CN101910348B - 高折射率粘合剂 - Google Patents
高折射率粘合剂 Download PDFInfo
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- CN101910348B CN101910348B CN200880122445XA CN200880122445A CN101910348B CN 101910348 B CN101910348 B CN 101910348B CN 200880122445X A CN200880122445X A CN 200880122445XA CN 200880122445 A CN200880122445 A CN 200880122445A CN 101910348 B CN101910348 B CN 101910348B
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- monomeric unit
- methyl
- acid
- monomer
- tackiness agent
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Classifications
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- C—CHEMISTRY; METALLURGY
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Abstract
本发明提供折射率为至少1.50的压敏粘合剂。所述压敏粘合剂包含至少一种含取代或未取代的咔唑基的单体。
Description
技术领域
本发明涉及压敏及热活化粘合剂。更具体地说,本发明涉及具有高折射率的粘合剂。
背景技术
压敏粘合剂(“PSA”)在本文中定义为在室温下显示出持久粘性的粘合剂。这种性能使得只用手指施加很轻的压力时便可以使压敏粘合剂强力地粘附。PSA具有下述平衡的性能:粘附力、内聚力、延展性及弹性。粘附力既指对表面的直接粘附力,又指经施加压力产生的粘结强度(往往测定的是“剥离强度”)。内聚力指的是受到剪切力时的“抗剪强度”或所施加的PSA对失效的抵抗力。延展性指的是在低应力下的延长能力。弹性指的是这样的性能,其中材料被拉伸时显示出回缩力,而当力解除时材料回缩。
热活化粘合剂(“HA”)在本文中定义为这样的粘合剂,其在室温下是非粘性的,但在高温下变得暂时发粘,并且能够粘结到基材上。在或高于此活化温度时,它们具有与PSA相同的特性,即粘附力、内聚力、延展性及弹性。这些粘合剂通常具有高于室温的Tg或熔点(Tm)。当温度升高到超过Tg或Tm时,储能模量通常减小,粘合剂变得发粘。
压敏及热活化粘合剂具有许多各种各样的应用,包括在光学产品中的应用。对于某些光学应用来说,使粘合剂的折射率(RI)与施加粘合剂之基材的折射率相匹配是有利的。这种折射率的匹配可通过减少眩光和反射而提高构造的光学性能。眩光在本文中定义为450-650纳米范围内的平均反射,反射在本文中定义为这样一个过程,其中一部分入射到表面的辐射光通量返回到同一半球,该半球的底部为所述表面且包含入射辐射。(参见《光学手册》第二版,McGraw-Hill出版社1995年)。基材往往是折射率在1.48至1.65范围内的聚合物材料,例如RI为1.489的聚(甲基)丙烯酸甲酯(PMMA)、RI为1.585的聚碳酸酯和RI为1.64的聚对苯二甲酸乙二醇酯(PET)。
发明内容
典型的PSA及热活化粘合剂的折射率为约1.47或更小。如果在光学应用中使用这些PSA,那么就可能会发生眩光及反射。因此有必要获得具有高折射率的一类粘合剂。
本发明提供折射率为至少1.50的粘合剂。这些压敏及热活化粘合剂特别适用于其中基材或粘附体同样具有高折射率的光学应用。本发明的压敏粘合剂可有利地允许折射率相匹配,这样可减少眩光及反射。
在许多实施例中,本发明还提供光透射值为至少85%、优选为至少90%的光学透明的粘合剂。术语“光透射值”是一个百分数,其表示既不向着光源反射、也不被膜吸收的光为550nm波长的总入射光的百分比(射出光/光源×100)。所述粘合剂还具有小于2%、优选小于1%的雾度。
本发明的粘合剂包含至少一种含咔唑基的单体。本发明的一个方面是一种压敏粘合剂,所述压敏粘合剂包含以下物质的互聚反应产物:(a)至少一种选自(甲基)丙烯酸酯的单体;和(b)至少一种含咔唑基的单体。如本文中所用,术语“(甲基)丙烯酸系”或“(甲基)丙烯酸酯”包括丙烯酸系和甲基丙烯酸系(或丙烯酸酯和甲基丙烯酸酯)。
本发明的另一方面是一种压敏粘合剂,所述压敏粘合剂包含以下物质的互聚反应产物:(a)至少一种(甲基)丙烯酸酯单体;(b)至少一种含取代或未取代的咔唑基的单体;和(c)至少一种含酸官能团的单体。
本发明的再一方面是一种压敏粘合剂,所述压敏粘合剂包含以下物质的互聚反应产物:(a)至少一种(甲基)丙烯酸酯单体;(b)至少一种含取代或未取代的咔唑基的单体;和(c)任选的至少一种酸官能团的单体;和(d)至少一种能够与组分(a)、(b)和(c)之单体共聚的不含酸的极性单体。
本发明的压敏粘合剂任选包含其它的单体、交联剂和其它添加剂。
本发明的另一实施例是一种涂有本发明的压敏粘合剂的基材。
具体实施方式
本发明涉及折射率为至少1.50的粘合剂。优选的是,所述粘合剂的折射率为至少1.54。
本发明的压敏粘合剂具有高折射率,并且与压敏粘合剂相关的四种性能仍然具有良好的平衡:粘附力、内聚力、延展性及弹性。所述粘合剂在使用温度下符合Dahlquist标准(参见《压敏粘合剂技术手册》,D.Satas著,第二版第172页(1989年))。此标准规定良好的压敏粘合剂在1秒时的蠕变柔量大于1×10-6平方厘米/达因。作为另外的选择,由于作为一级近似,模量是柔量的倒数,因此可把压敏粘合剂定义为剪切模量小于1×106达因/平方厘米的粘合剂。
本文中定义的折射率为材料(例如,单体或其聚合产物)的绝对折射率,可理解为电磁辐射在真空中的速度与辐射在该材料中的速度之比,所述辐射为波长约583.9纳米(nm)的钠黄光。可以采用已知的方法测定折射率,通常使用阿贝折射计进行测定。
本发明的压敏粘合剂是包含至少一种咔唑单体的(甲基)丙烯酸酯粘合剂。压敏粘合剂可以包含至少一种非叔醇的(甲基)丙烯酸酯、至少一种或多种酸官能团的单体和可选的一种或多种非酸官能团的极性单体。本发明的压敏粘合剂任选包含为改善粘合剂物理性能而添加的其它单体(如交联剂)以及其它添加剂(如增粘剂或增塑剂)。
相对于100重量份单体总和来说,适用于本发明之压敏粘合剂的(甲基)丙烯酸系单体通常占约5至约95重量份,优选占10至90重量份。适用的丙烯酸系单体包括至少一种选自单体性之非叔烷基醇(其烷基包含约1至约12个碳原子、优选约4至约8个碳原子)的丙烯酸酯或甲基丙烯酸酯的单体以及它们的混合物。
合适的(甲基)丙烯酸酯单体包括(但不限于)选自丙烯酸或甲基丙烯酸与非叔烷基醇(如1-丁醇、1-戊醇、2-戊醇、3-戊醇、2-甲基-1-丁醇、1-甲基-1-丁醇、1-甲基-1-戊醇、2-甲基-1-戊醇、3-甲基-1-戊醇、2-乙基-1-丁醇、2-乙基-1-己醇、3,5,5-三甲基-1-己醇、3-庚醇、2-辛醇、1-癸醇、1-十二烷醇等)之酯的那些以及它们的混合物。这种单体性丙烯酸酯或甲基丙烯酸酯是所属领域中已知的,并且是市售的。
优选的是,选择丙烯酸酯单体使得对所得到的粘合剂赋予低玻璃化转变温度(Tg)。这种单体的Tg通常低于0℃,更优选低于-20℃,所测得的Tg取决于所述的均聚物。可以参考《压敏粘合剂技术手册》,D.Satas著,第二版第399页(1989年)。
咔唑单体是高折射率的丙烯酸系单体,优选这种丙烯酸系单体全都具有等于或低于70℃的均聚物玻璃化转变温度。当这些咔唑单体单独聚合或在其它丙烯酸系单体存在的情况下聚合时,所得之PSA的RI比以其他的方式得到的要高。通过调节单体的比例可以制备RI为至少1.50的PSA。通常情况下,相对于100重量份单体总和来说,粘合剂包含95至约5重量份、优选90至10重量份的咔唑单体。
本发明的芳香族单体可由如下的通式表示:
其中
X2是-O-、-S-或-NR3-,其中R3是H或C1-C4烷基,优选X2是-O-;
R1是1至8个碳的亚烷基,任选包含一个或多个醚氧原子和一个或多个侧羟基;
n是1至3;且
R2是H或者是CH3。
在某些优选的实施例中,R1是1至8个碳的亚烷基,即-CaH2a-,其中a是1至8。在其它实施例中,R1可以包含一个或多个链中醚氧原子,例如-CbH2b-O-CcH2c-,其中b和c是至少1,b+c是2至8。在另一实施例中,R1可以包含侧羟基,例如-CbH2b-CH(OH)-CcH2c-,其中b和c是至少1,b+c是2至8。如果需要的话,可以使咔唑基溴化以提高所得粘合剂的折射率。然而这种溴取代也可以提高粘合剂的Tg。
据信其中R1是6至8情况下的式I化合物是新型的。已经进一步发现的是,这些化合物与其中R1≤4的同系物相比具有显著低的Tg,但仍然保持高折射率,因此适合作为高折射率PSA。根据需要,任选使均聚物和共聚物与增塑剂和增粘剂共混。
根据Donatas Satas著的《压敏粘合剂技术手册》,第一版,VonNostrand Rheinhold,纽约,1982年:“玻璃化转变温度既不是室温下聚合物硬度的准确量度,也不是压敏性能的准确量度。这是一种预测聚合物是否适合应用于压敏粘合剂以及预测共聚单体对共聚物性能之影响的简便方法”。
通过使(甲基)丙烯酰基化合物(如酯或酰卤)与咔唑化合物的简单缩合可以制备n=0情况下的式I之含咔唑的单体。可以按两步合成法制备n=1-3情况下的式I之化合物,其中首先用式Z1-R1-X2H之化合物使具有亲核-XH基团的咔唑化合物烷基化,其中Z1是诸如卤离子的离去基团,然后如下所示与(甲基)丙烯酰基化合物缩合:
制备式I之咔唑单体的其它方法对本领域技术人员而言是显而易见的。例如,使咔唑化合物与碳酸乙二酯反应,然后与(甲基)丙烯酰基化合物缩合,由此可以制备n=2情况下的式I单体。
粘合剂共聚物可以还包含酸官能团的单体,其中所述酸官能团可以是酸本身,如羧酸,或者是其盐,如碱金属羧酸盐。适用的酸官能团的单体包括(但不限于)选自烯键式不饱和羧酸、烯键式不饱和磺酸、烯键式不饱和膦酸的那些以及它们的混合物。这种化合物的例子包括选自丙烯酸、甲基丙烯酸、衣康酸、富马酸、巴豆酸、柠康酸、马来酸、油酸、丙烯酸β-羧乙酯、甲基丙烯酸2-磺乙酯、苯乙烯磺酸、2-丙烯酰胺基-2-甲基丙烷磺酸、乙烯基膦酸的那些以及它们的混合物。
由于容易获得,本发明的酸官能团的单体通常选自烯键式不饱和羧酸,即(甲基)丙烯酸。当需要甚至更强的酸时,酸性单体包括烯键式不饱和磺酸和烯键式不饱和膦酸。当有酸官能团的单体时,按100重量份单体总和计,酸官能团的单体的用量通常为1至15重量份,优选为1至10重量份。在诸如电子应用的一些实施例中没有酸官能团的单体,因为它们会对这种设备的性能产生有害的影响。
粘合剂共聚物可以还包含除酸官能团的单体以外的其它极性单体,用以提高压敏粘合剂的内聚强度。适用的极性单体包括(但不限于)丙烯酰胺、N-烷基(甲基)丙烯酰胺、N,N-二烷基取代的(甲基)丙烯酰胺、N-乙烯基内酰胺和(甲基)丙烯酸N,N-二烷基氨烷基酯、(甲基)丙烯酸羟烷酯以及它们的混合物。示例性例子包括(但不限于)选自N,N-二甲基(甲基)丙烯酰胺、N,N-二乙基(甲基)丙烯酰胺、(甲基)丙烯酸N,N-二甲氨基乙酯、(甲基)丙烯酸N,N-二甲氨基丙酯、(甲基)丙烯酸N,N-二甲氨基丙酯、丙烯酸2-羟乙酯等的那些以及它们的混合物。
优选的非酸极性单体包括丙烯酰胺、甲基丙烯酰胺、丙烯腈、甲基丙烯腈以及它们的混合物。一般来说,按100重量份单体总和计,非酸极性单体通常占约0至约12重量份,优选占约2至约8重量份。
可以按不会使压敏粘合剂变成非粘性的量添加其它的乙烯基单体以改善性能、降低成本等。若使用的话,适用于粘合剂共聚物的乙烯基单体包括乙烯基酯(例如乙酸乙烯酯和丙酸乙烯酯)、苯乙烯、取代的苯乙烯(例如α-甲基苯乙烯)以及它们的混合物。按100重量份单体总和计,这种乙烯基单体通常的用量为0至5重量份,优选为1至5重量份。
单体的可共聚混合物可以还包含链转移剂以控制所得共聚物的分子量。适用的链转移剂例子包括(但不限于)选自醇、硫醇的那些以及它们的混合物。优选的链转移剂为巯基乙酸异辛酯。如果使用链转移剂,则按100重量份全部单体的混合物计,混合物可以还包含最多0.5重量份的链转移剂,通常为约0.01至约0.5重量份,优选为约0.05至约0.2重量份。
为了提高聚(甲基)丙烯酸酯压敏粘合剂的内聚强度,可以把交联剂掺入到粘合剂组合物当中。示例性的有两种主要类型的化学交联剂。第一种交联添加剂为热交联剂,如多官能氮丙啶、异氰酸酯、噁唑和环氧化合物。氮丙啶交联剂的一个例子是1,1′-(1,3-亚苯基二羰基)-双(2-甲基氮丙啶)(CAS No.7652-64-4)。其它双酰胺交联剂描述在U.S.6,893,718(Melancon等人)中。常见的多官能异氰酸酯交联剂有所属领域中已知的三羟甲基丙烷甲苯二异氰酸酯、甲苯二异氰酸酯等。可以在聚合之后将这种化学交联剂添加到溶剂型PSA当中,并在用烘箱干燥涂布的粘合剂期间进行热活化。
双酰胺交联剂可以是下式的
其中,
每个R4独立地选自H和CnH2n+1,其中
n是1至5的整数,
R5是二价基,选自苯基、取代的苯基、三嗪和-CnH2m-(其中m是1至10的整数)以及它们的组合。
适用于本发明的多官能噁唑啉交联剂为每个分子含两个或多个选自2-噁唑啉、2-噁嗪及其组合的基团的那些。优选的1,3-噁唑基杂环化合物(1,3-oxazyl heterocyclic compound)为1,3-噁唑啉,特别优选的1,3-噁唑啉为2-苯基-2-噁唑啉。双噁唑啉通常衍生自多元羧酸,这种多元羧酸包括(但不限于)芳香族酸,例如间苯二甲酸、对苯二甲酸、5-叔丁基间苯二甲酸、均苯三甲酸、1,2,4,5-苯四羧酸和2,6-萘二羧酸。优选的多元羧酸包括间苯二甲酸、对苯二甲酸和均苯三甲酸。
可以通过多元羧酸的相应酯与链烷醇胺反应方便地制备适用于本发明的多官能1,3-噁唑基杂环化合物。聚(1,3-噁唑基杂环)化合物的非限制性例子包括具有由下式III表示的核的双噁唑啉:
其中A选自具有1至20个碳原子的环或无环脂肪族部分或取代的环或无环脂肪族部分,或具有6至20个碳原子的芳香族(芳基)单或多环芳基残基或脂肪族取代的芳基残基,以及包含约2至200,000个重复单元的聚合物或低聚物残基;
R7独立地表示H、CH3、CH2CH3或C6H5;
R8和R9独立地表示H或CH3,优选R7和R9不都是CH3;
x表示整数0或1;
n是2或更大的整数,优选为2或3。
适用的多官能噁唑啉交联剂包括(但不限于)4,4′-5,5′-四氢-2,2′-双噁唑(即,2,2′-双(2-噁唑啉));2,2′-(链烷二基)双[4,5-二氢噁唑],例如2,2-(1,4-丁二基)双[4,5-二氢噁唑]和2,2′-(1,2-乙二基)双[4,5-二氢噁唑];2,2′-(亚芳基)双[4,5-二氢噁唑],例如2,2′-(1,4-亚苯基)双[4,5-二氢噁唑];2,2-(1,5-萘基)双[4,5-二氢噁唑]和2,2-(1,8-蒽基)双[4,5-二氢噁唑];磺酰基、氧代基、硫代或亚烷基双2-(亚芳基)[4,5-二氢噁唑],例如磺酰基双2-(1,4-亚苯基)双[4,5-二氢噁唑]、氧代双2-(1,4-亚苯基)双[4,5-二氢噁唑]、硫代双2-(1,4-亚苯基)双[4,5-二氢噁唑]和亚甲基双2-(1,4-亚苯基)双[4,5-二氢噁唑];2,2′,2″-(亚芳基三[4,5-二氢噁唑],例如2,2′,2″-(1,3,5-亚苯基三[4,5-二氢噁唑];2,2′,2″,2″′-(亚芳基四[4,5-二氢噁唑],例如2,2′,2″,2″′-(1,2,4,5-亚苯基四[4,5-二氢噁唑],以及具有噁唑啉端基的低聚物和聚合物材料。
通常情况下,这种交联剂的用量是每100pph(固体)的粘合剂共聚物为约0.05至1.0pph的交联剂。
在另一实施例中,可以使用依靠自由基进行交联反应的化学交联剂。诸如过氧化物的试剂充当自由基源。当充分受热时,这些前体将通过夺氢产生自由基,导致发生聚合物的交联反应。一种常见的自由基生成剂是过氧化苯甲酰。只需要少量的自由基发生剂,但是与双酰胺试剂所需的相比,为了完成交联反应,通常需要更高的温度。
第二种类型的化学交联剂是通过高强度紫外(UV)光活化的光敏交联剂。用于丙烯酸系PSA的两种常见的光敏交联剂是二苯甲酮和可共聚的芳香族酮单体,如美国专利No.4,737,559中所述。可以后加入到溶液聚合物中并通过UV光活化的另一种光交联剂是三嗪,例如2,4-双(三氯甲基)-6-(4-甲氧基-苯基)-均三嗪。这些交联剂通过由诸如中压汞灯的人工光源产生的UV光或UV黑光活化。
诸如多官能丙烯酸酯的多烯键式不饱和化合物适合作为本体聚合或乳液聚合过程中的交联剂。多烯键式不饱和化合物的例子包括(但不限于):多丙烯酸官能团的单体,如乙二醇二丙烯酸酯、丙二醇二甲基丙烯酸酯、双酚-A二(甲基)丙烯酸酯、三羟甲基丙烷三丙烯酸酯、1,6-己二醇二丙烯酸酯、季戊四醇二、三和四丙烯酸酯和1,12-十二烷二醇二丙烯酸酯;烯-丙烯酸官能团的单体,如甲基丙烯酸烯丙酯、甲基丙烯酸2-烯丙氧羰基氨基乙酯和(甲基)丙烯酸2-烯丙基氨基乙酯;2-丙烯酰胺基-2,2-二甲基乙酸烯丙酯;二乙烯基苯;乙烯氧基取代的官能化单体,如(甲基)丙烯酸2-(乙烯氧基)乙酯、3-(乙烯氧基)-1-丙烯、4-(乙烯氧基)-1-丁烯和4-(乙烯氧基)丁基-2-丙烯酰胺基-2,2-二甲基乙酸酯等。
按100重量份粘合剂共聚物固体计,多烯键式不饱和交联剂通常占0.05至约1重量份,优选占0.1至0.5重量份。
也可以利用诸如γ射线或电子束辐射的高能电磁辐射实现交联。在这种情况下,可以不需要另外的交联剂。
共聚之后可以将其它添加剂与所得到的丙烯酸酯或甲基丙烯酸酯共聚物进行共混。例如,可以加入相容的增粘剂和/或增塑剂以协助优化PSA的最终粘性及剥离性能。在所属领域中使用这种增粘剂是常见的,如《压敏粘合剂技术手册》(Donatas著,1982年)中所述。
适用的增粘剂例子包括(但不限于)松香、松香衍生物、多萜树脂、香豆酮-茚树脂等。可加入本发明之粘合剂的增塑剂可选自多种市售的材料。
代表性的增塑剂包括聚氧乙烯芳基醚、己二酸二烷基酯、磷酸2-乙基己基二苯酯、磷酸叔丁基苯基二苯酯、己二酸二(2-乙基己基)酯、甲苯磺酰胺、二苯甲酸二丙二醇酯、聚乙二醇二苯甲酸酯、聚氧丙烯芳基醚、二丁氧基乙氧基乙基缩甲醛和己二酸二丁氧基乙氧基乙酯。当使用上述物质时,每100重量份共聚物当中,优选增粘剂的添加量不超过约50重量份,每100重量份共聚物当中,增塑剂的添加量最多可以为约50重量份。
优选任何添加的增粘剂和/或增塑剂的折射率为至少1.50,从而使其掺入不会降低压敏粘合剂的折射率。可以参考《增塑剂手册》,GeorgeWypych,编著,加拿大安大略省多伦多士嘉堡区ChemTec出版社书号:ISBN 1-895198-29-1,以及参考Wypych和Anna的《增塑剂数据库》(电子版第二版)。ChemTec出版社网络版网址:http://www.knovel.com/knovel2/Toc.jsp?BookID=976&VerticalID=0。
适用的高折射率增塑剂包括芳香族磷酸酯、邻苯二甲酸酯、苯甲酸酯、芳香族氨磺酰以及某些松香。磷酸酯和邻苯二甲酸酯是优选的。典型的增塑剂包括二苯甲酸二乙二醇酯(1.5424 n25/D)、磷酸4-(叔丁基)苯基二苯酯(1.555 n25/D)、磷酸三甲苯酯(1.5545n25/D)、磷酸三苯酯(1.5575 n25/D)、苯甲酸苯甲酯(1.56 n25/D)二苯甲酸二乙二醇酯(1.5424n25/D)、邻苯二甲酸丁基苄酯(1.537 n25/D)、松香甲酯(1.531 n20/D)、邻苯二甲酸烷基苄酯(1.526 n25/D)、丁基(苯磺酰)胺(1.525 n20/D)、邻苯二甲酸苄酯(1.518 n25/D)、偏苯三酸三甲酯(1.523 n20/D)和磷酸2-乙基己基二苯酯(1.51 n20/D)。
此外,对于光学应用来说,增粘剂、增塑剂及其它添加剂应该具有浅颜色,即Gardner值<3,优选Gardner值<1。此外,选择的增塑剂应该是与聚合物基质及聚合介质相容的(即可混溶的)。
为了提高粘合剂组合物的性能,可以加入其它的添加剂。例如,本文中可以包含均化剂、紫外线吸收剂、受阻胺光稳定剂(HALS)、氧抑制剂、润湿剂、流变改性剂、消泡剂、杀生物剂、染料、颜料等。所有这些添加剂及其用途是本领域中所熟知的。应该理解的是,可以使用这些当中的任何化合物,只要它们不会对粘合剂及光学性能产生有害影响就行。
UV吸收剂及受阻胺光稳定剂也适合作为本组合物的添加剂。UV吸收剂及受阻胺光稳定剂的作用是减少UV辐射对最终硫化产物的不良影响,从而提高耐候性或提高对涂层开裂、发黄及分层的抵抗力。优选的受阻胺光稳定剂是双(1,2,2,6,6-五甲基-4-呱啶基)[3,5-双(1,1-二甲基乙基-4-羟苯基)甲基]丁基丙二酸酯,得自纽约州霍桑的汽巴-嘉基公司的TinuvinTM144。
按全部单体组合物计,浓度低于5重量份的以下UV吸收剂及其组合可以产生期望的结果:双(1,2,2,6,6-五甲基-4-呱啶基)(3,5-双(1,1-二甲基乙基-4-羟苯基)甲基)丁基丙二酸酯、2-乙基己基-2-氰基-3,3′-二苯基丙烯酸酯、2-羟基-4-正辛氧基二苯甲酮、2-(2′-羟基-5′-甲苯基)苯并三唑、聚(氧代-1,2-乙二基)、α-(3-(3-(2H-苯并三唑-2-基)-5-(1,1-二甲基乙基)-4-羟苯基)-1-氧丙基)-ω-羟基以及由新泽西州帕西潘尼的BASFWyandotte Inc.出售的Uvinul.RTM.D-50和MS-40。然而,按组合物总重量计,UV吸收剂的浓度在1%至5%范围内是优选的。
可以按任何常规的自由基聚合方法制备本文中的粘合剂共聚物,包括溶液、辐射、本体、分散、乳液及悬浮法。对于光学应用来说,溶液、UV及本体方法是优选的。其它方法可能会引入双折射或可能影响光学性能的杂质。
可以通过如在美国专利No.3,691,140(Silver)、No.4,166,152(Baker等人)、No.4,636,432(Shibano等人)、No.4,656,218(Kinoshita)和No.5,045,569(Delgado)中公开的悬浮聚合法制备粘合剂共聚物。优选在自由基引发剂的存在下通过乳液聚合法制备(甲基)丙烯酸酯聚合物。
适用于制备本发明中使用的(甲基)丙烯酸酯粘合剂共聚物的水溶性和油溶性引发剂是这样的引发剂,当它们暴露于热时产生引发单体混合物(共聚)聚合的自由基。水溶性引发剂是通过乳液聚合制备(甲基)丙烯酸酯聚合物所优选的。合适的水溶性引发剂包括(但不限于):选自过硫酸钾、过硫酸铵、过硫酸钠的那些以及它们的混合物;氧化还原引发剂,如上述过硫酸盐与还原剂(如选自焦亚硫酸钠和亚硫酸氢钠的那些)的反应产物;和4,4′-偶氮二(4-氰基戊酸)及其可溶盐(例如钠盐、钾盐)。优选的水溶性引发剂是过硫酸钾。合适的油溶性引发剂包括(但不限于):选自偶氮化合物的那些,如VAZO 64(2,2′-偶氮二(异丁腈))和VAZO 52(2,2′-偶氮二(2,4-二甲基戊腈)),两者均得自杜邦公司;过氧化物,如过氧化苯甲酰和过氧化月桂酰,以及它们的混合物。优选的油溶性热引发剂是(2,2′-偶氮二(异丁腈))。当使用引发剂时,按压敏粘合剂中100重量份的单体组分计,引发剂可以占约0.05至约1重量份,优选占约0.1至约0.5重量份。
通过乳液技术聚合可能需要存在乳化剂(也可称为乳化试剂或表面活性剂)。适用于本发明的乳化剂包括选自阴离子型表面活性剂、阳离子型表面活性剂、非离子型表面活性剂的那些以及它们的混合物。
优选在阴离子表面活性剂的存在下进行乳液聚合。按乳液压敏粘合剂的所有单体总重量计,表面活性剂的适用浓度范围是约0.5至约8重量%,优选为约1至约5重量%。
作为另外的选择,共聚物的聚合方法可以包括(但不限于)常规的溶剂聚合、分散聚合及无溶剂本体聚合。单体混合物可以包含聚合引发剂,特别是热引发剂或光引发剂,其类型及数量能有效地使共聚单体聚合,如前所述。
典型的溶液聚合法通过以下步骤进行:向反应容器中加入单体、合适的溶剂和可选的链转移剂,加入自由基引发剂,用氮吹扫,使反应容器保持在高温,通常在约40至100℃范围内,直到反应完成,根据批量大小和温度条件,这通常需约1至20小时。溶剂的例子有甲醇、四氢呋喃、乙醇、异丙醇、丙酮、甲基乙基酮、乙酸甲酯、乙酸乙酯、甲苯、二甲苯和乙二醇烷基醚。这些溶剂可单独使用或作为混合物使用。
在典型的光聚合方法中,可以在光聚合引发剂(即,光引发剂)的存在下用紫外(UV)线照射单体混合物。优选的光引发剂是以商品名IRGACURE和DAROCUR得自纽约州达里镇的汽巴特种化学品公司的那些,包括1-羟基环己基苯基甲酮(IRGACURE 184)、2,2-二甲氧基-1,2-二苯乙-1-酮(IRGACURE 651)、双(2,4,6-三甲基苯甲酰基)苯基氧化膦(IRGACURE 819)、1-[4-(2-羟乙氧基)苯基]-2-羟基-2-甲基-1-丙烷-1-酮(IRGACURE 2959)、2-苄基-2-二甲氨基-1-(4-吗啉代苯基)丁酮(IRGACURE 369)、2-甲基-1-[4-(甲硫基)苯基]-2-吗啉代丙-1-酮(IRGACURE 907)和2-羟基-2-甲基-1-苯基丙-1-酮(DAROCUR 1173)。特别优选的光引发剂是IRGACURE 819、651、184和2959。
无溶剂聚合法,如美国专利No.4,619,979和No.4,843,134(Kotnour等人)中所述的连续自由基聚合法;基本上绝热的聚合方法,使用美国专利No.5,637,646(Ellis)中所述的间歇式反应器;和美国专利No.5,804,610(Hamer等人)中所述的用于使包封的预粘合剂组合物聚合的方法,上述的方法也可用来制备所述的聚合物。
可以采用常规的涂布技术将本发明的粘合剂涂布到多种柔性和刚性的背衬材料上,从而制备涂有粘合剂的材料。柔性基材在本文中的定义为常规用作胶带背层的任何材料或者可以为任何其它的柔性材料。其例子包括(但不限于)塑料膜,如聚丙烯、聚乙烯、聚氯乙烯、聚酯(聚对苯二甲酸乙二醇酯)、聚碳酸酯、聚(甲基)丙烯酸甲酯(PMMA)、乙酸纤维素、三乙酸纤维素和乙基纤维素。刚性基材的例子包括(但不限于)金属、金属化聚合物膜、氧化铟锡镀膜玻璃及聚酯、PMMA板、聚碳酸酯板、玻璃或陶瓷片材。涂粘合剂的片材可以是按常规已知为使用粘合剂组合物的任何制品的形式,如标签、条带、标牌、覆盖件、标记刻度、显示元件、触摸屏等。
采用常规的涂布技术,根据具体的基材进行酌情改动,由此把上述组合物涂布到基材上。例如,可以通过诸如辊涂、流涂、浸涂、旋涂、喷涂、刮涂和压模涂布的方法把这些组合物施加到多种固体基材上。通过这些不同的涂布方法可将组合物以可变厚度的方式设置到基材上,从而使组合物具有较宽的应用范围。涂层厚度是可以变化的,但可设想2-500微米、优选为约25至250微米的涂层厚度(干厚度)。
粘合剂乳液(含粘合剂共聚物和水)可以具有后续涂布所需的任意浓度,但通常含30重量%至70重量%的水,更典型地含50重量%至65重量%的水。通过进一步稀释乳液或者通过进行部分干燥达到所需的浓度。
实例
参考以下非限制性实例及测试方法进一步描述本发明。除非另有规定,所有的份数、百分数和比例均为按重量计。
聚合方法
可以通过常规的自由基聚合法和适当的活性自由基聚合法制备压敏粘合剂。合适的聚合方法包括溶液聚合、悬浮聚合、乳液聚合及本体聚合。使用如下的组分:
表I:组分
乳液聚合:一般工序
可以按表III中所示的量将所有组分加入到500ml烧杯中并进行混合,直到水相和有机相均匀。然后可以在韦林氏混合器中均化混合物2分钟,从而制备用于聚合的乳液。可以把乳液放入玻璃瓶中,并且用氮吹扫除氧。可以将瓶密封并放入旋转水浴中以使聚合反应基本完成。聚合之后,可以通过粗滤布过滤乳胶,从而在涂布和评价之前除去凝结物。可以把聚合物乳胶涂布到37微米(1.5密耳)的聚酯膜上,从而得到约25微米(~1密耳)厚度的干涂层。可以对涂布的膜进行平衡,此后按粘附力测试方法所述在约23℃和50%相对湿度的条件下进行测试。可以用平衡的膜来测定折射率。
本体聚合:一般工序
可以在250ml玻璃瓶中混合表IV中所示量的单体组分,向玻璃瓶中加入IRGACURE 651(全部单体重量的0.2%)。可以彻底地混合瓶中的成分,并且用氮吹扫除氧。使用刮刀涂布机可以把混合物涂布成在打底漆的38微米(1.5密耳)聚酯膜与隔离衬片之间约50-80微米(~2-3密耳)的厚度。可以利用莹光性黑光下的紫外线辐射(约680毫焦耳/平方厘米)使所得到的涂层聚合,此后按粘附力测试方法所述在约23℃和50%相对湿度的条件下进行测试。如上所述,可以用平衡的膜来测定折射率。
测试方法
用于评价实例中涂布PSA的柔性片材的测试方法是行业标准测试。标准测试描述在美国材料试验协会(ASTM)(宾夕法尼亚州费城)和压敏胶带理事会(PSTC)的各种出版物中。
剥离粘附力(ASTM D3330-78PSTC-1(11/75))
剥离粘附力是从试板上取下涂布的柔性片材所需的力,测量是在特定的角度和移取速度下进行的。在实例中,以每100mm宽涂片的牛顿数(N/100mm)表示此力。遵循的工序是:
1.把12.7mm宽的涂片施加到干净的玻璃试板的水平面上,至少有12.7cm线状的牢固接触。使用2kg的硬橡皮辊施加所述条。
2.将涂布条的自由端对折成几乎接触到自身,这样使移取角度为180°。使自由端附着于粘附力测定仪盘。
3.把玻璃试板夹在拉伸试验机的狭口中,所述拉伸试验机能够以每分钟0.3米的恒速将所述板移离所述盘。
4.当条带从玻璃表面上剥离时记录盘上的读数(牛顿)。给出的数据为测试期间观察到的数字范围的平均值。
折射率的测量
使用由日本东京爱尔玛株式会社制造、飞世尔科技经销的阿贝折射计测量粘合剂的折射率。
玻璃化转变(T
g
)的测量
使用由美国特拉华州纽卡斯尔的TA仪器公司制造的差示扫描量热计(DSC)Q200仪器测量热活化粘合剂的Tg。
雾度的测量
可以按ASTM D1003,用BYK Gardner分光光度计测量粘合剂膜的雾度和透射度并记录为A2*值,其表示在钨丝灯(在约2854K的相关温度下操作)光下的雾度。
制备例1
合成6-咔唑-9-基-己-1-醇:
向500ml三颈圆底烧瓶中加入25克咔唑、218克二甲基甲酰胺、45.5克碳酸钾和43克6-氯-1-己醇。反应混合物在150℃加热6小时,冷却到室温。加入500克乙酸乙酯,用250克水洗,然后用250克水与50克浓HCl洗,然后用250克饱和盐水洗。用旋转蒸发器除去溶剂以得到58克棕色的半固体。使用硅胶快速色谱柱纯化粗产物,以二氯甲烷为洗脱液。浓缩产物部分得到33.3克白色固态产物;气相色谱纯度~90%。
合成丙烯酸6-咔唑-9-基-己酯):
向500ml三颈圆底烧瓶中加入33克6-咔唑-9-基-己-1-醇、170克甲苯、2.2克PTSA、10.7克丙烯酸和0.07克对苯二酚单甲醚(MEHQ)。加热回流混合物,通过使用Dean-Stark分水器进行共沸蒸馏除去水。五小时的回流之后,另加入1克丙烯酸,再加热混合物一小时。使反应混合物冷却到室温,用HCl的5%水溶液100克进行洗涤,然后用碳酸钠的10%水溶液100克进行洗涤,然后用100克饱和盐水进行洗涤。用旋转蒸发器除去溶剂。
使用硅胶快速色谱柱纯化粗产物,以氯仿为洗脱液。浓缩产物部分得到24克透明液体产物,气相色谱纯度>99%。通过GC/MS确定准确的单体分子量。单体的折射率为1.5905,均聚物Tg为45℃。
制备例2。
合成8-咔唑-9-基-辛-1-醇:
向250ml圆底烧瓶中加入10克咔唑、90克二甲基甲酰胺、18.2克碳酸钾和20.6克8-氯辛醇。将反应混合物加热到150℃达六个小时,然后冷却到室温。加入200克乙酸乙酯,反应混合物用200克水进行洗涤,用200克水与10克浓HCl进行洗涤,然后用150克饱和盐水溶液洗涤三次。减压去除溶剂以得到~30克黄色油,通过柱色谱法纯化,得到18克8-咔唑-9-基-辛-1-醇。
合成丙烯酸8-咔唑-9-基-辛酯:
向250ml圆底烧瓶中加入17.5克上述产物、80克甲苯、5.1克丙烯酸、0.04克MEHQ和1.0克对甲苯磺酸(PTSA)。加热回流混合物,通过使用Dean-Stark分水器进行共沸蒸馏除去水。六个小时以后反应达到室温,照例进行洗涤。脱除溶剂得到~17克黄色油。采用柱色谱法纯化,得到7克GC纯度>96%的丙烯酸8-咔唑-9-基-辛酯单体。单体的折射率为1.5830,均聚物Tg为23℃。
溶液聚合:一般程序
按表I中所示的量称出所有的组分放入到具有120克容量的玻璃瓶中。以每分钟1升的流速用氮吹扫5分钟,由此对瓶中的成分进行除氧。将瓶密封并在60℃的旋转水浴中放置24小时以使聚合反应基本完成。向聚合物溶液中进一步加入按固体计0.10份的双酰胺为交联剂,由此制备粘合剂膜。把聚合物溶液涂布到37微米(1.5密耳)聚酯膜上,从而得到25微米(~1密耳)厚度的干涂层。在70℃烘箱中加热干燥10分钟后,对涂布膜进行平衡,此后按粘附力测试方法所述,在约23℃和50%相对湿度的条件下进行测试。用平衡的膜来测量折射率。
Claims (5)
2.根据权利要求1所述的粘合剂,其中所述共聚物还包含c)酸官能团的单体单元。
3.根据权利要求1所述的粘合剂,其还包含交联剂。
4.根据权利要求1所述的粘合剂,其包含具有以下单体单元的共聚物
a)5至95重量份的所述具有咔唑侧基的单体单元;
b)95至5重量份的所述(甲基)丙烯酸烷基酯单体单元;
c)0至15重量份的酸官能团的单体单元;
d)0至15重量份的极性单体单元;和
e)0至5重量份的其它单体单元,
其中单体单元的总和为100重量份;和
任选的增塑剂。
5.根据权利要求4所述的粘合剂,其包含具有以下单体单元的共聚物
a)10至90重量份的具有咔唑侧基的单体单元;
b)90至10重量份的(甲基)丙烯酸烷基酯单体单元;
c)1至15重量份的酸官能团的单体单元;
d)0至15重量份的极性单体单元;和
e)0至5重量份的其它单体单元,
其中单体单元的总和为100重量份;和
任选的增塑剂。
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- 2008-10-03 WO PCT/US2008/078740 patent/WO2009058513A1/en active Application Filing
- 2008-10-03 EP EP08843534.2A patent/EP2207860B1/en not_active Not-in-force
- 2008-10-03 US US12/738,090 patent/US8309650B2/en active Active
- 2008-10-03 KR KR1020107011775A patent/KR101545365B1/ko active IP Right Grant
- 2008-10-03 CN CN200880122445XA patent/CN101910348B/zh not_active Expired - Fee Related
- 2008-10-03 JP JP2010532106A patent/JP5596549B2/ja not_active Expired - Fee Related
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1189181A (zh) * | 1995-06-26 | 1998-07-29 | 美国3M公司 | 光漫射粘合剂 |
CN1284106A (zh) * | 1998-01-27 | 2001-02-14 | 美国3M公司 | 不发白的乳液压敏粘合剂 |
Also Published As
Publication number | Publication date |
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EP2207860B1 (en) | 2016-02-10 |
US20100222496A1 (en) | 2010-09-02 |
WO2009058513A1 (en) | 2009-05-07 |
CN101910348A (zh) | 2010-12-08 |
KR20100101588A (ko) | 2010-09-17 |
KR101545365B1 (ko) | 2015-08-18 |
JP2011502202A (ja) | 2011-01-20 |
US8309650B2 (en) | 2012-11-13 |
EP2207860A1 (en) | 2010-07-21 |
JP5596549B2 (ja) | 2014-09-24 |
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