CN108699219B - 用于固化环氧树脂组合物的共混物 - Google Patents
用于固化环氧树脂组合物的共混物 Download PDFInfo
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- CN108699219B CN108699219B CN201780012881.0A CN201780012881A CN108699219B CN 108699219 B CN108699219 B CN 108699219B CN 201780012881 A CN201780012881 A CN 201780012881A CN 108699219 B CN108699219 B CN 108699219B
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Abstract
本发明提供可固化组合物,其包含环氧树脂和包含至少两种胺的共混物的固化组分。所述可固化组合物可以与增强纤维组合,和可以固化形成可用于多种用途如风力涡轮机叶片的复合制品。
Description
技术领域
本发明大体涉及包含环氧树脂和固化组分的可固化组合物,所述固化组分包含聚醚胺、选自咪唑和/或叔胺的促进剂和任选的第二胺,和本发明涉及应用所述可固化组合物生产纤维增强复合制品,包括但不限于风力涡轮机叶片。
背景技术
为了将环氧树脂转化为有用的产品,它们必须应用固化剂通过化学反应“固化”或交联为三维难熔网络。固化剂通过与环氧树脂中的环氧化物基团或羟基基团反应或引起反应而起作用。通常,这通过两种可能路径进行:i)环氧化物基团自身反应(均聚);或ii)环氧基和/或羟基官能团与反应性中间体或固化剂反应。
在环氧树脂结构应用中通常采用三类主要的化学固化剂,包括胺、酸酐和路易斯酸。胺可以进一步分为脂族、环脂族和芳族胺。所有胺以及酸酐通过亲核加成至环氧化物终端碳原子上而与环氧环反应,分别得到对应的β-羟胺或β-羟酯。路易斯酸通过环氧化物的均聚固化环氧树脂。
因为脂族胺比环脂族和芳族胺更具亲核性,在室温下它们更快地与环氧树脂反应。因此,它们提供相对短的加工寿命(液态环氧树脂约30分钟)。环脂族胺比直链脂族胺更受阻,反应更慢和因此固化需要温和加热。最后,芳族胺在室温下反应迟缓导致较长的加工寿命,和因此在高温下固化时应用。
相比之下,酸酐提供更长的加工寿命,但它们需要仔细贮存,从而防止由于水分吸收而降解。它们也需要应用热量和少量促进剂从而引发完全固化。
最后,当少量添加时,路易斯酸和特别是三氟化硼用作阳离子均聚环氧基分子为聚醚的催化剂。但由于三氟化硼造成环氧树脂非常迅速和强放热聚合,当不是很少量树脂发生固化时,必须使用阻聚技术停止室温反应。
改进环氧树脂固化领域的大多数工作均包括应用一种或多种胺作为固化剂,例如:
US 7,816,581描述了应用至少两种聚醚胺来固化环氧树脂;
US 8,741,426描述了聚醚胺、具有至少2个官能团的第二胺和胍衍生物的共混物及其在固化环氧树脂中的用途;
美国专利申请公开No.2011/0319564公开了通式R1R2R3N的胺(其中R1和R2独立地为脂族或脂环族有机官能基团和R3为具有2-18个碳原子骨架的烷基)和聚醚胺的混合物,和这种混合物固化环氧树脂的用途;
美国专利申请公开No.2012/0328811公开了含大量环脂族胺和少量聚醚胺的第一固化组分和含咪唑的第二固化组分的用途;和
美国专利申请公开No.2013/0225788描述了含至少一种脂族或环脂族胺、芳族胺和咪唑的固化剂混合物,和该固化剂混合物能够在等于或低于120℃下固化环氧树脂。
尽管存在现有技术的胺固化剂,但仍需要开发新的多用途固化剂,当其与环氧树脂混合形成可固化组合物时,不会造成可固化组合物的粘度猛增以至于无法保持足够的流动性,也不会负面影响循环时间(处理和固化)。
发明内容
本发明提供可固化组合物,包含:(i)环氧树脂;和(ii)包含聚醚胺、选自咪唑、叔胺和它们的组合的促进剂和任选的第二胺的固化组分。
在一个方面,所述可固化组合物基本不含环状碳酸酯、胍及其衍生物和芳族胺。
在另一个方面,提供通过混合所述环氧树脂和固化组分制备可固化组合物的方法。
在又一个方面,提供生产复合制品的方法,包括如下步骤:(i)提供增强纤维的层或束;(ii)提供可固化组合物;(iii)使所述增强纤维与可固化组合物接触以涂覆和/或浸渍增强纤维;和(iv)在至少约60℃的温度下固化所涂覆和/或浸渍的增强纤维。
附图说明
图1描述了实施例1a-1f的配制物的固化曲线。
图2描述了实施例2a-2e的配制物的固化曲线。
图3描述了实施例3a-3f的配制物的固化曲线。
图4描述了实施例8-11的配制物的玻璃转化温度。
具体实施方式
本发明大体提供可固化组合物,包含:(i)环氧树脂;和(ii)包含聚醚胺、选自咪唑、叔胺和它们的组合的促进剂和任选的第二胺的固化组分。在一个实施方案中,固化组分基本不含环状碳酸酯、胍及其衍生物和芳族胺。
在一个特定的实施方案中,本发明涉及可固化组合物,包含:(i)环氧树脂;和(ii)包含聚醚胺、叔胺和任选的第二胺的固化组分,其中所述叔胺选自N-乙基吗啉、异丙基吗啉、N-丁基吗啉、甲氧基乙基吗啉、羟基乙基吗啉、2,2′-二吗啉代二乙基醚、N,N′-二吗啉代乙烷、甲基二乙醇胺、N,N-二甲基环己胺、甲基二环己胺、N,N,N'-三甲基-N'-(2-羟基乙基)二(2-氨基乙基)醚、二-(2-二甲基氨基乙基)醚、N,N′-二甲基哌嗪、1,3,5-三(3-(二甲基氨基)丙基)-六氢-s-三嗪、2,4,6-三(二甲基氨基甲基)酚和它们的组合。
在另一个实施方案中,本发明涉及可固化组合物,包含:(i)环氧树脂;和(ii)包含两种或更多种聚醚胺、叔胺和任选的第二胺的固化组分,其中所述叔胺选自N-乙基吗啉、异丙基吗啉、N-丁基吗啉、甲氧基乙基吗啉、羟基乙基吗啉、2,2′-二吗啉代二乙基醚、N,N′-二吗啉代乙烷、甲基二乙醇胺、N,N-二甲基环己胺、甲基二环己胺、N,N,N'-三甲基-N'-(2-羟基乙基)二(2-氨基乙基)醚、二-(2-二甲基氨基乙基)醚、N,N′-二甲基哌嗪、1,3,5-三(3-(二甲基氨基)丙基)-六氢-s-三嗪、2,4,6-三(二甲基氨基甲基)酚和它们的组合。
在另一个实施方案中,本发明涉及可固化组合物,包含:(i)环氧树脂;和(ii)聚醚胺、叔胺和任选的第二胺的固化组分,其中所述叔胺选自N-乙基吗啉、异丙基吗啉、N-丁基吗啉、甲氧基乙基吗啉、羟基乙基吗啉、2,2′-二吗啉代二乙基醚、N,N′-二吗啉代乙烷、甲基二乙醇胺、N,N,N'-三甲基-N'-(2-羟基乙基)二(2-氨基乙基)醚、二-(2-二甲基氨基乙基)醚、N,N′-二甲基哌嗪、1,3,5-三(3-(二甲基氨基)丙基)-六氢-s-三嗪和它们的组合,其中所述固化组分基本不含环状碳酸酯、胍及其衍生物和芳族胺。所述固化组分还可以包含咪唑。
已经令人惊奇地发现本发明的固化组分不仅具有能够延长可固化组合物加工寿命的能力,而且能够迅速固化环氧树脂提供热和机械性能良好平衡的固化制品。因为可固化组合物保持对于复合物制品加工来说通常需要的较低粘度和较长加工寿命,这特别适用于通过细丝绕制、树脂灌注、手工涂覆、真空辅助的树脂传递过程、拉挤和预浸料制备复合制品。具体的复合制品可以包括但不限于管道、管件、贮罐、高压容器、风力涡轮机叶片、船只和复合工具。
如下术语具有如下意义。
正如这里所应用,术语“固化”指通过化学交联硬化环氧树脂。术语“可固化”意味着组合物能够承受使组合物固化的条件或热固化状态或条件。
术语“芳族胺”指含芳基部分的伯、仲或叔胺,而术语"芳基"指具有6-14个碳原子的取代或未取代芳族碳环基团。
术语“环状碳酸酯”指具有碳酸基(CO3)作为环状化合物一部分的环状化合物。
术语“胍及其衍生物”指胍化合物及胍化合物的衍生物,其中至少一个氨基氢被C1-C20烷基取代。
当用于指配制物中基本不存在某物质时,术语“基本不含”指不存在这种物质,或如果存在,则作为偶然的杂质或副产品存在。换句话说,所述物质不影响配制物的性质。
术语“加工寿命”指催化的可固化组合物保持粘度足够低从而可用于处理的加工时间或时间长度。
术语"包含"及其衍生说法不打算排除任何附加组分、步骤或程序的存在,不管其是否在这里公开。为了避免任何怀疑,如果无相反指出,通过应用术语"包含",这里要求开的所有组合物均可以包括任何附加的添加剂或化合物。与之相比,如果在这里出现,术语"主要由…组成"排除了随后描述的任何其它组分、步骤或程序的范围,除了那些对可操作性不关键的以外,和如果应用,术语"由…组成"不包含没有具体描述或列出的任何组分、步骤或程序。如果不另外指出,术语"或"指单独列出的各项及其任何组合。
正如这里所应用,术语“胺/环氧化学计量比”指含胺化合物的胺氢键(即-NH键)数与环氧树脂的环氧基数之间的比。例如,胺/环氧化学计量比为1:1指胺和环氧树脂具有相同数量的胺氢键和环氧基团。
不定冠词“a”和“an”在这里指一种或多种(即至少一种)的语法主体。作为示例,“环氧树脂”指一种或多种环氧树脂。
语句“在一个方面”、“按照一个方面”、“在一个实施方案中”、“按照一个实施方案”和类似说法通常指所述语句之后的具体特征、结构或特性包含在本发明的至少一个方面或实施方案中,和可以包含在本发明的多个方面和实施方案中。重要地,这种语句不必指相同的方面或实施方案。
如果说明书称某种组分或特征“可以”、“能够”、“可能”或"可"被包括或具有某种特征,则所述特定组分或特征不是必须被包括或一定具有所述特征。
可固化组合物
本发明大体提供一种可固化组合物,包含:(i)环氧树脂;和(ii)包含聚醚胺、选自咪唑、叔胺和它们的组合的促进剂和任选的第二胺的固化组分。在一个实施方案中,所述可固化组合物基本不含环状碳酸酯、胍及其衍生物和芳族胺。
在一个实施方案中,所述促进剂为咪唑。可固化组合物的一个这种实施方案包含:(i)环氧树脂;和(ii)包含如下的固化组分:(a)以100重量份固化组分计大于20重量份的聚醚胺,(b)以100重量份固化组分计大于1重量份的咪唑,和任选的(c)第二胺,其中所述可固化组合物基本不含环状碳酸酯、胍及其衍生物和芳族胺。
在另一个实施方案中,促进剂为叔胺。叔胺可以选自N-乙基吗啉、异丙基吗啉、N-丁基吗啉、甲氧基乙基吗啉、羟基乙基吗啉、2,2′-二吗啉代二乙基醚、N,N′-二吗啉代乙烷、甲基二乙醇胺、N,N-二甲基环己胺、甲基二环己胺、N,N,N'-三甲基-N'-(2-羟基乙基)二(2-氨基乙基)醚、二-(2-二甲基氨基乙基)醚、N,N′-二甲基哌嗪、1,3,5-三(3-(二甲基氨基)丙基)-六氢-s-三嗪、2,4,6-三(二甲基氨基甲基)酚和它们的组合。
在另一个实施方案中,促进剂为咪唑和选自如下的叔胺:N-乙基吗啉、异丙基吗啉、N-丁基吗啉、甲氧基乙基吗啉、羟基乙基吗啉、2,2′-二吗啉代二乙基醚、N,N′-二吗啉代乙烷、甲基二乙醇胺、N,N-二甲基环己胺、甲基二环己胺、N,N,N'-三甲基-N'-(2-羟基乙基)二(2-氨基乙基)醚、二-(2-二甲基氨基乙基)醚、N,N′-二甲基哌嗪、1,3,5-三(3-(二甲基氨基)丙基)-六氢-s-三嗪、2,4,6-三(二甲基氨基甲基)酚和它们的组合。
在又一个实施方案中,促进剂为选自如下的叔胺:N-乙基吗啉、异丙基吗啉、N-丁基吗啉、甲氧基乙基吗啉、羟基乙基吗啉、2,2′-二吗啉代二乙基醚、N,N′-二吗啉代乙烷、甲基二乙醇胺、N,N,N'-三甲基-N'-(2-羟基乙基)二(2-氨基乙基)醚、二-(2-二甲基氨基乙基)醚、N,N′-二甲基哌嗪、1,3,5-三(3-(二甲基氨基)丙基)-六氢-s-三嗪和它们的组合,和所述固化组分基本不含环状碳酸酯、胍及其衍生物和芳族胺。
按照一个方面,可固化组合物包含环氧树脂。通常,任何含环氧基的化合物均适合在本发明中用作环氧树脂,如在US 5,476,748中公开的含环氧基的化合物,所述专利在这里作为参考引入。环氧树脂可以为固体或液体。在一个实施方案中,所述环氧树脂选自如下物质:聚缩水甘油基环氧化合物;非缩水甘油基环氧化合物;环氧甲酚酚醛清漆化合物;环氧苯酚酚醛清漆化合物;和它们的混合物。
聚缩水甘油基环氧化合物可以为聚缩水甘油醚、聚(β-甲基缩水甘油基)醚、聚缩水甘油酯或聚(β-甲基缩水基油基)酯。聚缩水甘油醚、聚(β-甲基缩水甘油基)醚、聚缩水甘油酯和聚(β-甲基缩水甘油基)酯的合成和例子在US 5,972,563中进行了公开,其在这里作为参考引入。例如醚可以通过使具有至少一个自由醇羟基和/或酚羟基的化合物与合适取代的表氯醇在碱性条件反应或在酸性催化剂的存在下反应随后用碱处理而获得。所述醇例如可以为无环醇如乙二醇、二乙二醇和更高的聚(氧亚乙基)二醇、丙烷-1,2-二醇或聚(氧亚丙基)二醇、丙烷-1,3-二醇、丁烷-1,4-二醇、聚(氧四亚甲基)二醇、戊烷-1,5-二醇、己烷-1,6-二醇、己烷-2,4,6-三醇、甘油、1,1,1-三羟甲基丙烷、双三羟甲基丙烷、季戊甲醇和山梨醇。但合适的缩水甘油醚也可以由环脂族醇如1,3-或1,4-二羟基环己烷、二(4-羟基环己基)甲烷、2,2-二(4-羟基环己基)丙烷或1,1-二(羟基甲基)环己-3-烯获得,或它们可以拥有芳环,如N,N-二(2-羟基乙基)苯胺或p,p'-二(2-羟基乙基氨基)二苯基甲烷。
聚缩水甘油基醚或聚(β-甲基缩水甘油基)醚的特别重要的代表性物质基于单环酚例如如间苯二酚或对苯二酚、多环酚例如二(4-羟基苯基)甲烷(双酚F)、2,2-二(4-羟基苯基)丙烷(双酚A)、二(4-羟基苯基)砜(双酚S)、烷氧基化的双酚A、F或S、三元醇延伸的双酚A、F或S、溴化的双酚A、F或S、氢化的双酚A、F或S、酚的缩水甘油基醚和具有侧基或侧链的酚、酚或甲酚与甲醛在酸性条件下获得的缩合产品如酚的酚醛清漆和甲酚的酚醛清漆、或硅氧烷二缩水甘油。
聚缩水甘油酯和聚(P-甲基缩水甘油基)酯可以通过表氯醇或甘油二氯丙醇或β-甲基表氯醇与多羧酸化合物反应而产生。反应方便地在碱的存在下实施。所述多羧酸化合物可以为例如戊二酸、己二酸、庚二酸、辛二酸、壬二酸、癸二酸或二聚或三聚亚油酸。但同样地,也可以采用环脂族多羧酸,例如四氢邻苯二甲酸、4-甲基四氢邻苯二甲酸、六氢邻苯二甲酸或4-甲基六氢邻苯二甲酸。也可以应用芳族多羧酸,例如邻苯二甲酸、间苯二甲酸、偏苯三酸或均苯四甲酸或其它羧基终端的加成物,例如可以应用偏苯三酸和多元醇如甘油或2,2-二(4-羟基环己基)丙烷的加成物。
在另一个方面,环氧树脂为非缩水甘油基环氧化合物。非缩水甘油基环氧化合物在结构上可以为直链、支化或环状。例如可以包括一种或多种环氧化物化合物,其中环氧化物基团形成部分脂环或杂环系统。其它的包括带有至少一个与含至少一个硅原子的基团直接或间接键接的环氧环己基基团的含环氧基的化合物。示例在US 5,639,413中进行了公开,其在这里作为参考引入。还有其它的包括含一个或多个环己烯氧化物基团的环氧化物和含一个或多个环戊烯氧化物基团的环氧化物。
非缩水甘油基环氧化合物的具体实例包括如下双官能的非缩水甘油基环氧化物化合物,其中环氧化物基团形成部分脂环或杂环系统:二(2,3-环氧环戊基)醚、1,2-二(2,3-环氧环戊氧基)乙烷、3,4-环氧环己基-甲基3,4-环氧环乙烷羧酸酯、3,4-环氧-6-甲基-环己基甲基3,4-环氧-6-甲基环己烷羧酸酯、二(3,4-环氧环己基甲基)己二酸酯、二(3,4-环氧-6-甲基环己基甲基)己二酸酯、亚乙基二(3,4-环氧环己烷羧酸酯)、乙烷二醇二(3,4-环氧环己基甲基)。
在一些特定的方面,双官能的非缩水甘油基环氧化合物包括环脂族双官能非缩水甘油基环氧化物,如3,4-环氧环己基-甲基3',4'-环氧环己烷羧酸酯和2,2'-二-(3,4-环氧-环己基)-丙烷,其中前者最为优选。
在又一个方面,环氧树脂为聚(N-缩水甘油基)化合物或聚(S-缩水甘油基)化合物。聚(N-缩水甘油基)化合物可以通过表氯醇与含至少两个胺氢原子的胺的反应产品脱除氯化氢而获得。这些胺例如可以有n-丁基胺、苯胺、甲苯胺、间-二甲苯二胺、二(4-氨基苯基)甲烷或二(4-甲基氨基苯基)甲烷。聚(N-缩水甘油基)化合物的其它实例包括亚环烷基脲如亚乙基脲或1,3-亚丙基脲的N,N'-二缩水甘油基衍生物,和乙内酰脲如5,5-二甲基乙内酰脲的N,N'-二缩水甘油基衍生物。聚(S-缩水甘油基)化合物的实例有由二硫醇如乙烷-1,2-二硫醇或二(4-巯基甲基苯基)醚衍生的二-S-缩水甘油基衍生物。
也可以应用1,2-环氧化物基团连接到不同杂原子或官能基团的环氧树脂。实例包括4-氨基酚的N,N,O-三缩水甘油基衍生物、水杨酸的缩水甘油基醚/缩水甘油酯、N-缩水甘油基-N'-(2-缩水甘油基氧基丙基)-5,5-二甲基乙内酰脲或2-缩水甘油基氧基-1,3-二(5,5-二甲基-1-缩水甘油基乙内酰脲-3-基)丙烷。
也可以应用其它环氧化物衍生物,如乙烯基环己烯二氧化物、柠檬烯二氧化物、柠檬烯一氧化物、乙烯基环己烯一氧化物、3,4-环氧环己基甲基丙烯酸酯、3,4-环氧-6-甲基环己基甲基9,10-环氧硬脂酸酯和1,2-二(2,3-环氧-2-甲基丙氧基)乙烷。
附加地,环氧树脂可以为如上面提到的那些环氧树脂与具有可与环氧基反应的自由氢的化合物的预反应加成物。通常,这种反应性氢存在于羧酸基团、芳族羟基基团、氨基基团和氢硫基基团中。
在另一个方面,所述可固化组合物包含固化组分。以100重量份固化组分计,所述固化组分可以包含大于40重量份的聚醚胺。
在一些方面,所述聚醚胺可以选自聚醚单胺、聚醚二胺、聚醚三胺和它们的混合物。
因此,按照一个方面,所述聚醚胺是具有通式(1)或(1a)的聚醚单胺:
其中R为氢或甲基,和
a和b独立地为约1-150的整数;或
其中Y为氢或甲基,
Z为C1-C40烷基或C1-C40烷基酚基团,和
w为约1-100的整数。
在又一个方面,所述聚醚胺为具有通式(2)或(2a)的聚醚单胺:
可商购的聚醚单胺包括可由Huntsman Petrochemical LLC获得的M系列和XTJ系列胺,包括但不限于M-600、M-1000、M-2005、M-2070、XTJ-435和XTJ-436胺。
按照另一个方面,所述聚醚胺为具有通式(3)、(4)或(5)的聚醚二胺:
其中c为约2-100的整数;
其中e为约2-40的整数,和
d和f独立地为约1-10的整数;或
其中g为约2-3的整数。
可商购的聚醚二胺包括可由Huntsman Petrochemical LLC获得的D、ED和EDR胺,包括但不限于D-230、D-400、D-2000、D-4000、ED-600、ED-900、ED-20003、EDR-148和EDR-176胺。
按照另一个方面,所述固化组分包含具有通式(6)的聚醚三胺:
其中R1为氢、甲基或乙基,
n为0或1的整数,和
h、i和j独立地为约1-100的整数。
在一个具体方面,以100重量份固化组分计,固化组分包含至少50重量份的聚醚胺。在另一个方面,以100重量份固化组分计,固化组分包含至少60重量份的聚醚胺。在又一个方面,以100重量份固化组分计,固化组分包含至少70重量份或至少80重量份的聚醚胺。
在另一个方面,以100重量份固化组分计,固化组分包含大于10重量份至小于90重量份或大于20重量份至小于90重量份或大于30重量份至小于90重量份或大于40重量份至小于90重量份的聚醚胺。在另一个方面,以100重量份固化组分计,固化组分包含约55-75重量份的聚醚胺。
固化组分也可以包含第二胺。聚醚胺不能用作第二胺。因此,在一个方面,所述第二胺可以为脂族多胺,包括但不限于亚乙基二胺、二亚乙基三胺、三亚乙基四胺、四亚乙基五胺、五亚乙基六胺、二亚丙基三胺、三亚丁基四胺、六亚甲基二胺、双六亚甲基三胺、1,2-丙烷二胺、1,3-丙烷二胺、1,2-丁烷二胺、1,3-丁烷二胺、1,4-丁烷二胺、1,5-戊烷二胺、1,6-己烷二胺、2-甲基-l,5-戊烷二胺、2,5-二甲基-2,5-己烷二胺和它们的混合物。
在另一方面,所述第二胺可以为环脂族多胺,包括但不限于异佛尔酮二胺、4,4'-二氨基二环己基甲烷、甲烷二胺、1,2-二氨基环己烷、1,4-二氨基环己烷和它们的混合物。
按照另一个方面,所述第二胺可以为具有通式(7)的多胺:
其中R2和R3独立地为脂族或环脂族基团,和
k和p独立地为1-3的整数。
按照另一个方面,所述第二胺可以为具有通式(8)的多胺:
其中R4为氢、甲基或乙基基团,和
q和t独立地为约1-10的整数。
按照一个方面,以100重量份固化组分计,固化组分包含小于约30重量份的第二胺。在另一个方面,以100重量份固化组分计,固化组分包含小于约25重量份和甚至小于约20重量份的第二胺。
在又一个方面,以100重量份固化组分计,固化组分包含约10-30重量份的第二胺。在又一个方面,以100重量份固化组分计,固化组分包含约17.5-27.5重量份的第二胺。
在一个实施方案中,聚醚胺和第二胺在固化组分中以50:50-95:5或60:40-90:10或70:30-85:15的聚醚胺与第二胺的比存在。
以100重量份固化组分计,固化组分还包含大于1重量份或大于2重量份或大于3重量份或大于4重量份的促进剂。
在一个实施方案中,所述促进剂为咪唑。在一个具体方面,所述咪唑为每个分子具有一个咪唑环的化合物,如咪唑、2-甲基咪唑、2-乙基-4-甲基咪唑、2-甲基-4-乙基咪唑、2-十一烷基咪唑、2-十七烷基咪唑、2-苯基咪唑、2-苯基-4-甲基咪唑、l-苯甲基-2-甲基咪唑、2-乙基咪唑、2-异丙基咪唑、2-苯基-4-苯甲基咪唑、1-氰基乙基-2-甲基咪唑、1-氰基乙基-2-乙基-4-甲基咪唑、1-氰基乙基-2-十一烷基咪唑、1-氰基乙基-2-异丙基咪唑、1-氰基乙基-2-苯基咪唑、2,4-二氨基-6-[2'-甲基咪唑基-(l)']-乙基-s-三嗪、2,4-二氨基-6-[2'-乙基-4-甲基咪唑基-(l)']-乙基-s-三嗪、2,4-二氨基-6-[2'-十一烷基咪唑基-(l)']-乙基-s-三嗪、2-甲基-咪唑鎓异氰脲酸加成物、2-苯基咪唑鎓-异氰脲酸加成物、l-氨基乙基-2-甲基咪唑、2-苯基-4,5-二羟基甲基咪唑、2-苯基-4-甲基-5-羟基甲基咪唑、2-苯基-4-苯甲基-5-羟基甲基咪唑、1,2-二甲基咪唑和它们的混合物。
在另一个方面,所述咪唑为每个分子含2或更多个咪唑环的化合物,其可以通过上面提到的含羟基甲基的咪唑化合物如2-苯基-4,5-二羟基甲基咪唑、2-苯基-4-甲基-5-羟基甲基咪唑和2-苯基-4-苯甲基-5-羟基-甲基咪唑进行脱水和使它们与甲醛缩合获得,例如4,4'-亚甲基-二-(2-乙基-5-甲基咪唑)。
在一个实施方案中,所述促进剂为叔胺。叔胺可以选自N-乙基吗啉、异丙基吗啉、N-丁基吗啉、甲氧基乙基吗啉、羟基乙基吗啉、2,2′-二吗啉代二乙基醚、N,N′-二吗啉代乙烷、甲基二乙醇胺、N,N-二甲基环己胺、甲基二环己胺、N,N,N'-三甲基-N'-(2-羟基乙基)二(2-氨基乙基)醚、二-(2-二甲基氨基乙基)醚、N,N′-二甲基哌嗪、1,3,5-三(3-(二甲基氨基)丙基)-六氢-s-三嗪、2,4,6-三(二甲基氨基甲基)酚和它们的组合。
在另一个实施方案中,所述促进剂可以为选自如下的叔胺:N-乙基吗啉、异丙基吗啉、N-丁基吗啉、甲氧基乙基吗啉、羟基乙基吗啉、2,2′-二吗啉代二乙基醚、N,N′-二吗啉代乙烷、甲基二乙醇胺、N,N,N'-三甲基-N'-(2-羟基乙基)二(2-氨基乙基)醚、二-(2-二甲基氨基乙基)醚、N,N′-二甲基哌嗪、1,3,5-三(3-(二甲基氨基)丙基)-六氢-s-三嗪和它们的组合,和所述固化组分为基本不含环状碳酸酯、胍及其衍生物和芳族胺的固化组分。
在另一个实施方案中,所述促进剂为咪唑和叔胺,所述叔胺选自:N-乙基吗啉、异丙基吗啉、N-丁基吗啉、甲氧基乙基吗啉、羟基乙基吗啉、2,2′-二吗啉代二乙基醚、N,N′-二吗啉代乙烷、甲基二乙醇胺、N,N-二甲基环己胺、甲基二环己胺、N,N,N'-三甲基-N'-(2-羟基乙基)二(2-氨基乙基)醚、二-(2-二甲基氨基乙基)醚、N,N′-二甲基哌嗪、1,3,5-三(3-(二甲基氨基)丙基)-六氢-s-三嗪、2,4,6-三(二甲基氨基甲基)酚和它们的组合。
按照一个方面,以100重量份固化组分计,固化组分包含大于约5重量份的促进剂。在另一个方面,以100重量份固化组分计,固化组分包含大于约7.5重量份的促进剂。在另一个方面,以100重量份固化组分计,固化组分包含大于约10重量份和甚至大于约20重量份的促进剂。
在又一个方面,以100重量份固化组分计,固化组分包含小于约30重量份的促进剂。在另一个方面,以100重量份固化组分计,固化组分包含小于约25重量份和甚至小于约20重量份的促进剂。
在另一个方面,以100重量份固化组分计,固化组分包含大于约1重量份至约30重量份的促进剂。在另一个方面,以100重量份固化组分计,固化组分包含约7.5-25重量份的促进剂。在又一个方面,以100重量份固化组分计,固化组分包含约10-20重量份的咪唑。
在又一个方面,本发明的可固化组合物可以任选包含对于其打算用途来说有用的一种或多种其它添加剂。例如,在可固化组合物中有用的任选添加剂可以包括但不限于稀释剂(1,4-丁烷二醇二缩水甘油基醚(BDDGE)、1,6己烷二醇二缩水甘油基醚(HDDGE)、甲酚二缩水甘油基醚(CGE)、C12-14烷基缩水甘油基醚(AGE)、三羟甲基丙烷三缩水甘油基醚(TMPTGE))、惰性填料、增强纤维、稳定剂、表面活性剂、流动改进剂、颜料或染料、剥离剂、消光剂、脱气剂、阻燃剂(例如无机阻燃剂、卤代阻燃剂和非卤代阻燃剂如含磷材料)、增韧剂(如羧基终端的液态丁腈橡胶(CTBN)、丙烯酸终端的液态丁腈橡胶(ATBN)、环氧终端的液态丁腈橡胶(ETBN)、弹性体和预先形成的核壳橡胶的液态环氧树脂(LER)加成物)、固化引发剂、固化抑制剂、湿润剂、加工助剂、荧光化合物、UV稳定剂、抗氧化剂、抗冲改性剂和它们的混合物。
当在可固化组合物中包含增强纤维时,所述纤维可以为连续、剁碎和/或织物形式。可以应用已知或通常的纤维,和可以包括但不限于碳纤维(例如聚丙烯腈(PAN)基碳纤维、沥青基碳纤维和气相生长碳纤维)、玻璃纤维、芳纶、硼纤维、石墨纤维、碳化硅纤维、高强度聚乙烯纤维、碳化钨纤维、聚-p-亚苯基苯并唑纤维(PBO纤维)和它们的混合物。在这些当中,从机械性能(如硬度)看,碳纤维、玻璃纤维和芳纶是优选的。特别优选碳纤维。
纤维形式的例子可以包括但不限于细丝形式(连续纤维)、丝束、包含单向对齐丝束的单向材料、织造织物和非织造织物。这种纤维的织造织物的实例包括平面织物、斜纹织物、缎纹织物和拼接片,所述拼接片的代表有非屈曲织物和通过制备包含单向对齐纤维束的片或包含改变层压角层压纤维束的片,并将所述片进行拼接以产生整体的织物而产生。
以100重量份可固化组合物计,本发明可固化组合物中的增强纤维浓度可以为约0.2-95重量份或约0.2-70重量份和甚至约0.2-60重量份。
配制可固化组合物
可固化组合物可以通过搅拌和混合一定状态的组分而制备,没有特殊的限制,所述状态如果需要,组分可以加热。本发明的可固化组合物可以应用之前混合的组分作为1个包类型的组合物原样应用。另外,可固化组合物也可以应用多个包类型(例如2个包类型)的组合物,所述各个包通过在使用前以预定比混合两个或更多个单独制备的组分获得。搅拌/混合方法不特别限定。例如,可以应用已知或常用的搅拌/混合装置如混合器(如溶解器或均化器)、捏合器、辊、球磨机或行星式搅拌设备。搅拌和混合后,可以使混合物在真空中去除泡沫。
在一个方面,通过在容器中混合包括环氧树脂和固化组分的组分,和然后使各组分配制成可固化组合物,由此获得本发明的可固化组合物。混合顺序不是很关键,即可以以任何顺序混合组分从而提供本发明的可固化组合物。在混合过程中或混合前可以向组合物中加入任意上述任选的添加剂如填料或增强纤维,以形成可固化组合物。
在可固化组合物中,固化组分中反应性胺氢的当量数与可固化组合物中存在的环氧化物的当量数之间的比(即可固化组合物的“胺/环氧化学计量比”)为约0.2-1.3,或约0.4-1,或甚至约0.4-0.9,或仍甚至约0.5-0.85,和仍甚至约0.6-0.8,和在某些情况中为约0.65-0.75。在其它方面,环氧树脂与固化组分的重量比可以为至少约1:1,和仍甚至为至少1.2:1,和甚至为至少约1.5:1。在其它方面,环氧树脂与固化组分的重量比可以为至少约2:1,和仍甚至为至少2.5:1,和甚至为至少约3:1。
可以在能够制备对于所需用途来说具有低粘度的有效的可固化组合物的温度下混合和分散组分。混合组分期间的温度通常可以为约0-100℃或约0-50℃。
在另一个方面,本发明提供制备树脂涂覆的基质的方法。所述方法步骤包括使基质与本发明的可固化组合物接触。本发明的组合物可以通过本领域熟练技术人员已知的任何方法与基质接触。这种接触方法的实例包括但不限于浸涂、喷涂、模涂、辊涂、树脂灌注处理,和使基质与含可固化组合物浴液接触。所述基质例如可以为塑料、玻璃、合金、金属、陶瓷、木材、水泥、混凝土、橡胶或增强纤维材料。
按照另一个方面,一旦与任何合适基质混合和接触,可固化组合物可以按工业上形成固化产品所实施的典型方法进行固化。典型的固化方法包括应用热、辐射或能源组合的环境温度至高温固化。可固化组合物可以在一个步骤或多个步骤中固化,如在复合物工业中经常实施的A、B级固化。或者,在初始固化周期后,可以应用不同温度或能源对可固化组合物进行后固化。
因此,本发明也提供通过如下方法获得的固化制品:使任何合适的基质与可固化组合物接触和应用热、辐射或能源组合固化所述可固化组合物。在一个方面,固化可以以约0-230℃或约60-110℃的温度下为可固化组合物施用热约1分钟至约8小时或约30分钟至约4小时的时间而热实现。任选地,固化制品的模塑形式可以在约100-200℃的温度下在真空下进一步后固化约30分钟至约12小时的时间。这理想地产生均质无空隙的完全固化制品。
另外,通过使待粘接的相似或不同基质的一个或多个表面在足以固化可固化组合物的条件下与可固化组合物接触,本发明的可固化组合物可以用于将一种或多种基质粘接在一起的方法中。所述条件为本领域熟练技术人员通常在现有已知方法中实施的那些条件,和可以包括压力和/或热的应用。
在一个替代方面,通过固化本发明的可固化组合物,可以通过工业中公知的技术例如拉挤、灌注、模制、封装或涂覆获得复合制品。因此,本发明的可固化组合物可以用于生产复合制品的方法中,如铸造件、预浸料、粘接片、层压件和金属箔板层叠片。对于特定用途,通过加入增强纤维可以定制复合制品的特性。
因此,在另一个方面,提供生产复合制品的方法,包括如下步骤:(i)提供增强纤维的层或束;(ii)提供可固化组合物;(iii)使增强纤维与可固化组合物接触以涂覆和/或浸渍增强纤维;和(iv)在至少约60℃或至少约120℃或甚至至少约195℃的温度下固化所涂覆和/或浸渍的增强纤维。
涂覆和/或浸渍可以通过湿法或热熔法实施。在湿法中,首先将可固化组合物溶解于溶剂中以降低粘度,随后实施增强纤维的涂覆和/或浸渍,和应用烤箱或类似物蒸发掉溶剂。在热熔法中,通过用已经被加热降低粘度的可固化组合物直接涂覆和/或浸渍增强纤维实施涂覆和/或浸渍,或者替代地可以在剥离纸或类似物上首先产生可固化组合物的涂覆膜,和将所述膜放置于增强纤维的一面或两面上,和施用热和压力以实施组合物的涂覆和/或浸渍。
按照另一个方面,提供在RTM系统中生产复合制品的方法。所述方法包括如下步骤:a)向模具中引入包含增强纤维的纤维预制件;b)向模具中注入可固化组合物,c)使所述可固化组合物浸渍所述纤维预制件;和d)在至少约60℃或至少约120℃或甚至至少约195℃的温度下加热所述树脂浸渍的预制件一段时间,以产生至少部分固化的复合制品;和e)任选在约100-250℃的温度下使所述部分复合固体制品进行后固化操作。
在一个替代方面,本发明提供在VaRTM系统中形成复合制品的方法。所述方法包括如下步骤:a)向模具中引入包含增强纤维的纤维预制件;b)向模具中注入可固化组合物,c)减小模具内的压力;d)维持所述模具在接近减压的条件下;e)使所述可固化组合物浸渍所述纤维预制件;和f)在至少约60℃或至少约120℃或甚至至少约195℃的温度下加热所述树脂浸渍的预制件一段时间,以产生至少部分固化的复合制品;和e)任选在约100-250℃的温度下使所述至少部分固化的复合制品进行后固化操作。
本发明的固化制品和复合制品可以用于各种用途,例如航空航天领域,其中它们可以用作航空器的主要结构材料(主翼、尾翼、底梁等)、次要结构材料(襟翼、副翼、整流罩、流线壳、内饰等)、火箭发动机壳、人造卫星的结构材料等。另外,它们可以用作移动物体如小汽车、船和铁路客车、传动轴、燃料电池、板簧、风力涡轮机叶片、压力容器、飞轮、造纸压辊、土建工程和建筑材料(屋顶材料、缆绳、钢筋、改造材料)等结构材料。本发明的固化制品和复合制品也可以用作高压罐如氢罐和液化天然气(LNG)罐的组分材料。
在另一个方面,所述可固化组合物用于在模具中生产风力涡轮机叶片。所述模具可以内衬或不内衬纤维增强材料和/或可以向可固化组合物附加添加其它纤维增强材料。所述纤维增强材料可以为织造织物、单轴和多轴无纬织物、无纺布和如下纤维材料的短纤维:玻璃纤维、碳纤维、芳纶、PE纤维(Dyneema)和玄武岩纤维。
风力涡轮机叶片优选通过如下方法生产:其中提供相应的模具,将可固化组合物引入该模具中,和只有在模具已完全充满时完全固化所述可固化组合物。在大多数实施方案中通过灌注技术将可固化组合物引入相应的模具中。在这种情况下为模具施用真空。这种真空在温度低于初始固化温度下在抽吸作用下将可固化组合物抽入模具,从而在注入操作过程中粘度保持基本不变,和在完全固化前模具的所有区域均已被充满。随后在至少60℃例如60-150℃的温度下在模具中完全固化所述可固化组合物。
实施例
对于实施例1a-1f、2a-2f和3a-3f,使D-230聚醚胺和异佛尔酮二胺的混合物以70/30的重量比混合,然后加入到环氧树脂(Hexion MGSTM RIMR 235树脂)中,随后加入不同量的咪唑(参见下表1)。
表1
然后用DSC测量玻璃转化温度和其结果在下表2给出:
表2
还用流变仪测量固化曲线,和结果示于图1、2和3。
通过如下过程制备附加的实施例(在表3和4中示出):使D-230聚醚胺(由Huntsman Corp.或其关联公司获得)和异佛尔酮二胺的混合物以70/30或85/15的重量比混合,然后加入到环氧树脂(Hexion MGSTM RIMR 235树脂)中,随后加入不同量的选自N-甲基吗啉(“NMM”)、N-乙基吗啉(“NEM”)、N-丁基吗啉(“NBM”)、甲氧基乙基吗啉(“MEM”)、2,2′-二吗啉代二乙基醚(“DMDEE”)和N,N′-二吗啉代乙烷(“DMORE”)的叔胺。制备没有任何叔胺的对比样品。表3和4中给出了各实施例的细节。
对于包含重量比为70/30的D-230聚醚胺和异佛尔酮二胺的各实施例,在表3中列出了等温固化数据曲线,而表4列出了包含重量比为85/15的D-230聚醚胺和异佛尔酮二胺的各实施例的等温固化数据曲线。应用来自TA Instruments的AR2000ex流变仪在40℃测量等温固化数据曲线。如在表3-5中所应用,术语“phr”指每100份环氧树脂的份数。
表3
表4
由表3和表4可以看出,应用具体叔胺实际上通过减小树脂系统中粘度的累积使系统慢了下来(即增加了开放时间)。实施例8-11的玻璃转化温度在图4中作为化学结构的函数进行了描绘。由图4可以看出,附着于氮原子上的取代基团越大,获得的Tg越低。
通过如下方法制备其它实施例:通过混合D-230聚醚胺和异佛尔酮二胺在不同重量比下的混合物,然后将其加入到含双酚A(DGEBA)环氧树脂的二缩水甘油基醚的环氧树脂和含缩水甘油基的反应性稀释剂中,随后加入四甲基胍(“TMG”)或二吗啉代二乙基醚(“DMDEE”)。在没有TMG或DMDEE的情况下制备附加的对比例。表5给出了各实施例的细节。
对于大多数实施例,应用AR 2000ex流变仪在30℃测量等温粘度曲线,并在下表5中给出达到1000mPa.s和10,000mPa.s所花的时间。
表5
表6给出了表5描述的实施例15、27、16和29的可固化组合物的固化产品的机械特性。所述固化产品通过在70℃下加热可固化组合物6小时产生。所述机械特性应用Zwick测试机按ISO/ASTM标准进行测量。硬度应用Shore D硬度计标注数字硬度的测试仪和标准程序进行测量。
表6
表5和6表明相比于不含促进剂或TMG的类似组合物,含DMDEE的组合物在打开时间方面有所增加,但相比于含例如TMG的类似的固化组合物,由含DMDEE的可固化组合物得到的固化组合物没有表现出任何机械特性的降低。
虽然上文已详细描述了本发明各种实施方案的制备和应用,但应理解本发明提供了许多可应用的发明概念,所述概念可以在多种具体情况中实施。这里所讨论的具体实施方案只是制备和应用本发明的示例性方法,和不限制本发明的范围。
Claims (9)
1.可固化组合物,包含:
(i)环氧树脂;和
(ii)包含聚醚胺和叔胺的固化组分,其中所述叔胺选自N-乙基吗啉、异丙基吗啉、N-丁基吗啉、甲氧基乙基吗啉、羟基乙基吗啉、2,2′-二吗啉代二乙基醚、N,N′-二吗啉代乙烷和它们的组合,以100重量份固化组分计,所述固化组分包含0.5-7.5重量份的叔胺,其中所述固化组分还包含第二胺,其中聚醚胺和第二胺在所述固化组分中以82:18-95:5的聚醚胺与第二胺的比存在。
2.权利要求1的可固化组合物,其中所述固化组分还包含咪唑。
3.权利要求1的可固化组合物,其中所述叔胺选自:N-乙基吗啉、异丙基吗啉、N-丁基吗啉、甲氧基乙基吗啉、羟基乙基吗啉、2,2′-二吗啉代二乙基醚、N,N′-二吗啉代乙烷和它们的组合,和其中所述可固化组合物基本不含环状碳酸酯、胍及其衍生物和芳族胺。
4.权利要求1-3任一项的可固化组合物,其中所述第二胺为环脂族聚胺。
5.生产可固化组合物的方法,包括:
-在容器中使环氧树脂和固化组分混合,所述固化组分包含聚醚胺和叔胺,其中所述叔胺选自N-乙基吗啉、异丙基吗啉、N-丁基吗啉、甲氧基乙基吗啉、羟基乙基吗啉、2,2′-二吗啉代二乙基醚、N,N′-二吗啉代乙烷和它们的组合,以100重量份固化组分计,所述固化组分包含0.5-7.5重量份的叔胺,其中所述固化组分还包含第二胺,其中聚醚胺和第二胺在所述固化组分中以82:18-95:5的聚醚胺与第二胺的比存在;和
-使所述环氧树脂和固化组分配制成可固化组合物。
6.制备固化制品的方法,包括使基质与权利要求1的可固化组合物接触,和固化所涂覆的基质以形成固化制品。
7.权利要求6的方法,其中所述基质包括塑料、玻璃、合金、金属、陶瓷、木材、水泥、混凝土、橡胶或增强纤维材料中的一种。
8.生产复合制品的方法,包括如下步骤:(i)提供增强纤维的层或束;(ii)提供权利要求1的可固化组合物;(iii)使增强纤维与可固化组合物接触以涂覆和/或浸渍所述增强纤维;和(iv)在至少60℃的温度下固化所涂覆和/或浸渍的增强纤维。
9.按权利要求8的方法生产的复合制品。
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