CN1396938A - 环氧树脂组合物 - Google Patents
环氧树脂组合物 Download PDFInfo
- Publication number
- CN1396938A CN1396938A CN01804387A CN01804387A CN1396938A CN 1396938 A CN1396938 A CN 1396938A CN 01804387 A CN01804387 A CN 01804387A CN 01804387 A CN01804387 A CN 01804387A CN 1396938 A CN1396938 A CN 1396938A
- Authority
- CN
- China
- Prior art keywords
- composition
- component
- vulcabond
- epoxy
- amine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 229920000647 polyepoxide Polymers 0.000 title description 6
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 8
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000002118 epoxides Chemical class 0.000 claims abstract description 6
- 239000011253 protective coating Substances 0.000 claims abstract description 4
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims abstract 2
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- KQWGXHWJMSMDJJ-UHFFFAOYSA-N cyclohexyl isocyanate Chemical compound O=C=NC1CCCCC1 KQWGXHWJMSMDJJ-UHFFFAOYSA-N 0.000 claims description 2
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- 238000002360 preparation method Methods 0.000 description 10
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- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 8
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/798—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing urethdione groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/58—Epoxy resins
- C08G18/581—Reaction products of epoxy resins with less than equivalent amounts of compounds containing active hydrogen added before or during the reaction with the isocyanate component
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
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Abstract
一种组合物，其包括：(A)每分子含有至少两个环氧基团的环氧化物，(B)每分子含有至少两个羟基的多元醇或每分子含有至少两个氨基氢原子的伯胺或仲胺，和(C)含有至少两个异氰酸酯基团的固体化合物；该组合物显示出高储存稳定性，且可用作防护涂料或粘合剂。
Description
本发明涉及含有两种具有不同反应性的固化剂的环氧树脂组合物，生产单组分热固性树脂组合物的方法，所说的单组分热固性树脂组合物作为防护涂料或粘合剂的用途，和通过固化所说的单组分热固性树脂组合物获得的交联产品。
工业上在不断地寻找能以简单的方法制备的新材料，它贮存稳定、应用方便和甚至能提供增加的更多种易设计的(tailrable)性能。
因为环氧树脂基体系的用途广、品种多，其对于粘合剂和复合材料来说是重要的基础树脂，且在许多应用领域(航空领域、汽车领域、工业、消费领域等)是最有用的。
环氧树脂体系进行的主要反应是同胺、酸、酸酐等进行的加成型反应(催化或不催化)。配方可以是单组分型(包括环氧树脂和硬化剂的稳定的混合物)或双组分型(其中反应物同环氧树脂在应用前混合)。单组分型应用更简单，有较少的包装废料；然而，需要更仔细以保证不会发生早期反应，以导致使用前贮存期短。传统的热熔融和热固化粉末环氧树脂组合物，其能由环氧树脂和包含胺固化体系和潜硬化剂的硬化剂组合物制备，公开在US专利No.5708120、WO97/19124和WO97/19125中。
异氰酸酯也是备受关注的，因为其能同羟基、氨基和其它含活性氢的基团进行快速亲核加成反应，于是生成尿烷和脲产品。为了在单组分体系中使用异氰酸酯，生产稳定化的/失活的异氰酸酯分散体或具有脲或尿烷壳的粉末是公知的，例如从US专利No.4483974中可知。US专利No.4067843描述了由已经共聚的聚异氰酸酯和羟基封端聚二烯烃的混合物来制备颗粒状的酚-尿烷化合物的方法。这些颗粒用作热固性粘合剂。
传统的含有以胺或酸酐作为潜固化剂的环氧树脂体系具有这样的缺点，即最后的固化在相对高的温度(180～220℃)下进行。
目前已经发现环氧树脂、聚酰胺或多元醇和固体异氰酸酯的混合物形成了易设计的、贮存稳定的单组分组合物，其在室温下发生凝胶或固化，且能在60～180℃下完全固化。
因此，本发明涉及一种组合物，包括：
(A)每分子含有至少两个环氧基团的环氧化物，
(B)每分子含有至少两个羟基的多元醇或每分子含有至少两个氨基氢原子的伯胺或仲胺，和
(C)含有至少两个异氰酸酯基团的固体化合物。
根据本发明适合用于组合物制备的组分(A)是通常在环氧树脂技术中使用的环氧树脂。环氧树脂的实例是：
I)聚缩水甘油酯和聚(β-甲基缩水甘油)酯，其分别通过在分子中具有至少两个羧基的化合物同表氯醇或β-甲基表氯醇反应获得，该反应优选在碱存在下进行。
可以用作在分子中具有两个羧基的化合物，有脂族多羧酸。这样的多羧酸的实例是草酸，琥珀酸、戊二酸、己二酸、庚二酸、辛二酸、壬二酸和二聚亚油酸或三聚亚油酸。
然而，也可能使用脂环族多羧酸，例如四氢邻苯二甲酸、4-甲基四氢邻苯二甲酸、六氢邻苯二甲酸和4-甲基-六氢邻苯二甲酸。
也可以使用芳族多羧酸，例如邻苯二甲酸、间苯二甲酸和对苯二甲酸。
II)聚缩水甘油醚或聚(β-甲基缩水甘油)醚，其分别通过具有至少两个游离醇羟基和/或酚羟基的化合物同表氯醇或β-甲基表氯醇反应获得，在碱性条件或在酸催化剂的存在下随后进行碱处理。
这样的缩水甘油醚得自例如，无环醇，如乙二醇、二甘醇或高级聚乙二醇、丙烷-1，2-二醇或聚丙二醇、丙烷-1，3-二醇、丁烷-1，4-二醇、聚氧化四亚甲基二醇、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、季戊四醇、山梨醇和也得自聚表氯醇。
这样的缩水甘油醚进一步得自脂环族醇，如1，4-环己烷二甲醇、二(4-羟环己基)甲烷或2，2-二(4-羟环己基)-丙烷，或得自含有芳基和/或另一些官能团的醇，如N，N-二(2-羟乙基)苯胺或p，p’-二(2-羟乙基氨基)二苯基甲烷。该缩水甘油醚可以基于单核苯酚，例如间苯二酚或对苯二酚，或基于多核苯酚，例如二(4-羟苯基)甲烷、4，4’-二羟基二苯、二(4-羟苯基)砜、1，1，2，2-四(4-羟苯基)乙烷、2，2-二(4-羟苯基)丙烷或2，2-二(3，5-二溴-4-羟苯基)丙烷。另外的对于缩水甘油醚制备合适的羟基化合物为线型酚醛清漆，其由醛如甲醛、乙醛、氯醛或糠醛，同非取代或用氯原子或C1～C9的烷基取代的苯酚或双酚例如苯酚、4-氯苯酚、2-甲基苯酚或4-叔丁基苯酚的缩聚获得。
III)聚(N-缩水甘油)化合物，其由表氯醇和含有至少两个氨基氢原子的胺的反应产物的脱氯化氢反应获得。这些胺是，例如，苯胺、正丁基胺、二(4-甲氨基苯基)甲烷、间-二甲苯-二胺或二(4-甲基氨基苯基)甲烷。
然而，聚(N-缩水甘油)化合物也包括：异氰脲酸三缩水甘油酯、环亚烷基脲的N，N-二缩水甘油衍生物，如亚乙基脲或1，3-亚丙基脲，和乙内酰脲的二缩水甘油衍生物，如5，5-二甲基乙内酰脲。
IV)聚(S-缩水甘油)化合物，例如二(S-缩水甘油)衍生物，得自二硫酚，例如乙烷-1，2-二硫酚或二(4-巯甲基苯基)醚。
V)脂环族环氧树脂，例如二(2，3-环氧环戊基)醚、2，3-环氧-环戊基缩水甘油醚、1，2-二(2，3-环氧环戊氧基)乙烷或3，4-环氧环己基甲基-3’，4’-环氧环己烷羧酸酯。
作为替换的是，可以使用这样的环氧树脂，其中1，2-环氧基(epoxide group)键合到不同的杂原子和/或官能团上；这些化合物包括，例如，4-氨基苯酚的N，N，O-三缩水甘油衍生物，水杨酸的缩水甘油醚-缩水甘油酯，N-缩水甘油基-N’-(2-缩水甘油丙氧基)-5，5-二甲基乙内酰脲和2-缩水甘油氧基-1，3-二(5，5-二甲基-1-缩水甘油乙内酰脲-3-基)丙烷。
为制备本发明的组合物，优选使用二缩水甘油醚或酯。
特别优选作为组分(A)的是双酚A的二缩水甘油醚和双酚F的二缩水甘油醚。
所提到的本发明混合物的组分(B)可以是，任何一种具有至少两个羟基的多元醇或任何一种具有至少两个氨基氢原子的胺。
适合的多元醇是脂族和芳族多元醇。
合适的脂族多元醇的实例是乙二醇、二甘醇、聚乙二醇、丙二醇、聚丙二醇、丙烷-1，3-二醇、丁烷-1，4-二醇、戊烷-1，5-二醇、己烷-1，6-二醇、己烷-1，2，3-三醇、丙三醇、1，1，1-三羟甲基丙烷、季戊四醇和山梨醇。
合适的芳族多元醇是，例如，间苯二酚、对苯二酚、N，N-二-(2-羟乙基)苯胺、p，p-二(2-羟乙基氨基)二苯基甲烷、二(4-羟苯基)甲烷、4，4’-二羟基二苯、二-(4-羟苯基)砜、1，1，2，2-四(4-羟苯基)乙烷、2，2-二(4-羟苯基)丙烷、2，2-二(3，5-二溴-4-羟苯基)丙烷、苯酚线型酚醛清漆和甲酚线型酚醛清漆。
作为组分(B)的胺可以是脂族、脂环族、芳族和杂环胺，如二(4-氨基苯基)甲烷、苯胺/甲醛树脂、苄胺、正辛基胺、丙烷-1，3-二胺、2，2-二甲基-1，3-丙二胺、六亚甲基二胺、二亚乙基三胺、二(3-氨基丙基)胺、N，N-二(3-氨基丙基)甲胺、三亚乙基四胺、四亚乙基五胺、五亚甲基六胺、2，2，4-三甲基己烷-1，6-二胺、间二甲苯二胺、1，2-和1，4-二氨基环己烷、二(4-氨基环己基)甲烷、二(4-氨基-3-甲基环己基)甲烷、2，2-二(4-氨基环己基)丙烷、哌嗪、3-氨基甲基-3，5，5-三甲基环己基胺(异佛尔酮二胺)、聚氨基咪唑啉、聚氨基酰胺、聚氧化烯胺(例如Texaco生产的Jeffamines)、1，14-二氨基-4，11-二氧十四烷、二亚丙基三胺、2-甲基-1，5-戊二胺、N，N’-二环己基-1，6-己二胺、N，N’-二甲基-1，3-二氨基丙烷、N，N’-二乙基-1，3-二氨基丙烷、N，N-二甲基-1，3-二氨基丙烷、仲(secondary)聚氧化丙烯二胺和-三胺、2，5-二氨基-2，5-二甲基己烷、二(氨基甲基)-三环戊二烯、间氨基苄基胺、1，8-二氨基烷、二(4-氨基-3，5-二甲基环己基)甲烷、1，3-二(氨基甲基)环己烷、二苯基胺、二(4-氨基-3，5-二乙苯基)甲烷、3，5-二乙基甲苯-2，4-二胺和3，5-二乙基甲苯-2，6-二胺。
公开于US专利No.5275853中的聚醚胺也适合用作本发明组合物中的组分(B)。
优选，组分B是脂族或脂环族胺。
特别优选环己基胺、4，4’-二氨基二环己基甲烷、4，4’-二氨基-3，3’-二甲基二环己基-甲烷、2，2-二(4-氨基环己基)丙烷和2，2-二(4-氨基-3-甲基环己基)丙烷。
组分C是含异氰酸酯基团的化合物或含异氰酸酯基团化合物的混合物，它们在室温下是固体。
优选组分C以粉末的形式应用。
在本发明组合物中用作组分(C)的聚异氰酸酯包括低粘度的脂族、脂环族和芳族异氰酸酯和它们的混合物。
优选，组分C是二异氰酸酯单体、二异氰酸酯二聚物、二异氰酸酯三聚物或二异氰酸酯和脂族二醇的固体反应产物。
适合的聚异氰酸酯的实例是2，4-二苯基甲烷异氰酸酯、4，4-二苯基甲烷二异氰酸酯、己烷-1，6-二异氰酸酯、环己烷-1，2-二异氰酸酯、环己烷-1，3-二异氰酸酯、环己烷-1，4-二异氰酸酯、4，4’-二环己基甲烷二异氰酸酯、异佛尔酮二异氰酸酯、亚苯基二异氰酸酯、二甲苯二异氰酸酯、甲苯-2，4-二异氰酸酯、甲苯-2，6-二异氰酸酯、萘-1，4-二异氰酸酯、4，4’-二苯基醚二异氰酸酯、4，4’-二苯基砜二异氰酸酯、2，2-二(4-异氰酸苯基)丙烷和3，3’，4，4’-二苯基甲烷四异氰酸酯。
也能使用多元醇改性的聚异氰酸酯和液态聚异氰酸酯同较高分子量的聚异氰酸酯或碳化二亚胺聚异氰酸酯的混合物
进一步适合的聚异氰酸酯是上述多价异氰酸酯的二聚物和三聚物；这样的聚异氰酸酯有末端游离的异氰酸酯基团，且含有一个或多个uretdione和/或异氰脲酸酯环。
特别优选的聚异氰酸酯是2，4-甲苯二异氰酸酯、2，6-甲苯二异氰酸酯、2，3-甲苯二异氰酸酯、3，4-甲苯二异氰酸酯、4，4’-二苯基甲烷二异氰酸酯、2，2’-二苯基甲烷二异氰酸酯、对亚苯基二异氰酸酯、异佛尔酮二异氰酸酯和4，4’-亚甲基-二(环己基异氰酸酯)
在本发明的固化组合物中，组分(A)、(B)和(C)的相对量能在宽范围内变化。
有目的的是，组分(B)采用这样的量：对应组分(A)的每个环氧基，分别存在0.05～0.60，优选0.1～0.4个羟基和氨基氢原子。
固化产物的交联密度能通过组分(C)的量来调节。优选，本发明组合物含有组分(C)的量为：对应组分(A)的每个环氧基，存在0.05～1.00，优选0.1～0.5个异氰酸酯基团。
本发明的组合物，在适当时，可以进一步包括促进剂，如咪唑和苄基二甲基胺。
然而，可固化的混合物可以包括填料，如金属粉末，木屑，玻璃粉末，玻璃珠，半金属氧化物和金属氧化物如SiO2(二氧化硅气凝胶、石英、石英粉末、熔融二氧化硅粉末)、金刚砂和氧化钛，半金属氮化物和金属氮化物如氮化硅、氮化硼和氮化铝，半金属碳化物和金属碳化物(SiC)，金属碳酸盐(白云石、Amine 2lk、CaCO3)，金属硫化物(重晶石、石膏)，主要来自硅酸盐系列的矿物填料和天然或合成的矿物质，如沸石(特别是分子筛)、滑石、云母、高岭土、硅灰石、斑脱土和其它。
除了上述添加剂，可固化的混合物可进一步包括传统的助剂，例如抗氧化剂、光稳定剂、增塑剂、着色剂、颜料、触变剂、增韧剂、防沫剂、抗静电剂、滑动剂(glidant)和脱模辅助剂。
本发明的组合物可以通过手混合或通过使用已知的混合设备来制备，混合设备如搅拌器、捏合机或滚筒。在固体环氧树脂的情况下，分散也可以在熔融下进行。选择分散过程中的温度，使得在混合过程中不会发生早期固化。最佳固化条件有赖于微凝胶，有赖于含氮碱的类型和数量，有赖于环氧树脂和分散的形式，且能通过本领域技术人员在每种情况下用已知方法测得。
因为使用两种不同反应性的硬化剂，本发明的组合物能在两步方法中固化。混合后，环氧树脂(A)在室温或在稍微升高的温度下同多元醇或聚酰胺(B)反应：粘度的增加因而说明了该所谓的B-阶段固化的程度。通过室温下的固化步骤获得的产物通常显示出良好的粘着性和表现出优良的储存稳定性。
在要求较高温度(60～180℃)的第二固化步骤中，在第一固化步骤中形成的仲羟基同组分(C)的异氰酸酯基团反应。通过该C-阶段固化获得的交联产物特性在于优良的搭接剪切强度。
本发明进一步涉及制备凝胶、糊状物或粉末形式的单组分热固性树脂组合物的方法，该方法包括：混合根据权利要求1的混合组分(A)、(B)和(C)，在＜50℃的温度下反应混合物，直到混合物的粘度高出初始粘度至少10％。
通过B-阶段固化获得的储存稳定的单组分树脂组合物，特别可用作防护涂料或粘合剂。
本发明进一步涉及通过在60～180℃下固化单组分热固性树脂组合物获得的交联产物。
实施例是本发明的解释，因此不意在限制本发明的保护范围，在实施例中，使用下列成分：
环氧树脂1：液态双酚A二缩水甘油醚，平均环氧当量为5.395当量/kg
环氧树脂2：液态双酚F二缩水甘油醚，平均环氧当量为5.95当量/kg
胺1：4，4’-二氨基-3，3’-二甲基二环己基甲烷
胺2：环己基胺
胺3：4，7，10-三氧-1，13-十三烷二胺(商品名Q19262)
异氰酸酯1：甲苯二异氰酸酯uretidone二聚物(商品名为DesmodurTT，NCO含量为-24重量％)
异氰酸酯2：异佛尔酮二异氰酸酯二聚物(商品名为Vestanate，NCO含量为-17重量％)实施例1(对比例)
100g环氧树脂1同6g胺1混合。混合物是完全手混合的，混合24小时后混合物是澄清的粘稠液体，显示出良好的粘性，并表现出随时间的稳定性。实施例2
100g环氧树脂1同6g胺1手混合。然后，加入17.5g异氰酸酯1粉末，且混合物通过三辊磨，持续两个周期。静置24小时后，获得白色粘稠液体，显示出良好的粘性和高储存稳定性。实施例3
100g环氧树脂1、6g胺1和14g异氰酸酯1粉末根据实施例2的记载进行加工。产物是粘稠液体，显示出良好的粘性和高储存稳定性。实施例4
100g环氧树脂1、6g胺1和10.5g异氰酸酯1粉末根据实施例2的记载进行加工。产物是粘稠液体，显示出良好的粘性和高储存稳定性。实施例5(对比例)
100g环氧树脂1和8g胺1的共混物完全混合，并静置24小时。所得的产物是高粘稠的澄清液体，其表现出较差的粘性。实施例6
100g环氧树脂1、8g胺1和23.4g异氰酸酯1粉末的共混物手混合，并通过三辊磨，持续两个周期。所得的产物是白色、高粘稠液体，其表现出没有粘性。
由实施例1～6中获得的凝胶化产物，使用铝板(L165)，通过在120℃下固化30分钟来制备搭接剪切试样(一式三份)。结果概括在表1中。
表1
| 实施例 | 搭接剪切强度(N/mm2) |
| 1 | 0.02 |
| 2 | 12.07 |
| 3 | 10.97 |
| 4 | 10.48 |
| 5 | 0.64 |
| 6 | 16.55 |
该表的数据显示了含有潜异氰酸酯交联剂的试样表征出比对比例1和5高很多的搭接剪切强度。实施例7-14
制备环氧树脂1、胺1和异氰酸酯2的共混物，按实施例2的记载进行加工。异氰酸酯2以颗粒的形式加入，通过咖啡研磨机(白色粉末，形状不规则，平均粒径接近100μm)。得到的产物是乳白色的粘稠糊状物。
由实施例7～14中获得的凝胶化产物，使用铝板(L165)，通过分别在60℃和80℃下固化16小时来制备搭接剪切试样(一式三份)。结果概括在表2中。
表2：
实施例15(对比例)
| 实施例 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 14 |
| 环氧树脂1[g]HY 2954[g]异氰酸酯2[g] | 10068.93 | 100613.46 | 100617.93 | 100622.40 | 100811.93 | 100817.93 | 100823.93 | 100823.93 |
| 搭接剪切强度[N/mm2]16h/60℃16h/80℃ | 3.556.47 | 2.746.17 | 1.746.01 | 0.421.95 | 3.673.32 | 4.025.23 | 4.814.99 | 4.975.29 |
制备100g环氧树脂1和5.87g胺3的混合物，按实施例1的记载进行加工。所得的产物是澄清的粘稠液体。用该组合物制备搭接剪切试样，并分别在60℃和80℃下固化，得不到仍然是湿和粘性的试样。实施例16：
制备100g环氧树脂1、5.87g胺3和异氰酸酯1粉末的混合物，按实施例2的记载进行加工。所得的产物是白色粘稠液体。
由固化该组合物获得的试样的搭接剪切数据列在表3中。
表3
| 固化条件 | 搭接剪切强度(N/mm2) |
| 4h/60℃16h/60℃1h/80℃2h/80℃3h/80℃4h/80℃16h/80℃ | 0.0370.7281.641.572.903.324.41 |
将实施例10的组合物在不同温度下固化30分钟，随后获得的搭接剪切值是：
表4
实施例17(对比例)
| 固化温度 | 搭接剪切强度(N/mm2) |
| 60℃80℃100℃120℃140℃160℃180℃ | -1.102.282.672.852.933.39 |
制备50g环氧树脂1、50g环氧树脂2和6.73g胺1的混合物，按实施例1的记载进行加工。所得的产物是澄清的粘稠液体。用分别在60℃和80℃下固化16小时的试样不能测得搭接剪切值，得不到仍然是湿和粘性的试样。实施例18
制备50g环氧树脂1、50g环氧树脂2、6.73g胺1和19.7g异氰酸酯1粉末的混合物，按实施例2的记载进行加工。所得的产物是白色的粘稠液体。固化产物的搭接剪切数据概括在表5中。
表5
实施例19-27
| 固化条件 | 搭接剪切强度(N/mm2) | 固化条件 | 搭接剪切强度(N/mm2) |
| 1h/60℃2h/60℃3h/60℃4h/60℃16h/60℃1h/80℃2h/80℃3h/80℃4h/80℃16h/80℃ | 5.187.648.128.8611.1910.1312.3112.5812.9713.59 | 30min/60℃30min/80℃30min/100℃30min/120℃30min/140℃30min/160℃30min/180℃ | 1.579.5910.8510.598.295.822.82 |
制备环氧树脂1、胺1和异氰酸酯1的共混物，按实施例2的记载进行加工。所得的产物是固体：19是澄清的，而20-27是白色的。试样在60℃和80℃下固化16小时，随后获得的搭接剪切数据为：
表6
| 实施例 | 19 | 20 | 21 | 22 | 23 | 24 | 25 | 26 | 27 |
| 环氧树脂1[g]胺1[g]胺2[g]异氰酸酯1[g] | 10010.660 | 10010.665.2 | 10010.6610.4 | 10010.6615.6 | 10010.6620.8 | 10010.6625.4 | 10010.6631.2 | 10010.6641.6 | 10010.6652.0 |
| 搭接剪切强度[N/mm2]1h/60℃1h/80℃1h/120℃ | 0.490.290.55 | 0.570.551.33 | 0.620.631.19 | -- | 0.500.802.60 | -- | 0.411.273.27 | 0.240.942.31 | 0.601.181.57 |
Claims (10)
1.一种组合物，包括：
(A)每分子含有至少两个环氧基团的环氧化物，
(B)每分子含有至少两个羟基的多元醇或每分子含有至少两个氨基氢原子的伯胺或仲胺，和
(C)含有至少两个异氰酸酯基团的固体化合物。
2.根据权利要求1的组合物，其中组分A是二缩水甘油醚或二缩水甘油酯。
3.根据权利要求1的组合物，其中组分A是双酚A或双酚F的二缩水甘油醚。
4.根据权利要求1的组合物，其中组分B是脂族或脂环族胺。
5.根据权利要求1的组合物，其中组分B是环己基胺、4，4’-二氨基二环己基甲烷、4，4’-二氨基-3，3’-二甲基二环己基甲烷、2，2-二(4-氨基环己基)丙烷或2，2-二(4-氨基-3-甲基环己基)丙烷。
6.根据权利要求1的组合物，其中组分C是二异氰酸酯单体、二异氰酸酯二聚物、二异氰酸酯三聚物或二异氰酸酯和脂族二醇的固体反应产物。
7.根据权利要求6的组合物，其中二异氰酸酯选自2，4-甲苯二异氰酸酯、2，6-甲苯二异氰酸酯、2，3-甲苯二异氰酸酯、3，4-甲苯二异氰酸酯、4，4’-二苯基甲烷二异氰酸酯、2，2’-二苯基甲烷二异氰酸酯、对亚苯基二异氰酸酯、异佛尔酮二异氰酸酯和4，4’-亚甲基-二(环己基异氰酸酯)。
8.一种制备凝胶、糊状物或粉末形式的单组分热固性树脂组合物的方法，包括混合根据权利要求1的组分(A)、(B)和(C)，在＜50℃的温度下反应混合物，直到混合物的粘度高出初始粘度至少10％。
9.由根据权利要求8的方法获得的单组分热固性树脂组合物作为防护涂料或粘合剂的用途。
10.通过在60～180℃下固化根据权利要求8的方法获得的单组分热固性树脂组合物所获得的交联产物。
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|---|---|---|---|
| EP00810087 | 2000-01-31 | ||
| EP00810087.7 | 2000-01-31 |
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| EP (1) | EP1252218B1 (zh) |
| JP (1) | JP5035785B2 (zh) |
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| CA (1) | CA2399084C (zh) |
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| ES (1) | ES2267720T3 (zh) |
| HK (1) | HK1048824A1 (zh) |
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| CN104774428A (zh) * | 2014-01-14 | 2015-07-15 | 展麒绿能股份有限公司 | 轻力强材及其制造方法 |
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| CN108342175A (zh) * | 2018-02-07 | 2018-07-31 | 滕凤琴 | 一种环氧树脂胶粘剂及其制备方法 |
| CN113322038A (zh) * | 2021-06-28 | 2021-08-31 | 中国兵器工业第五九研究所 | 一种常温固化改性环氧树脂胶粘剂及其制作方法 |
| CN114230749A (zh) * | 2021-11-29 | 2022-03-25 | 西安交通大学 | 一种可快速自修复环氧树脂固化物、制备方法及应用 |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI279408B (en) * | 2000-01-31 | 2007-04-21 | Vantico Ag | Epoxy resin composition |
| JP4596815B2 (ja) * | 2004-04-26 | 2010-12-15 | パイロットインキ株式会社 | 可逆熱変色性マイクロカプセル型顔料及びその製造方法 |
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Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4036906A (en) * | 1969-12-30 | 1977-07-19 | The Goodyear Tire & Rubber Company | Cured polyurethane compositions containing epoxy resins |
| US4067843A (en) * | 1976-06-07 | 1978-01-10 | Hooker Chemicals & Plastics Corporation | Granular phenolic urethane molding compounds |
| US4486557A (en) * | 1981-11-11 | 1984-12-04 | Atlantic Richfield Company | Organic polyisocyanate-liquid aromatic epoxide-lignin adhesive binder compositions |
| DE3230757A1 (de) * | 1982-08-18 | 1984-02-23 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von stabilisierten polyisocyanaten, stabilisierte polyisocyanate retardierter reaktivitaet und ihre verwendung zur polyurethanherstellung |
| JPS5962620A (ja) * | 1982-10-04 | 1984-04-10 | Sumitomo Bakelite Co Ltd | エポキシ樹脂の硬化方法 |
| DE3418429A1 (de) * | 1984-05-18 | 1985-11-21 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von festen polyisocyanaten retardierter reaktivitaet, polymerumhuellte, feinteilige polyisocyanate und ihre verwendung |
| DE3429149A1 (de) * | 1984-08-08 | 1986-02-20 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von stabilisierten polyaminen, stabilisierte polyamine retardierter reaktivitaet und ihre verwendung zur polyurethanherstellung |
| JPS61235422A (ja) * | 1985-04-10 | 1986-10-20 | Idemitsu Petrochem Co Ltd | エポキシ樹脂用硬化剤 |
| JPS62138520A (ja) * | 1985-12-13 | 1987-06-22 | Idemitsu Petrochem Co Ltd | 液状重合体組成物 |
| JPH0694496B2 (ja) * | 1986-02-21 | 1994-11-24 | 旭電化工業株式会社 | 硬化性組成物 |
| JPS62270658A (ja) * | 1986-03-11 | 1987-11-25 | パ−マ−・インタナシヨナル・インコ−ポレイテツド | 耐摩耗性重合体組成物及び被覆 |
| US4737565A (en) * | 1987-04-09 | 1988-04-12 | Ashland Oil, Inc. | Single component, latent curing epoxy resin composition |
| JPH066621B2 (ja) * | 1990-04-16 | 1994-01-26 | 富士化成工業株式会社 | 一成分系加熱硬化性エポキシド組成物 |
| JPH0488011A (ja) * | 1990-07-31 | 1992-03-19 | Sumitomo Chem Co Ltd | エポキシ樹脂組成物 |
| EP0479445B1 (en) * | 1990-10-03 | 1998-03-11 | The Dow Chemical Company | Hydroxyl functionalized polyetheramines as barrier packaging for oxygen-sensitive materials |
| DE4130329A1 (de) * | 1991-09-12 | 1993-03-18 | Bayer Ag | Waermehaertbare reaktionsharzgemische, ein verfahren zu ihrer herstellung und die verwendung zur herstellung von press-massen und formkoerpern |
| US5227414A (en) * | 1992-04-29 | 1993-07-13 | Tennant Company | Aqueous urethane-epoxy coating composition |
| WO1994004624A1 (de) * | 1992-08-17 | 1994-03-03 | Thomas Paul Abend | Bei raumtemperatur vernetzbare massen, verfahren zu ihrer herstellung und ihre verwendung |
| US5844047A (en) * | 1993-07-16 | 1998-12-01 | Ciba Specialty Chemicals Corporation | Single component, heat curing compositions which are stable when stored at room temperature and which comprise polymers containing anhydride groups and powdered crosslinking agents, and their method of manufacture and use |
| GB2280441A (en) * | 1993-07-28 | 1995-02-01 | Peter Drummond Boys White | Gelled reactive resin compositions |
| DE4327570A1 (de) * | 1993-08-17 | 1995-04-20 | Bayer Ag | Rieselfähige Preßmassen, Verfahren zu deren Herstellung und ihre Verwendung |
| CA2115533C (en) * | 1994-02-11 | 2002-06-18 | Hiroshi Uchida | Urethane modified epoxy resin compositions |
| DE4421816A1 (de) * | 1994-06-22 | 1996-01-04 | Bayer Ag | Mischblockierte Isocyanatpräpolymere, ein Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung flexibilisierter Epoxidharz-Systeme |
| JPH08325349A (ja) * | 1995-06-01 | 1996-12-10 | Nitto Denko Corp | エポキシ樹脂組成物およびそれを用いた補強接着シート |
| GB9523649D0 (en) | 1995-11-18 | 1996-01-17 | White Peter D B | Hot melt reactive resin compositions |
| JP3881381B2 (ja) | 1995-11-18 | 2007-02-14 | ヴァンティコ アーゲー | 粉末化可能な反応性樹脂組成物 |
| JPH09157354A (ja) * | 1995-12-07 | 1997-06-17 | Matsushita Electric Works Ltd | 封止用エポキシ樹脂組成物 |
| DE19628409A1 (de) * | 1996-07-15 | 1998-01-22 | Hoechst Ag | Amin-modifizierte Epoxidharz-Zusammensetzung |
| PT922720E (pt) * | 1997-12-11 | 2002-01-30 | Bayer Ag | Processo para a preparacao e utilizacao de camadas ou pos reactivos latentes estaveis a armazenagem de poliisocianatos solidos desactivados superficialmente e polimeros de dispersao com grupos funcionais |
| TWI279408B (en) * | 2000-01-31 | 2007-04-21 | Vantico Ag | Epoxy resin composition |
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2000
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103387789A (zh) * | 2013-07-08 | 2013-11-13 | 吴江市物华五金制品有限公司 | 洗衣机用抗菌粉末涂料及其制备方法 |
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| CN104774428A (zh) * | 2014-01-14 | 2015-07-15 | 展麒绿能股份有限公司 | 轻力强材及其制造方法 |
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| CN107691448A (zh) * | 2017-10-18 | 2018-02-16 | 万华化学集团股份有限公司 | 一种环氧大豆油基防霉剂及其制备方法和应用、环氧美缝剂 |
| CN107691448B (zh) * | 2017-10-18 | 2020-07-28 | 万华化学集团股份有限公司 | 一种环氧大豆油基防霉剂及其制备方法和应用、环氧美缝剂 |
| CN108342175A (zh) * | 2018-02-07 | 2018-07-31 | 滕凤琴 | 一种环氧树脂胶粘剂及其制备方法 |
| CN113322038A (zh) * | 2021-06-28 | 2021-08-31 | 中国兵器工业第五九研究所 | 一种常温固化改性环氧树脂胶粘剂及其制作方法 |
| CN114230749A (zh) * | 2021-11-29 | 2022-03-25 | 西安交通大学 | 一种可快速自修复环氧树脂固化物、制备方法及应用 |
Also Published As
| Publication number | Publication date |
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| BR0107962A (pt) | 2002-10-29 |
| ATE340813T1 (de) | 2006-10-15 |
| ES2267720T3 (es) | 2007-03-16 |
| TWI279408B (en) | 2007-04-21 |
| EP1252218A1 (en) | 2002-10-30 |
| EP1252218B1 (en) | 2006-09-27 |
| US20060247333A1 (en) | 2006-11-02 |
| KR20020063623A (ko) | 2002-08-03 |
| US7141629B2 (en) | 2006-11-28 |
| US7507778B2 (en) | 2009-03-24 |
| US20030149194A1 (en) | 2003-08-07 |
| CA2399084C (en) | 2009-11-24 |
| HK1048824A1 (zh) | 2003-04-17 |
| CA2399084A1 (en) | 2001-08-09 |
| JP2003522237A (ja) | 2003-07-22 |
| JP5035785B2 (ja) | 2012-09-26 |
| AU3733301A (en) | 2001-08-14 |
| DE60123385D1 (de) | 2006-11-09 |
| CN1255449C (zh) | 2006-05-10 |
| WO2001057110A1 (en) | 2001-08-09 |
| DE60123385T2 (de) | 2007-08-23 |
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