CN100471922C - 紫外固化的抗指纹涂层 - Google Patents
紫外固化的抗指纹涂层 Download PDFInfo
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- CN100471922C CN100471922C CN02817749.5A CN02817749A CN100471922C CN 100471922 C CN100471922 C CN 100471922C CN 02817749 A CN02817749 A CN 02817749A CN 100471922 C CN100471922 C CN 100471922C
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- coating
- methyl
- acrylate
- base material
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Abstract
用于在金属或塑料表面产生薄的耐水解、抗划痕和防污涂层的方法,其中涂料可以直接涂布到清洁的金属表面上,然后通过高能辐射交联,特别是UV辐射。基材可以以带的形式被涂布,然后变成所需的外部形状。被涂布基材如这些不再易于被食物、清洁剂或指纹弄污,并且可以被作成抗菌性。因此,以此方式涂布的物体适于用在建筑中,用于建筑物的内部装备、用于制造家具、以及用于装饰应用,并且特别是用在家居中,用在卫生应用中,用在医院中,以及用于食品处理和制药业中。
Description
本发明涉及用于在金属表面、特别是铝或高级钢表面产生防污功能涂层的方法,以及为此使用的合适涂料。
家居、卫生应用、医院以及食品处理和制药工业中使用大量金属、特别是高级钢或铝制的器具、设备和机械。此时,由于例如高级钢具有高耐蚀性而优选使用。这种钢通常是以抛光或刷过的面并且无其它涂层的方式使用。另外,建筑中也使用大量具有不同组成的金属部件,如在建筑物的内部装备、制家具时以及在装饰应用中使用。在这些应用中,金属表面也通常被抛光、刷过、或设置有表面图案,并且使用时不施加另外的涂层。
这种形式的金属表面非常易于被灰尘、食物或清洁剂沾污,或者被留下指纹。为改善这种表面的抗划痕性或避免沾污已经提出了大量处理金属表面的方法。这些方法包括使用溶剂基和水溶液系统,如水性电泳沉积性浸涂涂料或粉末涂料进行的涂布方法。这些涂料用来改善表面的易沾污性和抗划痕性。该方法的缺点有,例如,固化条件如时间、温度、以及相应的工厂尺寸。另外,要想不破坏表面涂层而形成物件通常是不可能的。
DE 199 57 325和DE 199 52 323记载了金属或塑料用涂料;该涂料是热固性的,并以由有机硅化合物构成的水溶胶为基础。EP 1 036 829涉及金属和导电塑料用UV交联性涂料,但仅记载了水溶液系统,其通过电泳涂布施用到导电基材上,随后首先在高温下干燥,然后在UV光照射下进行后固化。
JP-A-07/171496和JP-A-04/150976(1992)记载了高级钢上的热固性涂层,其由聚酯树脂和硅酸酯树脂或三聚氰胺树脂制成。JP10/228446和EP 0 789 065记载了特殊的UV交联性涂层体系,其基本上用于涂布木材,以20或30μm以上的层厚涂布。
因此,尽管存在有关UV交联性涂料的大量现有技术,但是为避免金属或甚至塑料基材被沾污而以薄的层厚进行涂布的问题还没有解决。就此而言,被涂布表面应具有良好的防沾污性和抗划痕性;另外,应保持尤其是刷过的或结构化的金属表面的自然外观。现有技术中没有讨论这些要求。另外,为能够节约地涂布甚至更大的表面,需要节能、快速和环境友好的涂布方法。另一个要求是应该在不损害涂层的情况下可以得到被涂布的物件。因此,目的是为了满足这些目的提供无溶剂的薄涂层体系,当例如用于家居和商业或者食品加工业时,其防划痕性、耐碱性和酸性清洁剂的能力高。
根据本发明,该目的是通过提供一种无溶剂液体涂料来实现的,这种涂料通过高能辐射发生交联,并且在0~90℃的温度范围内、优选15~70℃内,其粘度低于1000mPas,其含有
a)40~90重量%的低聚、直链或支链环氧(甲基)丙烯酸酯、聚酯(甲基)丙烯酸酯、聚醚(甲基)丙烯酸酯和/或尿烷(甲基)丙烯酸酯的至少一种;
b)5~60重量%、优选10~60重量%的单官能液体(甲基)丙烯酸酯或二、三或多(甲基)丙烯酸酯化合物的至少一种,和
c)0.1~20重量%的含有酸性基团的甲基丙烯酸酯化合物,
d)任选的0~30重量%的含有另外的官能团的二-或三烷氧基硅烷,
d)0.1~20重量%的涂层技术中使用的辅助物质,如粘合促进剂、流动控制剂、消泡剂和/或光稳定剂以及光引发剂。
本发明的涂料优选作为具有薄涂层的金属表面用涂料,所述的薄涂层耐水解和耐清洁剂,并具有防划痕性。本发明还提供本发明涂料的应用,其中涂料被作成抗菌性。
本发明还提供涂布金属表面的方法,其中首先任选将基材清洗和脱脂,然后以层厚0.5~20μm涂布本发明的涂料,最后通过高能辐射将涂层交联。本发明进一步提供涂布那些表面的方法,其中在交联步骤前,在被涂布表面上设置可除去的保持涂膜。
本发明的方法和本发明的涂料特别适合在由铁质材料、钢和合金钢、轻质金属如铝、镁、钛、非铁金属如铜、锌、锡、或贵金属如金、银或其合金构成的表面上使用。该表面可被研磨、刷过、抛光、电化学处理或电解涂布如镀镉、镀铬或镀镍。基材可以是任意形状,但优选板状、带状或卷状。
本发明的涂料含有可聚合的低聚物,其具有不饱和双键,该低聚物如具有侧向或末端(甲基)丙烯酸基的聚酯低聚物或聚醚低聚物、或优选(甲基)丙烯酸酯官能性的脂肪、脂环和/或芳族环氧化物、或具有反应性(甲基)丙烯酸酯基团的聚氨酯低聚物。这些低聚物应具有至少两个不饱和双键官能团并且分子量一般在500~15000之间。它们可以是市售的。其量为40~90重量%,特别是45~85重量%,并且不同低聚物的混合物也是可以的。
涂料也可以含有至少一种单-、二、三、或多官能性不饱和低分子量(甲基)丙烯酸酯,存在单独的化合物或混合物也可以。这种化合物的例子有:任选被烷氧基化的烷烃二醇(甲基)丙烯酸酯或烷烃三醇(甲基)丙烯酸酯,如1,3-丁二醇二(甲基)丙烯酸酯、1,4-丁二醇二(甲基)丙烯酸酯、1,6-己二醇二(甲基)丙烯酸酯、三烷撑二醇二(甲基)丙烯酸酯、聚烷撑二醇二(甲基)丙烯酸酯、四烷撑二醇二(甲基)丙烯酸酯、新戊二醇二(甲基)丙烯酸酯、甘油烷氧基三(甲基)丙烯酸酯、烷氧基化的新戊二醇二(甲基)丙烯酸酯;(甲基)丙烯酸环氧化物如双酚A环氧化物二(甲基)丙烯酸酯;多羟基(甲基)丙烯酸酯,如季戊四醇三(甲基)丙烯酸酯、三羟甲基丙烷三(甲基)丙烯酸酯、三烷氧基-三羟甲基丙烷三(甲基)丙烯酸酯、二(三羟甲基丙烷)四(甲基)丙烯酸酯、季戊四醇四(甲基)丙烯酸酯、三(2-羟基烷基)异氰脲酸酯三(甲基)丙烯酸酯、二季戊四醇四(甲基)丙烯酸酯、二季戊四醇戊(甲基)丙烯酸酯、二季戊四醇六(甲基)丙烯酸酯,其中烷撑指亚乙基、亚丙基或亚丁基,烷氧基指乙氧基、1,2-或1,3-丙氧基或1,4-丁氧基。
以下(甲基)丙烯酸酯是可以使用的单官能团丙烯酸酯化合物:直链、支链或环状烷基(甲基)丙烯酸酯,如正烷基/异烷基(甲基)丙烯酸酯、环己基(甲基)丙烯酸酯、4-叔丁基环己基(甲基)丙烯酸酯、二氢环戊二烯基(甲基)丙烯酸酯、四氢糠基(甲基)丙烯酸酯、异冰片基(甲基)丙烯酸酯、烯丙基(甲基)丙烯酸酯、单(甲基)丙烯酰基烷基邻苯二甲酸酯、琥珀酸酯或马来酸酯;烷烃二醇单(甲基)丙烯酸酯,如羟丙基(甲基)丙烯酸酯、聚烷撑二醇(甲基)丙烯酸酯、单烷氧基三烷撑二醇(甲基)丙烯酸酯、2,3-环氧丙基(甲基)丙烯酸酯;芳族(甲基)丙烯酸酯,如壬基苯酚(甲基)丙烯酸酯、2-苯氧基烷基(甲基)丙烯酸酯;丙烯酰胺,如N,N-二烷基(甲基)丙烯酰胺、N,N-二烷基氨基烷基(甲基)丙烯酰胺。也可以使用一定比例的乙烯基醚,如乙烯基乙基醚、乙烯基丙基醚、乙烯基异丁基醚、乙烯基十二烷基醚、丁二醇-1,4-二乙烯基醚、二乙二醇二乙烯基醚、羟丁基乙烯基醚。单体丙烯酸酯化合物可以单独使用或以混合物形式使用,总量为5~60重量%,特别是15~50重量%。
该涂料也可以含有具有另外的有机官能团的二-或三烷氧基硅烷。其实例有氨丙基三烷氧基硅烷、双(三烷氧基甲硅烷基丙基)胺、羟乙基三烷氧基硅烷、羧基丙基三烷氧基硅烷、乙烯基三烷氧基硅烷,此时的烷氧基是指甲氧基、乙氧基、丙氧基或丁氧基。其量优选为0~15重量%。
优选涂料含有具有酸性基团并具有一个、两个或更多个(甲基)丙烯酸基团、并另外含有酸性官能团的甲基丙烯酸酯化合物。该成分的含量为0.1~20重量%,优选0.5~10重量%。这种酸性官能团的实例有羧基、磷酸基或膦酸基、磺基及其衍生物,例如,酯。特别优选磷酰基。
已知的优选自由基引发剂可以用作光引发剂,如2-苄基二甲基氨基-1-(4-吗啉代苯基)丁酮-1、二苯甲酰二甲基缩酮、或二甲氧基苯基乙酰苯、α-羟基苄基苯基酮、1-羟基-1-甲基乙基苯基酮、低聚-2-羟基-2-甲基-1-(4-(1-甲基乙烯基)苯基)丙酮、二苯甲酮、邻苯甲酰苯甲酸甲酯、苯甲酰甲酸甲酯、2,2-二乙氧基乙酰苯、2,2-二仲丁氧基乙酰苯、对苯基二苯甲酮、2-异丙基噻吨酮、2-甲基蒽醌、2-乙基蒽醌、2-氯蒽醌、1,2-苯并蒽醌、联苯酰、安息香、安息香甲基醚、安息香异丙基醚、α-苯基安息香、噻吨酮、二乙基噻吨酮、1,5-乙酰萘、1-羟基环己基苯基酮、对二甲基氨基苯甲酸乙酯。这些化合物可以单独使用或者以混合物的形式使用,或与其它过氧化物型自由基引发剂或与胺促进剂组合使用。
除上述的粘合剂外,本发明的涂料含有少量其它添加剂,这些添加剂对例如流动性能、成膜、涂料的粘合性或耐性产生有益效果。这些添加剂的例子有流动控制剂如氟化聚硅酮二醇、硅酮二醇、聚醚聚硅氧烷共聚物。已知的基于位阻氨基化合物的试剂也可以用作光稳定剂。
该涂料也可以含有染料、光学增白剂和/或颜料作为添加剂。染料有基于有机染料的那些,其可溶于涂料。这些染料在膜固化后形成有色的透明涂层,并且基材表面产生特殊的视觉效果。光学增白剂为吸收UV辐射并以可见光形式将其再辐射的化合物类型;其可以例如选自三嗪衍生物。颜料是指有机或无机、着色或无色颜料制剂,如氧化铁颜料、二氧化钛颜料、碳黑、喹吖(二)酮或酞菁颜料。这些物质必须均匀分散在涂料中。在这一点上,粒径明显小于目标层厚,优选低于1μm。在将这些成分加到涂料中之前,将其分散在部分液体丙烯酸酯化合物中可能是有利的。
也可以使用微粉化的填料如二氧化硅、氧化铝、二氧化钛或硫酸钡。其为白色的、无色的或不透明的/透明的,并且以细分散的形式使用。根据用量和类型,其可以影响涂层的表面硬度、结构和抗划痕性。辅助物质的用量为0.1~20重量%,优选0.5~15重量%。
另外,在优选实施方案中,该涂料可以含有抗菌或杀生物化合物。这些物质例如有机物质如生物胍、取代的苯扎卤铵(benzalkoniumhalide)、烷基聚乙烯基嘧啶、甜菜碱;或无机物,如银盐或细碎的银粒子,粒径范围为几nm。用量为0.1~5重量%,并且取决于所使用物质的活性。这些化合物加到涂料中,并且在交联反应中不被破坏。其使得表面具有长期抗菌作用。
本发明的涂料的成分可以通过已知方法混合在一起。这里,将固体成分溶解或者在颜料的情况下分散到低粘度成分中可能是有用的。为确保储存稳定性,在特殊反应性成分的情况下,将这些成分加入涂料中之前将其在低粘度成分中预混并限制可能的反应也许是有益的。
本发明的方法可以适于该方法中被涂布的物件。根据其处理条件,对基材施行清洗步骤,共可以通过浸渍、喷涂、高压或注入喷涂、或借助于超声或电解进行。在该过程中,从生产过程中除去尘粒、氧化层、粘着残余物或脂肪/油状物。已知的优选水性清洁剂可以用于清洗过程。清洗过程后,用水冲洗表面,干燥,然后立即进行另外的处理。在用本发明的涂料涂布之前优选不进行另外的预处理;特别地,不施加底层涂料。
通过已知的涂布方法可以用涂料将基材覆盖。如果要涂布成形或异型部件,主要是用于涂布技术中的喷涂系统,如无气、气助或静电辅助喷涂方法是适合的,或者甚至是用刷子手动涂布。特别优选通过注入/挤出、喷涂/挤出、或通过适合的涂刷器或辊涂布将涂料涂布到工件或金属带的水平面上。这里,涂布时涂料的粘度低于1000mPas,优选低于300mPas(在锥/板粘度计中测定)。
涂料的层厚一般为0.5~20μm,特别是1~10μm,特别优选最大为5μm。
涂料一般在0~90℃、优选15~70℃的温度下涂布。然后通过高能辐射如UV辐射、电子辐射或γ-辐射使涂料交联。电子辐射具有150~350keV的能量值。优选交联通过UV辐射实现,特别是波长为150~800nm、特别优选200~450nm的UV。合适的辐射源对于本领域的技术人员是已知的。辐射强度和辐射持续时间取决于处理条件,如辐射源的距离或源与基材间的相对移动。但是,持续时间一般低于60秒,优选0.001~30秒。设备的各变量可以由本领域的技术人员通过简单的调节来确定。
在该方法的特别的实施方案中,被交联的基材上面的区域中的氧含量可以减少。这里,特别低于3000ppm,优选低于1000ppm。这可以通过例如将交联区中存在的环境空气部分或完全变换为惰性气体,如氩、氮气、CO2或其混合物来实现。该方法实施方案的优势在于涂料中所需的光引发剂浓度可以减少。
本发明的另一个实施方案中在涂布涂料后包括另外的步骤,其中首先在基材上施加所使用的高能辐射可透过的膜。可以将这样的膜施加到三维基材上,但优选基材为板或带。施加优选通过机械方法进行;例如,可以由输送辊上取下抗撕裂的膜并通过辊无空隙地施加到基材上。该处理步骤后,通过辐射将膜下的涂料交联。该方法的一个优点是固化在惰性条件下,即特别是排除了氧的条件下在膜下进行。
该膜例如由聚乙烯、聚丙烯、PET或其混合物构成。其是有色的,或者优选为透明的。该膜必须不与涂料反应。其抗撕裂,从而在随后的处理步骤中通过拔取可将其从基材表面上除去。这也可以在终用户的前提下进行,从而膜可以起到在另外的处理和/或输运时保护物件的作用。
应用本发明的涂料得到具有薄表面涂层的被涂布基材,特别是金属型基材。同时,可以获得特别的视觉效果,如金属光泽、消光、结构或着色。根据本发明涂布的物件的优选应用是建筑中使用的金属板、金属零件或异型金属,用于建筑物的内部装备或用于家具制造,以及金属装饰物。特别地,根据本发明涂布的金属工件可用于制造机械、家用制品或设备、卫生应用、医院以及用于食品处理或制药业。对于最后一个领域,主要使用高级钢。
本发明的涂料具有良好的稳定性,以及耐例如家用或食品工业中发现的大量类型的作用物,如红茶、黑色墨水、炼乳、果汁、醋、芥末、番茄酱、蛋黄酱、洋葱、蔗糖和焦糖引起的脏污。留在未涂布金属表面上的指纹在根据本发明涂布的金属上不会留下任何痕迹,并且可以容易除去。特别地,在直到60℃的温度下,该涂料也可以耐酸性和碱性清洁剂,如冲洗剂、所谓的“钢光泽”或通用清洁剂。同时,表面的外观完全保持。
通过以下的实施例更详细地说明本发明,但选择这些实施例并不会构成对于本发明范围的限制。如果没有特别指明,以下实施例中的所有定量数据为基于组合物整体的重量%或重量份。
实施例
以下本发明的涂料中,刷过的高级钢板用于实施例1~9。涂布前,通过水性微弱碱性清洁剂将所有基材脱脂,然后干燥。本发明的涂料的成分通过在高速搅拌器中剧烈混合而均质化。通过辊涂器或涂布刀将涂料涂布到层重量为<5g/m2,然后在UV装置中,以20m/min的传送带速度,通过UV辐射在标准气氛中固化(发射器类型:Fusion VPS/1600,H-发射器,240W/cm,100%能力)。
各实施例和结果如下表1和2所示(以重量份定量)。
表1
光引发剂是以1-羟基-甲基乙基苯基酮与1-羟基环己基苯基酮的1.5:1的混合物的形式。
测定方法:
1.指纹:在涂布的金属板上产生指纹并视觉评价。任选用软的干布将其擦去。
2.根据DIN 53151进行横切:使用十字影线切刀(Erichsen Model295)制作横切,并在上面粘上胶带,然后将胶带扯掉并评价切口。将切口暴露于蒸汽中后同样地再次进行粘贴和撕扯。
3.沾污:将被涂布金属板表面的5cm2区域用试剂(红茶、柠檬汁、芥末、番茄酱、蛋黄酱)覆盖,并在60℃保存1小时。然后用水冲洗金属板并用软布干燥。
4.耐溶剂性:将几滴溶剂涂布到被涂布金属板上,约5秒后,用软布除去。评价了涂层的膨胀和溶解行为。
5.蒸汽试验:将金属板弯曲90度,然后置于注满沸水的容器上方小距离处,然后在蒸汽中暴露2小时。
本发明涂料的表面质量的检查结果和耐性结果总结在下表2中。表面质量和耐划痕性良好;所有本发明涂料的指纹敏感性同样也是良好。
表2
1)指纹的视觉评价
2)根据DIN53151作标记;在蒸汽中暴露后的结果在括号中示出。
3)食品:芥末、茶、蛋黄酱、番茄酱、柠檬汁等等;弱清洁剂:通用清洁剂,冲洗剂等等
4)试验使用丙酮、石脑油和乙醇进行。
5)用蒸汽处理弯曲了90度的样品钢板2小时,并视觉评价。
6)使用Erichsen硬度试验棒318确定
7)清洁剂:烘箱清洁剂,Ceran清洁剂等。
实施例10-12
使用实施例9的涂料涂布另外的基材并试验:
实施例 | 基材(刷过) | 层厚 | 外观 | 清洁剂 | 指纹 |
10 | 黄铜(MS 39) | 5μm | 状况良好 | + | + |
11 | AlMg1 | 5μm | 状况良好 | + | + |
12 | 铜 | 5μm | 状况良好 | 0 | + |
Claims (19)
1.用于涂布金属基材的无溶剂液体涂料,在0~90℃的温度范围内其粘度低于1000mPas,其含有
a)40~90重量%的低聚的直链或支链环氧(甲基)丙烯酸酯、聚酯(甲基)丙烯酸酯、聚醚(甲基)丙烯酸酯和聚氨酯(甲基)丙烯酸酯的至少一种;
b)5~60重量%的单官能液体(甲基)丙烯酸酯或二、三或更多官能(甲基)丙烯酸酯化合物的至少一种,
c)0.1~20重量%的至少一种含有酸性基团的甲基丙烯酸酯化合物,以及
d)0.1~20重量%的辅助物质,所述辅助物质选自粘合促进剂、流动控制剂、消泡剂、光稳定剂、染料、光学增白剂、颜料、微粉化的填料和/或光引发剂。
2.权利要求1的涂料,其特征在于在15~70℃温度范围内的粘度低于300mPas,并且另外含有0~20重量%的含有另外的官能团的二-或三烷氧基硅烷。
3.权利要求1或2的涂料,其含有磷酸(甲基)丙烯酸酯化合物或膦酸(甲基)丙烯酸酯化合物作为成分c)。
4.权利要求1或2的涂料,其含有细分散的二氧化硅和/或氧化铝作为成分d)。
5.权利要求1或2的涂料,其另外含有杀生物剂。
6.使用权利要求1的涂料涂布金属表面的方法,其特征在于,
a)非必要地将表面清洗和脱脂,
b)以0.5~20μm的层厚涂布涂料,和
c)然后通过高能辐射将涂料交联。
7.权利要求6的方法,其特征在于选择基于铁质材料的材料作为金属表面。
8.权利要求7的方法,其特征在于选择基于钢和合金钢的材料作为金属表面。
9.权利要求7的方法,其特征在于选择基于轻质金属的材料作为金属表面。
10.权利要求7的方法,其特征在于使用的高能辐射为具有波长为150~800nm的UV辐射。
11.权利要求6的方法,其特征在于以干层厚计低于10μm的层厚涂布涂料。
12.权利要求6~11任一项的方法,其特征在于涂料通过浸渍、挤出、辊涂、涂刷器、无气、气助或静电喷涂进行涂布。
13.权利要求12的方法,其特征在于基材为带状,并且通过辊涂进行涂布。
14.权利要求6~11和13中任一项的方法,其特征在于在交联反应过程中,被涂布的基材处于低氧或无氧气氛中。
15.权利要求6~11和13中任一项的方法,其特征在于涂布涂料后施加膜,然后将涂料交联。
16.权利要求15的方法,其特征在于膜由聚乙烯、聚丙烯、PET或它们的混合物组成,并且可与固化的涂层分离。
17.权利要求6~11、13和16中任一项的方法,其特征在于在基材被涂布后,用机械方式将其变为另一种形状。
18.权利要求6~11、13和16中任一项的方法,其特征在于在清洗步骤后,在基材上不施用底层涂料或预处理层。
19.权利要求1的无溶剂液体涂料在涂布金属基材中的应用,所述用于涂布金属基材的无溶剂液体涂料用于为金属表面产生薄的耐清洗涂层。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10144531A DE10144531B4 (de) | 2001-09-11 | 2001-09-11 | UV-härtende anti-fingerprint Beschichtungen, Verfahren zum Beschichten und Verwendung eines lösmittelfreien Überzugsmittels |
DE10144531.8 | 2001-09-11 |
Publications (2)
Publication Number | Publication Date |
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CN1553944A CN1553944A (zh) | 2004-12-08 |
CN100471922C true CN100471922C (zh) | 2009-03-25 |
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CN02817749.5A Expired - Fee Related CN100471922C (zh) | 2001-09-11 | 2002-09-06 | 紫外固化的抗指纹涂层 |
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Country | Link |
---|---|
US (2) | US7816434B2 (zh) |
EP (1) | EP1432771B1 (zh) |
CN (1) | CN100471922C (zh) |
AT (1) | ATE434649T1 (zh) |
AU (1) | AU2002340872B2 (zh) |
BR (1) | BR0212452B1 (zh) |
CA (1) | CA2460237A1 (zh) |
DE (2) | DE10144531B4 (zh) |
WO (1) | WO2003022945A1 (zh) |
ZA (1) | ZA200401954B (zh) |
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-
2001
- 2001-09-11 DE DE10144531A patent/DE10144531B4/de not_active Expired - Lifetime
-
2002
- 2002-09-06 DE DE50213639T patent/DE50213639D1/de not_active Expired - Lifetime
- 2002-09-06 AT AT02774572T patent/ATE434649T1/de not_active IP Right Cessation
- 2002-09-06 AU AU2002340872A patent/AU2002340872B2/en not_active Ceased
- 2002-09-06 BR BRPI0212452-1A patent/BR0212452B1/pt not_active IP Right Cessation
- 2002-09-06 CA CA002460237A patent/CA2460237A1/en not_active Abandoned
- 2002-09-06 WO PCT/EP2002/009967 patent/WO2003022945A1/de not_active Application Discontinuation
- 2002-09-06 CN CN02817749.5A patent/CN100471922C/zh not_active Expired - Fee Related
- 2002-09-06 EP EP02774572A patent/EP1432771B1/de not_active Expired - Lifetime
-
2004
- 2004-03-09 US US10/796,681 patent/US7816434B2/en not_active Expired - Fee Related
- 2004-03-10 ZA ZA200401954A patent/ZA200401954B/en unknown
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2007
- 2007-01-24 US US11/626,729 patent/US20070116947A1/en not_active Abandoned
Also Published As
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DE10144531A1 (de) | 2003-03-27 |
ZA200401954B (en) | 2005-02-21 |
US7816434B2 (en) | 2010-10-19 |
US20070116947A1 (en) | 2007-05-24 |
BR0212452B1 (pt) | 2012-08-07 |
EP1432771B1 (de) | 2009-06-24 |
AU2002340872B2 (en) | 2008-03-06 |
WO2003022945A1 (de) | 2003-03-20 |
EP1432771A1 (de) | 2004-06-30 |
CN1553944A (zh) | 2004-12-08 |
US20040225039A1 (en) | 2004-11-11 |
CA2460237A1 (en) | 2003-03-20 |
DE50213639D1 (de) | 2009-08-06 |
BR0212452A (pt) | 2004-10-19 |
DE10144531B4 (de) | 2006-01-19 |
ATE434649T1 (de) | 2009-07-15 |
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