CN1814655A - 吸收紫外线的季铵化聚硅氧烷 - Google Patents
吸收紫外线的季铵化聚硅氧烷 Download PDFInfo
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- CN1814655A CN1814655A CNA2006100062982A CN200610006298A CN1814655A CN 1814655 A CN1814655 A CN 1814655A CN A2006100062982 A CNA2006100062982 A CN A2006100062982A CN 200610006298 A CN200610006298 A CN 200610006298A CN 1814655 A CN1814655 A CN 1814655A
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- dimethyl amine
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- acid
- compound
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Abstract
本发明涉及吸收紫外线的季铵化聚硅氧烷,其中季铵基团与吸收紫外线的基团可以根据通式(I)而彼此独立地被混合起来。
Description
技术领域
本发明涉及吸收紫外线的季铵化聚硅氧烷、其制备方法及其在配制织物护理和化妆品制剂中的用途。
背景技术
已知200-400nm波长的紫外线是造成织物、合成纤维和天然纤维(例如,羊毛、棉花和毛发)漂白和损伤的原因。
为此,对于防护织物、合成纤维和天然纤维以使其免受紫外线辐射或者可以控制损伤程度的化合物具有不断增长的需要。
因此,人们希望提供能够对织物或者合成或天然纤维暴露于其下的紫外线辐射进行控制的化合物。
文献中公开了许多用于对纤维、染料和颜料进行紫外线防护的化合物。这些化合物通常直接用在纤维的制造中。
然而这些化合物不具有护理或者软化作用。此外,这些化合物通常缺少对纤维表面的附着力,这意味着仅仅经过几次洗涤操作后就丧失了对紫外线的防护作用。
因此人们希望提供对天然或合成纤维产生护理作用、对纤维显示出高度亲和性(substantivity)、而且另外对机械和/或光学(例如,紫外线)引起的损伤提供防护作用的化合物。
为了即使在多次洗涤后仍能够提供充分的紫外防护作用,该化合物还应该能够结合到纤维软化剂组合物中、并且在纤维软化过程中附着在纤维上。
季铵化聚硅氧烷同样在文献中已知,并且记载于例如专利EP-A-0 282 720和DE-A-37 19 086中。这类化合物特别地由于其在美发用品中的调理(conditioning)性能及其在织物处理中的软化和护理作用而为人们所知。为了提高织物的弹性和抗撕强度并且减少其褶皱或者折痕的形成和/或便于后来的熨烫(“易于熨烫”),也使用了这种类型的化合物(WO-A-01/25385、WO-A-01/25382、WO-A-01/25381、WO-A-01/25380、WO-A-99/55953)。然而,如专利EP-B-0 282 720和DE-C-37 19 086中描述的化合物没有显示出能防护紫外线辐射的有害作用。
DE-A-101 41 356和US-B-6 630 132中已经描述了键合在聚硅氧烷骨架上的季铵基团与吸收紫外线的基团的组合。根据该现有技术,这些化合物的缺点是每个吸收紫外线的基团上包含一个季氮原子。在高度紫外线吸收的情况下,会由此产生很高的阳离子电荷密度。因此,电荷密度与紫外线的吸收之间的比例不能够随意变化。
那么,本发明的综合目的就是提供基于聚硅氧烷的化合物,其中季铵和吸收紫外线的基团的含量可以彼此独立地随意变化。这些化合物对天然或合成纤维(例如,羊毛、棉花或者毛发)或者其它表面(例如,皮肤)的亲和性将能随意调节,通过聚硅氧烷链将可以得到对天然或者合成纤维的光滑、护理和软化作用,此外还将可以减少由机械和/或光学作用(例如,紫外线)所产生的损伤。
令人惊讶地,现已发现上述目的通过在聚硅氧烷骨架上将季铵与吸收紫外线的基团独立地组合而得以实现。
发明内容
因此,本发明提供通式(I)的吸收紫外线的季铵化聚硅氧烷
其中,基团
R1为相同或不同,并且在每种情况下为具有1-22、优选1-4个碳原子的烷基,或者苯基,
R2可以有一部分具有基团R1的含义,而其它的R2基团彼此独立地为式(Ia或Ib)的基团
R2=-M-S (Ia)
或者
R2=-M-Z+A- (Ib)
条件是在平均分子中,至少两个R2基团各自为式-M-S和-M-Z+A-的基团,
其中
S为决定紫外线吸收的单价生色团,尤其是式(Ic)的基团
其中
R4为-CH=CH-,
R5为相同或不同,并且在每种情况下为氢、烷基、卤代烷基、卤素、苯基、羟基、烷氧基、氨基、烷基氨基、二烷基氨基、二(羟基烷基)氨基或者二(聚烷氧基)氨基,
m=0或1,
n=0或1,
o=0-5
以及
Z+为式(Id)的基团
R6、R7为具有1-22个碳原子的烷基,或者具有2-22个碳原子的烯基,其中所述烷基或者烯基可以具有羟基,
R9可以为具有1-22个碳原子的单价烃基,
或者
为根据式(Ic)的基团,
x=0-6,
y=0或1
并且
M为具有至少4个碳原子的二价烃基,其具有羟基并且可以被一个或多个氧原子中断,
A-为源自常规的生理相容性酸HA的无机或者有机阴离子,
a各自独立地为1-200的值,并且
b为0-10的值。
本发明进一步提供一种制备根据本发明的化合物的方法,其包括以其本身为本领域公知的方式,基于叔胺并在40-120℃的温度下,在常规的生理相容性有机或者无机酸等效HA存在的条件下使式(II)的化合物
其中,基团
R1相同或不同,并且在每种情况下都为具有1-22、特别是1-4个碳原子的烷基,或者苯基,
E可以一部分具有基团R1的含义,而其它的E基团为具有下述通式的单价基团
其中
c,e彼此独立地为0-10,尤其为1-3,总和≥4,
d为0或1,并且
R11可以为H或者具有1-10个碳原子的单价烃基,
条件是,在平均分子中存在至少两个基团E,
a各自独立地为1-200的值,并且
b为0-10的值,
与至少一种通式(IIa)的化合物发生反应
其中
F为OH或者NH2,
R10为决定紫外线吸收的单价生色团,并且为式(Ic,其中m=0)的基团,
以及另外地与至少一种通式(IIb)的叔胺发生反应
其中
R6、R7为具有1-22个碳原子的烷基或者具有2-22个碳原子的烯基,其中所述的烷基或者烯基可以具有羟基,
R9可以为具有1-22个碳原子的单价羟基,
或者
为根据式(Ic)的基团,
其中
x=0-6,
y=0或1。
聚硅氧烷(II)与式(IIa)和(IIb)的反应物的反应还可依次在两个独立的、分离的反应步骤中进行。
式(IIa)和(IIb)化合物的用量比例彼此独立,并且可在0.001∶1-1∶0.001,尤其是0.1∶1-1∶0.1的范围内变化。
基团R1优选的实例为具有1-22、尤其是1-4个碳原子的烷基,或者苯基,例如甲基、乙基、正丙基、异丙基、正丁基或者异丁基。
基团M优选的实例为:
在本发明的化合物中,基团S和Z+可以具有相同或者不同的含义。
基团S优选的实例为:
基团Z优选的实例为辛基二甲基胺、月桂基二甲基胺、椰油二甲基胺(cocodimethylamine)、十四烷基二甲基胺、十六烷基二甲基胺、硬脂基二甲基胺、山嵛基二甲基胺(behenyldimethylamine)、油基二甲基胺、辛酰胺基丙基二甲基胺、月桂酰胺基丙基二甲基胺、椰油酰胺基丙基二甲基胺、十四烷酰胺基丙基二甲基胺、棕榈酰胺基丙基二甲基胺、硬脂酰胺基丙基二甲基胺、山嵛酰胺基丙基二甲基胺、油酰胺基丙基二甲基胺、十一碳烯酰胺基丙基二甲基胺、蓖麻酰胺基丙基二甲基胺和胍基丙基二甲基胺。
源自常规的生理相容性酸HA的无机或有机阴离子A-优选的实例为醋酸根离子、氯离子、溴离子、硫酸氢根离子、硫酸根离子、甲硫酸根离子、乙硫酸根离子、柠檬酸根离子、酒石酸根离子和乳酸根离子、以及芳香酸的阴离子,例如对甲苯磺酸、苯甲酸、水杨酸、肉桂酸、4-甲氧基肉桂酸、4-氨基苯甲酸、4-双(羟基丙基)氨基苯甲酸、4-双(聚乙氧基)氨基苯甲酸、4-二甲基氨基苯甲酸、3-咪唑-4-基丙烯酸、2-苯基苯并咪唑-5-磺酸、3,3’-(1,4-亚苯二次甲基)双(7,7-二甲基-2-氧代双环[2.2.1]庚烷-1-甲磺酸)、2-羟基-4-甲氧基二苯甲酮-5-磺酸和3-(4’-磺基)苄叉莰-2-酮的阴离子。
本领域技术人员已知,所述化合物以混合物的形式存在,其分布基本上由统计学原理控制。因此指数a和b的值代表平均值。
吸收紫外线的季铵化聚硅氧烷优选的实例为具有下列通式的化合物
g | h | i |
5873405890 | 352083224 | 55286 |
g | h | i |
5873405890 | 352083224 | 55286 |
附图说明
图1为实施例1化合物的UV-可见光谱谱图(0.005%,在异丙醇中)。
图2为实施例2化合物的UV-可见光谱谱图(0.005%,在异丙醇中)。
图3为实施例3化合物的UV-可见光谱谱图(0.0075%,在异丙醇中)。
具体实施方式
下面实施例中对制备本发明化合物的方法以及这些化合物的性质进行了更详细地描述:
实施例
实施例1
本发明具有下述通式的吸收紫外线的季铵化聚硅氧烷的制备:
最初先将5.5g(0.0176mol)具有下述通式的叔胺:
与1.9g(0.032mol)醋酸和16.5g肉桂酸(0.111mmol)以及30ml异丙醇一起引入到安装有搅拌器、滴液漏斗、温度计和回流冷凝器的250ml四颈烧瓶中。5分钟后,滴加42g(0.14mol环氧)下述通式的环氧聚硅氧烷:
将其加热至回流温度并搅拌6小时。然后在l00℃下减压蒸馏混合物。得到高粘度、黄褐色的产物。
实施例1的UV-可见光谱谱图(0.005%,在异丙醇中)见图1。该谱图显示了肉桂酸单元在275nm处的宽特征吸收带。强度与所用的肉桂酸的量相关。
实施例2:
本发明具有下述通式的吸收紫外线的季铵化聚硅氧烷的制备:
最初先将6.3g(0.02mol)具有下述通式的叔胺:
与1.3g(0.021mol)醋酸和11.8g肉桂酸(0.08mol)和30ml异丙醇一起加入到安装有搅拌器、滴液漏斗、温度计和回流冷凝器的250ml四颈烧瓶中。5分钟后,滴加38g(0.10mol环氧)下述通式的环氧聚硅氧烷:
加热至回流温度并且搅拌6小时。然后在100℃下减压蒸馏混合物。得到高粘度、黄褐色的产物(季氮实测值:1.65%;理论值:1.9%)。
实施例2的UV-可见光谱谱图(0.005%,在异丙醇中)见图2。该谱图显示了肉桂酸单元在275nm处的宽特征吸收带。强度与所用的肉桂酸的量相关。
实施例3:
本发明的具有下述通式的吸收紫外线的季铵化聚硅氧烷的制备:
最初先将15.8g(0.05mol)具有下述通式的叔胺:
与3.8g(0.051mol)醋酸和35.6g 4-甲氧基肉桂酸(0.2mol)以及30ml异丙醇一起加入到安装有搅拌器、滴液漏斗、温度计和回流冷凝器的250ml四颈烧瓶中。5分钟后,滴加97.6g(0.25mol环氧)的下述通式的环氧聚硅氧烷:
加热至回流温度并且搅拌6小时。然后在100℃下减压蒸馏混合物。得到高粘度、蜡状、黄褐色的产物。
实施例3的UV-可见光谱谱图(0.0075%,在异丙醇中)见图3。该谱图显示了在280和320nm之间有宽最大值的甲氧基肉桂酸单元的特征吸收带。其强度与所用的甲氧基肉桂酸的量相关。
性能比较:
使用了下列本发明吸收紫外线的季铵化聚硅氧烷以进行性能比较:
化合物1:
化合物2:
化合物3:
使用本发明化合物1、2和3的头发处理组合物的制备和研究:
以标准化的方式通过烫发处理和漂白处理对用于感觉测试的发束进行预先损伤用以进行性能评价。为此,使用通常用于造型的产品。
材料:
·烫发液(例如,Wella的″ondi″)
·中和剂(例如,Wella的″neutrafix″)
·漂白粉(例如,Wella的″blondor special″)
·H2O2(例如,Wella的″Welloxyd 9%″)
·不含护理成分的洗发香波(例如,月桂基醚硫酸钠(12%WAS),NaCI增稠的)
·烧杯
·头发染色刷
按照下列顺序进行处理:
1.烫发处理:
用烫发液润湿发束(头发∶烫发液重量比为1∶2)。室温下在带盖的烧杯内接触15分钟后,小心漂洗2分钟以洗去烫发液。然后使用毛巾轻柔地挤压发束。
在室温下让中和剂(头发∶液体比为1∶2)与发束接触10分钟。然后小心漂洗2分钟以洗去中和剂。之后在室温下干燥头发过夜。
2.漂白处理:
对漂白粉和H2O2进行加工以得到糊剂(粉末∶H2O2的重量比为2∶3)。然后立即用刷子将糊剂涂覆在烫过的头发上。在室温下接触30分钟。然后用流水漂洗2分钟去除漂白糊剂。
之后用不含护发剂的洗发香波洗涤头发1分钟(洗发香波的量:0.5ml/发束),然后漂洗1分钟。
在将预先损伤的发束用于感觉测试之前,在室温下将其干燥过夜。
测试组合物:
用下列组合物进行简单的头发漂洗来测试各护发产品:
产品 | 重量份 |
TEGINACIDCCeteareth-25 | 0.5% |
TEGOalkanol 16十六醇 | 2.0% |
护发剂 | 2.0% |
水 | 加至100% |
柠檬酸 | 加至pH 4.0±0.3 |
″护发剂″指的是本发明的化合物实例或者对照产品。
用护发剂样品对预先损伤的发束进行标准化处理:
对上述预先损坏的发束用上述护发漂洗液进行如下处理:
在流动的温水下润湿发束。用手将过量的水轻柔地挤出,然后施加漂洗液并将其轻柔地揉入头发中(1ml/发束(2g))。经过1分钟的停留时间后,将头发漂洗1分钟。
在感觉测试之前,在50%的大气湿度和25℃的气温下将头发晾干至少12小时。
评价标准:
按照1-5的等级进行感觉评估,1为最差的评价,5为最好的评价。
湿润梳理性:
评价 | 梳子的齿 | 结果 |
5 | 粗 | 没有结,头发可以轻易解开缠结 |
细密 | 非常容易梳理,感觉不到阻力 | |
4 | 粗 | 个别结,头发可以轻易解开缠结 |
细密 | 易于梳理,感觉到轻微阻力 | |
3 | 粗 | 少数结,轻微阻力 |
细密 | 感觉到一定程度的阻力,在反复梳理后降低 | |
2 | 粗 | 一些结,明显阻力 |
细密 | 明显阻力,在反复梳理后不减少 | |
1 | 粗 | 许多结,严重的阻力 |
细密 | 非常严重的阻力,有时不能梳通头发 |
湿润触感:
评价 | 结果 |
5 | 非常光滑、柔软,但仍然美丽强韧、触感良好、不油/粘(无可检测到的残余物) |
4 | 光滑和柔软和/或仅仅检测到少量残余物 |
3 | 光滑、有点硬和/或可检测到一些残余物 |
2 | 硬和/或明显油滑、蜡状残余物 |
1 | 非常硬、不光滑、粗糙和/或极其油、粘(可明确检测到油脂、可检测到蜡状残余物) |
干燥梳理性:
评价 | 梳子的齿 | 结果 |
5 | 粗 | 没有结,头发可以轻易解开缠结 |
细密 | 非常容易梳理,感觉不到阻力,头发不带电 | |
4 | 粗 | 个别结,头发可以轻易解开缠结 |
细密 | 易于梳理,感觉不到阻力,头发变得最小程度地带电 | |
3 | 粗 | 少数结,轻微阻力 |
细密 | 感觉到一定程度的阻力,在反复梳理后减小,头发变得轻微带电 | |
2 | 粗 | 一些结,明显阻力 |
细密 | 明显阻力,在反复梳理后不减小,头发变得带电 | |
1 | 粗 | 许多结,严重的阻力 |
细密 | 非常严重的阻力,有时不能梳通头发,头发变得大量带电 |
干燥触感:
评价 | 结果 |
5 | 非常光滑、柔软,但是仍然强韧、饱满,触感良好 |
4 | 光滑和柔软 |
3 | 光滑、有点硬和/或轻微粗糙(残余物) |
2 | 硬、有些粗糙 |
1 | 不光滑、硬、干燥、粗糙(残余物) |
干燥外观:
评价 | 结果 |
5 | 非常有光泽 |
4 | 有光泽 |
3 | 有些光泽 |
2 | 略有光泽,轻微粗糙 |
1 | 粗糙,无光泽 |
下面的表1比较了如上所述实施的用本发明物质或对照剂处理的发束的感觉测试结果。
头发颜色的耐光性:
为了确定头发颜色的耐光性,使用了染色的发束。为了进行染色,使用了标准的市售产品一Viva牌shade Grenadine Level 2(Wella AG,Darmstadt)。在用头发漂洗液处理之前首先确定各个发束的颜色。处理之后,用光谱(D65)对应于大部分自然日光的灯照射各个发束。此处的照射剂量相当于北纬50℃处的自然每日剂量的二倍。进行所述处理后,再次测量颜色。根据CIE L′a′b′体系进行颜色测试的评价,得到微分值ΔE。ΔE值考虑了光亮度(lightness)的变化,还考虑了红-绿色标和蓝-黄色标的变化。较低的ΔE值表示颜色变化较小。
表1:
″简单的头发漂洗剂″组合物,其含有 | 湿润梳理性 | 湿润触感 | 干燥梳理性 | 干燥触感 | 光泽 | 颜色变化ΔE |
本发明化合物1 | 4.5 | 4.0 | 3.5 | 4.0 | 3.75 | 2.3 |
本发明化合物2 | 4.5 | 3.75 | 3.25 | 4.25 | 3.75 | 1.9 |
本发明化合物3 | 4.5 | 4.25 | 3.5 | 4.25 | 4.0 | 1.1 |
对比化合物十六烷基三甲基氯化铵 | 5.0 | 4.25 | 4.0 | 3.75 | 3.0 | 5.9 |
不含护理剂的对照 | 1.25 | 1.75 | 2.25 | 2.75 | 3.25 | n.d. |
n.d.=未确定
很明显,根据本发明的化合物实例在感觉评价中得到了非常好的化妆品评定。
至于颜色变化,与对比化合物相比,使用本发明化合物观察到显著低的数值。
Claims (10)
1.一种具有通式(I)的吸收紫外线的季铵化聚硅氧烷
其中,基团
R1为相同或不同,并且在每种情况下为具有1-22、优选1-4个碳原子的烷基,或者苯基,
R2可以有一部分具有基团R1的含义,而其它的R2基团彼此独立地为式(Ia或Ib)的基团
R2=-M-S (Ia)
或者
R2=-M-Z+A- (Ib)
条件是在平均分子中,至少两个R2基团各自为式-M-S和-M-Z+A-的基团,
其中
S为决定紫外线吸收的单价生色团,
以及
Z+为式(Id)的基团
R6、R7为具有1-22个碳原子的烷基,或者具有2-22个碳原子的烯基,其中所述烷基或者烯基可以具有羟基,
R9可以为具有1-22个碳原子的单价烃基,或者为决定紫外线吸收的单价生色团,
x=0-6,
y=0或1
并且
M为具有至少4个碳原子的二价烃基,其具有羟基并且可以被一个或多个氧原子中断,
A-为源自常规的生理相容性酸HA的无机或者有机阴离子,
a各自独立地为1-200的值,并且
b为0-10的值。
2.如权利要求1中所述的吸收紫外线的化合物,其中R1可以为甲基、乙基、正丙基、异丙基、正丁基、异丁基或者苯基。
6.如权利要求1-5之一所述的吸收紫外线的化合物,其中Z为相同或不同,并且为选自下列组中的阳离子基团:辛基二甲基胺、月桂基二甲基胺、椰油二甲基胺、十四烷基二甲基胺、十六烷基二甲基胺、硬脂基二甲基胺、山嵛基二甲基胺、油基二甲基胺、辛酰胺基丙基二甲基胺、月桂酰胺基丙基二甲基胺、椰油酰胺基丙基二甲基胺、十四烷酰胺基丙基二甲基胺、棕榈酰胺基丙基二甲基胺、硬脂酰胺基丙基二甲基胺、山嵛酰胺基丙基二甲基胺、油酰胺基丙基二甲基胺、十一碳烯酰胺基丙基二甲基胺、蓖麻酰胺基丙基二甲基胺和胍基丙基二甲基胺。
7.如权利要求1-6之一所述的吸收紫外线的化合物,其中A-为相同或不同,并且为选自下列组中的基团:醋酸根离子、氯离子、溴离子、硫酸氢根离子、硫酸根离子、甲硫酸根离子、乙硫酸根离子、柠檬酸根离子、酒石酸根离子和乳酸根离子,以及芳香酸的阴离子,例如对甲苯磺酸、苯甲酸、水杨酸、肉桂酸、4-甲氧基肉桂酸、4-氨基苯甲酸、4-双(羟基丙基)氨基苯甲酸、4-双(聚乙氧基)氨基苯甲酸、4-二甲基氨基苯甲酸、3-咪唑-4-基丙烯酸、2-苯基苯并咪唑-5-磺酸、3,3’-(1,4-亚苯二次甲基)双(7,7-二甲基-2-氧代双环[2.2.1]庚烷-1-甲磺酸)、2-羟基-4-甲氧基二苯甲酮-5-磺酸和3-(4’-磺基)苄叉莰-2-酮的阴离子。
8.通式(I)的化合物制备吸收紫外线的组合物的应用。
9.通式(I)的化合物在制备用于处理、后处理和保护角蛋白纤维以及皮肤和皮肤附属物的吸收紫外线的组合物中的应用。
10.通式(I)的化合物在制备用于织物处理和后处理的吸收紫外线的洗涤剂和纤维软化剂组合物中的应用。
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DE102005004706A DE102005004706A1 (de) | 2005-02-02 | 2005-02-02 | UV-Licht absorbierende quaternäre Polysiloxane |
DE102005004706.8 | 2005-02-02 |
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EP (1) | EP1688453B1 (zh) |
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CN (1) | CN1814655B (zh) |
AU (1) | AU2006200209B2 (zh) |
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DE (2) | DE102005004706A1 (zh) |
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-
2005
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- 2005-12-15 CA CA2530243A patent/CA2530243C/en not_active Expired - Fee Related
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- 2006-01-20 ES ES06001168T patent/ES2310863T3/es active Active
- 2006-01-20 PL PL06001168T patent/PL1688453T3/pl unknown
- 2006-01-20 DE DE502006001152T patent/DE502006001152D1/de active Active
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101735825A (zh) * | 2008-11-17 | 2010-06-16 | Jsr株式会社 | 液晶取向剂、聚有机硅氧烷、液晶取向膜及其形成方法以及液晶显示元件 |
CN101735825B (zh) * | 2008-11-17 | 2014-01-15 | Jsr株式会社 | 液晶取向剂、聚有机硅氧烷、液晶取向膜及其形成方法以及液晶显示元件 |
CN101862620A (zh) * | 2009-04-16 | 2010-10-20 | 赢创高施米特有限公司 | 包含丙三醇-改性的有机聚硅氧烷的乳化剂 |
CN101862620B (zh) * | 2009-04-16 | 2014-06-11 | 赢创高施米特有限公司 | 包含丙三醇-改性的有机聚硅氧烷的乳化剂 |
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US7776989B2 (en) | 2010-08-17 |
US20060188456A1 (en) | 2006-08-24 |
AU2006200209B2 (en) | 2010-09-02 |
DE102005004706A1 (de) | 2006-08-10 |
ES2310863T3 (es) | 2009-01-16 |
JP2006213920A (ja) | 2006-08-17 |
EP1688453B1 (de) | 2008-07-23 |
PL1688453T3 (pl) | 2009-01-30 |
CA2530243A1 (en) | 2006-08-02 |
CA2530243C (en) | 2012-11-06 |
AU2006200209A1 (en) | 2006-08-17 |
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EP1688453A1 (de) | 2006-08-09 |
DE502006001152D1 (de) | 2008-09-04 |
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