CN101535414A - 片形的新2，9-二氯喹吖啶酮 - Google Patents
片形的新2，9-二氯喹吖啶酮 Download PDFInfo
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- CN101535414A CN101535414A CNA2007800415084A CN200780041508A CN101535414A CN 101535414 A CN101535414 A CN 101535414A CN A2007800415084 A CNA2007800415084 A CN A2007800415084A CN 200780041508 A CN200780041508 A CN 200780041508A CN 101535414 A CN101535414 A CN 101535414A
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- CN
- China
- Prior art keywords
- pigment
- dichloro quinacridone
- oil
- quinacridone
- dichloro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- XPZQBGDNVOHQIS-UHFFFAOYSA-N 2,9-dichloro-5,12-dihydroquinolino[2,3-b]acridine-7,14-dione Chemical compound N1C2=CC=C(Cl)C=C2C(=O)C2=C1C=C(C(=O)C=1C(=CC=C(C=1)Cl)N1)C1=C2 XPZQBGDNVOHQIS-UHFFFAOYSA-N 0.000 title abstract description 14
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- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 17
- 239000003513 alkali Substances 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 12
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- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 claims description 6
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- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical group CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
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Abstract
本发明涉及片形的新2，9－二氯喹吖啶酮，它的制备方法和它用于着色高分子量有机材料的用途。片形的2，9－二氯喹吖啶酮具有1－45μm的长度，0.1－20μm的宽度和0.01－5μm的平均厚度并且体现特征于在反射中的色调值h是≤31和/或在透射中的亮度L*是≥20和/或下降的b*值和从照射和观察角度(逆定向反射角)45°/110°(+25°)到45°/90°(+45°)的提高的a*值。
Description
本发明涉及片形的新2，9-二氯喹吖啶酮，它的制备方法和它用于着色高分子量有机材料的用途。
US4,370,270描述了以至少10μm长度和3μm宽度的薄片形式合成的片形β-变体的铜酞菁。当引入到烤漆(stoving varnish)中时，这一颜料提供蓝色金属效果涂饰。
喹吖啶酮，也称为7，14-二氧代-5，7，12，14-四氢喹诺酮并(2，3-b)吖啶酮，是有价值的颜料。许多专利描述了粒度低于1μm的特殊透明或不透明的喹吖啶酮颜料形式。此外，通式
的线性2，9-二氯喹吖啶酮已知是以三种同质多象变体(polymorphicmodification)存在(Chemical Reviews，67，1，1-18(1967))。蓝红色β-变体具有主要的商业利益。
一般已知的是，热稳定的有机颜料在高温下升华。通过将2，9-二氯喹吖啶酮粉末加热到高于350℃的温度，具有2-3μm厚度和50-150μm长度的层状结构的尺寸过大的薄晶体进行生长并且它们的形成已进行科学讨论(Farbe und Lack，77，8，759-769(1971))
EP0466649公开道，通过在极性溶剂中在长链硫醇化合物和碱的存在下重结晶，已知以具有0.1-5μm粒度的棱形针状颗粒形式存在的粗(crude)2，9-二氯喹吖啶酮能够容易地和有效地转变成具有小片形态的“随角异色效应(effect)”颜料。当被引入到各种涂料体系中时，所得片形据说提供优异的光泽效应。
EP0466649的方法是通过如下来进行的：将粗2，9-二氯喹吖啶酮与脂肪族长链硫醇化合物(如正癸烷硫醇，正十二烷硫醇和叔十二烷硫醇)和碱一起搅拌在极性溶剂(N，N，N’，N’-四甲基脲，N，N-二甲基乙酰胺，N-甲基甲酰胺和优选N，N-二甲基甲酰胺)中，然后将混合物加热到高于50℃的温度(优选在回流温度)，一直进行到转化完成为止，这取决于所选择的条件通常为1-24小时。在转变成片形的过程中，水能够以不损害该方法的量存在。根据EP0466649获得的颜料小片具有1-45μm的长度，0.1-20μm的宽度和0.05-5μm的厚度。特别优选的颜料含有至少50％(重量)的1-20μm长度，0.1-7μm宽度和0.5-2.0μm厚度的小片。
现在令人吃惊地发现，已知以具有0.01-5μm粒度的棱形针状颗粒形式存在的粗2，9-二氯喹吖啶酮能够无需使用脂肪族长链硫醇化合物而容易地和有效地转变成具有小片形态的“随角异色效应”颜料。
因此，本发明涉及制备小片和颜料形式的权利要求1的2，9-二氯喹吖啶酮的方法，该方法包括
(a)在升高的温度下在碱存在下将粗2，9-二氯喹吖啶酮分散和部分地溶解在极性溶剂中，
(b)通过添加水和任选地降低温度来使2，9-二氯喹吖啶酮以所需的片形沉淀下来。
制备2，9-二氯喹吖啶酮的片形的新型方法是通过将粗2，9-二氯喹吖啶酮在碱存在下、在升高的温度下分散和部分地溶解在极性溶剂中来进行的。升高的温度指从100℃到溶剂的回流温度之间、尤其从120℃到溶剂的回流温度之间的温度。在该工艺步骤中可存在少量的水。2，9-二氯喹吖啶酮以所希望的片形的沉淀是通过添加水和降低温度来实现的，其中水的添加速度和温度调节是最关键的点。该转变能够在压力下进行，虽然在大气压力下的转变是优选的。还有可能通过非常严格地控制再结晶来获得一种呈现出比在EP0466649中所述的产品有更有角度的片形的2，9-二氯喹吖啶酮，这通过水的添加以及降低温度来实现。在沉积完成之后悬浮液被冷却到室温，过滤，滤液用水洗涤以除去甲醇钠，然后该颜料被干燥。
起始2，9-二氯喹吖啶酮粗产物具有0.01-5μm的粒度的普通商购针状(棱形针状)2，9-二氯喹吖啶酮粗产物。
合适的极性溶剂是N，N，N’，N’-四甲基脲，N，N-二甲基乙酰胺，N-甲基甲酰胺和N，N-二甲基甲酰胺(DMF)和N-甲基-吡咯烷酮(NMP)。N，N-二甲基甲酰胺和N-甲基-吡咯烷酮是优选的和N-甲基-吡咯烷酮是最优选的。溶剂不必要求不含水。在步骤a)中少量水的添加是有利的。
合适的碱是碱金属氢氧化物或甲醇盐。被证明特别适合于这一目的的碱是锂，钠，钾氢氧化物和/或它们的甲醇盐，优选甲醇钠。
粗2，9-二氯喹吖啶酮与水的摩尔比率是1:2到1:20。如果水的量是不足够的，则2，9-二氯喹吖啶酮小片的收率是差的并且形成了不希望有的颜料形式(针形)。
溶剂的量取决于溶剂的极性和碱的用量，即2，9-二氯喹吖啶酮在碱性溶剂中的溶解度。
如果溶剂是NMP，则NMP是以3-30重量份、尤其4-20重量份/每份颜料的量存在和碱例如甲醇钠是以0.01-1.0重量份、尤其0.1-0.8重量份/每份颜料的量存在。
2，9-二氯喹吖啶酮的片形的新型制备方法针对NMP作为溶剂来更详细地举例说明，但是不限于NMP。
碱(尤其甲醇钠)与NMP在室温下混合。发现有利的是在将针状2，9-二氯喹吖啶酮粗产物添加到NMP和甲醇钠的混合物中之前添加少量的水。然后混合物被加热至在约170℃到NMP的回流温度之间的温度，并在这一温度下搅拌0.25-8小时。水在1-3小时内非常缓慢地添加，因此混合物的温度下降。在约130℃时，所希望的片形的2，9-二氯喹吖啶酮沉积下来。在沉积完成之后悬浮液被冷却到室温，过滤，滤液用水洗涤以除去甲醇钠，然后该颜料被干燥。
2，9-二氯喹吖啶酮以所希望的片形的沉淀是通过添加水和降低温度来实现的，其中水的添加速度和温度调节是最关键的点。通常，由所添加的水实现足够的温度下降，但任选地，加热能够减少。
粗2，9-二氯喹吖啶酮与水的摩尔比率是1:2到1:20。如果水的量是不足够的，则2，9-二氯喹吖啶酮小片的收率是差的并且形成了不希望有的颜料形式(针形)。
颜料、碱和溶剂的量与在步骤a)中使用的温度本质性地相关，因此与粗2，9-二氯喹吖啶酮在碱和溶剂的混合物中的溶解度相关。NMP一般是以3-30重量份、尤其4-20重量份/每份颜料的量存在和碱一般是以0.01-1.0重量份、尤其0.1-0.8重量份/每份颜料的量存在。
根据本发明可获得的片形的2，9-二氯喹吖啶酮具有1-45μm的长度，0.1-20μm的宽度和0.01-5μm、尤其0.03μm到<2μm，非常尤其0.03-0.200μm的平均厚度。该2，9-二氯喹吖啶酮不含C6-C18硫醇化合物。
特别优选的颜料含有至少50％(重量)的1-20μm长度，0.1-7μm宽度和0.05-0.200μm厚度的小片。
如果按照在应用实施例1中所举例说明的那样被引入到0.4mm卷绕PVC片材中，则根据本发明可获得的片形的2，9-二氯喹吖啶酮(1.0％颜料)体现特征于
-在反射(remission)中的色调值h是≤31，
-在透射(transmission)中的色调值h是≥351.0，和/或
-在透射中的亮度L*是≥20，如果在Leneta B & W之上的MinoltaCM3610d上测量色彩。在优选的实施方案中，在透射中的色饱和度C*是≥50。
另外，本发明的2，9-二氯喹吖啶酮的b*值减少和本发明的2，9-二氯喹吖啶酮的a*值是相同的或从照射和观察角度(逆定向反射角度(aspecular angle))45°/110°(+25°)提高到45°/90°(+45°)。在本发明的优选实施方案中，本发明的2，9-二氯喹吖啶酮的b*值减少和本发明的2，9-二氯喹吖啶酮的a*值从照射和观察角度(逆定向反射角度)45°/110°(+25°)提高到45°/90°(+45°)再提高到45°/60°(+75°)。该“角度依赖”测量是通过使用Datacolor FX 10和Black Leneta cards来进行的。尽管EP0466649的实施例1的2，9-二氯喹吖啶酮的b*值也从照射和观察角度(逆定向反射角度)45°/110°(+25°)减少到45°/90°(+45°)，但是它的a*值从照射和观察角度(逆定向反射角度)45°/110°(+25°)下降到45°/90°(+45°)。该差异会给人一种印象，本发明的2，9-二氯喹吖啶酮具有更深/更宽的色变。
根据本发明可获得的片形的2，9-二氯喹吖啶酮与EP0466649的产品之间的区别在于它具有较低的遮盖力(较高的透明度)和显示(更)闪耀发光。另外，它体现特征于它透明、有角度的片形，使得有新的色彩效果，它的角度依赖性的色变和它的X射线衍射图。参考图1-3。
图1是在实施例1中获得的片形的2，9-二氯喹吖啶酮的显微照片。
图2显示了两种颜料在CIELAB色空间中的角度依赖性色变：
a)在EP0466649的实施例1中获得的片形的2，9-二氯喹吖啶酮，
b)在本发明的实施例1中获得的片形的2，9-二氯喹吖啶酮。
图3是在本发明的实施例1中获得的片形的2，9-二氯喹吖啶酮的X射线衍射图，其中x-坐标表示2θ双掠射角和y-坐标表示强度。对于本发明的片形的2，9-二氯喹吖啶酮来说典型的是，在约16.2处的峰在高度上等于或大于分别在约15.5和16.8处的峰。
本发明的生产方法有可能以简单方式可再现性地生产更有角度的片形的2，9-二氯喹吖啶酮小片。本发明的2，9-二氯喹吖啶酮小片呈现特定的形状、侧视色效应(color flop effect)和在反射和/或透射中的不同颜色，和当被引入到塑料中时并容易分散。
本发明的2，9-二氯喹吖啶酮小片特别可用于许多目的，如着色塑料，玻璃，陶瓷产品，装饰性的化妆制品以及尤其涂料和油墨，其中包括印刷油墨，包括防伪印刷油墨(security printing ink)。全部工业上通常的印刷方法是合适的，例如丝网印刷，凹版印刷，铜金粉印刷(bronze printing)，橡胶版轮转印刷和胶版印刷。
对于这些应用，本发明的颜料也理想地与透明和遮盖性白色、彩色和黑色颜料，以及普通的以涂有金属氧化物的云母为基础的发光颜料，金属颜料和已知的(随角异色(goniochromatic))发光颜料掺混使用。
根据本发明的颜料能够用于全部通常的目的，例如用于总体上(in the mass)着色聚合物，表面涂层(包括光效应涂饰，其中包括汽车领域的那些)和印刷油墨在内，以及，例如，用于化妆品。此类应用可从参考资料，例如“Industrielle Organische Pigmente”中获知(W.Herbst and K.Hunger，VCH Verlagsgesellschaft mbH，Weinheim/New York，2nd，completely revised edition，1995)。
根据本发明的颜料或颜料组合物用于着色的高分子量有机材料可以是天然来源或合成来源。高分子量有机材料通常具有约103到108g/mol或甚至更高的分子量。它们可以是，例如天然树脂，干性油，橡胶或酪蛋白，或从其衍生的天然物质，如氯化橡胶，油改性醇酸树脂，粘胶，纤维素醚或酯，如乙基纤维素，乙酸纤维素，丙酸纤维素，乙酰丁酸纤维素或硝化纤维素，但尤其通过聚合、缩聚或加聚所获得的完全合成的有机聚合物(热固性塑料和热塑性塑料)。在聚合树脂的类型当中可以提到，尤其，聚烯烃如聚乙烯，聚丙烯或聚异丁烯，以及取代的聚烯烃，如氯乙烯、乙酸乙烯酯、苯乙烯、丙烯腈、丙烯酸酯、甲基丙烯酸酯或丁二烯的聚合产物，以及此类单体的共聚合产物，如尤其ABS或EVA。
在一系列的加聚树脂和缩聚树脂中可以提到，例如甲醛与苯酚的缩合产物，所谓的酚醛塑料，和甲醛与尿素、硫脲或三聚氰胺的缩合产物，所谓的氨基塑料，和用作表面涂料树脂的聚酯，它是饱和的，如醇酸树脂，或不饱和的，如马来酸树脂；以及线性聚酯和聚酰胺，聚氨酯或聚硅氧烷。
这些高分子化合物能够以单种或以多种的混合物作为塑料物料或塑料熔体形式存在。它们也能够以它们的单体形式存在或在已聚合状态下以溶解形式作为表面涂层或印刷油墨的成膜剂或粘结剂存在，例如熟亚麻仁油，硝化纤维，醇酸树脂，三聚氰胺树脂和脲-甲醛树脂或丙烯酸树脂。
取决于预期的目的，已证明有利的是将根据本发明的颜料或颜料组合物用作调色剂或以制剂的形式使用。取决于调理方法或预期的应用，有利的是在调理过程之前或之后将一定量的质感改进剂(texture-improving agent)添加到颜料中，前提条件是这对于随角异色效应颜料用于着色高分子量有机材料(尤其聚乙烯)的用途没有不利影响。合适的试剂是，尤其，含有至少18个碳原子的脂肪酸，例如硬脂酸或山俞酸，或它们的酰胺或金属盐，尤其镁盐，以及增塑剂，蜡，树脂酸，如松香酸，松香皂，烷基酚或脂族醇，如硬脂醇，或含有8-22个碳原子的脂肪族1，2-二羟基化合物，如1，2-十二烷二醇，以及改性松香马来酸树脂或富马酸松香树脂。该质感改进剂是以基于最终产品的优选0.1-30wt％，尤其2-15wt％的量添加。
根据本发明的颜料能够按照任何着色有效量被添加到要用颜料着色的高分子量有机材料中。包括高分子量有机材料和0.01-80wt％、优选0.1-30wt％(基于高分子量有机材料)的本发明颜料的颜料着色的物质组合物是有利的。1-20wt％，尤其约10wt％，的浓度能够常常用于实践中。
高浓度，例如高于30wt％的那些，通常是以浓缩物(“母料”)形式使用，它们能够用作为了生产具有较低颜料含量的用颜料着色的材料所需要的着色剂，根据本发明的颜料在通常的配制剂中具有格外低的粘度，因此它们能够仍然很好地加工。
为了着色有机材料，根据本发明的颜料能够以单种使用。为了获得不同的色调或色彩效果，除了根据本发明的随角异色效应颜料之外，还有可能将任何所需量的其它着色成分如白色、彩色、黑色或随角异色效应颜料添加到高分子量有机物质中。当彩色颜料与根据本发明的随角异色效应颜料掺混使用时，总量优选是基于高分子量有机材料的0.1-10wt％。
高分子量有机物质用根据本发明的颜料的着色例如通过使用滚压机或混合或研磨设备将该颜料(若合适的话，以母料的形式)与基材掺混来进行。用颜料着色的材料然后通过使用本身已知的方法如压延、压塑、挤出、涂覆、倾注或注塑法被制成所希望的最终形式。在塑料工业中常用的任何添加剂如增塑剂、填料或稳定剂能够在颜料的引入之前或之后以常规量被添加到聚合物中。尤其，为了生产非硬质成形制品或降低它们的脆性，希望在成形之前将增塑剂，例如磷酸、邻苯二甲酸或癸二酸的酯类，添加到高分子化合物中。2，9-二氯喹吖啶酮小片和有机颜料能够在涂漆体系的同一层中存在，但是增强的随角异色效应能够在三层体系中实现，其中有机颜料包含在底涂层中和2，9-二氯喹吖啶酮小片包含在底涂层和透明涂层之间的中间涂层中。
为了着色表面涂料和印刷油墨，该高分子量有机材料和本发明的颜料，若合适的话与通常的添加剂如填料、其它颜料、干燥剂或增塑剂一起，被精细地分散或溶于相同的有机溶剂或溶剂混合物中，有可能让各组分单独溶解或分散或让几种组分一起溶解或分散和仅仅在以后将全部组分混合在一起。
将本发明的颜料分散在需要用颜料着色的高分子量有机材料中和加工本发明的颜料组合物优选是在某些条件下进行，在这些条件下仅仅有较弱的剪切力发生，这样随角异色效应颜料不至于破裂成较小部分。
例如在塑料、表面涂层或印刷油墨中，特别在表面涂层或印刷油墨中，更特别是在表面涂层中获得的着色突出表现于优异的性能，尤其当用于塑料中时极高的饱和度，突出牢度性能，角度依赖性色变(侧视色)和在反射和透射中的不同颜色。
当需要用颜料着色的高分子量物质是表面涂层时，它尤其是专业表面涂料，特别是汽车涂饰漆。
归因于它的不可复制的光学效应，根据本发明的颜料有利地用于从纸和塑料生产防伪材料。术语从纸制造的防伪材料是指，例如，有价证券，如钞票，支票，纳税印花，邮票，铁路与航空票，彩票，礼券，通行卡，表单和股票。术语从塑料制造的防伪材料是指例如支票卡，信用卡，电话卡和身份证。为了获得最佳的光学效应，在加工过程中应该确保小片形颜料是良好取向的，即尽可能与各自介质的表面平行来定向排列。颜料颗粒的这一平行取向最好是从流水作业中进行，并且一般是在塑料加工、涂漆、涂覆涂料和印刷的全部已知方法中实现。
根据本发明的颜料也适合于化妆口唇或皮肤和用于着色头发或指甲。
本发明相应地涉及包括0.0001-90wt％的本发明颜料和10-99.9999wt％的化妆品用合适载体材料的化妆品制剂或配制剂，基于化妆品制剂或配制剂的总重量。
此类化妆品制剂或配制剂例如是口红，腮红，粉底，指甲油和洗发剂。
这些颜料能够以单种或以混合物形式使用。另外，还有可能将本发明的颜料与其它颜料和/或着色剂一起使用，例如作为前面所述或在化妆品制剂中已知的结合物。
根据本发明的化妆品制剂和配制剂优选含有0.005-50wt％的本发明颜料，以制剂的总重量为基础。
用于本发明的化妆品制剂和配制剂中的合适载体材料包括在此类组合物中常用的材料。
根据本发明的化妆品制剂和配制剂可以是，例如，棒，软膏，霜剂，乳液，悬浮液，分散体，粉末或溶液剂的形式。它们例如是口红，睫毛油制剂，腮红，眼影膏，粉底，眼线膏，粉末或指甲油。
如果制剂是棒形，例如口红、眼影膏、腮红或粉底，则这些制剂由较大量的脂肪组分组成，它可以由一种或多种蜡组成，例如地蜡，羊毛脂，羊毛脂醇，氢化羊毛脂，乙酰化羊毛脂，羊毛脂蜡，蜂蜡，小烛树蜡，微晶蜡，巴西棕榈蜡，十六烷醇，硬脂醇，可可脂，羊毛脂脂肪酸，矿脂，石油膏，在25℃下为固体的单-、二-或三-酸甘油酯或其脂肪酸酯，硅酮蜡，如甲基十八烷-氧基聚硅氧烷和聚(二甲基甲硅氧基)硬脂酰氧基硅氧烷，硬脂酸单乙醇胺，松香和它的衍生物，如甘醇松香酸酯和甘油松香酸酯，在25℃下为固体的氢化油，糖甘油酯以及钙、镁、锆和铝的油酸酯，肉豆蔻酸酯，羊毛脂酸酯，硬脂酸酯和二羟基硬脂酸酯。
该脂肪组分也可由至少一种蜡和至少一种油的混合物组成，在这种情况下下列油例如是合适的：石蜡油，purcelline油，全氢化角鲨烯，甜杏仁油，鳄梨油，胡桐油，蓖麻油，芝麻油，霍霍巴油，沸点约310℃到410℃的矿物油，聚硅氧烷油如二甲聚硅氧烷，亚油基醇，亚麻醇，油醇，谷粒油(如麦胚油)，羊毛脂酸异丙酯，棕榈酸异丙酯，肉豆蔻酸异丙酯，豆蔻酸丁酯，肉豆蔻酸十六烷基酯，硬脂酸十六烷基酯，硬脂酸丁基酯，油酸癸基酯，乙酰基甘油酯，醇和多元醇(例如甘醇和甘油)的辛酸酯和癸酸酯，醇和多元醇(例如十六烷醇，异硬脂醇)的蓖麻醇酸酯，羊毛脂酸异十六烷基酯，己二酸异丙基酯，月桂酸己基酯和辛基十二烷醇。
在棒形的制剂中的脂肪组分一般占制剂总重量的至多99.91wt％。
根据本发明的化妆品制剂和配制剂能够另外包括其它成分，例如二醇类(glycols)，聚乙二醇，聚丙二醇，单链烷醇酰胺，非着色的聚合物、无机物或有机物填料，防腐剂，UV过滤剂或在化妆品中常用的其它助剂和添加剂，例如天然的或合成的或部分合成的二-或三-酸甘油酯，矿物油，硅油，蜡，脂肪醇，格尔伯特醇或它的酯，亲油性官能化化妆品活性成分(其中包括防晒过滤剂)，或此类物质的混合物。
适合于皮肤化妆品、活性成分组合物或活性成分提取物的亲油性官能化化妆品活性成分是被批准用于皮肤或局部施用的成分或各种成分的混合物。下列作为例子来提及：
-在皮肤表面和头发上具有清洗作用的活性成分；这些包括用于清洗皮肤的全部物质，如油，皂，合成洗涤剂和固态物质；
-具有脱臭和抑制排汗作用的活性成分：它们包括以铝盐或锌盐为基础的止汗药，包括杀菌或抑菌的脱臭用物质(例如三氯生，六氯酚，醇类)的除臭剂和阳离子物质，例如季铵盐，和气味吸收剂，例如(蓖麻醇酸锌和各种添加剂的结合物)或柠檬酸三乙酯(任选与抗氧化剂例如丁基羟基甲苯相结合)或离子交换树脂；
-提供对太阳光的防护作用(UV过滤剂)的活性成分：合适的活性成分是能够吸收来自太阳光的UV辐射线并将它转化成热量的过滤物质(防晒剂)；取决于预期的作用，下列光防护剂是优选的：选择性地吸收在约280-315nm范围内的引起晒伤的高能UV辐射线并输出例如315-400nm(UV-A范围)的更长波长范围的光防护剂(UV-B吸收剂)，以及仅仅吸收315-400nm的UV-A范围的较长波长辐射的光防护剂(UV-A吸收剂)；
合适的光防护剂例如是选自以下类型中的有机UV吸收剂：对-氨基苯甲酸衍生物，水杨酸衍生物，二苯甲酮衍生物，二苯甲酰基甲烷衍生物，二苯基丙烯酸酯衍生物，苯并呋喃衍生物，包括一个或多个有机硅基团的聚合物UV吸收剂，肉桂酸衍生物，莰酮衍生物，三苯胺基-s-三嗪衍生物，苯基苯并咪唑磺酸和它的盐，邻氨基苯甲酸薄荷基酯，苯并三唑衍生物，和/选自涂有氧化铝或二氧化硅的TiO2，氧化锌或云母的无机微细颜料；
-防止昆虫的活性成分(驱虫剂)是用于防止昆虫接触到皮肤并在皮肤上表现活性的试剂；它们驱赶昆虫并且慢慢地蒸发；最常用的驱虫剂是二乙基甲苯酰胺(DEET)；其它常用的驱虫剂例如见于：“Pflegekosmetik”(W.Raab and U.Kindl，Gustav-Fischer-VerlagStuttgart/New York，1991)，第161页；
-防化学品和机械影响的活性成分：这些包括在皮肤和外部有害物质之间形成阻隔层的全部物质，例如链烷烃油，聚硅氧烷油，植物油，PCL产品和防止水溶液影响的羊毛脂，成膜剂，如海藻酸钠，三乙醇胺藻酸盐，聚丙烯酸盐，聚乙烯醇或防止有机溶剂的作用的纤维素醚，或作为防止在皮肤上造成严重机械应力的＂润滑剂＂的以矿物油、植物油或聚硅氧烷油为基础的物质；
-润湿用物质：下列物质例如用作水分控制剂(润湿剂)：乳酸钠，脲，醇类，山梨糖醇，甘油，丙二醇，胶原，弹性蛋白和透明质酸；
-具有角膜成形作用的活性成分：过氧化苯甲酰，视黄酸，胶态硫和间苯二酚；
-抗微生物剂，例如三氯生或季铵化合物；
-施涂在皮肤上的油性或油溶性维生素类或维生素类衍生物：例如维生素A(游离酸或它的衍生物形式的视黄醇)，泛酰醇，泛酸，叶酸，和它们的结合物，维生素E(生育酚)，维生素F；必需的脂肪酸；或烟酰胺(烟酸酰胺)；
-基于维生素类的胎盘提取物：尤其包括维生素A，C，E，B1，B2，B6，B12，叶酸和生物素，氨基酸和酶以及微量元素镁，硅，磷，钙，锰，铁或铜的化合物的活性成分组合物；
-皮肤修复复合物：可从双歧杆菌属(biffdus)的钝化和分裂细菌培养物获得；
-植物和植物提取物：例如山菊油，芦荟，须苔藓，常春藤，小荨麻，人参，指甲花，白花春黄菊，万寿菊，迷迭香，鼠尾草，问荆或麝香草；
-动物性提取物：例如王浆，蜂巢蜡胶，蛋白质或胸腺提取物；
-能够施涂在皮肤上的化妆品油：Miglyol 812型的中性油，杏仁油，鳄梨油，巴巴苏油，棉子油，琉璃苣籽油，蓟油，花生油，γ-谷维素，蔷薇果油，大麻籽油，榛子油，黑醋栗油，霍霍巴油，樱核油，鲑鱼油，亚麻子油，玉米仁油，昆士兰果油，杏仁油，月见草油，貂油，橄榄油，美洲山核桃仁油，桃仁油，乳香黄连木油，菜油，大米油，蓖麻油，红花油，芝麻油，大豆油，向日葵油，茶树油，葡萄子油或麦胚油。
棒形的制剂优选是无水的，但在某些情况下可包括一定量的水，然而，水一般不超过化妆品制剂的总重量的40wt％。
如果本发明的化妆品制剂和配制剂是半固体产品的形式，即软膏或霜剂的形式，则它们能够同样地是无水或含水的。此类制剂和配制剂例如是睫毛油，眼线膏，粉底，腮红，眼影膏，或用于处理在眼睛之下的环形部(rings)的组合物。
如果，另一方面，该软膏或霜剂是含水的，则它们尤其是油包水型或水包油型的乳液，它除了包括颜料之外还包括1-98.8wt％的脂肪相，1-98.8wt％的水相和0.2-30wt％的乳化剂。
该软膏和霜剂也可包括其它普通的添加剂，例如芳香剂，抗氧化剂，防腐剂，胶凝剂，UV过滤剂，着色剂，颜料，珠光剂，非着色的聚合物以及无机或有机填料。
如果制剂是粉末的形式，则它们主要是矿物或无机或有机填料的形式，例如滑石，高岭土，淀粉，聚乙烯粉末或聚酰胺粉末，以及助剂如粘结剂，着色剂等等。
该制剂能够同样包括通常在化妆品中使用的各种助剂，如香料，抗氧化剂，防腐剂等等。
如果根据本发明的化妆品制剂和配制剂是指甲油，则它们主要由硝化纤维素和呈现为在溶剂体系中的溶液形式的天然或合成聚合物组成，该溶液还有可能包括其它助剂，例如珠光剂。
在该实施方案中，着色的聚合物是以约0.1-5wt％的量存在。
根据本发明的化妆品制剂和配制剂也可用于染色头发，在这种情况下它们是以由化妆品工业中常用的基础物质和本发明的颜料组成的洗发剂、霜剂或凝胶剂的形式使用。
根据本发明的化妆品制剂和配制剂是按照普通方式制备的，例如通过将各组分混合或搅拌在一起，任选有加热以使混合物熔化。
本发明的各种特征和方面在下面的实施例中进一步举例说明。尽管给出这些实施例是为了让本领域中技术人员知道在本发明的范围内如何操作，但是这些实施例不对本发明的范围构成限定作用，本发明的范围仅仅在权利要求中所定义。除非在下面实施例中和在说明书和权利要求的其它地方另有说明，否则全部的份和百分数是按重量计，温度是摄氏度以及压力是处在或接近大气压。
实施例
通过使用含有1.0wt％的片形的2，9-二氯喹吖啶酮颜料的压制PVC板(0.4mm厚度)，根据DIN 53 775部分7来制备用于测量色调值h，亮度L*和饱和度C*以及遮盖力ΔE*-S/W的分析样品。
遮盖力ΔE*-S/W是根据DIN 55984测量的。
在反射/透射中的全部颜色测定是通过使用Minolta CM 3610d分光光度计(d/8几何结构，包括光泽度，发光体D65，观察者角度10°)和Black & White Leneta cards来进行。全部“角度依赖”测量是通过使用在Black Leneta cards之上的Datacolor FX 10来进行的。参考DataColor，Fx 10，Firmenprospekt：
| 照射和观察角度 | 照射角度1) | 观察角度2)(逆定向反射角) |
| ASTM角度3) | 25° | 170°(-15°) |
| ASTM角度3) | 25° | 140°(+15°) |
| ASTM角度3) | 45° | 150°(-15°) |
| ASTM角度3) | 45° | 120°(+15°) |
| ASTM角度3) | 75° | 120°(-15°) |
| ASTM角度3) | 75° | 90°(+15°) |
| ASTM/DIN角度3) | 45° | 110°(+25°) |
| ASTM/DIN角度3) | 45° | 90°(+45°) |
| ASTM/DIN角度3) | 45° | 60°(+75°) |
| ASTM/DIN角度3) | 45° | 25°(+110°) |
1)在样品表面的平面上的0°(左)至180°(右)。
2)90°垂直于样品表面。
3)用于金属薄片着色的材料的多角度颜色测量的ASTM E2194标准操作规程；DIN 6175-2汽车涂漆的耐受性(Tolerances)-2部分：随角异色涂漆。
通过使用Siemens D500X射线衍射仪(CuKα辐射)根据普通方法测定X射线谱。
实施例1
将10g的粗产物形式的2，9二氯喹吖啶酮以及3.3g的甲醇钠在66ml的N-甲基-吡咯烷酮(NMP)中分散15分钟。在添加0.15ml的水后，混合物被加热至175℃。这一温度保持另外2小时。以后，在90分钟的时间中将25ml的冷水按剂量添加到热的反应中，据此温度慢慢地下降。在约130℃下，全部的颜料以所希望的片形沉淀下来。混合物然后通过使用外部水浴被冷却至室温，然后过滤和干燥。
实施例2
将10g的粗产物形式的2，9二氯喹吖啶酮以及4.3g的甲醇钠在100ml的二甲基甲酰胺(DMF)中分散15分钟。在添加0.25ml的水后，混合物被加热至137℃。这一温度保持另外6小时，据此早已形成小片。以后，在20分钟的时间中将58ml的冷水按剂量添加到热的反应中以完成小片的形成。混合物然后通过使用外部水浴被冷却至室温，然后过滤和干燥。
对比实施例1(EP0466649的实施例1)
装有温度计、搅拌器和冷凝器的1升烧瓶用氮气吹扫，然后加入190ml工业级N，N-二甲基甲酰胺，36ml 1-十二烷硫醇，19.0克粗2，9-二氯喹吖啶酮和8.1克甲醇钠。混合物被搅拌和加热到回流状态，据此颜料几乎完全地溶解得到蓝色的溶液。在8小时的回流时间中，具有青铜色金属外观的2，9-二氯喹吖啶酮小片从溶液中结晶出来。悬浮液被冷却到室温和新的小片颜料由过滤分离。压滤饼用甲醇和然后用水洗涤，并在100℃下干燥获得18.5克的具有下面尺寸的有光泽的颜料：长度3-25μm，宽度1-10μm，厚度0.05-2μm。
应用实施例1
0.4mm辊压PVC片的色调角(色调值)h，亮度L*和色饱和度C*的测量：
-预混合物：
0.4g颜料与14.0g的基础混合物混合30分钟，然后与26.0g的聚氯乙烯(PVC)(EVIPOLSH 7020，EVC GmbH)一起慢慢地搅拌。该基础混合物由增塑剂(12.9g Palatinol10P(邻苯二甲酸二-2-丙基庚基酯，BASF)，0.6g Drapex39(环氧化大豆油，Witco VinylAdditives GmbH)和0.5g Mark BZ561(Crompton Vinyl AdditivesGmbH)组成。
-辊压片材的生产：
由PVC和以上所获得的颜料/基础混合物所组成的混合物在2-辊轧机(Collin model，D-85560Ebersberg)中在160℃的辊温度(各辊)下根据以下条件进行辊压：
a)热辊压6分钟(辊压的片材每一分钟反转过来(turn)，辊隙距0.35mm)。
在实施例1和2和对比实施例1中获得的颜料在PVC膜(1％颜料)中的反射数据给出在下面。
| L* | C* | h | |
| 在实施例1中获得的颜料 | 40.1 | 44.7 | 29.5 |
| 在实施例2中获得的颜料 | 35.0 | 31.0 | 25.8 |
| 在对比实施例1中获得的颜料 | 40.7 | 42.9 | 31.7 |
| CINQUASIA Magenta RT-243-D1) | 30.7 | 27.0 | 15.2 |
| 起始针状颜料粗产物 | 37.4 | 43.5 | 22.9 |
1)可从Ciba Speciality Chemicals商购的针状2，9二氯喹吖啶酮
在实施例1和2和对比实施例1中获得的颜料在PVC膜(1％颜料)中的透射数据给出在下面。
| L* | C* | h | |
| 在实施例1中获得的颜料 | 22.0 | 54.1 | 356.3 |
| 在实施例2中获得的颜料 | 21.6 | 48.1 | 353.3 |
| 在对比实施例1中获得的颜料 | 19.1 | 52.4 | 350.1 |
| CINQUASIA Magenta RT-243-D1) | 24.0 | 60.2 | 11.3 |
| 起始针状颜料粗产物 | 18.3 | 51.8 | 354.8 |
1)可从Ciba Speciality Chemicals商购的针状2，9二氯喹吖啶酮
应用实施例2
以在Black Leneta-cards之上的与应用实施例1中相同的1％PVC-片材为基础，在实施例1和2和对比实施例1中获得的颜料的色彩特性(CIELAB-L*，C*，h；或L*，a*，b*)：
在实施例1中获得的片形的2，9-二氯喹吖啶酮：
| 角度** | L* | C* | H* |
| 25°/170°(-15°) | 38.54 | 10.52 | 22.47 |
| 25°/140°(+15°) | 52.46 | 35.62 | 38.60 |
| 45°/150°(-15°) | 52.03 | 44.32 | 43.75 |
| 45°/120°(+15°) | 50.21 | 49.99 | 43.32 |
| 75°/120°(-15°) | 46.47 | 52.38 | 46.06 |
| 75°/90°(+15°) | 42.48 | 50.08 | 43.33 |
| 45°/110°(+25°) | 37.88 | 56.34 | 41.70 |
| 45°/90°(+45°) | 27.86 | 57.47 | 38.65 |
| 45°/60°(+75°) | 22.89 | 55.95 | 35.18 |
| 45°/25°(+110°) | 21.33 | 53.58 | 33.27 |
| 角度** | L* | a* | b* |
| 25°/170°(-15°) | 38.54 | 09.72 | 04.02 |
| 25°/140°(+15°) | 52.45 | 27.84 | 22.22 |
| 45°/150°(-15°) | 52.03 | 32.02 | 30.65 |
| 45°/120°(+15°) | 50.21 | 36.37 | 34.29 |
| 75°/120°(-15°) | 46.47 | 36.34 | 37.72 |
| 75°/90°(+15°) | 42.48 | 36.43 | 34.37 |
| 45°/110°(+25°) | 37.88 | 42.06 | 37.48 |
| 45°/90°(+45°) | 27.86 | 44.88 | 35.89 |
| 45°/60°(+75°) | 22.89 | 45.73 | 32.24 |
| 45°/25°(+110°) | 21.33 | 44.79 | 29.39 |
在实施例2中获得的片形的2，9-二氯喹吖啶酮：
| 角度** | L* | C* | H* |
| 25°/170°(-15°) | 29.66 | 10.42 | 16.58 |
| 25°/140°(+15°) | 40.97 | 30.97 | 32.04 |
| 45°/150°(-15°) | 41.85 | 37.55 | 37.52 |
| 45°/120°(+15°) | 39.12 | 41.77 | 37.87 |
| 75°/120°(-15°) | 37.85 | 42.95 | 41.00 |
| 75°/90°(+15°) | 32.90 | 41.82 | 39.07 |
| 45°/110°(+25°) | 29.27 | 47.16 | 39.49 |
| 45°/90°(+45°) | 21.66 | 45.75 | 36.58 |
| 45°/60°(+75°) | 18.09 | 43.23 | 33.19 |
| 45°/25°(+110°) | 16.84 | 40.73 | 30.88 |
| 角度** | L* | a* | b* |
| 25°/170°(-15°) | 29.66 | 09.98 | 02.97 |
| 25°/140°(+15°) | 40.97 | 26.26 | 16.43 |
| 45°/150°(-15°) | 41.85 | 29.78 | 22.87 |
| 45°/120°(+15°) | 39.12 | 32.97 | 25.64 |
| 75°/120°(-15°) | 37.85 | 32.41 | 28.18 |
| 75°/90°(+15°) | 32.90 | 32.47 | 26.36 |
| 45°/110°(+25°) | 29.27 | 36.39 | 29.99 |
| 45°/90°(+45°) | 21.66 | 36.74 | 27.27 |
| 45°/60°(+75°) | 18.09 | 36.18 | 23.66 |
| 45°/25°(+110°) | 16.84 | 34.95 | 20.90 |
在对比实施例1中获得的片形的2，9-二氯喹吖啶酮：
| 角度** | L* | C* | H* |
| 25°/170°(-15°) | 40.57 | 13.43 | 19.83 |
| 25°/140°(+15°) | 54.44 | 44.09 | 37.09 |
| 45°/150°(-15°) | 56.46 | 51.04 | 39.95 |
| 45°/120°(+15°) | 54.17 | 58.63 | 41.83 |
| 75°/120°(-15°) | 52.75 | 58.49 | 42.88 |
| 75°/90°(+15°) | 47.54 | 57.82 | 43.06 |
| 45°/110°(+25°) | 43.45 | 61.89 | 42.69 |
| 45°/90°(+45°) | 29.65 | 57.76 | 40.43 |
| 45°/60°(+75°) | 20.12 | 50.62 | 35.61 |
| 45°/25°(+110°) | 17.19 | 45.71 | 31.67 |
| 角度** | L* | a* | b* |
| 25°/170°(-15°) | 40.57 | 12.63 | 04.56 |
| 25°/140°(+15°) | 54.44 | 35.17 | 26.59 |
| 45°/150°(-15°) | 56.46 | 39.13 | 32.77 |
| 45°/120°(+15°) | 54.17 | 43.68 | 39.10 |
| 75°/120°(-15°) | 52.75 | 42.86 | 39.80 |
| 75°/90°(+15°) | 47.54 | 42.24 | 39.48 |
| 45°/110°(+25°) | 43.45 | 45.48 | 41.96 |
| 45°/90°(+45°) | 29.65 | 43.97 | 37.46 |
| 45°/60°(+75°) | 20.12 | 41.07 | 29.42 |
| 45°/25°(+110°) | 17.19 | 38.90 | 24.00 |
**照射角度/观察角度(逆定向反射角)。
Claims (10)
1.具有1-45μm的长度，0.1-20μm的宽度和0.01-5μm、尤其0.03-0.200μm的平均厚度的片形的2，9-二氯喹吖啶酮，其特征在于在反射中的色调值h是≤31和/或在透射中的亮度L*是≥20和/或下降的b*值和从照射和观察角度(逆定向反射角)45°/110°(+25°)到45°/90°(+45°)的提高的a*值。
2.制备小片和颜料形式的权利要求1的2，9-二氯喹吖啶酮的方法，该方法包括
(a)在升高的温度下在碱存在下将粗2，9-二氯喹吖啶酮分散和部分地溶解在极性溶剂中，
(b)通过添加水和任选地降低温度来使2，9-二氯喹吖啶酮以所需的片形沉淀下来。
3.权利要求2的方法，其中所述碱是碱金属氢氧化物或甲醇盐。
4.权利要求书2或3的方法，其中所述极性溶剂选自N，N，N’，N’-四甲基脲，N，N-二甲基乙酰胺，N-甲基甲酰胺和优选N，N-二甲基甲酰胺(DMF)和N-甲基-吡咯烷酮(NMP)。
5.权利要求4的方法，其中溶剂是N-甲基-吡咯烷酮，它在步骤(a)中被加热至150℃到回流温度之间。
6.权利要求5的方法，其中在步骤(b)中的温度下降到100-120℃。
7.权利要求2的方法，其中粗2，9-二氯喹吖啶酮与水的摩尔比率是1:2-1:20。
8.根据权利要求2-7中任何一项的方法可获得的片形的2，9-二氯喹吖啶酮。
9.含有有效着色量的权利要求1或8的2，9-二氯喹吖啶酮小片的高分子量有机材料。
10.着色高分子量有机材料的方法，该方法包括将有效着色量的权利要求1或9的2，9-二氯喹吖啶酮小片引入到所述有机材料中。
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| AU2010285107A1 (en) | 2009-08-21 | 2012-03-15 | Basf Se | Apparatus and method for a sub microscopic and optically variable image carrying device |
| US9453132B2 (en) | 2009-11-27 | 2016-09-27 | Basf Se | Coating compositions for security elements and holograms |
| KR101821431B1 (ko) | 2010-02-04 | 2018-01-23 | 바스프 에스이 | 개선된 스파클링 효과를 갖는 안료 조성물 |
| EP2723576B1 (en) | 2011-06-21 | 2017-08-09 | Basf Se | Printing diffraction gratings on paper and board |
| RU2508425C2 (ru) * | 2012-04-12 | 2014-02-27 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Санкт-Петербургский государственный университет технологии и дизайна" (СПГУТД) | Состав для печатания текстильных материалов |
| KR20150027205A (ko) | 2012-06-14 | 2015-03-11 | 바스프 에스이 | 보안 요소 및 홀로그램의 제조 방법 |
| CA2883840C (en) | 2012-09-17 | 2021-01-26 | Basf Se | Security elements and method for their manufacture |
| WO2014187750A1 (en) | 2013-05-21 | 2014-11-27 | Basf Se | Security elements and method for their manufacture |
| EP3052701B1 (en) | 2013-10-04 | 2017-06-28 | Basf Se | High gloss metal effect papers |
| CN107429491A (zh) | 2015-03-30 | 2017-12-01 | 巴斯夫欧洲公司 | 高光泽金属效应纸和板 |
| CN110832040A (zh) | 2017-05-15 | 2020-02-21 | 巴斯夫欧洲公司 | 制备金属纳米颗粒层的方法及其在装饰或安全元件中的用途 |
| WO2019016136A1 (en) | 2017-07-20 | 2019-01-24 | Basf Se | TITANIUM DIOXIDE NANOPARTICLES FUNCTIONALIZED ON SURFACE BY PHOSPHONATE |
| EP3658701A1 (en) | 2017-07-28 | 2020-06-03 | Basf Se | Process for the preparation of metallic nano-particle layers and their use for decora-tive or security elements |
| CN111936317A (zh) | 2018-04-25 | 2020-11-13 | 巴斯夫欧洲公司 | 在柔性基材上制备强粘附性(压花)膜的方法 |
| CA3150847A1 (en) | 2019-09-17 | 2021-03-25 | Basf Se | Metal oxide nanoparticles |
| US20230312944A1 (en) | 2020-08-21 | 2023-10-05 | Basf Se | Uv-curable coatings having high refractive index |
| EP4234641A1 (en) | 2022-02-25 | 2023-08-30 | Basf Se | Compositions, comprising modified titanium dioxide nanoparticles and uses thereof |
| WO2023165903A1 (en) | 2022-03-02 | 2023-09-07 | Basf Coatings Gmbh | A water-borne pigment paste composition free of resin, its preparation method and its application thereof |
| WO2024012962A1 (en) | 2022-07-11 | 2024-01-18 | Basf Se | Uv-curable coatings having high refractive index |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3579519A (en) * | 1966-09-08 | 1971-05-18 | Eastman Kodak Co | Crystalline form of quinacridone |
| SU455102A1 (ru) * | 1973-02-19 | 1974-12-30 | Предприятие П/Я В-8611 | Способ получени , -диалкилхинакридонов |
| US4247696A (en) * | 1978-04-01 | 1981-01-27 | Toyo Soda Manufacturing Co., Ltd. | Process for preparing gamma phase quinacridone |
| US5084573A (en) * | 1990-07-13 | 1992-01-28 | Ciba-Geigy Corporation | 2,9-dichloroquinacridone in platelet form |
-
2007
- 2007-10-30 EP EP07822011A patent/EP2079807B1/en not_active Not-in-force
- 2007-10-30 AT AT07822011T patent/ATE483765T1/de not_active IP Right Cessation
- 2007-10-30 CN CNA2007800415084A patent/CN101535414A/zh active Pending
- 2007-10-30 US US12/513,422 patent/US8017778B2/en not_active Expired - Fee Related
- 2007-10-30 DE DE602007009712T patent/DE602007009712D1/de active Active
- 2007-10-30 KR KR1020097011926A patent/KR20090078371A/ko not_active Application Discontinuation
- 2007-10-30 JP JP2009535670A patent/JP2010509417A/ja active Pending
- 2007-10-30 WO PCT/EP2007/061657 patent/WO2008055807A2/en active Application Filing
- 2007-10-30 BR BRPI0718695-9A patent/BRPI0718695A2/pt not_active IP Right Cessation
- 2007-10-30 RU RU2009121645/05A patent/RU2459847C2/ru not_active IP Right Cessation
Also Published As
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|---|---|
| WO2008055807A3 (en) | 2009-01-15 |
| WO2008055807A2 (en) | 2008-05-15 |
| EP2079807A2 (en) | 2009-07-22 |
| RU2459847C2 (ru) | 2012-08-27 |
| KR20090078371A (ko) | 2009-07-17 |
| US20100099877A1 (en) | 2010-04-22 |
| BRPI0718695A2 (pt) | 2013-12-31 |
| DE602007009712D1 (de) | 2010-11-18 |
| EP2079807B1 (en) | 2010-10-06 |
| RU2009121645A (ru) | 2010-12-20 |
| JP2010509417A (ja) | 2010-03-25 |
| ATE483765T1 (de) | 2010-10-15 |
| US8017778B2 (en) | 2011-09-13 |
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