CN1938348A - 含有二烯丙基胺的聚合物 - Google Patents
含有二烯丙基胺的聚合物 Download PDFInfo
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- CN1938348A CN1938348A CNA2005800097843A CN200580009784A CN1938348A CN 1938348 A CN1938348 A CN 1938348A CN A2005800097843 A CNA2005800097843 A CN A2005800097843A CN 200580009784 A CN200580009784 A CN 200580009784A CN 1938348 A CN1938348 A CN 1938348A
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- Prior art keywords
- polymkeric substance
- acid
- monomer
- ester
- methyl
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- NCYCYZXNIZJOKI-UHFFFAOYSA-N vitamin A aldehyde Natural products O=CC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C NCYCYZXNIZJOKI-UHFFFAOYSA-N 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 235000019386 wax ester Nutrition 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000010497 wheat germ oil Substances 0.000 description 1
- 210000004885 white matter Anatomy 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- WIBCVGUGRCGRSG-UHFFFAOYSA-N zinc oxygen(2-) 1H-pyridine-2-thione Chemical compound [O-2].[Zn+2].SC1=NC=CC=C1 WIBCVGUGRCGRSG-UHFFFAOYSA-N 0.000 description 1
- GAWWVVGZMLGEIW-GNNYBVKZSA-L zinc ricinoleate Chemical group [Zn+2].CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O.CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O GAWWVVGZMLGEIW-GNNYBVKZSA-L 0.000 description 1
- 229940100530 zinc ricinoleate Drugs 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
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Abstract
本发明涉及含有作为单体组分的(多)氧化烯取代的二烯丙基胺、烯属不饱和单体B、任选的一种或多种其它烯属不饱和单体以及任选的固化剂的聚合物。本发明进一步涉及所述聚合物作为化妆品制剂中的添加剂的用途。
Description
本发明涉及含有作为单体结构单元的(多)氧化烯取代的二烯丙基胺、烯属不饱和单体B和如果合适的话还有一种或多种其它烯属不饱和单体以及如果合适的话还有交联剂的聚合物,以及涉及该聚合物作为化妆品制剂中的添加剂的用途。
US 3,585,148描述了乙氧基化的季化二烯丙基胺和丙烯酰胺的共聚物及其作为分散在非油性连续相中的油的破乳剂的用途。
在EP 111 965和EP 112 592中要求保护聚乙氧基化的二烯丙基胺在洗涤剂中的用途。同样公开了由二烯丙基胺合成乙氧基化的二烯丙基胺的方法,以及均聚物的制备方法。
US 5,478,883描述了二烯丙基胺和氧化乙烯和氧化丙烯的反应产物作为乳液聚合中的水溶性非离子表面活性物质的用途。
对于发用化妆品,例如使用成膜聚合物作为调理剂以改进干和湿梳理性、触感、光泽和外观,并且赋予头发抗静电的性质。
标准的商用阳离子调理剂聚合物例如是阳离子性羟乙基纤维素、基于N-乙烯基吡咯烷酮的阳离子聚合物(例如N-乙烯基吡咯烷酮和季化N-乙烯基咪唑的共聚物)或者丙烯酰胺与二烯丙基二甲基氯化铵的共聚物。
含有二烯丙基胺衍生物作为单体结构单元的聚合物例如是二烯丙基二甲基氯化铵(DADMAC)的均聚物和共聚物。
形成本发明基础的目的是提供可以以成本有效的方式制备以用于化妆品制剂中的阳离子聚合物,特别是作为调理剂聚合物的阳离子聚合物。在使用时,特别是对于头发护理,这些聚合物应当形成具有良好机械性能的膜并且使头发具有良好的湿和干梳理性、不打结、强度以及良好的感观性质如触感、头发体积和可处理性。此外该聚合物还应当易于洗掉,与其它的配制成分相容,因而能够作为透明的含水制剂使用。
现已发现含有下列单体结构单元的聚合物作为化妆品制剂中的添加剂具有有利的性质:
a)至少一种中性或季铵形式的具有通式I的二烯丙基胺(单体A)
其中
A-O是C1-C12氧化烯、氧化苯乙烯或其任意混合物,
n是2-200的整数,
x是0或1,
R1是氢,C1-C20烷基,C2-C20链烯基,C5-C10环烷基或任选取代的苄基,
R2是氢,C1-C30烷基,C5-C8环烷基,C6-C20芳基,C1-C30链烷酰基,C7-C21芳酰基,硫酸(半)酯,磷酸酯,氨基或铵,R3可以相同或不同并且是氢,C1-C20烷基,C2-C20链烯基,C5-C10环烷基或芳基,
b)至少一种选自由如下单体组成的组的烯属不饱和单体(单体B)
i N-乙烯基内酰胺,
ii N-乙烯基酰胺,
iii N-乙烯基咪唑,
iv 不同于单体A的N,N-二烯丙基胺,以及这些单体或其盐的任意混合物,
c)如果合适的话,一种或多种烯属不饱和单体C,
d)如果合适的话,至少一种交联剂。
C1-C12氧化烯应当理解为例如表示氧化乙烯、氧化丙烯、1-氧化丁烯、氧化丁烯的异构体,更高级的氧化烯,如氧化十二碳烯、氧化苯乙烯,及其任意混合物。优选氧化烯是氧化乙烯或氧化乙烯与氧化丙烯的混合物。
在混合物的情况下,各种结构单元可以以不同的顺序排列,例如嵌段、交替或无规形式排列。
n是2-200,优选5-150,特别优选10-100的整数。
C1-C20烷基或C1-C30烷基应当理解为表示具有至多20或30个,优选1-10个碳原子的线性或支化的饱和烃链,例如甲基、乙基、正丙基、异丙基、正丁基、叔丁基、正戊基、新戊基、正己基、2-乙基己基、正辛基、1-癸基、1-十二烷基等,优选甲基、乙基、正丙基或异丙基。
C5-C8环烷基应当理解为表示具有5-8个碳原子的环脂族基团,例如环戊基、环己基、环庚基或环辛基,其任选可以由1、2、3或4个上述C1-C4烷基取代。
C6-C20芳基是可以经由亚烷基单元键合且可以具有6-20个碳原子的芳基,例如苄基、苯基或乙基苯基。
C1-C30链烷酰基是经由羰基键合的烷基。特别可以提到甲酰基、乙酰基、丙酰基和正丁酰基。
C7-C21芳酰基对应于C7-C21芳基羰基,并且是经由羰基键合的芳基。特别可以提到苯甲酰基和萘甲酰基。
R1优选是氢,C1-C6烷基,例如甲基、乙基、正丙基、正丁基或苄基,特别优选氢或甲基。
R2优选是氢,C1-C6烷基,例如甲基、乙基、正丙基、正丁基或苯基,特别优选氢或甲基。
R2还可以是NR’R”(氨基)或NR’R”R+(铵),其中R’、R”、R可以在每种情况下相互独立地是相同或不同的,并且可以是氢,直链或支化的C1-C20烷基或直链或支化的C1-C20羟烷基,优选氢、甲基、乙基或2-羟乙基。
R3是两个N-烯丙基的取代基且可以相同或不同,并且是氢,C1-C20烷基,C2-C20链烯基,C5-C10环烷基或芳基。在优选的实施方案中R3是氢。
使用的单体A优选是具有2-100摩尔氧化烯且优选带有氢或甲基作为另外的基团R1的烷氧基化二烯丙基胺。
在此优选的氧化烯是氧化乙烯或氧化丙烯,其可以以类似无规、交替或嵌段的顺序单独存在于单体A中。特别优选的氧化烯是氧化乙烯。
特别地,具有通式I的单体A以季化形式存在于本发明的聚合物中,其中x是1且R1是甲基。
N-乙烯基内酰胺i任选具有一个或多个取代基,例如C1-C6烷基取代基。
优选的N-乙烯基内酰胺是N-乙烯基吡咯烷酮、N-乙烯基哌啶酮、N-乙烯基己内酰胺、N-乙烯基-5-甲基-2-吡咯烷酮、N-乙烯基-5-乙基-2-吡咯烷酮、N-乙烯基-6-甲基-2-哌啶酮、N-乙烯基-6-乙基-2-哌啶酮、N-乙烯基-7-甲基-2-己内酰胺、N-乙烯基-7-乙基-2-己内酰胺。
优选的N-乙烯基酰胺化合物ii是在羧酸单元中具有1-4个碳原子且在氮原子上具有氢或C1-C4烷基,特别是甲基或乙基的那些。
可以提到的实例是N-乙烯基甲酰胺、N-乙烯基-N-甲基甲酰胺、N-乙烯基乙酰胺、N-乙烯基-N-甲基乙酰胺、N-乙烯基-N-乙基乙酰胺、N-乙烯基丙酰胺、N-乙烯基-N-甲基丙酰胺和N-乙烯基丁酰胺。
优选的N-乙烯基咪唑iii是具有通式II的N-乙烯基咪唑:
其中R4至R6相互独立地是氢,C1-C4烷基如甲基或乙基,或者是苯基。N-乙烯基咪唑也可以作为盐以季铵形式存在。
优选的N,N-二烯丙基胺iv是具有通式III的N,N-二烯丙基胺:
其中R10是氢或C1-C4烷基。二烯丙基胺也可以以它们的盐形式存在。特别优选二烯丙基二甲基氯化铵(DADMAC)。
N-乙烯基咪唑iii和N,N-二烯丙基胺iv的优选盐是氯化物和硫酸盐。
本发明特别提供了含有作为单体B的N-乙烯基己内酰胺或N-乙烯基吡咯烷酮或其混合物的那些聚合物。
单体A与B的摩尔比通常为20∶1至1∶50,优选10∶1至1∶50,特别是1∶1至1∶30。
除了单体A和B以外,该聚合物还可以任选含有单体C。合适的单体C原则上是不同于A和B的所有烯属不饱和化合物。
合适的单体C优选选自:α,β-烯属不饱和单羧酸和二羧酸与C1-C30链烷醇和C1-C30链烷二醇的酯,α,β-烯属不饱和单羧酸和二羧酸与具有伯或仲氨基的C2-C30氨基醇的酰胺,α,β-烯属不饱和单羧酸的伯氨基化物及其N-烷基和N,N-二烷基衍生物,乙烯醇和烯丙醇与C1-C30单羧酸的酯,乙烯基醚,乙烯基芳族化合物,乙烯基卤,偏二卤代乙烯,C1-C8单烯烃,具有至少两个共轭双键的非芳族烃及其混合物。
合适的单体C是(甲基)丙烯酸甲酯、乙基丙烯酸甲酯、(甲基)丙烯酸乙酯、乙基丙烯酸乙酯、(甲基)丙烯酸叔丁酯、乙基丙烯酸叔丁酯、(甲基)丙烯酸正辛酯、(甲基)丙烯酸1,1,3,3-四甲基丁酯、(甲基)丙烯酸乙基己酯、(甲基)丙烯酸正壬酯、(甲基)丙烯酸正癸酯、(甲基)丙烯酸正十一烷基酯、(甲基)丙烯酸十三烷基酯、(甲基)丙烯酸十四烷基酯、(甲基)丙烯酸十五烷基酯、(甲基)丙烯酸十六烷基酯、(甲基)丙烯酸十七烷基酯、(甲基)丙烯酸十九烷基酯、(甲基)丙烯酸二十烷基酯、(甲基)丙烯酸二十二烷基酯、(甲基)丙烯酸二十四烷基酯、(甲基)丙烯酸二十六烷基酯、(甲基)丙烯酸三十烷基酯、(甲基)丙烯酸棕榈油基酯、(甲基)丙烯酸油基酯、(甲基)丙烯酸亚油基酯、(甲基)丙烯酸亚麻基酯、(甲基)丙烯酸硬脂基酯、(甲基)丙烯酸月桂基酯,及其混合物。
可以使用的单体C例如是丙烯酸、甲基丙烯酸或马来酸的烷基酯或羟烷基酯,或者是经2-50摩尔氧化乙烯、氧化丙烯、氧化丁烯或其混合物烷氧基化的C1-C18醇与丙烯酸、甲基丙烯酸或马来酸的酯。合适的单体C是丙烯酸2-羟乙基酯、甲基丙烯酸2-羟乙基酯、乙基丙烯酸2-羟乙基酯、丙烯酸2-羟丙基酯、甲基丙烯酸2-羟丙基酯、丙烯酸3-羟丙基酯、甲基丙烯酸3-羟丙基酯、丙烯酸3-羟丁基酯、甲基丙烯酸3-羟丁基酯、丙烯酸4-羟丁基酯、甲基丙烯酸4-羟丁基酯、丙烯酸6-羟己基酯、甲基丙烯酸6-羟己基酯、丙烯酸3-羟基-2-乙基己基酯、甲基丙烯酸3-羟基-2-乙基己基酯等。
(甲基)丙烯酰胺是丙烯酸酰胺或甲基丙烯酸酰胺。合适的单体C还是丙烯酰胺、甲基丙烯酰胺、N-甲基(甲基)丙烯酰胺、N-乙基(甲基)丙烯酰胺、N-丙基(甲基)丙烯酰胺、N-正丁基(甲基)丙烯酰胺、N-叔丁基(甲基)丙烯酰胺、N-正辛基(甲基)丙烯酰胺、N-(1,1,3,3-四甲基丁基)(甲基)丙烯酰胺、N-乙基己基(甲基)丙烯酰胺、N-正壬基(甲基)丙烯酰胺、N-正癸基(甲基)丙烯酰胺、N-正十一烷基(甲基)丙烯酰胺、N-十三烷基(甲基)丙烯酰胺、N-十四烷基(甲基)丙烯酰胺、N-十五烷基(甲基)丙烯酰胺、N-十六烷基(甲基)丙烯酰胺、N-十七烷基(甲基)丙烯酰胺、N-十九烷基(甲基)丙烯酰胺、N-二十烷基(甲基)丙烯酰胺、N-二十二烷基(甲基)丙烯酰胺、N-二十四烷基(甲基)丙烯酰胺、N-二十六烷基(甲基)丙烯酰胺、N-三十烷基(甲基)丙烯酰胺、N-棕榈油基(甲基)丙烯酰胺、N-油基(甲基)丙烯酰胺、N-亚油基(甲基)丙烯酰胺、N-亚麻基(甲基)丙烯酰胺、N-硬脂基(甲基)丙烯酰胺、N-月桂基(甲基)丙烯酰胺、N,N-二甲基(甲基)丙烯酰胺、N,N-二乙基(甲基)丙烯酰胺、吗啉基(甲基)丙烯酰胺。
在优选的实施方案中,单体C是甲基丙烯酰胺。
其它合适的单体C是乙酸乙烯酯、丙酸乙烯酯、丁酸乙烯酯及其混合物。
合适的单体C还可以是乙烯、丙烯、1-丁烯、2-丁烯、异戊二烯、异丁烯、丁二烯、环己二烯、苯乙烯、叔丁基苯乙烯、α-甲基苯乙烯、乙烯基甲苯、丙烯腈、甲基丙烯腈、氯乙烯、偏二氯乙烯、氟乙烯、偏二氟乙烯及其任意混合物。
单体C可以单独或者以任意混合物的形式使用。
聚合物通常含有1-95摩尔%的单体A,5-99摩尔%的单体B和0-50摩尔%的单体C。
氧化烯类化合物可以例如通过在多个步骤中进行二烯丙基胺的烷氧基化而制备。在第一步中,在存在或不存在溶剂下使二烯丙基胺与至少一当量的氧化烯反应。在催化剂存在下进一步使由此得到的前体与氧化烯反应,其中可以使用现有技术已知用于氧化烯聚合的所有催化剂,合适的催化剂是现有技术已知用于氧化烯聚合且与胺相容的所有催化剂。许多催化剂的综述例如在F.E.Bailey,Jr,J.V.Koleske,氧化烯及其聚合物,NY和Basel 1991,第33页及随后各页中给出。特别优选使用碱性催化剂如NaOH、KOH、CsOH、叔丁醇钾、NaOMe或这类碱与冠醚的混合物。
可以进一步对氧化烯和二烯丙基胺的加成产物进行官能化。例如可以采用烷基化剂进行季铵化,可以将OH转化为硫酸酯、磺酸酯、磷酸酯或膦酸酯。可以通过质子化(例如用羧酸如乳酸,或者无机酸如磷酸、硫酸和氢氯酸)或者通过季铵化(例如用烷基化剂如C1-C4烷基卤或硫酸C1-C4烷基酯)将胺的氮转化为带电荷的阳离子基团。
所述烷基化剂的实例是氯乙烷、溴乙烷、氯甲烷、溴甲烷、硫酸二甲酯和硫酸二乙酯。通常可以在聚合之前或之后进行质子化或季铵化。这导致阳离子、阴离子、两性或内铵盐型结构。
聚合物的制备
本发明还提供了制备本发明聚合物的方法,其中使单体A和B以及任选的C和任选的交联剂发生自由基聚合。
聚合物可以根据常用聚合方法如本体聚合、溶液聚合以及在单体的溶解度较低的情况下也可以按照乳液聚合、分散聚合或悬浮聚合而制备。如果聚合物在反应混合物中的溶解度足够低,那么同样可以按照沉淀聚合进行聚合反应。
对于上面所述的聚合方法,优选在排除氧的条件下操作,特别是在惰性气流中,特别优选在氮气流中操作。对于所有的聚合方法使用常用设备,例如搅拌釜、搅拌釜级联、高压釜、管式反应器和捏合机。优选溶液和乳液聚合方法。如果通过自由基水乳液聚合制备本发明聚合物,将表面活性剂或保护性胶体加入反应介质中是有利的。合适的乳化剂和保护性胶体的列举例如在Houben Weyl,Methoden der organischen Chemie(有机化学方法),第XIV/1卷,大分子物质,Georg Thieme Verlag,Stuttgart,1961,第411页及其随后各页中给出。
聚合可以在溶剂或稀释剂中进行,例如在甲苯、邻二甲苯、对二甲苯、枯烯、氯苯、乙苯、工业级烷基芳族混合物、环己烷、工业级脂族混合物、丙酮、环己酮、四氢呋喃、二烷、二醇及二醇衍生物、聚亚烷基二醇及其衍生物、乙醚、叔丁基甲基醚、乙酸甲酯、异丙醇、乙醇、水或其混合物如异丙醇/水混合物中进行。使用的溶剂或稀释剂优选是水,其任选带有含量为至多60重量%的醇或二醇。特别优选使用水。
可以在20-300℃,优选40-150℃的温度下进行聚合。
引发剂
优选在形成自由基的化合物存在下进行聚合。基于聚合中使用的单体,通常使用至多30重量%,优选0.05-15重量%,特别优选0.2-8重量%的这些化合物。在多组分引发剂体系的情况下(例如氧化还原引发剂体系),以上给出的重量是指各组分的总重量。
合适的聚合引发剂例如是过氧化物、氢过氧化物、过二硫酸酯(盐)、过碳酸酯(盐)、过氧酯、过氧化氢和偶氮化合物。可以是水溶性或水不溶性的引发剂实例是过氧化氢、过氧化二苯甲酰、过二碳酸二环己基酯、过氧化二月桂酰、过氧化甲乙酮、氢过氧化二叔丁基、过氧化乙酰丙酮、氢过氧化叔丁基、氢过氧化枯烯、过新癸酸叔丁基酯、过新戊酸叔戊基酯、过苯甲酸叔丁基酯、过二硫酸锂、过二硫酸钠、过二硫酸钾和过二硫酸铵和偶氮二异丁腈、2,2’-偶氮二(2-脒基丙烷)盐酸盐。
可以单独或以相互间的混合物形式使用引发剂,该混合物例如是过氧化氢和过二硫酸钠的混合物。对于在含水介质中的聚合,优选使用水溶性引发剂。
也可以使用已知的氧化还原引发剂体系作为聚合引发剂。该氧化还原引发剂体系包含至少一种含有过氧基团的化合物以及氧化还原助引发剂,例如具有还原作用的硫化合物,例如碱金属和铵的亚硫酸氢盐、亚硫酸盐、硫代硫酸盐、连二亚硫酸盐和连四硫酸盐。例如可以使用过二硫酸盐与碱金属或铵的亚硫酸氢盐的组合,例如过二硫酸铵和亚硫酸氢铵(Ammoniumdisulfite)的组合。含有过氧基团的化合物相对于氧化还原助引发剂的用量可以是30∶1至0.05∶1。
与引发剂或氧化还原引发剂体系结合,另外还可以使用过渡金属催化剂,例如铁、钴、镍、铜、钒和锰的盐。合适的盐例如是硫酸亚铁(II)、氯化钴(II)、硫酸镍(II)或氯化亚铜(I)。基于单体,还原性过渡金属盐使用的浓度是0.1ppm至1000ppm。例如,可以使用过氧化氢与铁(II)盐的组合,如0.5-30%过氧化氢和0.1-500ppm莫尔盐的组合。
对于在有机溶剂中进行聚合,也可以联合使用氧化还原助引发剂和/或过渡金属催化剂与上述引发剂的组合,例如苯偶姻、二甲基苯胺、抗坏血酸和可溶于有机物的重金属(例如铜、钴、铁、锰、镍和铬)配合物。基于单体的用量,氧化还原助引发剂或过渡金属催化剂的常用量约为0.1-1000ppm。
分子量
可以通过选择反应参数,例如溶剂、调节剂、交联剂、引发剂用量、反应时间和/或温度来影响聚合物的分子量(数均分子量Mn或重均分子量Mw)。
根据对聚合条件的选择,可以建立例如1000-2000000,优选5000-50000的重均分子量(Mw)。通过凝胶渗透色谱法(GPC)测定Mw。
根据H.Fikentscher,Cellulose-Chemie,第13卷,第58-64和71-74页(1932)在pH为7的水溶液中在25℃的温度下并且在共聚物钠盐的聚合物浓度为1重量%的条件下测定共聚物的钠盐水溶液的K值。
调节剂
为了控制聚合物的平均分子量,在调节剂存在下进行共聚反应通常是有利的。为此,可以使用常用调节剂,例如含有SH基团的有机化合物,例如2-巯基乙醇、2-巯基丙醇、3-巯基丙酸、半胱氨酸、N-乙酰基半胱氨酸,以及次磷酸钠或亚硫酸氢钠。使用的调节剂优选是链烷硫醇。还可以使用两种或更多种调节剂的混合物。
可以使用的链烷硫醇是碳链长度为C10-C22的线性和支化链烷硫醇。优选线性链烷硫醇,特别是链长为C12-C22,非常特别是链长为C12-C18的链烷硫醇。可以提到的优选链烷硫醇是正癸烷硫醇、正十二烷硫醇、叔十二烷硫醇、正十四烷硫醇、正十五烷硫醇、正十六烷硫醇、正十七烷硫醇、正十八烷硫醇、正十九烷硫醇、正二十烷硫醇、正二十二烷硫醇。特别优选线性的偶数链烷硫醇。
链烷硫醇同样可以以混合物使用。通常将链烷硫醇与单体一起加入聚合中。基于单体,聚合调节剂的通常用量为0.1-10重量%。
可以通过选择合适的溶剂来影响平均分子量。例如在具有苄基H原子的稀释剂存在下进行聚合反应会由于链转移而导致平均分子量减小。
交联剂
为了提高聚合物的分子量,在交联剂存在下进行共聚可能是有利的。
合适的交联剂例如是至少二元醇的丙烯酸酯、甲基丙烯酸酯、烯丙基醚或乙烯基醚。在此,母体醇的OH可以完全或部分醚化或酯化;然而,交联剂含有至少两个烯属不饱和基团。
母体醇的实例是二价醇,例如1,2-乙二醇、1,2-丙二醇、1,3-丙二醇、1,2-丁二醇、1,3-丁二醇、2,3-丁二醇、1,4-丁二醇、1,4-二羟基-2-丁烯、1,2-戊二醇、1,5-戊二醇、1,2-己二醇、1,6-己二醇、1,10-癸二醇、1,2-十二烷二醇、1,12-十二烷二醇、新戊二醇、3-甲基-1,5-二羟基-戊烷、2,5-二甲基-1,3-己二醇、2,2,4-三甲基-1,3-戊二醇、1,2-环己二醇、1,4-环己二醇、1,4-二(羟甲基)环己烷、新戊二醇羟基新戊酸单酯、2,2-二(4-羟苯基)-丙烷、2,2-二[4-(2-羟丙基)苯基]-丙烷、二甘醇、三甘醇、四甘醇、二丙二醇、三丙二醇、四丙二醇、3-硫代-1,5-戊二醇,以及在每种情况下分子量为200-10 000的聚乙二醇、聚丙二醇和聚四氢呋喃。除了氧化乙烯或氧化丙烯的均聚物之外,还可以使用氧化乙烯或氧化丙烯的嵌段共聚物,或者含有呈引入形式的氧化乙烯和氧化丙烯基团的共聚物。具有两个以上OH的母体醇的实例是三羟甲基丙烷,甘油,季戊四醇,1,2,5-戊三醇,1,2,6-己三醇,三乙氧基三聚氰酸,脱水山梨糖醇,糖如蔗糖、葡萄糖、甘露糖。当然也可以在与氧化乙烯或氧化丙烯反应以后以相应的乙氧基化物或丙氧基化物的形式使用多元醇。还可以通过与表氯醇反应而首先将多元醇转化为相应的缩水甘油醚。
其它合适的交联剂是乙烯基酯或一元不饱和醇与烯属不饱和C3-C6羧酸的酯,该烯属不饱和C3-C6羧酸例如是丙烯酸、甲基丙烯酸、衣康酸、马来酸或富马酸。该醇的实例是烯丙醇、3-羟基-1-丁烯、1-羟基-5-己烯、3-羟基-1-辛烯、1-羟基-9-癸烯、二聚环戊烯基醇、1-羟基-10-十一碳烯、肉桂醇、香茅醇、巴豆醇或顺式-1-羟基-9-十八碳烯。然而,还可将一元不饱和醇用多元羧酸例如丙二酸、酒石酸、偏苯三甲酸、邻苯二甲酸、对苯二甲酸、柠檬酸或琥珀酸酯化。
其它合适的交联剂是不饱和羧酸例如油酸、巴豆酸、肉桂酸或10-十一烷酸与上述多元醇的酯。
合适的交联剂也可以是具有至少两个双键的直链或支化的、线性或环状的脂族或芳族烃,其中的至少两个双键在脂族烃的情况下不发生共轭,例如二乙烯基苯、二乙烯基甲苯、1,7-辛二烯、1,9-癸二烯、4-乙烯基-1-环己烯、三乙烯基环己烷或分子量为200-20 000的聚丁二烯。
合适的交联剂也可以是丙烯酰胺、甲基丙烯酰胺和至少二元胺的N-烯丙基胺。这类胺例如是1,2-二氨基甲烷、1,2-二氨基乙烷、1,3-二氨基丙烷、1,4-二氨基丁烷、1,6-二氨基己烷、1,12-十二烷二胺、哌嗪、二亚乙基三胺或异佛尔酮二胺。同样合适的是烯丙基胺和不饱和羧酸如丙烯酸、甲基丙烯酸、衣康酸、马来酸或如上所述的至少二元的羧酸的酰胺。
特别合适的交联剂是三烯丙基胺和三烯丙基单烷基铵盐,例如三烯丙基甲基氯化铵或者三烯丙基甲基甲基硫酸铵。
还合适的是尿衍生物、至少二价的酰胺、氰脲酸酯或尿烷的N-乙烯基化合物,例如尿素、亚乙基脲、亚丙基脲或酒石酸二酰胺的N-乙烯基化合物,例如N,N’-二乙烯基亚乙基脲或N,N’-二乙烯基亚丙基脲。
其它合适的交联剂是二乙烯基二烷、四烯丙基硅烷或四乙烯基硅烷。
当然还可以使用上述化合物的混合物。优选使用溶于单体溶液或分散体中的那些交联剂。
特别优选的交联剂例如是亚甲基二丙烯酰胺,三烯丙基胺和三烯丙基烷基铵盐,二乙烯基咪唑,季戊四醇三烯丙基醚,N,N’-二乙烯基亚乙基脲,多元醇与丙烯酸或甲基丙烯酸的反应产物,聚氧化烯或已经与氧化乙烯和/或氧化丙烯和/或表氯醇反应的多元醇的甲基丙烯酸酯和丙烯酸酯。
非常特别优选的交联剂是季戊四醇三烯丙基醚、亚甲基双丙烯酰胺、N,N’-二乙烯基亚乙基脲、三烯丙基胺和三烯丙基单烷基铵盐,以及乙二醇、丁二醇、三羟甲基丙烷或甘油的丙烯酸酯,或已经与氧化乙烯和/或表氯醇反应的乙二醇、丁二醇、三羟甲基丙烷或甘油的丙烯酸酯。
基于单体A、B和C的总用量,交联剂的通常用量为0.01-5重量%。
后处理
如果通过在水中的溶液聚合方法得到聚合物,那么通常不必分离溶剂。然而,如果需要分离聚合物,则例如可以进行喷雾干燥。
如果通过在蒸汽-挥发性溶剂或溶剂混合物中的溶液聚合、沉淀聚合或悬浮聚合方法制备聚合物,那么可以通过引入蒸汽来分离该溶剂,从而得到水溶液或水分散体。还可以通过干燥工艺从有机稀释剂中分离聚合物。
在优选的实施方案中,本发明的聚合物是水溶性的或水分散性的。
对于本发明而言,水溶性单体和聚合物应当理解为表示在1升水中的溶解量为至少1g的单体和聚合物。
水分散性单体和聚合物应当理解为表示在施加剪切力(例如通过搅拌)的条件下分裂成分散性颗粒的单体和聚合物。亲水单体优选是水溶性的或至少是水分散性的。本发明聚合物通常是可分散于或可溶于水介质中的。
优选聚合物是固体含量优选为10-80重量%的水溶液或水分散体形式。聚合物的K值优选为20-120。
聚合物可以以如聚合过程中制得的溶解形式或固体形式提供给化妆品制剂,所述固体形式的聚合物可以通过干燥如聚合物溶液或分散体的喷雾干燥而得到。优选将聚合物以液体形式,即溶解、乳化或悬浮的形式,例如特别是以聚合物水溶液的形式用于生产化妆品制剂。
在化妆品制剂中的使用
上述聚合物特别适合制备化妆品组合物和皮肤用组合物。因此本发明进一步提供了本发明聚合物在化妆品组合物或皮肤用组合物中的用途。
本发明进一步提供了含有下列单体结构单元的聚合物在化妆品或皮肤制剂中的用途:
a)至少一种上述的具有通式I的二烯丙基胺(单体A),
b)一种或多种上述的烯属不饱和单体B和/或C,和
c)如果合适的话,至少一种交联剂。
本发明的聚合物例如在用于人体护理的制剂中用作聚合物膜形成剂,这涉及在角质表面如皮肤、头发、指甲的化妆品制剂中的应用以及在嘴部护理制剂中的应用。它们可以广泛地用于或配制到各种化妆品制剂中,并且与常用组分相容。本发明分散体的特征尤其在于优异的调理剂性能。
本发明因此进一步提供了包含下列物质的化妆品组合物或皮肤用组合物:
-至少一种本发明聚合物和
-至少一种化妆品或皮肤可接受的载体。
此外,在这些化妆品组合物中,单体C可以代替单体B而作为结构单元存在于聚合物中。
本发明的组合物具有化妆品或皮肤可接受的优选选自如下的载体:
1)水
2)与水混溶的有机溶剂,优选C1-C4链烷醇,
3)油、脂肪、蜡,
4)不同于3)的C6-C30单羧酸与一元、二元或三元醇的酯,
5)饱和的无环和环状烃,
6)脂肪酸,
7)脂肪醇,
8)硅油,
及其混合物。
本发明组合物例如具有例如选自如下的油或脂肪组分:
-低极性的烃如矿物油,
-线性饱和烃,优选具有多于8个碳原子的线性饱和烃,例如十四烷、十六烷、十八烷等,
-环烃,例如十氢化萘,
-支化烃,
-动物和植物油,
-蜡和蜡酯,
-凡士林,
-酯,优选脂肪酸酯,例如C1-C24一元醇与C1-C22单羧酸的酯,例如异硬脂酸异丙基酯、十四烷酸正丙酯、十四烷酸异丙酯、十六烷酸正丙酯、十六烷酸异丙酯、十六烷酸二十六烷基酯、十六烷酸二十八烷基酯、十六烷酸三十烷基酯、十六烷酸三十二烷基酯、十六烷酸三十四烷基酯、硬脂酸二十六烷基酯、硬脂酸二十八烷基酯、硬脂酸三十烷基酯、硬脂酸三十二烷基酯、硬脂酸三十四烷基酯,
-水杨酸酯,例如水杨酸C1-C10烷基酯如水杨酸辛酯;苯甲酸酯,例如苯甲酸C10-C15烷基酯、苯甲酸苄酯,
-其它化妆品用酯,例如甘油三脂肪酸酯、丙二醇单月桂酸酯、聚乙二醇单月桂酸酯、乳酸C10-C15烷基酯等,及其混合物。
其它优选的油和脂肪组分选自石蜡和石蜡油,天然脂肪和油,例如蓖麻油、豆油、花生油、橄榄油、向日葵油、芝麻油、鳄梨油、可可脂、杏仁油、桃仁油、蓖麻油(ricinus oil)、鱼肝油、猪油、鲸蜡、鲸蜡油、鲸油、麦胚油、澳洲坚果油、月见草油、霍霍巴油;脂肪醇,例如月桂醇、十四烷醇、十六烷醇、十八烷醇、油醇、十六烷醇;脂肪酸,例如十四烷酸、十八烷酸、十六烷酸、油酸、亚油酸、亚麻酸,以及不同于它们的饱和、不饱和和取代的脂肪酸;蜡,例如蜂蜡、棕榈蜡、小烛树蜡、鲸蜡,以及上述油或脂肪组分的混合物。
合适的硅油例如是线性聚二甲基硅氧烷,聚甲基苯基硅氧烷,环状硅氧烷,以及在室温下可以是液体或树脂形式的氨基、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,及其混合物。聚二甲基硅氧烷和聚甲基苯基硅氧烷的数均分子量优选为约1 000-150 000g/mol。优选的环状硅氧烷具有4-8元环。合适的环状硅氧烷是例如以商品名环状聚二甲基硅氧烷市售。
合适的化妆品和皮肤相容的油和脂肪组分描述于Karl-HeinzSchrader,Grundlagen und Rezepturen der Kosmetika(化妆品基本材料和配方),第2版,Verlag Hüthig,Heidelberg,第319-355页中,该文献在此引入作为参考。
特别合适的亲水载体选自水,优选具有1-8个碳原子的一元醇、二元醇或多元醇,例如乙醇、正丙醇、异丙醇、丙二醇、甘油、山梨糖醇等。
本发明的化妆品组合物可以是皮肤化妆品组合物、发用化妆品组合物、皮肤用组合物、卫生组合物或药物组合物。由于其成膜性能,上述聚合物特别适合作为头发和皮肤化妆品的添加剂,非常特别优选作为发用化妆品制剂的添加剂。
本发明的组合物优选以凝胶、泡沫、喷雾剂、软膏、霜剂、乳液、悬浮液、洗液、奶液剂或糊剂的形式。如果需要,还可使用脂质体或微球体。
本发明的化妆品或皮肤活性组合物可以另外含有化妆品和/或皮肤活性成分以及助剂。
优选本发明的化妆品组合物含有至少一种本发明聚合物,至少一种如上定义的载体和至少一种不同于该聚合物的组分,该组分选自化妆品活性成分、乳化剂、表面活性剂、防腐剂、芳香油、增稠剂、发用聚合物、头发和皮肤调理剂、接枝聚合物、水溶性或水分散性的含聚硅氧烷的聚合物、光保护剂、漂白剂、凝胶形成剂、护理剂、着色剂、调色剂、晒黑剂、染料、颜料、基础剂、湿润剂、再加脂剂、胶原蛋白、蛋白质水解物、类脂、抗氧化剂、防沫剂、抗静电剂、柔润剂和软化剂。
如果合适,化妆品制剂可以含有芳香油。可以提到的芳香油例如是天然和合成香料的混合物。
天然香料是来自如下对象的提取物:花(百合、熏衣草、玫瑰、茉莉、橙花、依兰香),茎和叶(天竺葵、广藿香、苦橙叶),果实(茴香子、芫荽、伞花茴香、杜松),果皮(香柠檬、柠檬、橙),根(肉豆蔻、当归、芹、小豆蔻、闭鞘姜、鸢尾、石菖蒲),木材(松木、檀香木、愈创木、柏木、玫瑰木),草(狭叶青蒿、香茅草、鼠尾草、百里香),针叶和树枝(云杉、冷杉、松树、矮松),树脂和香树胶(白松香、榄香脂、安息香、没药、乳香、愈创草)。
还合适的是动物原料,例如灵猫香和海狸香。典型的合成香料化合物是酯、醚、醛、酮、醇和烃类产物。酯类香料化合物例如是乙酸苄酯、异丁酸苯氧乙酯、乙酸4-叔丁基环己酯、乙酸里哪酯、乙酸二甲基苄基甲酯、乙酸苯基乙酯、苯甲酸里哪酯、甲酸苄酯、甲基苯基氨基乙酸乙酯、环己基丙酸烯丙酯、丙酸苏合香酯和水杨酸苄酯。醚类例如包括苄基乙基醚。醛类例如包括具有8-18个碳原子的线性链烷醛、柠檬醛、香茅醛、香茅基含氧乙醛、仙客来醛、羟基香茅醛、铃兰醛和波洁洪醛(Bourgeonal)。酮类例如包括紫罗酮、cc-异甲基紫罗酮、柏木甲酮。醇类例如包括茴香脑、香茅醇、丁子香酚、异丁子香酚、香叶醇、里哪醇、苯乙醇和Terioneol。烃类主要包括萜和香脂。
然而优选使用不同香料的混合物,这些香料一起产生令人愉快的香味。大多数用作芳香组分的低挥发性的精油也适合作为芳香油,例如鼠尾草油、果香菊油、丁香油、蜜蜂花油、薄荷油、肉桂叶油、来檬花油、杜松子油、香根油、乳香油、白松香油、Labolanuml和杂熏衣草油。优选单独或以为混合物使用香柠檬油、二氢香叶烯醇、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、仙客来醛、里哪醇、BoisambreneForte、龙涎呋喃、吲哚、二氢茉莉酮酸甲酯、Sandelice、柠檬油、桔油、橙油、甘油烯丙基。戊基酯、Cyclovertal、杂熏衣草油、麝香葡萄酒味鼠尾草油、β-突厥酮、天竺葵油、波旁醛、水杨酸环己酯、VertofixCoeur、Iso-E-Super、FixolideNP、合成橡苔、Iraldein gamma、苯乙酸、乙酸香叶酯、乙酸苄酯、玫瑰醚、Romillat、Irotyl和Floramat。
常用增稠剂是交联聚丙烯酸及其衍生物,多糖如黄原胶、琼脂、藻酸盐或甲基纤维素,纤维素衍生物如羧甲基纤维素或羟基羧甲基纤维素,脂肪醇,单酸甘油酯和脂肪酸,聚乙烯醇和聚乙烯基吡咯烷酮。合适的增稠剂还可以是得自Rohm & Haas的Aculyn级产品,例如Aculyn22(丙烯酸酯和具有硬脂基的甲基丙烯酸乙氧基化物的共聚物(20 EO单元))和Aculyn28(丙烯酸酯和具有二十二烷基的甲基丙烯酸乙氧基化物的共聚物(20 EO单元))。
合适的化妆品和/或皮肤活性组分例如是着色活性组分、皮肤和头发的着色剂、调色剂、晒黑剂、漂白剂、硬化角蛋白的物质、抗菌活性成分、滤光活性成分、驱虫活性成分、具有充血作用的物质、具有角质层分离和角膜成形作用的物质、去头屑活性成分、消炎剂、具有角化作用的物质、具有抗氧化作用或自由基清除作用的活性成分、润湿皮肤或保湿的物质、加脂活性成分、抗红斑或抗过敏活性成分,及其混合物。
人工晒黑皮肤并且适于无须自然或人工辐射紫外线而晒黑皮肤的活性成分例如是二羟基丙酮、阿脲和胡桃壳提取物。
合适的硬化角蛋白的物质通常是也适合用于止汗的活性物质,例如硫酸铝钾、羟基氯化铝、乳酸铝等。
抗菌活性成分用于破坏微生物或抑制其生长,并因此同时用作防腐剂和防止体臭形成或加强的除臭物质。这些物质例如包括常用防腐剂,例如对羟基苯甲酸酯、咪唑烷基脲、甲醛、山梨酸、苯甲酸、水杨酸等。该除臭物质例如是蓖麻醇酸锌、三氯生(Triclosan)、十一碳烯酸烷基醇酰胺、柠檬酸三乙酯、洗必太等。
合适的滤光活性成分是在UV-B和/或UV-A区吸收UV光线的物质。合适的UV滤光剂例如是2,4,6-三芳基-1,3,5-三嗪,其中在每种情况下芳基可以带有至少一个优选选自羟基、烷氧基(具体是甲氧基)、烷氧羰基(具体是甲氧羰基和乙氧羰基)及其混合基团的取代基。也合适的是对氨基苯甲酸酯、肉桂酸酯、二苯甲酮、樟脑衍生物,以及阻挡UV光线的颜料如二氧化钛、滑石和氧化锌。
合适的驱虫活性组分是能够驱赶或使特定动物(特别是昆虫)远离人类的化合物。这些化合物例如包括2-乙基-1,3-己二醇、N,N-二乙基-间甲苯酰胺等。促进血液流过皮肤的具有充血作用的合适物质例如是精油如矮松、熏衣草、迷迭香、杜松子、烤栗提取物、桦树叶提取物、干草种子提取物、乙酸乙酯、樟脑、薄荷醇、薄荷油、迷迭香提取物、桉油等。
合适的角质层分离和角膜成形物质例如为水杨酸、巯基乙醇酸钙、巯基乙酸及其盐、硫等。合适的去头屑活性组分例如是硫、硫化聚乙二醇脱水山梨糖醇单油酸酯、硫化蓖麻醇聚乙氧基化物(Schwefelricinolpolyethoxylat)、2-巯基吡啶氧化锌、2-巯基吡啶氧化铝等。
抵抗皮肤刺激的合适消炎剂例如为尿囊素、红没药醇、α-红没药醇(Dragosantol)、甘菊提取物、泛醇等。
在化妆品和皮肤制剂中使用的光保护性滤光剂具有防止阳光对人类皮肤的有害作用或至少减轻其后果的任务。此外,这些光保护性滤光剂还用于保护其它成分以抵抗UV辐射产生的分解或降解。在发用化妆品制剂中,应当减轻UV光线对角蛋白纤维的损害。
为了抵抗UV-B辐射,已知许多化合物,其中尤其是3-亚苄基樟脑、4-氨基苯甲酸、肉桂酸、水杨酸、二苯甲酮和2-苯基苯并咪唑的衍生物。
可以使用的UV光保护性滤光剂是油溶性有机UV-A滤光剂和/或UV-B滤光剂和/或水溶性有机UV-A滤光剂和/或UV-B滤光剂。基于制剂的总重量,UV光保护性滤光剂的总用量通常是0.1-30重量%,优选0.5-15重量%,特别是1-10重量%。
有利地选择UV光保护性滤光剂以使该制剂保护皮肤以抵抗整个范围的紫外光辐射。
UV光保护性滤光剂的实例是:
4-氨基苯甲酸
3-(4’-三甲基铵)亚苄基-2-莰酮甲基硫酸酯
水杨酸3,3,5-三甲基环己基酯(水杨酸高
酯)
2-羟基-4-甲氧基二苯甲酮
2-苯基苯并咪唑-5-磺酸及其钾盐、钠盐和三乙醇胺盐
3,3’-(1,4-亚苯基二次甲基)双(7,7-二甲基-2-氧代带双环[2.2.1]庚烷-1-甲磺酸)及其盐
4-双(聚乙氧基)氨基苯甲酸聚乙氧基乙酯
4-二甲基氨基苯甲酸2-乙基己酯
水杨酸2-乙基己酯
4-甲氧基肉桂酸2-异戊酯
4-甲氧基肉桂酸2-乙基己酯
2-羟基-4-甲氧基二苯甲酮-5-磺酸及其钠盐
3-(4’-磺基)亚苄基-2-莰酮及其盐
3-亚苄基-2-莰酮
1-(4’-异丙基苯基)-3-苯基-1,3-丙二酮
水杨酸4-异丙基苄酯
2,4,6-三苯胺基-(邻-羰基-2’-乙基己基-1’-氧基)-1,3,5-三嗪(2,4,6-Trianilino-(o-carbo-2’-ethylhexyl-1’-oxy)-1,3,5-triazin)
3-咪唑-4-基丙烯酸及其乙酯
对-氨基苯甲酸甘油酯或:4-氨基苯甲酸1-甘油酯
2,2’-二羟基-4-甲氧基二苯甲酮
2-羟基-4-甲氧基-4-甲基二苯甲酮(美可西酮)
三乙醇胺水杨酸酯
二甲氧基苯基乙醛酸或:3,4-二甲氧基苯基乙醛酸钠
3-(4’-磺基)亚苄基-2-莰酮及其盐
2,2’,4,4’-四羟基二苯甲酮
2,2’-亚甲基双[6(2H-苯并三唑-2-基)-4-(1,1,3,3,-四甲基丁基)苯酚]
2,2’-(1,4-亚苯基)双-1H-苯并咪唑-4,6-二磺酸及其钠盐
2,4-双[4-(2-乙基己氧基)-2-羟基]苯基-6-(4-甲氧基苯基)-(1,3,5)-三嗪
3-(4-甲基亚苄基)樟脑
4-双(聚乙氧基)对氨基苯甲酸聚乙氧基乙酯
2,4-二羟基二苯甲酮
2,2’-二羟基-4,4’-二甲氧基二苯甲酮-5,5’-磺酸二钠
合适的基础剂主要是具有12-22个,优选16-18个碳原子的脂肪醇或羟基脂肪醇以及偏甘油酯、脂肪酸或羟基脂肪酸。优选这些物质与低聚烷基葡糖苷和/或具有相同链长的脂肪酸N-甲基葡糖酰胺和/或聚12-羟基硬脂酸聚甘油酯的组合。合适的增稠剂例如是多糖,特别是黄原胶、瓜耳胶、琼脂、藻酸盐和甲基纤维素、羧甲基纤维素和羟乙基纤维素,以及更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CarbopolTM或来自Sigma的SynthalenTM),聚丙烯酰胺,聚乙烯醇和聚乙烯基吡咯烷酮,表面活性剂例如乙氧基化的脂肪酸甘油酯,脂肪酸与多元醇(例如季戊四醇或三羟甲基丙烷)的酯,具有窄的同系物分布的脂肪醇乙氧基化物或低聚烷基葡糖苷,以及电解质如氯化钠和氯化铵。
可以使用的富脂剂例如是羊毛脂和卵磷脂,以及聚乙氧基化或酰基化的羊毛脂和卵磷脂衍生物,多元醇脂肪酸脂,单甘油酯和脂肪酸链烷醇酰胺,后者还用作泡沫稳定剂。
抗氧化剂通常是本身已知的化合物。抗氧化剂有利地选自下组: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,氯原酸及其衍生物,硫辛酸及其衍生物(例如二氢硫辛酸),以及(金属)螯合剂、EDTA、EGTA及其衍生物,泛醌和泛醌醇及其衍生物,维生素C及其衍生物(例如十六烷酸抗坏血酸酯、磷酸抗坏血酸酯镁盐、乙酸抗坏血酸酯),生育酚及其衍生物(例如维生素E乙酸酯),维生素A及其衍生物(维生素A十六烷酸酯),丁基羟基甲苯,丁基羟基苯甲醚,以及其它在化妆品制剂中常用的抗氧化剂。
上述抗氧化剂在最终制剂中的用量例如是0.001-30重量%,优选0.01-10重量%,特别是1-5重量%。
此外,还可以使用抗菌添加剂。这些通常包括所有对革兰士阳性细菌具有特异性作用的合适防腐剂,例如三氯生(2,4,4’-三氯-2’-羟基二苯醚),氯己定(1,1’-六亚甲基双[5-(4-氯苯基)双胍])和TTC(3,4,4’-三氯-N-碳酰苯胺)。
季铵化合物原则上同样合适,但优选用于灭菌皂和洗液。
许多香料还具有抗菌性质。将对革兰士阳性细菌具有特异性效果的特定组合用于所谓的除臭芳香剂组合物中。
许多精油或其特性组分,例如丁香油(丁子香酚)、薄荷油(薄荷醇)或百里香油(百里酚)也表现出优异的抗菌效果。
抗菌有效物质通常以该制剂的约0.1-0.3重量%浓度使用。
合适的珠光蜡例如是:亚烷基二醇酯,具体是二硬脂酸乙二醇酯;脂肪酸链烷醇酰胺,具体是椰子油脂肪酸二乙醇酰胺;偏甘油酯,具体是硬脂酸单甘油酯;任选羟基取代的多元羧酸与具有6-22个碳原子的脂肪醇的酯,具体是酒石酸的长链酯;共计具有至少24个碳原子的脂肪物质例如脂肪醇、脂肪酮、脂肪醛、脂肪醚和脂肪碳酸酯,具体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,以及它们的混合物。
其它聚合物
本发明化妆品组合物可以含有至少一种化妆品或皮肤可接受的不同于本发明聚合物的其它聚合物以建立所需的组合物性质。适合该目的的通常非常概括的是阴离子、阳离子、两性和中性聚合物。
阴离子聚合物例如是丙烯酸和甲基丙烯酸或其盐的均聚物和共聚物,丙烯酸和丙烯酰胺和其盐的共聚物;聚羟基羧酸的钠盐、水溶性或水分散性聚酯、聚氨酯如得自BASF的Luviset PUR以及聚脲。特别合适的聚合物是丙烯酸叔丁酯、丙烯酸乙酯、甲基丙烯酸的共聚物(例如Luvimer100P);丙烯酸乙酯和甲基丙烯酸的共聚物(例如LuviflexSoft和LuvimerMAE);N-叔丁基丙烯酰胺、丙烯酸乙酯、丙烯酸的共聚物(Ultrahold8,强);乙酸乙烯酯、巴豆酸和合适的话还有其它乙烯基酯的共聚物(例如Luviset品级,INCI:VA/巴豆酸酯的共聚物);任选与醇、阴离子聚硅氧烷(如羧基官能化的)、丙烯酸叔丁酯、甲基丙烯酸反应的马来酸酐共聚物(例如LuviskolVBM);丙烯酸和甲基丙烯酸与疏水单体的共聚物,该疏水单体例如是甲基丙烯酸C4-C30烷基酯、C4-C30烷基乙烯基酯、C4-C30烷基乙烯基醚和透明质酸。阴离子聚合物的实例还可以是乙酸乙烯酯/巴豆酸共聚物,例如以Resyn(National Starch)和Gafset(GAF)市售,以及乙烯基吡咯烷酮/丙烯酸乙烯酯共聚物,例如以商品名Luviflex(BASF)市售。其它合适的聚合物是以商品名LuviflexVBM-35(BASF)市售的乙烯基吡咯烷酮/丙烯酸酯三元共聚物,以及含磺酸钠的聚酰胺或含磺酸钠的聚酯。
此外,适合与本发明聚合物结合使用的聚合物是例如BalanceCR(National Starch;丙烯酸酯共聚物)、Balance0/55(National Starch;丙烯酸酯共聚物)、Balance47(National Starch;辛基丙烯酰胺/丙烯酸酯/甲基丙烯酸丁基氨基乙酯共聚物)、AquaflexFX 64(ISP:异丁烯/乙基马来酰亚胺/羟乙基马来酰亚胺共聚物)、AquaflexSF-40(ISP/NationalStarch;VP/乙烯基己内酰胺/DMAPA丙烯酸酯共聚物)、AllianzLT-120(ISP/Rohm&Haas;丙烯酸酯/C1-2琥珀酸酯/羟基丙烯酸酯共聚物)、AquarezHS(Eastman;聚酯-1)、DiaformerZ-400(Clariant;甲基丙烯酰基乙基甜菜碱/甲基丙烯酸酯共聚物)、DiaformerZ-711(Clariant;甲基丙烯酰基乙基N-氧化物/甲基丙烯酸酯共聚物)、DiaformerZ-712(Clariant;甲基丙烯酰基乙基N-氧化物/甲基丙烯酸酯共聚物)、Omnirez2000(ISP;在乙醇中的聚(甲基乙烯基醚/马来酸)的单乙酯)、AmphomerHC(National Starch;丙烯酸酯/辛基丙烯酰胺共聚物)、Amphomer28-4910(National Starch;辛基丙烯酰胺/丙烯酸酯/甲基丙烯酸丁基氨基乙酯共聚物)、AdvantageHC 37(ISP;乙烯基己内酰胺/乙烯基吡咯烷酮/甲基丙烯酸二甲氨基乙酯的三元共聚物)、AdvantageLC55和LC80或LC A和LC E、AdvantagePlus(ISP;VA/马来酸丁酯/丙烯酸异冰片酯共聚物)、Aculyne258(Rohm&Haas;丙烯酸酯/羟基酯丙烯酸酯共聚物)、LuvisetP.U.R.(BASF;聚氨酯-1),LuviflexSilk(BASF)、EastmanAQ 48(Eastman)、StylezeCC-10(ISP;VP/DMAPA丙烯酸酯共聚物)、Styleze2000(ISP;VP/丙烯酸酯/甲基丙烯酸月桂酯共聚物)、Dynam X(National Starch;聚氨酯-14 AMP丙烯酸酯共聚物)、ResynXP(National Starch;丙烯酸酯/辛基丙烯酰胺共聚物)、Fixomer A-30(OndeoNalco;聚甲基丙烯酸(和)丙烯酰胺基甲基丙磺酸)、Fixate G-100(Noveon;AMP丙烯酸酯/甲基丙烯酸烯丙酯共聚物)。
其它合适的聚合物是INCI名称为聚季铵盐(Polyquaternium)的阳离子聚合物,例如,乙烯基吡咯烷酮/N-乙烯基咪唑盐的共聚物(LuviquatFC、LuviquatHM、LuviquatMS、LuviquatUltracare),用硫酸二乙酯季铵化的N-乙烯基吡咯烷酮/甲基丙烯酸二甲氨基乙酯的共聚物(LuviquatPQ 11,INCI:聚季铵盐-11)、N-乙烯基己内酰胺/N-乙烯基吡咯烷酮/N-乙烯基咪唑盐的共聚物(LuviquatHold,INCI:聚季铵盐-46);阳离子纤维素衍生物(聚季铵盐-4和-10)、丙烯酰胺基共聚物(聚季铵盐-7),脱乙酰壳多糖,阳离子淀粉衍生物(INCI:淀粉羟丙基三甲基氯化铵,改性玉米淀粉),阳离子瓜耳胶衍生物(INCI:羟丙基瓜耳羟丙基三甲基氯化铵),阳离子向日葵油衍生物(INCI:向日葵籽酰胺基丙基羟乙基二甲基氯化铵),丙烯酸、丙烯酰胺和甲基丙烯酰胺基丙基三甲基氯化铵的共聚物(INCI:聚季铵盐-53),聚季铵盐-32,聚季铵盐-28及其它。合适的阳离子(季铵化)聚合物还可以是Merquat(基于二甲基二烯丙基氯化铵的聚合物)、Gafquat(由聚乙烯基吡咯烷酮与季铵化合物反应形成的季铵聚合物)、聚合物JR(具有阳离子基团的羟乙基纤维素)和基于植物的阳离子聚合物,例如瓜尔胶聚合物如得自Rhodia的Jaguar品级产品。
其它合适的聚合物还可以是中性聚合物,例如聚乙烯基吡咯烷酮,N-乙烯基吡咯烷酮和乙酸乙烯酯和/或丙酸乙烯酯的共聚物,聚硅氧烷,聚乙烯基己内酰胺,以及含有N-乙烯基吡咯烷酮的其它共聚物,N-乙烯基吡咯烷酮与烷基链长为C1-C18的丙烯酸烷基酯或甲基丙烯酸烷基酯单体的共聚物,将聚乙烯基醇接枝到聚亚烷基二醇上的接枝共聚物,例如KollicoatIR(BASF),将其它乙烯基单体接枝到聚亚烷基二醇上的接枝共聚物,聚硅氧烷,聚乙烯基己内酰胺及其与N-乙烯基吡咯烷酮的共聚物,聚乙烯亚胺及其盐,聚乙烯胺及其盐,纤维素衍生物,脱乙酰壳多糖,聚天冬氨酸盐及其衍生物,聚乙烯亚胺及其盐,聚乙烯胺及其盐,纤维素衍生物,聚天冬氨酸盐及其衍生物。这些包括,例如LuviflexSwing(聚乙酸乙烯酯和聚乙二醇的部分皂化共聚物,BASF)。
合适的聚合物还可以是非离子、水溶性或水分散性聚合物或低聚物,例如聚乙烯基己内酰胺,如LuviskolPlus(BASF)或聚乙烯基吡咯烷酮及其共聚物,特别是与乙烯基酯如乙酸乙烯酯的共聚物,例如LuviskolVA37(BASF);聚酰胺,例如基于衣康酸和脂族二胺的聚酰胺,例如DE-A-4333 238所述。
合适的聚合物还可以是两性聚合物或两性离子聚合物,例如辛基丙烯酰胺/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-羟丙酯共聚物,以商品名Amphomer(National Starch)市售,以及两性离子聚合物,例如公开于DE-A 39 29 973、DE-A 21 50 557、DE-A 28 17 369和DE-A 3708 451中。丙烯酰胺基丙基三甲基氯化铵/丙烯酸或甲基丙烯酸共聚物及其碱金属盐和铵盐是优选的两性离子聚合物。其它合适的两性离子聚合物是以商品名Amersette(AMERCHOL)市售的甲基丙烯酰基乙基甜菜碱/甲基丙烯酸酯共聚物,以及甲基丙烯酸羟乙酯、甲基丙烯酸甲酯、甲基丙烯酸N,N-二甲氨基乙酯和丙烯酸的共聚物(Jordapon)。
合适的聚合物还可以是非离子的含硅氧烷的水溶性或水分散性聚合物,例如聚醚硅氧烷,如Tegopren(Goldschmidt)或Belsil(Wacker)。
药物组合物
还可以将本发明的药物上可接受的聚合物有利地用于药物组合物的制备中。药物上可接受的助剂是已知用于药物、食品技术和相关领域的那些,特别是相关药典(例如DAB Ph.Eur.BP NF)中列出的那些,以及其性质不排除生理学应用的其它助剂。
合适的助剂可以是润滑剂,润湿剂,乳化剂和悬浮剂,防腐剂,抗氧化剂,抗刺激性物质,螯合剂,乳液稳定剂,成膜剂,胶凝剂,气味掩蔽剂,树脂,亲水胶体,溶剂,增溶剂,中和剂,渗透促进剂,颜料,季铵化合物,加脂剂和富脂剂,软膏基质、霜剂基质或油基质物质,聚硅氧烷衍生物,稳定剂,杀菌剂,驱虫剂,干燥剂,遮光剂,增稠剂,蜡,柔润剂,白油成分。这方面的制剂基于例如在Fiedler,H.P.Lexikon derHilfsstoffe für Pharmazie,Kosmetik und angrenzende Gebiete(药物、化妆品及相关领域的助剂词汇手册),第4版,Aulendorf:ECV-Editio-Kantor-Verlag,1996中给出的专业知识。
为制备本发明的皮肤用组合物,活性成分可以与合适的助剂(赋形剂)混合或用合适的助剂(赋形剂)稀释。赋形剂可以是可以用作活性成分的媒介、载体或介质的固体、半固体或液体物质。如果需要,以本领域技术人员已知的方式混合其它助剂。此外,该聚合物适合作为药物中的助剂,优选用作固体药物剂型的涂层或粘结剂或用于固体药物剂型的涂层或粘结剂中。还可以将其用于霜剂以及作为片剂涂层和片剂粘结剂。
皮肤清洁组合物
在进一步优选的实施方案中,将本发明的聚合物用于皮肤清洁制剂中。
优选的皮肤清洁组合物为液体至凝胶状稠度的皂,例如透明皂、高级香皂、除臭皂、霜剂皂、小儿皂、护肤皂、擦洗皂和合成洗涤剂、膏状皂、软皂和洗浴糊、液体皂、淋浴和盆浴用制剂,如洗液、淋浴浴液和淋浴凝胶、泡沫浴液、浴油和擦洗制剂,剃须泡沫、洗液和霜剂。
头发处理组合物
根据特别优选的实施方案,本发明组合物是头发处理组合物。
本发明头发处理组合物优选含有至少一种本发明聚合物,基于组合物的总重量,其用量为约0.1-30重量%,优选0.5-20重量%。
本发明头发处理组合物优选为定型泡沫、发用摩丝、发用凝胶、洗发剂、喷发胶、发用泡沫剂、最终处理液(Spitzenfluids)、长效卷发剂的中和剂、染发剂和漂白剂或热油处理剂的形式。根据应用领域,发用化妆品制剂可以以(气溶胶)喷雾剂、(气溶胶)泡沫剂、凝胶、凝胶喷雾剂、霜剂、乳液或蜡的形式使用。喷发胶包括气溶胶型喷雾剂和没有推进剂气体的泵式喷雾剂。发用泡沫剂包括气溶胶泡沫剂和没有推进剂气体的泵式泡沫剂。喷发胶和发用泡沫剂优选主要包括或仅包含水溶性或水分散性组分。如果在本发明的喷发胶和发用泡沫剂中使用的化合物是水分散性组分。如果在本发明的喷发胶和发用泡沫剂中使用的化合物是水分散性的,那么可以将其以粒径通常为1-350纳米,优选1-250纳米的水微分散体形式使用。在此,这些制剂的固体含量通常为约0.5-20重量%。这些微分散体通常不需要乳化剂或表面活性剂进行稳定。
在一个优选实施方案中,本发明的发用化妆品制剂含有:
I.0.05-20重量%的至少一种本发明聚合物,
II.20-99.95重量%的水和/或醇,
III.0-79.5重量%的其它组分。
醇应当理解为表示常用于化妆品中的所有醇,例如乙醇、异丙醇、正丙醇。
其它组分应当理解为表示常用于化妆品中的添加剂,其中一部分已经提到,例如推进剂,消泡剂,界面活性化合物(即表面活性剂、乳化剂),发泡剂和增溶剂。使用的界面活性化合物可以是阴离子、阳离子、两性或中性的。其它的常用组分例如可以是防腐剂、芳香油、遮光剂、活性组分、抗氧化剂、紫外线滤光剂、护理物质(例如泛醇、胶原蛋白、维生素、蛋白质水解物、α-和β-羟基羧酸、白质水解物)、稳定剂、pH调节剂、染料、粘度调节剂、胶凝剂、盐、湿润剂、再加脂剂、络合剂,以及其它常用添加剂。
这些还包括化妆品中已知的所有发型和调理聚合物,如果需要设定非常特定的性质,这些聚合物还可以与本发明的聚合物结合使用。
合适的常规发用化妆品聚合物例如是上述阳离子、阴离子、中性、非离子和两性聚合物,在此引入本文作为参考。
为设定某种性质,该制剂还可以另外含有基于聚硅氧烷化合物的调理物质。合适的聚硅氧烷化合物例如是聚烷基硅氧烷、聚芳基硅氧烷、聚芳基烷基硅氧烷、聚醚硅氧烷、聚硅氧烷树脂或含聚氧乙烯或聚氧丙烯侧链的聚二甲基硅氧烷(CTFA)和氨基官能化的聚硅氧烷化合物如氨基封端的聚二甲基硅氧烷(CTFA),“GP4 Silicone Fluid”和“GP 7100”(Genesee),“Q2 8220”(Dow Corning),“AFL 40”(Union Carbide),或者在EP-B852 488,第4页第一行至第6页第16行中公开的聚合物,该文献在此完全引入作为参考。
其它合适的混合组分是具有如下聚合物主链和侧链的聚硅氧烷接枝聚合物:含有聚硅氧烷的聚合物主链和含有非聚硅氧烷的侧链,或者含有非聚硅氧烷的聚合物主链和含有聚硅氧烷的侧链,或者含有聚硅氧烷的聚合物主链和含有聚硅氧烷的侧链。该聚合物的实例是LuviflexSilk(BASF)或者在EP-B 852 488,第3页第20-58行中的那些。
此外,在化妆品制剂中聚硅氧烷橡胶也适合作为本发明聚合物的混合组分。该聚硅氧烷橡胶公开于EP-B 852488,第6页第17行至第7页第6行中,该文献在此完全引入作为参考。
本发明聚合物特别适合在发型制剂中作为定型剂,特别是在喷发胶(包括气溶胶型喷雾剂和没有推进剂气体的泵式喷雾剂)和发用泡沫剂(包括气溶胶泡沫剂和没有推进剂气体的泵式泡沫剂)中。
在一个优选实施方案中,这些制剂含有:
a)0.1-10重量%的至少一种本发明聚合物,
b)20-99.9重量%的水和/或醇,
c)0-70重量%的至少一种推进剂,
d)0-20重量%的其它组分。
推进剂是喷发胶或气溶胶泡沫中常用的推进剂。优选丙烷/丁烷的混合物、戊烷、二甲醚、1,1-二氟乙烷(HFC-152 a)、二氧化碳、氮气或压缩空气。
本发明优选的气溶胶发用泡沫剂的制剂含有:
a)0.1-10重量%的至少一种本发明聚合物,
b)55-99.8重量%的水和/或醇,
c)5-20重量%的推进剂
d)0.1-5重量%的乳化剂,
e)0-10重量%的其它组分。
乳化剂
可以使用的乳化剂是发用泡沫剂中常用的所有乳化剂。合适的乳化剂可为非离子、阳离子、阴离子或两性的。
非离子乳化剂(INCI命名法)的实例为月桂醇氧乙烯醚类(Laureths),例如月桂基聚氧乙烯(4)醚;十六烷醇氧乙烯醚类(Ceteths),例如十六烷基乙二醇醚,聚乙二醇十六烷基醚;十六/十八醇氧乙烯醚类(Ceteareths),例如十六/十八醇氧乙烯(25)醚,聚乙二醇脂肪酸甘油酯、羟基化的卵磷脂、脂肪酸乳酸酯、烷基多苷。
阳离子乳化剂的实例是十六烷基二甲基2-羟乙基磷酸二氢铵、十六烷基三甲基氯化铵、十六烷基三甲基溴化铵、椰油基三甲基甲基硫酸铵、聚季铵盐-1至x(INCI)。
阴离子乳化剂例如可以选自烷基硫酸盐、烷基醚硫酸盐、烷基磺酸盐、烷基芳基磺酸盐、烷基琥珀酸盐、烷基磺基琥珀酸盐、N-烷酰基肌氨酸盐、酰基牛磺酸盐、酰基羟乙基磺酸盐、烷基磷酸盐、烷基醚磷酸盐、烷基醚羧酸盐、α-烯烃磺酸盐,特别是碱金属盐和碱土金属盐,例如钠、钾、镁、钙盐,以及铵盐和三乙醇铵盐。烷基醚硫酸盐、烷基醚磷酸盐和烷基醚羧酸盐可以在其分子中具有1-10个氧化乙烯或氧化丙烯单元,优选1-3个氧化乙烯单元。
优选的头发处理组合物为凝胶的形式。该头发处理组合物例如含有:
a)0.1-20重量%,优选1-10重量%的至少一种如上所定义的本发明聚合物,
b)0-40重量%的至少一种载体(溶剂),其选自C2-C5醇,特别是乙醇,
c)0.01-5重量%,优选0.2-3重量的至少一种增稠剂,
d)0-50重量%的推进剂,
e)0-10重量%,优选0.1-3重量%的至少一种不同于a)的定型聚合物,优选水容性非离子聚合物,
f)0-1重量%的至少一种再加脂剂,其优选选自甘油和甘油衍生物,
g)0-30重量%的其它活性组分和/或助剂,例如至少一种聚硅氧烷化合物,
h)补足100重量%的水。
适用于定型凝胶的本发明制剂例如可以具有下列组成:
a)0.1-10重量%的至少一种本发明聚合物,
b)60-99.85重量%的水和/或醇,
c)0.05-10重量%的胶凝剂,
d)0-20重量%的其它组分。
可以使用的胶凝剂是化妆品中常用的所有胶凝剂。这些胶凝剂包括轻度交联的聚丙烯酸,例如卡波姆(Carbomer)(INCI),纤维素衍生物,例如羟丙基纤维素、羟乙基纤维素、阳离子改性的纤维素、多糖如黄原胶、甘油三辛酸/癸酸酯、丙烯酸钠共聚物、聚季铵盐-32(和)液状石蜡(ParaffinumLiquidum)(INCI)、丙烯酸钠共聚物(和)液状石蜡(和)十三烷基丙二醇聚氧乙烯(6)聚醚、丙烯酰胺基丙基三甲基氯化铵/丙烯酰胺共聚物、硬脂醇聚醚硬脂基聚氧乙烯(10)(Steareth-10)/烯丙基醚/丙烯酸酯共聚物、聚季铵盐-37(和)液状石蜡(和)十三烷基丙二醇聚氧乙烯(6)聚醚、聚季铵盐-37(和)丙二醇二癸酸酯二辛酸酯(和)十三烷基丙二醇聚氧乙烯(6)聚醚、聚季铵盐-7、聚季铵盐-44。
本发明聚合物可以在化妆品制剂中用作调理剂。
本发明聚合物优选可以在洗发剂制剂中用作定型剂和/或调理剂。优选的洗发剂制剂含有:
a)0.05-10重量%的至少一种本发明聚合物,
b)25-94.95重量%的水,
c)5-50重量%的表面活性剂,
d)0-5重量%的其它调理剂,
e)0-10重量%的其它化妆品组分。
洗发剂中常用的所有阴离子、中性、两性或阳离子表面活性剂可用于该洗发剂制剂中。
表面活性剂
合适的阴离子表面活性剂例如是烷基硫酸盐、烷基醚硫酸盐、烷基磺酸盐、烷基芳基磺酸盐、烷基琥珀酸盐、烷基磺基琥珀酸盐、N-烷酰基肌氨酸盐、酰基牛磺酸盐、酰基羟乙基磺酸盐、烷基磷酸盐、烷基醚磷酸盐、烷基醚羧酸盐、α-烯烃磺酸盐,特别是碱金属盐和碱土金属盐,例如钠、钾、镁、钙盐,以及铵盐和三乙醇铵盐。烷基醚硫酸盐、烷基醚磷酸盐和烷基醚羧酸盐可以在分子中具有1-10个氧化乙烯或氧化丙烯单元,优选1-3个氧化乙烯单元。
例如十二烷基硫酸钠、月桂基硫酸铵、月桂醚硫酸钠、月桂醚硫酸铵、月桂酰基肌氨酸钠、油基琥珀酸钠、月桂基磺基琥珀酸铵、十二烷基苯磺酸钠、十二烷基苯磺酸三乙醇铵盐是合适的。
合适的两性表面活性剂例如是烷基甜菜碱、烷基酰胺基丙基甜菜碱、烷基磺基甜菜碱、烷基甘氨酸盐、烷基羧基甘氨酸盐、烷基两性基乙酸盐(Alkylamphoacetate)或烷基两性基丙酸盐、烷基两性基二乙酸盐或烷基两性基二丙酸盐。
例如可以使用椰油基二甲基磺基丙基甜菜碱、月桂基甜菜碱、椰油酰胺基丙基甜菜碱或椰油两性基丙酸钠(Natriumcocamphopropionat)。
合适的非离子表面活性剂例如是在烷基链中具有6-20个碳原子的线性或支化脂族醇或烷基酚与氧化乙烯和/或氧化丙烯的反应产物。氧化烯的用量是每摩尔醇约6-60摩尔。烷基胺氧化物、单烷基或二烷基链烷醇酰胺、聚乙二醇的脂肪酸酯、烷基多苷或脱水山梨糖醇醚酯也是合适的。
此外,洗发剂制剂还可以含有常用的阳离子表面活性剂,例如季铵化合物,如十六烷基三甲基氯化铵或十六烷基三甲基溴化铵(INCI:十六烷基三甲基氯化铵或十六烷基三甲基溴化铵),羟乙基十六烷基磷酸二铵(INCI:聚季铵盐-44),LuviquatMono LS(INCI:椰油基三甲基甲基硫酸铵),聚(氧基-1,2-乙烷二基),((十八烷基次氮基)三-2,1-乙烷二基)三羟基磷酸酯(1∶1)(盐)(INCI:聚季铵盐-52)。
在洗发剂制剂中,常用的调理剂可以与本发明聚合物结合使用以获得特定效果。这些调理剂例如包括INCI名称为聚季铵盐的上述阳离子聚合物,特别是乙烯基吡咯烷酮/N-乙烯基咪唑盐的共聚物(LuviquatFC、LuviquatHM、LuviquatMS、LuviquatUltracare),用硫酸二乙酯季铵化的N-乙烯基吡咯烷酮/甲基丙烯酸二甲氨基乙酯的共聚物(LuviquatPQ 11),N-乙烯基己内酰胺/N-乙烯基吡咯烷酮/N-乙烯基咪唑盐的共聚物(LuviquatHold);阳离子纤维素衍生物(聚季铵盐-4和聚季铵盐-10)、丙烯酰胺共聚物(聚季铵盐-7)。还可使用蛋白质水解物,以及基于聚硅氧烷化合物的调理物质,例如聚烷基硅氧烷、聚芳基硅氧烷、聚芳基烷基硅氧烷、聚醚硅氧烷或聚硅氧烷树脂。其它合适的聚硅氧烷化合物是含聚氧乙烯或聚氧丙烯侧链的聚二甲基硅氧烷(CTFA)和氨基官能化的聚硅氧烷化合物,例如氨基封端的聚二甲基硅氧烷(CTFA)。此外,可以使用阳离子瓜尔胶衍生物,例如瓜尔胶羟丙基三甲基氯化铵(INCI)。
实施例
下列实施例用于更详细地说明本发明而不是限制本发明。
I.分析
测定重均分子量
通过凝胶渗透色谱法(GPC)使用水洗脱液测定重均分子量(Mw)。
GPC使用来自Agilent的装置组合(1100系列)进行,这些设备包括:
脱气装置 型号G 1322A
等度泵 型号G 1310A
自动进样或取样器 型号G 1313A
柱加热炉 型号G 1316A
参比模件 型号G 1323B
差式折光计 型号G 1362A
在聚合物溶于水中的情况下,使用的洗脱液是0.08摩尔/升在蒸馏水中的TRIS-缓冲液(三羟甲基氨基甲烷缓冲液)(pH=7)+0.15摩尔/升来自NaCl和HCl的氯离子。在分离柱组合中进行分离。使用具有GRAL BIO线性分离材料的来自PSS的编号787和788(每个是8×30毫米)的柱子。在23℃的柱子温度下的流通速率是0.8毫升/分钟。
使用来自PPS的分子量M为194-1 700 000摩尔/克的聚氧化乙烯标准进行校准。
测定K值
根据H.Fikentscher,Cellulose-Chemie,第13卷,58-64和71-74(1932)在水溶液中、在pH为7下、在25℃的温度下且共聚物钠盐的聚合物浓度为1重量%的条件下测定共聚物的钠盐水溶液的K值。
测定固体含量
将规定量的样品(约0.5-1克)称重到铝盘上(初始重量)。在IR灯(160伏特)下干燥样品30分钟。然后再次测定样品质量(最终重量)。如下计算固体百分含量(SC):
SC=最终重量×100/初始重量[重量%]
二烯丙基单体和共聚物的制备
单体反应性烷氧基化物的制备
实施例M1:二烯丙基胺+20EO(EO是氧化乙烯)
首先将2.471千克二烯丙基胺和0.126千克软化水引入配有冷却套、氧化物计量加入装置和内部温度计的20升钢制反应器中。将反应器简单抽空然后在25℃下使用氮气建立15.4巴的压力。50分钟以后,将系统减压到3巴并且加热到80℃。然后在80分钟内,计量加入1.120千克氧化乙烯以使压力维持在2.8-4.3巴之间且温度不超过95℃。在计量加入氧化乙烯以后,搅拌混合物120分钟然后冷却到50℃。从反应器中取出1.217千克。将0.1463千克45%的KOH水溶液加入剩余的物料中。将温度升高到103℃并且在小于10毫巴的压力下除去水。然后用氮气建立2巴的压力并且将混合物加热到122℃,并且在21小时内,以气体加入14.817千克氧化乙烯,在此过程中将压力维持在2-5.5巴且温度不超过135℃。在240分钟以后中断计量加料,在118℃下继续搅拌,在110分钟内计量加入剩余的氧化物并且在该温度下继续搅拌129分钟。将混合物冷却到80℃并且从反应器中取出10.36千克。产物的OH数为62.9毫克KOH/克。
实施例M2:二烯丙基胺+40EO
将取出实施例M1产物之后残余在反应器中的产物在同一个反应器中加热到86℃并且用氮气惰化并建立起2巴的压力。然后将该混合物加热到115℃,并且在240分钟内以气体加入6.964千克氧化乙烯以使温度不超过130℃且压力保持在2-5.8巴之间。当计量添加完成以后,在117℃下搅拌该混合物120分钟并且从反应器中卸出13.24千克的产物。产物的OH数为32.03毫克KOH/克。
实施例M3:二烯丙基胺+80EO
在实施例1中使用的反应器中用0.04464千克的45%浓度KOH水溶液处理根据实施例M1制备的3.574千克产物,并且类似于实施例2用10.105千克氧化乙烯进行反应。由此得到13.51千克的反应器产物,其OH数为24.13毫克KOH/克。
季铵化
实施例Q1
季铵化的二烯丙基胺+20EO
在60℃下熔融548.18克二烯丙基胺+20EO(实施例M1)。在1小时内,将67.10克硫酸二甲酯均匀滴加到该熔体中。当添加完成时,进一步在60℃下搅拌该混合物2.5小时以完成反应。
实施例Q2
季铵化的二烯丙基胺+40EO
在65℃下熔融260.00克二烯丙基胺+40EO(实施例M2)。在1小时内,将16.74克硫酸二甲酯均匀滴加到该熔体中。当添加完成时,进一步在65℃下搅拌该混合物2小时以完成反应。
制备共聚物
实施例P1
首先在温和的氮气流下将853克去离子水、80克N-乙烯基吡咯烷酮、40克50重量%浓度的季铵化的二烯丙基胺+20EO(实施例Q1)的水溶液和1.5克三烯丙基胺引入配有锚式搅拌器、温度计、氮气入口、回流冷凝器和滴液漏斗的2升玻璃反应器中。然后用6.2克20重量%浓度的硫酸将其调节到pH为6.8并且加热到65℃。
一旦达到所需的65℃温度,在3小时内加入1.5克引发剂(WakoV50)在60.5克水中的20克溶液。然后将混合物加热到70℃,并且再搅拌1小时,然后在1小时内加入剩余的引发剂溶液(42克)。最后将该混合物后聚合2小时的时间。
溶液的固体含量为约10%。
实施例P2
首先在温和的氮气流下引入856克去离子水、80克N-乙烯基吡咯烷酮、40克50重量%浓度的季铵化的二烯丙基胺+20EO(实施例Q1)的水溶液和0.75克三烯丙基胺。然后用19克5重量%浓度的硫酸将其调节到pH为6.8并且加热到65℃。
一旦达到所需的65℃温度,在3小时内加入1.5克引发剂(WakoV50)在60.5克水中的20克溶液。然后将混合物加热到70℃,并且再搅拌1小时,然后在1小时内加入剩余的引发剂溶液(42克)。最后将该混合物后聚合2小时的时间。
溶液的固体含量为约10%。
实施例P3
首先在温和的氮气流下引入846克去离子水、70克N-乙烯基吡咯烷酮、60克50重量%浓度的季铵化的二烯丙基胺+20EO(实施例Q1)的水溶液和0.75克三烯丙基胺。然后用19克5重量%浓度的硫酸将其调节到pH为6.8并且加热到65℃。
一旦达到所需的65℃温度,在3小时内加入1.5克引发剂(WakoV50)在60.5克水中的20克溶液。然后将混合物加热到70℃,并且再搅拌1小时,然后在1小时内加入剩余的引发剂溶液(42克)。最后将该混合物后聚合2小时的时间。
溶液的固体含量为约10%。
实施例P4
首先在温和的氮气流下引入836克去离子水、60克N-乙烯基吡咯烷酮、80克50重量%浓度的季铵化的二烯丙基胺+40EO(实施例Q2)的水溶液和0.75克三烯丙基胺。然后用19克5重量%浓度的硫酸将其调节到pH为6.8并且加热到65℃。
一旦达到所需的65℃温度,在3小时内加入1.5克引发剂(WakoV50)在60.5克水中的20克溶液。然后将混合物加热到70℃,并且再搅拌1小时,然后在1小时内加入剩余的引发剂溶液(42克)。最后将该混合物后聚合2小时的时间。
溶液的固体含量为约10%。
将本发明聚合物P1至P4以其10重量%浓度水溶液形式用于生产下列制剂,相应地定量数据基于该水溶液。除非另有特别说明,百分含量均为重量百分含量。
FB1:含有本发明聚合物和Luviskol K30的发用凝胶
% | 原料 | 供应商 | INCI |
0.5087.600.706.005.00适量适量0.10 | Carbopol940软化水Triethanolamine Care聚合物P1LuviskolK30溶液芳香油CremophorRH 40Phenonip | (6)(1)(1)(1)(1)(42) | Carbomer软化水三乙醇胺PVP聚氧乙烯(40)氢化蓖麻油苯氧基乙醇、对羟基苯甲酸甲酯、对羟基苯甲酸丁酯、对羟基苯甲酸乙酯和对羟基苯甲 |
0.10 | 维生素E乙酸酯 | 酸丙酯生育酚乙酸酯 |
供应商
(1)BASF Aktiengesellschaft
(6)B.F.Goodrich Company Chemical Division
(42)Clariant
FB2:含有本发明聚合物和Luviskol VA64的发用凝胶
% | 原料 | 供应商 | INCI |
0.5087.600.907.004.00适量适量0.100.10 | Carbopol980软化水NeutrolTE聚合物P2LuviskolVA64 W芳香油CremophorCO 40Phenonip1,2-Propylene glycol Care | (6)(1)(1)(1)(1)(42)(1) | Carbomer软化水四羟丙基乙二胺VP/VA共聚物聚氧乙烯(40)氢化蓖麻油苯氧基乙醇、对羟基苯甲酸甲酯、对羟基苯甲酸丁酯、对羟基苯甲酸乙酯和对羟基苯甲酸丙酯丙二醇 |
供应商
(1)BASF Aktiengesellschaft
(6)B.F.Goodrich Company Chemical Division
(42)Clariant
FB3:含有本发明聚合物和Luviskol K90的发用凝胶
% | 原料 | 供应商 | INCI |
0.5087.600.706.005.00适量适量0.100.10 | CarbopolETD 2001软化水Triethanolamine Care聚合物P3LuviskolK90芳香油CremophorCO 40NipaginM十四烷酸异丙酯 | (6)(1)(1)(1)(1)(34)(27) | Carbomer软化水三乙醇胺PVP聚氧乙烯(40)氢化蓖麻油对羟基苯甲酸甲酯十四烷酸异丙酯 |
供应商
(1)BASF Aktiengesellschaft
(6)B.F.Goodrich Company Chemical Division
(34)Nipa Laboratories Ltd.
(27)Cognis Deutschland GmbH
FB4:含有本发明聚合物和Luviquat Hold的发用凝胶
% | 原料 | 供应商 | INCI |
10.002.5015.0070.305.000.100.102.00 | 聚合物P1LuviquatHold96%乙醇软化水LuviskolK90芳香油甘油Natrosol250 HR | (1)(1)(1)(20)(4) | 聚季铵盐-46乙醇软化水PVP甘油羟乙基纤维素 |
供应商
(1)BASF Aktiengesellschaft
(6)B.F.Goodrich Company Chemical Division
(20)Merck KGaA
(4)Aqualon GmbH
FB5:含有本发明聚合物和Amaze的发用凝胶
% | 原料 | 供应商 | INCI |
6.002.000.50适量适量0.100.1091.40 | 聚合物P2AmazeHydagenHCMF芳香油CremophorCO 40Abil8843Phenonip软化水 | (1)(72)(27)(1)(44)(42) | 改性玉米淀粉脱乙酰壳多糖聚氧乙烯(40)氢化蓖麻油PET-14聚二甲基硅氧烷苯氧基乙醇、对羟基苯甲酸甲酯、对羟基苯甲酸丁酯、对羟基苯甲酸乙酯和对羟基苯甲酸丙酯软化水 |
供应商
(1)BASF Aktiengesellschaft
(6)B.F.Goodrich Company Chemical Division
(27)Cognis Deutschland GmbH
(42)Clariant
(44)Th.Goldschmidt AG
(72)National Starch & Chemical Limited
FB6:含有本发明聚合物和Styleze CC-10的发用凝胶
% | 原料 | 供应商 | INCI |
8.005.00 | 聚合物P3StylezeCC-10 | (1)(65) | VP/DMAPA丙烯酸酯共聚物 |
0.0584.85适量适量0.100.102.00 | AMP软化水芳香油CremophorRH 40Dow Corning 190PhenonipKlucel | (56)(1)(16)(42)(4) | 氨甲基丙醇软化水聚氧乙烯(40)氢化蓖麻油含聚氧乙烯或聚氧丙烯侧链的聚二甲基硅氧烷苯氧基乙醇、对羟基苯甲酸甲酯、对羟基苯甲酸丁酯、对羟基苯甲酸乙酯和对羟基苯甲酸丙酯羟丙基纤维素 |
供应商
(1)BASF Aktiengesellschaft
(4)Aqualon GmbH
(16)Dow Corning Corporation
(42)Clariant
(56)Angus Chemical Company
(65)ISP Global Technologies Deutschland GmbH
FB7:含有本发明聚合物和Styleze 2000的发用凝胶
% | 原料 | 供应商 | INCI |
6.001.000.2690.64适量适量 | 聚合物P1Styleze2000AMP软化水芳香油CremophorRH40 | (1)(65)(56)(1) | VP/丙烯酸酯/甲基丙烯酸月桂酯共聚物氨甲基丙醇软化水聚氧乙烯(40)氢化蓖麻油 |
0.100.102.00 | Karion F LiquidPhenonip羟丙基瓜耳胶 | (20)(42) | 山梨糖醇苯氧基乙醇、对羟基苯甲酸甲酯、对羟基苯甲酸丁酯、对羟基苯甲酸乙酯和对羟基苯甲酸丙酯羟丙基瓜耳胶 |
供应商
(1)BASF Aktiengesellschaft
(20)Merck KGaA
(42)Clariant
(56)Angus Chemical Company
(65)ISP Global Technologies Deutschland GmbH
FB8:含有本发明聚合物和Allianz LT-120的发用凝胶
% | 原料 | 供应商 | INCI |
0.5090.010.706.002.000.19适量适量0.010.10 | Ultrez10软化水Triethanolamine Care聚合物P2AllianzLT-120AMP芳香油CremophorCO40PluracareE400Phenonip | (6)(1)(1)(61)(56)(1)(42) | Carbomer软化水三乙醇胺丙烯酸酯/C1-2琥珀酸酯/羟基丙烯酸酯共聚物氨甲基丙醇聚氧乙烯(40)氢化蓖麻油聚乙二醇-8苯氧基乙醇、对羟基苯甲酸甲酯、对羟基苯甲酸丁酯、对羟基苯甲酸乙酯和对羟基 |
0.50 | Natrosol250 HR | (4) | 苯甲酸丙酯羟乙基纤维素 |
供应商
(1)BASF Aktiengesellschaft
(4)Aqualon GmbH
(6)B.F.Goodrich Company Chemical Division
(42)Clariant
(56)Angus Chemical Company
(61)Rohm & Haas GmbH
FB9:含有本发明聚合物和Fixomer A30的发用凝胶
% | 原料 | 供应商 | INCI |
7.007.000.70适量适量0.100.1084.901.00 | 聚合物P4FixomerA30Triethanolamine Care芳香油CremophorCO40D-Panthenol USPPhenonip软化水Sepigel305 | (1)(1)(1)(1)(42)(175) | 三乙醇胺聚氧乙烯(40)氢化蓖麻油泛醇苯氧基乙醇、对羟基苯甲酸甲酯、对羟基苯甲酸丁酯、对羟基苯甲酸乙酯和对羟基苯甲酸丙酯软化水 |
供应商
(1)BASF Aktiengesellschaft
(42)Clariant
(175)Seppic
FB10:含有本发明聚合物和PVF的发用凝胶
% | 原料 | 供应商 | INCI |
0.5090.500.707.001.00适量适量0.100.100.10 | Carbopol940软化水Triethanolamine Care聚合物P1PVF芳香油CremophorRH 40PhenonipUvinulMC 80Abil8843 | (6)(1)(1)(72)(1)(42)(1)(44) | Carbomer软化水三乙醇胺聚乙烯基甲酰胺聚氧乙烯(40)氢化蓖麻油苯氧基乙醇、对羟基苯甲酸甲酯、对羟基苯甲酸丁酯、对羟基苯甲酸乙酯和对羟基苯甲酸丙酯甲氧基肉桂酸乙基己酯聚二甲基PEG-14硅氧烷(PEG-14 Dimethicone) |
供应商
(1)BASF Aktiengesellschaft
(6)B.F.Goodrich Company Chemical Division
(42)Clariant
(44)Th.Goldschmidt AG
(72)National Starch & Chemical Limited
FB11:含有本发明聚合物的发用凝胶
% | 原料 | 供应商 | INCI |
0.5088.50 | Carbopol940软化水 | (6) | Carbomer软化水 |
0.7010.00适量适量0.100.100.10 | Triethanolamine Care聚合物P4芳香油CremophorCO 40Phenonip1,2-Propylene glycol Care十四烷酸异丙酯 | (1)(1)(1)(42)(1)(27) | 三乙醇胺乙二胺聚氧乙烯(40)氢化蓖麻油苯氧基乙醇、对羟基苯甲酸甲酯、对羟基苯甲酸丁酯、对羟基苯甲酸乙酯和对羟基苯甲酸丙酯丙二醇十四烷酸异丙酯 |
供应商
(1)BASF Aktiengesellschaft
(6)B.F.Goodrich Company Chemical Division
(27)Cognis Deutschland GmbH
(42)Clariant
FB12:含有本发明聚合物的发用凝胶
% | 原料 | 供应商 | INCI |
10.0015.0072.700.100.100.102.00 | 聚合物P296%乙醇软化水芳香油甘油D-Panthenol USPNatrosol250 HR | (1)(20)(1)(4) | 软化水甘油泛醇羟乙基纤维素 |
供应商
(1)BASF Aktiengesellschaft
(6)B.F.Goodrich Company Chemical Division
(20)Merck KGaA
(4)Aqualon GmbH
FB13:含有本发明聚合物的发用凝胶
% | 原料 | 供应商 | INCI |
0.5088.500.7010.00适量适量0.100.100.10 | CarbopolETD 2001软化水Triethanolamine Care聚合物P1芳香油CremophorCO 40NipaginMUvinulMC 80Abil8843 | (6)(1)(1)(1)(34)(1)(44) | Carbomer软化水三乙醇胺聚氧乙烯(40)氢化蓖麻油对羟基苯甲酸甲酯甲氧基肉桂酸乙基己酯聚二甲基PEG-14硅氧烷 |
供应商
(1)BASF Aktiengesellschaft
(6)B.F.Goodrich Company Chemical Division
(34)Nipa Laboratories Ltd.
(44)Th.Goldschmidt AG
FB13a:含有本发明聚合物的发用凝胶
% | 原料 | 供应商 | INCI |
10.00适量适量0.100.10 | 聚合物P3芳香油CremophorCO 40PalatinolALuvitolEHO | (1)(1)(1)(1) | 聚氧乙烯(40)氢化蓖麻油邻苯二甲酸二乙酯乙基己酸十六/十八烷酯 |
0.100.1087.702.00 | CetiolHEPhenonip软化水LuvigelEM | (27)(42)(1) | 聚氧乙烯(7)甘油醚椰油酸酯苯氧基乙醇、对羟基苯甲酸甲酯、对羟基苯甲酸丁酯、对羟基苯甲酸乙酯和对羟基苯甲酸丙酯软化水甘油三(辛酸/癸酸)酯/丙烯酸酯共聚物 |
供应商
(1)BASF Aktiengesellschaft
(27)Cognis Deutschland GmbH
(42)Clariant
FB14:含有本发明聚合物的定型溶液
% | 原料 | 供应商 | INCI |
62.6030.000.100.100.100.107.00 | 96%乙醇软化水Dow Corning 190 Polyether芳香油UvinulMC 80D-Panthenol USP聚合物P4 | (16)(1)(1)(1) | 乙醇软化水含聚氧乙烯或聚氧丙烯侧链的聚二甲基硅氧烷甲氧基肉桂酸乙基己酯泛醇 |
供应商
(1)BASF Aktiengesellschaft
(16)Dow Corning Corporation
FB15:含有本发明聚合物的定型溶液
% | 原料 | 供应商 | INCI |
0.100.05适量53.8240.006.00 | Dow Corning 190 PolyetherDow Corning 344 fluid芳香油96%乙醇软化水聚合物P1 | (16)(16)(1) | 含聚氧乙烯或聚氧丙烯侧链的聚二甲基硅氧烷环状聚二甲基硅氧烷乙醇软化水 |
供应商
(1)BASF Aktiengesellschaft
(16)Dow Corning Corporation
FB16:含有本发明聚合物的定型溶液
% | 原料 | 供应商 | INCI |
0.100.100.100.4010.0084.30适量5.00 | D-Panthenol USPNutrilan Keratin WElastinPG2000UvinulM40软化水96%乙醇芳香油聚合物P2 | (1)(1)(1) | 泛醇水解弹性蛋白2-羟基-4-甲氧基二苯甲酮软化水乙醇 |
供应商
(1)BASF Aktiengesellschaft
FB17:含有本发明聚合物和Luviquat Style的定型溶液
% | 原料 | 供应商 | INCI |
4.00 | 聚合物P2 | (1) | 聚乙烯基己内酰胺 |
3.5072.2020.00适量 | LuviquatStyle96%乙醇软化水芳香油 | (1) | 聚季铵盐-16乙醇软化水 |
供应商
(1)BASF Aktiengesellschaft
FB18:含有本发明聚合物的定型溶液
% | 原料 | 供应商 | INCI |
4.000.200.1010.0085.70 | 聚合物P1PluracareE 400芳香油软化水96%乙醇 | (1)(1) | 聚乙二醇-8乙醇 |
供应商
(1)BASF Aktiengesellschaft
FB19:含有本发明聚合物的泵式喷雾剂
% | 原料 | 供应商 | INCI |
26.0073.700.100.100.10 | 聚合物P396%乙醇芳香油UvinulMC 80Dow Corning 190 | (1)(1)(16) | 乙醇甲氧基肉桂酸乙基己酯PEG/PPG-18/18聚二甲基硅氧烷(PEG/PPG-18/18Dimethicone) |
供应商
(1)BASF Aktiengesellschaft
(16)Dow Corning Corporation
FB20:含有本发明聚合物的泵式喷雾剂
% | 原料 | 供应商 | INCI |
26.004.0069.600.100.100.10 | 聚合物P2LuviskolPlus96%乙醇UvinulMC 80Dow Corning 344Dow Corning 556 | (1)(1)(1)(16)(16) | 聚乙烯基己内酰胺乙醇甲氧基肉桂酸乙基己酯环状聚二甲基硅氧烷聚三甲基苯基硅氧烷 |
供应商
(1)BASF Aktiengesellschaft
(16)Dow Corning Corporation
FB21:含有本发明聚合物的气溶胶型喷雾剂NON VOC
% | 原料 | 供应商 | INCI |
13.000.100.100.1046.7040.00 | 聚合物P4芳香油1,2-Propylene glycol CareCitroflex 2软化水HFC 152A | (1)(1)(53) | 丙二醇柠檬酸三乙酯软化水Hydrofluorocarbon 152a |
供应商
(1)ASF Aktiengesellschaft
(53)fizer Chemie
FB22:含有本发明聚合物和Luviset CAN的气溶胶型喷雾剂NON VOC
% | 原料 | 供应商 | INCI |
10.002.000.160.100.1052.6435.00 | 聚合物P1LuvisetCANAMP芳香油植烷三醇软化水HFC 152A | (1)(1)(56)(1) | VA/巴豆酸酯/新癸酸乙烯基酯共聚物氨甲基丙醇植烷三醇软化水Hydrofluorocarbon 152a |
供应商
(1)ASF Aktiengesellschaft
(56)Angus Chemical Company
FB23:含有本发明聚合物和Luviset P.U.R.的气溶胶型喷雾剂VOC 55
% | 原料 | 供应商 | INCI |
7.007.0014.3036.500.100.1040.00 | 聚合物P4LuvisetP.U.R.无水乙醇软化水1,2-Propylene glycol Care芳香油DME | (1)(1)(1) | 聚氨酯-1新癸酸酯共聚物乙醇软化水丙二醇二甲醚 |
供应商
(1)ASF Aktiengesellschaft
FB24:含有本发明聚合物和Luviskol Plus的气溶胶型喷雾剂VOC 55
% | 原料 | 供应商 | INCI |
10.005.00 | 聚合物P2LuviskolPlus | (1)(1) | 聚乙烯基己内酰胺 |
17.0032.800.100.1035.00 | 无水乙醇软化水烟酰胺芳香油DME | 乙醇软化水烟酰胺二甲醚 |
供应商
(1)ASF Aktiengesellschaft
FB25:含有本发明聚合物和Luvimer 100P的气溶胶型喷雾剂VOC 80
% | 原料 | 供应商 | INCI |
10.001.000.2435.008.560.100.1010.0035.00 | 聚合物P3Luvimer100PAMP无水乙醇软化水BelsilCM040芳香油正丁烷DME | (1)(1)(56)(156)-- | 丙烯酸酯共聚物氨甲基丙醇乙醇软化水环戊硅氧烷(cyclopentasiloxane)丁烷二甲醚 |
供应商
(1)ASF Aktiengesellschaft
(56)Angus Chemical Company
(156)Wacker Chemie GmbH
FB26:含有本发明聚合物和Luviskol VA37的气溶胶型喷雾剂VOC 80
% | 原料 | 供应商 | INCI |
10.00 | 聚合物P1 | (1) |
4.0038.007.700.100.100.1040.00 | LuviskolVA37无水乙醇软化水D-Panthenol USPDow Corning 556芳香油DME | (1)(1)(16)- | VP/VA共聚物乙醇软化水泛醇聚三甲基苯基硅氧烷二甲醚 |
供应商
(1)ASF Aktiengesellschaft
(16)Dow Corning Corporation
FB27:含有本发明聚合物和Luviflex Silk的无添加水的气溶胶型喷雾剂
% | 原料 | 供应商 | INCI |
7.004.000.4748.230.100.100.1010.0030.00 | 聚合物P1LuviflexSilkAMP无水乙醇PalatinolAD-Panthenol USP芳香油丙烷/丁烷DME | (1)(1)(56)(1)(1)-- | PEG/PPG-25/25聚二甲基硅氧烷(PEG/PPG-25/25Dimethicone)/丙烯酸酯共聚物氨甲基丙醇乙醇邻苯二甲酸二乙酯泛醇丙烷/丁烷二甲醚 |
供应商
(1)ASF Aktiengesellschaft
(56)Angus Chemical Company
FB28:含有本发明聚合物和Amphomer的无添加水的气溶胶型喷雾剂
% | 原料 | 供应商 | INCI |
10.001.000.1743.530.100.100.1045.00 | 聚合物P4Amphomer28-4910AMP无水乙醇Dow Corning 193Dow Corning 556芳香油DME | (1)(72)(56)(16)(16)- | 丙烯酸酯共聚物氨甲基丙醇乙醇聚二甲基PEG-12硅氧烷(PEG-12 Dimethicone)聚三甲基苯基硅氧烷二甲醚 |
供应商
(1)ASF Aktiengesellschaft
(16)Dow Corning Corporation
(56)Angus Chemical Company
(72)National Starch & Chemical Limited
混合程序
FB29:含有本发明聚合物的泵式头发定型泡沫
3.00 聚合物P1
1.00 LuviquatMono CP 羟乙基十六烷基磷酸二铵
0.20 CremophorA 25 十六/十八醇聚氧乙烯(25)醚
0.40 芳香油PC 910.781/
Cremophor
95.40 软化水 软化水
适量 防腐剂
制备:
由各组分制备均匀混合物并将其输送到泵式泡沫瓶中。
FB30:泵式喷雾剂
A 适量 CremophorCO 40 聚氧乙烯(40)氢化蓖麻油
适量 芳香油
75.50 软化水 软化水
7.30 聚合物P1
B 1.00 1,2-Propylene glycol Care 丙二醇
0.20 UvinulP25 PEG-25 PABA
1.00 LuviquatHM 552 聚季铵盐-16
15.00 96%乙醇 乙醇
制备:
搅拌A相。依次加入B相的各组分,使其均匀分布并装瓶。
FB31:含有本发明聚合物的定型水
A 0.70 CremophorCO 40 聚氧乙烯(40)氢化蓖麻油
0.20 芳香油
75.10 软化水 软化水
7.30 聚合物P1
B 1.00 1,2-Propylene glycol Care 丙二醇
0.50 LuviquatUltracare 聚季铵盐-44
0.20 UvinulP25 PEG-25 PABA
15.00 96%乙醇 乙醇
制备:
搅拌A相。依次加入B相的各组分,使其均匀分布并装瓶。
FB32:含有本发明聚合物的发用泡沫
A 0.70 CremophorCO 40 聚氧乙烯(40)氢化蓖麻油
0.20 芳香油
78.50 软化水 软化水
B 0.50 LuviquatMono LS 椰油基三甲基甲基硫酸铵
6.70 聚合物P3
2.50 LuviquatHold 聚季铵盐-46
0.20 UvinulP 25 PEG-25 PABA
0.50 PluracareE 400 聚乙二醇-8
0.20 Cremophor A 25 十六/十八醇聚氧乙烯(25)醚
适量 防腐剂
C 10.00 丙烷/丁烷3.5巴(20℃) 丙烷/丁烷
制备:
搅拌A相。依次加入B相的各组分,使其均匀分布并与C相一起装瓶。
FB33:含有本发明聚合物的定型摩丝
A 2.00 LuviquatMono LS 椰油基三甲基甲基硫酸铵
适量 芳香油
B 62.85 软化水 软化水
7.00 聚合物P1
2.00 LuviquatPQ 11 聚季铵盐-11
0.20 Cremophor A 25 十六/十八醇聚氧乙烯(25)
醚
0.50 D-Panthenol USP 泛醇
0.05 UvinulMS 40 5-苯甲酰基-4-羟基-2-甲氧
基苯磺酸
0.20 Dow Corning 949 Cationic
15.00 96%乙醇 乙醇
C 0.20 Natrosol250 HR 羟乙基纤维素
D 10.00 丙烷/丁烷3.5巴(20℃) 丙烷/丁烷
制备:
混合A相。依次加入B相的各组分并混合。加入C相并搅拌直到均匀分布。将pH值调节到6-7。与D相一起装瓶。
FB34:含有本发明聚合物的定型泡沫
A 2.00 LuviquatMono LS 椰油基三甲基甲基硫酸铵
适量 芳香油
B 83.13 软化水 软化水
0.47 AMP 氨甲基丙醇
0.20 防腐剂
0.20 AbilB 8843 含聚氧乙烯或聚氧丙烯侧链
的聚二甲基硅氧烷
C 4.00 聚合物P1
D 10.00 丙烷/丁烷3.5巴(20℃) 丙烷/丁烷
制备:
混合A相。称入B相并使其溶解至澄清。将B相搅拌入A相中。加入C相并搅拌。与D相一起装瓶。
FB35:含有本发明聚合物的润湿外观的定型泡沫
A 3.00 LuviquatMono LS 椰油基三甲基甲基硫酸铵
0.20 芳香油
B 78.80 软化水 软化水
C 5.00 87%甘油 甘油
适量 防腐剂
3.00 聚合物P2
D 10.00 丙烷/丁烷3.5巴(20℃) 丙烷/丁烷
制备:
混合A相。将B相搅拌入A相中。加入C相。与D相一起装瓶。
FB36:含有本发明聚合物的泡沫调理剂
5.00 LuviquatPQ 11 聚季铵盐-11
5.00 聚合物P2
0.50 LuviquatMono CP 羟乙基十六烷基磷酸二铵
10.00 无水乙醇 乙醇
0.40 芳香油“Carina”/
CremophorRH
适量 防腐剂
69.10 软化水 软化水
10.00 丙烷/丁烷 丙烷/丁烷
制备:
将所有物质一起称重,搅拌直至均匀分布。装瓶。
FB37:含有本发明聚合物的亮泽发蜡
5.00 LuvitolEHO 辛酸十六/十八烷酯
5.00 蓖麻油 蓖麻(Ricinus Communis)油
17.00 凡士林 矿脂
7.00 TeCero-Wachs1030 K 微晶蜡
6.00 蜂蜡3044 PH 蜂蜡
5.00 聚合物P1(无水)
3.00 UvinulMBC 95 4-甲基亚苄基樟脑
2.00 UvinulBMBM 丁基甲氧基二苯甲酰基甲烷
0.10 植烷三醇 植烷三醇
0.50 苯氧基乙醇 苯氧基乙醇
48.40 蜡油,高粘度 矿物油
11.00 Dow Corning 556 fluid 聚三甲基苯基硅氧烷
适量 芳香油
制备:
称入A相的各组分并熔融。
FB38:彩色香脂
A 1.50 CremophorA 6 十六/十八醇聚氧乙烯(6)醚,
硬脂醇
1.50 CremophorA 25 十六/十八醇聚氧乙烯(25)醚
3.00 十六/十八醇 十六/十八醇
6.00 LuvitolEHO 辛酸十六/十八烷酯
0.30 植烷三醇 植烷三醇
B 7.70 LuviquatUltracare 聚季铵盐-44
6.00 聚合物P4
2.00 1,2-Propylene glycol Care 丙二醇
1.00 D-Panthenol USP 泛醇
适量 防腐剂
70.87 软化水 软化水
C 0.05 碱性紫14 C.I.42510,碱性紫14
0.08 碱性红76 C.I.12245,碱性红76
适量 芳香油
适量 柠檬酸 柠檬酸
制备:
分别将A相和B相加热到约80℃。将B相均匀搅拌到A相中。在均化后较短时间内,将其冷却到约40℃。加入C相并再次简单均化。将pH调节到6-7。
FB39:含有本发明聚合物的头发修复处理剂
A 0.20 LuvitolEHO 辛酸十六/十八烷酯
3.00 聚合物P1
0.10 植烷三醇 植烷三醇
2.00 CremophorCO 40 聚氧乙烯(40)氢化蓖麻油
B 适量 芳香油
2.00 LuviquatMono LS 椰油基三甲基甲基硫酸铵
C 79.70 软化水 软化水
D 2.00 LuviquatExcellence 聚季铵盐-16
1.00 硅油SF 1288 含聚氧乙烯或聚氧丙烯侧链
的聚二甲基硅氧烷
适量 防腐剂
10.00 96%乙醇 乙醇
适量 柠檬酸 柠檬酸
制备:
分别混合A相和B相,将C相搅拌到B相中。将B相和C相的溶液搅拌到A相中。加入D相并搅拌至稠化。将pH调节到4-5。
FB40:含有本发明聚合物的发胶
A 0.50 Glucamate SSE-20 聚氧乙烯(20)甲基葡糖醚倍
半硬脂酸酯
适量 CremophorCO 40 聚氧乙烯(40)氢化蓖麻油
适量 芳香油
30.00 软化水 软化水
B 10.00 LuviquatHold 聚季铵盐-46
2.00 LuviskolK 90 PVP
6.00 聚合物P2
0.30 Germall115 咪唑烷基脲
0.10 EuxylK 100 苄醇,甲基氯代异噻唑啉酮,
甲基异噻唑酮
0.50 D-Panthenol USP 泛醇
5.00 PluracareE 6000 聚乙二醇-90
3.00 1,2-Propylene glycol Care 丙二醇
40.10 软化水 软化水
C 2.50 Natrosol250 HR 羟乙基纤维素
制备:
溶解A相。溶解B相并将其搅拌到A相中,将C相搅拌到A相和B相的溶液中。
FB41:含有本发明聚合物的丝质多功能发剂(SILKY HAAR-COCKTAIL)
A 3.00 LuvigelEM 甘油三(辛酸/癸酸)酯/丙烯
酸酯共聚物
3.00 聚合物P1(无水)
0.50 Wacker BelsilDMC 6031 含聚氧乙烯或聚氧丙烯侧链
的聚二甲基硅氧烷
2.00 Wacker BelsilDM 1000 聚二甲基硅氧烷
3.00 Wacker BelsilCM 1000 环状聚二甲基硅氧烷,聚二
甲基硅烷醇
2.00 Wacker BelsilADM 6057 E 氨基封端的聚二甲基硅氧
烷,十六烷基三甲基氯化铵,
十三烷基聚氧乙烯(10)醚
2.00 Wacker BelsilPDM 200 聚三甲基苯基硅氧烷
1.00 澳洲坚果油 澳洲坚果(Ternifolia)油
0.50 维生素E乙酸酯 生育酚乙酸酯
1.00 CremophorCO 40 聚氧乙烯(40)氢化蓖麻油
适量 芳香油
B 77.54 软化水 软化水
0.46 AMP 氨甲基丙醇
4.00 LuviflexSilk PEG/PPG-25/25聚二甲基硅
氧烷(PEG/PPG-25/25
Dimethicone)/丙烯酸酯共聚
物
适量 防腐剂
制备:
混合A相的各组分。溶解B相。将B相均匀搅拌到A相中。
FB42:含有本发明聚合物的油质亮泽保湿剂
A 2.00 鲸蜡醇 鲸蜡醇
1.00 SolanELD 聚氧乙烯(75)羊毛脂
4.00 甘油单硬脂酸酯 甘油硬脂酸酯
1.00 Cremophor A 25 十六/十八醇聚氧乙烯(25)醚
4.00 LuvitolEHO 辛酸十六/十八烷酯
B 10.00 87%甘油 甘油
5.00 聚合物P4
2.00 1,2-Propylene glycol Care 丙二醇
1.00 LuviquatMono LS 椰油基三甲基甲基硫酸铵
1.50 聚硅氧烷微乳液 三甲基甲硅烷基氨基封端的
聚二甲基硅氧烷,
SM 2115辛基酚聚氧乙烯(40)
醚,异月桂基聚氧乙烯(6)醚,
甘油
1.00 CremophorPS 20 聚山梨醇酯20
67.00 软化水 软化水
C 0.50 D-Panthenol USP 泛醇
适量 防腐剂
适量 芳香油
适量 柠檬酸 柠檬酸
制备:
分别将A相和B相加热到约80℃。将B相搅拌到A相中并均化。冷却到约40℃,加入C相并再次均化。
FB43:含有本发明聚合物的高亮泽的定型霜剂
A 5.00 鲸蜡醇 鲸蜡醇
10.00 Tegin 甘油硬脂酸酯SE
5.00 十四烷酸异丙酯 十四烷酸异丙酯
适量 防腐剂
1.00 Dow Corning 200 fluid 聚二甲基硅氧烷
B 5.00 87%甘油 甘油
5.00 聚合物P1
0.20 Edeta BD EDTA二钠盐
2.00 LuviskolK 30 PVP
66.80 软化水 软化水
C 适量 芳香油
制备:
分别将A相和B相加热到约80℃。将B相搅拌到A相中并均化。冷却到约40℃,加入C相并再次简单均化。
FB44:长效卷发剂
A 70.95 软化水 软化水
3.00 聚合物P1
0.20 Tego甜菜碱L7 椰油酰胺基丙基甜菜碱
0.20 CremophorPS 20 失水山梨醇聚氧乙烯(20)醚
月桂酸酯
1.25 LuviquatExcellence 聚季铵盐-16
0.20 Edeta BD EDTA二钠盐
0.20 Natrosol 250 HR 羟乙基纤维素
B 8.00 80%巯基乙酸 巯基乙酸
C 11.00 25%氨水 氢氧化铵
D 5.00 碳酸铵 碳酸铵
制备:
称入A相的各组分并混合。将B相搅拌到A相中。
FB45:含有本发明聚合物的长效卷发剂的中和剂
A 1.00 Cremophor CO 40 聚氧乙烯(40)氢化蓖麻油
0.20 芳香油
2.00 聚合物P3
91.60 软化水 软化水
B 0.20 Tego甜菜碱L7 椰油酰胺基丙基甜菜碱
0.20 CremophorA 25 十六/十八醇聚氧乙烯(25)醚
2.50 LuviquatExcellence 聚季铵盐-16
适量 防腐剂
C 2.30 30%过氧化氢 过氧化氢
D 适量 85%磷酸 磷酸
制备:
溶解A相。依次加入B相的组分并混合。加入C相并再次搅拌。将pH调节到3.0-3.5。
Claims (13)
1.一种含有下列单体结构单元的聚合物:
a)至少一种中性或季铵形式的具有通式I的二烯丙基胺(单体A)
其中
A-O是C1-C12氧化烯、氧化苯乙烯或其任意混合物,
n是2-200的整数,
x是0或1,
R1是氢,C1-C20烷基,C2-C20链烯基,C5-C10环烷基或任选取代的苄基,
R2是氢,C1-C30烷基,C5-C8环烷基,C6-C20芳基,C1-C30烷酰基,C7-C21芳酰基,硫酸(半)酯,磷酸酯,氨基或铵,
R3可以相同或不同并且是氢,C1-C20烷基,C2-C20链烯基,C5-C10环烷基或芳基,
b)至少一种选自由如下单体组成的组的烯属不饱和单体(单体B)
i N-乙烯基内酰胺,
ii N-乙烯基酰胺,
iii N-乙烯基咪唑,
iv 不同于单体A的N,N-二烯丙基胺,以及这些单体或其盐的任意混合物,
c)如果合适的话,一种或多种烯属不饱和单体C,
d)如果合适的话,至少一种交联剂。
2.根据权利要求1的聚合物,其中单体B是N-乙烯基己内酰胺或N-乙烯基吡咯烷酮。
3.根据权利要求1和2中至少一项的聚合物,其中聚合物的重均分子量Mw是1000-2000000。
4.根据权利要求1-3中至少一项的聚合物,其中聚合物具有的K值为20-120。
5.根据权利要求1-4中至少一项的聚合物,其中待聚合的单体混合物含有:
a)1-95摩尔%的单体A
b)5-99摩尔%的单体B和
c)0-50摩尔%的单体C。
6.根据权利要求1-5中任何一项的聚合物,其中该聚合物含有0.01-5重量%的交联剂,基于单体A、B和C的总重量。
7.根据权利要求1-6中至少一项的聚合物,其中该聚合物是水溶性或水分散性的。
8.一种制备根据权利要求1-7之一的聚合物的方法,其中单体A和B以及任选的C和任选的交联剂进行自由基聚合。
9.一种含有根据权利要求1-7之一的聚合物和化妆品中常用的其它添加剂的化妆品制剂。
10.一种含有根据权利要求1-7之一的聚合物和头发护理中常用的其它添加剂的头发护理组合物。
11.含有下列单体结构单元的聚合物在化妆品制剂或皮肤用制剂中的用途:
a)至少一种中性或季铵形式的具有通式I的二烯丙基胺(单体A)
其中
A-O是C1-C12氧化烯、氧化苯乙烯或其任意混合物,
n是2-200的整数,
x是0或1,
R1是氢,C1-C20烷基,C2-C20链烯基,C5-C10环烷基或任选取代的苄基,
R2是氢,C1-C30烷基,C5-C8环烷基,C6-C20芳基,C1-C30烷酰基,C7-C21芳酰基,硫酸(半)酯,磷酸酯,氨基或铵,
R3可以相同或不同并且是氢,C1-C20烷基,C2-C20链烯基,C5-C10环烷基或芳基,
b)一种或多种烯属不饱和单体
c)如果合适的话,至少一种交联剂。
12.根据权利要求11的用途,其中作为组分b)的选自由如下单体组成的组的至少一种烯属不饱和单体存在于化妆品制剂中或作为头发护理组合物:
i N-乙烯基内酰胺,
ii N-乙烯基酰胺,
iii N-乙烯基咪唑,
iv 不同于单体A的N,N-二烯丙基胺,
以及这些单体或其盐的任意混合物。
13.一种含有如权利要求12中定义的聚合物和化妆品中常用的其它添加剂的化妆品组合物。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE102004016650.1 | 2004-03-31 | ||
DE102004016650A DE102004016650A1 (de) | 2004-03-31 | 2004-03-31 | Diallylamine enthaltende Polymerisate |
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CN1938348A true CN1938348A (zh) | 2007-03-28 |
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CNA2005800097843A Pending CN1938348A (zh) | 2004-03-31 | 2005-03-26 | 含有二烯丙基胺的聚合物 |
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US (1) | US20070191548A1 (zh) |
EP (1) | EP1732961A1 (zh) |
JP (1) | JP2007530755A (zh) |
KR (1) | KR20070011420A (zh) |
CN (1) | CN1938348A (zh) |
CA (1) | CA2558550A1 (zh) |
DE (1) | DE102004016650A1 (zh) |
RU (1) | RU2006138175A (zh) |
WO (1) | WO2005095479A1 (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102341089A (zh) * | 2009-03-05 | 2012-02-01 | 汽巴公司 | 用于个人护理组合物的两性三元共聚物 |
CN107312062A (zh) * | 2010-05-17 | 2017-11-03 | Emd密理博公司 | 用于纯化生物分子的刺激响应性聚合物 |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102005026007A1 (de) * | 2005-06-03 | 2006-12-07 | Beiersdorf Ag | Kosmetische Zubereitungen mit einem Gehalt an einem besonderen Anisfruchtextrakt und sulfonierten Lichtfiltern |
DE102005026006A1 (de) * | 2005-06-03 | 2006-12-07 | Beiersdorf Ag | Kosmetische Zubereitungen mit einem Gehalt an einem besonderen Anisfruchtextrakt und Triazin-Lichtfiltern |
FR2892629B1 (fr) * | 2005-10-28 | 2012-04-27 | Oreal | Composition cosmetique comprenant au moins un polymere fixant particulier et au moins un tensioactif ionique et/ou non ionique |
US20070160560A1 (en) * | 2005-10-28 | 2007-07-12 | Ludivine Laurent | Cosmetic composition comprising at least one fixative polymer and at least one surfactant chosen from ionic and nonionic surfactants |
EP2022479A1 (en) * | 2007-08-07 | 2009-02-11 | KPSS-Kao Professional Salon Services GmbH | Hair styling composition |
US8312886B2 (en) * | 2007-08-09 | 2012-11-20 | Philip Morris Usa Inc. | Oral tobacco product having a hydrated membrane coating and a high surface area |
FR2948874A1 (fr) * | 2009-08-07 | 2011-02-11 | Oreal | Composition cosmetique comprenant des poly(diallylamines alcoxyles) quaternises, et procede de traitement cosmetique |
FR2948873A1 (fr) * | 2009-08-07 | 2011-02-11 | Oreal | Composition cosmetique comprenant des poly(diallylamines alcoxyles) neutralises, et procede de traitement cosmetique |
RU2466148C1 (ru) * | 2011-05-03 | 2012-11-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Кабардино-Балкарский государственный университет им. Х.М. Бербекова" | Сополимер на основе n,n-диаллиламиноэтановой кислоты и винилацетата |
FR2984142B1 (fr) * | 2011-12-20 | 2013-12-20 | Oreal | Composition comprenant un polymere acrylique particulier et copolymere silicone, procede de traitement des fibres keratiniques le mettant en oeuvre |
DE102014214463B4 (de) * | 2014-07-24 | 2024-09-19 | Beiersdorf Aktiengesellschaft | Deodorantzubereitungen umfassend Polyquaternium Polymere |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
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DE19543366C2 (de) * | 1995-11-21 | 1998-09-10 | Stockhausen Chem Fab Gmbh | Mit ungesättigten Aminoalkoholen vernetzte, wasserquellbare Polymerisate, deren Herstellung und Verwendung |
DE10241296A1 (de) * | 2002-09-04 | 2004-03-18 | Basf Ag | Verwendung von vernetzten kationischen Polymerisaten in der Kosmetik |
-
2004
- 2004-03-31 DE DE102004016650A patent/DE102004016650A1/de not_active Withdrawn
-
2005
- 2005-03-26 US US10/594,959 patent/US20070191548A1/en not_active Abandoned
- 2005-03-26 KR KR1020067022660A patent/KR20070011420A/ko not_active Application Discontinuation
- 2005-03-26 RU RU2006138175/04A patent/RU2006138175A/ru unknown
- 2005-03-26 CA CA002558550A patent/CA2558550A1/en not_active Abandoned
- 2005-03-26 EP EP05733710A patent/EP1732961A1/de not_active Withdrawn
- 2005-03-26 JP JP2007505468A patent/JP2007530755A/ja not_active Withdrawn
- 2005-03-26 WO PCT/EP2005/003215 patent/WO2005095479A1/de active Application Filing
- 2005-03-26 CN CNA2005800097843A patent/CN1938348A/zh active Pending
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102341089A (zh) * | 2009-03-05 | 2012-02-01 | 汽巴公司 | 用于个人护理组合物的两性三元共聚物 |
CN102341089B (zh) * | 2009-03-05 | 2014-07-02 | 汽巴公司 | 用于个人护理组合物的两性三元共聚物 |
CN107312062A (zh) * | 2010-05-17 | 2017-11-03 | Emd密理博公司 | 用于纯化生物分子的刺激响应性聚合物 |
Also Published As
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KR20070011420A (ko) | 2007-01-24 |
JP2007530755A (ja) | 2007-11-01 |
RU2006138175A (ru) | 2008-05-10 |
EP1732961A1 (de) | 2006-12-20 |
CA2558550A1 (en) | 2005-10-13 |
US20070191548A1 (en) | 2007-08-16 |
DE102004016650A1 (de) | 2005-10-20 |
WO2005095479A1 (de) | 2005-10-13 |
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