CN114746470B - 基于环氧树脂的单组分(1k)组合物 - Google Patents
基于环氧树脂的单组分(1k)组合物 Download PDFInfo
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- CN114746470B CN114746470B CN202080084076.0A CN202080084076A CN114746470B CN 114746470 B CN114746470 B CN 114746470B CN 202080084076 A CN202080084076 A CN 202080084076A CN 114746470 B CN114746470 B CN 114746470B
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- meth
- acrylamide
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- -1 mercapto compound Chemical class 0.000 claims abstract description 96
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical group NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims abstract description 54
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Abstract
本发明涉及一种单组分(1K)组合物,基于所述组合物的重量,其包含:30至90重量%的a)至少一种环氧树脂;1至50重量%的b)至少一种具有至少两个对环氧化物有反应性的巯基的巯基化合物;0.5至25重量%的c)至少一种选自叔胺的一价阳离子的四取代硼酸盐的有机硼化合物;以及,0.5至25重量%的d)至少一种式(VII)的(甲基)丙烯酰胺单体:其中:Ra是H或Me;G选自–NH2、–NHRb和–N(Rb)(Rc);Rb和Rc独立地选自C1‑C18烷基、C1‑C18羟烷基、C1‑C18烷基烷氧基、C6‑C18芳基和–(CH2)n–N(Rd)(Re);n为1至4的整数;并且,Rd和Re独立地选自H和C1‑C6烷基。
Description
技术领域
本发明涉及基于环氧树脂的单组分(1K)组合物。更具体地,本发明涉及包含环氧树脂、巯基化合物、有机硼酸盐化合物和丙烯酰胺单体的单组分组合物。
背景技术
主要地在树脂、改性剂和交联剂(或固化剂)的特定选择可以允许调节固化环氧树脂的特性以实现特定的性能特征的基础上,发现环氧树脂的广泛应用范围。
该多功能性是公认的,恰当固化的环氧树脂还具有多种其他属性,尤其包括:优异的耐化学性,特别是对碱性环境的耐性;高拉伸和压缩强度;高疲劳强度;低固化收缩率;以及电绝缘特性及其在老化或环境暴露后的保持性。
快速固化环氧树脂配制物的现有技术包括环氧树脂和固化剂,由于组合物在混合后和使用前的保存期限极其有限,环氧树脂和固化剂通常以双组分(2K)组合物的形式出现。然而,认识到单组分环氧树脂组合物的开发将消除与使用双组分(2K)组合物相关的原位计量、共混和脱气的不便。
由于环氧树脂和硬化剂或固化剂包装在一起的事实,单组分(1K)组合物必须表现出潜伏性固化:在普通的储存和运输条件下固化不能开始,而是必须延迟直至组合物暴露到特定的固化条件例如高温。
根据一种常规方法,单组分(1K)环氧组合物可以包含一种或多种固体固化剂在环氧树脂中的悬浮体,该固化剂由于它们在环氧树脂基质中的低溶解度而具有潜伏性。这种方法的实例尤其记录在:美国专利号3,519,576;美国专利号3,520,905;以及美国专利号4,866,133。多种基于环氧-双氰胺的单组分组合物已经商业化:例如,WO 2014/165423(AirProducts and Chemicals Inc.)描述了一种单组分组合物,其包含:至少一种叔胺盐,所述盐是至少一种羧酸和至少一种选自以下的叔胺的产物:N–羟乙基哌啶、N–羟乙基吗啉、1,4–双(2–羟乙基)哌嗪、1–乙基哌啶、N,N–二甲基环己烷和二甲基乙醇胺;至少一种环氧树脂;以及,至少一种双氰胺。
有问题的是,基于使用这种固体颗粒硬化剂的体系往往具有高粘度和相对长固化时间的限制。此外,组合物中颗粒硬化剂的任何不均匀分布都可能导致所形成的产品中的未固化区域。并且这些已确定的问题已导致许多作者寻求使固化剂在单组分组合物中的分布均匀化。例如,日本专利公开No.2004-27159描述了一种单组分环氧树脂组合物,其中液体酚树脂主要与固体潜伏性固化剂组合用作固化剂:而该组合物旨在提供优异的储存稳定性,使用液体酚树脂作为主要固化剂会降低固化树脂的物理强度。
其他作者试图溶解双氰胺,在这方面可能要注意:美国专利号4,859,761;美国专利号4,621,128;美国专利号3,420,794;以及EP 2 180 012 A1。
代替使用颗粒固化剂,化学封端已被认为是缓和硬化剂潜伏性的替代方法。其实例可见于US 2007/149727(Okuhira等人),其中改性胺表现出低固化效率,因为交联依赖于亚胺基团水解以产生胺。此外,EP 2 999 730 A(Inst.für Textil und FaserforschungDekendorf Deustche)描述了受保护的N–杂环卡宾,其在惰性条件下储存时在室温下稳定数天。然而,例如所示例的那些的受保护的官能团的开发可能是复杂且不经济的。
因此,认为在本领域中仍然需要开发稳定的单组分液体环氧树脂体系,其提供快速固化、良好加工性,理想地以低固化温度为特征,和经济制造的组合。
发明内容
根据本发明的第一方面,提供一种单组分(1K)组合物,基于所述组合物的重量,其包含:
30至90重量%、优选40至80重量%的a)至少一种环氧树脂;
1至50重量%、优选5至40重量%的b)至少一种具有至少两个对环氧化物有反应性的巯基的巯基化合物;
0.5至25重量%、优选1至20重量%的c)至少一种选自叔胺的一价阳离子的四取代硼酸盐的有机硼化合物;
0.5至25重量%、优选1至20重量%的d)至少一种式(VII)的(甲基)丙烯酰胺单体:
其中:
Ra是H或Me;
G选自–NH2、–NHRb和–N(Rb)(Rc);
Rb和Rc独立地选自C1-C18烷基、C1-C18羟烷基、C1-C18烷基烷氧基、C6-
C18芳基和–(CH2)n–N(Rd)(Re);
n为1至4的整数;及
Rd和Re独立地选自H和C1-C6烷基。
该液体组合物的进一步特征可以在于环氧反应性基团与环氧基团的摩尔比为0.05:1至0.95:1,例如0.25:1至0.85:1。
如上定义的液体组合物在室温下表现出良好的储存稳定性。此外,如上定义的液体组合物可以有利地在低于120℃的高温下在可行的持续时间内固化。
在一个实施方案中,组合物的b)部分包含硫代羧酸的至少一种聚酯。特别地,b)部分可以包含至少一种选自以下的巯基化合物:季戊四醇四巯基乙酸酯(PETMP)、三羟甲基丙烷三巯基乙酸酯(TMPMP)、以及乙二醇二巯基乙酸酯。
盐c)的阴离子理想地是四(C1-C6烷基)硼酸根、四苯基硼酸根或取代的四苯基硼酸根阴离子:可以提及对四苯基硼酸根的偏好。虽然盐c)的一价阳离子可以是四烷基铵离子,但优选的是阳离子是杂环部分——其可以是单环、双环或多环——其中带电荷的氮原子是杂脂族或杂芳族环体系的一部分。因此,在一个特定实施方案中,组合物的c)部分包含环脒鎓四取代硼酸盐和/或咪唑鎓四取代硼酸盐。例如,当c)部分包含至少一种选自以下的盐时可以获得良好的结果:咪唑鎓四苯基硼酸盐、甲基咪唑鎓四苯基硼酸盐、2–乙基–4–甲基咪唑鎓四苯基硼酸盐、2–乙基–1,4–二甲基咪唑鎓四苯基硼酸盐、8–苄基–1,8–二氮杂双环[5.4.0]十一碳–7–烯鎓四苯基硼酸盐、1,8–二氮杂双环[5.4.0]十一碳–7–烯四苯基硼酸盐、以及1,5–二氮杂双环[4.3.0]–壬–5–烯四苯基硼酸盐。
根据本发明的第二方面,提供一种由如上文和所附权利要求中定义的单组分(1K)组合物获得的固化产物。
本发明的另一方面提供如上文和所附权利要求中定义的固化反应产物作为涂料、密封剂或粘合剂的用途。
定义
如本文中所用,单数形式“一个(a)”、“一种(an)”和“该(the)”包括复数指代物,除非上下文另外明确指出。
如本文中所用,术语“包含(comprising)”、“包含(comprises)”和“包含(comprised of)”与“包括(including)”、“包括(includes)”、“含有(containing)”或“含有(contains)”同义,并且是包括性的或开放式的,并且不排除其他非引用的成员、元素或方法步骤。
如本文中所用,术语“由……组成”排除了未指定的任何元素、成分、成员或方法步骤。
在量、浓度、尺寸和其他参数以范围、优选范围、上限值、下限值或优选的上下限值的形式表示时,应理解不论是否在上下文中明确提及所获得的范围,还具体公开了通过将任何上限值或者优选值与任何下限值或优选值结合可获得的任何范围。
此外,按照标准理解,表示为“从0”的重量范围具体包括0重量%:由所述范围定义的成分可以或可以不存在于组合物中。
词语“优选的”、“优选地”、“理想地”和“特别地”通常用于指代在某些情况下可以提供特定益处的本公开的实施方案。然而,一个或多个更好的、优选的、理想的或特别的实施方案的列举并不意味着其他实施方案没有用,并且不旨在将那些其他实施方案排除在本公开的范围之外。
如本申请中使用的词语“可以”是在允许的意义上使用的——即意味着有潜力——而不是在强制性意义上使用。
如本文中所用,室温为23℃±2℃。当在本文使用时,“环境条件”是指组合物所处于的或者涂层或所述涂层的基材所处于的环境的温度和压力。
如本文所用,术语“单官能”是指具有一个可聚合部分。如本文所用,术语“多官能”是指具有多于一个可聚合部分。
如本文所用,术语“当量equivalent(eq.)”如在化学符号中通常的那样,涉及反应中存在的反应性基团的相对数目。
如本文所用,术语“当量(equivalent weight)”是指分子量除以有关官能团的数目。因此,“环氧当量”(EEW)指含有一当量环氧基团的树脂的以克计的重量。
如本文所用,术语“环氧化物”表示特征在于存在至少一个环醚基团的化合物,即其中醚氧原子连接到两个相邻碳原子从而形成环状结构的化合物。该术语旨在包括单环氧化合物、聚环氧化合物(具有两个或多个环氧基团)和环氧化物封端的预聚物。术语“单环氧化合物”意在表示具有一个环氧基团的环氧化合物。术语“聚环氧化合物”意在表示具有至少两个环氧基团的环氧化合物。术语“二环氧化合物”意在表示具有两个环氧基团的环氧化合物。
环氧化物可以是未取代的,但也可以是惰性取代的。示例性惰性取代基包括氯、溴、氟和苯基。
如本文所用,“(甲基)丙烯酰基”是关于“丙烯酰基”和/或“甲基丙烯酰基”的简写术语。因此,术语“(甲基)丙烯酰胺”统指丙烯酰胺和甲基丙烯酰胺。
如本文中所用,“C1-Cn烷基”基团是指含有1至n个碳原子的一价基团,其是烷烃的基团并且包括直链和支链有机基团。照此,“C1-C30烷基”基团是指含有1至30个碳原子的一价基团,其是烷烃的基团并且包括直链和支链有机基团。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,此类烷基可以是未取代的或者可以被一个或多个取代基取代,例如卤素、硝基、氰基、酰胺基、氨基、磺酰基、亚磺酰基、硫烷基(sulfanyl)、硫酰氧基(sulfoxy)、脲、硫脲、胺磺酰基、磺酰胺和羟基。在适用的情况下,对给定取代基的偏好将在说明书中注明。然而,通常应注意优选含有1-18个碳原子的未取代烷基(C1-C18烷基),例如含有1-12个碳原子的未取代烷基(C1-C12烷基)或含有1-6个碳原子的未取代烷基(C1-C6烷基)。
如本文所用,术语“C1-C18羟烷基”是指具有1至18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并且烷基如上所定义。
“烷氧基”是指由–OA表示的一价基团,其中A是烷基:其非限制性实例是甲氧基、乙氧基和异丙氧基。如本文所用,术语“C1-C18烷基烷氧基”是指具有如上定义的烷氧基取代基的烷基,并且其中(烷基–O–烷基)部分总共包含1至18个碳原子:此类基团包括甲氧基甲基(–CH2OCH3)、2–甲氧基乙基(–CH2CH2OCH3)和2–乙氧基乙基。
如本文所用,术语“C2-C4亚烷基”定义为具有2至4个碳原子的饱和二价烃基。
术语“C3-C30环烷基”应理解为意指具有3至30个碳原子的任选取代的、饱和的、单环、双环或三环烃基。通常,应注意优选含有3-18个碳原子的环烷基(C3-C18环烷基)。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;以及降莰烷。
如本文中所用,如在“芳烷基”中一样,单独使用或作为较大部分的一部分使用的“C6-C18芳基”基团是指任选取代的单环、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环中的至少一个是芳族的。双环和三环体系包括苯并稠合的2-3元碳环。示例性芳基包括:苯基;(C1-C4)烷基苯基,例如甲苯基和乙基苯基;茚基;萘基、四氢萘基、四氢茚基;四氢蒽基;以及蒽基。并且可以注意优选苯基。
如本文所用,“烷基芳基”是指烷基取代的芳基,并且“取代的烷基芳基”是指进一步带有一个或多个上述取代基的烷基芳基。此外,如本文所用,“芳烷基”是指被如上定义的芳基取代的烷基。
如本文中所用,“C2-C20烯基”是指具有2至20个碳原子和至少一个烯属不饱和单元的烃基。烯基可以是直链、支链或环状的,并且可以任选地被取代。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(cis)”和“反式(trans)"构型,或者“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–3–烯基。
如本文中所用,术语“杂”是指含有一个或多个杂原子例如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”和“杂环烷基”部分分别是包含N、O、Si或S作为其结构的一部分的如上文所定义的烷基和环烷基。
如本文所用,术语“催化量”是指催化剂相对于反应物的亚化学计量的量,除非另有明确说明。
如本文所用,“伯氨基”是指与有机基团相连的NH2团,“仲氨基”是指与两个有机基团相连的NH基团,它们也可以一起成为环的一部分。因此,术语“叔胺”指的是氮原子不与氢原子结合的含氮部分。在使用时,术语“胺氢”是指伯氨基和仲氨基的氢原子。
如本文所用,术语“光引发剂”表示可以被携带能量的活化束,如电磁辐射,例如在用其辐照时活化的化合物。该术语旨在涵盖光致产酸剂和光致产碱剂。具体地,术语“光致产酸剂”是指在暴露于光化辐射时产生用于酸硬化树脂体系催化的酸的化合物或聚合物。术语“光致产碱剂”是指当暴露于合适的辐射时产生一种或多种碱的任何材料。
本文使用的术语“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组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。
本说明书中提及的分子量可以通过凝胶渗透色谱法(GPC)使用聚苯乙烯校准标准物进行测量,例如根据ASTM 3536所进行的。
如本文所用,“无水”是指有关组合物包含少于0.25重量%的水。例如,该组合物可含有少于0.1重量%的水或完全不含水。术语“基本上不含”应类似地解释为是指有关组合物含有少于0.25重量%的所述成分。
除非另有规定,否则本文所述的涂料组合物的粘度是使用Brookfield粘度计(型号RVT)在20℃和50%相对湿度(RH)的标准条件下测量的。粘度计使用已知粘度的硅油进行校准,其在5,000cps至50,000cps之间变化。一组连接到粘度计的RV转子用于校准。涂料组合物的测量通过使用6号转子以20转/分钟的速度进行1分钟直到粘度计平衡而进行。然后使用校准来计算对应于平衡读数的粘度。
具体实施方式
a)环氧化合物
基于组合物的重量,本发明的组合物通常应包含30至90重量%、优选40至80重量%的量的环氧树脂a)。例如,基于组合物的重量,本发明的组合物可包含40至60重量%的一种或多种所述环氧树脂a)。
在不旨在与本文给出的a)至d)部分的组成范围(重量%)相互排斥的本发明的组合物的替代表达中,优选的是组合物的总体特征在于0.05:1至0.95:1,例如0.25:1至0.85:1的环氧反应性基团与环氧基团的摩尔比。并且,为了完整起见,环氧反应性基团的总数包括组合物中存在的潜伏性反应基团。
硫醇基团应构成组合物中主要的环氧反应性反应官能团。上文提及的环氧反应性基团与环氧基团的摩尔比旨在确保尽可能有限量的未反应的巯基化合物存在于固化产物中:这种未反应的巯基化合物可能对该产物的性能有害。理想地,固化产物应基本上不含一种或多种未反应的巯基化合物。
如本文所用的环氧树脂可包括单官能环氧树脂、多官能或聚官能环氧树脂、以及它们的组合。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环氧基团的化合物的混合物。环氧树脂可以是饱和的或不饱和的、脂肪族的、脂环族的、芳族的或杂环的,并且可以是被取代的。此外,环氧树脂也可以是单体的或聚合的。
不意欲限制本发明,示例性单环氧化合物包括:环氧烷烃;环氧基取代的脂环族烃,例如环氧环己烷(cyclohexene oxide)、一氧化乙烯基环己烯、(+)-顺式-氧化柠檬烯、(+)-顺式,反式-氧化柠檬烯、(-)-顺式,反式-氧化柠檬烯、环氧环辛烷、环氧环十二烷和α–环氧蒎烷(α-pinene oxide);环氧基取代的芳族烃;一元醇或酚的单环氧基取代的烷基醚,例如脂肪族、脂环族和芳族醇的缩水甘油醚;一元羧酸的单环氧基取代的烷基酯,例如脂肪族、脂环族和芳族一元羧酸的缩水甘油酯;多元羧酸的单环氧基取代烷基酯,其中一个或多个其他羧基被烷醇进行酯化;环氧基取代的一元羧酸的烷基酯和烯基酯;多元醇的环氧烷基醚,其中一个或多个其他OH基团被羧酸或醇进行酯化或醚化;以及多元醇和环氧一元羧酸的单酯,其中一个或多个其他OH基团被羧酸或醇进行酯化或醚化。
举例来说,可以提及以下缩水甘油醚作为特别适合用于本文中的单环氧化合物: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;环己基缩水甘油醚;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。
在一个重要的实施方案中,单环氧化合物符合本文中的下式(I):
其中:Rw、Rx、Ry和Rz可以相同或不同并且独立地选自氢、卤素原子、C1-C8烷基、C3-C10环烷基、C2-C12烯基、C6-C18芳基或C7-C18芳烷基,前提条件是Ry和Rz中的至少一个不是氢。
优选的是,Rw、Rx和Ry是氢,并且Rz是苯基或C1-C8烷基,更优选C1-C4烷基。
考虑到这种实施方案,示例性单环氧化物包括:环氧乙烷;1,2–环氧丙烷(环氧丙烷);1,2–环氧丁烷;顺式–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。
在本发明中,提及使用至少一种选自以下的单环氧化合物:环氧乙烷;环氧丙烷;环氧环己烷;(+)-顺式-氧化柠檬烯、(+)-顺式,反式-氧化柠檬烯、(-)-顺式,反式-氧化柠檬烯、环氧环辛烷;以及环氧环十二烷。
同样,不意欲限制本发明,合适的聚环氧化合物可以是液体、固体或在溶剂中的溶液。此外,此类聚环氧化合物应具有100至700g/eq、例如120至320g/eq的环氧当量。并且通常,环氧当量小于500g/eq或甚至小于400g/eq的二环氧化合物是优选的:这主要是从成本的角度来看,因为在它们的生产中,较低分子量的环氧树脂需要更有限的纯化加工。
作为可在本发明中聚合的聚环氧化合物的类型或组的实例,可提及: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(polyethylenically unsaturated)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、脂肪族的或脂环族的,并且因此可以衍生自二元酚和二元醇。并且此类二缩水甘油醚的可用类别是:脂肪族和脂环族二醇的二缩水甘油醚,所述脂肪族和脂环族二醇例如有1,2–乙二醇、1,4–丁二醇、1,6–己二醇、1,8–辛二醇、1,12–十二烷二醇、环戊二醇和环己二醇;基于双酚A的二缩水甘油醚;双酚F二缩水甘油醚;基于聚亚烷基二醇的二缩水甘油醚,特别是聚丙二醇二缩水甘油醚;以及基于聚碳酸酯二醇的缩水甘油醚。
其他示例性聚环氧化合物包括但不限于:甘油聚缩水甘油醚;三羟甲基丙烷聚缩水甘油醚;季戊四醇聚缩水甘油醚;双甘油聚缩水甘油醚;聚甘油聚缩水甘油醚;以及山梨糖醇聚缩水甘油醚。
可用于本发明中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其他与环氧基团反应的基团的多元羧酸。多元羧酸可以是脂肪族的、脂环族的、芳族的和杂环的。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;偏苯三酸;均苯三酸;亚苯基二乙酸;氯菌酸;六氢邻苯二甲酸,特别是六氢邻苯二甲酸(1,2–环己烷二羧酸);联苯酸;萘二甲酸;二元酸和脂肪族多元醇的多酸封端的酯;(甲基)丙烯酸的聚合物和共聚物;以及巴豆酸。
也可提及的其他合适的二环氧化物包括:双不饱和脂肪酸C1-C18烷基酯的二环氧化物;丁二烯二环氧化物;聚丁二烯二缩水甘油醚;乙烯基环己烯二环氧化物;以及柠檬烯二环氧化物。
并且高度优选的聚环氧化合物的实例包括:双酚A环氧树脂,例如DERTM 331、DERTM332、DERTM 383、JERTM 828和Epotec YD 128;双酚F环氧树脂,例如DERTM 354;双酚A/F环氧树脂共混物,例如DERTM353;脂肪族缩水甘油醚,例如DERTM 736;聚丙二醇二缩水甘油醚,例如DERTM 732;固体双酚A环氧树脂,例如DERTM 661和DERTM 664UE;双酚A固体环氧树脂的溶液,例如DERTM671-X75;环氧线型酚醛树脂,例如DENTM 438;溴化环氧树脂,例如DERTM 542;蓖麻油三缩水甘油醚,例如ERISYSTM GE-35H;聚甘油–3–聚缩水甘油醚,例如ERISYSTM GE-38;以及,山梨糖醇缩水甘油醚,例如ERISYSTM GE-60;以及,可作为Lapox Arch-11获得的双(2,3–环氧丙基)环己烷–1,2–二羧酸酯。
虽然它不代表一个优选的实施方案,但本发明不排除进一步包含一种或多种选自以下的环状单体的可固化组合物:氧杂环丁烷;环状碳酸酯;环酐;以及,内酯。以下引文的公开内容可能有助于公开合适的环状碳酸酯官能化合物: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,基于环氧化合物的总重量,此类环状共聚单体应占少于20重量%,优选少于10重量%或少于5重量%。
b)含巯基化合物
基于组合物的重量,本发明的组合物包含1至50重量%、优选5至40重量%的b)至少一种具有至少两个对环氧化物有反应性的巯基的巯基化合物。例如,基于组合物的重量,本发明的组合物可以包含10至40重量%或20至40重量%的b)所述至少一种巯基化合物。
可以单独或组合使用的合适的含巯基化合物包括但不限于以下。
·液体硫醇封端的聚硫化物聚合物,其商业实例包括:聚合物(可获自Morton Thiokol),特别是其LP-3、LP-33、LP-980、LP-23、LP-55、LP-56、LP-12、LP-31、LP-32和LP-2类型;以及,/>聚合物(来自Akzo Nobel),特别是G10、G112、G131、G1、G12、G21、G22、G44和G4类型。
·硫醇封端的聚氧化烯醚,其可通过将聚氧化烯二和三醇与环氧氯丙烷或与环氧烷反应,然后与氢硫化钠反应而获得。
·聚氧化烯衍生物形式的硫醇封端的化合物,其以商品名(来自Cognis),特别是其WR-8、LOF和3-800类型已知。
·硫代羧酸的聚酯,其具体实例包括:季戊四醇四巯基乙酸酯(PETMP);三羟甲基丙烷三巯基乙酸酯(TMPMP);乙二醇二巯基乙酸酯;以及聚氧化烯二醇和三醇、乙氧基化三羟甲基丙烷和聚酯二醇与硫代羧酸如巯基乙酸和2–或3–巯基丙酸的酯化产物。
·2,4,6–三巯基–1,3,5–三嗪、2,2'–(亚乙二氧基)–二乙硫醇(三甘醇二硫醇)和/或乙二硫醇。
承认优先使用硫代羧酸的聚酯,特别地优先使用季戊四醇四巯基乙酸酯(PETMP)、三羟甲基丙烷三巯基乙酸酯(TMPMP)和乙二醇二巯基乙酸酯中的至少一种。
c)有机硼化合物
基于组合物的重量,本发明的组合物包含0.5至25重量%、优选1至20重量%的c)至少一种如下文定义的有机硼化合物。例如,基于组合物的重量,本发明的组合物可以包含5至20重量%或5至15重量%的c)所述至少一种有机硼化合物。
至少一种有机硼化合物选自叔胺的一价阳离子的四取代硼酸盐。其四取代硼酸根阴离子由通式(II)表示:
其中:R6、R7、R8和R9独立地选自C1-C6烷基、C6-C18芳基和C7-C24烷基芳基。
优选的是硼酸根部分中的R6、R7、R8和R9中的至少三个相同。更优选地,R6、R7、R8和R9都相同并且选自C1-C6烷基和苯基。并且应注意特别优选四苯基硼酸根阴离子。
虽然一价阳离子可以是四烷基铵离子,但优选的是阳离子是杂环部分,其可以是单环、双环或多环,其中带电荷的氮原子是杂脂族或杂芳族环体系的一部分。
可衍生一价阳离子的杂环叔胺的实例包括:吡啶类,例如皮考啉(甲基吡啶)、异喹啉、喹啉(1–苯并吡啶)、N,N–二甲基–4–氨基吡啶、联吡啶和2,6–二甲基吡啶;咪唑类;吡唑类,例如吡唑和1,4–二甲基吡唑;吗啉类,例如4–(2–羟乙基)吗啉、N–乙基吗啉、N–甲基吗啉和2,2'–二吗啉二乙醚;哌嗪类,例如1–(2–羟乙基)哌嗪和N,N–二甲基哌嗪;哌啶类,例如N–(2–羟乙基)哌啶、N–乙基哌啶、N–丙基哌啶、N–丁基哌啶、N–己基哌啶、N–环己基哌啶和N–辛基哌啶;吡咯烷类,例如N–丁基吡咯烷和N–辛基吡咯烷;以及环脒类。其他示例性杂环胺包括六亚甲基四胺、六亚乙基四胺和六丙基四胺。然而,可以提及对环脒鎓和咪唑鎓阳离子的优选。
在第一实施方案中,组合物的该部分的有机硼化合物由以下通式(III)表示:
其中:
R1、R2、R3、R4和R5独立地选自氢、C1-C18烷基、C6-C18芳基、C3-C18环烷基、C2-C20烯基、–C(O)Rq、–C(O)OH、–CN和–NO2;
Rq是C1-C6烷基;及
R6、R7、R8和R9独立地选自C1-C6烷基、C6-C18芳基和C7-C24烷基芳基。
优选地,R1、R2、R3、R4和R5独立地选自氢、C1-C12烷基、C6-C18芳基、C3-C12环烷基、C2-C6烯基、–CO2H、–CN和–NO2。作为对咪唑部分的优选陈述的替代或附加,硼酸根部分中的R6、R7、R8和R9中的至少三个相同。更优选地,R6、R7、R8和R9都相同并且选自C1-C6烷基和苯基。应注意特别优选四苯基硼酸根阴离子。
可以单独或混合使用的根据式(III)的示例性化合物包括但不限于:咪唑鎓四苯基硼酸盐;甲基咪唑鎓四苯基硼酸盐;2–乙基–4–甲基咪唑鎓四苯基硼酸盐;2–乙基–1,4–二甲基咪唑鎓四苯基硼酸盐;1–氰乙基–2–乙基–4–甲基咪唑鎓四苯基硼酸盐;1–氰乙基–2–十一烷基咪唑鎓四苯基硼酸盐;1–氰乙基–2–苯基咪唑鎓四苯基硼酸盐;1–乙烯基–2–甲基咪唑鎓四苯基硼酸盐;1–乙烯基–2,4–二甲基咪唑鎓四苯基硼酸盐;1–β–羟基–乙基–2–甲基–咪唑鎓四苯基硼酸盐;1–烯丙基–2–甲基咪唑鎓四苯基硼酸盐;1–烯丙基–2–苯基咪唑鎓四苯基硼酸盐;以及1–烯丙基–2–十一烷基咪唑鎓四苯基硼酸盐。可以注意到特别优选咪唑鎓四苯基硼酸盐、甲基咪唑鎓四苯基硼酸盐、2–乙基–4–甲基咪唑鎓四苯基硼酸盐和2–乙基–1,4–二甲基咪唑鎓四苯基硼酸盐。
尽管无意限制式(III)的化合物的合成方法,示例性制备程序包括以下物质的反应:
i)式(IV)的咪唑盐
其中R1-R5如上文所定义,并且Xn–是抗衡阴离子;与
ii)式(V)的四取代硼酸盐
其中R6-R9如上文所定义,并且M+是碱金属阳离子。
优选地,Xn–是氯离子、溴离子、碘离子、硫酸根、硝酸根或乙酸根阴离子。独立地或另外地,M+优选为Li+、Na+或K+。
上述反应通常可以在极性质子溶剂中进行,极性质子溶剂例如有:水、乙酸、甲醇、乙醇、正丙醇、以及正丁醇。此外,反应温度通常可以为10℃至100℃,例如20℃至80℃。
为了完整起见,式(IV)的咪唑盐可以通过以下物质的反应来制备:如下提供的咪唑,
与:选自以下的至少一种酸:无机酸,例如盐酸、硫酸和硝酸;有机酸,例如乙酸、草酸和琥珀酸;以及酸性芳族硝基化合物,例如苦味酸和苦铜酸;及
季铵化剂,例如烷基卤化物、芳基卤化物或芳基烷基卤化物。
根据该反应合成咪唑盐(IV)通常可以在极性质子溶剂中进行,极性质子溶剂例如有:水、乙酸、甲醇、乙醇、正丙醇、以及正丁醇。此外,反应温度通常可以为10℃至100℃,例如20℃至80℃。
在组合物的该部分的第二实施方案中,有机硼化合物由以下通式(VI)表示:
其中:
R10选自H、C1-C6烷基、C6-C18芳基、C7-C24芳烷基、C3-C18环烷基和C2-
C20烯基;
R6、R7、R8和R9独立地选自C1-C6烷基、C6-C18芳基和C7-C24烷基芳基;
及
n为1至3的整数,例如1或2。
优选地,R10选自H、C1-C6烷基、C3-C12环烷基、苯基、萘基或C7-C12芳烷基。更优选地,R10选自H、C1-C6烷基、C3-C12环烷基、苯基、萘基、苄基或甲苯基。作为对双环部分的优选陈述的替代或附加,硼酸根部分中的R6、R7、R8和R9中的至少三个相同。更优选地,R6、R7、R8和R9都相同并且选自C1-C6烷基和苯基。应注意特别优选四苯基硼酸根阴离子。
上述化合物的实例包括:8–苄基–1,8–二氮杂双环[5.4.0]十一碳–7–烯鎓四苯基硼酸盐、1,8–二氮杂双环[5.4.0]十一碳–7–烯四苯基硼酸盐、以及1,5–二氮杂双环[4.3.0]–壬–5–烯四苯基硼酸盐。
d)(甲基)丙烯酰胺单体
基于组合物的重量,本发明的组合物包含0.5至25重量%、优选1至20重量%的d)至少一种(甲基)丙烯酰胺单体。例如,基于组合物的重量,本发明的组合物可以包含5至20重量%或5至15重量%的d)所述至少一种(甲基)丙烯酰胺单体。
(甲基)丙烯酰胺单体是单官能的并且满足以下通式(VII):
其中:
Ra是H或Me;
G选自–NH2、–NHRb和–N(Rb)(Rc);
Rb和Rc独立地选自C1-C18烷基、C1-C18羟烷基、C1-C18烷基烷氧基、C6-
C18芳基和–(CH2)n–N(Rd)(Re);
n为1至4的整数;及
Rd和Re独立地选自H和C1-C6烷基。
在根据式(VII)的(甲基)丙烯酰胺单体的实施方案中:
Ra是H或Me;
G选自–NH2、–NHRb和–N(Rb)(Rc);
Rb和Rc独立地选自C1-C12烷基、C1-C12羟烷基、C1-C12烷基烷氧基和–(CH2)n–NRd Re;
n为2至4的整数;及
Rd和Re独立地选自C1-C4烷基。
根据式(VII)的合适的(甲基)丙烯酰胺单体的实例包括但不限于:(甲基)丙烯酰胺;N–甲基(甲基)丙烯酰胺;N,N–二甲基(甲基)丙烯酰胺;N–乙基(甲基)丙烯酰胺;N,N–二乙基(甲基)丙烯酰胺;N–异丙基(甲基)丙烯酰胺;N–正丁基(甲基)丙烯酰胺;N–叔丁基(甲基)丙烯酰胺;N,N–二正丁基(甲基)丙烯酰胺;N–辛基(甲基)丙烯酰胺;N–十二烷基(甲基)丙烯酰胺;N–十八烷基(甲基)丙烯酰胺;N–苯基(甲基)丙烯酰胺;N,N–二甲基氨基乙基(甲基)丙烯酰胺;N–(2–甲氧基乙基)(甲基)丙烯酰胺;N–(2–乙氧基乙基)(甲基)丙烯酰胺、N–(2–羟乙基)(甲基)丙烯酰胺;以及N–(2–羟丙基)(甲基)丙烯酰胺。
虽然它不代表一个优选的实施方案,但本发明不排除进一步包含一种或多种多官能(甲基)丙烯酰胺化合物的可固化组合物。然而,在可固化组合物中,基于d)所述单官能(甲基)丙烯酰胺单体的总重量,此类多官能(甲基)丙烯酰胺单体应占小于20重量%、优选小于10重量%或小于5重量%。
示例性多官能(甲基)丙烯酰胺化合物可由下式(VIII)表示:
其中:
R是H或Me;
L是–O–、C2-C4亚烷基或通过组合这些形成的二价连接基团。
后者提及的二价连接基团的实例包括但不限于:–OCH2CH2–、–OCH2CH2CH2–、–OCH2CH2CH2CH2–、–CH2OCH2–、–CH2OCH2CH2–和–CH2OCH2CH2CH2–。
e)添加剂和辅助成分
本发明中获得的所述组合物通常进一步包含可赋予这些组合物改进特性的佐剂和添加剂。例如,佐剂和添加剂可以赋予以下中的一种或多种:改善的弹性性质;改善的弹性回复;更长的允许处理时间;更快的固化时间;以及更低的残余粘性。此类佐剂和添加剂中包括的是催化剂、增塑剂、偶联剂、粘合促进剂、稳定剂包括紫外线稳定剂、抗氧化剂、增韧剂、填料、反应性稀释剂、干燥剂、杀菌剂、阻燃剂、流变佐剂、有色颜料或染料糊,和/或任选地还有少量的非反应性稀释剂。
合适的催化剂是促进环氧基团和环氧反应性基团之间的反应的物质,例如胺基和环氧基团之间的反应。具体的实例涉及使用胺催化剂,该胺催化剂通过将存在的反应性硫醇(–SH)基团去质子化成硫醇根(–S")而起作用,该硫醇根通过亲核开环聚合与环氧基团反应。
无意于限制在本发明中使用的催化剂,可提及以下合适的催化剂:i)酸或可水解为酸的化合物,特别是a)有机羧酸,例如乙酸、苯甲酸、水杨酸、2–硝基苯甲酸和乳酸;b)有机磺酸,例如甲磺酸、对甲苯磺酸和4–十二烷基苯磺酸;c)磺酸酯;d)无机酸,例如磷酸;e)路易斯酸化合物,例如BF3胺络合物、SbF6锍化合物、双芳烃铁络合物;f)布朗斯台德酸化合物,例如五氟锑酸络合物;以及e)上述酸和酸酯的混合物;ii)酚类,特别是双酚;iii)酚树脂;iv)曼尼希碱;以及v)亚磷酸酯,例如二苯基亚磷酸酯和三苯基亚磷酸酯。
在一个实施方案中,用于固化基于环氧树脂的组合物的胺催化剂可以是光致产碱剂:在暴露于紫外线辐射时,通常为320至420nm的波长,所述光致产碱剂释放胺,该胺催化环氧反应性基团加成到环氧化物。对光致产碱剂没有特别限制,只要它通过光辐照直接或间接产生胺即可。然而,可以提及的合适的光致产碱剂包括:氨基甲酸苄酯;安息香氨基甲酸酯;邻氨基甲酰基羟胺;O–氨基甲酰肟;芳族磺酰胺;α–内酰胺;N–(2–烯丙基乙烯基)酰胺;芳基叠氮化物、N–芳基甲酰胺和4–(邻硝基苯基)二氢吡啶。
为完整起见,光致产碱剂化合物的制备是本领域已知的,并且指导性参考文献包括美国专利号5,650,261(Winkel)。
在一个替代实施方案中,酸催化剂可以选自光致产酸剂(PAG):在用光能辐照时,离子型光致产酸剂进行解离反应并释放一个或多个路易斯酸或布朗斯台德酸分子,这些分子催化开环和侧接环氧基团的加成以形成交联。有用的光致产酸剂是热稳定的,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,例如在美国专利号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和美国专利号5,554,664中描述的那些。这些参考文献特别包括以脂肪族或芳族IVA和VIIA(CAS版本)族元素为中心的鎓盐,注意优选以I、S、P、Se-N和C为中心的鎓盐,例如选自氧化锍、碘鎓、锍、硒鎓、吡啶鎓、阳碳鎓和磷鎓的那些。
如本领域中已知的,离子型光致产酸剂(PAG)中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,其中例如常用亲核阴离子的反应性顺序是SbF6>AsF6>PF6>BF4。阴离子对反应性的影响归因于技术人员在本发明中应该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)正在增长的阳离子链中离子对分离的程度;(3)阴离子对氟化物提取和随后的链终止的敏感性。
不排除本发明的组合物包含替代上文提及的光致产碱剂和光致产酸剂化合物的光引发剂化合物,该一种或多种光引发剂化合物在用光化辐射辐照时会引发组合物的聚合或硬化。应注意,本发明的可光聚合组合物可以是可阳离子聚合的或可自由基聚合的:虽然环氧基团有阳离子活性,但该组合物包含具有自由基活性不饱和基团的化合物。鉴于此,优选的替代光引发剂将是经历Norrish I裂解以产生自由基的光活性化合物,该自由基可通过加成到丙烯酸双键中而引发。
总而言之,光引发剂应以基于100份反应物化合物为0.1至1.0重量份的量存在于可光聚合组合物中。
光引发剂以及本文在上面提及的光致产碱剂和光致产酸剂的使用可能会从光化学反应中产生残留化合物。可以通过常规分析技术检测残留物,例如:红外、紫外和NMR光谱;气相或液相色谱;以及质谱。因此,本发明可以包括固化的(环氧)基质共聚物和可检测量的来自光致产碱/酸剂的残留物。此类残留物少量存在,并且通常不干扰产品所需的物理化学特性。
无意限制本发明,包含一种或多种光引发剂的混合物可以用活化辐射照射以使一种或多种单体组分聚合。辐照的目的是由引发固化反应的光引发剂产生活性物质。一旦产生该物质,固化化学将遵循与任何化学反应相同的热力学规则:反应速率会因加热而加快。
技术人员将认识到,可以将光敏剂掺入组合物中以提高任何存在的光引发剂使用所传递能量的效率。基于光引发剂的重量,光敏剂通常以5至25重量%的量使用。
用于本发明目的的“增塑剂”是降低组合物粘度并因此促进其可加工性的物质。基于组合物的总重量,在本文增塑剂可以占至多10重量%或至多5重量%,并且优选地选自:聚二甲基硅氧烷(PDMS);二尿烷;单官能、直链或支链C4-C16醇的醚,例如Cetiol OE(可从Cognis Deutschland GmbH,Düsseldorf获得);松香酸酯、丁酸酯、硫丁酸酯、乙酸酯、丙酸酯和柠檬酸酯;基于硝基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;环氧化增塑剂;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;以及它们的混合物。注意,原则上,邻苯二甲酸酯可用作增塑剂,但由于它们的毒理学潜力,这些不是优选的。优选的是,增塑剂包含一种或多种聚二甲基硅氧烷(PDMS)或由其组成。
在某些实施方案中,该组合物包含基于该组合物的重量至多5重量%的至少一种环氧硅烷偶联剂,该偶联剂可用于增强固化组合物对给定表面的粘附。偶联剂的可水解基团可以与表面反应以去除不需要的羟基;其环氧基团与成膜聚合物反应以将所述聚合物与表面化学连接。优选地,偶联剂具有1至3个可水解官能团和至少一个环氧基团。
合适的环氧硅烷偶联剂的实例包括但不限于:缩水甘油氧基聚亚甲基三烷氧基硅烷,例如3–缩水甘油氧基–1–丙基–三甲氧基硅烷;(甲基)丙烯酰氧基聚亚甲基三甲氧基硅烷,例如3–甲基丙烯酰氧基–1–丙基三甲氧基硅烷;γ–甲基丙烯酰氧基丙基三甲氧基硅烷(A-174,可获自GE Silicones);γ–缩水甘油氧基丙基三甲氧基硅烷(A-187,可获自Momentive Performance Materials,Inc.);α–缩水甘油氧基丙基甲基二乙氧基硅烷(A-2287,可获自Momentive Performance Materials,Inc.);乙烯基–三(2–甲氧基乙氧基)硅烷(A-172,可获自Momentive Performance Materials,Inc.);以及,α–氯丙基三甲氧基硅烷(KBM-703,可获自Shin-Etsu Chemical Co.,Ltd.)。
用于本发明目的的“稳定剂”应理解为抗氧化剂、紫外线稳定剂或水解稳定剂。在本文中,基于组合物的总重量,稳定剂可以占总共至多10重量%或至多5重量%。适用于本文的稳定剂的标准商业实例包括: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)型胺类;磷;硫;以及它们的混合物。
如所指出的,根据本发明的组合物可以另外包含填料。此处合适的是例如白垩、石灰粉、沉淀和/或热解硅酸、沸石、膨润土、碳酸镁、硅藻土、氧化铝、粘土、滑石、氧化钛、氧化铁、氧化锌、沙子、石英、燧石、云母、玻璃粉和其他磨碎的矿物质。也可以使用有机填料,特别是炭黑、石墨、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、磨碎的胡桃壳和其他短切纤维。也可以加入短纤维,例如玻璃纤维、玻璃丝、聚丙烯腈、碳纤维、Kevlar纤维或聚乙烯纤维。铝粉同样适合作为填料。
热解和/或沉淀硅酸有利地具有10至90m2/g的BET表面积。当使用它们时,它们不会引起根据本发明的组合物的粘度的任何额外增加,但确实有助于增强固化的组合物。
同样可以想到使用具有较高BET表面积,有利地为100至250m2/g、特别是110至170m2/g的热解和/或沉淀硅酸作为填料:因为较大的BET表面积,用较小重量比例的硅酸实现了增强固化组合物的效果。
也适合作为填料的是具有矿物壳或塑料壳的中空球。例如,这些可以是中空玻璃球,其可以商品名Glass商购获得。可以使用基于塑料的中空球,例如或/>并且其描述于EP 0 520 426B1中:它们由无机或有机物质组成,并且各自具有1mm或更小、优选500μm或更小的直径。
赋予组合物触变性的填料对于许多应用可能是优选的:此类填料也被描述为流变佐剂,例如氢化蓖麻油、脂肪酸酰胺或可膨胀塑料例如PVC。
基于组合物的总重量,存在于本发明组合物中的填料的总量优选为0至60重量%,更优选0至30重量%。可固化组合物的所需粘度通常由添加的填料总量决定,并且认为为了易于从合适的分配设备例如管中可挤出,可固化组合物应具有3000至150,000mPas、优选40,000至80,000mPas、或甚至50,000至60,000mPas的粘度。
合适的颜料的实例是二氧化钛、氧化铁或炭黑。
为了甚至进一步提高保存期限,通常建议通过使用干燥剂使本发明的组合物相对于水分渗透进一步稳定。有时还需要通过使用一种或多种反应性稀释剂来降低用于特定应用的根据本发明的粘合剂或密封剂组合物的粘度。基于组合物的总重量,存在的反应性稀释剂的总量通常为至多15重量%,优选为1至5重量%。
在可以有效地调节其粘度的情况下,也不排除本发明组合物中非反应性稀释剂的存在。例如,但仅用于说明,组合物可包含以下一种或多种: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;丙二醇苯基醚;二丙二醇;二丙二醇单甲醚;二丙二醇二甲醚;二丙二醇二正丁醚;N–甲基吡咯烷酮;二苯甲烷;二异丙基萘;石油馏分,例如产品(可从Exxon获得);烷基苯酚,例如叔丁基苯酚、壬基苯酚、十二烷苯酚和8,11,14–十五碳三烯基苯酚;苯乙烯化苯酚;双酚;芳烃树脂,尤其是含有酚基的那些,例如乙氧基化或丙氧基化酚类;己二酸酯;癸二酸酯;邻苯二甲酸酯;苯甲酸酯;有机磷酸酯或磺酸酯;以及磺酰胺。
除上述之外,优选的是,基于组合物的总重量,所述非反应性稀释剂占小于10重量%,特别是小于5重量%或小于2重量%。
单组分(1K)组合物的示例性实施方案
在本发明的一个示例性实施方案中,单组分(1K)组合物包含,基于组合物的重量:
40至60重量%的a)至少一种环氧树脂;
10至40重量%的b)至少一种具有至少两个对环氧化物有反应性的巯基的巯基化合物;
5至20重量%的c)至少一种选自环脒鎓四取代硼酸盐和咪唑鎓四取代硼酸盐的有机硼化合物;及
5至20重量%的d)至少一种式(VII)的(甲基)丙烯酰胺单体:
其中:
Ra是H或Me;
G选自–NH2、–NHRb和–N(Rb)(Rc);
Rb和Rc独立地选自C1-C12烷基、C1-C12羟烷基、C1-C12烷基烷氧基和–
(CH2)n–NRd Re;
n为2至4的整数;及
Rd和Re独立地选自C1-C4烷基。
其中所述组合物的特征在于环氧反应性基团与环氧基团的摩尔比为0.05:1至0.95:1。
方法和应用
为了形成组合物,将上述部分放在一起并混合。如本领域已知的,为了形成单组分(1K)可固化组合物,将组合物的元素放在一起并在抑制或防止反应性组分反应的条件下均匀混合:如本领域技术人员容易理解的,这可能包括限制或防止暴露于湿气、热或辐照或限制或防止成分潜伏性催化剂活化的混合条件。因此,通常优选的是不要手动混合固化成分,而是通过机器例如静态或动态混合器在无水条件下以预定量混合,无需有意加热或光辐照。
根据本发明最广泛的方法方面,将上述组合物施用到基材上,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从那里去除异物:如果适用,该步骤可以促进组合物随后粘附到其上。此类处理在本领域中是已知的并且可以以由例如使用以下处理中的一种或多种构成单阶段或多阶段方式进行:用适用于基材的酸和任选的氧化剂的蚀刻处理;超声处理;等离子处理,包括化学等离子处理、电晕处理、大气等离子处理和火焰等离子处理;浸入水性碱性脱脂浴中;用水性清洁乳液处理;用清洁溶剂处理,例如四氯化碳或三氯乙烯;以及水冲洗,优选用去离子水或软化水冲洗。在使用水性碱性脱脂浴的那些情况下,任何残留在表面上的脱脂剂都应通过用去离子水或软化水冲洗基材表面而去除。
在一些实施方案中,本发明的涂料组合物对优选预处理的基材的粘附可以通过向其施用底漆来促进。虽然技术人员能够选择合适的底漆,但选择底漆的指导性参考文献包括但不限于:美国专利号3,671,483;美国专利号4,681,636;美国专利号4,749,741;美国专利号4,147,685;以及美国专利号6,231,990。
然后将组合物通过常规的施用方法施用到基材的预处理的、任选涂底漆的表面,所述常规的施用方法例如有:刷涂;辊涂,例如使用其中组合物不含溶剂的4施料辊设备或用于含溶剂的组合物的2施料辊设备进行的辊涂;刮刀法施用;印刷方法;以及喷涂方法,包括但不限于空气雾化喷涂、空气辅助喷涂、无气喷涂和大容量低压喷涂。对于涂料和粘合剂应用,建议将组合物施用到10至500μm的湿膜厚度。在此范围内应用较薄的层更经济,并且提供减少厚固化区域的可能性,对于涂层应用而言,该厚固化区域可能需要打磨。然而,在施用更薄的涂层或层时必须进行严格的控制,以避免形成不连续的固化膜。
本发明组合物的固化可以在50℃至200℃、优选50℃至150℃、特别是70℃至120℃的温度范围内发生。合适的温度取决于存在的具体化合物和所需的固化速率,并且可以由技术人员在个案中确定,必要时使用简单的初步测试。然而,在适用的情况下,由组合物的各个组分形成的混合物的温度可以使用包括微波感应在内的常规手段升高到混合温度和/或施加温度以上。
为完整起见,应注意本发明不排除以“膜粘合剂”形式制备环氧粘合剂。将环氧树脂、硬化剂和其他所需组分的预聚物混合物作为涂层施加到聚合物膜基材上,卷起并储存在足够低的温度下,以抑制组分之间的化学反应。需要时,将膜粘合剂从低温环境中取出并施涂在金属或复合材料部件上,剥离背衬,组装完成并在烘箱或高压釜中固化。
根据本发明的可固化组合物尤其可用于:清漆;油墨;用于纤维和/或颗粒的粘合剂;玻璃的涂覆;矿建材料如石灰和/或水泥粘结的灰泥、含石膏的表面、纤维水泥建筑材料和混凝土的涂覆和粘合;木材和木质材料例如刨花板、纤维板和纸的涂覆、密封和粘合;金属表面的涂覆和粘合;含沥青和柏油的路面的涂覆;各种塑料表面的涂覆、密封或粘合;以及皮革和纺织品的涂覆。
在一个特别优选的实施方案中,将本发明的组合物施用于结构基材以产生粘附的、高度耐磨的涂层或粘合。粘合操作通常可以在低于200℃、低于150℃、甚至低于120℃的温度下进行,因此该组合物可用于热敏基材上。固化后可获得有效的耐磨性。此外,当粘合到机械结构的表面或者地板或路面时,涂料组合物可以提供牢固可靠的粘合,提供热稳定性,并且为表面提供防腐蚀保护,并可防止表面与对特定结构的操作或效率有害的化合物接触。
以下实施例是对本发明的说明,并不以任何方式限制本发明的范围。
实施例
实施例中使用了以下化合物和材料:
JERTM 828:通过双酚A和环氧氯丙烷的缩聚形成的双酚A型液体环氧树脂,可获自Mitsubishi Chemical。
季戊四醇四(3–巯基丙酸酯):可获自Sigma Aldrich(CAS号7575-23-7)
DBU硼酸盐:8–苄基–1,8–二氮杂双环[5.4.0]十一碳–7–烯鎓四苯基硼酸盐,可获自San-Apro Ltd.(CAS号114367-12-3)
2–乙基–4–甲基咪唑鎓四苯基硼酸盐:Fuji Film Wako Chemical(CAS号53831-70-2)
N,N–二甲基丙烯酰胺:可获自Sigma Aldrich(CAS号2680-03-7)
下表1中描述的配制物是在混合下形成的。配制物是透明液体,实施例1是无色的,实施例2是琥珀色的。当在室温下储存7天时,两种配制物均未显示粘度显著增加。
表1
实施例1的组合物:i)在120℃下加热45分钟内固化;ii)在150℃下加热10分钟内固化。获得的固化产物是透明的琥珀色固体。
实施例2的组合物:i)在90℃下加热100分钟内固化;ii)在100℃下加热40分钟内固化;以及,iii)在120℃下加热15分钟内固化。获得的固化产物是透明的琥珀色固体。
鉴于前述描述和实施例,本领域技术人员将明白在不脱离权利要求的范围的情况下可以对其进行等效修改。
Claims (17)
1.单组分(1K)组合物,基于所述组合物的重量,其包含:
30至90重量%的a)至少一种环氧树脂;
1至50重量%的b)至少一种具有至少两个对环氧化物有反应性的巯基的巯基化合物;
0.5至25重量%的c)至少一种选自叔胺的一价阳离子的四取代硼酸盐的有机硼化合物;及
0.5至25重量%的d)至少一种式(VII)的(甲基)丙烯酰胺单体:
其中:
Ra是H或Me;
G选自–NH2、–NHRb和–N(Rb)(Rc);
Rb和Rc独立地选自C1-C18烷基、C1-C18羟烷基、C1-C18烷基烷氧基、C6-C18芳基和–(CH2)n–N(Rd)(Re);
n为1至4的整数;及
Rd和Re独立地选自H和C1-C6烷基。
2.根据权利要求1所述的组合物,基于所述组合物的重量,其包含:
40至80重量%的a)至少一种环氧树脂;
5至40重量%的b)至少一种具有至少两个对环氧化物有反应性的巯基的巯基化合物;
1至20重量%的c)至少一种选自叔胺的一价阳离子的四取代硼酸盐的有机硼化合物;及
1至20重量%的d)所述至少一种(甲基)丙烯酰胺单体。
3.根据权利要求1或2所述的组合物,其中环氧反应性基团与环氧基团的摩尔比为0.05:1至0.95:1。
4.根据权利要求1至3之一所述的组合物,其含有a)至少一种选自以下的环氧树脂: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。
5.根据权利要求1至4之一所述的组合物,其中b)部分包含硫代羧酸的至少一种聚酯。
6.根据权利要求5所述的组合物,其中b)部分包含至少一种选自以下的巯基化合物:季戊四醇四巯基乙酸酯(PETMP)、三羟甲基丙烷三巯基乙酸酯(TMPMP)、以及乙二醇二巯基乙酸酯。
7.根据权利要求1至6之一所述的组合物,其中c)部分包含环脒鎓四取代硼酸盐和/或咪唑鎓四取代硼酸盐。
8.根据权利要求7所述的组合物,其中c)部分包含由以下通式(III)表示的化合物:
其中:
R1、R2、R3、R4和R5独立地选自氢、C1-C18烷基、C6-C18芳基、C3-C18环烷基、C2-C20烯基、–C(O)Rq、–C(O)OH、–CN和–NO2;
Rq是C1-C6烷基;及
R6、R7、R8和R9独立地选自C1-C6烷基、C6-C18芳基和C7-C24烷基芳基。
9.根据权利要求8所述的组合物,其中R1、R2、R3、R4和R5独立地选自氢、C1-C12烷基、C6-C18芳基、C3-C12环烷基、C2-C6烯基、–CO2H、–CN和–NO2。
10.根据权利要求7所述的组合物,其中c)部分包含由以下通式(VI)表示的化合物:
其中:
R10选自H、C1-C6烷基、C6-C18芳基、C7-C24芳烷基、C3-C18环烷基和C2-C20烯基;
R6、R7、R8和R9独立地选自C1-C6烷基、C6-C18芳基和C7-C24烷基芳基;及
n为1至3的整数。
11.根据权利要求10所述的组合物,其中R10选自H、C1-C6烷基、C3-C12环烷基、苯基、萘基、苄基或甲苯基。
12.根据权利要求8或10所述的组合物,其中R6、R7、R8和R9都相同并且选自C1-C6烷基和苯基。
13.根据权利要求7所述的组合物,其中c)部分包含至少一种选自以下的盐:咪唑鎓四苯基硼酸盐、甲基咪唑鎓四苯基硼酸盐、2–乙基–4–甲基咪唑鎓四苯基硼酸盐和2–乙基–1,4–二甲基咪唑鎓四苯基硼酸盐、8–苄基–1,8–二氮杂双环[5.4.0]十一碳–7–烯鎓四苯基硼酸盐、1,8–二氮杂双环[5.4.0]十一碳–7–烯四苯基硼酸盐、以及1,5–二氮杂双环[4.3.0]–壬–5–烯四苯基硼酸盐。
14.根据权利要求1至13之一所述的组合物,其中d)部分包含至少一种式(VII)的(甲基)丙烯酰胺单体:
其中:
Ra是H或Me;
G选自–NH2、–NHRb和–N(Rb)(Rc);
Rb和Rc独立地选自C1-C12烷基、C1-C12羟烷基、C1-C12烷基烷氧基和–(CH2)n–NRd Re;
n为2至4的整数;及
Rd和Re独立地选自C1-C4烷基。
15.根据权利要求1至14之一所述的组合物,其中d)部分包含至少一种选自以下的(甲基)丙烯酰胺单体:(甲基)丙烯酰胺;N–甲基(甲基)丙烯酰胺;N,N–二甲基(甲基)丙烯酰胺;N–乙基(甲基)丙烯酰胺;N,N–二乙基(甲基)丙烯酰胺;N–异丙基(甲基)丙烯酰胺;N–正丁基(甲基)丙烯酰胺;N–叔丁基(甲基)丙烯酰胺;N,N–二正丁基(甲基)丙烯酰胺;N–辛基(甲基)丙烯酰胺;N–十二烷基(甲基)丙烯酰胺;N–十八烷基(甲基)丙烯酰胺;N–苯基(甲基)丙烯酰胺;N,N–二甲基氨基乙基(甲基)丙烯酰胺;N–(2–甲氧基乙基)(甲基)丙烯酰胺;N–(2–乙氧基乙基)(甲基)丙烯酰胺;N–(2–羟乙基)(甲基)丙烯酰胺;以及N–(2–羟丙基)(甲基)丙烯酰胺。
16.由根据权利要求1至15之一所述的单组分(1K)组合物获得的固化产物。
17.根据权利要求16所述的固化产物作为涂料、密封剂或粘合剂的用途。
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EP19213407.0A EP3831862B1 (en) | 2019-12-04 | 2019-12-04 | One component (1k) composition based on epoxy resin |
EP19213407.0 | 2019-12-04 | ||
PCT/EP2020/084034 WO2021110634A1 (en) | 2019-12-04 | 2020-12-01 | One component (1k) composition based on epoxy resin |
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