CN102428132B - 具有改善热稳定性的聚合物涂层 - Google Patents
具有改善热稳定性的聚合物涂层 Download PDFInfo
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- CN102428132B CN102428132B CN201080020610.8A CN201080020610A CN102428132B CN 102428132 B CN102428132 B CN 102428132B CN 201080020610 A CN201080020610 A CN 201080020610A CN 102428132 B CN102428132 B CN 102428132B
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Abstract
本发明涉及包含导电聚合物以及没食子酸和糖的酯的涂层,它们的生产方法和用途,以及用于生产这种涂层的分散体。
Description
本发明涉及包含导电聚合物以及没食子酸和糖的酯的涂层,它们的生产方法和用途,以及用于生产这种涂层的分散体。
来自聚吡咯类、聚苯胺类和聚噻吩类的导电聚合物由文献中已知。特别是聚(3,4-亚烷基二氧噻吩)分散体目前已获得技术重要性,因为它们可例如用于生产导电或抗静电涂层(例如参见EP-A 440957)。然而,在实践中,已发现来自这类分散体的涂层的导电性对于在较高温度和/或UV照射下的实际使用而言不总是充分稳定的。
EP 1798259A1和WO 2008/055834A1公开了如果加入没食子酸(3,4,5-三羟基苯甲酸)的衍生物如没食子酸丙酯,则例如可提高包含聚噻吩分散体的涂层的导电性的热稳定性或UV稳定性。然而,该稳定化作用,特别是对于热稳定性的作用对于许多长期使用而言是不充分的。
因此仍需要与已知涂层相比具有改善热或UV稳定性的导电或抗静电涂层和用于生产这种涂层的合适分散体。
因此,本发明的目的是提供这种具有改善热或UV稳定性的涂层和用于其生产的合适分散体。
现已令人惊讶地发现包含至少一种导电聚合物以及至少一种没食子酸和糖的酯(在下文中称为没食子酸酯)的分散体适于生产例如具有显著更好热稳定性的涂层。
因此,本发明提供一种包含至少一种导电聚合物、至少一种抗衡离子和至少一种分散剂的分散体,其特征在于它包含至少一种没食子酸和糖的酯。
在本发明上下文中,将没食子酸酯理解为指通过名称鞣酸类或没食子酸的单宁物质而汇总于文献中的酯(例如参见http://www.roempp.com/prod/index1.html,关键词鞣酸类或http://www.biologie.uni-hamburg.de/b-online/d26/11.htm)。
下式β-1,2,3,4,5-棓酰基-O-D-葡萄糖代表没食子酸酯的实例:
其中上式中所示棓酰基也可例如被二棓酰基取代。没食子酸酯可作为纯物质或作为各种没食子酸酯的混合物使用。可用于这种分散体的没食子酸酯为市售的。
可将没食子酸酯以基于分散体中导电聚合物如通式(I)聚噻吩的固体含量为1-100重量%,优选5-50重量%,特别优选10-40重量%的量加入本发明分散体中。
在本发明上下文中,将导电聚合物特别理解为指在氧化或还原以后具有导电性的π-共轭聚合物的化合物类别。优选,将导电聚合物理解为指在氧化以后在干燥状态下比电导率为至少0.01S cm-1级数的那些π-共轭聚合物。
优选的分散体为其中至少一种导电聚合物为任选取代的聚噻吩、任选取代的聚苯胺或任选取代的聚吡咯的那些。
一种或多种导电聚合物特别优选选自含有通式(I)重复单元的聚亚烷基二氧噻吩:
其中:
A表示任选取代的C1-C5亚烷基,优选任选取代的C2-C3亚烷基,
R相互独立地表示H,直链或支化的任选取代的C1-C18烷基,任选取代的C5-C12环烷基,任选取代的C6-C14芳基,任选取代的C7-C18芳烷基,任选取代的C1-C4羟基烷基或羟基,优选直链或支化的任选取代的C1-C4烷基,任选取代的C1-C4羟基烷基或羟基,特别优选直链或支化的任选取代的C1-C4烷基或羟基,
x表示0-8的整数,优选0-2的整数,特别优选0或1,且
在数个基团R结合在A上的情况下,这些可相同或不同。
将通式(I)理解为指x个取代基R可结合在亚烷基A上。
特别优选具有其中A表示任选取代的C2-C3亚烷基且x表示0或1的通式(I)重复单元的聚噻吩。
非常特别优选至少一种导电聚合物为任选取代的聚(3,4-亚乙基二氧噻吩)。
在本发明上下文中,将前缀聚理解为指聚合物或聚噻吩含有大于一个相同或不同的重复单元。聚噻吩含有总计n个通式(I)重复单元,其中n为2-2,000,优选2-100的整数。通式(I)重复单元每种情况下在一种聚噻吩中可相同或不同。每种情况下具有相同通式(I)重复单元的聚噻吩是优选的。
聚噻吩优选在各端基上带有H。
在本发明优选实施方案中,分散体包含至少一种含有通式(I)重复单元的聚亚烷基二氧噻吩,其在干燥状态下的比电导率为至少0.05S cm-1,优选至少0.5S cm-1的级数。
分散体中导电聚合物,特别是含有通式(I)重复单元的聚亚烷基二氧噻 吩的固体含量为0.05-3.0重量%,优选0.1-1.5重量%,特别优选0.3-1.0重量%。
在本发明上下文中,C1-C5亚烷基A优选为亚甲基、亚乙基、正亚丙基、正亚丁基或正亚戊基。C1-C18烷基R优选表示直链或支化C1-C18烷基,例如甲基,乙基,正-或异丙基,正-、异-、仲-或叔丁基,正戊基,1-甲基丁基,2-甲基丁基,3-甲基丁基,1-乙基丙基,1,1-二甲基丙基,1,2-二甲基丙基,2,2-二甲基丙基,正己基,正庚基,正辛基,2-乙基己基,正壬基,正癸基,正十一烷基,正十二烷基,正十三烷基,正十四烷基,正十六烷基或正十八烷基;C1-C4烷基优选表示直链或支化C1-C4烷基,例如甲基,乙基,正-或异丙基,正-、异-、仲-或叔丁基,此外,C1-C8烷基还表示例如正戊基、1-甲基丁基、2-甲基丁基、3-甲基丁基、新戊基、1-乙基丙基、环己基、环戊基、正己基、1,1-二甲基丙基、1,2-二甲基丙基、1-甲基戊基、2-甲基戊基、3-甲基戊基、4-甲基戊基、1,1-二甲基丁基、1,2-二甲基丁基、1,3-二甲基丁基、2,2-二甲基丁基、2,3-二甲基丁基、3,3-二甲基丁基、1-乙基丁基、2-乙基丁基、1,1,2-三甲基丙基、1,2,2-三甲基丙基、1-乙基-1-甲基丙基、1-乙基-2-甲基丙基或1-乙基-2-甲基丙基;在本发明上下文中,C1-C4羟基烷基R优选表示被一个或多个,但优选一个羟基取代的直链、环状、支化或非支化C1-C4烷基;C5-C12环烷基R表示例如环戊基、环己基、环庚基、环辛基、环壬基或环癸基;C6-C14芳基R表示例如苯基或萘基,C7-C18芳烷基R表示例如苄基,邻-、间-、对甲苯基,2,3-、2,4-、2,5-、2,6-、3,4-、3,5-二甲苯基或 基。上述序列用于举例阐述本发明且不认为是限定性的。
在本发明上下文中,大量有机基团是基团A和/或基团R的可能任选其它取代基,例如烷基、环烷基、芳基、芳烷基、烷氧基、卤素、醚、硫醚、二硫化物、亚砜、砜、磺酸根、氨基、醛、酮、羧酸酯、羧酸、碳酸根、羧酸根、氰基、烷基硅烷和烷氧基硅烷基团以及羧酰胺基团。
聚苯胺或聚吡咯的可能取代基例如为上文所列基团A和R和/或基团A和R的其它取代基。优选使用未取代的聚苯胺和聚吡咯。
本发明上下文包括以上和下文给出的所有基团定义、参数和解释,其彼此为通常的或在优选范围内提到,也就是说为具体范围与优选范围之间 的任何所需组合。
用作分散体中的导电聚合物的聚噻吩可以为中性或阳离子的。在优选实施方案中,它们为阳离子的,“阳离子”仅与聚噻吩主链上的电荷有关。聚噻吩可取决于基团R上的取代基在结构单元上带有正和负电荷,其中正电荷在聚噻吩主链上,负电荷任选在被磺酸根或羧酸根取代的基团R上。在本文中,聚噻吩主链的正电荷可通过任选存在于基团R上的阴离子基团部分或完全饱和。总之,在这些情况下,聚噻吩可以为阳离子、中性或甚至阴离子的。然而,在本发明上下文中,一概将它们认为是阳离子聚噻吩,因为聚噻吩主链上的正电荷是决定性的。式中未显示出正电荷,因为不能完全确定它们的准确数量和位置。然而,正电荷的数量为至少1且至多n,其中n为聚噻吩内所有重复单元(相同或不同)的总数。
为补偿正电荷,如果这还没有通过任选磺酸根-或羧酸根取代且因此带负电荷的基团R进行,则阳离子聚噻吩需要阴离子作为抗衡离子。
抗衡离子可以为单体或聚合阴离子,其中后者在下文中也称为聚阴离子。
聚合阴离子优于单体阴离子,因为它们有助于成膜且因为它们的大小导致对热更稳定的导电膜。然而,除聚合阴离子外,分散体也可含有单体阴离子。
此处聚合阴离子可例如为聚合羧酸如聚丙烯酸、聚甲基丙烯酸或聚马来酸,或聚合磺酸如聚苯乙烯磺酸和聚乙烯磺酸的阴离子。这些聚羧酸和聚磺酸也可为乙烯基羧酸和乙烯基磺酸与其它可聚合单体如丙烯酸酯和苯乙烯的共聚物。
优选,本发明分散体包含至少一种聚合羧酸或磺酸的阴离子作为抗衡离子。
聚苯乙烯磺酸(PSS)的阴离子特别优选作为聚合阴离子。
提供聚阴离子的多酸的分子量优选为1,000-2,000,000,特别优选2,000-500,000。多酸或它们的碱金属盐是市售的,例如聚苯乙烯磺酸和聚丙烯酸,或可通过已知方法(例如参见Houben Weyl,Methoden der organischen Chemie,第E 20卷Makromolekulare Stoffe,第2部分,(1987), 第1141及随后各页)制备。
分散体可包含重量比特别为0.5∶1-50∶1,优选1∶1-30∶1,特别优选2∶1-20∶1的聚合阴离子和导电聚合物。此处导电聚合物的重量对应于所用单体的重量,其中假设在聚合期间进行完全转化。
使用的单体阴离子例如为C1-C20链烷磺酸如甲烷-、乙烷-、丙烷-、丁烷磺酸或高级磺酸如十二烷磺酸,脂族C1-C20全氟磺酸如三氟甲烷磺酸、全氟丁烷磺酸或全氟辛烷磺酸,脂族C1-C20羧酸如2-乙基己基羧酸,脂族C1-C20全氟羧酸如三氟乙酸或全氟辛酸,和任选被C1-C20烷基取代的芳族磺酸如苯磺酸、邻甲苯磺酸、对甲苯磺酸或十二烷基苯磺酸,和环烷烃磺酸如樟脑磺酸的那些,或四氟硼酸根、六氟磷酸根、高氯酸根、六氟锑酸根、六氟砷酸根或六氯锑酸根。
对甲苯磺酸、甲烷磺酸或樟脑磺酸的阴离子优选作为单体阴离子。
含有阴离子作为抗衡离子用于电荷补偿的阳离子聚噻吩在技术领域中还通常称为聚噻吩/(聚)阴离子配合物。
本发明分散体中例如这种聚合物/抗衡离子配合物形式的导电聚合物和抗衡离子的总含量基于分散体的总重量例如为0.05-10重量%,优选0.1-2重量%。
本发明分散体可包含一种或多种分散剂。可提到的分散剂例如为如下溶剂:脂族醇如甲醇、乙醇、异丙醇和丁醇;脂族酮如丙酮和甲基乙基酮;脂族羧酸酯如乙酸乙酯和乙酸丁酯;芳族烃如甲苯和二甲苯;脂族烃如己烷、庚烷和环己烷;氯代烃如二氯甲烷和二氯乙烷;脂族腈如乙腈;脂族亚砜和砜如二甲亚砜和环丁砜;脂族羧酸酰胺如甲基乙酰胺、二甲基乙酰胺和二甲基甲酰胺;以及脂族和芳脂族醚如乙醚和茴香醚。此外,水或水与上述有机溶剂的混合物也可用作分散剂。
优选的分散剂为水或其它质子溶剂,例如醇如甲醇、乙醇、异丙醇和丁醇,以及水与这些醇的混合物;水是特别优选的溶剂。
此外,分散体可包含其它组分,例如表面活性物质如离子和非离子表面活性剂,或增粘剂如有机官能硅烷或其水解产物如3-缩水甘油氧基丙基三烷氧基硅烷、3-氨基丙基三乙氧基硅烷、3-巯基丙基三甲氧基硅烷、3- 甲基丙烯酰氧基丙基三甲氧基硅烷、乙烯基三甲氧基硅烷或辛基三乙氧基硅烷。
本发明分散体可包含提高传导性的其它添加剂,例如含有醚基团的化合物如四氢呋喃,含有内酯基团的化合物如γ-丁内酯、γ-戊内酯,含有酰胺或内酰胺基团的化合物如己内酰胺、N-甲基己内酰胺、N,N-二甲基乙酰胺、N-甲基乙酰胺、N,N-二甲基甲酰胺(DMF)、N-甲基甲酰胺、N-甲基甲酰苯胺、N-甲基吡咯烷酮(NMP)、N-辛基吡咯烷酮、吡咯烷酮,砜和亚砜如环丁砜(四亚甲基砜)、二甲亚砜(DMSO),糖或糖衍生物如蔗糖、葡萄糖、果糖、乳糖,糖醇如山梨醇、甘露醇,呋喃衍生物如2-呋喃羧酸、3-呋喃羧酸,和/或二-或多元醇如乙二醇、甘油、二-和三甘醇。四氢呋喃、N-甲基甲酰胺、N-甲基吡咯烷酮、乙二醇、二甲亚砜或山梨醇特别优选用作提高导电性的添加剂。
此外,本发明分散体还可包含一种或多种可溶于有机溶剂中或水溶性的有机基料,例如聚乙酸乙烯酯、聚碳酸酯、聚乙烯基丁缩醛、聚丙烯酸酯、聚丙烯酰胺、聚甲基丙烯酸酯、聚甲基丙烯酰胺、聚苯乙烯、聚丙烯腈、聚氯乙烯、聚乙烯吡咯烷酮、聚丁二烯、聚异戊二烯、聚醚、聚酯、聚氨酯、聚酰胺、聚酰亚胺、聚砜、聚硅氧烷、环氧树脂、苯乙烯/丙烯酸酯、乙酸乙烯酯/丙烯酸酯和乙烯/乙酸乙烯酯共聚物、聚乙烯醇或纤维素。
本发明分散体中聚合物基料的含量基于分散体的总重量为0.1-90重量%,优选0.5-30重量%,非常特别优选0.5-10重量%。
如果任选包含在分散体中的这种有机基料在给定的温度下为液体,则它也可任选充当分散剂。
本发明分散体可具有1-14的pH;1-8的pH是优选的。
可例如将碱或酸加入分散体中以调整pH。不降低分散体的成膜且在较高温度如固化温度下不挥发的那些添加剂,例如碱2-(二甲基氨基)乙醇、2,2′-亚氨基二乙醇或2,2′,2″-次氮基三乙醇和酸如聚苯乙酸磺酸是优选的。
本发明分散体的粘度取决于应用方法可以为0.1-100,000mPa·s(在20℃和100s-1的剪切速率下测量)。优选粘度为1-10,000mPa·s,特别优选10-1,000mPa·s。
例如类似于EP-A 440957所述条件,本发明分散体的制备通过首先在抗衡离子的存在下由用于制备导电聚合物的相应前体制备导电聚合物的分散体而进行。用于制备这些分散体的改进变化方案是使用离子交换剂除去无机盐内容物或其一部分。这一变化方案例如描述于DE-A 19627071中。可将离子交换剂例如与产物搅拌,或传送产物经过装有离子交换剂柱的塔。低金属含量例如可通过使用离子交换剂实现。
分散体中粒子的粒度可在脱盐以后例如通过高压均化器降低。也可重复该操作以提高效果。在此处证明100-2,000巴的特别高的压力特别有利于极大地降低粒度。
制备聚苯胺/聚阴离子、聚吡咯/聚阴离子或聚噻吩/聚阴离子配合物,随后分散或再分散在一种或多种分散剂中也是可能的。
为制备本发明分散体,然后将其它组分如没食子酸酯、任选其它分散剂和任选其它添加剂、有机基料等加入这些分散体中,例如搅拌下将组分混合。
将相应单体例如理解为用于制备导电聚合物的前体,在下文中也称为前体。也可使用各种前体的混合物。合适的单体前体例如为任选取代的噻吩、吡咯或苯胺,优选任选取代的噻吩,特别优选任选取代的3,4-亚烷基二氧噻吩。
作为取代的3,4-亚烷基二氧噻吩,可例如提到通式(II)化合物:
其中:
A表示任选取代的C1-C5亚烷基,优选任选取代的C2-C3亚烷基,
R相互独立地表示H,直链或支化的任选取代的C1-C18烷基,任选取代的C5-C12环烷基,任选取代的C6-C14芳基,任选取代的C7-C18芳烷基,任选取代的C1-C4羟基烷基或羟基,优选直链或支化的任选取代的C1-C4烷基,任选取代的C1-C4羟基烷基或羟基,特别优选直链或支化的任选 取代的C1-C4烷基或羟基,
x表示0-8的整数,优选0-2的整数,特别优选0或1,且
在数个基团R结合在A上的情况下,这些可相同或不同。
非常特别优选的单体前体为任选取代的3,4-亚乙基二氧噻吩,在优选实施方案中,为未取代的3,4-亚乙基二氧噻吩。
用于上述前体,特别是用于噻吩,优选用于3,4-亚烷基二氧噻吩的可能取代基为关于通式(III)的R所提到的基团。
用于吡咯和苯胺的可能取代基例如为上文所列基团A和R和/或基团A和R的其它取代基。
基团A和/或基团R的可能任选其它取代基为关于通式(I)所提到的有机基团。
用于制备导电聚合物的单体前体的制备方法是本领域技术人员已知的,且例如描述于L.Groenendaal,F.Jonas,D.Freitag,H.Pielartzik&J.R.Reynolds,Adv.Mater.12(2000)481-494和其中所引用的文献中。
本发明分散体显著适于生产具有电性能的热稳定性的导电或抗静电涂层。
因此,本发明还提供可由本发明分散体得到的导电或抗静电涂层。
为生产本发明涂层,将本发明分散体例如通过已知方法,例如通过旋涂、浸渍、浇注、滴落、喷雾、起雾、刀涂、刷涂或印刷如喷墨、丝网、凹版、平版或擦涂印刷以0.5-250μm的湿膜厚度,优选以2-50μm的湿膜厚度应用于合适基质上,然后在至少20-200℃的温度下干燥。
本发明分散体显示出由其形成的涂层的电性能在室温以上,特别是在80℃以上的温度下显著更高的稳定性。
以下实施例用于举例阐述本发明且不应解释为限制性的。
实施例:
比较例1:
使用筛目为140/cm的聚酯纤维筛网用商业丝网印刷浆料Clevios SV3(生产商H.C.Starck GmbH,Goslar)形成测试打印。打印区域的尺寸为10×2cm2。将印迹在循环空气烘箱中在130℃下干燥15分钟。然后将2个 导电银电极与纵向成直角以2cm的距离应用于膜的中间,将该体系在室温下干燥24小时。然后借助夹钳将导电银电极连接在万用表上,并测量表面电阻:
表面电阻:400欧姆/平方。
根据本发明的实施例1:
搅拌下将1.0g单宁(Aldrich)溶于200g来自比较例的丝网印刷浆料中,如比较例所述形成测试打印,测定表面电阻。
表面电阻450欧姆/平方。
然后将测试打印在120℃下存放在空气中,在312小时后测定表面电阻。
表面电阻[欧姆/平方]:
在存放以前在120℃下312小时以后
比较例1 400 2,600
实施例1 450 660
根据本发明的没食子酸酯添加剂在由加入根据本发明没食子酸酯添加剂的聚噻吩分散体形成的涂层中的稳定作用由该比较变得清楚。
比较例2(根据EP1798259):
搅拌下将1.0g没食子酸丙酯(Aldrich)溶于200g来自比较例1的丝网印刷浆料中,如比较例1所述形成测试打印,测定表面电阻。
根据本发明的实施例2:
搅拌下将1.0g单宁(Aldrich)溶于200g来自比较例1的丝网印刷浆料中,如比较例2所述形成测试打印,测定表面电阻。
然后将测试打印在150℃下存放在空气中,在216小时以后测定表面电阻并计算以起始值的%表示的电阻提高。
以%表示的电阻提高(在150℃下存
放以后的R/形成以后的R×100)
比较例1 520
比较例2 350
根据本发明的实施例2 230
Claims (15)
1.包含至少一种导电聚合物、至少一种抗衡离子和至少一种分散剂的分散体,其特征在于所述分散体包含至少一种没食子酸和糖的酯。
2.根据权利要求1的分散体,其特征在于至少一种导电聚合物选自任选取代的聚噻吩、任选取代的聚苯胺或任选取代的聚吡咯。
4.根据权利要求3的分散体,其特征在于至少一种导电聚合物为聚(3,4-亚乙基二氧噻吩)。
5.根据权利要求1-4中任一项的分散体,其特征在于至少一种抗衡离子为单体或聚合阴离子。
6.根据权利要求5的分散体,其特征在于聚合阴离子选自聚合羧酸或磺酸。
7.根据权利要求6的分散体,其特征在于聚合阴离子为聚苯乙烯磺酸。
9.根据权利要求8的分散体,其特征在于抗衡离子为选自聚合羧酸或磺酸的聚合阴离子,导电聚合物为聚(3,4-亚乙基二氧噻吩)。
10.根据权利要求8的分散体,其特征在于抗衡离子为聚苯乙烯磺酸,导电聚合物为聚(3,4-亚乙基二氧噻吩)。
11.根据权利要求1-4中任一项的分散体,其特征在于它包含量基于分散体中导电聚合物的固体含量为1-100重量%的一种或多种没食子酸酯。
12.根据权利要求1-4中任一项的分散体,其特征在于所述分散体包含至少一种聚合物有机基料。
13.根据权利要求1-4中任一项的分散体,其特征在于它包含水、脂族醇、脂族酮、脂族羧酸酯、芳族烃、脂族烃、氯代烃、脂族腈、脂族亚砜和砜、脂族羧酸酰胺、脂族和芳脂族醚或上述试剂中至少两种的混合物作为分散剂。
14.根据权利要求1-13中任一项的分散体在生产导电或抗静电涂层中的用途。
15.由根据权利要求1-13中任一项的分散体得到的导电或抗静电涂层。
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US8936735B2 (en) | 2015-01-20 |
EP2406309B1 (en) | 2013-06-05 |
DE102009012660A1 (de) | 2010-09-16 |
KR101666241B1 (ko) | 2016-10-13 |
JP5965005B2 (ja) | 2016-08-03 |
WO2010102751A2 (en) | 2010-09-16 |
TWI478971B (zh) | 2015-04-01 |
TW201038643A (en) | 2010-11-01 |
KR20120009448A (ko) | 2012-01-31 |
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