CN116917386A - 近红外(nIR)敏化的粘合剂和密封剂组合物 - Google Patents
近红外(nIR)敏化的粘合剂和密封剂组合物 Download PDFInfo
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- CN116917386A CN116917386A CN202280016923.9A CN202280016923A CN116917386A CN 116917386 A CN116917386 A CN 116917386A CN 202280016923 A CN202280016923 A CN 202280016923A CN 116917386 A CN116917386 A CN 116917386A
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- near infrared
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- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 description 1
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- C08G59/4078—Curing agents not provided for by the groups C08G59/42 - C08G59/66 boron containing compounds
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- C08G65/22—Cyclic ethers having at least one atom other than carbon and hydrogen outside the ring
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Abstract
本发明涉及一种可光固化的粘合剂或密封剂组合物,所述组合物基于该组合物的重量,包含:1至10wt.%的a)至少一种根据下式(I)的氧杂环丁烷化合物:其中:R1和R2为H、C1‑C6烷基、C6‑C18芳基或C7‑C18芳烷基;各R3独立地为C1‑C12亚烷基、C6‑C18亚芳基、C2‑C12亚烯基或聚(C1‑C6亚烷氧基)基团;以及,n为1至3的整数;5至20wt.%的b)至少一种环氧化物,其中组分b)的特征在于环氧化物的总重量的至少50wt.%是由b1)至少一种脂环族环氧化物构成;0.1至5wt.%的c)至少一种离子型光酸产生剂;0至10wt.%的d)至少一种自由基光引发剂;0.01至5wt.%的e)至少一种近红外吸收染料;以及,50至90wt.%的f)颗粒填料。
Description
技术领域
本发明涉及粘合剂和密封剂组合物,其可用于光电子和光机械器件。更具体地,本发明涉及基于氧杂环丁烷和脂环族环氧化物单体的近红外(nIR)敏化的粘合剂和密封剂组合物。
背景技术
已发现可辐射固化材料可用作涂料、粘合剂和密封剂。这种用途在一定程度上是由这类材料在固化过程中的典型低能耗以及材料即使在较低温度下通过自由基或阳离子机理的快速固化速度推动的。这些材料通常也可以配制成无溶剂组合物,在应用时提供减少挥发性有机化合物排放的潜力。这些优点使得可辐射固化材料特别适用于快速粘合和密封对温度敏感或不能方便地承受长固化时间的电子和光电子器件。特别是,光电子器件通常是热敏感的,并且可能需要在非常短的时间内通过固化来光学对准和空间固定。
许多光电子器件也是对湿气或氧气敏感的,在其功能寿命期间需要保护以免暴露。一种常见的方法是将器件密封在不可渗透的基材(器件设置在其上)和不可渗透的玻璃或金属盖之间,然后使用可辐射固化的粘合剂或密封剂将盖的周边密封或粘附到底部基材上。用于此目的的有效阻隔密封剂将表现出低的本体透湿性(bulk moisturepermeability)、良好的粘合性和强的界面粘合剂-基材相互作用。
在基材与密封剂界面的质量较差的情况下,该界面可能起到弱边界的作用,其允许湿气进入器件,而与密封剂的本体透湿性无关。在界面至少与本体密封剂一样连续的情况下,湿气渗透将由密封剂本身的本体透湿性决定。在实践中,用于光电子或光机械应用的粘合剂或密封剂的固化基质必须具有高交联密度、微结晶度或基质的交联部分之间的分子主链的紧密堆积:基质的有限分子迁移率确保低的渗透迁移率或扩散率。
本领域通常关注固化材料的玻璃化转变温度(Tg)作为该用途的量度;密封剂和粘合剂被配制以产生高于所需的Tg值,从而提供合适的容许度(tolerance)。当然,满足高Tg标准可能意味着在拉伸强度、搭接剪切强度、粘合强度和模量等方面进行折衷。但是,除此之外,为了满足这样的热标准,重要的是在整个所施用的粘合剂或密封剂材料中完成固化,特别是阴影固化有效地延伸到所施用的材料的未被入射启动光源照射的区域中。阴影区域中的不充分固化使光电子器件的部件暴露于腐蚀的风险,并且还可能对内部光路产生不期望的影响。因此,为了避免阴影固化不充分的问题,通常配制粘合剂或密封剂除了可辐射固化之外,还表现出热固化或湿固化。
US2008/272328(Kong)公开了一种用于光电子器件的阳离子可固化的阻隔组合物,所述组合物基本上由以下组成:(a)氧杂环丁烷化合物;(b)阳离子引发剂;(c)任选存在的一种或多种填料;和(d)任选存在的一种或多种增粘剂,或一种或多种环氧树脂。阳离子引发剂的用量并不决定在光化辐射照射下的固化速率。对于所公开的组合物中环氧树脂与氧杂环丁烷的测试比例,最佳固化条件包括高于130℃的温度。
US2005061429A1(Hosaka)公开了一种光化辐射可固化的粘合剂,其基于组合物的重量包含:50至99wt.%的双官能和/或多官能氧杂环丁烷化合物;0至40wt.%的单官能氧杂环丁烷化合物;1至50wt.%的具有环状结构的环氧化合物;以及催化量的光引发剂。该引文声称仅需要将所施用的组合物暴露于光化辐射以完全固化。然而,应注意的是,固化后组合物的凝胶点在室温下可长达30分钟:这可能不适合于那些需要更快速地固化粘合剂的应用。在这种情况下,技术人员必须采用升高的固化温度。
US2003062125A1(Takamatsu等人)公开了一种光阳离子可固化的树脂组合物,其可用作液晶显示器或电致发光显示器的密封剂,该组合物包含:(a)阳离子可聚合的化合物;(b)光阳离子引发剂;和(c)芳族醚化合物或脂族硫醚化合物。示例的组合物在高强度金属卤化物灯照射下固化,但组分单体没有完全转化。
DE102009012272A1(Wellmann)公开了一种用于光机械和光电子器件的双固化粘合剂,所述粘合剂组合物包含:至少一种单体的、UV固化的粘合剂组分;至少一种光引发剂;具有游离异氰酸酯基团的组分或含有游离硅烷的组分;以及伯胺、仲胺和/或叔胺。
本发明人认为,本领域需要提供可用于光电子器件的可光固化的粘合剂或密封剂组合物,该组合物在用光化辐射照射该组合物之后不需要热固化步骤就基本上可以固化。希望开发在仅暴露于光化辐射时不表现出有害的低玻璃化转变温度(Tg)的组合物。
发明内容
根据本发明的第一方面,提供一种可光固化的粘合剂或密封剂组合物,所述组合物基于该组合物的重量,包含:
1至10wt.%的a)至少一种根据下式(I)的氧杂环丁烷化合物:
其中:R1和R2为H、C1-C6烷基、C6-C18芳基或C7-C18芳烷基;
各R3独立地为C1-C12亚烷基、C6-C18亚芳基、C2-C12亚烯基或聚(C1-C6亚烷氧基)基团;以及
n为1至3的整数;
5至20wt.%的b)至少一种环氧化物,其中组分b)的特征在于环氧化物的总重量的至少50wt.%是由b1)至少一种脂环族环氧化物构成;
0.1至5wt.%的c)至少一种离子型光酸产生剂;
0至10wt.%的d)至少一种自由基光引发剂;
0.01至5wt.%的e)至少一种近红外吸收染料;以及
50至90wt.%的f)颗粒填料。
在一个实施方案中,所述可光固化的粘合剂或密封剂组合物基于该组合物的重量,包含:
5至10wt.%的a)所述至少一种根据式(I)的氧杂环丁烷化合物;
5至15wt.%的b)所述至少一种环氧化物;
0.1至5wt.%的c)所述至少一种离子型光酸产生剂(PAG);
0.1至10wt.%的d)所述至少一种自由基光引发剂;
0.01至1wt.%的e)所述至少一种近红外吸收染料;以及
50至80wt.%的f)颗粒填料。
近红外吸收染料的存在促进了本申请在暴露于近红外(nIR)辐射时的固化。虽然这种nIR辐射可单独用于固化,但也可在nIR辐射之前、同时或之后用其它光化辐射照射组合物。在这样的固化条件下,本发明的固化的粘合剂或密封剂应具有最小的残余焓,并表现出高的单体转化率,例如大于85%的单体转化率。此外,在测试中,该组合物显示出有利的固化深度,而不需要热固化步骤。
根据本发明的第二方面,提供一种粘合结构,其包含:第一材料层;和第二材料层,其中经固化的如上文和所附权利要求中定义的粘合剂组合物设置在所述第一材料层和第二材料层之间并与所述第一材料层和第二材料层接触。
本发明还提供上文和所附权利要求中定义的粘合剂或密封剂组合物在光电子或光机械器件中的用途。
定义
如本文所使用,单数形式“一”及“该”包括复数指示物,除非上下文另有明确指示。
本文所用的术语“包含”与“包括”、“含有”同义,并且是包含性的或开放式的,并不排除另外的、未列举的构件、元件或方法步骤。
如本文所用,术语“由……组成”不包括未指定的任何元素、成分、构件或方法步骤。
当数量、浓度、尺寸和其它参数以范围、优选范围、上限值、下限值或优选的上限值和下限值的形式表示时,应当理解,通过将任何上限或优选值与任何下限或优选值组合而获得的任何范围也被具体公开,而不管所获得的范围是否在上下文中被明确提及。
此外,根据标准理解,表示为“0至x”的重量范围具体包括0wt.%:由所述范围定义的成分可以不存在于组合物中,或者可以以高达x wt.%的量存在于组合物中。
本文中频繁使用词语“优选的”、“优选地”、“期望地”及“特别地”是指在某些情况下可提供特定益处的本发明的实施方案。然而,一个或多个优选的、期望的或特定的实施方案的叙述并不意味着其它实施方案是无用的,并不旨在将那些其它实施方案排除在本公开的范围之外。
如本申请通篇所使用的,“可以”一词是在许可的意义上使用的,意思是有可能-而不是在强制的意义上。
如本文所用,室温为23℃±2℃。如本文所用,“环境条件”是指组合物所处的环境或涂层或所述涂层的基材所处的环境的温度和压力。
在本说明书中提及的分子量-描述可固化组合物的大分子、低聚物和聚合物组分-可以使用聚苯乙烯校准标准物通过凝胶渗透色谱法(GPC)测量,例如根据ASTM 3536进行。
除非另有规定,否则本文所述的涂料组合物的粘度是使用流变仪在20℃和50%相对湿度(RH)的标准条件下测量的。流变仪的校准方法将根据制造商的说明来选择,以适合于待测量的组合物。
如本文所用,“平均粒径(D50)”是指对应于分布曲线中50%的颗粒的粒径,在分布曲线中,颗粒以粒径从最小颗粒到最大颗粒的顺序累积,并且累积的颗粒总数为100%。
当提及时,聚合物或共聚物的计算的玻璃化转变温度(“Tg”)是可以通过使用Fox方程(T.G.Fox,Bull.Am.Physics Soc.,Volume 1,Issue No.3,page 123(1956))计算的温度。某些均聚物的玻璃化转变温度可以在已出版的文献中找到。
聚合物的实际玻璃化转变温度(Tg)可通过动态机械热分析(Dynamic MechanicalThermal Analysis,DMTA)测定。在本专利申请中具体测量的玻璃化转变温度(Tg)是根据国际标准化组织(International Organization for Standardization,ISO)标准ISO6721-1和ISO6721-11的方法通过DMTA测量的。
如本文所用,“近红外(nIR)辐射”是指波长为700至1500nm的电磁辐射,例如由激光器或发光二极管(LED)发射的电磁辐射。这种近红外辐射的一个非限制性实例是由二极管激光器发射的光,该二极管激光器配备有直接制版机(plate-setters),并且可从Creo-Kodak、Dinippon Screen、Heidelberg和Presstek International获得。nIR辐射的其他示例性来源为可从Phoseon Technology Inc.获得的FireJetTM和FireEdgeTM LED灯。关于本发明的组合物,可以注意到优选用波长为780至980nm的nIR辐射进行照射。
如本文所用,“近红外(nIR)吸收染料”是在700nm至1500nm的波长范围内具有显著光吸收性的化合物、络合物或分子。
本文所用的术语“单体”是指可以进行聚合反应以向聚合物的化学结构贡献结构单元的物质。本文所用的术语“单官能”是指具有一个可聚合部分。本文所用的术语“多官能团”是指具有超过一个的可聚合部分。
如本文所用,术语“当量(eq.)”涉及反应中存在的反应性基团的相对数目,这在化学符号中是常见的。术语“毫当量”(meq)是指化学当量的千分之一(10-3)。
本文所用的术语“当量重量”是指分子量除以所涉及的官能团的数目。因此,“环氧当量重量”(EEW)是指含有1当量环氧树脂的树脂重量,以克为单位:该参数可通过ShellAnalytical Method HC427D-89使用高氯酸滴定法测定。
本文的氧杂环丁烷和环氧化物经历“开环聚合”,其是指其中环状化合物(单体)在适当的催化剂存在下开环形成线性聚合物的聚合。反应体系趋向于所需的所得高分子化合物、环状化合物混合物和/或线性低聚物之间的平衡,该平衡的实现很大程度上取决于环状单体的性质和量、所用的催化剂和反应温度。不推荐在聚合中使用溶剂和/或乳液,因为一旦反应完成,它们的去除可能很复杂。
如本文所用,术语“环氧化物”表示特征为存在至少一个环状醚基团的化合物,即其中醚氧原子连接到两个相邻碳原子上从而形成环状结构的化合物。该术语旨在包括单环氧化物、多环氧化物(具有两个或更多个环氧化物基团)和环氧化物封端的预聚物。术语“单环氧化物”是指具有一个环氧基的环氧化物。术语“多环氧化物”是指具有至少两个环氧基的环氧化物。术语“二环氧化物”表示具有两个环氧基的环氧化物。
环氧化物可以是未取代的,但也可以是惰性取代的。示例性的惰性取代基包括氯、溴、氟和苯基。
本文所用的术语“光引发剂”是指可被载能活化束例如电磁辐射活化的化合物,例如在用其照射时。该术语旨在包括自由基光引发剂以及光酸产生剂和光碱产生剂。具体而言,术语“光酸产生剂”是指在暴露于光化辐射时产生用于催化酸硬化树脂体系的酸的化合物或聚合物。术语“光碱产生剂”是指当暴露于适当的辐射时产生一种或多种碱的任何材料。
本文所用的术语“路易斯酸”表示能够通过与来自第二分子或离子的两个电子形成共价键而与另一分子或离子结合的任何分子或离子,通常称为亲电体:因此路易斯酸是电子受体。
如本文所用,“C1-Cn烷基”是指含有1至n个碳原子的一价基团,其为烷烃基团,并包括直链和支链有机基团。因此,“C1-C18烷基”是指含有1至18个碳原子的一价基团,其为烷烃基团,并包括直链和支链的有机基团。烷基的实例包括,但不限于:甲基;乙基;丙基;异丙基;正丁基;异丁基;仲丁基;叔丁基;正戊基;正己基;正庚基;以及2-乙基己基。在本发明中,这种烷基可以是未取代的,或可以被一个或多个卤素取代。在适用于给定部分(R)的情况下,在说明书中将注明对烷基内的一个或多个非卤素取代基的容限。
本文所用的术语“C1-C6羟烷基”是指具有1至6个碳原子的HO-(烷基)基团,其中取代基的连接点是通过氧原子,且烷基如上文所定义。
“烷氧基”是指由-OA表示的一价基团,其中A为烷基:其非限制性实例是甲氧基、乙氧基和异丙氧基。本文所用的术语“C1-C18烷氧基烷基”是指具有如上定义的烷氧基取代基的烷基,其中该部分(烷基-O-烷基)总共包含1至18个碳原子:这种基团包括甲氧基甲基(-CH2OCH3)、2-甲氧基乙基(-CH2CH2OCH3)和2-乙氧基乙基。
本文所用的术语“C1-C12亚烷基”定义为具有1至12个碳原子的饱和二价烃基。进一步地,术语“C1-C6亚烷氧基”是指二价基团-R-O-,其中R为C1-C6亚烷基。
术语“C3-C18环烷基”应理解为是指具有3至18个碳原子的饱和的单环或多环烃基。在本发明中,这种环烷基可以是未取代的,或者可以被一个或多个卤素取代。当适用于给定的部分(R)时,在说明书中将指出在环烷基内的一个或多个非卤素取代基的容限。环烷基的实例包括:环丙基;环丁基;环戊基;环己基;环庚基;环辛基;金刚烷;以及降冰片烷。
本文所用的“C6-C18芳基”基团单独使用或作为较大部分的一部分使用,是指单环、双环和三环体系,其中单环体系是芳族的,或者双环或三环体系中的至少一个环是芳族的。双环和三环体系包括苯并稠合的2-3元碳环。在本发明中,这种芳基可以是未取代的,或可以被一个或多个卤素取代。在适用于给定部分(R)的情况下,在说明书中将指出芳基内的一个或多个非卤素取代基的容限。示例性的芳基包括:苯基;茚基;萘基、四氢萘基、四氢茚基;四氢蒽基。
本文所用的术语“C6-C18亚芳基”是指具有6至18个碳原子的二价基团,其衍生自单环、双环和三环体系,其中单环体系是芳族的,或者双环或三环体系中的至少一个环是芳族的。亚芳基可以被至少一个卤素取代基取代,但亚芳基的芳族部分仅包括碳原子。示例性的“C6-C18亚芳基”包括亚苯基和萘-1,8-二基。
本文所用的术语“芳氧基”表示O-芳基,其中芳基如上文所定义。在本发明中,这种芳氧基可以是未取代的,或可以被一个或多个卤素取代。
术语“芳烷基”是指其中如上所定义的芳基取代如上所定义的烷基的至少一个氢原子的基团。为了完整性,这种芳烷基可以是未取代的,或可以被一个或多个卤素取代。
本文所用的术语“亚芳烷基”是指其中芳基取代上述亚烷基的至少一个氢原子的二价基团。亚芳烷基可以被至少一个卤素取代基取代。
如本文所用,“烷芳基”是指烷基取代的芳基。此外,术语“亚烷芳基”表示为烷基取代的芳基二价基团,其中在烷基碳主链的任何位置的一个氢被另外的结合位点取代。亚烷芳基的实例包括甲基亚苯基和乙基亚苯基。
本文所用的“芳烷氧基”是通过芳烷基的烷基部分上的氧取代基连接到化合物上的芳烷基。示例性的芳烷氧基为苯基甲氧基和苯基乙氧基。
本文所用的“C2-C24烯基”是指具有2至24个碳原子和至少一个烯键式不饱和单元的烃基。烯基可以是直链的、支链的或环状的,并且可以任选地被一个或多个卤素取代。在适用于给定部分(R)的情况下,说明书中将注明烯基内一个或多个非卤素取代基的容限。如本领域普通技术人员所理解的,术语“烯基”还包括具有“顺式”和“反式”构型,或者具有“E”和“Z”构型的基团。然而,通常应注意优选含有2至10个(C2-10)或2至8个(C2-8)碳原子的未取代烯基。所述C2-C12烯基的实例包括,但不限于:—CH═CH2;—CH═CHCH3;—CH2CH═CH2;—C(═CH2)(CH3);—CH═CHCH2CH3;—CH2CH═CHCH3;—CH2CH2CH═CH2;—CH═C(CH3)2;—CH2C(═CH2)(CH3);—C(═CH2)CH2CH3;—C(CH3)═CHCH3;—C(CH3)CH═CH2;—CH═CHCH2CH2CH3;—CH2CH═CHCH2CH3;—CH2CH2CH═CHCH3;—CH2CH2CH2CH═CH2;—C(═CH2)CH2CH2CH3;—C(CH3)═CHCH2CH3;—CH(CH3)CH═CHCH;—CH(CH3)CH2CH═CH2;—CH2CH═C(CH3)2;1-环戊-1-烯基;1-环戊-2-烯基;1-环戊-3-烯基;1-环己-1-烯基;1-环己-2-烯基;以及1-环己基-3-烯基。
本文所用的“C2-C12亚烯基”是指具有2至24个碳原子和至少一个烯键式不饱和单元的二价自由基。亚烯基可以是直链的、支链的或环状的,并且可以任选地被一个或多个卤素取代。当适用于给定的部分(R)时,说明书中将注明在亚烯基内的一个或多个非卤素取代基的容限。如本领域普通技术人员所理解的,术语“亚烯基”还包括具有“顺式”和“反式”构型,或者具有“E”和“Z”构型的基团。所述C2-C12烯基的实例包括,但不限于:亚乙烯基;乙烯-1,1-二基;亚丙烯基;丙烯-1,1-二基;丙-2-烯-1,1-二基;1-甲基-亚乙烯基;丁-1-亚烯基;丁-2-亚烯基;丁-1,3-亚二烯基;丁烯-1,1-二基;丁-1,3-二烯-1,1-二基;丁-2-烯-1,1-二基;丁-3-烯-1,1-二基;1-甲基-丙-2-烯-1,1-二基;2-甲基-丙-2-烯-1,1-二基;1-乙基-亚乙烯基;1,2-二甲基-亚乙烯基;1-甲基-亚丙烯基;2-甲基-亚丙烯基;3-甲基-亚丙烯基;2-甲基-丙烯-1,1-二基;以及2,2-二甲基-乙烯-1,1-二基。
本文所用的术语“杂”是指含有一个或多个杂原子如N、O、Si和S的基团或部分。因此,例如“杂环”是指具有例如N、O、Si或S作为环结构的一部分的环状基团。“杂烷基”、“杂环烷基”和“杂芳基”部分分别为上文定义的烷基、环烷基和芳基分别含有N、O、Si或S作为其结构的一部分。
本发明的组合物在本文中可定义为“基本上不含”某些化合物、元素、离子或其它类似组分。术语“基本上不含”意指化合物、元素、离子或其它类似组分不是有意添加到组合物中的,并且最多仅以痕量存在,其对涂层的所需性能没有(不利)影响。示例性的痕量为小于组合物重量的1000ppm。术语“基本上不含”包括其中特定化合物、元素、离子或其它类似组分在组合物中完全不存在或不以本领域通常使用的技术可测量的任何量存在的那些实施方案。
具体实施方式
a)氧杂环丁烷化合物
本发明的组合物,基于该组合物的重量,包含1至10wt.%的a)至少一种根据下式(I)的氧杂环丁烷化合物:
其中:R1和R2为H、C1-C6烷基、C6-C18芳基或C7-C18芳烷基;
各R3独立地为C1-C12亚烷基、C2-C12亚烯基或聚(C1-C6亚烷氧基)基团;以及
n为1至3的整数。
基于组合物的重量,该组合物可以例如包含5至10wt.%的a)所述至少一种根据式(I)的氧杂环丁烷化合物。
在本发明的一个实施方案中,该组合物可包含式(IA)的氧杂环丁烷
其中:R1和R2如上文所定义。
在该实施方案中,可优选R1和R2为C1-C6烷基。尽管R1和R2可以相同或不同,但优选它们是相同的。式IA的示例性化合物为双[1-乙基-3-氧杂环丁烷基)甲基]醚。
在本发明的另一个实施方案中,该实施方案并不旨在与上面给出的实施方案相互排斥,该组合物可以包含式(IB)的氧杂环丁烷化合物:
其中:R1、R2和R3如上文所定义。
在该实施方案中,优选:R1和R2为C1-C6烷基;且R3为C1-C6亚烷基。例如:R1和R2相同并且为C1-C4烷基;且R3为C1-C4亚烷基。式(IAA)的示例性化合物为1,4-双[(3-乙基-3-氧杂环丁烷基甲氧基)甲基]苯。
b)环氧化物
基于组合物的重量,本发明的组合物包含5至20wt%的b)至少一种环氧化物。基于组合物的重量,该组合物可以例如包含5至15wt.%的b)所述至少一种环氧化物。如上所述,基于组合物中环氧化物的总重量,至少50wt.%是由b1)至少一种脂环族环氧化物构成。认为b1)所述至少一种脂环族环氧化物可以合理地构成所述组分b)的至少65wt.%,甚至100wt.%。
b1)脂环族环氧化物
组合物中所含的所述或每种脂环族环氧化物包含至少一个环氧基,其可以是以下形式:末端环氧基;缩水甘油醚(例如-O-CH2-环氧化物);或者与C5-7环烷基稠合的环氧化物。
示例性的脂环族环氧化物包括:单环氧基取代的脂环族烃,例如环己烯氧化物、乙烯基环己烯一氧化物、(+)-顺式-柠檬烯氧化物、(+)-顺式-反式-柠檬烯氧化物、(-)-顺式-反式-柠檬烯氧化物、环辛烯氧化物、环十二碳烯氧化物和α-蒎烯氧化物;乙烯基环己烯二环氧化物;柠檬烯二环氧化物;脂环族醇的缩水甘油醚;脂环族单羧酸的缩水甘油酯;脂环族二醇例如环戊二醇和环己二醇的二缩水甘油醚;以及脂环族多羧酸的缩水甘油酯,所述酸含有至少两个羧酸基团并且没有与环氧化物基团反应的其它基团。
在无意限制本发明的情况下,合适的脂环族环氧树脂包括:环己烷二甲醇二缩水甘油醚;双(3,4-环氧环己基甲基)己二酸酯;双(3,4-环氧基-6-甲基环己基甲基)己二酸酯;双(2,3-环氧环戊基)醚;3,4-环氧环己基甲基-3',4'-环氧环己基甲酸酯;1,4-环己烷二甲醇二缩水甘油醚;1,2-环己烷二羧酸二缩水甘油酯;双(2,3-环氧丙基)环己烷-1,2-二羧酸酯;以及通过芳族双酚A二缩水甘油醚(BADGE)环氧树脂的氢化获得的脂环族环氧树脂。
优选脂环族环氧包含两个C5-6环烷基,其中每个独立地稠合到环氧化物上,例如双(3,4-环氧环己基甲基)己二酸酯、双(3,4-环氧基-6-甲基环己基甲基)己二酸酯、双(2,3-环氧环戊基)醚或3,4-环氧环己基甲基-3',4'-环氧环己基甲酸酯。
作为市售脂环族环氧化物,可以提及:UVR6105、UVR6107、UVR6110和UVR6128,其可获自Dow Chemical;Syna Epoxy S-06E,其可获自Synasia;以及Celloxide2021P,其可获自Daicel Corporation。
b2)脂族和芳族环氧化物
除了必须存在的脂环族树脂之外,本发明的组合物可以任选地包含b2)至少一种另外的环氧化物。本文所用的所述另外的环氧化物可包括单官能环氧树脂、多(multi-)或多(poly-)官能环氧树脂及其组合。环氧树脂可以是纯化合物,但同样可以是环氧官能化合物的混合物,包括每分子具有不同数目的环氧基团的化合物的混合物。所述另外的环氧树脂可以是饱和的或不饱和的、脂族的、芳族的或杂环的,并且可以是取代的。此外,环氧树脂也可以是单体的或聚合的。
在无意限制本发明的情况下,示例性的非脂环族单环氧化物包括:烷氧化物;环氧取代的芳烃;一元醇或酚的单环氧取代的烷基醚,例如脂族和芳族醇的缩水甘油醚;一元羧酸的单环氧取代的烷基酯,例如脂族和芳族一元羧酸的缩水甘油酯;多羧酸的单环氧取代的烷基酯,其中其它羧基被链烷醇酯化;环氧基取代的一元羧酸的烷基和烯基酯;多元醇的环氧烷基醚,其中其它OH基团用羧酸或醇酯化或醚化;以及多元醇和环氧一元羧酸的单酯,其中其它OH基团被羧酸或醇酯化或醚化。
例如,下列缩水甘油醚可作为特别适用于本发明的单环氧化物:甲基缩水甘油醚;乙基缩水甘油醚;丙基缩水甘油醚;丁基缩水甘油醚;戊基缩水甘油醚;己基缩水甘油醚;辛基缩水甘油醚;2-乙基己基缩水甘油醚;烯丙基缩水甘油醚;苄基缩水甘油醚;苯基缩水甘油醚;4-叔丁基苯基缩水甘油醚;1-萘基缩水甘油醚;2-萘基缩水甘油醚;2-氯苯基缩水甘油醚;4-氯苯基缩水甘油醚;4-溴苯基缩水甘油醚;2,4,6-三氯苯基缩水甘油醚;2,4,6-三溴苯基缩水甘油醚;五氟苯基缩水甘油醚;邻甲苯基缩水甘油醚;间甲苯基缩水甘油醚;以及对甲苯基缩水甘油醚。
在一个实施方案中,单环氧化物符合下述式(II):
其中:R7、R8、R9和R10可以相同或不同,并且独立地选自氢、卤素原子、C1-C8烷基、C2-C12烯基、C6-C18芳基或C7-C18芳烷基,条件是R8和R9中的至少一个不是氢。
优选R7、R8和R10为氢,R9为苯基或C1-C8烷基,更优选C1-C4烷基。
关于该实施方案,示例性的单环氧化物包括:环氧乙烷;1,2-环氧丙烷(环氧丙烷);1,2-环氧丁烷;顺-2,3-环氧丁烷;反式-2,3-环氧丁烷;1,2-环氧戊烷;1,2-环氧己烷;1,2-环氧庚烷;环氧癸烷;氧化丁二烯;氧化异戊二烯;以及氧化苯乙烯。
同样,在无意限制本发明的情况下,可用作组分b2)的合适的多环氧化物可以是液体、固体或在溶剂中的溶液。此外,这种多环氧化物应具有100至700g/eq,例如120至320g/eq的环氧当量重量。并且通常,优选具有小于500g/eq或甚至小于400g/eq的环氧当量重量的二环氧化物:这主要是从成本的角度考虑,因为在它们的生产中,较低分子量的环氧树脂在纯化中需要更有限的处理。
作为可以在本发明中聚合的多环氧化物的类型或组别的实例,可以提及:多元醇和多元酚的缩水甘油醚;多元羧酸的缩水甘油酯;以及环氧化的多烯键式不饱和烃、酯、醚和酰胺。
合适的二缩水甘油醚化合物在性质上可以是芳族的或脂族的,并且因此可衍生自二元酚和二元醇。并且这种二缩水甘油醚的有用类别是:脂族二醇例如1,2-乙二醇、1,4-丁二醇、1,6-己二醇、1,8-辛二醇和1,12-十二烷二醇的二缩水甘油醚;双酚A基二缩水甘油醚;双酚F二缩水甘油醚;邻苯二甲酸二缩水甘油酯、间苯二甲酸二缩水甘油酯和对苯二甲酸二缩水甘油酯;聚亚烷基二醇基二缩水甘油醚,特别是聚丙二醇二缩水甘油醚;以及聚碳酸酯二醇基缩水甘油醚。也可提及的其它合适的双环氧化物包括:双不饱和脂肪酸C1-C18烷基酯的双环氧化物;丁二烯二环氧化物;以及聚丁二烯二缩水甘油醚。
其它示例性的多环氧化物包括但不限于:甘油多缩水甘油醚;三羟甲基丙烷多缩水甘油醚;季戊四醇多缩水甘油醚;二甘油多缩水甘油醚;聚甘油多缩水甘油醚;以及山梨醇多缩水甘油醚。
在本发明中有用的多元羧酸的缩水甘油酯衍生自含有至少两个羧酸基团且不含与环氧基团反应的其它基团的多元羧酸。多元羧酸可以是脂肪族的、芳香族的和杂环的。优选的多元羧酸是每个羧酸基团含有不超过18个碳原子的那些,其合适的实例包括但不限于:草酸;癸二酸;己二酸;琥珀酸;庚二酸;辛二酸;戊二酸;不饱和脂肪酸的二聚酸和三聚酸,例如亚麻籽脂肪酸的二聚酸和三聚酸;邻苯二甲酸;间苯二甲酸;对苯二甲酸;偏苯三甲酸;均苯三甲酸;亚苯基二乙酸;氯菌酸;联苯二甲酸;萘二甲酸;二元酸和脂族多元醇的多元酸封端酯;(甲基)丙烯酸的聚合物和共聚物;以及巴豆酸。
多环氧化物的示例性实例包括:双酚A环氧树脂,立如DERTM331、DERTM332、DERTM383、JERTM 828和Epotec YD 128;双酚F环氧树脂,例如DERTM354;双酚A/F环氧树脂混合物,例如DERTM353;脂肪族缩水甘油醚,例如DERTM736;聚丙二醇二缩水甘油醚,例如DERTM732;固体双酚A环氧树脂,例如DERTM661和DERTM664UE;双酚A固体环氧树脂溶液,例如DERTM671-X75;环氧酚醛树脂,例如DENTM438;环氧化酚醛清漆树脂,例如Epalloy 2850;溴化环氧树脂,例如DERTM542;蓖麻油三缩水甘油醚,例如ERISYSTMGE-35H;聚甘油-3-多缩水甘油醚,例如ERISYSTMGE-38;以及山梨醇缩水甘油醚,例如ERISYSTMGE-60。
除了上述之外,在某些实施方案中,组合物的组分b)应包含具有下式的缩水甘油氧基烷基烷氧基硅烷:
其中:各R独立地选自甲基或乙基;以及,
n为1-10。
示例性的硅烷包括但不限于:γ-缩水甘油氧基丙基三甲氧基硅烷、γ-缩水甘油氧基乙基三甲氧基硅烷、γ-缩水甘油氧基甲基三甲氧基硅烷、γ-缩水甘油氧基甲基三乙氧基硅烷、γ-缩水甘油氧基乙基三乙氧基硅烷、γ-缩水甘油氧基丙基三乙氧基硅烷;以及8-缩水甘油氧基辛基三甲氧基硅烷。基于环氧化物的总重量,环氧化物官能硅烷当存在时,应占少于20wt.%,优选少于10wt.%或少于5wt.%。
本发明也不排除可固化组合物进一步包含一种或多种选自以下组中的环状单体:环状碳酸酯;环酐;以及内酯。以下引文的公开对于公开合适的环状碳酸酯官能化合物可能是有指导意义的:美国专利号3,535,342;美国专利号4,835,289;美国专利号4,892,954;英国专利号GB-A-1,485,925;以及,EP-A-0 119 840。然而,基于环氧化物b)的总重量,这种环状共聚单体应占少于20wt.%,优选少于10wt.%或少于5wt.%。
c)离子型光酸产生剂
基于组合物的重量,本发明的组合物包含0.1至5wt%的c)至少一种离子型光酸产生剂(PAG)。在用光能照射时,离子型光酸产生剂发生裂解反应并释放一个或多个路易斯酸或布朗斯台德酸分子,其催化侧链的氧杂环丁烷和环氧基团的开环和加成以形成交联。有用的光酸产生剂是热稳定的,不与形成的共聚物发生热诱导反应,并且容易溶解或分散在可固化组合物中。
可用作本发明的离子型PAG的阳离子部分的示例性阳离子包括有机鎓阳离子,例如美国专利号4,250,311、美国专利号3,113,708、美国专利号4,069,055、美国专利号4,216,288、美国专利号5,084,586、美国专利号5,124,417、以及美国专利号5,554,664中描述的那些。这些参考文献具体包括脂族或芳族IVA和VIIA族(CAS版本)中心的鎓盐,优选以I-、S-、P-、Se-、N-和C-为中心的鎓盐,例如选自氧化锍(sulfoxonium)、碘鎓(iodonium)、锍(sulfonium)、硒鎓(selenonium)、吡啶鎓(pyridinium)、碳鎓(carbonium)和鏻(phosphonium)的那些。
如本领域已知的,离子型光酸产生剂(PAG)中的抗衡阴离子的性质可影响环氧基团的阳离子加成聚合的速率和程度,例如,在常用的亲核阴离子中反应性的顺序是SBF6>ASF6>PF6>BF4。阴离子对反应性的影响归因于本领域技术人员在本发明中应当补偿的三个主要因素:(1)所产生的质子酸或路易斯酸的酸度;(2)增长的阳离子链中离子对分离的程度;以及(3)阴离子对氟化物夺取和随后的链终止的敏感性。
作为可用于本发明组合物的离子型光酸产生剂的实例,可以提及:IrgacureTM250、IrgacureTM PAG 290和GSID26-1,其可获自BASF SE;CyracureTM UVI-6990和CyracureTM UVI-6974,其可获自Union Carbide;DegacureTM Kl 85,其可获自Degussa;OptomerTM SP-55、OptomerTM SP-150和OptomerTM SP-170,其可获自Adeka;GE UVE 1014,其可获自General Electric;以及,SarCatTM CD 1012、SarCatTM KI-85、SarCatTM CD 1010和CD SarCatTM 1011,其可获自Sartomer。
d)自由基光引发剂
本发明的组合物可以任选地进一步包括自由基光引发剂。例如,基于组合物的重量,组合物可包含0至10wt%的d)至少一种自由基光引发剂,该化合物在用光化辐射照射时引发组合物的聚合或硬化。该组合物可以例如包含0.1至10wt.%或0.1至8wt.%的所述自由基光引发剂。
通常,自由基光引发剂分为通过裂解形成自由基的那些,称为“Norrish I型”,和通过夺氢形成自由基的那些,称为“Norrish II型”。Norrish II型光引发剂需要作为自由基源的氢供体:由于引发是基于双分子反应,Norrish II型光引发剂通常比基于自由基的单分子形成的Norrish I型光引发剂慢。另一方面,Norrish II型光引发剂在近紫外光谱区具有更好的光吸收性能。本领域技术人员应该能够基于固化中使用的光化辐射和光引发剂在该波长下的敏感性来选择合适的自由基光引发剂。
优选的自由基光引发剂选自以下组中:苯甲酰基膦氧化物;芳基酮;二苯甲酮;羟基化酮;1-羟基苯基酮;缩酮;以及茂金属。为了完整性,在本发明中不排除这些光引发剂中的两种或更多种的组合。
特别优选的自由基光引发剂是选自以下组中的那些:安息香二甲醚;1-羟基环己基苯基酮;二苯甲酮;4-氯二苯甲酮;4-甲基二苯甲酮;4-苯基二苯甲酮;4,4'-双(二乙氨基)二苯甲酮;4,4'-双(N,N'-二甲氨基)二苯甲酮(米氏酮(Michler's ketone));异丙基噻吨酮;2-羟基-2-甲基苯丙酮(Daracur 1173);2-甲基-4-(甲硫基)-2-吗啉代苯丙酮;苯乙醛酸甲酯;2-苯甲酰基苯甲酸甲酯;过氧苯甲酸叔丁酯;4-(二甲基氨基)苯甲酸2-乙基己酯;4-(N,N-二甲基氨基)苯甲酸乙酯;苯基双(2,4,6-三甲基苯甲酰基)氧化膦;二苯基(2,4,6-三甲基苯甲酰基)氧化膦;以及苯基(2,4,6-三甲基苯甲酰基)次膦酸乙酯。同样,为了确保,在本发明中不排除这些光引发剂中的两种或更多种的组合。
考虑到本发明的组合物包含自由基光引发剂,所述可固化组合物的辐照从引发固化反应的光引发剂产生活性物质。一旦产生这种物质,固化化学就受到与任何化学反应相同的热力学规则的影响:反应速率可以通过加热来加速。使用热处理来增强单体的光化辐射固化的实践通常是本领域已知的。
在本发明中使用阳离子的和任选的自由基光引发剂可在最终固化产物中由(光)化学反应产生残留化合物。残留物可以通过常规分析技术检测,例如:红外、紫外和NMR光谱;气相或液相色谱;以及质谱。因此,本发明可包括固化的基质(共)聚合物和来自阳离子的自由基光引发剂的可检测量的残留物。残留物以少量存在,并且通常不干扰最终固化产物的所需物理化学性质。
如本领域技术人员所认识到的,可以将光敏剂掺入到组合物中,以提高光引发剂(这里为组分c)和d))使用所提供的能量的效率。术语“光敏剂”根据其标准含义用于表示增加光引发聚合的速率或移动聚合发生的波长的任何物质。基于组合物中光引发剂的总重量,光敏剂的用量应为0至25wt.%。
e)近红外吸收染料
本发明的组合物包含至少一种近红外吸收染料,该染料应当以足以强烈吸收活化辐射的浓度存在。给定的近红外吸收染料的必要或优选浓度将根据染料化合物本身和也存在的光酸产生剂(PAG)而变化。然而,基于组合物的重量,组合物通常包含0.01至5wt.%,例如0.1至1wt.%的所述近红外吸收染料。
本领域技术人员将知晓许多近红外吸收染料。在本文中,优选使用那些在与所述至少一种光酸产生剂(PAG)组合时是非活性的和未漂白的,但在暴露于活化辐射时漂白的染料。示例性的近红外吸收染料包括但不限于:亚硝基化合物及其金属络合盐;次甲基染料;菁染料;部花青染料;复合菁染料;复合部花青染料;全极菁染料;半菁染料;苯乙烯类染料;半氧杂菁染料(hemioxonol dye);方酸染料(squarilium dye);硫醇镍络盐,包括钴、铂和钯络盐;酞菁染料;三烯丙基甲烷染料;三苯甲烷染料;吲哚染料,包括其硼酸盐络合物;呫吨染料;荧光素染料;rhodol染料;罗丹明染料;亚铵染料(immonium dye);二铵染料;萘醌染料;蒽醌染料;卟啉衍生物染料;以及硼二吡咯甲烷(BODIPY)染料。
特别可提及下列染料,其可单独或组合使用:3,3′-二乙基硫代三碳菁碘化物(“DTTC”);1,1'-二乙基-4,4'-碳菁碘化物(隐花青);吲哚菁绿(ICG);非磺化菁染料,例如花青5(Cy5)、花青5.5(Cy5.5)、花青7(Cy7)和花青7.5(Cy7.5),可获自LumiProbe;磺化菁染料,例如磺基花青5(Cy5)和磺基花青7(Cy7),可获自Lumiprobe Fluorescein;S0772四氟硼酸吲哚染料,可获自Few Chemicals(λmax=858nm);S2514(CAS No.2173178-46-4),可获自Few Chemicals;亚甲蓝;cypate;cypate-葡糖胺;硅罗丹明;5-氨基乙酰丙酸(5-ALA);以及,700、/>750、/>800CW和/>800RS,可获自Li-Cor。
f)颗粒填料
基于组合物的重量,本发明的组合物包含50至90wt.%的f)颗粒填料。基于组合物的重量,组合物可以例如包含50至80wt.%或60至80wt.%的颗粒填料。
所形成的可固化组合物的所需粘度可由所用填料的量决定。考虑到后一种情况,填料的总量不应妨碍组合物通过所选择的将组合物施用于基材的方法而易于施用。例如,旨在通过印刷或注射施用于特定场所的本发明的可光固化的组合物应具有1000至50000,优选10000至20000mPas的粘度。
从广义上讲,没有特别的意图来限制用作填料的颗粒的形状:针状、球形、椭圆形、圆柱形、珠状、立方体或片状的颗粒可以单独使用或组合使用。此外,设想可以使用多于一种颗粒类型的团聚体。同样,没有特别的意图来限制用作填料的颗粒粒径。然而,通过激光衍射/散射法测量,这种填料将通常具有0.1-1000μm,例如1-500μm的平均粒径(D50)。
示例性填料包括但不限于石墨、炭黑、碳酸钙、氧化钙、氯化钙、氢氧化钙(石灰粉)、硫酸钙、熔融二氧化硅、无定形二氧化硅、沉淀和/或热解硅酸、沸石、膨润土、硅灰石、碳酸镁、硫酸镁、硅藻土、硫酸钡、氧化钡、氧化铝、氮化铝、氮化硼、粘土、滑石、氧化钛、氧化铁、氧化锌、沙子、石英、燧石、云母、玻璃珠、玻璃粉和其他研磨的矿物质。也可以使用有机填料,特别是木纤维、木粉、锯末、纤维素、棉花、纸浆、棉花、木屑、切碎的稻草、谷壳、磨碎的胡桃壳和其它切碎的纤维:也可以使用聚(四氯乙烯)、聚(氯三氟乙烯)和聚(偏二氯乙烯)粉末。还可以加入短纤维如玻璃纤维、玻璃长丝、聚丙烯腈、碳纤维、凯夫拉尔纤维或聚乙烯纤维。
具有矿物壳或塑料壳的空心球也适合作为填料。这些可以是例如以商品名Glass在商业上可获得的中空玻璃球。可以使用塑料基空心球,例如/>或并在EP 0520426B1中进行了描述:它们由无机或有机物质组成,且各自具有1mm或更小,优选500μm或更小的直径。
也不排除使用核壳橡胶颗粒作为填料。术语“核壳橡胶”或CSR根据其在本领域中的标准含义使用,表示由包含弹性体或橡胶状聚合物作为主要成分的聚合物形成的橡胶颗粒核和由接枝聚合到所述核上的聚合物形成的壳层。壳层在接枝聚合过程中部分或全部覆盖橡胶颗粒核的表面。按重量计,核应构成核壳橡胶颗粒的至少50wt.%。
核壳橡胶可选自市售产品,其实例包括:Paraloid TMS-2670J、EXL 2650A、EXL2655和EXL2691A,可获自The Dow Chemical Company;XT100,可获自Arkema Inc.;Kane/>MX系列,可获自Kaneka Corporation,特别是MX 120、MX 125、MX130、MX 136、MX 551、MX553;以及,METABLEN SX-006,可获自Mitsubishi Rayon。
赋予组合物触变性的填料对于许多应用可能是优选的:这种填料也被描述为流变助剂,例如氢化蓖麻油、脂肪酸酰胺或可膨胀塑料如PVC。
在本发明的一个实施方案中,组合物的组分e)包含无定形二氧化硅颗粒或由无定形二氧化硅颗粒组成,该无定形二氧化硅颗粒的平均粒径(d50)通过激光衍射/散射方法测量为5-100μm,例如5-50μm。为了说明的目的,可以提及使用以商品名Denka FB销售的商业级无定形二氧化硅。
添加剂和辅助成分
本发明中获得的所述组合物通常还包含可赋予这些组合物改进性能的助剂和添加剂。例如,助剂和添加剂可以赋予一种或多种以下性质:改善的弹性;改善的弹性恢复;更长的启用处理时间(enabled processing time);更快的固化时间;以及,更低的残余粘性。这些助剂和添加剂包括:增韧剂;增塑剂;稳定剂,包括UV稳定剂;抗氧化剂;反应性稀释剂;干燥剂或除湿剂;粘合促进剂;杀菌剂;阻燃剂;流变助剂;彩色颜料或色浆;和/或任选地,少量的非反应性稀释剂。
这种助剂和添加剂可以以所需的组合和比例使用,只要它们不对组合物的性质和基本性能产生不利影响。尽管在某些情况下可能存在例外,但这些助剂和添加剂的总量不应超过总组合物的30wt.%,优选不应超过组合物的15wt.%。
本发明的“增塑剂”是指降低组合物粘度从而促进其可加工性的物质。本文中,基于组合物的总重量,增塑剂可以占至多10wt.%或至多5wt.%,并且优选选自以下组中:二氨基甲酸酯;单官能的直链或支链C4-C16醇的醚,例如Cetiol OE(可获自CognisDeutschland GmbH,Düsseldorf);松香酸、己二酸、癸二酸、丁酸、硫代丁酸、乙酸、丙酸和柠檬酸的酯;基于硝化纤维素和聚乙酸乙烯酯的酯;脂肪酸酯;二羧酸酯;带OH基团的或环氧化的脂肪酸的酯;乙醇酸酯;苯甲酸酯;磷酸酯;磺酸酯;偏苯三酸酯;聚醚增塑剂,例如封端的聚乙二醇或聚丙二醇;聚苯乙烯;烃类增塑剂;氯化石蜡;及其混合物。注意,原则上邻苯二甲酸酯可用作增塑剂,但由于其潜在的毒性而不是优选的。
用于本发明目的的“稳定剂”应理解为抗氧化剂、UV稳定剂、热稳定剂或水解稳定剂。在本文中,基于组合物的总重量,稳定剂可以总共占至多10wt.%或至多5wt.%。适用于本文的稳定剂的标准商业实例包括:空间位阻酚;硫醚;苯并三唑;二苯甲酮;苯甲酸酯;氰基丙烯酸酯;丙烯酸酯;受阻胺光稳定剂(HALS)类型的胺;磷;硫磺;及其混合物。
尽管在上面的组分b中)提到了使用环氧官能硅烷,但还应注意,具有金属螯合性能的化合物可用于本发明的组合物中,以帮助增强固化的粘合剂对基材表面的粘合性。此外,还适合用作粘合促进剂的是由King Industries以商品名K-FLEX XM-B301销售的乙酰乙酸酯官能化的改性树脂。
在本发明的组合物中也不排除溶剂和非反应性稀释剂的存在,这可以有效地调节其粘度。例如,但仅为举例说明,组合物可包含以下中的一种或多种:二甲苯;2-甲氧基乙醇;二甲氧基乙醇;2-乙氧基乙醇;2-丙氧基乙醇;2-异丙氧基乙醇;2-丁氧基乙醇;2-苯氧基乙醇;2-苄氧基乙醇;苯甲醇;乙二醇;乙二醇二甲醚;乙二醇二乙醚;乙二醇二丁醚;乙二醇二苯醚;二甘醇;二甘醇单甲醚;二甘醇单乙醚;二甘醇单正丁醚;二甘醇二甲醚;二甘醇二乙醚;二甘醇二正丁基醚;丙二醇丁醚;丙二醇苯醚;一缩二丙二醇;一缩二丙二醇单甲醚;一缩二丙二醇二甲醚;一缩二丙二醇二正丁基醚;N-甲基吡咯烷酮;二苯甲烷;二异丙基萘;石油馏分,例如产品(可获自Exxon);烷基苯酚,例如叔丁基苯酚、壬基苯酚、十二烷基苯酚和8,11,14-十五碳三烯基苯酚;苯乙烯化苯酚;双酚;以及,芳香烃树脂,特别是含有酚基的那些,例如乙氧基化或丙氧基化的酚。
除了上述之外,基于组合物的总重量,优选所述非反应性稀释剂总共占小于10wt.%,特别是小于5wt.%或小于2wt.%。
方法和施用
为了形成规定的可固化组合物,将各组分放在一起并混合。重要的是,混合使成分均匀地分布在粘合剂组合物内:这种彻底和有效的混合可以决定固化后获得的聚合物基体中任何组成颗粒填料或其它助剂材料的均匀分布。
如本领域已知的,为了形成可固化的组合物,将组合物的组分放在一起并在抑制或防止反应组分发生反应的条件下均匀混合:这种条件是本领域技术人员容易理解的。因此,通常优选的是,固化成分不是通过手工混合,而是通过机器例如静态或动态混合器以预定量混合,而无需有意的光辐射。
根据本发明的最广泛的工艺方面,将上述组合物施用到材料层上,然后原位固化。在施用组合物之前,通常建议对相关表面进行预处理,以去除其中的异物:如果适用,该步骤可以促进组合物随后粘附到其上。这种处理在本领域中是已知的,并且可以以单阶段或多阶段的方式进行,所述方式由例如使用以下一种或多种构成:用适合于基材的酸和任选存在的氧化剂进行蚀刻处理;超声处理;等离子体处理,包括化学等离子体处理、电晕处理、常压等离子体处理和火焰等离子体处理;在水性碱性脱脂槽中浸渍;用水性清洁乳液处理;用清洁溶剂例如丙酮、四氯化碳或三氯乙烯处理;以及水冲洗,优选用去离子水或软化水冲洗。
在一些实施方案中,本发明的组合物与优选预处理的基材的粘合可以通过向其施加底漆来促进。实际上,底漆组合物可能是必需的,以确保粘合剂组合物在非活性基材上的有效固定和/或固化时间。本领域技术人员将能够选择合适的底漆。
然后通过常规施用方法将组合物施用到任选预处理的、任选涂有底漆的基材表面上,所述施用方法例如:印刷方法,包括丝网印刷;针式转印;以及注射器施用,包括电动气动控制注射器。推荐将组合物以10-700μm的湿膜厚度施加到表面上。在该范围内施加较薄的层是更经济的,并且降低了产生有害的厚固化区域的可能性。然而,在施加较薄的涂层或层时必须进行严格控制,以避免形成不连续的固化膜。
在本发明中,发射近红外(nIR)辐射的能量源必须用于固化所施用的组合物。令人满意地固化单个粘合剂或密封剂组合物使得所述粘合剂或密封剂例如变得固定所需的近红外(nIR)辐射的总量将取决于多种因素,包括暴露于辐射的角度和粘合剂或密封剂层的厚度。然而,从广义上讲,1至20W/cm2的近红外(nIR)辐射的辐照度可以被引用为典型的:1至15W/cm2,例如5至15W/cm2的固化辐照度可以被认为是高度有效的。在它们的应用之后,当使用商业固化设备照射时,可光固化的粘合剂组合物通常可以在少于5分钟内,并且通常在1至60秒内,例如在3至20秒内活化。
以上述方式使用近红外(IR)辐射并不排除使用另外的能量源,其可以发射紫外(UV)辐射、中红外(IR)辐射、远红外(IR)辐射、可见光、X射线、γ射线或电子束(e-束)中的至少一种。在主要的实验室、商业或工业条件下,这种补充辐射可用作实现满意固化的工具,但不认为是必要的。可以在用近红外(IR)辐射照射所施用的组合物之前、期间和/或之后施用补充辐射。
当使用时,照射的紫外光通常应具有150至600nm的波长,优选200至450nm的波长。有用的UV光源包括,例如,超高压汞灯、高压汞灯、中压汞灯、低强度荧光灯、金属卤化物灯、微波灯、氙灯、UV-LED灯和激光束源,例如准分子激光器和氩离子激光器。
在使用电子束来固化所施加的涂层时,操作装置的标准参数可以是:0.1至100keV的加速电压;10至10-3Pa的真空度;0.0001至1安培的电流;以及,0.1瓦至1千瓦的功率。
辐射的目的是从引发固化反应的光引发剂中产生活性物质。一旦产生这种物质,固化化学就受到与任何化学反应相同的热力学规则的影响:反应速率可以通过加热来加速,或者通过较低的温度来减速。无意限制本发明,所施用的可固化组合物的完全固化通常应在20℃至50℃、优选20℃至40℃的温度下发生。在适用的情况下,可使用常规方法(包括微波诱导)将可固化组合物的温度升高至高于混合温度和/或施用温度。
没有特别的意图来限制本发明的粘合剂或密封剂组合物可以应用的基材。本领域技术人员将意识到在光电子器件或光机械器件中常规存在的那些基材。然而,可以参考:聚合物,例如聚氯乙烯、聚烯烃和聚碳酸酯;碳和纳米碳基材;金属,例如Al、Pb、Sn、Ge、Si、Ti、Bi、In、Ni和Fe;阳极化金属,特别是阳极化铝;合金,例如黄铜和不锈钢;半导体材料,例如Si、GaAs、InP、GaP、GaSb和InAs;陶瓷,包括二氧化硅、氧化锆、陶瓷套管、压电陶瓷和介电陶瓷;以及玻璃,包括FTO/ITO玻璃、玻璃-聚合物混合材料和其上用导电层改性的玻璃。
以下实施例是对本发明的说明,并不旨在以任何方式限制本发明的范围。
实施例:
在实施例中使用以下商业化合物:
Celloxide 2021P:3,4-环氧环己基甲基-3',4'环氧环己烷羧酸酯,购自DaicelCorporation。
Epalloy 8250:平均官能度为2.65的环氧化线型酚醛树脂,购自HuntsmanAdvanced Materials。
Oxetane OXT-221:双[1-乙基(3-氧杂环丁烷基)]甲基醚,购自SanyoCorporation。
TMPO:3-乙基-3-氧杂环丁烷甲醇,购自Sanyo Corporation。
Bluesil PI 2074:(甲苯基枯基)碘鎓四(五氟苯基)硼酸盐,购自ElkomSilicones。
Denka FB 35:熔融二氧化硅,球形,购自Denka Company Limited。
Silquest A-187:环氧官能硅烷,购自Momentive Performance Materials。
Cab-O-Sil TS 720:气相二氧化硅,购自Cabot Corporation。
Darocur 1173:2-羟基-2-甲基-1-苯基-丙-1-酮,购自Ciba SpecialtyChemicals。
Benzopicanol:1,1,2,2-四苯基乙烷-1,2-二醇,购自Alfa Aesar。
Trigonox C:叔丁基过氧苯甲酸酯,购自Nouryon。
S2514:Enolate nIR染料,购自Few Chemicals(λmax=825nm,CAS No.2173178-46-4)
Monarch 430:炭黑,购自Cabot Corporation。
根据下表1中提供的组成信息制备制剂A-I。表1和表2中的符号“FM”表示根据本发明的制剂。表1和表2中的符号“CF.”表示对比制剂。
表1
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制剂A-E和G-I的方法学:
在适用的情况下,将nIR染料(S2514)称重到快速混合器的杯中,然后向其中加入TMPO、OXT-221和(在适用的情况下)benzopicanol。将杯在60℃下保持30分钟,然后加入A-187、Darocur 1173、Epalloy 8250(如果适用)和50重量%的Cab-O-Sil 720:手动混合杯中的内容物,然后在2800rpm下快速混合2分钟。加入剩余的Cab-O-Sil 720,再次手动混合内容物,并在2800rpm下快速混合2分钟。分三次加入Denka FB 35,每次加入都需要手动搅拌并在1800rpm下搅拌1分钟。在加入PI2074和(在适用的情况下)Trigonox C之前,使所得混合物冷却。将混合物脱气并在800rpm下快速混合1分钟以除去夹带的空气。
制剂F的方法学:
将A-187、Darocur 1173、TMPO、OXT-221和2021P称重到快速混合器的杯中,然后向其中加入50重量%的Cab-O-Sil 720:手动混合杯中的内容物,然后在2800rpm下快速混合2分钟。加入剩余的Cab-O-Sil 720,再次手动混合内容物,并在2800rpm下快速混合2分钟。加入炭黑,进一步手动混合内容物,并在2800rpm下快速混合2分钟。分三次加入Denka FB 35,每次加入都需要手动搅拌并在1800rpm下搅拌1分钟。在加入PI2074之前,使所获得的混合物冷却。将混合物脱气并在800rpm下快速混合1分钟以除去夹带的空气。
固化评价:通过介电分析(DEA)监测制剂的固化,其中将固定量的每种制剂置于两个电极之间,并在电极上施加相同的正弦交流电压。这产生了电场,该电场使材料中的离子从一个电极迁移到另一个电极。在固化过程中,离子的迁移率和偶极子的旋转将变得更加受限,导致所获得的信号的幅度发生变化。由于离子电导率与离子迁移率有关,而离子迁移率又与材料的粘度有关,因此离子电导率及其倒数值离子粘度是固化过程中粘度变化的良好指标。在该DEA分析中,随着固化的进行,可以获得每个样品的介电常数和损耗因子的介电性质。
在下面的表2中提供了对示例性制剂进行的测试结果。该表还包括进一步的标准测试方法(如适用)。为完整起见,示例性制剂各自通过以下固化:i)将施用的制剂暴露于波长为365nm的辐射下3秒钟,强度为1000mW/cm2;以及ii)随后将所施用的制剂暴露于波长为850nm的辐射下10秒钟,在12W和约5mm的距离下操作。FireJetTM FJ200(购自PhoseonTechnology Inc)用于该辐照步骤。
表2
关于表2,离子粘度的变化越大,获得的固化程度越高。值得注意的是,只有含有nIR染料的制剂在nIR固化过程中变得非常热:认为这种高温反过来促进了高单体转化率。
鉴于前面的描述和实施例,对于本领域技术人员显而易见的是,在不脱离权利要求的范围的情况下,可以对其进行等同的修改。
Claims (12)
1.一种可光固化的粘合剂或密封剂组合物,所述组合物基于该组合物的重量,包含:
1至10wt.%的a)至少一种根据下式(I)的氧杂环丁烷化合物:
其中:R1和R2为H、C1-C6烷基、C6-C18芳基或C7-C18芳烷基;
各R3独立地为C1-C12亚烷基、C6-C18亚芳基、C2-C12亚烯基或聚(C1-C6亚烷氧基)基团;以及
n为1至3的整数;
5至20wt.%的b)至少一种环氧化物,其中组分b)的特征在于环氧化物的总重量的至少50wt.%是由b1)至少一种脂环族环氧化物构成;
0.1至5wt.%的c)至少一种离子型光酸产生剂;
0至10wt.%的d)至少一种自由基光引发剂;
0.01至5wt.%的e)至少一种近红外吸收染料;以及
50至90wt.%的f)颗粒填料。
2.根据权利要求1所述的组合物,所述组合物基于该组合物的重量,包含:
5至10wt.%的a)所述至少一种根据式(I)的氧杂环丁烷化合物;
5至15wt.%的b)所述至少一种环氧化物;
0.1至5wt.%的c)所述至少一种离子型光酸产生剂(PAG);
0.1至10wt.%的d)所述至少一种自由基光引发剂;
0.01至1wt.%的e)所述至少一种近红外吸收染料;以及
50至80wt.%的f)颗粒填料。
3.根据权利要求1或2所述的组合物,其中组分a)包含式(IA)的氧杂环丁烷或由式(IA)的氧杂环丁烷组成:
其中:R1和R2为H、C1-C6烷基、C6-C18芳基或C7-C18芳烷基。
4.根据权利要求3所述的组合物,其中式(IA)中的R1和R2均为C1-C6烷基。
5.根据权利要求3所述的组合物,其中组分a)包含双[1-乙基-3-氧杂环丁烷基]甲基]醚或由双[1-乙基-3-氧杂环丁烷基]甲基]醚组成。
6.根据权利要求1至5中任一项所述的组合物,其中b1)所述至少一种脂环族环氧化物构成所述组分b)的至少65wt.%。
7.根据权利要求1至6中任一项所述的组合物,其中所述脂环族环氧化物选自以下组中:双(3,4-环氧环己基甲基)己二酸酯、双(3,4-环氧基-6-甲基环己基甲基)己二酸酯、双(2,3-环氧环戊基)醚、3,4-环氧环己基甲基-3',4'-环氧环己基甲酸酯及其混合物。
8.根据权利要求1至7中任一项所述的组合物,其中组分b)包含至少一种具有下式的缩水甘油氧基烷基烷氧基硅烷:
其中:各R独立地选自甲基或乙基;以及
n为1-10,优选为1-8。
9.根据权利要求1至8中任一项所述的组合物,其中所述组合物中的所述近红外吸收染料或每种近红外吸收染料是不与所述至少一种光酸产生剂反应的。
10.根据权利要求1至9中任一项所述的组合物,其中组分f)包含无定形二氧化硅颗粒或由无定形二氧化硅颗粒组成,所述无定形二氧化硅颗粒具有5至100μm,优选5至50μm的平均粒径(d50),所述平均粒径是通过激光衍射测量的。
11.根据权利要求1至10中任一项所述的粘合剂或密封剂组合物在光电子或光机械器件中的用途。
12.一种粘合结构,其包含:
第一材料层;和
第二材料层;
其中经固化的如权利要求1至10中任一项所述的粘合剂组合物设置在所述第一材料层和第二材料层之间并与所述第一材料层和第二材料层接触。
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