于这类乳状液的有机硅乳化剂是符合下式的那些:
其中
m是1至20的数;
n是0至500的数;且
p是0至50的数;
R1是直链或支链C1-C30烷基或苯基;
R2是-CcH2c(-O-C2H4)a-(-O-C3H6)b-(-O-C4H8)d-R3;
R3是H、-OH;直链或支链C1-C12烷基、直链或支链C1-C6烷氧基或直链或支链C2-C12酰氧基;-NHCH2CH2COOM;任选在胺官能上被取代的氨基烷基;-NHCO(CH2)d-COOM、C1-C30羧基酰基;
M是H;Na;K;Li;NH4;或有机胺;任选取代的膦酰基;-NHCO(CH2)dOH;NH3Y;
Y是一价有机或无机阴离子,例如Cl、Br、硫酸根、羧酸根(乙酸根、乳酸根、柠檬酸根);
a是0至100的数;
c是0至5的数;
b是0至50的数;和
d是0至10的数。
这些化合物代表氧化烯化的有机改性有机硅。所用的其它术语是PEG/PPG聚二甲基硅氧烷(聚二甲基硅氧烷共聚醇)或有机硅聚醚,它们明确表现出乳化所必需的表面活性。
特别推荐的优选的有机硅乳化剂符合式
其中
R是直链或支链C1-C30烷基或苯基;
R2是-CcH2c-(-O-C2H4)a-(-O-C3H6)b-O(-C4H8)d-R3;
n是1至500的数;且
R3、a、b、c和d具有如上所述的相同含义。
最优选的是聚二甲基硅氧烷PEG/PPG-7/4磷酸盐。
任选在该紫外线防护组合物中加入有助于长期使该组合物稳定的流变改性剂(组分(c))。
流变改性剂的实例是合成聚合物、天然聚合物和它们的衍生物、矿物聚合物等,以及根据它们的离子特性,如下表中所列的阴离子型、阳离子型、非离子型或两性的:
最优选的流变改性剂是黄原胶、无定形二氧化硅或改性淀粉。
适用于制备微粒的任何已知方法可用于制备该微粉化紫外线吸收剂,例如:
-湿磨(可泵送的分散体的低粘度微粉化法),在球磨机中使用硬研磨介质,例如硅酸锆,和在水或在合适的有机溶剂中的保护性表面活性剂或保护性聚合物;
-使用连续或非连续(分批)捏合机的湿捏合(不可泵送的糊料的高粘度微粉化法)。对于湿捏合法,可以使用溶剂(水或化妆上可接受的油)、研磨助剂(表面活性剂、乳化剂)和聚合研磨助剂。
这两种方法都可优选使用。
-由合适的溶剂(例如水性悬浮液或含有机溶剂的悬浮液)、或在水、乙醇、二氯乙烷、甲苯或N-甲基吡咯烷酮等中的真溶液喷雾干燥。
-通过溶解着紫外线过滤剂的超临界流体(例如,CO2)根据RESS法(超临界溶液快速膨胀)的膨胀,或液态二氧化碳与一种或多种紫外线过滤剂在合适的有机溶剂中的溶液一起膨胀;
-通过从合适的溶剂(包括超临界流体)中再沉淀(GASR法=气体逆溶剂重结晶/PCA法=用压缩逆溶剂沉淀)。
作为用于制备微粉化有机紫外线吸收剂的研磨装置,可以使用,例如,喷射磨机、球磨机、振动磨机或锤磨机,优选高速混合磨机。再更优选的磨机是现代球磨机;这些类型的磨机的制造商是例如Netzsch(LMZ磨机)、Drais(DCP-Viscoflow或Cosmo)、Bühler AG(离心磨机)或Bachhofer。该研磨优选用研磨助剂进行。
用于制备微粉化有机紫外线吸收剂的捏合装置的实例是典型的sigma桨叶分批捏合机,以及连续分批捏合机(IKA-Werke)或连续捏合机(来自Werner und Pfleiderer的Continua)。
微粉化紫外线防护分散体的制备的优选实例
对于微粉化紫外线防护分散体的各实例,制造法如下运行:
将式(7)、(5)或(3)的化合物分别在球磨机(如上所述)中与作为研磨辅助的硅酸锆球(直径0.1至4毫米)、分散剂(如实施例A1至A19中所述)和含有水、多元醇和防腐体系的连续相一起研磨至100纳米至170纳米的d50平均粒度。在分别获得式(7)、(5)或(3)的紫外线吸收剂的微颜料分散体后,配制者根据实施例A1至A19中提到的浓度加入增稠剂。
微粉化紫外线防护分散体的其它优选的制备如下详述:
对于微粉化紫外线防护分散体的各实例,该制造法如下运行:
将式(7)的化合物在球磨机(如上所述)中与作为研磨辅助的硅酸锆球(直径0.1至4毫米)、分散剂(如分散体20至34中所述)和含有水、simethicone、有时含柠檬酸的连续相一起研磨至100纳米至170纳米的d50平均粒度。在获得式(7)的紫外线吸收剂的微颜料分散体后,配制者根据分散体20至34中提到的浓度加入增稠剂(黄原胶)。
紫外线吸收剂组合物优选包含:
(a)0.1至25重量%的本发明的微粉化的不溶性有机紫外线吸收剂分散体;和任选地
(b)化妆上可接受的载体。
本发明的紫外线吸收剂组合物可包含一种或多于一种的如表3和4中所述的附加紫外线吸收剂。
优选使用按重量计1∶99至99∶1、优选1∶95至95∶1、最优选10∶90至90∶10的根据本发明的式(1)、(2)或(3)的化合物和任选如表1和2中所述的附加紫外线吸收剂的混合比。
尤其有用的是20∶80至80∶20、最优选40∶60至60∶40的混合比。
该化妆品或药物制品可以是,例如,霜、凝胶、洗液、酒精溶液和水/酒精溶液、乳状液、蜡/脂肪组合物、条状制品、粉末或油膏。除上文提到的紫外线过滤剂外,该化妆品或药物制品还可以含有下述其它辅助剂。
作为含水和含油的乳状液(例如W/O、O/W、O/W/O和W/O/W乳状液或微乳状液),所述制品含有,例如,基于该组合物总重量的0.1至30重量%、优选0.1至15重量%、尤其0.5至10重量%的一种或多种紫外线吸收剂、基于该组合物总重量的1至60重量%、尤其5至50重量%、优选10至35重量%的至少一种油组分、基于该组合物的总重量的0至30重量%、尤其1至30重量%、优选4至20重量%的至少一种乳化剂、基于该组合物总重量的10至90重量%、尤其30至90重量%的水、和基于该组合物总重量的0至88.9重量%、尤其1至50重量%的其它化妆上可接受的辅助剂。
本发明的化妆品或药物组合物/制品还可以含有一种或多种附加化合物,例如脂肪醇、脂肪酸的酯、天然或合成的甘油三酸酯,包括甘油酯和衍生物、珠光蜡、烃油、有机硅或硅氧烷、有机取代的富脂剂、表面活性剂、稠度调节剂/增稠剂和流变改性剂、聚合物、生物源活性成分、除臭活性成分、抗头屑剂、抗氧化剂、水溶助长剂、防腐剂和抑菌剂、香精油、着色剂、作为spa增强剂的聚合珠或中空球体。
化妆品或药物制品
化妆品或药物制剂包含在多种化妆制品中。例如,尤其考虑下述制品:
-皮肤护理制品,例如片剂或液体皂、无皂洗涤剂或洗涤膏形式的皮肤洗涤和清洁制品,
-沐浴制品,例如液体(泡沫浴、乳液、淋浴制品)或固体沐浴制品,例如洗浴香精块和浴盐;
-皮肤护理制品,例如润肤乳状液、多重乳状液或润肤油;
-化妆个人护理制品,例如日霜或粉霜、擦面粉(散粉或粉饼)、胭脂或粉底霜形式的面部彩妆,眼部护理制品,例如眼影制品、睫毛膏、眼线、眼霜或眼线膏;唇部护理制品,例如唇膏、唇彩、唇线笔;指甲护理制品,如指甲油、洗甲油、指甲硬化剂或去死皮剂;
-足部护理制品,例如足浴剂、足粉、护足霜或足部香膏、专用除臭剂和止汗剂或去茧制品;
-光防护制品,如防晒乳、液、霜或油、防晒隔离霜或tropicals、晒前制品或晒后制品;
-皮肤美黑制品,例如美黑霜;
-脱色素制品,例如皮肤漂白制品或皮肤增亮制品;
-驱虫剂,例如驱虫油、液、喷雾或条;
-除臭剂,如除臭喷雾、泵作用喷雾剂、除臭凝胶、条或滚抹装;
-止汗剂,例如止汗条、霜或滚抹装;
-清洁和护理粉刺皮肤的制品,例如合成洗涤剂(固体或液体)、去角质或磨砂制品或去角质面膜;
-化学形式的除毛制品(脱毛),例如除毛粉、液体除毛制品、霜或糊形式的除毛制品、凝胶形式或气溶胶形式的除毛制品;
-剃须制品,例如剃须皂、泡沫剃须膏、非泡沫剃须膏、泡沫和凝胶、干剃须用的须前制品、须后水或须后液;
-芳香制品,例如香水(eau de Cologne、eau de toilette、eau deperfume、perfume de toilette、perfume)、香精油或香膏;
-美容护发制品,例如香波和护发素形式的洗发制品,护发制品,例如预处理制品、生发油、造型霜、定型胶、润发脂、洗发液、发膜、强效护发品,头发定型制品,例如烫发(热烫、温和烫、冷烫)用的烫发制品、直发制品、液态头发定型制品、头发定型泡沫、头发定型喷雾、漂白制品,例如,过氧化氢溶液,增亮香波、漂白霜、漂白粉、漂白膏或油、临时、半永久或永久染发剂、含自氧化染料的制品、或天然染发剂,如指甲花或甘菊。
呈现形式
所列最终制剂可以以多种呈现形式存在,例如:
-液体制品,如W/O、O/W、O/W/O、W/O/W或PIT乳状液和所有种类的微乳状液形式,
-凝胶形式,
-油、霜、乳或液形式,
-粉末、漆、片或彩妆形式,
-条形式,
-喷雾剂(含推进剂气体的喷雾剂或泵作用喷雾剂)或气溶胶形式,
-泡沫形式,或
-糊形式。
作为皮肤化妆制品,特别重要的是光防护制品,例如防晒乳、液、霜、油、防晒隔离霜或热带用品、晒前制品或晒后制品,以及皮肤美黑制品,例如美黑霜。特别有意义的是防晒霜、防晒液、防晒乳和喷雾形式的防晒制品。
作为头发化妆制品,特别重要的是上述护发制品,尤其是香波、护发素形式的洗发制品,头发护理制品,例如预处理制品、生发油、造型霜、定型胶、润发脂、洗发液、发膜、强效护发品,直发制品、液态头发定型制品、头发定型泡沫和头发定型喷雾。特别有意义的是香波形式的洗发制品。
香波具有例如下述组成:0.01至5重量%的本发明的紫外线吸收剂组合物、12.0重量%的月桂基聚氧乙烯(2)醚-硫酸钠、4.0重量%的椰油酰氨基丙基甜菜碱、3.0重量%的氯化钠和加至100%的水。
这类制剂中的其它典型成分是防腐剂、杀菌剂和抑菌剂、香精、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、抗刺激剂和抗炎剂等等。
本发明的化妆制品以优异的防止日光对人皮肤的破坏作用为特征。
体外评估防晒系数测量值(SPF)的方法
在PMMA板上的最终产品涂施率1.4毫克/平方厘米
使用Labsphere UV-1000S透射比分析仪分析紫外线透射比
其中Eλ=红斑作用光谱;Sλ=太阳光谱辐照度,Tλ=样品的光谱透射比。
体外评估UVA防护系数(UVA PF)的方法
使用Labsphere UV-1000S透射比分析仪分析紫外线透射比
经由太阳模拟器,例如Atlas Suntest CPS+的预照射步骤(为了将防晒产品的光稳定性计入考虑)
其中Tλ=在波长λ下的防晒产品透射比,Tm=在UVA范围内的透射比数据的算术平均值
B.化妆制剂
制造指南:
通过合并所有成分,制备A部分,然后在中速下搅拌并加热至75℃。制备C部分并加热至75℃。在此温度下,在渐进搅拌速度下将A部分倒入C部分中。在65℃以下,分开加入B部分的成分。在中等搅拌下冷却至40℃后,加入D部分。将该混合物以10000rpm均化30秒。
制造指南:
通过合并所有成分,制备A部分,然后在中速下搅拌并加热至75℃。制备C部分并加热至75℃。在此温度下,在渐进搅拌速度下将A部分倒入C部分中。在65℃以下,分开加入B部分的成分。在中等搅拌下冷却至40℃后,加入D部分。然后检查pH值并用三乙醇胺调节。
制造指南:
通过合并所有成分,制备A部分,然后在中速下搅拌并加热至75℃。制备C部分并加热至75℃。在此温度下,在渐进搅拌速度下将A部分倒入C部分中。在65℃以下,分开加入B部分的成分。在中等搅拌下冷却至40℃后,加入D部分。然后,将E部分添加到形成的乳状液中并检查pH值和用三乙醇胺调节。
制造指南:
通过合并所有成分,制备A部分,然后在中速下搅拌并加热至75℃。制备C部分并加热至75℃。在此温度下,在渐进搅拌速度下将A部分倒入C部分中。在65℃以下,分开加入B部分的成分。在中等搅拌下冷却至40℃后,加入D部分。然后检查pH值并用三乙醇胺调节。
制造指南:
通过合并所有成分,制备A部分,然后在中速下搅拌并加热至75℃。制备C部分并加热至75℃。在此温度下,在渐进搅拌速度下将A部分倒入C部分中。在65℃以下,分开加入B部分的成分。在中等搅拌下冷却至40℃后,加入D部分。然后,将E部分添加到形成的乳状液中并检查pH值和用氢氧化钠调节。
制造指南:
通过合并所有成分,制备A部分,然后在中速下搅拌并加热至75℃。制备C部分并加热至75℃。在此温度下,在渐进搅拌速度下将A部分倒入C部分中。在65℃以下,分开加入B部分的成分。在中等搅拌下冷却至40℃后,加入D部分。然后检查pH值并用三乙醇胺调节。
制造指南:
通过合并所有成分,制备A部分,然后在中速下搅拌并加热至75℃。制备C部分并加热至75℃。在此温度下,在渐进搅拌速度下将A部分倒入C部分中。在65℃以下,分开加入B部分的成分。在中等搅拌下冷却至40℃后,加入D部分。然后检查pH值并用氢氧化钠调节。
制造指南:
通过合并所有成分,制备A部分,然后在中速下搅拌并加热至75℃。制备C部分并加热至75℃。在此温度下,在渐进搅拌速度下将A部分倒入C部分中。在65℃以下,分开加入B部分的成分。在中等搅拌下冷却至40℃后,加入D部分。
制造指南:
通过合并所有成分,制备A部分,然后在中速下搅拌并加热至75℃。制备C部分并加热至75℃。在此温度下,在渐进搅拌速度下将A部分倒入C部分中。在65℃以下,分开加入B部分的成分。在中等搅拌下冷却至40℃后,加入E和D部分。然后,加入香料并检查pH值。
制造指南:
通过合并所有成分,制备A部分,然后在中速下搅拌并加热至75℃。制备C部分并加热至75℃。在此温度下,在渐进搅拌速度下将A部分倒入C部分中。在65℃以下,分开加入B部分的成分。在中等搅拌下冷却至40℃后,加入D部分。
制造指南:
通过合并所有成分,制备A部分,然后在中速下搅拌。制备D部分。在室温下,在渐进搅拌速度下将A部分倒入D部分中。在65℃以下,分开加入C部分的成分。然后检查和调节pH值。
制造指南:
通过合并所有成分,制备A部分,然后在中速下搅拌并加热至75℃。制备C部分并加热至75℃。在此温度下,在渐进搅拌速度下将A部分倒入C部分中。在均化该混合物后立即在搅拌下倒入D部分。在65℃以下,分开加入B部分的成分。在中等搅拌下冷却至40℃后,加入E部分。然后,检查pH值。
制造指南:
通过合并所有成分,制备A部分,然后在中速下搅拌并加热至75℃。制备B部分并加热至75℃。在此温度下,在渐进搅拌速度下将A部分倒入B部分中。在65℃以下,分开加入C部分的成分。在中等搅拌下冷却至40℃后,加入E部分。然后,检查pH值。
制造指南:
通过合并所有成分,制备A部分,然后在中速下搅拌。制备D部分。在渐进搅拌速度下将A部分倒入D部分中。在均化该混合物后立即在搅拌下倒入C部分。通过专用于连续喷雾系统的方法,将B部分添加到该混合物中。
制造指南:
通过合并所有成分,制备A部分,然后在中速下搅拌。制备C部分。在室温下,在渐进搅拌速度下将A部分倒入C部分中。在中等搅拌下将D部分并入先前获得的混合物中。然后分开加入B部分的成分。然后检查和调节pH值。
制造指南:
通过合并所有成分,制备A部分,然后在中速下搅拌并加热至75℃。制备C部分并加热至75℃。在此温度下,在渐进搅拌速度下将C部分倒入A部分中。在65℃以下,分开加入B部分的成分。在中等搅拌下冷却至40℃后,加入D部分。然后,检查pH值。
制造指南:
通过合并所有成分,制备A部分,然后在中速下搅拌。制备C部分并加热至60℃。在此温度下,在渐进搅拌速度下将C部分倒入A部分中。然后分开加入B部分的成分。
制造指南:
通过合并所有成分,制备A部分,然后在中速下搅拌。制备C部分并加热至60℃。在此温度下,在渐进搅拌速度下将C部分倒入A部分中。然后分开加入B部分的成分,并在中等搅拌下加入E部分。
在中等搅拌下将所有成分分散或溶解在水相内直至出现均匀凝胶。然后检查pH值。
制造指南:
通过合并所有成分,制备A部分,然后在中速下搅拌。制备B部分并加热至40℃。在此温度下,在渐进搅拌速度下将A部分倒入B部分中直至出现均匀霜。
Claims (11)
1.制备组合物的方法,该组合物包含(a)微粉化的不溶性有机紫外线吸收剂,其中所述微粉化的不溶性紫外线吸收剂选自式(3)的化合物:
及式(7)的化合物:
该方法包括在研磨装置中在研磨助剂存在下研磨粗粒形式的所述不溶性有机紫外线吸收剂,所述研磨助剂选自由下述物质组成的组:
(b1)月桂酰乳酰乳酸钠,
(b2)异硬脂酸异十六烷基酯和/或油酸乙二醇酯,
(b3)油基聚氧乙烯(3)醚磷酸酯DEA盐,
(b4)月桂酸聚乙二醇(20)酯,
(b7)壬基酚聚氧乙烯(10)醚,
(b8)PEG-10聚甘油-2-月桂酸酯,
(b9)PEG-120甲基葡萄糖二油酸酯和/或聚甘油-3甲基葡萄糖二硬脂酸酯,
(b10)失水山梨糖醇聚氧乙烯(20)醚异硬脂酸酯、失水山梨糖醇聚氧乙烯(20)醚油酸酯和PEG/PPG-125/30共聚物,和
(b11)二椰油酰乙二胺PEG-15硫酸钠和/或聚二甲基硅氧烷PEG/PPG-7/4磷酸酯。
3.根据权利要求1的方法,其中由此获得的微粉化的不溶性有机紫外线吸收剂具有0.01至2.0微米的平均粒度。
4.根据权利要求1的方法,其中所述微粉化的不溶性有机紫外线吸收剂通过在研磨装置中研磨粗粒形式的该紫外线吸收剂直至该不溶性有机紫外线吸收剂已转化成微粉化的形式而制成。
5.根据权利要求4的方法,其中所述研磨装置是喷射磨机、球磨机、振动磨机或锤磨机。
6.防晒组合物,其包含:
(a)0.1至25重量%的根据权利要求1制备的微粉化的不溶性有机紫外线吸收剂的组合物;和任选地
(b)化妆上可接受的载体。
7.根据权利要求6的组合物,其中所述微粉化的不溶性有机紫外线吸收剂与通常用于化妆品组合物中以保护人皮肤对抗紫外线辐射的一种或多种附加紫外线吸收剂一起使用。
8.根据权利要求6或7的组合物,其中
额外使用(c)流变改性剂。
9.根据权利要求8的组合物,其中
组分(c)选自黄原胶、无定形二氧化硅和改性淀粉。
10.根据权利要求8的组合物,其中所述流变改性剂(c)以所述组合物的0.1至10重量%的浓度使用。
11.根据权利要求9的组合物,其中所述流变改性剂(c)以所述组合物的0.1至10重量%的浓度使用。
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PCT/EP2008/065916 WO2009068469A2 (en) | 2007-11-29 | 2008-11-20 | Grinding aids for micronized organic uv absorbers |
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WO2012101204A1 (en) * | 2011-01-28 | 2012-08-02 | Momentive Performance Materials Gmbh | Uv-photo-protecting cosmetic composition |
EA028222B9 (ru) * | 2011-10-28 | 2017-12-29 | Юнилевер Н.В. | Водная фотозащитная композиция для личной гигиены |
DE102014202956A1 (de) | 2014-02-18 | 2015-08-20 | Beiersdorf Ag | Kosmetische Emulgatorkombination |
US9731151B2 (en) * | 2014-04-08 | 2017-08-15 | Honeywell International Inc. | Sprayable sunscreen compositions and methods |
BR112016023485B1 (pt) * | 2014-04-11 | 2020-12-22 | Basf Se | composição cosmética |
FR3021536B1 (fr) * | 2014-05-28 | 2016-07-01 | Oreal | Composition photoprotectrice fluide sous forme d'emulsion huile-dans-eau |
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BRPI0709778B1 (pt) * | 2006-05-08 | 2017-12-19 | Ciba Holding Inc. | Triazin derivatives, processes for their preparation, cosmetic composition, and uv absorbing dispersion |
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GB2286774A (en) * | 1994-02-23 | 1995-08-30 | Ciba Geigy Ag | Sunscreen compositions |
US5980872A (en) * | 1995-07-22 | 1999-11-09 | Ciba Specialty Chemicals Corporation | Sunscreen compositions |
EP0893119A1 (en) * | 1997-07-26 | 1999-01-27 | Ciba SC Holding AG | UV-protection formulation |
WO2003063814A1 (en) * | 2002-01-31 | 2003-08-07 | Ciba Specialty Chemicals Holding Inc. | Micropigment mixtures |
WO2004052837A2 (en) * | 2002-12-12 | 2004-06-24 | Ciba Specialty Chemicals Holding Inc. | Amino substituted hydroxyphenyl benzophenone derivatives |
Also Published As
Publication number | Publication date |
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KR20150132598A (ko) | 2015-11-25 |
WO2009068469A2 (en) | 2009-06-04 |
JP2011504899A (ja) | 2011-02-17 |
BRPI0820644A2 (pt) | 2018-07-10 |
WO2009068469A3 (en) | 2009-07-16 |
BRPI0820644B1 (pt) | 2022-06-14 |
EP2224898B1 (en) | 2018-08-15 |
US20100303746A1 (en) | 2010-12-02 |
CN101932302A (zh) | 2010-12-29 |
EP2224898A2 (en) | 2010-09-08 |
KR20100096212A (ko) | 2010-09-01 |
JP5984332B2 (ja) | 2016-09-06 |
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