CN104854077A - 用于低排放环氧树脂产品的胺 - Google Patents
用于低排放环氧树脂产品的胺 Download PDFInfo
- Publication number
- CN104854077A CN104854077A CN201380065721.4A CN201380065721A CN104854077A CN 104854077 A CN104854077 A CN 104854077A CN 201380065721 A CN201380065721 A CN 201380065721A CN 104854077 A CN104854077 A CN 104854077A
- Authority
- CN
- China
- Prior art keywords
- amine
- epoxy resin
- solidifying agent
- composition
- diamine
- 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
Links
- 229920000647 polyepoxide Polymers 0.000 title claims abstract description 89
- 239000003822 epoxy resin Substances 0.000 title claims abstract description 86
- 150000001412 amines Chemical class 0.000 title claims abstract description 84
- 239000000203 mixture Substances 0.000 claims abstract description 82
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 74
- -1 polyoxy Polymers 0.000 claims description 66
- 229920000768 polyamine Polymers 0.000 claims description 34
- 239000000463 material Substances 0.000 claims description 30
- 238000007711 solidification Methods 0.000 claims description 24
- 230000008023 solidification Effects 0.000 claims description 24
- 150000002118 epoxides Chemical group 0.000 claims description 22
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 21
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- 238000000034 method Methods 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000007788 liquid Substances 0.000 claims description 15
- 150000004985 diamines Chemical class 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 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 12
- 229930185605 Bisphenol Natural products 0.000 claims description 11
- 229920005989 resin Polymers 0.000 claims description 11
- 239000011347 resin Substances 0.000 claims description 11
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 9
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- JZUHIOJYCPIVLQ-UHFFFAOYSA-N 2-methylpentane-1,5-diamine Chemical compound NCC(C)CCCN JZUHIOJYCPIVLQ-UHFFFAOYSA-N 0.000 claims description 7
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 7
- LGYNIFWIKSEESD-UHFFFAOYSA-N 2-ethylhexanal Chemical compound CCCCC(CC)C=O LGYNIFWIKSEESD-UHFFFAOYSA-N 0.000 claims description 6
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 claims description 6
- 239000004698 Polyethylene Substances 0.000 claims description 6
- 238000005576 amination reaction Methods 0.000 claims description 6
- 238000005932 reductive alkylation reaction Methods 0.000 claims description 6
- MRNZSTMRDWRNNR-UHFFFAOYSA-N bis(hexamethylene)triamine Chemical compound NCCCCCCNCCCCCCN MRNZSTMRDWRNNR-UHFFFAOYSA-N 0.000 claims description 5
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 claims description 5
- GKQPCPXONLDCMU-CCEZHUSRSA-N lacidipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C1=CC=CC=C1\C=C\C(=O)OC(C)(C)C GKQPCPXONLDCMU-CCEZHUSRSA-N 0.000 claims description 5
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 claims description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
- 125000005263 alkylenediamine group Chemical group 0.000 claims description 4
- 125000001118 alkylidene group Chemical group 0.000 claims description 4
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- SVEMKBCPZYWEPH-UHFFFAOYSA-N 2,4,4-trimethylhexane Chemical compound CCC(C)(C)CC(C)C SVEMKBCPZYWEPH-UHFFFAOYSA-N 0.000 claims description 3
- HWRRQRKPNKYPBW-UHFFFAOYSA-N 2,4-dimethylcyclohexan-1-amine Chemical compound CC1CCC(N)C(C)C1 HWRRQRKPNKYPBW-UHFFFAOYSA-N 0.000 claims description 3
- BKLNQBQVKVVBTR-UHFFFAOYSA-N 3-ethylhexanal Chemical compound CCCC(CC)CC=O BKLNQBQVKVVBTR-UHFFFAOYSA-N 0.000 claims description 3
- KSMVBYPXNKCPAJ-UHFFFAOYSA-N 4-Methylcyclohexylamine Chemical compound CC1CCC(N)CC1 KSMVBYPXNKCPAJ-UHFFFAOYSA-N 0.000 claims description 3
- NSOXQYCFHDMMGV-UHFFFAOYSA-N Tetrakis(2-hydroxypropyl)ethylenediamine Chemical compound CC(O)CN(CC(C)O)CCN(CC(C)O)CC(C)O NSOXQYCFHDMMGV-UHFFFAOYSA-N 0.000 claims description 3
- QFTYSVGGYOXFRQ-UHFFFAOYSA-N dodecane-1,12-diamine Chemical compound NCCCCCCCCCCCCN QFTYSVGGYOXFRQ-UHFFFAOYSA-N 0.000 claims description 3
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- GEQHKFFSPGPGLN-UHFFFAOYSA-N cyclohexane-1,3-diamine Chemical compound NC1CCCC(N)C1 GEQHKFFSPGPGLN-UHFFFAOYSA-N 0.000 claims description 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims 3
- 239000000470 constituent Substances 0.000 abstract 1
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- 238000000576 coating method Methods 0.000 description 25
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- 125000001931 aliphatic group Chemical group 0.000 description 10
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 10
- 238000002156 mixing Methods 0.000 description 10
- MNAHQWDCXOHBHK-UHFFFAOYSA-N 1-phenylpropane-1,1-diol Chemical compound CCC(O)(O)C1=CC=CC=C1 MNAHQWDCXOHBHK-UHFFFAOYSA-N 0.000 description 8
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- 230000037452 priming Effects 0.000 description 7
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- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 3
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Abstract
本发明涉及胺,它可以有利地用于室温下固化的环氧树脂组合物中。所述胺非常有效地稀释所述组合物,可以实现快速和无干扰地固化(即使在湿润寒冷的条件下)并且降低脆性。所述胺特别适合用作低排放的、室温下固化的环氧树脂涂层,特别是地板覆盖物的成分。
Description
技术领域
本发明涉及以下领域:胺、用于环氧树脂的固化剂、环氧树脂产品及其用途,特别是作为涂层、覆盖物和涂漆。
现有技术
适用于涂布目的的环氧树脂产品应具有尽可能低的粘度,由此在环境温度下可良好地加工和自流平。另外,它们应尽可能快和无干扰地固化(即使在寒冷潮湿的条件),并且在此形成没有混浊、斑点或凹处的匀称的表面。最后,固化的涂层应在极低的脆性条件下具有高硬度,以便尽可能良好地抵抗机械应力。对于视觉要求很高的应用,例如地板的覆盖物,涂层此外还应尽可能不易在光影响下变黄。
为了这些性质,根据现有技术在环氧树脂涂层中使用常规的稀释剂。稀释剂通过减少雾浊效应的出现来改善涂层的可加工性,降低脆性,并且改善表面质量。“雾浊效应”是指在固化过程时出现的表面缺陷,例如混浊、斑点、粗糙和粘附,这通过胺与来自空气的二氧化碳(CO2)成盐(“雾浊”)而造成,并且特别是在空气湿度高和低温下出现。
通常使用的稀释剂,特别是苄醇以及乙二醇和烷基酚在室温下不与环氧树脂反应并且因此在固化过程时不掺入到树脂基质中。但是目前对低排放产品的需要增加,所述产品在固化之后具有低含量的可通过蒸发和扩散过程释放的物质。对于低排放的环氧树脂产品而言,不可掺入到的稀释剂因此只能以极少量使用或者根本不使用。
稀释环氧树脂的另一个可能性是在固化剂组分中使用增加量的小分子伯胺。但是所述胺,例如二亚乙基三胺、异佛尔酮二胺或二甲苯二胺,它们的气味重,强烈刺激皮肤和眼睛以及引起过敏,并且导致雾浊效应增强。
US 5,426,157描述了包含N,N’-二甲基化二胺的环氧树脂组合物。US 5,739,209描述了源自2-甲基-1,5-戊二胺的单烷基化二胺,其作为用于具有增强的柔韧性和耐抗性的环氧树脂的固化剂。但是,所描述的二胺稀释的低排放的环氧树脂涂层是不够的。
发明内容
因此,本发明的目的是提供一种胺,所述胺可以有利地用于特别适合于涂布目的的低排放、室温下固化的环氧树脂产品,它通过非常好地稀释环氧树脂,可以实现快速和无干扰地固化并且降低经固化的树脂的脆性。
令人惊讶地发现,式(I)的胺非常好地实现了所述目的。所述胺气味小且低挥发,尽管粘度非常低但非常好地稀释环氧树脂涂层,而不会过多地减慢固化速率或者引起雾浊效应。在固化过程中,所述胺将掺入到树脂基质中,并在高硬度下非常有效地降低脆性。与类似的胺如1,3-双(苄基氨基甲基)苯或1,3-双(2-苯基乙基氨基甲基)苯不同,所述胺令人惊讶地没有使得经固化的涂层更加变黄。
采用式(I)的胺可以得到用于低排放的、室温下固化的环氧树脂的固化剂,它满足生态品质保证例如根据Emicode(EC1Plus)、AgBB、DIBt、蓝天使(Der Blaue Engel)、AFSSET、RTS(M1)和美国绿色建筑协会(LEED)的条件,同时满足对加工性质和使用性质的高要求。
本发明的其它方面是其它独立权利要求的主题。本发明特别优选的实施方案是从属权利要求的主题。
本发明的实施方式
本发明的主题是式(I)的胺。
以“多(聚)”开头的物质名如多胺、多元醇或聚环氧化物在本文中表示一种物质,其形式上每个分子包含两个或更多个名称中出现的官能团。
“胺氢”表示伯氨基和仲氨基的氢原子。
“胺氢当量”表示固化剂或胺中存在的每个胺氢的固化剂或胺的重量份。
“不可掺入的稀释剂”表示可溶于环氧树脂并且使粘度下降的物质,它在环氧树脂固化过程中没有共价结合在树脂基质中。
“粘度”的概念在本文献中表示动态粘度或剪切粘度,通过剪切应力和剪切速率(速率梯度)之间的比例来定义,如在实施例中所述进行确定。
式(I)的胺是1,3-双(2-乙基己基氨基甲基)苯。
式(I)的胺可以特别有利地通过1,3-双(氨基甲基)苯(间二甲苯二胺或MXDA)与2-乙基己醛的还原性烷基化获得。所述还原性烷基化可以直接与分子氢或间接通过来自其它试剂的氢转移来进行。优选使用分子氢。在此选择有利的环境,使得一方面简单地烷基化具有良好选择性的伯氨基基团,另一方面不氢化苯环。
优选在氢压力为5巴至100巴,温度为40℃至120℃和适当的催化剂存在下进行处理。作为催化剂,优选的是钯碳(Pd/C)、铂碳(Pt/C)、亚当斯催化剂和雷尼镍,特别是钯碳和铂碳。
通过基于所述方式的还原性烷基化来制备式(I)的胺对于作为环氧树脂的固化剂的成分的用途是特别有利的,因为具有良好选择性的伯氨基基团容易被烷基化,而仲氨基基团则几乎不被进一步烷基化。来自所述制备方法的产品因此可以在没有进一步处理的条件下用于以所述方式固化环氧树脂。
本发明的另一主题因此是用于制备式(I)的胺的方法,所述方法通过1,3-双(氨基甲基)苯与2-乙基己醛和氢的还原性烷基化进行。
优选地,2-乙基己醛与1,3-双(氨基甲基)苯以在1.4/1至2.4/1,特别是1.6/1至2.2/1的范围内的摩尔比使用。
在环氧树脂固化剂的应用过程中,摩尔比<1.4/1可能导致稀释效果和雾浊方面不太理想的结果,而摩尔比>2.4/1则要求复杂的后清洗。
特别优选的是摩尔比为约2/1。在此,可以以高纯度获得不需要额外处理的式(I)的胺,并且作为环氧树脂固化剂的成分起到极好的稀释作用和降低脆性作用。
另外,特别优选摩尔比例为约1.6/1。所得的反应混合物除了式(I)的胺之外,还包含相当大量的N-2-乙基己基-1,3-双(氨基甲基)苯。作为环氧树脂固化剂的成分,它具有良好的稀释作用,适中的降低脆性的作用并可以实现特别快速的固化。
式(I)的胺还可以不同于还原性烷基化的其它方式来获得,特别是通过1,3-双(氨基甲基)苯与2-乙基己醛氯或2-乙基己基溴以合适的比例反应来获得。在此产生反应混合物,其典型地具有相当大量的双烷基化的氨基基团。
式(I)的胺是低挥发性、气味小的物质,具有非常低的粘度。它与CO2的反应性极低,因此与很多现有技术中已知的胺不同,在空气中不形成硬壳也不沉淀或粘度增加。显示出与另外的胺和与环氧树脂极好的相容性。尽管存在芳香环,但所述胺在经固化的环氧树脂涂层中也令人惊讶地没有导致在光影响下增加的变黄。
本发明的另一主题是式(I)的胺作为稀释剂,特别是环氧树脂的固化剂中的稀释剂的用途。
式(I)的胺具有相对高的胺氢当量。由此可以大量用在环氧树脂的固化剂中,并且在没有过多影响固化反应的条件下稀释所述固化剂。
在环氧树脂的固化剂具有高粘度的情况下,例如20℃时的粘度高于500mPa·s,特别是高于1,000mPa·s,式(I)的胺可以显著降低其粘度。
通过使用式(I)的胺作为稀释剂可以得到用于环氧树脂的低粘度的固化剂,它们完全不含不可掺入的稀释剂,并因此可以实现具有高硬度、低脆性和低变黄倾向的低排放环氧树脂。
本发明的另一主题是适合于固化环氧树脂的固化剂,其包含式(I)的胺和至少一种多胺A,所述多胺A具有至少三个对环氧基团呈反应性的胺氢。
适合作为多胺A的特别是以下多胺:
-脂族、环脂族或芳脂族的伯二胺,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-和2,4,4-三甲基己二胺(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-和1,4-二氨基环己烷、双(4-氨基环己基)甲烷(H12-MDA)、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-和4-甲基-1,3-二氨基环己烷及其混合物、1,3-和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(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-薄荷烷二胺、3,9-双(3-氨基丙基)-2,4,8,10-四氧杂螺[5.5]十一烷以及1,3-和1,4-双(氨基甲基)苯;
-脂族、环脂族或芳脂族的伯三胺,特别是4-氨基甲基-1,8-辛二胺、1,3,5-三(氨基甲基)苯、1,3,5-三(氨基甲基)环己烷、三(2-氨基乙基)胺、三(2-氨基丙基)胺和三(3-氨基丙基)胺;
-含醚基团的脂族伯二胺,特别是双(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-1,13-二胺以及这些二胺的高级低聚物,双(3-氨基丙基)聚四氢呋喃和其它聚四氢呋喃二胺,来自1,4-二羟甲基环己烷的丙氧基化和随后的胺化的含醚基团的环脂族二胺,特别是作为RFD-270(来自Huntsman)可获得的;以及聚氧亚烷基二胺,典型地是来自聚氧亚烷基二醇的胺化的产物并且可以例如以名称(来自Huntsman)、以名称聚醚胺(来自BASF)或者以名称PC(来自Nitroil)获得。特别适合的聚氧亚烷基二胺是D-230、D-400、D-2000、EDR-104、EDR-148和EDR-176,以及来自BASF或Nitroil的相应的胺;
-伯聚氧亚烷基三胺,其典型地是来自聚氧亚烷基三醇的胺化的产物并且可以例如名称(来自Huntsman)、以名称聚醚胺(来自BASF)或以名称PC(来自Nitroil)获得,特别是T-403、T-3000、T-5000,以及来自BASF或Nitroil的相应的胺;
-具有两个脂族伯氨基基团的具有叔氨基的多胺,特别是如N,N'-双(氨基丙基)哌嗪、N,N-双(3-氨基丙基)甲胺、N,N-双(3-氨基丙基)乙胺、N,N-双(3-氨基丙基)丙胺、N,N-双(3-氨基丙基)环己基胺、N,N-双(3-氨基丙基)-2-乙基-己基胺,以及来自衍生自天然脂肪酸的脂肪胺的双重氰基乙基化和随后的还原的产物,例如N,N-双(3-氨基丙基)十二烷基胺和N,N-双(3-氨基丙基)牛脂烷基胺,其可以以Y12D和YT获得(来自Akzo Nobel);
-具有三个脂族伯氨基基团的具有叔氨基的多胺,特别是如三(2-氨基乙基)胺、三(2-氨基丙基)胺和三(3-氨基丙基)胺;
-具有两个脂族伯氨基基团的具有仲氨基基团的多胺,特别是如3-(2-氨基乙基)氨基丙基胺、双六亚甲基三胺(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)和线性聚亚乙基胺高级同系物,例如具有5至7个亚乙基胺单元的聚亚乙基多胺(所谓的“高级亚乙基多胺”,HEPA)、来自具有至少两个伯氨基基团的伯二胺和伯多胺的多重氰基乙基化或氰基丁基化和随后氢化的产物,例如二亚丙基三胺(DPTA)、N-(2-氨基乙基)-1,3-丙二胺(N3-胺)、N,N’-双(3-氨基丙基)乙二胺(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-氨基无机)-1,3-戊二胺、N5-(3-氨基-1-乙基丙基)-2-甲基-1,5-戊二胺和N,N’-双(3-氨基-1-乙基丙基)-2-甲基-1,5-戊二胺;
-具有伯氨基基团和仲氨基基团的多胺,特别是如N-丁基-1,2-乙二胺、N-己基-1,2-乙二胺、N-(2-乙基己基)-1,2-乙二胺、N-环己基-1,2-乙二胺、4-氨基甲基-哌啶、N-(2-氨基甲基)哌嗪、N-甲基-1,3-丙二胺、N-丁基-1,3-丙二胺、N-(2-乙基己基)-1,3-丙二胺、N-环己基-1,3-丙二胺、3-甲基氨基-1-戊胺、3-乙基氨基-1-戊胺、3-环己基氨基-1-戊胺,脂肪二胺如N-环烷基-1,3-丙二胺,和脂族伯二胺与以下物质在1:1的摩尔比下进行反应的迈克尔加成反应的产物:丙烯腈、马来酸二酯或富马酸二酯、柠康酸二酯、丙烯酸酯和甲基丙烯酸酯、丙烯酰胺和甲基丙烯酰胺以及衣康酸二酯;另外,脂族伯多胺与醛或酮的部分还原性烷基化产物,特别是N-2-乙基己基-1,3-双(氨基甲基)苯,以及部分苯乙烯化的多胺如240(来自三菱气体化学(Mitsubish GasChemical)(MGC));
-芳族多胺,特别是如间苯二胺和对苯二胺、4,4'-、2,4’和2,2’-二氨基二苯基甲烷、3,3'-二氯-4,4'-二氨基二苯基甲烷(MOCA)、2,4-和2,6-甲苯二胺、3,5-二甲基硫-2,4-和-2,6-甲苯二胺的混合物(可以以300从Albemarle获得)、3,5-二乙基-2,4-和-2,6-甲苯二胺(DETDA)的混合物、3,3',5,5'-四乙基-4,4'-二氨基二苯基甲烷(M-DEA)、3,3',5,5'-四乙基-2,2'-二氯-4,4'-二氨基二苯基甲烷(M-CDEA)、3,3'-二异丙基-5,5'-二甲基-4,4'-二氨基二苯基甲烷(M-MIPA)、3,3',5,5'-四异丙基-4,4'-二氨基二苯基甲烷(M-DIPA)、4,4'-二氨基二苯基砜(DDS)、4-氨基-N-(4-氨基苯基)苯磺酰胺、5,5'-亚甲基二邻氨基苯甲酸、二甲基(5,5'-亚甲基二邻氨基苯甲酸酯)、1,3-亚丙基-双(4-氨基苯甲酸酯)、1,4-亚丁基-双(4-氨基苯甲酸酯)、聚四亚甲基氧化物-双(4-氨基苯甲酸酯)(可以以从Air Products获得)、1,2-双(2-氨基苯基硫)乙烷、2-甲基丙基(4-氯-3,5-二氨基苯甲酸酯)和叔丁基-(4-氯-3,5-二氨基苯甲酸酯);
-所述多胺与环氧化物和环氧树脂的加合物,特别是与二环氧化物以约2/1的摩尔比的加合物,与单环氧化物以至少1/1的摩尔比的加合物,以及胺和表氯醇的反应产物,特别是与1,3-双(氨基甲基)苯的反应产物,可以以328商购获得(来自MGC);
-聚酰氨基胺,其为由一元或多元羧酸或者它们的酯或酸酐,特别是二聚脂肪酸与化学计量过量使用的脂族、环脂族或芳族多胺,特别是聚亚烷基胺例如DETA或TETA的反应产物,特别是可商购获得的聚酰氨基胺100、125、140和150(来自Cognis)、223、250和848(来自Huntsman)、3607和530(来自Huntsman)和EH 651、EH 654、EH 655、EH 661和EH 663(来自Cytec);和
-苯烷基胺,也称为曼尼希碱,其为酚特别是腰果酚与醛特别是甲醛和多胺的反应产物,特别是商购可得的苯烷基胺NC-541、NC-557、NC-558、NC-566、Lite 2001和Lite 2002(来自Cardolite)、3440、3441、3442和3460(来自Huntsman)和EH 614、EH 621、EH 624、EH 628和EH 629(来自Cytec)。
多胺A优选选自: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、2,2,4-和2,4,4-三甲基己二胺(TMD)、1,12-十二烷二胺、1,3-二氨基环己烷、双(4-氨基环己基)甲烷(HMDA)、双(4-氨基-3-甲基环己基)甲烷、1-氨基-3-氨基甲基-3,5,5-三甲基环己烷(IPD)、1,3-双(氨基甲基)环己烷、1,3-双(氨基甲基)苯(MXDA)、双六亚甲基三胺(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)和线性聚亚乙基胺的高级同系物,例如具有5至7个亚乙基胺单元的聚亚乙基多胺(HEPA)、二亚丙基三胺(DPTA)、N-(2-氨基乙基)-1,3-丙二胺(N3-胺)、N,N’-双(3-氨基丙基)乙二胺(N4-胺)、分子量在200g/mol至300g/mol范围内的来自1,4-二羟甲基环己烷的丙氧基化和随后的胺化构成的含醚基团的环脂族二胺,特别是RFD-270(来自Huntsman),分子量在200g/mol至500g/mol范围内的聚氧亚烷基二胺和聚氧亚烷基三胺,特别是D-230、D-400和T-403类型,以及呈与环氧化物,特别是单环氧化物或环氧树脂的加合物形式的或呈迈克尔加合物、曼尼希碱或聚酰氨基胺形式的这些多胺的衍生物。
所述优选的多胺A与环氧树脂特别良好地相容,并使得高质量的膜成为可能。
特别优选地,所述多胺A是与环氧化物的加合物,特别是与环氧树脂或与单环氧化物的加合物。所述加合物显示出极好的作为环氧树脂的固化剂的性质,尤其是即使在低温下也快速的固化速率,并且不太易于出现雾浊效应。其产生优质的膜,但是由于其高粘度只有在高度稀释下才适合高粘度应用。在现有技术中,这典型地通过包含不可掺入的稀释剂和较大量的相对挥发性的小分子伯二胺的混合物来实现。但是,如果在此放弃使用不可掺入的稀释剂,则所述固化剂或导致高粘度或导致强烈的雾浊效应。通过采用式(I)的胺稀释所述加合物,可以获得具有用于低排放涂层的优良性质的环氧树脂固化剂。
多胺A特别优选是与芳族单环氧化物的加合物。所述加合物具有适中的粘度并且与环氧树脂良好地相容。
特别优选的单环氧化物是芳族缩水甘油醚,特别是甲苯基缩水甘油醚。适合作为甲苯基缩水甘油醚的是所有异构的甲苯基缩水甘油醚和它们的混合物,特别是商购可得的类型,特别是如DY-K(来自Huntsman)、PolypoxTM R6(来自Dow)、HeloxyTM KR(来自Hexion)或GE-10(来自CVC Spec.Chem.)。所述加合物与常规的环氧树脂产物具有特别良好的相容性,并且使得高光泽和高硬度的经固化的膜成为可能。
在本发明的一个方面中,所述固化剂包含至少两种不同的多胺A,特别是至少一种优选为与环氧树脂的加合物的多胺A1,和至少一种为非加合的多胺的多胺A2。通过用式(I)的胺稀释由多胺A1和多胺A2构成的这种混合物,可以将粘度和伯氨基基团的含量保持得如此低,从而可以获得具有良好可加工性、低雾浊效应倾向、快速固化和低脆性的低排放涂层。
优选地,式(I)的胺以这样的量存在于固化剂中,它的胺氢占固化剂中存在的胺氢总量的1%至75%,优选2%至50%,特别是5%至30%。
进一步优选地,式(I)的胺在固化剂中以这样的量存在,使得它的重量份额占所有对环氧基团呈反应性的胺总量的1%至95%,优选5%至75%,特别是5%至50%。
所述固化剂的特征在于低粘度,并且使得具有高固化速率、几乎没有雾浊效应倾向和在脆性低时具有高硬度的环氧树脂涂层成为可能。
所述固化剂另外可以包含至少一种促进剂。适合作为促进剂的是促进氨基基团和环氧基团之间的反应的物质,特别是酸或可以水解成酸的化合物,特别是有机羧酸例如乙酸、苯甲酸、水杨酸、2-硝基苯甲酸、乳酸;有机磺酸如甲磺酸、对甲苯磺酸或4-十二烷基苯磺酸;磺酸酯;其它有机或无机酸,特别是如磷酸,或者前述酸和酸酯的混合物;还有叔胺,特别是如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,特别是如N-甲基咪唑、N-乙烯基咪唑或1,2-二甲基咪唑;所述叔胺的盐,季铵盐,特别是如苄基三甲基氯化铵;脒特别是如1,8-二氮杂双环[5.4.0]十一-7-烯;胍特别是如1,1,3,3-四甲基胍;酚特别是双酚、酚树脂和曼尼希碱,特别是如2-(二甲基氨基甲基)苯酚、2,4,6-三(二甲基氨基甲基)苯酚和由苯酚、甲醛和N,N-二甲基-1,3-丙二胺构成的聚合物;亚磷酸酯特别是如二苯基亚磷酸酯和三苯基亚磷酸酯,以及具有巯基基团的化合物。
优选的促进剂是水杨酸和2,4,6-三(二甲基氨基甲基)苯酚。
另外,所述固化剂可以包含至少一种不可掺入的稀释剂,特别是二甲苯、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、乙二醇二甲醚、乙二醇二乙醚、乙二醇二丁醚、乙二醇二苯基醚、二乙二醇、二乙二醇单甲醚、二乙二醇单乙醚、二乙二醇单正丁基醚、二乙二醇二甲醚、二乙二醇二乙醚、二乙二醇二正丁基醚、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、二丙二醇二正丁基醚、N-甲基吡咯烷酮、二苯甲烷、二异丙基萘,石油馏分例如-类型(来自Exxon),烷基酚例如叔丁基苯酚、壬基苯酚、十二烷基苯酚和8,11,14-十五碳三烯基苯酚(腰果酚,来自腰果壳油,可以例如以Cardolite NC-700从美国Cardolite公司获得),苯乙烯化的苯酚、双酚、芳族烃树脂,特别是含苯酚基团的类型,烷氧基化的苯酚,特别是乙氧基化或丙氧基化的苯酚,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、有机磷酸酯和磺酸酯,和磺酰胺。优选的是苄醇、十二烷基苯酚、叔丁基苯酚、苯乙烯化的苯酚、乙氧基化的苯酚和含苯酚基团的芳族烃树脂,特别是类型LS500、LX200、LA300和LA700(来自Rütgers)。
所述固化剂优选不包含不可掺入的稀释剂或者只包含低含量的不可掺入的稀释剂,特别优选低于25重量%,特别是低于10重量%和最优选低于5重量%。尤其是不向所述固化剂中添加不可掺入的稀释剂。
所述固化剂可以包含其它对环氧基团呈反应性的物质,例如一元胺如己胺和苄胺;脂族仲多胺;具有巯基基团的化合物,特别是下列物质:
-液态的巯基封端的多硫化物聚合物,以商品名已知的(来自Morton Thiokol;例如可以由SPI Supplies或由Toray FineChemicals获得),特别是型号LP-3、LP-33、LP-980、LP-23、LP-55、LP-56、LP-12、LP-31、LP-32和LP-2;以及另外以商品名已知的(来自Akzo Nobel),特别是G 10、G 112、G 131、G 1、G 12、G 21、G 22、G 44和G 4的类型;
-巯基封端的聚氧亚烷基醚,可以例如通过聚氧亚烷基二醇和聚氧亚烷基三醇与表氯醇或与氧化烯烃,接着与硫氢化钠的反应获得;
-聚氧亚烷基衍生物形式的巯基封端的化合物,以商品名(来自Cognis)是已知的,特别是WR-8、LOF和3-800的类型;
-硫代羧酸的聚酯,例如季戊四醇四巯基乙酸酯、三羟甲基丙烷三巯基乙酸酯、乙二醇二巯基乙酸酯、季戊四醇-四-(3-巯基丙酸酯)、三羟甲基丙烷三-(3-巯基丙酸酯)和乙二醇二-(3-巯基丙酸酯),以及聚氧亚烷基二醇和聚氧亚烷基三醇、乙氧基化的三羟甲基丙烷和聚酯二醇与硫代羧酸例如硫代乙醇酸和2-或3-巯基丙酸的酯化产物;和
-具有其它巯基基团的化合物,特别是如2,4,6-三巯基-1,3,5-三嗪、2,2’-(亚乙基二氧)-二乙硫醇(三乙二醇-二硫醇)和乙二硫醇。
本发明的另一主题是环氧树脂组合物,其包含至少一种环氧树脂和前面所述的固化剂。
常规的工业环氧树脂适合作为环氧树脂。它们以已知的方式和方法获得,例如来自相应烯烃的氧化或者来自表氯醇与相应的多元醇、多酚或胺的反应。
特别适合作为环氧树脂的是所谓的聚环氧化物液体树脂,以下称为“液体树脂”。它的玻璃态转变温度低于25℃。
同样可以作为环氧树脂的是所谓的固体树脂,它具有高于25℃的玻璃态转变温度,并且能够粉碎成在25℃可以倾倒的粉末。
合适的环氧树脂特别是芳族环氧树脂,特别是以下物质的缩水甘油基化产物:
-双酚A、双酚F或双酚A/F,其中A表示丙酮且F表示甲醛,它们是用于制备所述双酚的反应物。在双酚F的情况下还可能存在位置异构体,特别是衍生自2,4’-和2,2’-羟苯甲基甲烷的位置异构体;
-二羟基苯衍生物如间苯二酚、对苯二酚和邻苯二酚;
-其它双酚或多酚,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'-二羟基联苯(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)醚和双(4-羟基苯基)砜;
-酚与甲醛的缩合产物,其在酸性条件下获得,如苯酚-酚醛清漆树脂(Novolaken)或甲酚-酚醛清漆树脂,也称为双酚F线性酚醛树脂;
-芳族胺,例如苯胺、甲苯胺、4-氨基苯酚、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-亚乙基)]双苯胺(双苯胺P)、4,4'-[1,3-亚苯基-双(1-甲基-亚乙基)]双苯胺(双苯胺M)。
其它合适的环氧树脂是脂族或环脂族聚环氧化物,特别是:
-以下物质的缩水甘油醚:饱和或不饱和的、支化或未支化的、环状或开链的、二官能、三官能或四官能的C2-至C30-醇,特别是乙二醇、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、山梨糖醇或甘油,以及烷氧基化的甘油或烷氧基化的三羟甲基丙烷;
-氢化的双酚A-、双酚F-或双酚A/F液体树脂,或者氢化双酚A、双酚F或双酚A/F的缩水甘油基化产物;
-酰胺或杂环氮碱的N-缩水甘油基衍生物,例如三缩水甘油基氰脲酸酯和三缩水甘油基异氰脲酸酯,以及表氯醇和乙内酰脲的反应产物;
-来自烯烃氧化的环氧树脂,特别是乙烯基环己烯、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、聚丁二烯或二乙烯基苯。
环氧树脂优选是基于双酚的液体树脂,特别是双酚A、双酚F或双酚A/F的二缩水甘油醚,例如可以从Dow、Huntsman和Hexion商购获得。所述液体树脂具有对环氧树脂的低粘度,并且在已固化状态具有作为涂层的良好性质。所述树脂可以任选地与双酚A固体树脂或双酚F-酚醛清漆环氧树脂组合存在。
所述环氧树脂可以包含反应性稀释剂,特别是具有至少一个环氧基团的反应性稀释剂。适合作为反应性稀释剂的是例如一元或多元酚和脂族或环脂族醇的缩水甘油醚,特别是如已经提到的二元醇或多元醇的聚缩水甘油醚,另外还特别是苯基缩水甘油醚、甲苯基缩水甘油醚、苄基缩水甘油醚、对正丁基-苯基缩水甘油醚、对叔丁基-苯基缩水甘油醚、壬基苯基缩水甘油醚、烯丙基缩水甘油醚、丁基缩水甘油醚、己基缩水甘油醚、2-乙基己基缩水甘油醚,以及天然醇的缩水甘油醚如C8-至C10-烷基缩水甘油醚或C12-或C14-烷基缩水甘油醚。向环氧树脂中添加反应性稀释剂起到降低粘度的作用,并且降低玻璃态转变温度和机械值。
所述环氧树脂组合物任选地包含其它成分,特别是环氧树脂组合物中通常使用的助剂和添加剂,例如以下物质:
-溶剂、稀释剂、成膜助剂或增量剂,例如特别是已经提到的不可掺入的稀释剂;
-反应性稀释剂,特别是具有环氧基团的反应性稀释剂,例如前面提到的那样,环氧化的大豆油或亚麻籽油,具有乙酰乙酸基团的化合物,特别是乙酰乙酸化的多元醇、丁内酯、碳酸酯、醛,以及其它异氰酸酯和具有反应性基团的硅树脂;
-聚合物,特别是聚酰胺、多硫化物、聚乙烯基甲醛(PVF)、聚乙烯基丁醛(PVB)、聚氨酯(PUR),具有羧基基团的聚合物、聚酰胺、丁二烯-丙烯腈-共聚物、苯乙烯-丙烯腈-共聚物、丁二烯-苯乙烯-共聚物、不饱和单体的均聚物或共聚物,特别是来自包括乙烯、丙烯、丁烯、异丁烯、异戊二烯、乙酸乙烯酯和(甲基)丙烯酸烷基酯的组,特别是氯代磺化聚乙烯和含氟聚合物,磺酰胺改性的蜜胺和纯化的褐煤蜡;
-无机和有机填料,例如任选地涂布有脂肪酸,特别是硬脂酸酯的经研磨或经沉淀的碳酸钙,重晶石(重土)、滑石、石英粉、石英砂、铁云母、白云石、硅灰石、高岭土,云母(硅酸铝钾)、分子筛、氧化铝、氢氧化铝、氢氧化镁、二氧化硅、水泥、石膏、飞灰、炭黑、石墨、金属粉末如铝、铜、铁、锌、银或钢,PVC粉末或空心球;
-纤维,特别是玻璃纤维、碳纤维、金属纤维、陶瓷纤维或合成纤维例如聚酰胺纤维或聚乙烯纤维;
-颜料,特别是二氧化钛或氧化铁;
-前面所述促进剂;
-流变改性剂,特别是增稠剂或抗沉降剂;
-增附剂,特别是有机烷氧基硅烷;
-对抗氧化、热、光和UV辐照的稳定剂;
-阻燃物质,特别是氢氧化铝(ATH)、氢氧化镁(MDH)、三氧化锑、五氧化锑、硼酸(B(OH)3)、硼酸锌、磷酸锌、硼酸三聚氰胺、氰尿酸三聚氰胺、多磷酸铵、磷酸三聚氰胺、热解磷酸三聚氰胺、多溴化二苯基氧化物或二苯醚,磷酸酯特别是例如二苯基甲苯基磷酸酯、间苯二酚-双(二苯基磷酸酯)、间苯二酚-二磷酸酯-低聚物、四苯基-间苯二酚-二亚磷酸酯、乙二胺二磷酸酯和双酚A-双(二苯基磷酸酯)、三-(氯乙基)磷酸酯、三-(氯丙基)磷酸酯和三(二氯异丙基)磷酸酯、三[3-溴-2,2-双(溴甲基)丙基]磷酸酯、四溴双酚A、双酚A的双-(2,3-二溴丙基醚)、溴化环氧树脂、亚乙基-双-(四溴-邻苯二甲酰亚胺)、亚乙基-双(二溴-降冰片烷二甲酰亚胺)、1,2-双-(三溴-苯氧基)乙烷、三-(2,3-二溴丙基)异氰脲酸酯、三溴苯酚、六溴环十二烷、双-(六氯环戊二烯子基)环辛烷和氯化石蜡;
-表面活性物质,特别是润湿剂、流平剂、脱气剂或消泡剂;
-杀生物剂,例如杀藻剂、杀真菌剂或抑制真菌生长的物质。
所述环氧树脂组合物优选包含其它助剂和添加剂,特别是润湿剂、流平剂、消泡剂、稳定剂、颜料和催化剂,特别是水杨酸或2,4,6-三-(二甲基氨基甲基)-苯酚。
所述环氧树脂组合物优选不含或只含有少量的不可掺入的稀释剂,特别优选小于10重量%,尤其小于5重量%,最优选小于2重量%。
所述环氧树脂组合物中,对环氧基团呈反应性的基团数目与环氧基团数目的比例优选在0.5至1.5范围内,特别是在0.7至1.2范围内。
存在于环氧树脂组合物中的胺氢和任选存在的其它对环氧基团呈反应性基团在环氧基团的开环条件下与其反应(加成反应)。这种反应的结果是,组合物聚合和随后固化。本领域技术人员已知的是,伯氨基基团对环氧基团是双官能的,因此将伯氨基基团视为两个对环氧基团呈反应性的基团。
所述环氧树脂组合物尤其是双组分组合物,它由以下物质构成:
(i)包含至少一种环氧树脂的树脂组分,和
(ii)包含所述固化剂的固化剂组分。
所述双组分组合物的组分分别储存在在适当的容器中。双组分环氧树脂组合物的其它组分可以作为树脂组分或固化剂组分的成分存在,其中对环氧基团呈反应性的其它成分优选是固化剂组分的成分。用于储存树脂组分或固化剂组分的合适的容器特别是例如桶、带锁扣的小提桶(Hobbock)、袋、筒、罐、胶罐或管。所述组分能够储存,即可以在其使用前保存几个月到一年和更长时间,而不会改变其应用相关的各种性能。为应用所述双组分环氧树脂组合物,在施用前不久或在施用期间将树脂组分和固化剂组分彼此混合。如此选择两种组分之间的混合比例,使得固化剂组分的对环氧基团呈反应性的基团与树脂组分中的环氧基团处于如前所述的适当的比例。树脂组分和固化剂组分之间的混合比例以重量份计通常在1:10至10:1的范围内。
两种组分的混合借助合适的方法进行,其可以连续地或间歇地进行。如果在施用之前进行混合,必须确保在所述组分的混合与施用之间不消耗太多的时间,因为例如对基材的缓慢或不完全的附着可能造成干扰。所述混合尤其在环境温度进行,所述环境温度典型地在约5℃至50℃的范围内,优选在约10℃至30℃的范围内。
随着两种组分的混合,通过化学反应开始固化,如前所述。所述固化特别是在环境温度进行。这典型地持续几天到几周的时间,直至在给定条件下很大程度完成。持续时间尤其取决于温度、成分的反应性和它们的化学计量以及促进剂的存在。
因此,本发明的另一主题还有经固化的组合物,它由如本文献所述的环氧树脂组合物固化获得。
所述环氧树脂组合物的施用在至少一个基材上进行,其中特别适合的是以下:
-玻璃、玻璃陶瓷、混凝土、灰浆、砖、瓦、石膏和天然石材如花岗岩或大理石;
-金属和合金,如铝、钢、铁和有色金属,包括表面精加工的金属和合金,如镀锌和镀铬的金属;
-皮革,织物,纸张,木材,与例如酚树脂、三聚氰胺树脂和环氧树脂粘合的木材材料,树脂-织物复合材料和其它所谓的聚合物复合材料;
-塑料,特别是硬质和软质PVC、ABS、聚碳酸酯(PC)、聚酰胺(PA)、聚酯、PMMA、环氧树脂、PUR、POM、PO、PE、PP、EPM和EPDM,其中所述塑料任选地借助于等离子体、电晕或火焰进行表面处理;
-纤维增强的塑料,如碳纤维增强的塑料(CFK)、玻璃纤维增强的塑料(GFK)和片状模塑复合物(SMC);
-经涂布的基材,如粉末涂布的金属或合金;
-涂料和油漆。
如果需要的话,可以在施加环氧树脂组合物之前对基材进行预处理。这样的预处理特别地包括物理和/或化学清洁方法,例如打磨、喷砂、喷丸处理、刷和/或吹等,以及另外采用清洁剂或溶剂或者施涂粘附促进剂、粘附促进剂溶液或底漆的处理。
所述环氧树脂组合物有利地可以用作纤维复合材料(复合物)、灌注材料、密封材料、粘合剂、覆盖物、涂层、涂漆、漆、密封剂、打底漆或底漆。特别是可以用作灌注材料、密封材料和粘合剂,例如电灌注材料(Elektrovergussmasse)、密封材料、车身粘合剂、夹芯板胶、半壳粘合剂,例如用于风力发电机的叶片、桥元件粘合剂或锚固粘合剂;另外还有作为建筑业和工业应用的覆盖物、涂层、涂漆、漆、密封剂、打底漆和底漆,特别是如用于室内例如办公室、厂房、体育馆或冷藏室的地面覆盖物和地面涂层,或者用在阳台、平台、停车场(Parkdecks)、桥梁或屋顶的户外区域中,作为混凝土、水泥、金属、塑料或木材的保护涂层,例如用于木质构造、车辆、装卸平台、油罐、筒仓、井、管线、管道、机械或钢铁结构的表面密封,例如船舶、码头、海上平台、闸门、水电站、河道工程、游泳池、风力发电机、桥梁、烟囱、起重机或板桩的表面密封;以及另外作为前涂漆、附着性涂漆、防腐底漆或用于表面疏水化。在用作涂层、覆盖物或涂漆时,在完全固化或部分固化的环氧树脂组合物上特别地还可以施加其它的涂层、其它的覆盖物或其它的涂漆,其中所述其它的层同样可以是环氧树脂组合物,但也可以是另一种材料,特别是聚氨酯涂层或聚脲涂层。
所述环氧树脂组合物可以特别有利地用作涂层。涂层在此应理解为所有类型的平面施涂的覆盖物,特别还有如之前所描述的涂漆、漆料、密封剂、打底漆或底漆。所述环氧树脂组合物可以特别有利地用在生态品质保证的低排放环氧树脂产品中,所述生态品质保证例如根据Emicode(EC1Plus)、AgBB、DIBt、蓝天使、AFSSET、RTS(M1)和美国绿色建筑协会(LEED)。
所述环氧树脂组合物作为涂层有利地用于涂布方法中,其中所述环氧树脂组合物具有低粘度和良好流平性的液体稠度(flüssigeKonsistenz),特别是可以作为自流平涂层施加到到大部分平坦的面上或作为涂漆施加。优选地,在树脂组分和固化剂组分混合之后直接施加的环氧树脂组合物在20℃时测量的粘度优选在300mPa·s至2000mPa·s的范围内,优选在300mPa·s至1500mPa·s的范围内,特别优选在300mPa·s至1200mPa·s的范围内。混合的组合物典型地在环境温度下,在处理时间内作为薄膜平面地施加到基材上,所述薄膜的层厚度典型地为约50μm至约5mm。特别是通过浇铸到待涂布的基材上,并随后借助于例如刮刀或锯齿抹子(Zahntraufel)均匀地分布来进行所述施加。但是所述施加还可以利用刷子或辊或者以喷涂进行,例如作为钢材上的防腐蚀涂层。
在固化所产生的典型地很大程度上澄清、有光泽和无粘性的高硬度膜时,所述膜的脆性低并且极其不易变黄,并且对不同基材具有良好附着。
高硬度和低脆性的膜优选硬度(依的摆测硬度,按照DIN EN ISO 1522测量)在100s至200s的范围内,特别是120s至180s的范围内。更高的硬度通常带来增加的脆性,更低的硬度对很多涂层应用来说太软。
本发明的另一主题是包含通过固化所述环氧树脂组合物获得的、经固化的组合物的制品。所述经固化的组合物在此特别呈涂层形式。
涂覆的环氧树脂组合物由于有利的性质而出众。它是低粘度的并且即使在湿冷条件也快速和最大程度固化而不出现雾浊效应,其中可以获得高硬度、低脆性和低变黄倾向的澄清的膜,即使使用少量的或完全不使用不可掺入的稀释剂和以少量或完全不使用相对挥发性的小分子伯二胺。利用所述环氧树脂组合物可以获得低排放的环氧树脂产品,它满足很多生态品质保证的条件,同时在工作安全、加工性质和使用性质方法满足高要求。
实施例
以下列出应进一步说明本发明的实施例。当然本发明并不局限于所述的实施例。
“AHEW”表示胺氢当量。
“EEW”表示环氧化物当量。
“MGC”表示“三菱气体化学”。
“GT”表示“重量份”。
1.测量方法的描述
胺含量,即所制备的化合物中氨基基团的总含量通过滴定法测定(利用在冰醋酸中的0.1N HClO4,相对于结晶紫),并且总是以mmolN/g给出。
红外光谱(FT-IR),以未稀释膜形式在配备具有ZnSe晶体的水平ATR测量单元的Perkin-Elmer的FT-IR仪器1600上测量;吸收谱带以波数(cm-1)表示(测量窗口:4000-650cm-1)
GC/MS,在下列条件下进行:柱Agilent VF-5ms,30m×0.25mm,0.25μm膜厚度;以15℃/min的加热速率从60℃加热至320℃,随后320℃保持15分钟;载气He,具有恒定流速1.1ml/min;25:1分流进样,温度为230℃;离子化方法Cl+(甲醇)。
粘度,在恒温的锥板式粘度计Rheotec RC30(锥直径50mm,锥角1°,锥尖-板间距0.05mm,剪切速率10至100s-1)上测量。
2.使用的物质:
EP-加合物1:116.0GT 1,5-二氨基-2-甲基戊烷和182GTDY-K的反应产物;AHEW=99.4g/Eq;粘度(20℃)=5,800mPa·s
EP-加合物2:136.2GT 1,3-双(氨基甲基)苯和182GTDY-K的反应产物;AHEW=106.1g/Eq;粘度(20℃)=28,100mPa·s
3442(Huntsman):苯烷基胺,AHEW=125g/Eq;粘度(20℃)=10,210mPa·s
240(MGC):苯乙烯化的1,3-双(氨基甲基)苯;AHEW=103g/Eq;粘度(20℃)=165mPa·s
RFD-270(Huntsman):来自1,4-二羟甲基环己烷的丙氧基化和随后胺化的、含醚基团的环脂族二胺;AHEW=67g/Eq
DY-K(Huntsman):甲酚的单缩水甘油醚;EEW约182g/Eq
GY 250(Huntsman):双酚-A-二缩水甘油醚;EEW约187.5g/Eq
DY-E(Huntsman):C12-至C14-醇的单缩水甘油醚;EEW约290g/Eq
K 54(Air Products):2,4,6-三(二甲基氨基甲基)酚
3.胺的制备
胺-1:1,3-双(2-乙基己基氨基甲基)苯
在圆底烧瓶中将25.6g(0.20mol)2-乙基己醛和13.6g(0.10mol)1,3-双(氨基甲基)苯(来自MGC)于氮气氛下溶于足够的异丙醇中。将溶液在室温搅拌30分钟,随后在80巴的氢气压力,80℃的温度和3ml/min的流速的条件下,在具有Pd/C-固定床催化剂的连续运转的氢化装置上氢化。出于反应控制目的,利用IR光谱检验在约1665cm-1时亚胺谱带是否消失。随后在80℃真空浓缩所述溶液。得到澄清的淡黄色液体,其在20℃时粘度为140mPa·s,胺含量为5.50mmol N/g,纯度为87.7%(借助气相色谱法测量),和理论AHEW为约180.3g/Eq。
FT-IR:2956,2923,2857,2811,1457,1378,1156,1113,776,726,699。
GC/MS:tR=15.56min;m/z=361.0([MH+];C24H44N2的理论质量:360.35)。
胺-2:包含1,3-双(2-乙基己基氨基甲基)苯和N-2-乙基己基-1,3-双(氨基甲基)苯的反应混合物
以与胺-1所述相同方式,使20.5g(0.16mol)2-乙基己醛和13.6g(0.10mol)1,3-双(氨基甲基)苯反应。得到澄清的、淡黄色液体,其在20℃时粘度为100mPa·s,胺含量为6.39mmol N/g,1,3-双(2-乙基己基氨基甲基)苯含量为66.4重量%,N-2-乙基己基-1,3-双(氨基甲基)苯含量为30.1重量%(借助气相色谱法测定),和理论AHEW为约130.2g/Eq。
胺-3(参照):1,3-双(苄基氨基甲基)苯
以与胺-1所述相同方式,使21.2g(0.20mol)苯甲醛和13.6g(0.10mol)1,3-双(氨基甲基)苯反应。得到澄清的、淡黄色液体,其在20℃时粘度为230mPa·s,胺含量为6.41mmol N/g,和理论AHEW为约158.2g/Eq。
胺-4(参照):1,3-双(2-甲基丙基氨基甲基)苯
以与胺-1所述相同方式,使14.4g(0.2mol)异丁醛和13.6g(0.1mol)1,3-双(氨基甲基)苯反应。得到澄清的、淡黄色液体,其在20℃时粘度为100mPa·s,胺含量为6.37mmol N/g,和理论AHEW为约124g/Eq。
胺-5(参照):1,3-双(正辛氨基甲基)苯
以与胺-1所述相同方式,使25.6g(0.20mol)1-辛醛和13.6g(0.10mol)1,3-双(氨基甲基)苯反应。得到澄清的、淡黄色液体,其在20℃时粘度为130mPa·s,胺含量为5.45mmol N/g,理论AHEW为约180.3g/Eq。
胺-6(参照):N,N’-双(2-乙基己基)-1,5-二氨基-2-甲基戊烷
以与胺-1所述相同方式,使25.6g(0.20mol)1-辛醛和11.6g(0.10mol)1,5-二氨基-2-甲基戊烷(Invista的A)反应。得到澄清的、淡黄色液体,其在20℃时粘度为140mPa·s,胺含量为5.80mmol N/g,理论AHEW为约170.3g/Eq。
4.固化剂的制备
对于每个实施例,将表1中给出的成分给定量(以重量份计)借助离心混合机(SpeedMixerTM DAC 150,FlackTek Inc.)混合。混合后1小时分别测定固化剂组合物的粘度。结果在表1中给出。
HZ-1至HZ-3是根据本发明的固化剂,Ref-1至Ref-3是对比实施例。
表1:固化剂HZ-1至HZ-3和Ref-1至Ref-3的组成、粘度和AHEW
表1的每种固化剂以这样的量包含胺-1和/或胺-3,使得它们的胺氢占固化剂中存在的胺氢总量的25%。
5.固化剂和环氧树脂组合物的制备
对于每个实施例,将表2至3中给出的成分以固化剂组分的给定量(以重量份计)借助离心混合机(SpeedMixerTM DAC 150,FlackTekInc.)混合,且远离潮湿存放。
同样处理和存放表2至3中给出的树脂组分的成分。
随后将每种组合物的两种组分借助离心混合机加工成均匀的液体,并立即如下所述进行检验:
混合后10分钟测定20℃时的粘度(“粘度(10’)”)。
在玻璃板上以500μm的层厚度施加第一膜,并将其存放在23±1℃和50±5%相对湿度下(=标准气候,以下缩写为“NK”),并且固化。在所述膜上在2天后(“硬度(2d NK)”)或4天后(“硬度(NK)(4d)”)或7天后(“硬度(7d NK)”)或4周后(“硬度(4w NK)”)测定硬度(根据DIN EN ISO 1522测量的根据的摆测硬度)。4周后评价膜的外观(表中以“外观(NK)”表示)。“美观”在此表示膜是澄清的,并且具有光泽和非粘性而没有结构的表面。“结构”在此表示表面上任何形式的图形或图案。
在玻璃板上以500μm的层厚度施加第二膜,将其在施用后的7天内直接存放在8℃和80%相对湿度下,并且随后在3周内存放在标准气候下,和/或固化。施用后24小时,在膜上放置聚丙烯瓶盖,瓶盖下放置湿海绵。另外24小时之后移除海绵和盖,放置在膜上新的位置上,然后24小时之后再移除并放置到新的位置,共计4次。随后评价该膜的外观(表1中以“外观(8°/80%)”表示),与外观(NK)所述方式相同。在此还分别给出标记物数目,通过湿海绵和/或其上放置的盖子在膜上可见。如果在标记物上出现变黄或混浊,同样给出。在这样固化的膜上测定硬度,分别在8℃和80%相对湿度下7天后测定(“硬度(7d冷)”),随后在NK下另外2天之后测定(“硬度(+2d NK)”)和/或在NK下另外7天之后测定(“硬度(+7d NK)”)和/或在NK下另外3周之后测定(“硬度(+3w NK)”)。
在如下面所述的膜上测定变黄,所述膜的层厚度为500μm、涂覆在玻璃板上、4周内在标准气候下固化,随后在光照良好的平台上放置3周。目视评价变黄的强度,并与被铝箔覆盖的膜的面比较。
在表2至3中给出结果。
EZ-1至EZ-4是根据本发明的实施例,Ref-4至Ref-11是对比实施例。
表2:EZ-1、EZ-2和Ref-4至Ref-8的组成和性质。
,,l.“表示,,轻微“;,,schw“表示,,弱“
240
表3:EZ-3、EZ-4和Ref-9至Ref-11的组成和性质。
“weiss”表示标记物出现白色雾浊;“schw.”表示“弱”
Claims (15)
1.式(I)的胺
2.用于制备根据权利要求1所述的胺的方法,通过1,3-双(氨基甲基)苯与2-乙基己醛和氢的还原烷基化反应进行。
3.根据权利要求1所述的胺作为稀释剂的用途,特别是环氧树脂的固化剂中的稀释剂的用途。
4.固化剂,它适用于环氧树脂的固化,所述固化剂包含根据权利要求1所述的式(I)的胺和至少一种多胺A,所述多胺A具有至少三个对环氧基团呈反应性的胺氢。
5.根据权利要求4所述的固化剂,其特征在于,所述多胺A选自1,5-二氨基-2-甲基戊烷、2-丁基-2-乙基-1,5-戊二胺、1,6-己二胺、2,2,4-和2,4,4-三甲基己二胺、1,12-十二烷二胺、1,3-二氨基环己烷、双(4-氨基环己基)甲烷、双(4-氨基-3-甲基环己基)甲烷、1-氨基-3-氨基甲基-3,5,5-三甲基环己烷、1,3-双(氨基甲基)环己烷、1,3-双(氨基甲基)苯、双六亚甲基三胺、二亚乙基三胺、三亚乙基四胺、四亚乙基五胺、五亚乙基六胺和线性聚亚乙基胺的更高级的同系物,例如具有5至7个亚乙基胺单元的聚亚乙基多胺、二亚丙基三胺、N-(2-氨基乙基)-1,3-丙二胺、N,N’-双(3-氨基丙基)乙二胺、由分子量在200g/mol至300g/mol的1,4-二羟甲基环己烷的丙氧基化和随后的胺化构成的含醚基团的环脂族二胺、分子量在200g/mol至500g/mol的聚氧亚烷基二胺和聚氧亚烷基三胺,以及呈与环氧化物的加合物形式的或呈迈克尔加合物、曼尼希碱或聚酰氨基胺形式的这些多胺的衍生物。
6.根据权利要求4或5所述的固化剂,其特征在于,所述多胺A是与环氧化物的加合物。
7.根据权利要求4至6中任一项所述的固化剂,其特征在于,所述多胺A是与芳族单环氧化物的加合物。
8.根据权利要求4至7中任一项所述的固化剂,其特征在于,所述式(I)的胺以这样的量存在,使得它的胺氢占固化剂中存在的胺氢总体的1%至75%。
9.根据权利要求4至8中任一项所述的固化剂,其特征在于,所述式(I)的胺以这样的量存在,使得它的重量份额占所有对环氧基团呈反应性的胺总和的1%至95%。
10.根据权利要求4至9中任一项所述的固化剂,其特征在于,不可掺入的稀释剂的含量低于25重量%。
11.环氧树脂组合物,其包含至少一种环氧树脂和根据权利要求4至10中任一项所述的固化剂。
12.根据权利要求11所述的环氧树脂组合物,其特征在于,所述环氧树脂是基于双酚的液体树脂。
13.根据权利要求11和/或12中任一项所述的环氧树脂组合物,其特征在于,所述环氧树脂组合物是双组分组合物且由下列物质构成:
(i)包含至少一种环氧树脂的树脂组分,和
(ii)包含根据权利要求4至10中任一项所述的固化剂的固化剂组分。
14.由根据权利要求11至13中任一项所述的组合物固化获得的经固化的组合物。
15.包含根据权利要求14所述的经固化的组合物的制品。
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AU2015303289B2 (en) * | 2014-08-13 | 2019-02-21 | Sika Technology Ag | Amine for low-emission epoxy resin compositions |
CN104829861A (zh) * | 2015-05-04 | 2015-08-12 | 林登科 | 促进剂、固化剂及稀释剂之配方方法与应用在消灭胺霜及胺浮油 |
EP3144335A1 (de) | 2015-09-17 | 2017-03-22 | Sika Technology AG | Amin für emissionsarme epoxidharz-zusammensetzungen |
ES2750306T3 (es) * | 2015-12-11 | 2020-03-25 | Univ California | Formulaciones de resina epoxídica latentes para procesos de impregnación de líquido para la producción de materiales compuestos fibrosos |
EP3205682A1 (de) | 2016-02-15 | 2017-08-16 | Sika Technology AG | Härter für emissionsarme epoxidharz-zusammensetzungen |
JP6447557B2 (ja) * | 2016-03-24 | 2019-01-09 | 日亜化学工業株式会社 | 発光装置の製造方法 |
EP3375803A1 (de) | 2017-03-14 | 2018-09-19 | Sika Technology Ag | Härter für emissionsarme epoxidharz-zusammensetzungen |
JP2020528101A (ja) | 2017-07-25 | 2020-09-17 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | エポキシ樹脂系内の反応性希釈剤としてのn,n’−ジアルキルメチルシクロヘキサンジアミン |
WO2019138059A1 (en) * | 2018-01-11 | 2019-07-18 | Holland Novochem Technical Coatings B.V. | Curing agent and coating composition |
US20210301077A1 (en) | 2018-10-01 | 2021-09-30 | Sika Technology Ag | Accelerator for curing epoxy resins comprising alkylated amines |
JP7437389B2 (ja) | 2018-10-01 | 2024-02-22 | シーカ テクノロジー アクチェンゲゼルシャフト | エポキシ樹脂用硬化剤 |
CN112789309B (zh) | 2018-10-01 | 2024-01-09 | Sika技术股份公司 | 用于环氧树脂胶粘剂的固化剂 |
JP2022501454A (ja) | 2018-10-01 | 2022-01-06 | シーカ テクノロジー アクチェンゲゼルシャフト | エポキシ樹脂用硬化剤 |
EP4119591A1 (de) | 2021-07-12 | 2023-01-18 | Sika Technology AG | Härter für epoxidharze |
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GB776805A (en) * | 1954-06-05 | 1957-06-12 | Bayer Ag | Process for the production of synthetic elastomers |
US3598782A (en) * | 1969-06-16 | 1971-08-10 | Firestone Tire & Rubber Co | Stabilization of butadiene-styrene copolymers with substituted xylylene diamines |
KR0158436B1 (ko) * | 1989-12-14 | 1998-12-01 | 피에르 오. 페론 | 개선된 수막염균성 폴리사카라이드 결합체 백신 |
US5426157A (en) | 1994-03-16 | 1995-06-20 | Air Products And Chemicals, Inc. | Flexibilized polyepoxide resins incorporating poly-N-methylated secondary amines |
US5739209A (en) | 1995-05-09 | 1998-04-14 | Air Products And Chemicals, Inc. | Amine curatives for flexibilized epoxies |
TW539661B (en) * | 2000-09-12 | 2003-07-01 | Mitsubishi Gas Chemical Co | Amino compound and process for producing the same |
US8512594B2 (en) * | 2008-08-25 | 2013-08-20 | Air Products And Chemicals, Inc. | Curing agent of N,N′-dimethyl-meta-xylylenediamine and multifunctional amin(s) |
-
2013
- 2013-01-08 EP EP13150534.9A patent/EP2752403A1/de not_active Withdrawn
- 2013-12-20 JP JP2015551166A patent/JP6335921B2/ja not_active Expired - Fee Related
- 2013-12-20 WO PCT/EP2013/077704 patent/WO2014108306A1/de active Application Filing
- 2013-12-20 CN CN201380065721.4A patent/CN104854077B/zh not_active Expired - Fee Related
- 2013-12-20 EP EP13811566.2A patent/EP2943464B1/de not_active Not-in-force
- 2013-12-20 AU AU2013372264A patent/AU2013372264A1/en not_active Abandoned
- 2013-12-20 ES ES13811566.2T patent/ES2625749T3/es active Active
- 2013-12-20 US US14/759,511 patent/US9580381B2/en active Active
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107922585A (zh) * | 2015-09-01 | 2018-04-17 | Sika技术股份公司 | 低排放环氧树脂组合物 |
CN109996784A (zh) * | 2016-11-29 | 2019-07-09 | 巴斯夫欧洲公司 | 用于稳定至少单烷基取代的二氨基环己烷的方法 |
Also Published As
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EP2943464A1 (de) | 2015-11-18 |
JP2016508144A (ja) | 2016-03-17 |
JP6335921B2 (ja) | 2018-05-30 |
EP2752403A1 (de) | 2014-07-09 |
WO2014108306A1 (de) | 2014-07-17 |
ES2625749T3 (es) | 2017-07-20 |
AU2013372264A1 (en) | 2015-06-18 |
CN104854077B (zh) | 2018-01-09 |
US9580381B2 (en) | 2017-02-28 |
US20150344406A1 (en) | 2015-12-03 |
EP2943464B1 (de) | 2017-03-01 |
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