CN102858916B - 通过使用含植物提取物的苯并环庚三烯酚酮和/或相关苯并环庚三烯酚酮衍生物稳定家用、护体和食品产品 - Google Patents
通过使用含植物提取物的苯并环庚三烯酚酮和/或相关苯并环庚三烯酚酮衍生物稳定家用、护体和食品产品 Download PDFInfo
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- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
- 239000011686 zinc sulphate Substances 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
- 239000002888 zwitterionic surfactant Substances 0.000 description 1
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Abstract
公开了式(1)的苯并环庚三烯酚酮衍生物在保护护体和家用产品以防光解和氧化降解中的用途,其中R1、R2和R7相互独立地为氢、C1-C3烷基或COR8;R3为氢或COOR9;R4为氢或C1-C3烷基;R5为氢、羟基、C1-C3烷氧基或-O-(CO)-R10;R6为氢、C1-C3烷基或COR8;或R5和R6可以一起形成5或6员环;或R6和R7一起形成5或6员环;以及R8、R9、R10相互独立地为C1-C30烷基。
Description
本发明涉及选定的光稳定剂在保护护体和家用产品以防光解和氧化降解中的用途。
近年来对于在化妆品配制剂和家用产品中基于油和脂肪的天然物质的使用增加这一产品趋势也提高了脂肪和油氧化降解的问题,这导致酸败。天然油或不饱和脂肪酸很少不以乳液存在。氧化性变化有时可能产生反应性代谢物,例如酮类、醛类、酸类、环氧化物和脂过氧化物。
结果一方面存在产品气味的不希望变化且另一方面物质易于变坏,这可能改变皮肤耐受性,自由基在皮肤上的不受控形成主要促使许多病理生理调节,例如过敏、发炎、致癌等的开始和发展。
然而,氧化降解过程不仅仅在基于油和脂肪的天然物质中发现。它们也在许多其他化妆品成分,如香料和芳香物质、维生素、着色剂等中发现。
因此,为了防止氧化降解过程(光致氧化、自氧化),将所谓的抗氧化剂(AO)用于化妆品和食品产品中。这些抗氧化剂可以分类成防止氧化的化合物(配合物形成剂、还原剂等)和中断自由基链反应的化合物,例如丁基化羟基甲苯(BHT),丁基化羟基茴香醚(BHA),棓酸酯,如棓酸丙酯(PG),或叔丁基氢醌(TBHQ)。然而,后一化合物通常不能满足有关pH稳定性以及光和温度稳定性的要求。
因此,在该类容器中的活性物由于自氧化过程而不利地改变其性能。这例如导致粘度降低以及颜色或气味变化。
此外,近年来增长的产品趋势也导致透明(玻璃、PET等)容器在化妆品配制剂和家用产品中的使用增加。尽管玻璃和常规塑料在UV-B范围内都具有一定的固有吸收,但在UV-A范围内的吸收非常低。
通常使用通过UV吸收用于透明包装产品的各种稳定技术且其是众所周知的。例如苯并三唑类宽带UV光稳定剂由于与主要吸收UV-B的其他吸收剂如二苯甲酮类相比具有非常好的UV-A和UV-B吸收性能而提高产品稳定性和储存期。当前对于防止或延缓透明包装产品的光诱发褪色已知的最有效稳定剂例如为以商品名BASFTINOGARDHS或BASFTINOGARDTL注册的苯并三唑衍生物。
现在有利的是将抗氧化和自由基清除以及光保护性能组合在一个稳定剂分子中。
惊人地发现基于苯并环庚三烯酚酮(benzotropolone)衍生物的特定光稳定剂具有显著的UV吸收剂和抗氧化剂性能并且因此适合产品保护。
基于苯并环庚三烯酚酮结构部分的多酚可以由植物或真菌分离出来。天然存在的苯并环庚三烯酚酮的实例是红棓酚、红棓酚羧酸、来自真菌木蹄层孔菌(Fomesfomentarius)的fomentariol、来自真菌Tricholomaaurantium的goupiolone和aurantricholone。存在于红茶中的茶黄素是另一类众所周知的含有苯并环庚三烯酚酮核的多酚。
合成苯并环庚三烯酚酮通过1,2-二羟基苯衍生物与1,2,3-三羟基苯衍生物的氧化偶联生产。
合成和天然存在的苯并环庚三烯酚酮化合物的共同点在于它们是有效且光稳定的UV吸收剂,具有强抗氧化性能且因此适合用作稳定剂。
因此,本发明涉及下式的苯并环庚三烯酚酮衍生物在保护护体和家用产品以防光解和氧化降解中的用途:
其中
R1、R2和R7相互独立地为氢、C1-C30烷基或COR8;
R3为氢或COOR9;
R4为氢或C1-C30烷基;
R5为氢、羟基、C1-C30烷氧基或-O-(CO)-R10;
R6为氢、C1-C30烷基或COR8;或
R5和R6可以一起形成5或6员环;或
R6和R7一起形成5或6员环;以及
R8,R9,R10相互独立地为C1-C30烷基。
优选如下式(1)化合物,其中
R1为氢、COR8或C1-C30烷基;
R2、R4和R5为氢;
R3为COOR9;
R6和R7相互独立地为氢、C1-C30烷基或COR8;或
R6和R7一起形成5或6员环;和
R8如在式(1)中所定义。
更优选如下式(1)化合物,其中
R1为氢或CO-CH3;
R2、R4和R5为氢;
R3为COO-C3H7;
R6和R7相互独立地为氢或CO-CH3;或
R6和R7一起形成5或6员环。
还优选如下式(1)化合物,其中
R1、R2和R7相互独立地为氢、甲基或-CO-CH3;
R3为氢或-COOR9;
R4为氢或C1-C30烷基;
R5为氢、甲氧基或-O-(CO)-CH3;
R6为氢、甲基或-CO-CH3;或
R5和R6可以一起形成5或6员环;或
R6和R7一起形成5或6员环;和
R9为C1-C10烷基。
最优选下式化合物:
用于本发明的苯并环庚三烯酚酮的其他实例是下列化合物:
C1-C30烷基是直链或支化基团,如甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基、戊基、异戊基或叔戊基、己基、2-乙基己基、庚基、辛基、异辛基、壬基、癸基、十一烷基、十二烷基、十四烷基、十一烷基、二十烷基、二十四烷基、二十五烷基、二十七烷基、二十八烷基或三十烷基。
C1-C30烷氧基是直链或支化基团,如甲氧基、乙氧基、正丙氧基或异丙氧基(isopropoxy)、异丙氧基(isopropyloxy)、正丁氧基、仲丁氧基、叔丁氧基、戊氧基、异戊氧基或叔戊氧基、己氧基、2-乙基己氧基、庚氧基、辛氧基、异辛氧基、壬氧基、癸氧基、十一烷氧基、十二烷氧基、十四烷氧基、十一烷氧基、二十烷氧基、二十四烷氧基、二十五烷氧基、二十七烷氧基、二十八烷氧基或三十烷氧基。
各烷基可以是饱和或不饱和的。
各烷基可以被一个或多个E取代和/或被一个或多个D间隔。
D为-CO-、-COO-、-O-、-S-、-CR12=CR13-或-C≡C-,以及
E为-OR18、-NR14R15、-COR17、-COOR16或-CONR14R15,其中
R12、R13、R14和R15相互独立地为氢,任选被OH、C1-C18烷基或C1-C18烷氧基取代的C6-C18芳基,任选被-O-间隔的C1-C18烷基,或者
R14和R15一起形成5或6员环,
R16为氢,任选被OH、C1-C18烷基或C1-C18烷氧基取代的C6-C18芳基,任选被-O-间隔的C1-C18烷基;
R17为H,任选被OH、C1-C18烷基或C1-C18烷氧基取代的C6-C18芳基或任选被-O-间隔的C1-C18烷基;
R18为氢,任选被OH、C1-C18烷基或C1-C18烷氧基取代的C6-C18芳基或任选被-O-间隔的C1-C18烷基。
式(1)化合物可以以其质子化或脱质子化形式存在。
本发明所用苯并环庚三烯酚酮衍生物指已知和新型化合物。
新型化合物对应于下式:
其中
R’1、R’2和R’7相互独立地为氢、C1-C30烷基或COR8;
R’3为氢或COOR9;
R’4为氢或C1-C30烷基;
R’5为氢、羟基、C1-C30烷氧基或-O-(CO)-R10;
R’6为氢、C1-C30烷基或COR8;或
R’5和R’6可以一起形成5或6员环;或
R’6和R’7一起形成5或6员环;和
R’8、R’9、R’10相互独立地为C1-C30烷基;
条件是在式(1’)化合物中,R7和R8一起形成5或6员环;或者R6和R7一起形成5或6员环。
优选如下的式(1’)化合物,其中
R3为式的基团,其中
R’20为C3-C30烷基;
R’5为氢或C1-C12烷基;
R’1、R’6和R’7为氢、COR’9或C1-C30烷基;和
R’9如在式(1’)中所定义。
还优选对应于下式的化合物:
其中
R’21和R’22相互独立地为氢、OH、C1-C30烷基或C1-C30烷氧基;以及
R’1、R’2、R’3、R’4和R’7如在式(1’)中所定义。
还优选下式化合物:
其中
R’21和R’22相互独立地为氢、OH、C1-C30烷基或C1-C30烷氧基;
R’1、R’2、R’3、R’4和R’5如在式(1’)中所定义。
更优选如下的式(3’)化合物,其中
R’21和R’22相互独立地为氢、OH、未取代的C1-C30烷基或未取代的C1-C30烷氧基;以及
R’1、R’2、R’3、R’4和R’5如在式(1’)中所定义。
其他新型化合物对应于式(3’),其中
R3为式的基团,其中
R’20为C3-C30烷基;
R’5为氢或C1-C12烷基;
R’1、R’6和R’7为氢、COR’9或C1-C30烷基;和
R’9如在式(1’)中所定义。
其他新型化合物对应于下式:
其中
R’2和R’4相互独立地为C1-C30烷基;
R’1、R’5、R’6和R’7为C1-C30烷基或COR8;和
R’8如在式(1’)中所定义。
还优选下式化合物:
其中
R’3为式的基团;
R’20为C3-C30烷基;
R’1、R’6和R’7为氢、COR9或C1-C30烷基;和
R’9为C1-C30烷基。
本发明的苯并环庚三烯酚酮衍生物由天然源如植物提取物分离和/或为通过特定前体化合物如焦棓酚衍生物和1,2-二羟基苯衍生物的化学氧化合成的那些。
式(1)的苯并环庚三烯酚酮衍生物以及这些化合物与表1-3中所列其他UV吸收剂、酚类或非酚类抗氧化剂或配合物形成剂的混合物特别适合保护护体和家用产品以防光解降解。
可以与式(1)化合物混合使用的有机UV滤光剂的实例列于下表中:
式(1)的苯并环庚三烯酚酮衍生物还可以与例如在WO00/25731中所公开的酚类或内酯型抗氧化剂混合使用。
式(1)的苯并环庚三烯酚酮衍生物还可以与在WO03/103622中所公开的受阻胺光稳定剂,例如受阻硝酰基、羟胺和羟胺盐化合物混合使用。
为了优化抗氧化效果,家用和/或个人护理应用可以含有至少一种其他亲水或亲油抗氧化剂,浓度为该制剂总重量的0.0001-10%。这些额外抗氧化剂优选选自:
-生育酚(α、β、γ、δ异构体,尤其是维生素E)及其衍生物(尤其是维生素E衍生物如维生素E乙酸酯、维生素E亚油酸酯、维生素E烟酸酯和维生素E琥珀酸酯)
-含有一个不饱和脂肪链的生育三烯酚(α、β、γ、δ异构体),以及其酸的酯
-抗坏血酸及其与酸如磷酸的酯以及钠、钾、锂和镁盐,抗坏血酰四异棕榈酸酯,与吡咯烷酮羧酸的其他酯和具有通式(3)H(CH2)n(CHR)COOH和(4)CH3(CH2)mCH=CH(CH2)nCOOH的酸的酯,其中R为氢原子或OH基团,m、n为0-20的整数,其中m+n之和最大为21。
-维甲类(Retinoid)包括维生素A的所有天然和/或合成类似物或在皮肤中具有维生素A的生物活性的类视黄醛化合物以及这些化合物的几何异构体和立体异构体。优选化合物是视黄醇、视黄醇酯(例如视黄醛的C2-C22烷基酯(饱和或不饱和烷基链),包括棕榈酸视黄醇酯、乙酸视黄醇酯、丙酸视黄醇酯)、视黄醛和/或视黄酸(包括所有反式视黄酸和/或13-顺式视黄酸)或衍生物。在本文中有用的其他维甲类描述于1987年6月30日授权给Parish等的美国专利4,677,120;1989年12月5日授权给Parish等的美国专利4,885,311;1991年9月17日授权给Purcell等的美国专利5,049,584,1992年6月23日授权给Purcell等的美国专利5,124,356中。其他合适的维甲类是生育酚视黄酸酯[视黄酸的生育酚酯(反式或顺式)],阿达帕林[6-(3-(1-金刚烷基)-4-甲氧基苯基)-2-萘甲酸]和他扎罗汀(6-[2-(4,4-二甲基二氢苯并噻喃-6-基)乙炔基]烟酸乙酯)
-类胡萝卜素如α-、β-、γ-和δ-胡萝卜素,叶黄素,胡萝卜醇,玉米黄质,紫黄质,隐黄质,岩藻黄质,花药黄质,番茄红素,二脱氢番茄红素和四脱氢番茄红素类胡萝卜素
-硫辛酸及其衍生物如α-硫辛酸
-芸香亭酸及其衍生物如α-葡糖基芸香苷,水溶性类黄酮,水合芸香苷(维生素P)
-植物提取物如白茶和绿茶提取物,红茶提取物,菊苣(菊苣(Cichoriumintubybus))叶提取物,西番莲(粉色西番莲(Passifloraincarnata))提取物,Aspalathuslinearis提取物,迷迭香提取物,槭树科枫树(AceraceaeMaple)或蔷薇科樱树(RosaceaeCherry)的红叶提取物,姜黄(CurcumalongaL)(类姜黄素活性成分),火绒草(Leontopodiumalpinum)提取物,余甘子(Emblicaofficinalis)(余甘子(phyllanthusemblica))树提取物...
-酚酸如咖啡酸、3,4-二羟基苯基乙酸、3,4-二羟基苯甲酸。
-棓酸酯如棓酸、棓酸甲酯、棓酸乙酯、棓酸丙酯、棓酸辛酯、棓酸十二烷基酯、棓酸戊酯、棓酸异戊酯,酰化棓酸酯如3,4,5-三(乙酰氧基)苯甲酸甲酯、3,4,5-三(乙酰氧基)苯甲酸丙酯、3,4,5-三(乙酰氧基)苯甲酸辛酯。
-儿茶酚类如1,2-二羟基苯、3-甲基儿茶酚、4-叔丁基儿茶酚或如酰化儿茶酚类如儿茶酚二乙酸酯、3-甲基儿茶酚二乙酸酯、儿茶酚乙酸酯。
-焦棓酚类如1,2,3-三羟基苯、4-乙基焦棓酚、4-丙基焦棓酚、4-丁基焦棓酚、4-戊基焦棓酚、4-异戊基焦棓酚、4-辛基焦棓酚、4-十二烷基焦棓酚或如酰化焦棓酚类如焦棓酚乙酸酯、焦棓酚二乙酸酯、焦棓酚三乙酸酯。
-类黄酮和多酚如选自未取代黄烷酮类、单取代黄烷酮类及其混合物的黄烷酮类;选自未取代查耳酮类、单取代查耳酮类、二取代查耳酮类、三取代查耳酮类及其混合物的查耳酮类;选自未取代黄酮类、单取代黄酮类、二取代黄酮类及其混合物的黄酮类;一种或多种异黄酮类;香豆素类,选自未取代的香豆素类、单取代的香豆素类、二取代的香豆素类及其混合物;黄酮醇,花色素苷,儿茶素如绿茶儿茶素如(-)-表棓儿茶素-3-棓酸酯、(-)-表儿茶素、(-)-表棓儿茶素及其混合物,茶黄素,原花青色素(葡萄籽提取物)。还可以使用宽泛公开于美国专利5,686,082和5,686,367中的类黄酮。
-绿原酸和阿魏酸及其衍生物。
-环庚三烯酚酮衍生物如环庚三烯酚酮(CAS号533-75-5)本身,4-异丙基环庚二烯酚酮,香柏素,密挤青霉酸(stipitaticacid),软毛青霉酸,密挤青霉酸(stipitatonicacid),软毛青霉二酸酐,γ-苧侧素,β-苧侧素,秋水仙裂碱或专利申请WO2008/003529A1中所述环庚三烯酚酮衍生物及其混合物。
还可使用中断在UV射线穿透皮肤或毛发时引起的光化学反应链的第三种抗氧化剂。该类抗氧化剂的典型实例是氨基酸及其衍生物(例如甘氨酸、组氨酸、乙酰组氨酸、酪氨酸、己酰基酪氨酸、色氨酸),咪唑类(例如尿刊酸)及其衍生物,肽类,如D,L-肌肽、D-肌肽、L-肌肽及其衍生物(例如鹅肌肽),金硫葡糖,丙硫尿嘧啶和其他硫醇(例如硫氧环蛋白,谷胱甘肽,半胱氨酸,胱氨酸,半胱胺及其糖基、N-乙酰基、甲基、乙基、丙基、戊基、丁基、月桂基、棕榈酰、油基、亚油基、胆甾烯基和甘油酯)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、核苷和盐)以及还有亚砜亚胺化合物(如丁硫氨酸亚砜亚胺,高半胱氨酸亚砜亚胺,丁硫氨酸砜,戊-、己-、庚-硫氨酸亚砜亚胺)。
还有(金属)螯合剂(尤其是α-羟基脂肪酸、棕榈酸、肌醇六磷酸、乳铁蛋白)以及优选公开于1996年1月30日授权给Bisset等的美国专利5,487,884;1995年10月31日公布的Bush等的国际公布91/16035和91/16034中的那些。羟基酸(例如柠檬酸、乳酸、苹果酸、羟基琥珀酸),腐殖酸,胆汁酸,胆汁提取物,胆红素,胆绿素,EDTA,EDDS,EGTA及其衍生物,不饱和脂肪酸及其衍生物(例如亚麻酸,亚油酸,油酸),叶酸及其衍生物,安息香树脂的苯甲酸松柏基酯,阿魏酸,亚糠基山梨醇,肌肽,丁基羟基甲苯,丁基羟基茴香醚,去甲二氢愈床木酸,三羟基丙基苯基酮,尿酸及其衍生物,甘露糖及其衍生物,N-[3-(3,5-二叔丁基-4-羟基苯基)丙酰基]磺胺酸(及其盐,例如二钠盐),锌及其衍生物(例如ZnO,ZnSO4),硒及其衍生物(例如硒代蛋氨酸),芪及其衍生物(尤其是羟基芪,白藜芦醇和赤松素)和根据本发明合适的那些所述活性成分的衍生物(盐、酯、醚、糖、核苷酸,核苷,肽和类脂)。还可以提到HALS(=“受阻胺光稳定剂”)化合物。
其他合成和天然抗氧化剂例如列于专利WO0025731中:结构1-3(第2页)、结构4(第6页)、结构5-6(第7页)和化合物7-33(第8-14页)。
合适抗氧化剂的实例包括但不限于对羟基苯甲酸及其衍生物(对羟基苯甲酸的乙基异丁基酯、甘油酯),水杨酸酯(辛基戊基、苯基、苄基、基、甘油和二丙二醇酯),亚苄基丙二酸酯,苯基甲基丙酸衍生物如[(4-羟基-3,5-二甲氧基苯基)甲基]丙二酸二(2-乙基己基)酯(CAS号872182-46-2),羟基或甲氧基取代的二苯甲酮类,尿酸或鞣酸及其衍生物。
可以用于本发明化妆品组合物中的其他额外抗氧化剂选自乙酰基半胱氨酸,3-叔丁基-4-羟基茴香醚,2,6-二叔丁基对甲酚,咖啡酸,绿原酸,癸基巯基甲基咪唑,二乙酰基硫代二丙酸酯,双棓酰三油酸酯,硫代二丙酸二月桂基酯,硫代二丙酸二肉豆蔻基酯,二油基生育酚基甲基硅烷醇,芸香苷基二硫酸二钠,硫代二丙酸二硬脂基酯,硫代二丙酸二-十三烷基酯,棓酸十二烷基酯,异抗坏血酸,阿魏酸乙酯,氢醌和烷基化氢醌(例如叔丁基氢醌,二戊基氢醌,二叔丁基氢醌),对羟基茴香醚,羟胺盐酸盐,羟胺硫酸盐,巯基乙酸异辛酯,曲酸,积雪草苷,甲氧基-PEG-7-芸香苷基琥珀酸酯,棓酸辛酯,苯基巯基乙酸,均苯三酚,棓酸丙酯,迷迭香酸及其衍生物,芸香苷,异抗坏血酸钠,巯基乙酸钠,山梨醇缩糠醛,硫二甘醇,硫二甘醇酰胺,亚硫基二乙酸,巯基乙酸,硫羟乳酸,硫代水杨酸,生育酚聚醚-5,生育酚聚醚-10,生育酚聚醚-12,生育酚聚醚-18,生育酚聚醚-50,水溶性维生素E,邻甲苯基双胍,亚磷酸三(壬基苯基)酯,D-泛醇,α-羟基羧酸(尤其是乙醇酸、乳酸、扁桃酸)及其盐,二羟甲基二甲基乙内酰脲,N-酰基氨基酸及其盐(尤其是N-辛酰基甘氨酸)和日柏酚及其混合物,它们用于长期稳定如下通式的甘油单烷基醚:
R-O-CH2-CHOH-CH2-OH,
其中R为支化或未支化的C3-C18烷基,其中烷基可以被一个或多个羟基和/或C1-C4烷氧基取代和/或烷基链可以被至多4个氧原子间隔。
可以用于本发明化妆品组合物中的其他额外抗氧化剂选自丙氨酸二乙酸,五羟黄酮,桑色素,3,4-二羟基苯甲酸,百里酚,香芹酚,儿茶素,以及安息香胶树脂的衍生物,芸香苷及其衍生物,苄基膦酸酯如2,5-二叔丁基-4-羟基苄基膦酸二甲酯、3,5-二叔丁基-4-羟基苄基膦酸二乙酯和3,5-二叔丁基-4-羟基苄基膦酸单乙酯的钙盐。
优选本发明的苯并环庚三烯酚酮衍生物以含有至少一种选自棓酸酯衍生物、儿茶酚衍生物或焦棓酚衍生物的其他抗氧化剂的混合物使用。
除了式(1)的苯并环庚三烯酚酮衍生物外,本发明的家用和/或个人护理组合物还可以含有例如公开于WO00/25731中的酚类或内酯型抗氧化剂和/或公开于WO03/103622中的受阻胺光稳定剂,例如受阻硝酰基、羟胺和羟胺盐化合物。
个人护理用途
式(1)的苯并环庚三烯酚酮衍生物可以作为单一组分或者与尤其用于护肤产品、沐浴和淋浴添加剂、含有香料和芳香物质的制剂、护发产品、洁齿剂、祛臭和止汗制剂、美饰制剂、光保护配制剂、含有活性成分的制剂的其他稳定剂混合使用。
护肤产品尤其为护体油,爽身水,护体凝胶,处理霜(treatmentcream),皮肤保护软膏,剃须制剂,如剃须泡或胶,爽身粉,如婴儿爽身粉,保湿凝胶,保湿喷雾剂,活肤体用喷雾剂,瘦身凝胶(cellulitegel)和换肤霜。
合适的沐浴和淋浴添加剂是淋浴凝胶、浴盐、泡沫浴剂和肥皂。
含有香料和芳香物质的制剂尤其是香味剂(scent)、香水,花露水和剃须液(剃须后制剂)。
合适的护发产品例如为用于人类和动物,尤其是狗的洗发剂,头发调理剂,发用定型和处理产品,烫发剂,发胶和发蜡,发用凝胶,固发剂和染发或漂发剂。
合适的洁齿剂尤其是牙霜(toothcream)、牙膏、漱口剂、口腔冲洗剂、防牙菌斑制剂和假牙清洁剂。
合适的美饰制剂尤其是唇膏、指甲油、眼影、睫毛油、干湿美容品、胭脂、底粉、脱毛剂和太阳油。
含有活性成分的合适化妆品配制剂尤其是激素制剂、维生素制剂、植物提取物制剂和抗菌制剂。
所述护体产品可以呈霜、软膏、糊、泡沫、凝胶、洗液、底粉、美容品、喷雾剂、棒或气雾剂形式。
它们优选含有式(1)的苯并环庚三烯酚酮衍生物和任选其他UV吸收剂、位阻胺、络合剂和酚类或非酚类抗氧化剂。
因此,本发明还涉及一种包含至少一种式(1)的苯并环庚三烯酚酮衍生物的护体产品。
式(1)的苯并环庚三烯酚酮衍生物基于整个配制剂以约5-10000ppm,优选约10-5000ppm,最优选约100-1000ppm的浓度存在于护体和家用产品中。
本发明的化妆品组合物还可含有一种或多种如下所述的额外化合物。
脂肪醇
基于具有6-18个,优选8-10个碳原子的脂肪醇[包括鲸蜡醇、硬脂醇、鲸蜡硬脂醇、油醇、辛基十二烷醇、C12-C15醇的苯甲酸酯、乙酰化羊毛脂醇等]的Guerbet醇。
脂肪酸的酯
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、二聚体二醇或三聚体三醇)和/或Guerbet醇的酯,例如己酸、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、顺-9-二十碳烯酸、山萮酸和芥酸及其工业级混合物(例如在天然脂肪和油的加压除去中、在来自Roelen羰基合成的醛的还原中或在不饱和脂肪酸酸的二聚中得到)与醇类,例如异丙醇、己醇、辛醇、2-乙基己基醇、癸醇、月桂醇、异十三烷醇、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、顺-9-二十碳烯醇、山萮醇、芥醇和巴西基醇及其工业级混合物(例如在基于脂肪或油的工业级甲基酯或来自Roelen羰基合成的醛的高压氢化以及在不饱和脂肪醇的二聚中作为单体馏分得到)的酯。
该类酯油的实例是肉豆蔻酸异丙酯、棕榈酸异丙酯、硬脂酸异丙酯、异硬脂酸异丙酯、油酸异丙酯、硬脂酸正丁酯、月桂酸正己酯、油酸正癸酯、硬脂酸异辛酯、硬脂酸异壬酯、异壬酸异壬酯、棕榈酸2-乙基己基酯、月桂酸2-己基酯、硬脂酸2-己基癸基酯、棕榈酸2-辛基十二烷基酯、油酸油基酯、芥酸油基酯、油酸瓢心菜基酯、芥酸瓢心菜基酯、辛酸鲸蜡硬脂基酯、棕榈酸鲸蜡基酯、硬脂酸鲸蜡基酯、油酸鲸蜡基酯、山萮酸鲸蜡基酯、乙酸鲸蜡基酯、肉豆蔻酸肉豆蔻基酯、山萮酸肉豆蔻基酯、油酸肉豆蔻基酯、硬脂酸肉豆蔻基酯、棕榈酸肉豆蔻基酯、乳酸肉豆蔻基酯、丙二醇二辛酸/癸酸酯、庚酸硬脂基酯、苹果酸二异硬脂基酯、羟基硬脂酸辛酯等。
天然或合成甘油三酯,包括甘油酯和衍生物
通过与其他醇反应而改性的基于C6-C18脂肪酸的甘油二酯或甘油三酯(甘油三辛酸/癸酸酯、小麦胚芽甘油酯等)。聚甘油的脂肪酸酯(聚甘油-n如聚甘油-4癸酸酯,聚甘油-2异硬脂酸酯等或蓖麻油,氢化植物油,甜杏仁油,小麦胚芽油,芝麻油,氢化棉籽油,椰子油,鳄梨油,玉米油,氢化蓖麻油,牛油树脂,可可脂,大豆油,薄荷油,葵花油、红花油,澳洲坚果油,橄榄油,氢化牛脂,杏仁油,榛子油,玻璃苣油等。
蜡
包括长链酸和醇的酯以及具有蜡状性能的化合物,例如巴西棕榈蜡,蜂蜡(白色或黄色),羊毛脂蜡,小烛树蜡,地蜡,日本蜡,石蜡,微晶蜡,纯地蜡,鲸蜡硬脂基酯蜡,合成蜂蜡等。还有亲水蜡如鲸蜡硬脂醇或部分甘油酯。
珠光蜡
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;部分甘油酯,尤其是甘油单硬脂酸酯;多价、未取代或羟基取代羧酸与具有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,例如总共具有至少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基醚;脂肪酸,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。
烃油
矿物油(轻质或重质),矿脂(黄色或白色),微晶蜡,烷烃和异烷烃化合物,氢化异烷烃分子如聚癸烯和聚丁烯,氢化聚异丁烯,角鲨烷,异十六烷,异十二烷以及来自植物和动物界的其他物质。
聚硅氧烷或硅氧烷(有机取代的聚硅氧烷)
二甲基聚硅氧烷,甲基苯基聚硅氧烷,环状聚硅氧烷,还有氨基-、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,其在室温下可以呈液体或树脂状形式。线性聚硅氧烷,聚二甲基硅氧烷(DowCorning200流体,RhodiaMirasilDM),聚二甲基硅氧烷醇,环状聚硅氧烷流体,环戊硅氧烷挥发物(DowCorning345流体),苯基聚三甲基硅氧烷(phenyltrimethicone)(DowCorning556流体)。还合适的西甲硅油,其为平均链长为200-300个二甲基硅氧烷单元的聚二甲基硅氧烷与氢化硅酸酯的混合物。此外,由Todd等对合适挥发性聚硅氧烷所作详细评述可以在Cosm.Toil.91,27(1976)中找到。
氟化或全氟化油
全氟己烷、二甲基环己烷、乙基环戊烷、聚全氟甲基异丙基醚。
乳化剂
任何常规可以使用的乳化剂可以用于该组合物。乳化剂体系例如可以包含碳环酸及其盐:钠、钾和铵的碱性皂,钙或镁的金属皂,有机基皂如月桂酸、棕榈酸、硬脂酸和油酸等。烷基磷酸酯或磷酸酯,酸式磷酸酯,二乙醇胺磷酸酯,鲸蜡基磷酸钾。乙氧基化羧酸或聚乙二醇酯,PEG-n酰化物。具有8-22个碳原子的线性脂肪醇,2-30mol氧化乙烯和/或0-5mol氧化丙烯与具有12-22个碳原子的脂肪酸和在烷基中具有8-15个碳原子的烷基酚的支化。脂肪醇聚乙二醇醚,如月桂醇聚醚-n,鲸蜡硬脂醇聚醚-n,硬脂醇聚醚-n,油醇聚醚-n。脂肪酸聚乙二醇醚如PEG-n硬脂酸酯,PEG-n油酸酯,PEG-n椰油酸酯。甘油单酯和多元醇酯。1-30mol氧化乙烯与多元醇的加成产物的C12-C22脂肪酸单-和二酯。脂肪酸和聚甘油酯如甘油单硬脂酸酯,二异硬脂酰基聚甘油-3-二异硬脂酸酯,聚甘油-3-二异硬脂酸酯,三甘油二异硬脂酸酯,聚甘油-2-倍半异硬脂酸酯或聚甘油二聚酸酯。选自多种这些物质类别的化合物的混合物也是合适的。脂肪酸聚乙二醇酯如二甘醇单硬脂酸酯、脂肪酸和聚乙二醇酯,脂肪酸和蔗糖酯如蔗糖酯,甘油和蔗糖酯如甘油蔗糖酯。山梨醇和脱水山梨醇,具有6-22个碳原子的饱和和不饱和脂肪酸和氧化乙烯加成产物的脱水山梨醇单-和二酯。聚山梨酸酯-n系列,脱水山梨醇酯如倍半异硬脂酸酯,脱水山梨醇,PEG-(6)-异硬脂酸酯脱水山梨醇,PEG-(10)-脱水山梨醇月桂酸酯,PEG-17-二油酸酯脱水山梨醇,葡萄糖衍生物,C8-C22烷基-单和低聚糖苷以及其中优选葡萄糖作为糖组分的乙氧基化类似物。O/W乳化剂如甲基葡糖聚醚-20倍半硬脂酸酯,脱水山梨醇硬脂酸酯/蔗糖椰油酸酯,甲基葡糖倍半硬脂酸酯,鲸蜡硬脂醇/鲸蜡硬脂基葡糖苷。W/O乳化剂如甲基葡糖二油酸酯/甲基葡糖异硬脂酸酯。硫酸酯和磺化衍生物,磺基琥珀酸二烷基酯,琥珀酸二辛酯,月桂基磺酸烷基酯,线性磺化石蜡,磺化四亚丙基磺酸酯,月桂基硫酸钠,月桂基硫酸铵和乙醇胺月桂基硫酸盐,月桂基醚硫酸盐,月桂基聚醚硫酸钠,磺基琥珀酸盐,酰基羟乙磺酸盐,链烷醇酰胺硫酸盐,牛磺酸盐,甲基牛磺酸盐,咪唑硫酸盐。胺衍生物,胺盐,乙氧基化胺,带有含杂环的链的氧化胺如烷基咪唑啉,吡啶衍生物,isoquinoteine,鲸蜡基吡啶氯化物,鲸蜡基吡啶溴化物,季铵如鲸蜡基三甲基溴化铵(CTBA),硬脂基烷基铵(stearylalkonium)。酰胺衍生物,链烷醇酰胺如酰胺DEA,乙氧基化酰胺如PEG-n酰胺,氧化酰胺(oxydeamide)。聚硅氧烷/多烷基(polyalkyl)/聚醚共聚物和衍生物,聚二甲基硅氧烷,共聚多元醇,聚硅氧烷聚氧乙烯共聚物,聚硅氧烷二醇共聚物。丙氧基化或POE-n醚(美罗沙波(Meroxapol)),泊洛沙姆(Polaxamer)或聚(氧乙烯)m-嵌段-聚(氧丙烯)n-嵌段(氧乙烯)。在分子中带有至少一个季铵基团和至少一个羧酸盐和/或磺酸盐基团的两性离子表面活性剂。尤其合适的两性离子表面活性剂是甜菜碱,如N-烷基-N,N-二甲基甘氨酸铵,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,椰油酰氨基丙基二甲基甘氨酸铵和在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-羟乙基咪唑啉以及甘氨酸椰油酰氨基乙基羟乙基羧甲基酯,N-烷基甜菜碱,N-烷基氨基甜菜碱。烷基咪唑啉、羟烷基肽(alkylopeptide)、脂氨基酸,自乳化碱和K.F.DePolo,Ashorttextbookofcosmetology,第8章,表8-7,第250-251页中所述化合物。
非离子性乳化剂如PEG-6蜂蜡(和)PEG-6硬脂酸酯(和)聚甘油-2异硬脂酸酯[Apifac],硬脂酸甘油酯(和)PEG-100硬脂酸酯[Arlacel165],PEG-5硬脂酸甘油酯[Arlatone983S],脱水山梨醇油酸酯(和)聚甘油-3蓖麻醇酸酯[Arlacel1689],脱水山梨醇硬脂酸酯和蔗糖椰油脂肪酸酯[Arlatone2121],硬脂酸甘油酯和月桂醇聚醚-23[Cerasynth945],鲸蜡硬脂醇和鲸蜡基聚醚-20[CetomacrogolWax],鲸蜡硬脂醇和聚山梨酸酯60以及PEG-150和硬脂酸酯-20[PolawaxGP200,PolawaxNF],鲸蜡硬脂醇和鲸蜡硬脂基聚葡糖苷[EmulgadePL1618],鲸蜡硬脂醇和鲸蜡硬脂醇聚醚-20[Emulgade1000NI,Cosmowax],鲸蜡硬脂醇和PEG-40蓖麻油[EmulgadeFSpecial],鲸蜡硬脂醇和PEG-40蓖麻油以及鲸蜡硬脂基硫酸钠[EmulgadeF],硬脂醇和硬脂醇聚醚-7以及硬脂醇聚醚-10[EmulgatorE2155],鲸蜡硬脂醇和硬脂基聚醚-7以及硬脂醇聚醚-10[乳化蜡U.S.N.F],硬脂酸甘油酯和PEG-75硬脂酸酯[Gelot64],丙二醇鲸蜡基聚醚-3乙酸酯[HetesterPCS],丙二醇异鲸蜡基聚醚(isoceth)-3乙酸酯[HetesterPHA],鲸蜡硬脂醇以及鲸蜡基聚醚-12和油醇聚醚-12[LanbritolWaxN21],PEG-6硬脂酸酯和PEG-32硬脂酸酯[Tefose1500],PEG-6硬脂酸酯和鲸蜡基聚醚-20以及硬脂醇聚醚-20[Tefose2000],PEG-6硬脂酸酯和鲸蜡基聚醚-20以及硬脂酸甘油酯和硬脂醇聚醚-20[Tefose2561],硬脂酸甘油酯和鲸蜡硬脂醇聚醚-20[TeginacidH,C,X]。
阴离子乳化剂如PEG-2硬脂酸酯SE,硬脂酸甘油酯SE[Monelgine,CutinaKD],丙二醇硬脂酸酯[TeginP],鲸蜡硬脂醇和鲸蜡硬脂基硫酸钠[LanetteN,CutinaLE,CrodacolGP],鲸蜡硬脂醇和月桂基硫酸钠[LanetteW],三羊毛脂醇聚醚-4磷酸酯以及甘油硬脂酸酯和PEG-2硬脂酸酯[Sedefos75],硬脂酸甘油酯和月桂基硫酸钠[TeginacidSpecial]。阳离子酸基质如鲸蜡硬脂醇和鲸蜡基三甲基溴化铵。
乳化剂基于该组合物的总重量可以以1-30重量%,尤其是4-20重量%,优选5-10重量%的量使用。
当配制成O/W乳液时,该类乳化剂体系的优选量可占油相的5-20%。
加脂剂
适合用作加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酯化羊毛脂和卵磷脂衍生物,多元醇脂肪酸酯,甘油单酯和脂肪酸链烷醇酰胺,后者同时起泡沫稳定剂的作用。
表面活性剂
合适的温和表面活性剂,即尤其被皮肤良好耐受的表面活性剂实例包括脂肪醇聚乙二醇醚硫酸盐、甘油单酯硫酸盐、磺基琥珀酸单-和/或二-烷基酯、脂肪酸羟乙磺酸盐、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产物,后者优选基于小麦蛋白。
稠度调节剂/增稠剂和流变改性剂
二氧化硅,硅酸镁,硅酸铝,多糖或其衍生物如透明质酸,黄原胶,瓜耳胶,琼脂,藻酸盐,角叉菜胶,格兰胶(gellan),果胶,或改性纤维素如羟基纤维素、羟丙基甲基纤维素。此外,聚丙烯酸酯或网状丙烯酸均聚物和聚丙烯酰胺,卡波姆(carbomer)(丙烯酸聚合物(carbopol)类型980,981,1382,ETD2001,ETD2020,Ultrez10)或Salcare类型如SalcareSC80(硬脂醇聚醚-10烯丙基醚/丙烯酸酯共聚物),SalcareSC81(丙烯酸酯共聚物),SalcareSC91和SalcareAST(丙烯酸钠共聚物/PPG-1十三烷基聚醚-6),Sepigel305(聚丙烯酰胺/月桂醇聚醚-7),SimulgelNS和SimulgelEG(丙烯酸羟基乙酯/丙烯酰基二甲基牛磺酸钠共聚物),Stabilen30(丙烯酸酯/异癸酸乙烯酯交联聚合物),PemulenTR-1(丙烯酸酯/丙烯酸C10-30烷基酯共聚物交联聚合物),LuvigelEM(丙烯酸钠共聚物),Aculyn28(丙烯酸酯/山萮基聚醚-25甲基丙烯酸酯共聚物)等。
聚合物
合适的阳离子性聚合物例如为阳离子性纤维素衍生物,例如可由Amerchol以名称PolymerJR400得到的季化羟甲基纤维素,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,例如聚二醇和胺的缩合产物,季化胶原蛋白多肽,例如月桂基二甲铵羟丙基水解胶原蛋白季化小麦多肽,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,己二酸和二甲氨基羟丙基二亚乙基三胺的共聚物(Cartaretin/Sandoz),丙烯酸与二甲基二烯丙基氯化铵的共聚物(Merquat550/Chemviron),例如如FR-A-2252840所述的聚氨基聚酰胺,及其交联的水溶性聚合物,例如季化脱乙酰壳多糖的阳离子壳多糖衍生物,任选作为微晶分布;二卤代烷基化物如二溴丁烷与双-二烷基胺如双-二甲氨基-1,3-丙烷的缩合产物,阳离子瓜耳胶,例如来自Celanese的JaguarC-17、JaguarC-16,季化铵盐聚合物,例如Miranol的MirapolA-15,MirapolAD-1,MirapolAZ-1。作为阴离子性、两性离子、两性和非离子性聚合物可以考虑例如乙酸乙烯酯/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,未交联的聚丙烯酸和用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/乙酸乙烯酯共聚物,乙烯基吡咯烷酮/甲基丙烯酸二甲氨基乙酯/乙烯基己内酰胺三元共聚物以及任选衍生的纤维素醚和聚硅氧烷。此外,可以使用EP1093796(第3-8页第17-68段)中所述聚合物。
阳离子表面活性剂
鲸蜡基三甲基溴化铵(CTAB),聚二甲基硅氧烷共聚多元醇,酰胺基聚甲基硅氧烷,丙烯酰胺基丙基三甲基氯化铵/丙烯酰胺共聚物,瓜耳胶羟丙基三甲基氯化铵,羟基鲸蜡基羟乙基二甲基氯化铵,列于InternationalCosmeticIngredientDictionaryandHandbook,第7版,1997中的季铵盐化合物,例如Quaternium-80,列于InternationalCosmeticIngredientDictionaryandHandbook,第7版,1997中的聚季铵盐化合物,例如聚季铵盐-5,聚季铵盐-6,聚季铵盐-7,聚季铵盐-10,聚季铵盐-11,聚季铵盐-17,聚季铵盐-18,聚季铵盐-24或聚季铵盐-27,聚季铵盐-28,聚季铵盐-32,聚季铵盐-37。
生物源活性成分
生物源活性成分应理解为指例如生育酚,生育酚乙酸酯,生育酚棕榈酸酯,抗坏血酸,脱氧核糖核酸,视黄醇,没药醇,尿囊素,植三醇,泛醇,AHA酸,氨基酸,神经酰胺,拟神经酰胺,精油,植物提取物和维生素复合物。
祛臭活性成分
作为祛臭活性成分的例如为止汗剂,例如水合氯化铝(参见J.Soc.Cosm.Chem.24,281(1973))。在HoechstAG,Frankfurt(FRG)的商标下例如可以市购对应于式Al2(OH)5Cl×2.5H2O的水合氯化铝,尤其优选使用后者(参见J.Pharm.Pharmacol.26,531(1975))。除了水合氯化物外,还可以使用羟基乙酸铝和酸性铝/锆盐。可以将酯酶抑制剂作为其他祛臭活性成分加入。该类抑制剂优选为柠檬酸三烷基酯,如柠檬酸三甲酯、柠檬酸三丙酯、柠檬酸三异丙酯、柠檬酸三丁酯和尤其是柠檬酸三乙酯(HydagenCAT,Henkel),它们抑制酶活性并且因此降低臭味形成。考虑作为酯酶抑制剂的其他物质是甾醇硫酸酯或磷酸酯,例如羊毛甾醇、胆甾醇、菜油甾醇、豆甾醇和谷甾醇硫酸酯或磷酸酯,二羧酸及其酯,例如戊二酸、戊二酸单乙酯、戊二酸二乙酯,己二酸、己二酸单乙酯、己二酸二乙酯、丙二酸和丙二酸二乙酯以及羟基羧酸及其酯,例如柠檬酸、苹果酸、酒石酸或酒石酸二乙酯。影响胚芽群落和杀灭或抑制汗液分解细菌生长的抗菌活性成分同样可以存在于该制剂(尤其是棒制剂)中。实例包括脱乙酰壳多糖、苯氧基乙醇和葡萄糖酸洗必泰。5-氯-2-(2,4-二氯苯氧基)苯酚(Triclosan,Irgasan,BASF)也已证明尤其有效。
去头屑剂
作为去头屑剂例如可以使用苯咪丁酮、羟甲辛吡酮和吡硫锌。常规成膜剂例如包括脱乙酰壳多糖、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、含有高比例丙烯酸的季化纤维素衍生物的聚合物、胶原蛋白、透明质酸及其盐和类似化合物。
水溶助长剂
为了改善流动性能,还可以使用水溶助长剂,例如具有低碳原子数的乙氧基化或非乙氧基化单醇或二醇或多元醇或其醚(例如乙醇、异丙醇、1,2-二丙二醇、丙二醇、甘油、乙二醇、乙二醇单乙基醚、乙二醇单丁基醚、丙二醇单甲基醚、丙二醇单乙基醚、丙二醇单丁基醚、二甘醇单甲基醚、二甘醇单乙基醚、二甘醇单丁基醚和类似产物)。用于该目的的多元醇优选包含2-15个碳原子和至少两个羟基。多元醇还可以含有其他官能基团,尤其是氨基,和/或可以用氮改性。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、己二醇以及还有平均分子量为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,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,例如山梨醇或甘露糖醇;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,如二乙醇胺或2-氨基-1,3-丙二醇。
防腐剂
合适的防腐剂例如包括对羟基苯甲酸甲基、乙基、丙基、丁基酯,苯扎氯铵,2-溴-2-硝基-1,3-丙二醇,脱氢乙酸,二偶氮烷基脲,2-二氯苄醇,二甲基二羟甲基乙内酰脲,甲醛溶液,甲基二溴戊二腈,苯氧基乙醇,羟甲基甘氨酸钠,咪唑烷基脲,三氯生和列于下列参考文献中的其他物质类别:K.F.Depolo-AShortTextbookOfCosmetology,第7章,表7-2,7-3,7-4和7-5,P210-219。
抑菌剂
抑菌剂的典型实例是对革兰氏阳性细菌具有特异作用的防腐剂,如2,4,4′-三氯-2′-羟基二苯基醚,洗必泰(1,6-二(4-氯苯基双胍基)己烷)或TCC(3,4,4′-三氯甲酰苯胺)。大量芳族物质和精油也具有抗菌性能。典型实例是活性成分丁子香油、薄荷油和百里香油中的丁子香酚、薄荷醇和百里酚。令人感兴趣的天然祛臭剂是萜烯醇法尼醇(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。也已经证明甘油单月桂酸酯为抑菌剂。额外抑菌剂的存在量基于制剂的固体含量通常为0.1-2重量%。
芳香油
天然和/或合成芳族物质的混合物。天然芳族物质例如为来自花(百合花、熏衣草、玫瑰、茉莉、橙花、依兰),茎和叶(天竺葵、广藿香、橙叶),果实(大茴香、芫荽、蒿子、杜松),果皮(香柠檬、柠檬、橙子),根(肉豆蔻、当归、芹菜、小豆蔻、广木香、鸢尾、菖蒲),木材(松木、檀香、愈创木、雪松、紫檀),草本植物和禾本科植物(龙蒿、柠檬草、鼠尾草、百里香),针和细枝(云杉、松、欧洲赤松、中欧山松),树脂和香脂(白松香、榄香、安息香、没药、乳香、枯树脂)的提取物。动物原料也可考虑,例如麝猫香料和海狸香。典型的合成芳族物质例如为酯、醚、醛、酮、醇或烃类的产物。酯类芳族物质化合物例如为乙酸苄基酯、异丁酸苯氧基乙酯、乙酸对叔丁基环己基酯、乙酸芳樟醇酯、二甲基乙酸苄基甲酯、乙酸苯基乙酯、苯甲酸芳樟醇酯、甲酸苄酯、甲基苯基甘氨酸乙基酯、环己基丙酸烯丙基酯、丙酸苏合香酯(styrallylpropionate)和水杨酸苄基酯。醚例如包括苄基乙基醚;醛例如包括具有8-18个烃原子的线性链烷醛、柠檬醛、香茅醛、香茅基氧乙醛(citronellyloxyacetaldehyde)、仙客来醛、羟基香茅醛、铃兰醛和对叔丁基苯丙醛;酮例如包括紫罗酮、异甲基紫罗酮和甲基柏木酮;醇例如包括茴香脑、香茅醇、丁子香酚、异丁子香酚、香叶醇、芳樟醇、苯基乙醇和萜品油;以及烃主要包括萜烯和香脂。然而,优选使用一起产生引诱香味的各种芳族物质的混合物。主要用作香味组分的较低挥发性的精油也适合作为芳香油,例如鼠尾草油、春黄菊油、丁子香油、蜂花油、肉桂叶油、莱姆花油、刺柏子油、香根油、乳香油、波斯树油、岩蔷薇油和杂熏衣草油。优选单独或以相互的混合物使用香柠檬油、二氢月桂烯醇、铃兰醛、新铃兰醛、香茅醇、苯基乙醇、己基肉桂醛、香叶醇、苄基丙酮、仙客来醛、芳樟醇、乙氧基甲氧基环十一烷、龙涎呋喃、吲哚、二氢茉莉酮酸甲酯、Sandelice、柠檬油、红桔油、橙油、格蓬酯、3,6-二甲基-3-环己烯甲醛(cyclovertal)、杂熏衣草油、肉豆蔻鼠尾草油、突厥酮、波旁天竺葵精油、水杨酸环己酯、甲基柏木酮、iso-E-Super、FixolideNP、2,4-二羟基-3,6-三甲基苯甲酸甲酯(evernyl)、γ-甲基紫罗兰酮、苯基乙酸、乙酸香叶基酯、乙酸苄酯、玫瑰醚、romillat、irotyl和floramat。
其他助剂
此外,化妆品制剂还可以含有作为助剂的消泡剂,如聚硅氧烷,结构化剂(structurant),如马来酸,加溶剂,如乙二醇、丙二醇、甘油或二甘醇,遮光剂,如胶乳,苯乙烯/PVP或苯乙烯/丙烯酰胺共聚物,喷射剂,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如氧化染料前体,还原剂,如巯基乙酸及其衍生物,硫代乳酸,半胱胺,硫代苹果酸或巯基乙烷磺酸,或氧化剂,如过氧化氢、溴酸钾或溴酸钠。
合适的昆虫驱除剂例如为N,N-二乙基间甲苯甲酰胺,1,2-戊二醇或昆虫驱除剂3535;合适的自晒黑剂例如为二羟基丙酮和/或赤藓酮糖或WO01/85124中所述的二羟基丙酮和/或二羟基丙酮前体和/或赤藓酮糖。
本发明稳定剂体系特别适合稳定护体产品,尤其是:
-护肤制剂,例如片剂形式的皮肤洗涤和清洁制剂或液体皂,无皂洗涤剂或洗涤糊,
-沐浴制剂,例如液体(泡沫浴、乳、淋浴制剂)或固体沐浴制剂,例如浴块和浴盐;
-护肤制剂,例如活肤乳液、多重乳液(multiemulsion)或护肤油;护体油、爽身水,护体凝胶;皮肤保护软膏;
-化妆品个人护理制剂,例如日霜或霜粉形式的面部美容品,化妆粉底(松散或压制),胭脂或美容霜,护眼制剂,例如眼影制剂,睫毛油,眼线笔,眼霜或眼部多效霜(eye-fixcream);护唇制剂,例如唇膏、唇彩、唇线笔,护甲制剂,如指甲油、指甲油卸妆剂、指甲硬化剂或指甲脱膜剂;
-护足制剂,例如足浴剂、脚气药粉、护足霜或足用香脂,特殊祛臭剂和止汗剂或胼胝去除制剂;
-光保护制剂,如防晒乳、防晒液、防晒霜或防晒油,防晒剂或热带制剂(tropical),预晒黑制剂或日晒后制剂;
-皮肤晒黑制剂,例如自晒黑霜;
-去色素制剂,例如用于漂白皮肤的制剂或亮肤制剂;
-驱虫剂,例如驱虫油、驱虫液、驱虫喷雾剂或驱虫棒;
-祛臭剂,例如祛臭喷雾剂、泵喷雾剂、祛臭凝胶、棒或滚珠(roll-ons);
-止汗剂,例如止汗棒、霜或滚珠;
-清洁和护理暗疮皮肤的制剂,例如合成洗涤剂(固体或液体),去皮或擦洗制剂或去皮面膜;
-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,凝胶形式或气雾剂泡沫形式的脱毛制剂;
-剃须制剂,例如剃须皂、发泡剃须膏、非发泡剃须膏、泡沫和凝胶、用于干剃须的剃须前制剂,剃须后制剂或剃须后护肤蜜;
-香料制剂,例如含香料和芳香物质的制剂(香味剂,花露水,化妆水,香水,淡香水,香料),芳香油或香料霜;
-化妆品发用处理制剂,例如洗发剂和调理剂形式的洗发制剂,护发制剂,例如预处理制剂,爽发水,定型霜,定型凝胶,润发油,护发素,处理包,强发处理剂,发用结构化制剂,例如长效卷发用卷发制剂(热烫、温和烫、冷烫),直发制剂,液体发用定型制剂,发用泡沫,发胶,漂白制剂,例如过氧化氢溶液,光亮洗发剂,漂白霜,漂白粉,漂白糊或油,暂时、半长效或长效发用着色剂,含有自氧化染料的制剂,或天然发用着色剂,如指甲花或春黄菊;
-洁齿剂,尤其是牙霜、牙膏、漱口剂,口腔冲洗剂,防牙菌斑制剂和假牙清洁剂;
-美饰制剂,尤其是唇膏,指甲油,眼影,睫毛油,干湿美容品,胭脂,底粉,脱毛剂和太阳油,
-含活性成分的化妆品配制剂,尤其是激素制剂、维生素制剂、植物提取物制剂和抗菌制剂。
合适的含活性成分的化妆品配制剂尤其是激素制剂、维生素制剂、植物提取物制剂和抗菌制剂。
存在形式
所列最终配制剂可以宽范围的存在形式存在,例如:
-液体制剂形式如W/O、O/W、O/W/O、W/O/W或PIT乳液和所有种类的微乳液,
-凝胶形式,
-油、霜、乳或洗液形式,
-棒形式,
-喷雾剂(含喷射气体的喷雾剂或泵喷雾剂)或气雾剂形式,
-泡沫形式,或者
-糊形式。
作为皮肤用化妆品制剂特别重要的是光保护制剂,如防晒乳、防晒液、防晒霜、防晒油、防晒剂或热带制剂,预晒黑制剂或日晒后制剂,还有皮肤晒黑制剂,例如自晒黑霜。特别令人感兴趣的是防晒霜、防晒液、防晒乳和喷雾剂形式的防晒制剂。
作为发用化妆品制剂特别重要的是上述发用处理制剂,尤其是洗发剂形式的洗发制剂,头发调理剂,护发制剂,例如预处理制剂,爽发水,定型霜,定型凝胶,润发油,护发素,处理包,强发处理剂,直发制剂,液体发用定型制剂,发用泡沫和发胶。特别令人感兴趣的是洗发剂形式的洗发制剂。
洗发剂例如具有下列组成:
0.01-5重量%的式(1)化合物,
12.0重量%的月桂醇聚醚-2-硫酸钠,
4.0重量%椰油酰胺基丙基甜菜碱,
3.0重量%的氯化钠,
和加至100%的水。
例如,尤其可以使用下列发用化妆品配制剂:
a1)自发乳化的储备配制剂,包含本发明式(1)化合物,任选的另一稳定剂,PEG-6-C10羰基合成醇和脱水山梨醇倍半油酸酯,向其中加入水和任何所需季铵化合物,例如4%貂油酰胺基丙基二甲基-2-羟基乙基氯化铵或Quaternium80;
a2)自发乳化的储备配制剂,包含本发明式(1)化合物,任选的另一稳定剂,柠檬酸三丁酯和PEG-20-脱水山梨醇单油酸酯,向其中加入水和任何所需季铵化合物,例如4%貂油酰胺基丙基二甲基-2-羟基乙基氯化铵或Quaternium80;
b)季铵掺杂的(quat-doped)溶液,包含在丁基三甘醇和柠檬酸三丁酯中的本发明式(1)化合物以及任选另一稳定剂;
c)包含本发明式(1)化合物与烷基吡咯烷酮以及任选另一稳定剂的混合物或溶液。
本发明护体产品的实例列于下表中:
家用产品
本发明的稳定剂体系也用于家用清洁和处理剂,例如用于洗衣产品和织物柔顺剂,液体清洁和擦洗剂,玻璃清洁剂,中性清洁剂(通用清洁剂),酸性家用清洁剂(沐浴),浴室清洁剂,WC清洁剂,例如用于洗涤、漂洗和餐具洗涤剂,厨房和炉灶清洁剂,透明漂洗剂,洗餐具机洗涤剂,鞋油,抛光蜡,地板清洁剂和地板蜡,金属、玻璃和陶瓷清洁剂,织物护理产品,毯类清洁剂和地毯洗剂,除锈、脱色和去污剂(去污剂盐),家具和多用途抛光剂,皮革和乙烯基塑料修饰剂(皮革和乙烯基塑料喷雾剂)以及空气清新剂。
家用清洁剂是一种或多种下列组分的水溶液或醇溶液(乙醇或异丙醇):
-阴离子、非离子、两性和/或阳离子表面活性剂
-通过动物和植物脂皂化制备的皂类
-无机酸,如盐酸、磷酸或硫酸,
-用于碱性产品的无机(NaOH或KOH)或有机碱;
-用于改善表面清洁的磨料,
-用于表面维护和保护的蜡和/或聚硅氧烷,
-聚磷酸盐,
-释放次氯酸盐或卤素的物质;
-包含漂白活性剂如TAED,例如过硼酸钠或H2O2的过氧化物;
-酶;
-在洗涤剂中的变色抑制剂、去污化合物、灰垢抑制剂、抑泡剂、荧光增白剂;
-基于蜡的清洁剂可以包含选自挥发油、松节油和/或链烷烃的溶剂和基于蜡的乳化剂;
-填充剂如硅酸盐、聚磷酸盐、用于粉状清洁剂的沸石;
-颜料、色淀或可溶性染料;
-香水;和
-光稳定剂、抗氧化剂和螯合剂。
着色的清洁剂和美饰化妆产品可以包含下列染料:
-无机颜料,例如铁氧化物(氧化铁红、氧化铁黄、氧化铁黑等),群青,氧化铬氯或碳黑;
-天然或合成有机颜料;
-可以在溶剂中加溶的分散染料如HC类型的直接发用染料,例如3号HC红、2号HC蓝以及列于InternationalCosmeticIngredientDictionaryandHandbook,第7版,19997中的所有其他发用染料或列于ColorIndexInternational或SocietyofDyersandColourists中的分散染料;
-染色清漆(可溶性染料的不溶性盐,如阴离子染料的许多Ca、Ba或Al盐);
-可溶性阴离子或阳离子染料,如酸性染料(阴离子性),碱性染料(阳离子性),直接染料,反应性染料或溶剂染料。
通常而言,为了对家用和护体产物着色,所有在电磁辐射的可见光(波长约4000-700nm)中具有吸收的物质是合适的。该吸收通常由下列生色团引起:偶氮-(单-、二-、三-或多-)芪-、类胡萝卜素-、二芳基甲烷-、三芳基甲烷-、呫吨-、吖啶-、喹啉、次甲基-(还有聚甲炔-)、噻唑-、引达胺-、靛酚-、吖嗪-、嗪、噻嗪-、蒽醌-、靛蓝-、酞菁-和其他合成、天然和/或无机生色团。
本发明还涉及家用护理和织物护理产品如下水道清洁剂(draincleaner)、消毒剂溶液、内饰清洁剂、汽车护理产品(例如清洁和/或抛光和保护漆、轮胎、铬(chrome)、乙烯基塑料、皮革、织物、橡胶、塑料和织物)、脱脂剂、抛光剂(玻璃、木材、皮革、塑料、大理石、花岗石和瓷砖等)以及金属抛光剂和清洁剂。抗氧化剂适合保护上述产品以及干燥器片中的香料。本发明还涉及家用护理产品如蜡烛、凝胶蜡烛、空气清新剂和香料油(家用)。
家用清洁和处理剂的典型实例如下表所列:
本发明式(1)的苯并环庚三烯酚酮衍生物例如通过溶于油相或醇相或水相中而掺入,合适的话在升高的温度下溶解。
本发明护体产品和家用产品对这些产品中存在的成分的颜色变化和化学降解具有高稳定性。例如,发现包含染料的本发明组合物具有优异的颜色稳定性。
下列实施例说明本发明。
在下列实施例中,使用下表所列稳定剂:
与现有技术稳定剂的效力对比
实施例1:
制备下列着色基础洗发剂配制剂:
制备该配制剂的下列稳定化和未稳定化样品用于光稳定性测试:
1.未稳定化基础洗发剂配制剂
2.基础洗发配制剂加0.01%式(B-1)化合物
3.基础洗发配制剂加0.01%式(B-2)化合物
4.基础洗发配制剂加0.01%式(B-32)化合物
5.基础洗发配制剂加0.01%式(B-18)化合物
将各配制剂填充到30ml玻璃瓶中并在ATLASSuntestXLS+氙灯(光强度500W/m2,光谱调整到室内条件,样品室温度:32℃)中辐照。
辐照15小时后的结果
样品 | 辐照后的观察结果 |
1 | 褪色/无色 |
2 | 无变化 |
3 | 无变化 |
4 | 无变化 |
5 | 无变化 |
辐照30小时后的结果
样品 | 辐照后的观察结果 |
1 | 无色34 --> |
2 | 无变化 |
3 | 无变化 |
4 | 无变化 |
5 | 褪色 |
所有稳定剂显著提高配制剂的稳定性。本发明式(B-18)的稳定剂额外显示出如下益处:它不改变原有颜色,这对特定所需色调不允许着黄色组分是有利的。
实施例2:
制备下列着色基础洗发剂配制剂:
将该配制剂分别用PURICOLORBlueABL9(BASF,FD&C1号蓝,酸性蓝9)和PURICOLORRedARE33(BASF,D&C33号红,酸性红33)着色。
制备该配制剂的下列稳定化和未稳定化样品用于光稳定性测试:
1.未稳定化基础洗发剂配制剂
2.基础洗发配制剂加0.01%式(B-18)化合物
3.基础洗发配制剂加0.01%TINOGARDTL(BASF)
将各配制剂填充到30ml玻璃瓶中并在ATLASSuntestXLS+氙灯(光强度500W/m2,光谱调整到室内条件,样品室温度:32℃)中辐照。
辐照12小时后着蓝色洗发剂的结果
样品 | 辐照后的观察结果 |
1 | 褪色/无色 |
2 | 无变化 |
样品 | 辐照后的观察结果 |
3 | 无变化 |
辐照25小时后着蓝色洗发剂的结果
样品 | 辐照后的观察结果 |
1 | 褪色/无色 |
2 | 非常轻微的更亮色 |
3 | 褪色/无色 |
辐照10小时后着红色洗发剂的结果
样品 | 辐照后的观察结果 |
1 | 褪色/浅棕色 |
2 | 无变化 |
3 | 无变化 |
辐照25小时后着红色洗发剂的结果
样品 | 辐照后的观察结果 |
1 | 褪色/无色 |
2 | 非常轻微的更亮色 |
3 | 褪色/无色 |
对于两种测试染料,式(B-18)化合物的性能比现有技术的宽带UV吸收剂如TINOGARDTL显著更好。
实施例3:
制备该配制剂的下列稳定化和未稳定化样品用于光稳定性测试:
1.纯蓖麻油
2.含0.1%式(B-32)化合物的蓖麻油
3.含0.1%抗氧化剂TINOGARDTT(BASF)的蓖麻油
4.含0.1%抗氧化剂BHT的蓖麻油
5.含0.1%Quercetin的蓖麻油
将各样品置于RACIMAT中并加热到140℃。调节15L/min的气流。空气流鼓泡通过各加热的样品并随后通过水储槽。由此将通过氧化过程形成的所有挥发性有机化合物通过空气流带入水储槽中。在测量过程中在线监测水储槽的导电率。一旦氧化开始,挥发性有机化合物如甲酸转移到水储槽中,导致导电率快速(指数)增加。直到氧化开始时的时间称为“诱导时间”。
结果列于下表中。
样品 | 诱导时间 |
1 | 7.7小时 |
2 | 10.5小时 |
3 | 9.3小时 |
4 | 9.2小时 |
5 | 8.5小时 |
包含本发明稳定剂的样品2与现有技术的抗氧化剂如TINOGARDTT(Ciba)或BHT相比呈现更好的氧化稳定性,并且也比天然多酚结构体如Quercetin显著更好。
实施例4-15:制备护体和家用配制剂
制备:
在室温下分散组分(A)。
在加热下混合(B),直到对羟基苯甲酸酯完全溶解,然后在温和搅拌下将(B)加入(A)中。
掺混(C)直到完全溶解,并在搅拌下缓慢加入(A)和(B)的混合物中。
掺混(D)直到完全溶解,并在搅拌下缓慢加入(A)、(B)和(C)的混合物中。
该凝胶的透明度可以通过加入少量三乙醇胺(pH=5.6-5.75)而提高。
制备:将表面活性剂和水掺混,直到得到均相溶液。用柠檬酸将pH调至6.0-6.5。加入其他组分,将稳定剂与香料油预混。搅拌该混合物,直到完全溶解。
制备:将各组分以所示顺序在50℃下彻底混合。得到透明均相溶液。
制备家用产品配制剂
制备:将各组分以所示顺序溶解,直到得到透明均相混合物。
制备:将各组分以所示顺序搅拌,直到得到均相混合物。
合成实施例(1):制备B-20
将1,7-二丁基-2,3,4,6-四羟基-5H-苯并环庚烯-5-酮(CAS号16492-78-7)(1.4g)溶于40ml甲苯和0.8ml原乙酸三乙酯中并加热至120℃,直到乙醇蒸发停止。然后将该混合物蒸发至干并在由硅胶过滤以除去深色杂质之后将该残余物由二烷冻干。所得黄色粉末可溶于己烷。
1H-NMR(CDCl3,300MHz):9.00(OH);7.45(d,1H);6.82(d,1H);3.65(dq,1H);3.53(dq,1H);2.85(t,2H);2.72(t,2H);1.88(s,3H);1.48-1.66(m,4H);1.29-1.45(m,4H);1.18(t,3H);0.90(dt,6H)。
13C-NMR(CDCl3,75MHz):13.88;13.95;14.74;22.51;22.75;24.80;26.29;31.23;31.94;34.11;58.45;112.85;119.40;127.11;129.45;129.52;132.62;133.91;144.66;150.61;152.75;181.76。
合成实施例(2):制备B-2
在室温下将0.50g儿茶酚(44.3mmol,98%)和1.28g棓酸辛酯(44.3mmol,98%)溶于30ml邻苯二甲酸盐缓冲液(pH=5)和10mL乙酸乙酯中。
加入3.0mg(21.8U/mg)来自T.versicolor的市售(Sigma-Aldrich)漆酶并将该混合物在室温下搅拌2天。
然后分离有机相并真空浓缩,得到1.02g粗化合物B-2。在由乙醇/水重结晶之后以深橙色粉末得到1.26g所需产物B-2。熔点:79℃(分解)。
1H-NMR(DMSO,300MHz):14.77(s,1H,OH),10.00(s,2H,2OH);8.27(s,1H);7.612(m,2H);7.48(d,1H);4.28(t,2H);1.73(m,2H);1.16-1-42(m,10H);0.85(t,3H)。
合成实施例(3):制备B-1
在室温下将6.74g儿茶酚(60mmol,98%)和8.66g棓酸丙酯(40mmol,98%)溶于400mL磷酸盐缓冲液(pH=5)和120mL乙酸乙酯中。
加入45.2mg(21.8U/mg)来自T.versicolor的市售漆酶并将该混合物在室温下搅拌4天。
然后分离有机相并真空浓缩,得到13.40g粗产物。在由水重结晶之后以橙色粉末得到7.34g所需产物B-1。熔点:139℃。
1H-NMR(DMSO,300MHz):14.75(s,1H,OH),10.15(s,1H,OH);9.90(s,1H,OH);8.26(s,1H);7.61(d,1H);7.60(s,1H);7.48(d,1H);4.25(t,2H);1.76(m,2H),0.99(t,3H)。
合成实施例(4):制备B-32
向3.00g红棓酚在40ml吡啶中的溶液中滴加2.56ml乙酸酐。在100℃下搅拌1小时之后将该混合物蒸发至干并将橙色残余物悬浮于乙醚中。滤出沉淀并在真空中干燥,得到0.59g粗化合物B-32。在乙醚/乙酸乙酯(1:1)中沸腾之后以黄色粉末得到0.42g所需产物。
1H-NMR(DMSO,360MHz):15.29(s,1H);11.38(s,1H);7.57(d,J=11.6,1H);7.35(d,J=8.95,1H);6.99(s,1H);6.78(dd,1H);2.34(s,3H);2.30(s,3H)。
合成实施例(5):制备B-23
将红棓酚(0.50g)溶于20ml甲苯和0.43ml原乙酸三乙酯中并加热至120℃,直到乙醇蒸发停止。然后将所得橙色悬浮液蒸发至干并将残余物在二氯甲烷中搅拌。滤出沉淀并在真空中于25℃下干燥。以橙色粉末分离出450mg所需产物。
1H-NMR(CDCl3,360MHz):14.61(s,1H);8.56(s,1H);7.34(d,J=11.5,1H);7.19(d,J=9.5,1H);6.86-6.80(m,2H);3.72-3.59(m,2H);1.92(s,3H);1.24(t,J=7.1,3H)。
合成实施例(6):制备B-36
将化合物B-37悬浮于10.0mlHCl水溶液0.1N溶液并在25℃下搅拌18小时。滤出橙黄色沉淀并在真空中干燥。以米色粉末分离出0.318g所需产物。
1H-NMR(DMSO,360MHz):15.26(s,1H);7.56(d,1H);7.33(d,1H);6.98(s,1H);6.65(dd,1H);2.30(s,3H)。
合成实施例(7):制备B-37
在室温下向0.636gB-23在6.0ml吡啶中的溶液中加入0.207ml乙酸酐。将棕橙色溶液在室温下搅拌1.5小时,加入30.0ml冰水中并在0℃下搅拌15分钟。滤出橙色悬浮液并在真空中干燥。以橙色粉末分离出0.620g所需产物。
1H-NMR(DMSO,360MHz):14.78(s,1H);7.68(d,1H);7.43(d,1H);7.26(s,1H);6.82(dd,1H);3.59-3.56(m,2H);2.31(s,3H);1.89(s,3H);1.16(t,3H)。
合成实施例(8):制备B-38
将化合物B-1(1.50g)溶于35ml甲苯和1.89ml原乙酸三乙酯中并加热到120℃,直到乙醇蒸发停止。然后将所得橙色悬浮液蒸发至干并将该残余物在10.0ml乙醚中搅拌。滤出沉淀并在真空中于25℃下干燥。以黄色粉末分离出1.20g所需产物。
1H-NMR(CDCl3,360MHz):8.39(s,1H);8.30(s,1H);7.77(s,1H);7.57(d,1H);7.34(d,1H);4.31(t,2H);3.70-3.57(m,2H);1.98(s,3H);1.84-1.82(m,2H);1,24(t,3H);1.06(t,3H)。
合成实施例(9):制备B-39
在室温下向0.40gB-23在4.0ml吡啶中的溶液中加入2.651ml乙酸酐。将棕色混合物在室温下搅拌20小时,加入40.0ml冰水中并在0℃下搅拌15分钟。滤出米色悬浮液并将橙黄色残余物在真空中干燥。以黄色粉末分离出0.198g所需产物。
1H-NMR(CDCl3,360MHz):7.14(d,1H);6.92(s,1H);6.78(d,1H);6.52-6.47(m,1H);3.703.54(m,2H);2.35(s,3H);2.29(s,3H);1.87(s,3H);1.21(t,3H)。
合成实施例(10):制备B-5
在室温下将化合物B-1(0.35g)溶于4.0ml吡啶中。滴加0.50ml乙酸酐并将该溶液在室温下搅拌16小时。然后将该混合物加入5.0ml冰水中并在15℃下搅拌30分钟。将黄色沉淀滤出,用水洗涤并在真空中于30℃下干燥。以黄色粉末分离出0.337g所需产物。
1H-NMR(DMSO,360MHz):8.45(s,1H);8.16(d,1H);7.88(d,1H);7.50(s,1H);4.31(t,2H);2.38(s,3H);2.33(s,3H);2.30(s,3H);1.83-1.77(m,2H);1.03(t,3H)。
合成实施例(11):制备B-7
在室温下向0.20gB-41在4.0mlHCl水溶液0.1N溶液中的混合物中加入0.5mlTHF。将棕色悬浮液在60℃下搅拌6小时。然后将该混合物蒸发至干并将残余物悬浮于水中。滤出棕色沉淀并在真空中于25℃下干燥。以棕红色粉末分离出0.12g所需产物。
1H-NMR(DMSO,360MHz):14.36(s,1H);10.75(s,1H);8.35(s,1H);7.70(s,1H);7.63(d,1H);7.37(d,1H);4.15(t,2H);2.21(s,3H);1.67-1.61(m,2H);0.87(t,3H)。
合成实施例(12):制备B-41
在室温下将化合物B-38(490mg)溶于2.0ml吡啶中。滴加0.154ml乙酸酐并将棕色溶液在25℃下搅拌1小时。然后将该混合物加入5.0ml冰水中并在15℃下搅拌30分钟。滤出黄色沉淀,用水洗涤并在真空中于30℃下干燥。以黄色粉末分离出0.33g所需产物。
1H-NMR(DMSO,360MHz):8.40(s,1H);7.85(d,1H);7.60(d,1H);7.54(s,1H);4.25(t,2H);3.53-3.50(m,3H);2.30(s,3H);1.88(s,3H);1.81-1.71(m,2H);1.15(t,3H);0.98(t,3H)。
Claims (13)
1.下式的苯并环庚三烯酚酮衍生物作为UV吸收剂在保护护体和家用产品以防光解中的用途:
其中
R1、R2和R7相互独立地为氢、C1-C30烷基或COR8;
R3为氢或COOR9;
R4为氢或C1-C30烷基;
R5为氢、羟基、C1-C3烷氧基或-O-(CO)-R10;
R6为氢、C1-C30烷基或COR8;或
R5和R6可以一起形成5或6元环;或
R6和R7一起形成5或6元环;和
R8、R9、R10相互独立地为C1-C30烷基,
其中所述护体产品选自护肤产品、沐浴和淋浴添加剂、护发产品和美饰制剂,以及所述家用产品选自家用清洁和处理剂。
2.根据权利要求1的用途,其中
R1为氢、COR8或C1-C30烷基;
R2、R4和R5为氢;
R3为COOR9;
R6和R7相互独立地为氢、C1-C30烷基或COR8;或
R6和R7一起形成5或6元环;和
R8如权利要求1中所定义。
3.根据权利要求2的用途,其中
R1为氢或CO-CH3;
R2、R4和R5为氢;
R3为COO-C3H7;
R6和R7相互独立地为氢或CO-CH3;或
R6和R7一起形成5或6元环。
4.根据权利要求1的用途,其中
R1、R2和R7相互独立地为氢、甲基或-CO-CH3;
R3为氢或-COOR9;
R4为氢或C1-C30烷基;
R5为氢、甲氧基或-O-(CO)-CH3;
R6为氢、甲基或-CO-CH3;或
R5和R6可以一起形成5或6元环;或
R6和R7一起形成5或6元环;和
R9为C1-C10烷基。
5.根据权利要求1-4中任一项的用途,其中使用下式化合物:
6.根据权利要求1的用途,其中所述护体产品选自含有香料和芳香物质的制剂、洁齿剂、祛臭和止汗制剂、光保护配制剂和含有活性成分的制剂。
7.根据权利要求1的用途,其中所述护体产品选自护体油、爽身水、护体凝胶、处理霜、皮肤保护软膏、剃须制剂和爽身粉。
8.根据权利要求6的用途,其中所述护体产品含有香料和芳香物质,其选自香味剂、香水、花露水和剃须液。
9.根据权利要求1的用途,其中所述护体产品是护发产品且选自洗发剂、头发调理剂、发用定型和处理产品、烫发剂、固发剂和染发或漂发剂。
10.根据权利要求9的用途,其中所述发用定型和处理产品选自发胶、发蜡和发用凝胶。
11.根据权利要求6的用途,其中所述护体产品是选自选自唇膏、指甲油、眼影、睫毛油、干湿美容品、胭脂、底粉、脱毛剂和太阳油的美饰制剂。
12.根据权利要求6的用途,其中所述护体产品含有活性成分且选自激素制剂、维生素制剂、植物提取物制剂和抗菌制剂。
13.根据权利要求1的用途,其中所述家用清洁和处理剂选自洗涤、漂洗和餐具洗涤剂,鞋油,抛光蜡,地板清洁剂和地板蜡,通用清洁剂,浴盆和厕所清洁剂,厨房清洁剂,车用洗剂和蜡,中性、酸性和碱性清洁剂,金属、玻璃和陶瓷清洁剂,织物护理剂,除锈、脱色和去污剂,漂白剂,家具和多用途抛光剂,表面保护配制剂,成膜配制剂,空气质量保护配制剂和蜡烛。
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CN106479378A (zh) * | 2016-10-14 | 2017-03-08 | 柳州立洁科技有限公司 | 一种鞋油 |
CN106479377A (zh) * | 2016-10-14 | 2017-03-08 | 柳州立洁科技有限公司 | 一种鞋油及其制备方法 |
CN106479381A (zh) * | 2016-10-14 | 2017-03-08 | 柳州立洁科技有限公司 | 一种黑色皮鞋油 |
CN106479379A (zh) * | 2016-10-14 | 2017-03-08 | 柳州立洁科技有限公司 | 一种环保鞋油及其制备方法 |
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