CN107250229B - 具有高阻燃性的基于异氰酸酯的耐温泡沫 - Google Patents
具有高阻燃性的基于异氰酸酯的耐温泡沫 Download PDFInfo
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- CN107250229B CN107250229B CN201680010821.0A CN201680010821A CN107250229B CN 107250229 B CN107250229 B CN 107250229B CN 201680010821 A CN201680010821 A CN 201680010821A CN 107250229 B CN107250229 B CN 107250229B
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- isocyanate
- foam
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Abstract
本发明涉及具有高度阻燃性的耐温泡沫，使用可结合的催化剂以及使用甲酸作为发泡剂由芳族异氰酸酯和多环氧化物制备所述泡沫的方法，以及所述泡沫的用途。
Description
本发明涉及一种制备泡沫的方法和可通过该方法获得的泡沫，以及这些泡沫作为建筑领域中的填充泡沫或作为夹层构造的芯泡沫或用于制备结构材料或绝缘材料的用途，在所述方法中，将a)多异氰酸酯与b)至少一种具有至少两个环氧基的有机化合物、c)至少一种加速异氰酸酯/环氧化物反应的催化剂、d)含有甲酸的化学和/或物理发泡剂和e)任选的助剂和添加剂混合，以形成反应混合物，其中异氰酸酯基与环氧基的当量比为1.2:1至500:1，然后使该反应混合物反应成泡沫，其中所述加速异氰酸酯/环氧化物反应的催化剂包含至少一种选自如下的催化剂：双(二甲基氨基丙基)脲、双(N,N-二甲基氨基乙氧基乙基)氨基甲酸酯、二甲基氨基丙基脲、N,N,N-三甲基-N-羟基乙基双(氨基丙基醚)、N,N,N-三甲基-N-羟基乙基双(氨基乙基醚)、二乙基乙醇胺、双(N,N-二甲基-3-氨基丙基)胺、二甲基氨基丙胺、3-二甲基氨基丙基-N,N-二甲基丙烷-1,3-二胺、二甲基-2-(2-氨基乙氧基乙醇)和(1,3-双(二甲基氨基)-丙烷-2-醇)、N,N-双(3-二甲基氨基丙基)-N-异丙醇胺、双(二甲基氨基丙基)-2-羟基乙胺、N,N,N-三甲基-N-(3-氨基丙基)双(氨基乙基醚)、3-二甲基氨基异丙基-二异丙醇胺，或它们的混合物。
在早期研究中，US 3,793,236、US 4,129,695和US 3,242,108记载了由多异氰酸酯和多环氧化物制备泡沫。某种程度上，如在US 3,849,349中，还记载了添加另外的H-活性物质。
更近的现有技术记载了由有机多异氰酸酯和有机多环氧化物的反应混合物经由含有部分三聚的异氰脲酸酯基(＝中间体)的中间体优选制备这种泡沫，所述中间体通过阻聚剂稳定。在此情况下，耐高温泡沫通过如下过程获得：使有机多异氰酸酯、有机多环氧化物、催化剂和阻聚剂的反应混合物反应形成储存稳定的较高粘度的中间体(“预三聚”)，然后通过添加发泡剂和自发加速异氰酸酯/环氧化物反应的催化剂使该较高粘度中间体反应成为最终不再可熔的发泡终态。
EP 0 331 996和EP 0 272 563首先记载了添加具有烷基化作用的抑制剂作为阻聚剂来制备储存稳定的异氰酸酯/环氧化物混合物。DE 39 38 062 A1公开了由与具有烷基化作用的磺酸烷基酯混合的中间体作为阻聚剂来制备EPIC泡沫(环氧化物/异氰酸酯)。该文献记载了可使用任何有机多异氰酸酯作为异氰酸酯组分，尤其是二苯基甲烷系列的多异氰酸酯混合物。除2,4'-异构体外，作为优选述及的其他几种多异氰酸酯组分之一还可含有二苯基甲烷系列的其他异构的或同系的多异氰酸酯，以及10重量％至最高达60重量％的较高核(higher nuclear)多苯基多亚甲基多异氰酸酯，基于全部多异氰酸酯混合物计。
根据WO 2012/80185 A1和WO 2012/150201 A1，如果使用某些发泡剂制备EPIC泡沫，则由此制备的泡沫的质量可获得极大改善。根据这些文献的教导，EPIC泡沫的制备还优选在用作阻聚剂的稳定剂的存在下通过起始物料的反应来进行。优选使用的多异氰酸酯组分通常为2,4'-MDI与4,4'-MDI和任选地基于全部混合物计0至20重量％的2,2'-MDI的混合物，或这些异构体与较高核的聚合MDI(pMDI)的混合物，后者通常以10重量％至60重量％存在于混合物中，基于全部的多异氰酸酯混合物计。在实施例中，使用MDI类型的异构单体的混合物。
现有技术中记载的含有EPIC反应的反应产物且具有耐高温性的泡沫以其良好的机械性能和高温稳定性而为人所知。它们还具有与聚氨酯泡沫的可燃性相比降低的可燃性。然而，历经两阶段过程的制备方法颇为复杂。此外，必须使泡沫退火以获得良好的机械性能。最后，应当进一步改善泡沫在添加且特别是不添加阻燃剂的情况下的机械性能、尤其是耐火行为。
因此，本发明的目的是提供一种基于异氰酸酯和有机多环氧化物的耐高温泡沫，其制备容易快捷、具有优异的机械性能并且显示出低的可燃性。
本发明的目的通过一种可由如下方法获得的泡沫而实现：其中将a)多异氰酸酯与b)至少一种具有至少两个环氧基的有机化合物、c)至少一种加速异氰酸酯/环氧化物反应的催化剂、d)含有甲酸的化学和/或物理发泡剂和e)任选的助剂和添加剂混合，以形成反应混合物，其中异氰酸酯基与环氧基的当量比为1.2:1至500:1，然后使该反应混合物反应成泡沫，其中所述加速异氰酸酯/环氧化物反应的催化剂包含至少一种选自如下的催化剂：双(二甲基氨基丙基)脲、双(N,N-二甲基氨基乙氧基乙基)氨基甲酸酯、二甲基氨基丙基脲、N,N,N-三甲基-N-羟基乙基双(氨基丙基醚)、N,N,N-三甲基-N-羟基乙基双(氨基乙基醚)、二乙基乙醇胺、双(N,N-二甲基-3-氨基丙基)胺、二甲基氨基丙胺、3-二甲基氨基丙基-N,N-二甲基丙烷-1,3-二胺、二甲基-2-(2-氨基乙氧基乙醇)和(1,3-双(二甲基氨基)-丙烷-2-醇)、N,N-双(3-二甲基氨基丙基)-N-异丙醇胺、双(二甲基氨基丙基)-2-羟基乙胺、N,N,N-三甲基-N-(3-氨基丙基)双(氨基乙基醚)、3-二甲基氨基异丙基-二异丙醇胺，或它们的混合物。
本发明还涉及可发泡混合物在形成本发明的具有耐高温性的泡沫的发泡结束前用于粘接基底，用于粘接钢板、铝板和铜板、塑料片材和聚对苯二甲酸丁二醇酯片材的用途。
根据本发明的“多异氰酸酯(a)”意指每分子含有至少两个反应性异氰酸酯基的有机化合物，即其官能度至少为2。如果使用的多异氰酸酯或几种多异氰酸酯的混合物不具有统一的官能度，则所使用的组分a)的数均官能度至少为2。优选地，多异氰酸酯a)的平均异氰酸酯官能度至少为2.2，且更优选至少为2.4。组分a)的平均官能度为2.2至4，优选2.5至3.8，且更优选2.7至3.5。
优选地，组分a)中的异氰酸酯基的含量为5至10mmol/g，尤其是6至9mmol/g，更优选7至8.5mmol/g。技术人员知晓如下事实：异氰酸酯基以mmol/g计的含量与以g/当量计的所谓当量重量互为倒数关系。异氰酸酯基以mmol/g计的含量根据ASTM D-5155-96 A由以重量％计的含量获得。
使用的组分a)的粘度可在宽的范围内变化。优选地，组分a)根据DIN 53 018在25℃下的粘度为100至10,000mPa·s，更优选为200至2500mPa·s。
可考虑的多异氰酸酯a)包括本身已知的脂肪族、脂环族、芳脂族和优选地芳族的多价异氰酸酯。这样的多官能异氰酸酯是本身已知的，或可通过本身已知的方法制备。特别地，多官能异氰酸酯也可作为混合物来使用，因而在此情况下组分a)含有不同的多官能异氰酸酯。可用作多异氰酸酯的多官能异氰酸酯每分子具有两个(下文称作二异氰酸酯)或多于两个异氰酸酯基。
可详细地特别地提及的为：亚烷基基团中具有4至12个碳原子的亚烷基二异氰酸酯，如1,12-十二烷二异氰酸酯、2-乙基四亚甲基-1,4-二异氰酸酯、1,4,2-甲基五亚甲基-1,5-二异氰酸酯、四亚甲基-1,4-二异氰酸酯和优选的六亚甲基-1,6-二异氰酸酯；脂环族二异氰酸酯，如环己烷-1,3-和-1,4-二异氰酸酯及这些异构体的任何混合物，1-异氰酸酯基-3,3,5-三甲基-5-异氰酸酯基甲基环己烷(IPDI)，2,4-和2,6-六氢甲苯二异氰酸酯及相应的异构体混合物，4,4'-、2,2'-和2,4'-二环己基甲烷二异氰酸酯及相应的异构体混合物；以及优选的芳族多异氰酸酯，如2,4-和2,6-甲苯二异氰酸酯及相应的异构体混合物，4,4'-、2,4'-和2,2'-二苯基甲烷二异氰酸酯及相应的异构体混合物，4,4'-和2,2'-二苯基甲烷二异氰酸酯的混合物，多苯基多亚甲基多异氰酸酯，4,4'-、2,4'-和2,2'-二苯基甲烷二异氰酸酯和多苯基多亚甲基多异氰酸酯的混合物(粗MDI)，以及粗MDI和甲基二异氰酸酯的混合物。
特别合适的为：2,2'-、2,4'-和/或4,4'-二苯基甲烷二异氰酸酯(MDI)，1,5-萘二异氰酸酯(NDI)，2,4-和/或2,6-甲苯二异氰酸酯(TDI)，3,3'-二甲基二苯基二异氰酸酯，1,2-二苯基乙烷二异氰酸酯和/或对苯二异氰酸酯(PPDI)，三-、四-、五-、六-、七-和/或八亚甲基二异氰酸酯，2-甲基五亚甲基-1,5-二异氰酸酯，2-乙基亚丁基-1,4-二异氰酸酯，五亚甲基-1,5-二异氰酸酯，亚丁基-1,4-二异氰酸酯，1-异氰酸酯基-3,3,5-三甲基-5-异氰酸酯基甲基环己烷(异佛尔酮二异氰酸酯，IPDI)，1,4-和/或1,3-双(异氰酸酯基甲基)环己烷(HXDI)，1,4-环己烷二异氰酸酯，1-甲基-2,4-和/或-2,6-环己烷二异氰酸酯，以及4,4'-、2,4'-和/或2,2'-二环己基甲烷二异氰酸酯。
也常使用改性的多异氰酸酯，即通过有机多异氰酸酯的化学反应获得且每分子具有至少两个反应性异氰酸酯基的产物。具体地，可提及含有酯基、脲基、缩二脲基、脲基甲酸酯基、碳二亚胺基、异氰脲酸酯基、脲二酮基、氨基甲酸酯基和/或氨基甲酸乙酯基的多异氰酸酯，通常还连同未反应的多异氰酸酯一起。
更优选地，组分a)的多异氰酸酯含有2,2'-MDI或2,4'-MDI或4,4'-MDI，或由含有至少3个芳核且官能度至少为3的MDI较高核同系物构成的低聚MDI，或上述二苯基甲烷二异氰酸酯中的两种或三种的混合物，或在MDI的制备过程中获得的粗MDI，或优选地至少一种MDI低聚物和上述2,2'-MDI、2,4'-MDI或4,4'-MDI中的至少一种的混合物(也称作聚合MDI)。通常，MDI的异构体和同系物通过将粗MDI蒸馏而获得。
优选地，除两核的MDI外，聚合MDI还含有一种或多种官能度大于2、尤其是3或4或5的MDI的多核缩合产物。聚合MDI是已知的，并且常被称作多苯基多亚甲基多异氰酸酯。
含有聚合MDI的多异氰酸酯的(平均)官能度可在约2.2至约4、尤其是在2.5至3.8、且更特别地在2.7至3.5的范围内变化。这种具有不同官能度的基于MDI的多官能异氰酸酯的混合物特别地包括粗MDI，其在MDI的制备过程中作为中间产物获得。
基于MDI的多官能异氰酸酯或若干多官能异氰酸酯的混合物是已知的，并且例如由BASF Polyurethanes GmbH以商品名
M20或
M50出售。
优选地，组分(a)含有基于组分(a)的总重量计至少70重量％、更优选至少90重量％并且尤其是100重量％的一种或多种选自2,2'-MDI、2,4'-MDI、4,4'-MDI和MDI低聚物的异氰酸酯。低聚MDI的含量优选基于组分(a)的总重量计至少为50重量％、更优选大于60重量％并且尤其是至少为64重量％。
含有环氧基的组分b)为任何具有至少两个环氧基的脂肪族、脂环族、芳族和/或杂环化合物。优选适合作为组分b)的环氧化物每分子具有2至4个、优选2个环氧基，并且环氧当量重量为90至500g/eq、优选140至220g/eq。
合适的多环氧化物包括例如以下多价酚的多缩水甘油醚，例如：邻苯二酚、间苯二酚、对苯二酚、4,4'-二羟基二苯基丙烷(双酚A)、4,4'-二羟基-3,3'-二甲基二苯基甲烷、4,4'-二羟基二苯基甲烷(双酚F)、4,4'-二羟基二苯基环己烷、4,4'-二羟基-3,3'-二甲基二苯基丙烷、来自4,4'-二羟基二苯砜(双酚S)、的4,4'-二羟基二苯基、三(4-羟基苯基)甲烷、上述二酚的氯化和溴化产物、酚醛清漆(即来自单价或多价酚和/或甲酚与醛、尤其是甲醛在酸性催化剂的存在下以小于1:1的当量比的反应产物)、由2摩尔芳族羟基羧酸的钠盐与1摩尔二卤代烷或二卤代二烷基酯的酯化得到的二酚(参见英国专利1 017 612)，或由酚和含有至少两个卤素原子的长链卤代链烷烃的缩合得到的多酚(参见GB-PS 1 024 288)。此外，可提及：基于芳族胺和表氯醇的多环氧化合物，例如N-二(2,3-环氧丙基)苯胺、N,N'-二甲基-N,N'-二环氧丙基-4,4'-二氨基二苯基甲烷、N,N-二环氧丙基-4-氨基苯基缩水甘油醚(参见GB-PS 772 830和816 923)。
此外，可使用：多价芳族、脂肪族和脂环族羧酸的缩水甘油酯，例如邻苯二甲酸二缩水甘油酯、间苯二甲酸二缩水甘油酯、对苯二甲酸二缩水甘油酯、己二酸二缩水甘油酯，以及1摩尔芳族或脂环族二羧酸酐与1/2摩尔二醇或1/n摩尔带有n个羟基的多元醇的反应产物的缩水甘油酯，或六氢邻苯二甲酸二缩水甘油酯，其可任选被甲基取代。
还可使用以下多价醇的缩水甘油醚，例如1,4-丁二醇(
DY-D，Huntsman)、1,4-丁二醇、丙三醇、三羟甲基丙烷(
DY-T/CH，Huntsman)、季戊四醇和聚乙二醇。此外关注的是异氰脲酸三缩水甘油酯、N,N'-二环氧丙基羟基酰胺、诸如来自二巯基甲苯的多价硫醇的多缩水甘油基硫醚、二缩水甘油基三亚甲基三砜、基于乙内酰脲的多缩水甘油醚。
最后，还可使用多不饱和化合物如植物油及其转化产物的环氧化产物。也可使用：二烯烃或聚烯烃如丁二烯、乙烯基环己烷、1,5-环辛二烯、1,5,9-环十二烷三烯的环氧化产物；仍含有可环氧化的双键的聚合物和混合聚合物，例如基于聚丁二烯、聚异戊二烯、丁二烯-苯乙烯混合聚合物、二乙烯基苯、二环戊二烯、不饱和聚酯；可通过Diels-Alder加成获得且随后通过与每种化合物环氧化而转化成多环氧化物的烯烃的其他环氧化产物；或来自含有两个通过桥接原子或桥头原子基团连接的环戊烯环或环己烯环的化合物的其他环氧化产物。
此外，还可使用不饱和单环氧化物的聚合物，例如甲基丙烯酸缩水甘油酯或烯丙基缩水甘油醚的聚合物。
优选地，将以下多环氧化合物或其混合物用作本发明的组分b)：
多价酚，尤其是双酚A(
GY250，Huntsman；
0162，BakeliteAG；
Resin 162，Hexion Specialty Chemicals GmbH；Eurepox 710，BrenntagGmbH；
GY250，Huntsman，D.E.R.TM332，The Dow Chemical Company；
A18-00，LEUNA-Harze GmbH)或双酚F(4,4'-二羟基二苯基甲烷，
GY281，Huntsman；
F 16-01，LEUNA-Harze GmbH；
F 17-00，LEUNA-Harze GmbH)的多缩水甘油醚；基于芳族胺，尤其是双(N-环氧丙基)苯胺、N,N'-二甲基-N,N'-二环氧丙基-4,4'-二氨基二苯基甲烷和N,N-二环氧丙基-4-氨基苯基缩水甘油醚的多环氧化合物；脂环族二羧酸的多缩水甘油酯，尤其是六氢邻苯二甲酸二缩水甘油酯，以及来自n摩尔六氢邻苯二甲酸酐和1摩尔具有n个羟基(n＝2至6的整数)的多元醇、尤其是3摩尔六氢邻苯二甲酸酐和1摩尔1,1,1-三羟甲基丙烷的转化产物的多环氧化物；3,4-环氧环己基甲烷-3,4-环氧环己烷羧酸酯。
更特别优选双酚A和双酚F以及酚醛清漆的多缩水甘油醚，尤其是双酚F的多缩水甘油醚。
在特殊情况下，液态多环氧化物或低粘度二环氧化物如双(N-环氧丙基)苯胺或乙烯基环己烷二环氧化物可进一步降低已经为液态的多环氧化物的粘度，或将固态多环氧化物转化为液态混合物。
组分b)的用量对应于异氰酸酯基与环氧基的当量比为1.2:1至500:1、优选为3:1至65:1、尤其是3:1至30:1、更特别地为3:1至15:1。
催化剂c)强有力地加速具有环氧基的有机化合物(b)与有机的、任选改性的多异氰酸酯(a)的反应。催化剂(c)包括至少一种选自如下的可结合的(incorporated)胺催化剂：双(二甲基氨基丙基)脲、双(N,N-二甲基氨基乙氧基乙基)氨基甲酸酯、二甲基氨基丙基脲、N,N,N-三甲基-N-羟基乙基双(氨基丙基醚)、N,N,N-三甲基-N-羟基乙基双(氨基乙基醚)、二乙基乙醇胺、双(N,N-二甲基-3-氨基丙基)胺、二甲基氨基丙胺、3-二甲基氨基丙基-N,N-二甲基丙烷-1,3-二胺、二甲基-2-(2-氨基乙氧基乙醇)和(1,3-双(二甲基氨基)-丙烷-2-醇)、N,N-双(3-二甲基氨基丙基)-N-异丙醇胺、双(二甲基氨基丙基)-2-羟基乙胺、N,N,N-三甲基-N-(3-氨基丙基)双(氨基乙基醚)、3-二甲基氨基异丙基-二异丙醇胺，或它们的混合物。
除可结合的胺催化剂外，也可以使用还已知用于制备聚氨酯的其他常见的胺催化剂。例如，可以提及脒，如2,3-二甲基-3,4,5,6-四氢嘧啶；叔胺，如三乙胺、三丁胺、三亚乙基二胺、二甲基环己胺、二甲基辛胺、N,N-二甲基苄胺、N-甲基吗啉、N-乙基吗啉、N-环己基吗啉、N,N,N',N'-四甲基乙二胺、N,N,N',N'-四甲基丁二胺、N,N,N',N'-四甲基己二胺、五甲基二亚乙基三胺、四甲基二氨基乙醚、双(N,N-二甲基氨基乙基)醚、双(二甲基氨基丙基)脲、二甲基哌嗪、1,2-二甲基咪唑、1-氮杂双环[3.3.0]辛烷，以及优选的1,4-二氮杂双环[2.2.2]辛烷。同样合适的为，例如五甲基二亚乙基三胺、N-甲基-N'-二甲基氨基乙基哌嗪、N,N-二乙基乙醇胺和硅杂吗啉、三氯化硼-叔胺加合物，以及N-[3-(二甲基氨基)丙基]甲酰胺。
如果除可结合的胺催化剂外还使用其他催化剂，则其优选含有三氯化硼-叔胺加合物、N,N-二甲基苄胺和/或N,N-甲基二苄胺和/或三氯(N,N-二甲基辛胺)硼。
催化剂(c)作为催化剂或催化剂组合的使用浓度优选为0.001至8重量％、更优选0.6至6重量％、进一步优选1.5至5重量％并且尤其是2.1至5重量％，基于组分(a)、(b)和(c)的总重量计。具有异氰酸酯反应性基团的催化剂的比例至少为5重量％、更优选至少为8重量％并且尤其是8至25重量％，基于催化剂(c)计。
用于制备本发明的泡沫的化学和/或物理发泡剂(d)含有甲酸，任选与其他发泡剂混合。除甲酸和任选的水外，还可使用二乙氧膦酰硫胆碱氧化物(phospholine oxide)作为化学发泡剂。这些化学发泡剂与异氰酸酯基反应形成二氧化碳，或在甲酸的情况下形成二氧化碳和一氧化碳。由于这些发泡剂通过与异氰酸酯基的化学反应释放气体，因此它们被称作化学发泡剂。此外，可使用物理发泡剂如低沸点烃。特别合适的为这样的液体：其对多异氰酸酯a)呈惰性，并且具有在大气压下低于100℃、优选低于50℃的沸点，因而其在放热加聚反应的影响下会蒸发。优选使用的这种液体的实例包括：烷烃，如庚烷、己烷、正戊烷和异戊烷，优选正戊烷和异戊烷、正丁烷和异丁烷以及丙烷的工艺混合物；环烷烃，如环戊烷和/或环己烷；醚，如呋喃、二甲醚和二乙醚；酮，如丙酮和甲基乙基酮；羧酸烷基酯，如甲酸甲酯、草酸二甲酯和乙酸乙酯；以及卤代烃，如二氯甲烷、二氯一氟甲烷、二氟甲烷、三氟甲烷、二氟乙烷、四氟乙烷、氯二氟乙烷、1,1-二氯-2,2,2-三氟乙烷、2,2-二氯-2-氟乙烷、五氟丙烷、七氟丙烷和六氟丁烯。也可使用这些低沸点液体彼此的混合物或与其他取代或未取代的烃的混合物。其他合适的为有机羧酸，如甲酸、乙酸、草酸、蓖麻油酸和含有羧基的化合物。优选地，物理发泡剂可溶于组分(b)中。
优选地，使用小于2重量％、更优选小于1重量％、更优选小于0.5重量％并且尤其是不使用卤代烃作为所述发泡剂(d)。所述重量比例皆涉及组分(a)至(e)的总重量。优选地，使用水、甲酸/水混合物或甲酸作为化学发泡剂，更优选化学发泡剂包括甲酸/水混合物或甲酸。优选地，使用戊烷异构体或戊烷异构体的混合物作为物理发泡剂。
化学发泡剂可单独使用(即不加入物理发泡剂)或与物理发泡剂一起使用。优选地，化学发泡剂单独使用。如果将化学发泡剂与物理发泡剂一起使用，则优选将纯水、甲酸/水混合物或纯甲酸与戊烷异构体或戊烷异构体的混合物一起使用。在一个特别优选的实施方案中，甲酸为唯一的发泡剂。
作为所述助剂和添加剂(e)，可使用例如含有羟基或氨基的多官能化合物e1)，其包含具有至少2个、尤其是2至8个且优选2至3个醇羟基且分子量为62至8000g/mol的化合物e1-i)。这种化合物本身已知为聚氨酯的结构性组分，并且包括低分子量增链剂和数均分子量大于200g/mol的多元醇。增链剂的实例包括：简单的多元醇，如乙二醇、1,6-己二醇、丙三醇或三羟甲基丙烷，多元醇的实例包括具有二甲基硅氧烷部分的多元醇，例如双(二甲基羟基甲基甲硅烷基)醚；具有酯基的多羟基化合物，如蓖麻油或多羟基聚酯，其可通过过量的刚刚以示例性方式提及的那类简单多价醇与优选的二元羧酸或其酸酐(如己二酸、邻苯二甲酸或邻苯二甲酸酐)的缩聚而获得；多羟基聚醚，其可通过环氧烷烃(如环氧丙烷和/或环氧乙烷)与合适的起始分子(如水、上文刚刚提及的简单醇，或甚至具有至少两个胺的NH键合的胺)的加成反应而获得；或聚碳酸酯多元醇，其可例如由多元醇和碳酸酯或碳酰氯获得。
此外，化合物e1)也可为具有至少两个异氰酸酯反应性氢原子的化合物e1-ii)，所述两个异氰酸酯反应性氢原子中的至少一个属于伯氨基或仲氨基。其包括聚醚胺和分子量小于500g/mol且具有两个氨基的化合物。聚醚胺由聚氨酯化学已知，且可通过聚醚多元醇的端氨基化而获得。其分子量优选为500至8000g/mol。优选使用具有两个氨基且分子量小于500g/mol的化合物，更优选具有58至300g/mol、尤其是100至200g/mol的分子量。这些化合物优选具有两个伯氨基作为所述异氰酸酯反应性基团。在一个特别优选的实施方案中，伯氨基连接至芳族烃，优选连接至芳族六元环，尤其是间位或对位上。具体地，使用二亚乙基甲苯二胺(DETDA)、尤其是DETDA 80作为所述化合物e1-ii)。二亚乙基甲苯二胺是市售可得的，例如购自Lonza或Albemarle。
如果使用具有两个氨基且分子量小于500g/mol的化合物，则优选以0.1至5重量％、更优选0.5至2重量％来完成，基于化合物(a)和(b)的总重量计。
如果有的话，包括添加剂e1)的最大含量对应于NCO/OH当量比至少为2:1、优选至少为7:1并且尤其是至少为10:1，基于组分a)的异氰酸酯基和组分e1)的羟基和/或氨基计。在任何比率下，组分a)的量必须使得组分a)的异氰酸酯基与组分b)的环氧基、组分e1)的羟基和/或氨基以及组分b)中可能存在的羟基的总和的当量比至少为1.2:1、优选3:1至65:1、尤其是3:1至30:1、更优选3:1至15:1。
组分e1)中所有含羟基和/或脲基的化合物(优选多元醇和聚醚胺)的重量与环氧组分b)的重量之比优选小于30:70，其优选至多为28:72、更优选至多为25:75、甚至更优选为0-20:80-100。
本发明的EPIC泡沫优选含有小重量比例的源自多异氰酸酯a)与组分(e)的反应的氨基甲酸乙酯基和/或脲基。由多异氰酸酯a)与组分e)的羟基和/或脲基反应得到的氨基甲酸乙酯基和/或脲基的含量优选低于6重量％、优选低于5重量％、更优选低于4重量％、甚至更优选低于3重量％，基于组分的总重量计。在一个实施方案中，EPIC泡沫不含任何由多异氰酸酯a)与组分e)的反应得到的氨基甲酸乙酯基和/或脲基。
优选地，反应混合物含有基于组分b)和e1)的总重量计小于28重量％、更优选小于25重量％的组分e1)的含羟基和/或氨基的化合物，并且EPIC泡沫含有基于泡沫的总重量计小于6重量％、优选小于5重量％的源自多异氰酸酯a)与组分e)的反应的氨基甲酸乙酯基和/或脲基。
更优选地，反应混合物含有基于组分b)和多元醇和/或聚醚胺的总重量计小于28重量％、优选小于25重量％的多元醇和/或聚醚胺，并且EPIC泡沫含有基于泡沫的总重量计小于6重量％、优选小于5重量％的源自多异氰酸酯a)与组分e)的反应的氨基甲酸乙酯基和/或脲基。
可任选包含的其他助剂和添加剂e2)为可聚合的烯属不饱和单体，其用量最高可达100重量％、优选最高达50重量％、尤其最高达30重量％，基于组分a)和b)的总重量计。添加剂e2)的典型实例包括不具有对NCO基团呈反应性的氢原子的烯属不饱和单体，例如：二异丁烯、苯乙烯、C1-C4-烷基苯乙烯(如α-甲基苯乙烯、α-丁基苯乙烯)、氯乙烯、乙酸乙烯酯、马来酰亚胺衍生物(如双(4-马来酰亚胺基苯基)甲烷)、丙烯酸C1-C8-烷基酯(如丙烯酸甲酯、丙烯酸丁酯或丙烯酸辛酯)、相应的甲基丙烯酸酯、丙烯腈或邻苯二甲酸二烯丙酯。也可使用这些烯属不饱和单体的任何混合物。优选地，如果使用添加剂e2)，则采用苯乙烯和/或(甲基)丙烯酸C1-C4-烷基酯。
如果包含添加剂e2)，则可包括常规的聚合引发剂如过氧化苯甲酰，但通常不需要。
通常不需要包含助剂和添加剂e1)或e2)。顺便述及，e1-i)中尤其是e1-ii)中以实例的方式提及的添加剂，比e2)中以实例的方式提及的化合物更为优选。原则上，也可同时包含所有三种类型的助剂和添加剂。
可任选包括的其他助剂和添加剂e)为例如e3)填料，如石英粉、白垩、白云石、矾土、碳化硅、石墨或刚玉；颜料，如二氧化钛、氧化铁或有机颜料如酞菁颜料；增塑剂，如邻苯二甲酸二辛酯、磷酸三丁酯或磷酸三苯酯；可结合的增容剂，如甲基丙烯酸、β-羟基丙酯、马来酸酯和富马酸酯；改善阻燃性的物质，如红磷或氧化镁；可溶性染料或增强材料，如玻璃纤维或玻璃织物。还合适的为碳纤维或碳纤维织物，以及其他有机聚合物纤维如芳族聚酰胺纤维或LC聚合物纤维(LC＝“液晶”)。此外，可考虑将金属填料用作填料，如铝、铜、铁和/或钢。特别地，金属填料以颗粒形式和/或粉末形式使用。
可任选包含的其他助剂和添加剂e)为例如e4)具有对NCO基团呈反应性的氢原子的烯属不饱和单体，如甲基丙烯酸羟乙酯、甲基丙烯酸羟丙酯和甲基丙烯酸氨基乙酯。
此外，助剂和添加剂e)可含有e5)已知的聚醚硅氧烷类型的泡沫稳定剂；脱模剂，例如聚酰胺蜡和/或硬脂酸衍生物；和/或天然蜡，例如巴西棕榈蜡。
助剂和添加剂e)可在进行本发明的方法前纳入起始物料a)和b)中，或可随后与它们混合。
优选地，包含的助剂和添加剂e)的最大含量仅为使得NCO/OH当量比为2:1、优选至少为7:1、并且更优选至少为10:1，基于组分a)的异氰酸酯基和组分e)的羟基和/或氨基计。
为进行本发明的方法，可将起始物料a)和b)彼此混合。然后，将任选地其他助剂和添加剂e)、催化剂c)和发泡剂d)加入到反应混合物中，彻底混合所有物料，并将可发泡混合物浇铸至敞式模具或封闭模具中。
当使用由聚氨酯加工已知的多组分混料头时，所述方法具有高灵活性的特征。通过改变组分a)和b)的混合比，可使用相同的起始物料制备不同质量的泡沫。此外，也可将不同的组分a)和不同的组分b)以不同比例供给至混料头。可将助剂和添加剂e)、催化剂c)和发泡剂d)分别地或作为一批批料供给至混料头。还可将助剂和添加剂e)连同催化剂c)一起计量，且可单独计量发泡剂d)。通过改变发泡剂的量，可制备具有不同堆积密度范围的泡沫。
优选地，组分的混合在一个步骤中(所谓的“一步”法)进行。更优选地，反应应当在无预先三聚的步骤的情况下进行。制备过程可连续或不连续地进行。
根据使用的组分，发泡过程通常在2秒钟至4分钟的等待时间后开始，并且通常在2分钟至8分钟后结束。泡沫具有微小的孔并且均匀。
根据本发明，无需对泡沫进行后续的温度处理。在优选的实施方案中，不使泡沫退火。
在另一个实施方案中，在发泡成最终的发泡状态后，在70至250℃、优选120至250℃、更优选180至220℃下进行后续的温度处理。
当使用闭式模具制备本发明的泡沫时(模具发泡)，将模具过度填充(overfill)以实现最优的性能可能是有利的。“过度填充”意指填入一定量的可发泡混合物，其相当于在敞式模具中在发泡结束后其会占据比模具内部容积更大的体积。
本发明的泡沫具有低的导热性、非常好的机械性能(如高压缩强度)和在压缩下高的强性模量。此外，根据本发明的泡沫不易燃，并且在燃烧时仅产生少量的热和烟。其具有低的介电损耗，耐湿性和耐磨性以及模具加工性是优异的。因此，根据本发明的泡沫非常适合作为中空空间填充泡沫，作为电绝缘层的填充泡沫，作为夹层构造的芯，用于制备用于各种内部和外部应用的结构材料，用于制备车、船、飞机和火箭构造的结构材料，用于制备飞机内部和外部结构件，用于制备各种绝缘材料，用于制备绝缘板、绝缘管和容器绝缘材料，用于制备吸音材料，用于在机舱中使用，用于制备砂轮，以及用于制备高温绝缘材料和不易燃绝缘材料。
将通过以下实施例，对本发明作进一步说明。
实施例
在以下实施例中，所有百分比均按重量计。
除非另外明确说明，所有的量和测量值均涉及后续未在高温下储存(退火)的情况下制备的泡沫。
压缩强度的测量按照ISO 844EN进行。
堆积密度的测量按照DIN EN ISO 845进行。
热导率按照DIN 52612-2在10℃的温度下测定。
最大平均放热速率(MARHE)的测量按照ISO 5660-1进行。每占用表面的烟生成总量(TSP)的测量按照ISO 5660-2进行。所有试验使用50kW/m2的辐射热通量密度在尺寸为100mm×100mm×20mm的试验样本上进行。
可燃性和火焰蔓延按照根据DIN 4102-1的B2级建筑材料的要求测定。
固化时间定义为，搅拌开始与用棒接触泡沫表面时不再观察到粘合作用的时间之间的期间。
根据本发明，所有实施例以500±10g的起始物料总量制备。泡沫在体积为10升的纸板杯中发泡。
使用以下起始物料：
异氰酸酯：
A0：60重量％的2,4'-二异氰酸酯基二苯基甲烷和40重量％的4,4'-二异氰酸酯基二苯基甲烷的混合物。
A1：约40重量％的单体MDI和约60重量％的低聚MDI的混合物，平均官能度为约2.7，根据ASTM D 5199-96A的异氰酸酯含量为31.5g/100g，根据DIN 53 018在25℃下的粘度为210mPa·s。
A2：约30重量％的单体MDI和70重量％的低聚MDI的混合物，平均官能度为约2.8，根据ASTM D 5199-96A的异氰酸酯含量为31.5g/100g，根据DIN 53 018在25℃下的粘度为550mPa·s。
A3：约25重量％的单体MDI和75重量％的低聚MDI的混合物，平均官能度为约2.9，根据ASTM D 5199-96A的异氰酸酯含量为31g/100g，根据DIN 53 018在25℃下的粘度为2200mPa·s。
A4：为制备A4，将A2进料，并通过表面积为0.06m2的短程蒸发器在0.05mbar的压力和175℃的油浴温度下蒸发沸点最低的组分，二异氰酸酯基二苯基甲烷的异构体。在这样的条件下，物料平衡显示蒸发了供给量的25至27重量％。
将由此获得的底部产物A4通过HPLC进行分析，其中测定平均分子量为527g/mol且多分散性为1.7。此外，测定单体MDI的含量为12重量％。使用板直径为25mm的板-板式流变仪测定所得产物的粘度，其在25℃的温度下为8000mPa·s。在不进行进一步纯化步骤下使用该蒸馏产物。
A5：约35重量％的单体MDI和65重量％的聚合MDI的混合物，官能度为约f＝3.19，异氰酸酯含量为30.5至32％，根据DIN 53 019在25℃下的粘度为610至750mPa·s。
环氧化物：
B0：双酚A的二缩水甘油醚，Ruetapox 0162，Bakelite AG商品；Duisburg/德国，环氧指数：5.8-6.1eq/kg，环氧当量为167-171g/eq，在25℃下的粘度为4000至5000mPa·s。
B1：双酚A的二缩水甘油醚，购自The Dow Chemical Company(USA)的商品D.E.R.TM332，根据ASTM D-1652的环氧当量为171-175g/eq，根据ASTM D-445在25℃下的粘度为4000至6000mPa·s。
B2：Leuna
A 18-00，基于双酚A的低分子量环氧树脂，LEUNA-Harze GmbH(Leuna/德国)的商品，根据DIN 16 945环氧当量为175-185g/eq，根据DIN 53 015在25℃下的粘度为8000至10,000mPa·s。
B3：Leuna
F 16-01，基于双酚F的低分子量环氧树脂，LEUNA-Harze GmbH(Leuna/德国)的商品，根据DIN 16 945环氧当量为157-167g/eq，根据DIN 53 015在25℃下的粘度为1200至1600mPa·s。
B4：Leuna
F 17-00，基于双酚F的低分子量环氧树脂，LEUNA-Harze GmbH(Leuna/德国)的商品，根据DIN 16 945环氧当量为165-173g/eq，根据DIN 53 015在25℃下的粘度为2500至4500mPa·s。
C催化剂
C0 Addocat 3144：N-[3-(二甲基氨基)丙基]甲酰胺，Rheinchemie(Mannheim/德国)的商品
C1 Accelerator DY 9577：三氯化硼-胺络合物，热潜性催化剂，Huntsman(Bad
，德国)的商品
C2 N,N-甲基二苄胺，CAS号102-05-06，可自Sigma-Aldrich/德国获得
C3 N,N-二甲基苄胺，98％，CAS号103-83-3，可自Sigma-Aldrich/德国获得
C4 Dabco-T：N,N,N'-三甲基氨基乙基乙醇胺，Air Products and Chemicals(Allentown PA，USA)的商品
C5 Jeffcat ZF-10：N,N,N-三甲基-N-羟基乙基双(氨基乙醚)，Huntsman(Bad
，德国)的商品
C6 Jeffcat ZF-50：N,N-双(3-二甲基氨基丙基)-N-异丙醇胺，Huntsman(Bad
，德国)的商品
C7 Lupragen N 101：2-二甲基氨基乙醇，BASF SE(Ludwigshafen，德国)的商品
C8 Lupragen N 107：二甲基-2-(2-氨基乙氧基)乙醇，BASF SE(Ludwigshafen，德国)的商品
C9
TMR-30：2,4,6-三(二甲基氨基甲基)苯酚催化剂，购自Air Products公司
D发泡剂
D0甲酸(98-100％)，CAS号64-18-6，可自KMF Laborchemie(Lohmar/德国)获得，
D1 85重量％的甲酸(CAS号64-18-6)于水中
D2水
D3 Solkane 365/227：作为泡沫用发泡剂的液态氢氟烃，五氟丁烷(87重量％)与七氟丙烷(13重量％)的混合物，可自Solvay Fluor GmbH(Hannover，德国)获得
D4
3000：作为泡沫用发泡剂的液态氢氟烃：五氟丁烷，可自HoneywellInternational Inc.(Buffalo，USA)获得
D5环戊烷，CAS号287-92-3
D6 
1100：作为泡沫用发泡剂的液态氢氟烃：六氟丁烯，可自DuPontde Nemours(Germany)GmbH(Neu Isenburg，德国)获得
D7 Solkane R 141b：1,1-二氯-1-氟乙烷
E添加剂
E1对甲苯磺酸甲酯：CAS号80-48-8，可自Merck KGaA Darmstadt/Germany购得
E2 Desmophen 3600Z：聚醚多元醇，OH值为56mg KOH/g，f＝2，通过1,2-丙二醇的丙氧基化制备：Bayer MaterialScience(Leverkusen，德国)的商品
E3 Tegostab B 8411：聚醚聚硅氧烷，Evonik(Essen，德国)的商品
E4 Tegostab B 8485：聚醚聚硅氧烷，Evonik(Essen，德国)的商品
E5 DETDA 80：二乙基甲苯二胺，CAS号68479-98-1，可自Lonza(Basel，瑞士)获得
E6 
DC 193：硅酮表面活性剂，购自Air Products公司
实施例1
(对比，EPIC反应树脂制备，预先三聚成中间体)
在50℃下，将800g异氰酸酯A0与200g环氧化物B0和0.1ml C3混合，然后在120℃下加热。轻微放热的反应表明立即开始形成异氰脲酸酯。在无外部加热下反应2小时后，将进料冷却。这导致内部温度为约90℃。自进料中取样。样品的NCO含量为23％NCO。通过加入1.07g E1来淬灭反应。接下来，将进料在120℃下再搅拌30分钟。形成黄色澄清的储存稳定的树脂(中间体)，其在20℃下为液态，在25℃下的粘度为2080mPa·s，NCO含量为21.4％。
实施例2a(对比)
借助快速搅拌器，使400g实施例1的树脂掺入空气2分钟。在搅拌下，加入17.6gE2、7.0g E3和3.5g C0。其后，即刻加入6.0g D0，并将反应混合物再彻底混合10秒钟。将反应混合物浇铸至尺寸为20cm×20cm×24cm的纸板盒中，并使该反应混合物在所述纸板盒中发泡。将泡沫在200℃下退火3小时。
由此获得的泡沫的堆积密度为39kg/m3，压缩强度为0.246N/mm2。根据DIN 4102-1，该泡沫满足B2级建筑材料的要求。该泡沫的MARHE值为120kW/m2，烟生成总量为920m2/m2。
实施例2b(对比)
借助快速搅拌器，使400g实施例1的树脂掺入空气2分钟。在搅拌下，加入17.6gE2、7.0g E3和3.5g C0。其后，即刻加入6.0g D0，并将反应混合物再彻底混合10秒钟。将反应混合物浇铸至尺寸为20cm×20cm×24cm的纸板盒中，并使该反应混合物在所述纸板盒中发泡。
由此获得的泡沫的堆积密度为39kg/m3，压缩强度为0.296N/mm2。根据DIN 4102-1，该泡沫不满足B2级建筑材料的要求。该泡沫的MARHE值为132kW/m2，烟生成总量为761m2/m2。
实施例3
借助快速搅拌器，在1000rpm下将异氰酸酯和环氧树脂一起混合20秒至30秒。加入化学发泡剂，并在1000rpm下混入10秒。然后加入物理发泡剂并在200rpm下混合直至得到均匀混合物。其后，加入催化剂，并在2000rpm下混合3秒。
起始物质的精确组成以及所获得泡沫的机械值和耐火试验结果述于表1中。
表1：
泡沫配方的组分和物理特性。所有的量均以重量％表述。
实施例4
根据实施例3中所述的发泡方法，制备基于环氧组分B4的泡沫。起始物质的精确组成以及机械值和耐火试验结果述于表2中。
表2：
泡沫配方的组分和物理特性。配方中所有的量均以重量％表述。
实施例5
根据实施例3中所述的发泡方法制备泡沫，其中改变发泡剂。在实施例V5.7和V5.8中，不使用可结合的催化剂。在实施例V5.9中，使用具有少量反应性芳族OH基的催化剂。起始物质的精确组成以及机械值和耐火试验结果述于表3中。
表3：
泡沫配方的组分和物理特性。配方中所有的量均以重量％表述。
表3中的实施例示出，通过使用本发明的可结合的催化剂可显著改善耐火性能，同时在其他方面机械性能相似。具体而言，本发明的泡沫的MARHE值明显下降。
实施例6
根据实施例3中所述的发泡方法制备泡沫，其中在实施例6.1至6.5中仅使用反应性催化剂。
与之相比，当使用含有非反应性组分的催化剂包(6.6)时，泡沫的固化时间变得非常长。因此，泡沫经过非常长的时间仍保持粘性，并且在发泡后具有强度过低的特征，这对于处理而言是非常不利的。
表4：
泡沫配方的组分和物理特性。配方中所有的量均以重量％表述。
Claims (19)
1.一种制备泡沫的方法，其中
将a)多异氰酸酯与
b)至少一种具有至少两个环氧基的有机化合物，
c)至少一种加速异氰酸酯/环氧化物反应的催化剂，
d)含有甲酸的化学和/或物理发泡剂，和
e)任选的助剂和添加剂混合，
以形成反应混合物，其中异氰酸酯基与环氧基的当量比为1.2:1至500:1，然后使该反应混合物反应成泡沫，其中所述多异氰酸酯(a)的平均官能度为2.7至3.5，所述加速异氰酸酯/环氧化物反应的催化剂(c)包括至少一种选自如下的催化剂：N,N,N-三甲基-N-羟基乙基双(氨基乙基醚)、二甲基-2-(2-氨基乙氧基乙醇)、N,N-双(3-二甲基氨基丙基)-N-异丙醇胺、N,N,N’-三甲基氨基乙基乙醇胺、2-二甲基氨基乙醇，或它们的混合物。
2.根据权利要求1的制备泡沫的方法，其特征在于所述异氰酸酯a)包括2,2'-MDI或2,4'-MDI或4,4'-MDI，或低聚MDI，或所述2,2'-MDI、2,4'-MDI和4,4'-MDI中的两种或三种的混合物，或粗MDI，或至少一种MDI低聚物与所述2,2'-MDI、2,4'-MDI或4,4'-MDI中的至少一种的混合物。
3.根据权利要求2的制备泡沫的方法，其特征在于所述异氰酸酯a)包括至少一种MDI低聚物与所述2,2'-MDI、2,4'-MDI或4,4'-MDI中的至少一种的混合物。
4.根据权利要求3的制备泡沫的方法，其特征在于所述低聚MDI的含量大于60重量％，基于组分(a)的总重量计。
5.根据权利要求1至4中任一项的制备泡沫的方法，其特征在于所述具有至少两个环氧基的有机化合物选自双酚A、双酚F或酚醛清漆的多缩水甘油醚，或它们的混合物。
6.根据权利要求1至4中任一项的制备泡沫的方法，其特征在于除具有至少一个异氰酸酯反应性氢原子的催化剂外，所述加速异氰酸酯/环氧化物反应的催化剂(c)还包括至少一种其他胺催化剂。
7.根据权利要求6的制备泡沫的方法，其特征在于所述其他胺催化剂选自三氯化硼-叔胺加合物、N,N-二甲基苄胺、N,N-甲基二苄胺以及它们的混合物。
8.根据权利要求1至4中任一项的制备泡沫的方法，其特征在于所述催化剂(c)的用量为2.1至5重量％，基于组分(a)、(b)和(c)的总重量计。
9.根据权利要求1至4中任一项的制备泡沫的方法，其特征在于所述发泡剂(d)不含任何卤代烃。
10.根据权利要求1至4中任一项的制备泡沫的方法，其特征在于所述添加剂e)包含具有至少两个异氰酸酯反应性氢原子并且分子量小于500g/mol的化合物e1-ii)，其中所述异氰酸酯反应性氢原子中的至少一个属于伯氨基或仲氨基。
11.可通过权利要求1至10中任一项的方法获得的泡沫。
12.根据权利要求11的泡沫作为中空空间的填充泡沫，作为电绝缘层的填充泡沫，作为夹层构造的芯，用于制备内部和外部应用的结构材料，用于制备绝缘材料和用于制备吸音材料的用途。
13.根据权利要求11的泡沫用于制备车、船、飞机和火箭构造的结构材料的用途。
14.根据权利要求11的泡沫用于制备飞机内部和外部结构件的用途。
15.根据权利要求11的泡沫用于制备绝缘板、绝缘管和容器绝缘材料的用途。
16.根据权利要求11的泡沫用在发动机舱室中和用于制备砂轮的用途。
17.根据权利要求11的泡沫用于制备高温绝缘材料和不易燃绝缘材料的用途。
18.根据权利要求1至10中任一项的制备泡沫的方法中所述的反应混合物在形成所述泡沫的发泡结束前用于粘接基底，用于粘接钢板、铝板和铜板、塑料片材的用途。
19.根据权利要求18所述的用途，其中所述塑料片材为聚对苯二甲酸丁二醇酯片材。
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| WO2020160206A1 (en) * | 2019-01-31 | 2020-08-06 | Dow Global Technologies Llc | Isocyanate reactive compositions |
| BR112024001164A2 (pt) | 2021-07-22 | 2024-04-30 | Basf Se | Processo para produzir uma espuma híbrida de isocianato-epóxi, espuma híbrida de isocianato-epóxi e elemento sanduíche |
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2015
- 2015-02-20 EP EP15155888.9A patent/EP3059270A1/de not_active Withdrawn
-
2016
- 2016-02-17 HU HUE16704673A patent/HUE056812T2/hu unknown
- 2016-02-17 PT PT167046739T patent/PT3259293T/pt unknown
- 2016-02-17 US US15/551,779 patent/US20180066100A1/en not_active Abandoned
- 2016-02-17 PL PL16704673T patent/PL3259293T3/pl unknown
- 2016-02-17 CN CN201680010821.0A patent/CN107250229B/zh active Active
- 2016-02-17 EP EP16704673.9A patent/EP3259293B1/de active Active
- 2016-02-17 ES ES16704673T patent/ES2894100T3/es active Active
- 2016-02-17 WO PCT/EP2016/053371 patent/WO2016131874A1/de active Application Filing
- 2016-02-17 RS RS20211288A patent/RS62467B1/sr unknown
Patent Citations (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3849349A (en) * | 1971-05-12 | 1974-11-19 | K Frisch | Polyisocyanurate foam and process for producing the same |
| DE3713771A1 (de) * | 1986-04-25 | 1987-10-29 | Olin Corp | Oxazolidon-modifizierter isocyanurat-schaumstoff, verfahren zu seiner herstellung und seine verwendung |
| DE3824685A1 (de) * | 1987-08-03 | 1989-02-16 | Olin Corp | Schaeumbare zusammensetzung zur herstellung eines starren, urethanhaltigen und mit oxazolidon modifizierten isocyanuratschaums |
| DE4104199A1 (de) * | 1991-02-12 | 1992-08-13 | Basf Ag | Verfahren zur herstellung von polyurethan-elastomeren und hierfuer geeignete mischungen aus polyoxybutylen-polyoxyalkylen-glykolen und glycidylverbindungen |
| WO2004085509A1 (en) * | 2003-03-24 | 2004-10-07 | Solvay (Société Anonyme) | Process for the manufacture of foams composed of polyurethane or of modified polyurethane |
| CN101257974A (zh) * | 2005-09-01 | 2008-09-03 | 巴斯夫欧洲公司 | 聚异氰脲酸酯硬质泡沫及其生产的方法 |
| WO2007132463A1 (en) * | 2006-05-15 | 2007-11-22 | Bromine Compounds Ltd. | Flame retardant composition |
| CN103391954A (zh) * | 2010-12-15 | 2013-11-13 | 拜耳知识产权有限责任公司 | 耐高温泡沫材料 |
| CN103059242A (zh) * | 2013-01-09 | 2013-04-24 | 江苏科泰绝热新材料有限公司 | 一种环氧树脂改性的聚异氰脲酸酯耐高温硬质泡沫塑料及其制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP3259293B1 (de) | 2021-08-04 |
| HUE056812T2 (hu) | 2022-03-28 |
| CN107250229A (zh) | 2017-10-13 |
| EP3059270A1 (de) | 2016-08-24 |
| EP3259293A1 (de) | 2017-12-27 |
| PT3259293T (pt) | 2021-08-27 |
| ES2894100T3 (es) | 2022-02-11 |
| WO2016131874A1 (de) | 2016-08-25 |
| US20180066100A1 (en) | 2018-03-08 |
| RS62467B1 (sr) | 2021-11-30 |
| PL3259293T3 (pl) | 2022-03-14 |
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