CN114746471B - 用于环氧铸塑树脂的硬化剂 - Google Patents
用于环氧铸塑树脂的硬化剂 Download PDFInfo
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- CN114746471B CN114746471B CN202080081517.1A CN202080081517A CN114746471B CN 114746471 B CN114746471 B CN 114746471B CN 202080081517 A CN202080081517 A CN 202080081517A CN 114746471 B CN114746471 B CN 114746471B
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- Prior art keywords
- hardener
- amine
- epoxy resin
- diepoxide
- bis
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- 229920005989 resin Polymers 0.000 title claims abstract description 52
- 239000011347 resin Substances 0.000 title claims abstract description 52
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- 239000004593 Epoxy Substances 0.000 title description 8
- 239000000203 mixture Substances 0.000 claims abstract description 70
- 150000001412 amines Chemical class 0.000 claims abstract description 60
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 57
- 239000003822 epoxy resin Substances 0.000 claims abstract description 54
- 229920000768 polyamine Polymers 0.000 claims abstract description 29
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- -1 1, 2-propylene Chemical group 0.000 claims description 33
- 229920001451 polypropylene glycol Polymers 0.000 claims description 19
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 16
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 claims description 12
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- XUCHXOAWJMEFLF-UHFFFAOYSA-N bisphenol F diglycidyl ether Chemical compound C1OC1COC(C=C1)=CC=C1CC(C=C1)=CC=C1OCC1CO1 XUCHXOAWJMEFLF-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
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- DZIHTWJGPDVSGE-UHFFFAOYSA-N 4-[(4-aminocyclohexyl)methyl]cyclohexan-1-amine Chemical compound C1CC(N)CCC1CC1CCC(N)CC1 DZIHTWJGPDVSGE-UHFFFAOYSA-N 0.000 claims description 3
- OXIKYYJDTWKERT-UHFFFAOYSA-N [4-(aminomethyl)cyclohexyl]methanamine Chemical compound NCC1CCC(CN)CC1 OXIKYYJDTWKERT-UHFFFAOYSA-N 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 125000006732 (C1-C15) alkyl group Chemical group 0.000 claims description 2
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- 239000004615 ingredient Substances 0.000 description 9
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 9
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- 239000001257 hydrogen Substances 0.000 description 8
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- 239000002023 wood Substances 0.000 description 6
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
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- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 5
- HHRACYLRBOUBKM-UHFFFAOYSA-N 2-[(4-tert-butylphenoxy)methyl]oxirane Chemical compound C1=CC(C(C)(C)C)=CC=C1OCC1OC1 HHRACYLRBOUBKM-UHFFFAOYSA-N 0.000 description 4
- WTYYGFLRBWMFRY-UHFFFAOYSA-N 2-[6-(oxiran-2-ylmethoxy)hexoxymethyl]oxirane Chemical compound C1OC1COCCCCCCOCC1CO1 WTYYGFLRBWMFRY-UHFFFAOYSA-N 0.000 description 4
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- 239000000126 substance Substances 0.000 description 4
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Classifications
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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
- 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
- C08G59/50—Amines
- C08G59/504—Amines containing an atom other than nitrogen belonging to the amine group, carbon and hydrogen
-
- 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
- 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
- C08G59/50—Amines
- C08G59/56—Amines together with other curing agents
-
- 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
- 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
- C08G59/182—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 using pre-adducts of epoxy compounds with curing agents
- C08G59/184—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 using pre-adducts of epoxy compounds with curing agents with amines
-
- 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
- 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
- C08G59/50—Amines
- C08G59/5033—Amines aromatic
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
-
- 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
- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
- C08G2650/50—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing nitrogen, e.g. polyetheramines or Jeffamines(r)
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
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Abstract
本发明的主题是一种用于环氧树脂的硬化剂,其包含至少一种式(I)的胺,和至少一种聚氧亚烷基多胺和二环氧化物的胺官能化加合物。本发明的硬化剂能够获得高透明度的透明的环氧树脂组合物,其不含有毒稀释剂例如壬基酚,在固化时表现出低的发热,但是仍然能够快速和可靠地固化,并且具有高的抗黄变稳定性。这样的环氧树脂组合物特别适于作为铸塑树脂来制造具有玻璃状外观的透明制品。
Description
技术领域
用于环氧树脂的硬化剂及其在形成完全透明的制品的铸塑树脂中的用途。
现有技术
在环境温度依靠胺硬化剂固化的环氧树脂组合物被广泛用作铸塑树脂、涂料或者粘结剂。铸塑树脂应用的一个例子是制造透明的、硬的和坚韧的树脂制品,其具有玻璃状外观,并且可以用于功能化和/或装饰目的。这样的铸塑树脂允许引入成形材料例如木片或者石头,并且使得它们以有光泽的和高美观方式呈现。对于这样的应用来说,铸塑树脂应当可以例如5-50mm的厚层施用,并且铸塑树脂在固化后具有优选高于55℃的高玻璃化转变温度(Tg),和高透明度,即,是完全透明的,没有任何雾浊、浑浊或者其它种类的可见不均匀性。这是不易实现的,因为许多的胺硬化剂倾向于引起雾浊或者浑浊外观。此外,环氧固化反应是高放热的,和所以新鲜混合的树脂当以厚层施用时倾向于过热,这会导致变色和/或气泡。为了实现美学良好的结果,需要硬化剂,其在与环氧树脂反应时仅仅产生了适度的热峰,并且仍然能够快速和可靠地固化,而不在固化的树脂或者在它的表面上形成任何雾浊。最后,固化的透明制品应当具有高的抗黄变稳定性,以使得在曝露于光时不失去它的初始外观。
用于这样的用途的环氧树脂组合物是市场上已知的。它们通常包含高含量的烷基酚例如壬基酚。烷基酚是稀释剂,并且赋予树脂高透明度和低发热,同时仍然能够快速和可靠地固化,但是它们对于人类和环境来说是有毒化合物,这使得它们的处置需要特殊的安全措施。此外,烷基酚和其它类型的稀释剂在固化的树脂中保持为未反应,并且会通过迁移、萃取或者蒸发而从其中释放,这加剧了它们的毒性。另外,它们还会对于固化的树脂具有不期望的软化效应,这降低了Tg。
因此需要用于环氧铸塑树脂的新硬化剂,其不含有毒稀释剂例如壬基酚等,并且能够在低发热、低反应焓、快速固化和高透明度以及高Tg方面产生类似的性能。
1,2-丙二胺和甲苯基缩水甘油基醚的加合物从US 9796661中是已知的。它可用于单独地或者与非加成的胺组合来配制低排放环氧地板。
发明内容
本发明的任务是提供一种用于环氧树脂的硬化剂,其没有有毒稀释剂,并且特别适于铸塑树脂,这能够生产具有高透明度、高Tg和高抗黄变稳定性的透明铸塑制品。
这个任务是通过根据权利要求1的硬化剂来实现的,其包含至少一种式(I)的胺,和至少一种聚氧亚烷基多胺和二环氧化物的胺官能化加合物。
式(I)的胺是伯二胺例如1,2-丙二胺和芳族单环氧化物例如甲苯基缩水甘油基醚的单加合物。与所述聚氧亚烷基多胺加合物相组合,本发明的硬化剂令人惊讶地能够铸塑具有高Tg、完全无色透明(a fully water clear transparency)和光滑不粘表面的期望的制品,具有低发热以及快速和可靠的固化,无需添加有毒稀释剂例如壬基酚。所述硬化剂具有低粘度,以便易于与环氧树脂混合和易于通过以一个或者几个厚层(例如5-50mm的层)浇注来施用所述混合树脂。此外,所述固化的制品在曝露于光时表现出非常好的耐UV性和高的抗黄变稳定性。
本发明的硬化剂产生这样的环氧树脂组合物,其特别适于作为铸塑树脂,来生产具有高透明度和玻璃状外观以及高抗黄变稳定性的透明制品,向其中可以引入成形材料,例如木片或者石头,干花,人工珍珠或者装饰片。添加染料使得玻璃状树脂制品具有透明的有色外观。由于不存在有毒稀释剂例如壬基酚,这些制品在使用中是高度安全的。
本发明其它方面在其它独立权利要求中描述。本发明优选的方面描述在从属权利要求中。
发明详述
本发明的一个主题是一种用于环氧树脂的硬化剂,其包含:
–至少一种式(I)的胺,
其中:
A是二价C2-C15亚烷基,亚环烷基或者芳基亚烷基,和
R是C1-C15烷基,其非必要地含有不饱和键,和
–至少一种聚氧亚烷基多胺和二环氧化物的胺官能化加合物。
以“聚(多)”开始的物质名称例如多胺或者聚环氧化物指的是每个分子带有两个或者更多个各自的官能团的物质。
术语“伯胺基”指的是这样的胺基团,其连接到仅仅一个有机结构部分上和带有两个氢;术语“仲胺基”指的是这样的胺基团,其连接到两个有机结构部分上,其还可以是环整体的一部分,并且带有一个氢;和术语“叔胺基”指的是这样的胺基团,其连接到三个有机结构部分上,其中的两个或三个也可以是一个或多个环的一部分,并且不带有氢。
术语“胺氢”指的是伯胺基和仲胺基的氢。
术语“胺氢当量”指的是胺或者含胺组合物的质量,其包含一摩尔当量的胺氢。
术语“分子量”指的是分子的摩尔质量(以g/mol给出)。术语“平均分子量”指的是低聚物或者聚合物分子或者分子结构部分的多分散混合物的数均分子量Mn。它通常是通过凝胶渗透色谱法(GPC),相对于聚苯乙烯标准物测定的。
在本文献中,术语“室温”指的是23℃温度。
术语“有效期”指的是这样的时间期间,在此期间多组分组合物可以在所述组分混合后施用,而无缺陷。
优选A是二价C2-C10亚烷基,亚环烷基或者芳基亚烷基。
更优选A选自1,2-亚乙基,1,2-亚丙基,2-甲基-1,5-亚戊基,1,6-亚己基,2,2(4),4-三甲基-1,6-六亚甲基,1,3-亚苯基-双(亚甲基),1,4-亚苯基-双(亚甲基),1,2-亚环己基,1,3-亚环己基,1,4-亚环己基,(1,5,5-三甲基环己烷-1-基)甲烷-1,3,4(2)-甲基-1,3-亚环己基,1,3-亚环己基-双(亚甲基)和1,4-亚环己基-双(亚甲基)。
优选其是1,2-亚乙基,1,2-亚丙基,2-甲基-1,5-亚戊基,1,6-亚己基或者1,2-亚环己基。
特别优选的是1,2-亚丙基。这样的式(I)的胺能够获得具有特别高的透明度和抗黄变稳定性的制品。
优选R是甲基,叔丁基,壬基,十二烷基或者8,11-十五碳二烯基。这样的式(I)的胺特别易于制造。
优选R没有不饱和键。这样的式(I)的胺是特别抗黄变稳定的。
特别优选R是甲基或者叔丁基。
最优选R是甲基,其优选处于邻位。这样的式(I)的胺易于制造,能够特别快速和可靠的固化和具有高的抗黄变稳定性。
最优选A是1,2-亚丙基和R是邻甲基。
式(I)的胺优选是通过式H2N-A-NH2的伯二胺与式的缩水甘油基醚反应来制备,其中A和R具有已经给出的含义。
用于这种制备的特别合适的伯二胺是1,2-乙二胺,1,2-丙二胺,1,3-丙二胺,1,4-丁二胺,1,3-丁二胺,2-甲基-1,2-丙二胺,1,3-戊二胺,1,5-戊二胺,2,2-二甲基-1,3-丙二胺,1,6-己二胺,1,5-二氨基-2-甲基戊烷,1,7-庚二胺,1,8-辛二胺,2,5-二甲基-1,6-己二胺,1,9-壬二胺,2,2(4),4-三甲基-1,6-己二胺,1,10-癸二胺,1,2-环己二胺,1,3-环己二胺,1,4-环己二胺,1-氨基-3-氨基甲基-3,5,5-三甲基环己烷,4(2)-甲基-1,3-环己二胺,1,3-双(氨基甲基)环己烷,1,4-双(氨基甲基)环己烷,2,5(2,6)-双(氨基甲基)双环[2.2.1]庚烷,1,3-双(氨基甲基)苯(benzol)或者1,4-双(氨基甲基)苯(benzol)。
其优选是1,2-乙二胺,1,2-丙二胺,1,6-己二胺,1,5-二氨基-2-甲基戊烷或者1,2-环己二胺。特别优选地是1,2-丙二胺。
用于这种制备的特别合适的缩水甘油基醚是甲苯基缩水甘油基醚,叔丁基苯基缩水甘油基醚,4-壬基苯基缩水甘油基醚,4-十二烷基苯基缩水甘油基醚或者腰果酚缩水甘油基醚,其包含3-(8,11-十五碳二烯基)酚的缩水甘油基醚作为主要成分。
其优选是甲苯基缩水甘油基醚或者叔丁基苯基缩水甘油基醚。
最优选的是甲苯基缩水甘油基醚,特别是邻甲苯基缩水甘油基醚。
优选使用市售品质的甲苯基缩水甘油基醚,例如DY-K(来自于Huntsman),HeloxyTM Modifier 62(来自于Momentive)或者/>GE-10(来自于CVC)。
所述伯二胺和缩水甘油基醚优选在40-120℃,优选50-110℃的温度反应。
优选的比率是0.8-5mol伯二胺,基于缩水甘油基醚的每摩尔的环氧基团。如果伯二胺是以超化学计量使用的,则优选通过真空蒸馏来从产物中除去未反应的伯二胺。
一种特别优选的式(I)的胺是通过1,2-丙二胺和甲苯基缩水甘油基醚以2/1-4/1摩尔比反应,随后通过蒸馏方法,特别是薄膜或者短程蒸馏方法从产物中除去未反应的1,2-丙二胺来制备。
这样的制备的产物可以除了式(I)的胺之外,还包括一些更高级加成的化合物,特别下式的双加合物:其中A和R具有已经给出的含义。
所述用于环氧树脂的硬化剂进一步包含至少一种聚氧亚烷基多胺和二环氧化物的胺官能化加合物。
所述氧亚烷基基团优选是选自氧亚乙基基团,氧基-1,2-亚丙基基团,氧基-1,3-亚丙基基团,氧基-1,4-亚丁基基团,氧基-1,2-亚丁基基团及其混合物,非必要地与起始分子例如三羟甲基丙烷或者甘油相组合。
所述聚氧亚烷基多胺优选是选自4,7,10-三氧杂十三烷-1,13-二胺,平均分子量Mn为170-500g/mol的α,ω-聚氧亚丙基二胺,例如D-230或者/>D-400(来自于Huntsman),和平均分子量Mn为300-500g/mol的聚氧亚丙基三胺,优选来自于三羟甲基丙烷的丙氧基化,和随后OH端基胺化的聚氧亚丙基三胺,例如/>T-403(来自于Huntsman)。
特别优选的是平均分子量Mn为170-500g/mol的聚氧亚丙基二胺或者聚氧亚丙基三胺或者其混合物例如D-230,/>D-400或者/>T-403(来自于Huntsman)与二环氧化物的胺官能化加合物。
最优选的是平均分子量Mn为300-500g/mol的聚氧亚丙基三胺,优选T-403(来自于Huntsman)与二环氧化物的胺官能化加合物。
所述加合物的二环氧化物优选是二缩水甘油基醚,优选双酚A二缩水甘油基醚,双酚F二缩水甘油基醚,双酚A/F二缩水甘油基醚,间苯二酚二缩水甘油基醚,4,4'-二羟基联苯基二缩水甘油基醚,4,4'-二羟基二苯甲酮二缩水甘油基醚,水合双酚A、F或者A/F二缩水甘油基醚,1,4-丁二醇二缩水甘油基醚,新戊二醇二缩水甘油基醚,1,6-己二醇二缩水甘油基醚,二羟甲基环己烷二缩水甘油基醚,二丙二醇二缩水甘油基醚,三丙二醇二缩水甘油基醚或者更高级的聚丙二醇二缩水甘油基醚。
最优选,所述加合物的二环氧化物是双酚A、双酚F或者双酚A/F二缩水甘油基醚,特别是双酚A二缩水甘油基醚。这样的加合物使得固化的产物具有特别高的硬度和耐受性。
优选的是工业级(technical grade)的这样的二环氧化物,因为它例如市售自Dow,Huntsman或者Hexion。
最优选的是至少一种平均分子量Mn为300-500g/mol的聚氧亚丙基三胺与双酚A二缩水甘油基醚或者双酚F二缩水甘油基醚或者双酚A/F二缩水甘油基醚,特别是双酚A二缩水甘油基醚的胺官能化加合物。
所述胺官能化加合物优选是通过聚氧亚烷基多胺和二环氧化物以聚氧亚烷基多胺分子:二环氧化物每摩尔环氧基团的摩尔比为1.05-5,优选1.1-3,更优选1.1-2反应来制备的。
在聚氧亚烷基三胺的情况中,NH2-基团:二环氧化物的每摩尔环氧基团的摩尔比优选是3.1-15,优选3.3-9,更优选3.3-6。
这样的加合物包含胺官能化加合物分子以及一部分未反应的聚氧亚烷基多胺的混合物。所述未反应的聚氧亚烷基多胺(其在加合物形成过程中存在)被认为是加合物的一部分。
加合物优选在40-150℃,优选50-120℃的温度制造。
所述优选的加合物使得硬化剂具有特别快的固化和低发热和良好的施用性能。
本发明的硬化剂优选包含式(I)的胺,和至少一种聚氧亚烷基多胺和二环氧化物以重量比0.2/1-10/1,优选0.4/1-5/1的胺官能化加合物。
本发明的硬化剂优选包含至少一种另外的胺,优选至少一种具有至少3个胺氢的多胺。
合适的另外的胺是具有一个伯胺基和至少一个仲胺基的脂族、脂环族或者芳基脂族多胺,特别是N-苄基-1,2-乙二胺,N-苄基-1,2-丙二胺,N-苄基-2-甲基-1,5-戊二胺,N-苄基-1,3-双(氨基甲基)苯,N-(2-乙基己基)-1,3-双(氨基甲基)苯,2-氨基乙基哌嗪,3-二甲基氨基丙基胺(DMAPA),3-(3-(二甲基氨基)丙基氨基)丙基胺(DMAPAPA),N-苄基二亚乙基三胺,N-苄基三亚乙基四胺,N”-苄基-N,N'-双(3-氨基丙基)亚乙基二胺,或者这些多胺与单环氧化物或者二环氧化物的加合物。
合适的另外的胺还是具有至少两个伯胺基的脂族、脂环族或者芳基脂族多胺,特别是2,2-二甲基-1,3-丙二胺,1,3-戊二胺(DAMP),1,5-戊二胺,1,5-二氨基-2-甲基戊烷(MPMD),2-丁基-2-乙基-1,5-戊二胺(C11-新二胺),1,6-己二胺,2,5-二甲基-1,6-己二胺,2,2(4),4-三甲基-1,6-己二胺(TMD),1,7-庚二胺,1,8-辛二胺,1,9-壬二胺,1,10-癸二胺,1,11-十一烷二胺,1,12-十二烷二胺,1,2-,1,3-或者1,4-二氨基环己烷,1,3-双(氨基甲基)环己烷,1,4-双(氨基甲基)环己烷,双(4-氨基环己基)甲烷,双(4-氨基-3-甲基环己基)甲烷,双(4-氨基-3-乙基环己基)甲烷,双(4-氨基-3,5-二甲基环己基)甲烷,双(4-氨基-3-乙基-5-甲基环己基)甲烷,1-氨基-3-氨基甲基-3,5,5-三甲基环己烷(异佛尔酮二胺或者IPDA),2(4)-甲基-1,3-二氨基环己烷,2,5(2,6)-双(氨基甲基)双环[2.2.1]庚烷(NBDA),3(4),8(9)-双(氨基甲基)三环[5.2.1.02,6]癸烷,1,4-二氨基-2,2,6-三甲基环己烷(TMCDA),1,8-甲二胺,3,9-双(3-氨基丙基)-2,4,8,10-四氧杂螺[5.5]十一烷,1,3-双(氨基甲基)苯(MXDA),1,4-双(氨基甲基)苯,双(2-氨基乙基)醚,3,6-二氧杂辛烷-1,8-二胺,4,7-二氧杂癸烷-1,10-二胺,4,7-二氧杂癸烷-2,9-二胺,4,9-二氧杂十二烷-1,12-二胺,5,8-二氧杂十二烷-3,10-二胺,4,7,10-三氧杂十三烷-1,13-二胺或者这些二胺的更高级低聚物,双(3-氨基丙基)聚四氢呋喃或者其它聚四氢呋喃二胺,聚氧亚烷基二-或者-三胺,特别是D-230,/>D-400,/>D-2000,/>EDR-104,/>EDR-148,/>EDR-176,/>T-403,T-3000或者/>T-5000(全部来自于Huntsman),双(6-氨基己基)胺(BHMT),二亚乙基三胺(DETA),三亚乙基四胺(TETA),四亚乙基五胺(TEPA),五亚乙基六胺(PEHA)或者其更高级的同系物,二亚丙基三胺(DPTA),N-(2-氨基乙基)-1,3-丙烷二胺(N3-胺),N,N'-双(3-氨基丙基)亚乙基二胺(N4-胺),N,N'-双(3-氨基丙基)-1,4-二氨基丁烷,N5-(3-氨基丙基)-2-甲基-1,5-戊二胺,N3-(3-氨基戊基)-1,3-戊二胺,N5-(3-氨基-1-乙基丙基)-2-甲基-1,5-戊二胺,N,N'-双(3-氨基-1-乙基丙基)-2-甲基-1,5-戊二胺,或者这些多胺与单环氧化物或者二环氧化物的加合物。
所述另外的胺优选是选自N-苄基-1,2-乙二胺,N-苄基-1,2-丙二胺,TMD,1,2-,1,3-或者1,4-二氨基环己烷,1,3-双(氨基甲基)环己烷,1,4-双(氨基甲基)环己烷,双(4-氨基环己基)甲烷,IPDA,2(4)-甲基-1,3-二氨基环己烷,MXDA,平均分子量Mn为170-500g/mol的聚氧亚丙基二胺,平均分子量Mn为300-500g/mol的聚氧亚丙基三胺,TETA,TEPA,PEHA,N4-胺及其混合物。
一种特别优选的另外的胺是平均分子量Mn为170-500g/mol的聚氧亚丙基二胺,例如D-230或者/>D-400(二者来自于Huntsman)或者平均分子量Mn为300-500g/mol的聚氧亚丙基三胺,例如/>T-403(来自于Huntsman)。
另外特别优选的另外的胺是IPDA,优选作为与二环氧化物的胺官能化加合物的一部分,优选作为与双酚A二缩水甘油基醚或者双酚F二缩水甘油基醚或者双酚A/F二缩水甘油基醚的加合物的一部分。
优选本发明的硬化剂包含仅仅到这样的程度的另外的胺,即,所述硬化剂中全部的胺氢数目的至少50%来自于式(I)以及至少一种聚氧亚烷基多胺和二环氧化物的胺官能化加合物的二者的胺。
本发明的硬化剂可以包含至少一种稀释剂。
特别合适的稀释剂是二甲苯,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,苄醇,乙二醇,乙二醇二甲基醚,乙二醇二乙基醚,乙二醇二丁基醚,乙二醇二苯基醚,二甘醇,二甘醇单甲基醚,二甘醇单乙基醚,二甘醇单正丁基醚,二甘醇二甲基醚,二甘醇二乙基醚,二甘醇二正丁基醚,丙二醇丁基醚,丙二醇苯基醚,二丙二醇,二丙二醇单甲基醚,二丙二醇二甲基醚,二丙二醇二正丁基醚,二苯基甲烷,二异丙基萘,石油馏分例如等级(来自于Exxon),腰果酚(来自于腰果壳油(cashew nutshell oil),含有作为主要成分的3-(8,11-十五碳二烯基)酚),苯乙烯化的酚,双酚,芳烃树脂,特别是含有酚基的那些,烷氧基化的酚,特别是乙氧基化或者丙氧基化的酚,特别是2-苯氧基乙醇,己二酸酯,癸二酸酯,邻苯二甲酸酯,苯甲酸酯,有机磷酸酯或者磺酸酯或者磺酰胺。
优选的是沸点大于200℃的稀释剂。
特别优选的是选自苄醇,二丙二醇和腰果酚的稀释剂。
本发明的硬化剂可以包含至少一种促进剂。
特别合适的促进剂是酸或者可以水解成酸的化合物,更特别是有机羧酸例如乙酸,苯甲酸,水杨酸,2-硝基苯甲酸或者乳酸,有机磺酸例如甲烷磺酸,对甲苯磺酸或者4-十二烷基苯磺酸,磺酸酯例如对甲苯磺酸甲酯,或者磷酸;硝酸盐例如硝酸钙;叔胺例如1,4-二氮杂双环[2.2.2]辛烷,苄基二甲基胺,α-甲基苄基二甲基胺,三乙醇胺,二甲基氨基丙基胺,咪唑例如N-甲基咪唑,N-乙烯基咪唑或者1,2-二甲基咪唑,这样的叔胺的盐,季铵盐例如苄基三甲基氯化铵,脒例如1,8-二氮杂双环[5.4.0]十一碳-7-烯,胍例如1,1,3,3-四甲基胍,酚醛树脂或者曼尼奇碱例如2-(二甲基氨基甲基)酚或者特别是2,4,6-三(二甲基氨基甲基)酚,或者来自酚、甲醛和N,N-二甲基-1,3-丙二胺的聚合物,亚磷酸酯例如亚磷酸二苯基或者三苯基酯,或者含有巯基的化合物。
优选的促进剂选自水杨酸,对甲苯磺酸,对甲苯磺酸甲酯,硝酸钙,2,4,6-三(二甲基氨基甲基)酚及其组合。
优选,所述硬化剂基本上没有分子量低于120g/mol的小胺(small amine)。这样的硬化剂在低气味和固化后光泽表面方面是有益的。
优选,所述硬化剂基本上没有高毒性胺例如N-氨基乙基哌嗪。
优选,所述硬化剂基本上没有沸点为200℃或者更低的低沸点稀释剂。
优选,所述硬化剂基本上没有有毒稀释剂,例如壬基酚,其它高毒性的烷基酚或者双酚A。
优选,所述硬化剂在25℃的粘度是0.5-7Pa.s,更优选1-6Pa.s,特别是2-5Pa.s,其是用锥/板流变仪,以锥直径20mm,锥角度2°和剪切速率600s-1测量的。这样的硬化剂能够以优选的层厚度来良好地施用铸塑树脂。
本发明另一目标是一种环氧树脂组合物,其包含:
–树脂组分,其包含至少一种环氧树脂,和
–硬化剂组分,其包含前述本发明硬化剂。
所述环氧树脂优选是液体环氧树脂或者两种或者更多种液体环氧树脂的混合物。
术语“液体环氧树脂”表示工业级聚环氧化物,其玻璃化转变温度低于25℃。
非必要地,包含至少一种液体环氧树脂的树脂组分可以进一步包含少量固体环氧树脂。
特别合适的环氧树脂是芳族环氧树脂,特别是下面组分的缩水甘油基化产物:
–双酚A,双酚F或者双酚A/F;
–间苯二酚,对苯二酚或者儿茶酚;
–另外的双酚或者多酚,例如双(4-羟基-3-甲基苯基)甲烷,2,2-双(4-羟基-3-甲基苯基)丙烷(双酚C),双(3,5-二甲基-4-羟基苯基)甲烷,2,2-双(3,5-二甲基-4-羟基苯基)丙烷,2,2-双(3,5-二溴-4-羟基苯基)丙烷,2,2-双(4-羟基-3-叔丁基苯基)丙烷,2,2-双(4-羟基苯基)丁烷(双酚B),3,3-双(4-羟基苯基)戊烷,3,4-双(4-羟基苯基)己烷,4,4-双(4-羟基苯基)庚烷,2,4-双(4-羟基苯基)-2-甲基丁烷,2,4-双(3,5-二甲基-4-羟基苯基)-2-甲基丁烷,1,1-双(4-羟基苯基)环己烷(双酚Z),1,1-双(4-羟基苯基)-3,3,5-三甲基环己烷(双酚TMC),1,1-双(4-羟基苯基)-1-苯基乙烷,1,4-双[2-(4-羟基苯基)-2-丙基]苯(双酚P),1,3-双[2-(4-羟基苯基)-2-丙基]苯(双酚M),4,4'-二羟基二苯基(DOD),4,4'-二羟基二苯甲酮,双(2-羟基萘-1-基)甲烷,双(4-羟基萘-1-基)甲烷,1,5-二羟基-萘,三(4-羟基苯基)甲烷,1,1,2,2-四(4-羟基苯基)乙烷,双(4-羟基苯基)醚或者双(4-羟基苯基)砜;
–酚醛清漆,其优选是酚或者甲酚与甲醛,多聚甲醛,乙醛,巴豆醛,异丁醛,2-乙基己醛,苯甲醛或者糠醛进行缩合的产物;
–芳族胺例如苯胺,甲苯胺,4-氨基酚,4,4'-亚甲基二苯基二胺,4,4'-亚甲基二苯基二-(N-甲基)胺,4,4'-[1,4-亚苯基-双(1-甲基乙叉基)]双苯胺(双苯胺P)或者4,4'-[1,3-亚苯基-双(1-甲基乙叉基)]双苯胺(双苯胺M)。
合适的液体环氧树脂是另外的脂族或者脂环族聚环氧化物,特别是:
–二-,三-或者四-官能化C2-到C30-醇的缩水甘油基醚,特别是以下的缩水甘油基醚:乙二醇,丙二醇,丁二醇,己二醇,辛二醇,聚丙二醇,二羟甲基环己烷,新戊二醇,二溴新戊二醇,蓖麻油,三羟甲基丙烷,三羟甲基乙烷,季戊四醇,山梨醇或者甘油,或者烷氧基化甘油或者烷氧基化三羟甲基丙烷;
–氢化的双酚A,F或者A/F液体树脂,或者氢化的双酚A,F或者A/F的缩水甘油基化产物;
–酰胺或者杂环氮碱的N-缩水甘油基衍生物,例如氰尿酸三缩水甘油基酯或者异氰尿酸三缩水甘油基酯,或者表氯醇与乙内酰脲的反应产物;
–来自于烯烃氧化的环氧树脂,所述烯烃例如乙烯基环己烯,二环戊二烯,环己二烯,环十二碳二烯,环十二碳三烯,异戊二烯,1,5-己二烯,丁二烯,聚丁二烯或者二乙烯基苯。
所述树脂组分的环氧树脂优选是基于双酚的芳族液体环氧树脂。具体地,它是工业级的双酚A,F或者A/F二缩水甘油基醚。这些树脂是低粘性的,并且能够快速固化和具有高硬度。
非必要地,所述树脂组分包含少量固体双酚A树脂或者酚醛清漆缩水甘油基醚。
优选所述树脂组分进一步包含至少一种反应性稀释剂,特别是环氧官能化的反应性稀释剂,特别是选自丁二醇二缩水甘油基醚,新戊二醇二缩水甘油基醚,己二醇二缩水甘油基醚,环己烷二甲醇二缩水甘油基醚,三羟甲基丙烷二-或者三缩水甘油基醚,苯基缩水甘油基醚,甲苯基缩水甘油基醚,愈创木酚(guiacol)缩水甘油基醚,4-甲氧基苯基缩水甘油基醚,对正丁基苯基缩水甘油基醚,对叔丁基苯基缩水甘油基醚,4-壬基苯基缩水甘油基醚,4-十二烷基苯基缩水甘油基醚,腰果酚缩水甘油基醚,苄基缩水甘油基醚,烯丙基缩水甘油基醚,丁基缩水甘油基醚,己基缩水甘油基醚,2-乙基己基缩水甘油基醚和天然醇例如C8-C10醇,C12-C14醇和C13-C15醇的缩水甘油基醚。
优选其是丁二醇二缩水甘油基醚,新戊二醇二缩水甘油基醚,己二醇二缩水甘油基醚,对叔丁基苯基缩水甘油基醚,C12-C14或者C13-C15烷基缩水甘油基醚,或者其混合物。
所述环氧树脂组合物可以包含另外的成分。
优选的另外的成分是沸点为至少200℃的稀释剂,例如已经提及的那些。优选的稀释剂选自苄醇,二丙二醇和腰果酚。
另一优选的另外的成分是促进剂,例如已经提及的那些,优选水杨酸,对甲苯磺酸,对甲苯磺酸甲酯,硝酸钙,2,4,6-三(二甲基氨基甲基)酚或者其组合。
另一优选的另外的成分是添加剂,例如表面活性剂,抗氧化、热、光或者UV辐射的稳定剂,或者杀生物剂。
另一非必要的成分是另外的反应性稀释剂,例如环氧化大豆油,环氧化亚麻籽油,乙酰乙酰基化多元醇,丁内酯,碳酸酯,醛,异氰酸酯或者具有反应性基团的硅酮,溶剂,另外的胺,具有巯基的物质,聚合物,热解法二氧化硅,纤维例如玻璃纤维,聚酰胺纤维,或聚乙烯纤维,玻璃空心球,流变改性剂,附着力促进剂例如有机烷氧基硅烷,或者阻燃剂。
根据本发明的一种非透明的环氧树脂组合物可以包含另外的成分,特别是填料例如碳酸钙,非必要地用脂肪酸进行了表面处理,重晶石,滑石,石英粉,石英砂,碳化硅,铁云母,白云石,钙硅石,高岭土,云母,分子筛,铝氧化物,铝氢氧化物,氢氧化镁,二氧化硅,水泥,石膏,飞灰,炭黑,石墨,金属粉,PVC粉或者空心球,和/或颜料例如二氧化钛或者铁氧化物,和/或纤维或者纳米材料例如碳纤维,金属纤维,陶瓷纤维或者碳纳米管。
根据本发明的一种透明的环氧树脂组合物可以进一步包含染料,来获得透明的有色外观,例如呈蓝色或者呈绿色或者呈红色,类似于有色玻璃。
优选,根据本发明的环氧树脂组合物是透明的。优选,这样的组合物包含至少一种抗光或者UV辐射的稳定剂。
在所述环氧树脂组合物中,对于环氧基团具有反应性的基团(主要是胺氢)的数目与环氧基团数目之比优选是0.5-1.5,特别是0.7-1.2。
胺氢与组合物中存在的环氧基团反应,并且将后者开环(加成反应)。主要作为这个反应的结果,所述组合物经历了聚合和因此发生了固化。
所述环氧树脂组合物的树脂组分和硬化剂组分各自存储在单独的容器中。所述环氧树脂组合物另外的成分可以是树脂组分或者硬化剂组分的一部分,而与胺具有反应性的成分是树脂组分的一部分,与环氧化物具有反应性的成分是硬化剂组分的一部分。
用于存储所述树脂组分或者硬化剂组分的合适的容器具体是罐,带锁扣盖的小圆筒(hobbock),小袋,桶,提桶,小罐,料筒或者管。
每种组分是存储稳定的。这意味着它在使用前可以保持几个月高到一年或者几年,而不遭受对于它的应用来说,它的性能发生任何程度的改变。
对于所述环氧树脂组合物的使用来说,将所述树脂组分、硬化剂组分和如果存在的另外的组分在即将施用之前或者施用期间彼此混合。优选对混合比进行选择,以使得胺氢和环氧基团处于彼此适当的比率,如前面所给出的。在重量份方面,树脂组分和硬化剂组分之间的混合比通常是1:10-10:1。所述组分依靠合适的方法彼此混合。这可以连续或者间歇进行。如果在施用前进行混合,则应当确保在组分混合和施用之间不留下过多的逝去时间,来确保在有效期内施用。混合优选在环境温度或者稍微升高的温度,特别是在10-50℃,优选15-30℃进行。环氧树脂组合物的固化是通过如上所述混合所述组分发生化学反应来开始。固化通常在10-150℃的温度,优选在环境温度进行。如果期望,可以在升高的温度,优选在50-150℃进行后固化。到固化的时间取决于包括温度、反应性成分的反应性和它们的化学计量和促进剂和/或稀释剂存在的因素。
本发明的环氧树脂组合物在25℃的粘度是1-7Pa·s,优选2-5Pa·s,其是在它的组分混合后2分钟,通过锥/板流变仪测量的,锥直径是20mm,锥角是2°和剪切速率是600s-1。
在固化时,本发明的环氧树脂组合物表现出低发热。优选它的反应焓小于400J/g,更优选小于380J/g,其是通过差示扫描量热法(DSC)在25-250℃和10℃/min测量的。这样的低焓允许以厚层施用,而不产生热区(其会导致气泡和/或变色)。
本发明的环氧树脂组合物优选以这样的方式配制,即,它的有效期是20-180min,优选25-120min,更优选30-80min,其是根据ASTM D 2471-99,用110g的组合物测量的。所述有效期可以通过添加另外的胺、稀释剂和/或促进剂来调节。
在这个优选的有效期范围内,本发明的环氧树脂组合物优选具有小于180℃,特别是小于160℃的放热峰值温度,其是根据ASTM D 2471-99,用110g的组合物测量的。
本发明的环氧树脂组合物在固化后具有高Tg。优选所述Tg(其是通过DSC,在25-250℃的两个试验中测量的,加热速率是10℃/min)在第二试验中高于50℃,更优选高于55℃,特别是至少60℃。这样的材料在环境条件是耐久的和稳定的。
本发明另一主题是本发明的环氧树脂组合物作为铸塑树脂来制造铸塑制品的用途,优选装饰性制品例如图画,抽象拼贴画,压纸器,装饰球,托盘,桌板,靠墙桌子等。
对于这个用途来说,所述环氧树脂组合物优选施用到表面上或者模具中。它可以一层施用或者将几个层彼此叠置施用。它优选如下来施用:将液态的混合材料在它的有效期内铸塑到表面上或者模具中或者已经施用并且至少部分固化的环氧树脂组合物的层上。
一个层优选以下述厚度铸塑:1-100mm,优选3-75mm,更优选5-50mm。
所述表面或者模具可以是这样,即,固化的环氧树脂可以从表面或者模具除去,而不损坏固化的材料,来通过它本身形成制品,或者所述表面或者模具是用固化的环氧树脂组合物永久涂覆或者填充的,以使得它们一起形成制品,或者其组合。
只要所述组合物仍然是液体,则成形材料例如木片或者石头,干花,人造珍珠或者装饰片可以引入所述组合物,以使得它们在最终制品中是可见的,来用于装饰性目的。
本发明另一主题是一种铸塑制品的方法,其包括步骤:
(i)将本发明的环氧树脂组合物的组分进行混合,
(ii)将所述混合的组合物在它的有效期内以1-100mm的层厚浇注到模具中,
(iii)非必要地混合步骤(i)所述的环氧树脂组合物的另一部分的组分,随后将所述混合的组合物的另一层在它的有效期内浇注到所述已经施用的、至少部分固化的层上,
非必要地重复步骤(iii),直到制品已经达到它期望的厚度,随后固化所述铸塑制品。
对于每个步骤,装饰性成形材料例如木片或者石头,干花,着色片或者人造珍珠可以引入所述组合物中。这可以通过将这样的制品置于模具中或者已经施用的层上或者通过将它们加入到新鲜混合的并且仍然流动的组合物中来实现。
所述模具可以是这样的材料,其可以从所施用的组合物上在所述组合物固化后除去,例如硅酮材料,或者它可以是这样的材料,其粘附到固化的组合物上,并且最后成为最终制品例如装饰性木头的一部分,或者其组合。
在所述环氧树脂组合物固化后,所获得的制品可以进一步处理,特别是通过拖曳,钻孔,切割,研磨,光滑化,擦拭,抛光等来处理。
本发明的另一主题是一种铸塑制品,其含有根据本发明的固化的环氧树脂组合物,优选通过上述方法获得。
优选,所获得的制品是装饰性制品,优选是选自绘画,抽象拼贴画,压纸器,装饰球,托盘,装饰盘,桌板和靠墙桌子。
一种特别优选的制品是桌板,特别是这样的桌板,其包含引入到本发明固化的环氧组合物中的一个或多个木片。
本发明的环氧树脂组合物是高度透明的,具有玻璃状外观和非常抗黄变的稳定性。它可以作为铸塑树脂以高的层厚度例如5-50mm浇注,和在环境温度快速和可靠地固化,并且具有低发热,来形成不粘的透明材料,具有光滑表面。它可以配制成无有毒稀释剂例如壬基酚。
具体实施方式
实施例
下面的实施例举例说明而非限制本发明。
“AHEW”表示胺氢当量。
“EEW”表示环氧基团当量。
“正常气候”表示23±1℃温度和50±5%的相对大气湿度。
未另外规定的化学物质来自于Sigma-Aldrich Chemie GmbH。
粘度是在恒温锥/板流变仪Lamy RM 200(锥直径20mm,锥角度2°,剪切速率600s-1)上测量的。
胺值(amine number)是通过滴定来测定的(使用乙酸中0.1NHClO4,相对于结晶紫)。
制备式(I)的胺:
胺A1:1-((2-氨基丙基)氨基)-3-(2-甲基苯氧基)丙-2-醇
在氮气氛下将474g(6.4mol)的1,2-丙二胺置于圆底烧瓶中,并且加热到70℃,随后以这样的方式添加293g(1.6mol环氧基团)的邻甲苯基缩水甘油基醚(DY-K,来自于Huntsman),即,将反应混合物的温度保持在70-85℃。在大约80℃另外一小时后,将所述反应混合物冷却,并且在薄膜蒸发器(0.5–1mbar,夹套温度115℃)上除去挥发物,主要是未反应的1,2-丙二胺。获得了无色液体,其胺值是479mg KOH/g,20℃粘度是12.3Pa·s和AHEW是90g/eq。
制备胺官能化加合物:
加合物B1:
将750g的T-403(聚氧亚丙基三胺,平均分子量Mn是430g/mol和AHEW是81g/eq,来自于Huntsman)置于圆底烧瓶中,并且加热到70℃,随后以这样的方式添加250g的/>GY250(双酚A二缩水甘油基醚,EEW 187g/eq,来自于Huntsman),即,使得反应混合物的温度不超过120℃。在大约100℃另外一小时后,将所述反应混合物冷却。获得了无色液体,其20℃粘度是90Pa·s和AHEW是126g/eq。
加合物B2:
将850g的1-氨基-3-氨基甲基-3,5,5-三甲基环己烷(IPD,AHEW是42.6g/eq,来自于Evonik)置于圆底烧瓶中,并且加热到70℃,随后以这样的方式添加15g的GY 250(双酚A二缩水甘油基醚,EEW 187g/eq,来自于Huntsman),即,使得反应混合物的温度不超过120℃。在大约100℃另外一小时后,将所述反应混合物冷却。获得了无色液体,其20℃粘度是0.35Pa·s和AHEW的52.5g/eq。
加合物B1是根据本发明的聚氧亚烷基多胺的胺官能化加合物。
制备硬化剂:
硬化剂H1到H7:
每种硬化剂是通过将表1给出的成分混合来制备的。将它存储在密闭容器中。
带有“(Ref.)”的硬化剂是参照实施例。
表1:硬化剂H1到H7的组成(重量份),AHEW(计算的)和粘度。
制备树脂组分:
树脂组分-1
将91.2g双酚A二缩水甘油基醚(GY 250,EEW 187g/eq,来自于Huntsman),7.0g的1,6-己烷二醇二缩水甘油基醚(/>DY-H,EEW142g/mol,来自于Huntsman),1.5g的UV光吸收剂和0.3g表面添加剂混合和存储在密闭容器中。所述树脂组分-1的计算的EEW是186g/eq和在25℃的粘度是3.8Pa·s。
树脂组分-2
将89.7g的双酚A二缩水甘油基醚,5.5g的1,6-己烷二醇二缩水甘油基醚,1.5g的UV光吸收剂,0.3g的表面添加剂和3.0g的对甲苯磺酸甲酯混合和存储在密闭容器中。所述树脂组分-2,其是树脂组分-1的促进形式,其计算的EEW是193g/eq和在25℃的粘度是4.1Pa·s。
树脂组分-3
将90.75g的双酚A二缩水甘油基醚,6.55g的1,6-己烷二醇二缩水甘油基醚,1.5g的UV光吸收剂,0.3g的表面添加剂和0.9g的对甲苯磺酸甲酯混合和存储在密闭容器中。所述树脂组分-3,其是树脂组分-1的促进形式,并且促进剂少于树脂组分-2,其计算的EEW是188g/eq和在25℃的粘度是3.9Pa·s。
制备环氧铸塑树脂:
组合物C-1到C-8:
表2给出的树脂组分和硬化剂是如上所述制备的。然后,将它们以表2给出的比例(重量份)共混,并且用带有搅拌棒的钻床混合和如下测试:
粘度是使用新鲜混合的样品,通过已经给出的方法测定的。
有效期和放热峰值温度是在正常气候,使用新鲜混合的110g样品在直径63mm和高度65mm的塑料盒中根据ASTM D 2471-99测定的。
焓和Tg值(玻璃化转变温度)是用新鲜混合的样品,用Mettler Toledo DSC 823e在25-250℃范围以10℃/min加热速率,在两个试验中根据ISO 11357-5测定的。
肖氏D硬度是根据ISO 868,在正常气候,用58mm直径和9mm厚度的样品在16h、24h和7天的固化时间之后测定的。
外观(aspect)是用58mm直径和9mm厚度的固化样品(在正常气候中7天),通过将它置于白色坐标纸中来肉眼判断它的透明度来测定的。
黄变是用58mm直径和9mm厚度的固化样品,通过将它置于朝南的窗户的外侧上的垂直位置21天来测定的。然后,将所述样品置于白色坐标纸上,并且与相同的、但是没有曝露于UV光的样品相邻,并且肉眼判断两个样品之间的黄变差异。
组成和测试结果在表2中给出。
带有“(Ref.)”的组合物是参照实施例。
将市售的铸塑树脂Translux D 154(2组分透明的环氧树脂,含有壬基酚,来自于Sika Advanced Resins)以相同方式进行混合和测试,并且在表2中引用作为参照实施例。
表2:组合物C-1到C-8的组成(重量份),以及Translux D 154和组合物C1到C8的性能。
表2:(续)
表2显示了:放热峰值温度受到添加促进剂来加速有效期和固化的影响,而反应焓不受过多影响(参见组合物C-1和C-2)。为了获得良好的性能,最大反应焓不大于400J/g,优选小于380J/g是有益的。
Tg值为55℃和更大有益于获得良好的耐久性。
Claims (19)
1.用于环氧树脂的硬化剂,其包含:
-至少一种式(I)的胺,
其中:
A是二价C2-C15亚烷基、亚环烷基或者芳基亚烷基,和
R是C1-C15烷基,和
-至少一种聚氧亚烷基多胺和二环氧化物的胺官能化加合物。
2.根据权利要求1的硬化剂,其中A是1,2-亚丙基和R是邻甲基。
3.根据权利要求1-2任一项的硬化剂,其中所述胺官能化加合物的聚氧亚烷基多胺选自4,7,10-三氧杂十三烷-1,13-二胺、平均分子量Mn为170-500g/mol的α,ω-聚氧亚丙基二胺和平均分子量Mn为300-500g/mol的聚氧亚丙基三胺。
4.根据权利要求1-2任一项的硬化剂,其中所述胺官能化加合物是至少一种平均分子量Mn为300-500g/mol的聚氧亚丙基三胺与双酚A二缩水甘油基醚或者双酚F二缩水甘油基醚或者双酚A/F二缩水甘油基醚的胺官能化加合物。
5.根据权利要求1-2任一项的硬化剂,其中所述胺官能化加合物是通过聚氧亚烷基多胺和二环氧化物以聚氧亚烷基多胺分子:二环氧化物的每摩尔环氧基团的摩尔比为1.05-5进行反应来制备。
6.根据权利要求5的硬化剂,其中所述胺官能化加合物是通过聚氧亚烷基多胺和二环氧化物以聚氧亚烷基多胺分子:二环氧化物的每摩尔环氧基团的摩尔比为1.1-3进行反应来制备。
7.根据权利要求5的硬化剂,其中所述胺官能化加合物是通过聚氧亚烷基多胺和二环氧化物以聚氧亚烷基多胺分子:二环氧化物的每摩尔环氧基团的摩尔比为1.1-2进行反应来制备。
8.根据权利要求1-2任一项的硬化剂,其中所述式(I)的胺与至少一种聚氧亚烷基多胺和二环氧化物的胺官能化加合物的重量比是0.2/1-10/1。
9.根据权利要求8的硬化剂,其中所述式(I)的胺与至少一种聚氧亚烷基多胺和二环氧化物的胺官能化加合物的重量比是0.4/1-5/1。
10.根据权利要求1-2任一项的硬化剂,其包含选自下面的至少一种另外的胺:N-苄基-1,2-乙二胺、N-苄基-1,2-丙二胺、2,2(4),4-三甲基-1,6-己二胺、1,2-,1,3-或者1,4-二氨基环己烷、1,3-双(氨基甲基)环己烷、1,4-双(氨基甲基)环己烷、双(4-氨基环己基)甲烷、1-氨基-3-氨基甲基-3,5,5-三甲基环己烷、2(4)-甲基-1,3-二氨基环己烷、1,3-双(氨基甲基)苯、平均分子量Mn为170-500g/mol的聚氧亚丙基二胺、平均分子量Mn为300-500g/mol的聚氧亚丙基三胺、三亚乙基四胺、四亚乙基五胺、五亚乙基六胺、N,N'-双(3-氨基丙基)亚乙基二胺及其混合物。
11.根据权利要求10的硬化剂,其中所述另外的胺是平均分子量Mn为170-500g/mol的聚氧亚丙基二胺,或者平均分子量Mn为300-500g/mol的聚氧亚丙基三胺。
12.根据权利要求10的硬化剂,其中所述另外的胺是1-氨基-3-氨基甲基-3,5,5-三甲基环己烷,作为与二环氧化物的胺官能化加合物的一部分。
13.环氧树脂组合物,其包含:
-树脂组分,其包含至少一种环氧树脂,和
-硬化剂组分,其包含根据权利要求1-12任一项的硬化剂。
14.根据权利要求13的环氧树脂组合物,其是透明的。
15.根据权利要求13或者14的环氧树脂组合物,其在固化时具有小于400J/g的反应焓,其是通过差示扫描量热法,在25-250℃和10℃/min的加热速率测量的。
16.根据权利要求13-15任一项的环氧树脂组合物作为铸塑树脂来制造铸塑制品的用途。
17.铸塑制品的方法,其包括步骤:
(i)将根据权利要求13-15任一项的环氧树脂组合物的组分进行混合,
(ii)将所述混合的组合物在它的有效期内以1-100mm的层厚浇注到模具中,
(iii)非必要地混合步骤(i)所述的环氧树脂组合物的另一部分的组分,随后将所述混合的组合物的另一层在它的有效期内浇注到已经施用的、至少部分固化的层上,
非必要地重复步骤(iii),直到制品已经达到它期望的厚度,随后固化所述铸塑制品。
18.铸塑制品,其含有固化的根据权利要求13-15任一项的环氧树脂组合物。
19.根据权利要求18的铸塑制品,所述铸塑制品通过根据权利要求17的方法获得。
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US10301423B2 (en) * | 2014-08-13 | 2019-05-28 | Sika Technology Ag | Amine for low-emission epoxy resin compositions |
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CN105939992A (zh) * | 2014-02-07 | 2016-09-14 | Sika技术股份公司 | 用于低排放环氧树脂产物的胺 |
CN104231232A (zh) * | 2014-10-11 | 2014-12-24 | 安徽工程大学 | 一种聚醚胺改性水性环氧地坪用固化剂及其制备方法 |
CN107001771A (zh) * | 2014-12-19 | 2017-08-01 | 瀚森公司 | 用于环氧涂料的固化剂 |
CN106753137A (zh) * | 2017-01-03 | 2017-05-31 | 湖南柯盛新材料有限公司 | 一种多组份美缝剂及其制备方法 |
CN107424964A (zh) * | 2017-07-27 | 2017-12-01 | 武汉市三选科技有限公司 | 底部填充组成物及使用其之底部填充方法与电子组装组件 |
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EP4034585B1 (en) | 2023-08-02 |
WO2021058574A1 (en) | 2021-04-01 |
CN114746471A (zh) | 2022-07-12 |
US20220411571A1 (en) | 2022-12-29 |
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