CN104540864B - 具有提高的耐化学性的聚脲弹性体 - Google Patents
具有提高的耐化学性的聚脲弹性体 Download PDFInfo
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- CN104540864B CN104540864B CN201380041700.9A CN201380041700A CN104540864B CN 104540864 B CN104540864 B CN 104540864B CN 201380041700 A CN201380041700 A CN 201380041700A CN 104540864 B CN104540864 B CN 104540864B
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- polyamine
- spua
- filler particles
- amine
- polyalcohol
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- 239000000126 substance Substances 0.000 title claims description 22
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- 239000000945 filler Substances 0.000 claims abstract description 32
- 238000000034 method Methods 0.000 claims abstract description 25
- 150000001412 amines Chemical class 0.000 claims abstract description 24
- 239000004970 Chain extender Substances 0.000 claims abstract description 17
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 14
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 14
- 239000000376 reactant Substances 0.000 claims abstract description 10
- 239000000654 additive Substances 0.000 claims abstract description 6
- 230000000996 additive effect Effects 0.000 claims abstract description 6
- 239000012752 auxiliary agent Substances 0.000 claims abstract description 5
- 125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims abstract description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims abstract 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 26
- 239000000178 monomer Substances 0.000 claims description 21
- 229920000642 polymer Polymers 0.000 claims description 18
- 229920002396 Polyurea Polymers 0.000 claims description 16
- 238000000576 coating method Methods 0.000 claims description 11
- 239000011248 coating agent Substances 0.000 claims description 9
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- 125000001931 aliphatic group Chemical group 0.000 description 6
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
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- 101710130081 Aspergillopepsin-1 Proteins 0.000 description 4
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Abstract
本发明涉及一种用于制备聚脲弹性体的方法，其中将(a)多异氰酸酯与(b)多元胺、(c)如果适用的，含伯胺或仲胺基团的胺扩链剂、(d)如果适用的，多元醇和(e)如果适用的，助剂和添加剂材料混合形成反应混合物并进行固化，其中组分(a)至(d)中至少一种包含分散的填料颗粒。
Description
本发明涉及一种用于制备聚脲弹性体的方法，其中将(a)多异氰酸酯与(b)多元胺、(c)任选地包含伯胺或仲胺基团的胺扩链剂、(d)任选地多元醇和(e)任选地助剂和添加剂混合形成反应混合物并进行固化，其中组分(a)至(d)中至少一种包含分散的填料颗粒。
特别地，聚脲弹性体显示出高的抗环境影响性、高的耐化学性和快速固化(通常仅需几秒钟)。因此，聚脲弹性体通常被用作涂层剂，以保护承受巨大压力的区域的表面。其弹性体特性保护基板免受机械压力，同时其高的耐化学性保护基底材料免受化学侵蚀。因此，应用聚脲弹性体尤其聚脲喷涂弹性体的典型领域是涂料领域，尤其是用于混凝土修复和防水(屋顶涂层、停车甲板涂层、桥梁修复、隧道修复)、“二级防护(secondary containment)”(用于存储化学品、废水或油的槽或危险货物装载区的收集池(collection basin)的涂层)、防腐(货船、载货汽车、皮卡和有轨电车的装载区)或“初级防护”(废水井、水处理厂)的涂料领域。然而，耐化学性可被进一步改良，尤其是在高度酸性环境中。其可通过例如使用聚脲来实现，所述聚脲的起始物料经碳氢化合物改性。
因此，US 2008/0097068记载了使用己内酯制备聚脲弹性体以获得提高的耐化学性。然而，所获得的聚脲弹性体的机械特性处于相对低的水平。
此外，US 2011/0098417，例如，记载了聚丁二烯二醇在多元胺组分以及异氰酸酯组分中作为聚合物成分的用途。这导致了聚脲弹性体对各种酸、碱和有机溶剂的较高耐性。然而，聚丁二烯二醇价格昂贵且不易制得。此外，聚丁二烯二醇的使用增加了多元胺或多异氰酸酯组分的粘度，导致用于制备聚脲的组分难以加工。最终，所获得的聚脲弹性体的机械特性仍需提高。
WO 2010/039986记载了胺官能化的聚异丁烯，其被用作用于制备聚脲弹性体的多元胺组分的成分，以便获得更高的耐化学性。胺官能化的聚异丁烯同样是昂贵的且不易制得。此外，胺官能化的聚异丁烯的使用增加了多元胺组分的粘度，导致用于制备聚脲的组分难以加工。最终，所获得的聚脲弹性体的机械特性仍需提高。
EP 1112838公开了由聚合物多元醇获得的致密的聚氨酯弹性体。其并未测定聚合物多元醇对这些聚氨酯弹性体的耐化学性的影响，特别是鉴于聚脲弹性体原则上比聚氨酯弹性体的耐化学性高的事实。
EP 84841记载了由具有末端芳族氨基的多元胺制备的聚脲泡沫体和聚脲弹性体，其包含基于自由基聚合单体的聚合物。根据EP 84841，芳族结合(aromatically bound)胺基是获得有用的聚脲弹性体所必需的。对比实施例9示出了从脂族聚醚胺和甲苯系异氰酸酯获得聚脲弹性体的试验。其产生了一种粘性的、蜡状、并因此具有低价值的产物。
EP 528432记载了用于RIM过程的聚脲树脂，其包含可通过至少两种烯键式不饱和单体的自由基原位聚合得到的固体颗粒，其中烯键式不饱和单体中的至少一种为其均聚物的玻璃化转变温度低于-20℃的单官能丙烯酸酯单体；这里提及丙烯酸酯。这产生了在低温下具有改进的冲击强度的聚脲弹性体。其缺点在于丙烯酸酯易发生水解，并因此不利于获得高的耐化学性。
因此，本发明的目的是提供一种用于制备聚脲弹性体的方法，该方法容易进行且成本低廉，并且所获得的聚脲弹性体具有高的耐化学性和优良的机械特性。
出人意料地发现，在用于制备聚脲弹性体的液体起始组分中，例如在对异氰酸酯呈反应性的组分(尤其聚合物多元醇或聚合物多元胺)中使用分散的填料颗粒可提高聚氨酯弹性体和聚脲弹性体的耐化学性。
具体地，本发明的目的通过一种用于制备聚脲弹性体的方法实现，其中将(a)多异氰酸酯与(b)多元胺、(c)任选地包含伯胺或仲胺基团的胺扩链剂、(d)任选地多元醇和(e)任选地助剂和添加剂混合形成反应混合物并进行固化，其中组分(a)至(d)中的至少一种包含分散的填料颗粒。本发明的目的同样通过由该方法获得的聚脲弹性体实现。
聚脲弹性体是一种至少双官能的异氰酸酯与一种至少双官能的伯胺或仲胺的反应产物。聚脲弹性体通常为致密的聚脲。在此，致密意指聚脲弹性体的密度通常在800至1500g/l，优选在850至1300g/l，特别在900至1200g/l的范围内。本发明的聚脲弹性体显示出弹性，即，其拉伸强度根据DIN 53504为至少10MPa，优选为至少12MPa，特别为至少15MPa，且其断裂伸长率根据DIN 53504为至少100％，优选为150至1000％，特别为200至800％。在此，所述测试样本，在制备完成后和测试进行前，在23℃且相对空气湿度为50％的环境中存储至少24小时。
对于多异氰酸酯(a)，可使用任何已知用于制备聚脲弹性体的多异氰酸酯，所述多异氰酸酯包含二苯甲烷-2,4’-二异氰酸酯和/或二苯甲烷-4,4’-二异氰酸酯(也被称为2,4’-MDI和4,4’-MDI)。这些通常以预聚物形式使用。为此，将过量异氰酸酯(a1)与多元醇(a2)和/或扩链剂(a3)反应，以形成异氰酸酯封端的预聚物。优选使用二苯甲烷-2,4’-二异氰酸酯和/或二苯甲烷-4,4’-二异氰酸酯作为异氰酸酯(a1)。异氰酸酯(a1)特别优选包含二苯甲烷-2,4’-二异氰酸酯和二苯甲烷-4,4’-二异氰酸酯。此外，也可使用其他常规的异氰酸酯，优选芳族二异氰酸酯，特别是甲苯二异氰酸酯、单体的二苯甲烷二异氰酸酯(例如2,2’-MDI)或具有超过2个环的二苯甲烷二异氰酸酯的同系物(即，聚合MDI)，以及这些二异氰酸酯的混合物。二苯甲烷二异氰酸酯还可用作与其衍生物的混合物。在此，二苯甲烷二异氰酸酯可特别优选包含至多10重量％，更特别优选包含至多5重量％的碳化二亚胺-、脲二酮-(uretdione-)、脲基甲酸酯-或脲酮亚胺-改性的二苯甲烷二异氰酸酯，特别是碳化二亚胺-改性的二苯甲烷二异氰酸酯。除2,4’-MDI和4,4’-MDI外，优选使用双官能异氰酸酯。2,4’-MDI和4,4’-MDI在异氰酸酯(a1)中的比例优选为大于60重量％，特别优选大于80重量％，尤其大于98重量％。在此，2,4’-MDI与4,4’-MDI的重量比优选为10:90至90:10，特别优选为30:70至70:30，尤其为40:60至60:40。
对于多元醇(a2)，通常使用聚氨酯化学中已知的多元醇。多元醇(a2)的数均分子量大于400g/mol，优选大于550g/mol，并且可为例如聚醚醇(polyetherol)、聚酯醇(polyesterol)或聚碳酸酯醇(polycarbonatol)，其中多元醇的平均官能度优选为<3至1.7，特别优选为<2.5至1.9，尤其为<2.1至1.9。
聚醚醇可通过已知方法制备，例如通过使用碱金属氢氧化物或碱金属醇盐作为催化剂，并添加至少一种包含2至3个对异氰酸酯基团呈反应性的氢原子的起始分子，由一种或多种在亚烷基中具有2至4个碳原子的环氧烷烃的阴离子聚合反应制备，或通过使用路易斯酸例如五氯化锑或氟化硼醚合物(boride fluoride etherate)由一种或多种在亚烷基中具有2至4个碳原子的环氧烷烃的阳离子聚合反应制备。合适的环氧烷烃为，例如，四氢呋喃、1,3-环氧丙烷、1,2-或2,3-环氧丁烷，并且优选为环氧乙烷和1,2-环氧丙烷。此外，已知为DMC催化剂的多金属氰化物可被用作催化剂。特别地，所述环氧烷烃可交替连续地使用或作为混合物使用。优选使用1,2-环氧丙烷和环氧乙烷的混合物，其中环氧乙烷作为环氧乙烷末端嵌段(“EO帽”)的用量为10至50％，以便所形成的多元醇具有大于70％的伯OH端基。
可能的起始分子为水或2-羟基和3-羟基醇，例如乙二醇、1,2-和1,3-丙二醇、二乙二醇、二丙二醇、1,4-丁二醇、丙三醇或三羟甲基丙烷，优选乙二醇、1,2-和1,3-丙二醇、二乙二醇、二丙二醇、三丙二醇和1,4-丁二醇。
聚醚多元醇(优选聚氧亚丙基聚氧亚乙基多元醇)的平均官能度为1.7至3，特别优选为1.8至2.5，尤其为1.9至2.1，且其分子量优选为1000至12 000g/mol，特别优选为1400至8000g/mol，尤其为1700至6000g/mol。优选使用由双官能起始分子通过DMC催化制得的聚醚多元醇。特别优选使用聚四氢呋喃作为聚醚多元醇。在此，官能度通常为1.8至3，优选为1.9至2.2，特别优选为1.95至2.1，且其数均分子量通常为500至5000g/mol，优选为750至4000g/mol，特别优选为800至2500g/mol，尤其为1500至2200g/mol。
聚酯多元醇例如可由具有2至12个碳原子的有机二元羧酸(优选具有4至6个碳原子的脂族二元羧酸)和具有2至12个碳原子，优选2至6个碳原子的多羟基醇(优选二元醇)制得。可能的二元羧酸为例如琥珀酸、戊二酸、己二酸、辛二酸、壬二酸、癸二酸、十二烷二酸、马来酸、富马酸、邻苯二甲酸、间苯二甲酸和对苯二甲酸。二元羧酸可单独使用或以彼此的混合物形式使用。还可使用相应的二元羧酸衍生物，例如具有1至4个碳原子的醇的二元羧酸酯或二元羧酸酐代替游离的二元羧酸。优选使用重量比为例如20-35:35-50:20-32的琥珀酸、戊二酸和己二酸的二元羧酸混合物，特别为己二酸。二羟基醇和多羟基醇，尤其二元醇的实例为：乙二醇、二乙二醇、1,2-或1,3-丙二醇、二丙二醇、1,4-丁二醇、1,5-戊二醇、1,6-己二醇、1,10-癸二醇、丙三醇和三羟甲基丙烷。优选使用乙二醇、二乙二醇、1,4-丁二醇、1,5-戊二醇、1,6-己二醇。还可使用衍生自内酯例如己内酯，或羟基羧酸例如羟基己酸的聚酯多元醇。
为了制备聚酯多元醇，可在没有催化剂的情况下或优选在酯化反应催化剂的情况下，有利地在惰性气氛例如氮气、一氧化碳、氦气、氩气等中，在150至250℃、优选180至220℃的熔融温度下，任选地在减压下，将有机(例如芳族，优选脂族)多元羧酸和/或其衍生物与多羟基醇缩聚至优选小于10，特别优选小于2的预期酸值。在一个优选实施方案中，首先在大气压力下，随后在小于500mbar，优选50至150mbar的压力下，将所述酯化混合物在上述温度下缩聚至80至30，优选40至30的酸值。可能的酯化催化剂为，例如，以金属、金属氧化物或金属盐形式的铁、镉、钴、铅、锌、锑、镁、钛和锡催化剂。然而，还可在稀释剂和/或夹带剂例如苯、甲苯、二甲苯或氯苯的存在下，在液相中进行缩聚，以便共沸蒸馏出缩合的水。为了制备聚酯多元醇，有机多元羧酸和/或其衍生物与多羟基醇可在1:1-1.8，优选1:1.05-1.2的摩尔比下有利进行缩聚。
所得聚酯多元醇优选具有1.8至3，特别优选具有1.9至2.5，尤其具有1.95至2.1的官能度，且其分子量为480至5000g/mol，优选为1000至4500g/mol，尤其为1600至4500g/mol。
对于多元醇(a2)，可使用例如包含填料的多元醇。这些包含填料的多元醇分散体还被称为聚合物多元醇或接枝多元醇。此类包含填料的多元醇分散体是已知的，且其制备方法记载于例如“Mihail Ionescu,Chemistry and Technology of Polyols forPolyurethanes,Rapra Technology Ltd.,2005,ISBN:185957-491-2)中。
可任选地将扩链剂(a-3)添加到反应中，以形成多异氰酸酯预聚物。用于预聚物的合适的扩链剂(a-3)为二羟基或三羟基醇，例如二丙二醇和/或三丙二醇，或二丙二醇和/或三丙二醇与环氧烷烃的加合物，优选二丙二醇，但优选不添加扩链剂(a3)。
作为一种替代，所述组分(a2)和(a3)的全部或部分可被多元胺(b)或胺扩链剂(c)中描述的化合物替代。
为了制备异氰酸酯预聚物，将异氰酸酯(a1)、多元醇(a2)和任选地其他的多元醇、扩链剂和/或交联剂进行混合。所述化合物以一定比例进行混合，以便预聚物的NCO含量为至少5重量％，优选为至少7重量％且不超过33重量％，特别优选为10至30重量％，更优选为12至25重量％，尤其为14至20重量％。优选将混合物加热至30至100℃，特别优选50至90℃，尤其约80℃的温度。
在另一优选实施方案中，多异氰酸酯(a1)也可直接用作多异氰酸酯(a)，而无需转化为预聚物。
对于多元胺(b)，可使用已知为聚醚胺的至少一种聚氧化烯胺(polyoxyalkyleneamine)，优选至少两种聚氧化烯胺的混合物。此类聚氧化烯胺优选为数均分子量至少为350g/mol，例如350至6000g mol-1，优选380至5100g mol-1的胺封端的双官能或更高官能的聚环氧烷(通常为聚环氧乙烷(polyoxyethylene oxide)或聚环氧丙烷(polyoxypropylene oxide))，其中氨基优选为脂族键合。还可使用胺封端的聚四氢呋喃(PTHF)。聚醚胺的胺基优选为伯胺基。还可仅使用一种聚醚胺。聚醚胺(b)特别为二元胺或三元胺。此类化合物由例如Huntsman以的商品名进行销售，或由BASF以的商品名作为聚醚胺进行销售。
多元胺通常由相应的多元醇经催化胺化制得。优选被胺化的聚醚醇和聚酯醇的制备已在上文对组分(a2)的描述中公开。特别地，2-或3-官能的聚环氧丙烷被转化为相应的二元胺或三元胺。
可能的填料颗粒为所有的增强填料，其沿着最长轴的平均粒径为0.001至<100μm，优选为0.01至50μm，特别优选为0.1至10μm，尤其为0.2至3μm。在此，粒径分布可为单峰分布或双峰分布或多峰分布。填料颗粒优选基本上为球形，且颗粒的最长轴优选不大于最短轴的两倍。填料颗粒包括优选可在多元胺(b)中分散的无机和有机填料。无机颗粒可为半金属氧化物、金属氧化物(例如以下金属的氧化物：Zn、Al、Si、Fe、Ti、B、Zr和V)、混合氧化物、碳化物、氮化物、碳酸盐(例如CaCO3)、氢氧化物、碳(例如石墨、石墨烯、纳米管、炭黑和/或纤维)、无机盐、无机颜料、硅酮树脂、硅酮(silicone)和/或二氧化硅，或其混合物，其中所述这些类别的颗粒均可任选被表面改性，例如疏水改性或亲水改性。为了疏水化，可使用例如至少一种选自硅烷、硅氧烷、季铵化合物、阳离子聚合物和脂肪酸及其阴离子的化合物。
对于无机颗粒，还可使用各种硅酸盐材料。为此，可使用各种来源的硅酸盐材料，例如硅溶胶(二氧化硅可以分散在水、(一元)醇或多元醇中)、表面官能化的硅溶胶、层状硅酸盐或热解硅石(pyrogenic silica)。可根据本发明使用的市售硅酸盐材料的实例为 和
可使用例如聚合物颗粒作为无机填料。在此，优选使用热塑性聚合物。这些填料以分散形式存在于反应混合物中。在这种情况下，所述填料优选以在组分(a)至(d)的一种或多种组分中，特别优选在组分(b)至(d)的一种或多种组分中的分散体存在。特别地，填料颗粒以在多元胺(b)中的分散体存在。
例如，通过分散(任选地借助稳定剂)或通过单体的聚合可将填料颗粒引入至组分(a)至(d)的一种或多种组分中。如果热塑性聚合物颗粒被用作填料颗粒，则其还可以熔体的形式分散在组分(a)至(d)中的一种组分中，例如分散在异氰酸酯组分中。
如果所述填料被分散在异氰酸酯中，则可使用例如含有填料的多元醇作为多元醇(a2)。这些含有填料的多元醇分散体还被称为聚合物多元醇或接枝多元醇。此类含有填料的多元醇分散体是已知的，且其制备方法记载于例如“Mihail Ionescu,Chemistry andTechnology of Polyols for Polyurethanes,Rapra Technology Ltd.,2005,ISBN:185957-491-2)中。
聚合物颗粒在多元胺(b)中的分散体还被称为聚合物多元胺或接枝多元胺，其可通过使用自由基引发剂(通常为单独的偶氮化合物或过氧化物，或以与其他引发剂混合的形式)，由单体、任选地一种或多种稳定剂以及任选地一种或多种大分子单体以及任选地一种或多种调节剂(moderator)在作为连续相的聚醚胺或聚酯胺中的自由基聚合反应而制备。代表连续相的聚醚胺或聚酯胺通常被称为载体多元胺。作为聚合物多元胺的制备方法的实例，可参考例如专利US 4286074。为了本发明的目的，特别优选使用聚合物多元胺。可能的载体多元胺为b)中所述的所有多元胺。
用于制备聚合物多元胺的填充材料的合适的烯键式不饱和单体，除苯乙烯和丙烯腈外，还可为例如丁二烯、异戊二烯、1,4-戊二烯、1,6-己二烯、1,7-辛二烯、苯乙烯、α-甲基苯乙烯、2-甲基苯乙烯、3-甲基苯乙烯、4-甲基苯乙烯、2,4-二甲基苯乙烯、乙基苯乙烯、异丙基苯乙烯、丁基苯乙烯、苯基苯乙烯、环己基苯乙烯、苄基苯乙烯以及类似的衍生物；取代的苯乙烯，例如氰基苯乙烯、硝基苯乙烯、N,N-二甲氨基苯乙烯、乙酰氧基苯乙烯、4-乙烯基苯甲酸甲酯、苯氧基苯乙烯、对乙烯基苯基氧化物(p-vinylphenyl oxide)以及类似的衍生物及其混合物；丙烯腈、丙烯酸、甲基丙烯酸、甲基丙烯腈、甲基乙烯基酮、乙烯基乙基酮、乙烯基苯基酮、乙烯基乙基砜、N-甲基-N-乙烯基乙酰胺、N-乙烯基吡咯烷酮、乙烯基咪唑、二乙烯基亚砜、二乙烯基砜、乙烯基磺酸钠、乙烯基磺酸甲酯(methyl vinylsulfonate)、N-乙烯基吡咯、膦酸乙烯基酯以及类似的衍生物；富马酸二甲酯、马来酸二甲酯、马来酸、巴豆酸、富马酸、衣康酸、衣康酸单甲酯、烯丙醇、乙烯基吡啶以及类似的衍生物及其混合物。优选的烯键式不饱和单体为苯乙烯、丙烯腈及其混合物。
在一个优选实施方案中，丙烯腈、苯乙烯，特别是比例为1:3至3:1的苯乙烯和丙烯腈被用作烯键式不饱和单体。此外，大分子单体优选添加到聚合反应中。任选地在使用调节剂和自由基引发剂的情况下进行聚合反应。
大分子单体为直链或支链的聚醚胺和/或多元醇，其分子量为>1000g/mol，且包含至少一个末端、反应性烯键式不饱和基团。烯键式不饱和基团可通过聚醚胺和/或多元醇与以下化合物的反应而连接至现存的多元胺：羧酸(例如丙烯酸)、羧酸卤化物(carboxylichalides)(例如丙烯酰氯)、羧酸酐(例如马来酸酐)、富马酸、丙烯酸酯和甲基丙烯酸酯衍生物、烯键式不饱和环氧化物(例如1-乙烯基环己烯3,4-环氧化物、1-丁二烯一氧化物、乙烯基缩水甘油醚、甲基丙烯酸缩水甘油酯、烯丙基缩水甘油醚)，以及异氰酸酯衍生物(例如3-异丙烯基-1,1-二甲苄基异氰酸酯甲基丙烯酸异氰酸基乙酯)。制备多元胺的另一路线为利用具有羟基和烯键式不饱和性的起始分子使环氧丙烷和环氧乙烷进行烷氧基化反应，其中末端OH基团通过催化胺化被转化为胺基。所有大分子单体中的部分大分子单体还可具有OH官能团而非胺基官能团。这些可通过免除胺化步骤或将烯键式不饱和基团连接至现存的多元醇上而实现。在此，大分子单体的制备通常使用摩尔过量的不饱和化合物进行，基于多元胺或多元醇计。
任选用于制备聚合物颗粒在多元胺(b)中的分散体的稳定剂为，例如，记载于专利WO 2009/138379中的那些。
通过使用大分子单体可阻止颗粒的团聚。在自由基聚合期间，大分子单体，如果存在，被同时纳入聚合物链中。以此方式，可形成具有聚醚嵌段且例如聚丙烯腈-苯乙烯嵌段的共聚物，其可起到连续相和分散相之间界面处的相相容剂(phase compatibilizer)的作用，并且可抑制聚合物颗粒的团聚。大分子单体的比例可高达>90重量％，且通常为1至60重量％，优选为1至40重量％，特别优选为1至15重量％，各自以用于制备聚醚多元胺的单体的总重量计。载体多元醇或载体聚醚胺与自由基聚合单体的接枝反应还造成填料颗粒的稳定化。
调节剂(也被称为链转移剂)通常用于制备聚合物多元胺。调节剂引起增长自由基的链转移，并因此降低了所形成的共聚物的分子量，结果导致聚合物分子之间的交联降低，其进而影响分散体的粘性和稳定性以及聚合物多元胺的可滤性。调节剂的比例通常为0.5至25重量％，基于用于制备聚合物多元胺的单体的总重量计。通常用于制备聚合物多元胺的调节剂为醇类(例如1-丁醇、2-丁醇、异丙醇、乙醇、甲醇)、环己烷、甲苯、硫醇类(例如乙硫醇、1-庚硫醇、2-辛硫醇、1-十二硫醇、苯硫酚、巯基乙酸2-乙基己基酯、巯基乙酸甲酯、环己硫醇)，以及烯醇醚化合物、吗啉和α-(苄甲酰氧基)苯乙烯。优选使用烷基硫醇。
自由基聚合反应通常使用选自以下的过氧化物和/或偶氮化合物进行引发：例如，过氧化二苯甲酰、过氧化月桂酰、过氧-2-乙基己酸叔戊酯(t-amyl peroxy-2-ethylhexanoate)、二叔丁基过氧化物、过氧碳酸二异丙酯(diisopropylperoxocarbonate)、过氧-2-乙基己酸叔丁酯、过氧新戊酸叔丁酯(t-butyl perpivalate)、过氧新癸酸叔丁酯(t-butyl perneodecanoate)、过氧苯甲酸叔丁酯(t-butylperbenzoate)、过氧巴豆酸叔丁酯(t-butyl percrotonate)、过氧异丁酸叔丁酯(t-butylperisobutyrate)、过氧-1-甲基丙酸叔丁酯(t-butyl peroxy-1-methylpropanoate)、过氧-2-乙基戊酸叔丁酯(t-butyl peroxy-2-ethylpentanoate)、过氧辛酸叔丁酯(t-butylperoxyoctanoate)和过氧邻苯二甲酸二叔丁酯(di-t-butyl perphthalate)、2,2'-偶氮双(2,4-二甲基戊腈)、2,2’-偶氮二异丁腈(AIBN)、2,2’-偶氮二异丁酸二甲酯(dimethyl 2,2’-azobisisobutyrate)、2,2'-偶氮双(2-甲基丁腈)(AMBN)、1,1'-偶氮双(1-环己烷甲腈)。引发剂的比例通常为0.1至6重量％，基于用于制备聚合物多元胺的单体的总重量计。
由于单体的反应速率和引发剂的半衰期，用于制备聚合物多元胺的自由基聚合反应通常在70至150℃的温度以及至多20巴的压力下进行。用于制备聚合物多元醇的优选反应条件是温度为80至140℃和压力为大气压至15bar。
聚合物多元胺可在具有连续引入和排放功能的搅拌容器、级联搅拌容器、管式反应器和具有连续引入和排放功能的环流反应器中以连续过程进行制备，或在间歇式反应器或半间歇式反应器中以不连续过程进行制备。
用于制备聚合物多元胺的反应还可在惰性溶剂的存在下进行。可使用的溶剂为，例如：苯、甲苯、二甲苯、乙腈、己烷、庚烷、二噁烷、乙酸乙酯、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺等。优选苯、二甲苯和甲苯。
作为一种替代，分散的填料颗粒还可通过熔融乳化方法获得。该方法记载于WO2009/138379。在此，将热塑性聚合物任选地与稳定剂和多元胺(b)一起加热至高于热塑性聚合物的熔点的温度，例如通过超声、挤压机或齿轮分散机进行均质化，并冷却至低于热塑性聚合物的熔点的温度。原则上可使用所有的热塑性聚合物。优选使用可通过上述单体的聚合获得的热塑性聚合物。还可任选地添加乳化剂。例如，可使用记载于WO 2009/138379中的稳定剂和乳化剂。
在一个优选实施方案中，在熔融乳化过程中使用的热塑性聚合物选自聚苯乙烯、聚(苯乙烯-共-丙烯腈)、聚丙烯腈、聚丙烯酸酯、聚甲基丙烯酸酯、聚烯烃(例如聚丙烯、聚乙烯、聚异丁烯、聚丁二烯)、聚酯、聚酰胺、聚氯乙烯、聚对苯二甲酸乙二醇酯、聚乙酸乙烯酯、聚乙二醇、聚氨酯、聚脲及其混合物，优选选自聚(苯乙烯-共-丙烯腈)、聚丙烯腈及其混合物。
聚合物多元胺优选使用双官能聚醚胺作为载体多元胺进行制备，所述聚醚胺主要具有伯胺基团，且数均分子量为至少350g/mol，例如在350至6000g/mol的范围内，优选在380至5100g/mol的范围内。
在本发明的另一优选实施方案中，聚合物多元胺胺化的聚四氢呋喃(PTHF)被用作载体多元胺，其通常具有的数均分子量为300至4000g/mol，优选为750至3000g/mol，优选为800至2500g/mol，特别为约2000g/mol。
在一个优选实施方案中，填料组分包括丙烯腈、苯乙烯和任选的大分子单体，其中丙烯腈的比例为10至75重量％，优选25至40重量％，苯乙烯的比例为30至90重量％，优选55至75重量％，大分子单体的比例为0至30重量％，优选3至10重量％，基于聚合物多元胺的填料组分的总重量计。
在一个优选实施方案中，聚合物多元胺的填料含量为10至80重量％，特别优选为25至60重量％，尤其为35至55重量，基于聚合物多元胺的总重量计。
聚合物多元胺的填料含量被计算为所用单体和大分子单体与所用的载体多元胺的百分比，且通常通过重量分析成品聚合物多元胺中的填料的量与聚合物多元胺的总质量的百分比来确定的。
填料含量为至少0.5重量％，基于组分(a)至(e)的总重量计。填料含量优选为1至30重量％，特别优选为5至27重量％，更优选为7至25重量％，尤其为10至22重量％，各自以组分a)至e)的总重量计。还可使用不同填料颗粒的混合物。
对于胺扩链剂(c)，使用分子量小于350g/mol且优选为60至250g/mol的芳族和脂族二元胺。通常用在聚脲弹性体中的扩链剂为二乙基甲苯二胺(diethylenetoluenediamine，DETDA)。作为相比于脂族胺相对不活泼的组分，DETDA决定了所述体系的固化行为。因此，凝胶时间可通过对异氰酸酯呈降低的反应性的其他扩链剂来控制。为了获得光稳定性的聚脲喷涂弹性体，还可使用脂族扩链剂。此外，可使用上述其他胺扩链剂，例如4,4’-亚甲基双(2,6-二乙基)苯胺(MDEA)、4,4’-亚甲基双(2,6-二异丙基)苯胺(MDIPA)、4,4’-亚甲基双(3-氯-2,6-二乙基)苯胺(MCDEA)、二甲硫基甲苯二胺(DMTDA，300)或具有仲胺官能团的阻滞反应的扩链剂(例如N,N’-二(仲丁基)-氨基二苯基甲烷(DBMDA，4200)或N,N’-二仲丁基对苯二胺(4100)。
此外，用于制备本发明的聚脲弹性体的反应混合物还可包含多元醇(d)。这些包括(a2)中描述的所有多元醇。在多元胺(b)和多元醇(d)的总重量中多元醇(d)的比例优选小于50重量％，特别优选小于20重量％，更优选小于10重量％。特别地，没有使用多元醇(d)。在计算多元醇(d)的比例时不考虑多元醇(a2)。
助剂和添加剂包括催化剂、表面活性剂、阻燃剂、增强材料、粘合剂、UV稳定剂、抗氧化剂、染料、颜料和水解抑制剂以及抑制真菌的物质和抑制细菌的物质。向胺组分中添加添加剂受限于可加工粘度的需要。优选的添加剂为颜料、粘合剂、UV稳定剂、抗氧化剂和/或增强材料。这些物质在聚氨酯和聚脲生产中是已知的。
为了本发明的目的，增强材料为常规的有机和无机增强材料或粒径大于100μm的本身已知的增重剂。在此，粒径为最长轴。对于短切玻璃纤维，例如，所述“粒径”为纤维的长度。可提及的具体实例为无机填料，例如硅质矿物，例如层状硅酸盐，例如叶蛇纹石、膨润土、蛇纹石、角闪石(hornblende)、闪石(amphibole)、纤蛇纹石和滑石；金属氧化物，例如高岭土、氧化铝、氧化钛、氧化锌和氧化铁；金属盐，例如白垩和重晶石；无机颜料，例如硫化镉、硫化锌；以及玻璃等。优选使用高岭土(瓷土)、硅酸铝，以及硫酸钡与硅酸铝与玻璃纤维的共沉淀物。可能的有机填料的实例为：炭黑、三聚氰胺、松香、环戊二烯基树脂和接枝聚合物，以及纤维素纤维、基于芳族和/或脂族二元羧酸的聚酰胺纤维、聚丙烯腈纤维、聚氨酯纤维、聚酯纤维，尤其是碳纤维。
无机和有机增强材料可单独使用或作为混合物使用，并且在反应混合物中的有利添加量为0.5至50重量％，优选1至40重量％，基于组分(a)至(e)的重量计。
为了制备本发明的聚脲弹性体，优选在10至90℃，特别优选在15至70℃，特别在20至50℃的温度下混合组分(a)至(e)。然后，将该混合物优选作为涂料施加在制品上，并使其固化，以形成聚脲弹性体。为此，还可混合组分(b)和，如果存在，(c)至(e)，以形成多元醇组分，所述多元醇组分随后与异氰酸酯组分(a)混合。在此，选择混合比例，以便多异氰酸酯(a)的NCO基团与组分(b)和任选的(c)和(d)中的反应性碳氢原子的总和的当量比为0.9-1.2:1，优选为1.0-1.15:1。比例1:1对应于异氰酸酯指数100。
聚脲弹性体涂层的厚度优选为0.01mm至20cm，优选为0.1mm至5cm，特别优选为0.5mm至10mm。
其他非绝对必要的制剂成分为例如稀释剂，通常为反应性稀释剂，其在使用时通常被添加到异氰酸酯组分中。用于异氰酸酯组分的反应性稀释剂的实例为碳酸亚烃酯。然而，添加反应性稀释剂可导致聚脲喷涂弹性体的机械性能以及抗老化性劣化。
组分b)还可特别包括磨损改性剂(abrasion improvers)。优选使用硅酮改性的醇(尤其硅酮改性的乙二醇)作为磨损改性剂。
该体系通常通过喷涂进行施用，其中所述组分在从喷枪中排出前在高压和高温下于喷枪的混合头中进行混合，并因此发生反应。作为一种替代，还可将所述组分单独地施加至待涂布的表面，其中混合过程通过液滴的自发混合而进行。反应时间通常仅需几秒钟。为了本发明的目的，组分(a)至(e)的混合物在反应转化率小于90％(以异氰酸酯基团计)时被称为反应混合物。
喷涂的多异氰酸酯和胺组分的体积比优选为1:1，也可以是30:70至70:30体积％，但优选至多1.1:1。
特别当喷涂表面潮湿时，可借助底漆(primer)进行预处理，以提高粘附性。同样特别用于粘附至潮湿基板的助粘剂也可被添加到异氰酸酯或优选多元胺组分中。
底漆的实例为硅氧烷和官能化的硅氧烷。可特别提及的是环氧基烷氧基硅烷(epoxyalkoxysilane)、氨基烷氧基硅烷(aminoalkoxysilane)和乙烯基烷氧基硅烷(vinylalkoxysilane)。市售的底漆的其他实例为钛酸盐例如新戊基(二烯丙基)氧基三(间-氨基)苯基钛酸盐或锆酸盐例如新戊基(二烯丙基)氧基三(间-乙二胺基)乙基锆酸盐。其他可能的底漆为单组分或双组分聚氨酯体系、聚乙烯胺、聚丙烯酸酯和环氧树脂。涂布前，可将所述底漆分散、乳化或溶解在水或其他溶剂中。
任何表面均可进行喷涂。待喷涂的表面优选为矿物表面，例如混凝土或金属表面(例如钢铁表面)。
本发明还提供可一种聚脲弹性体，其可通过本发明的方法获得。
本发明的聚脲弹性体优选用于涂覆需抵抗机械和化学应力的表面，例如工业地板、混凝土修复和防水(例如用于屋顶、停车甲板涂层、桥梁修复、隧道修复)、“二级防护”(例如用于化学品槽、废水槽或油槽或危险货物装载区的收集池)、防腐(例如货船、载货汽车、皮卡和有轨电车的装载区)或“初级防护”(例如废水井、水处理厂或反应器(例如生物反应器))。特别地，本发明的聚脲弹性体被用于涂覆反应器(例如生物反应器)、用于化学品(尤其酸性化学品)的收集池或接触例如水处理厂或污水管道中的废水的收集池。
所得聚脲弹性体特别耐受化学品。这特别体现在，当存储于酸中后依然具有非常好的机械性能。
本发明的另一优势在于所述组分的易加工性能，特别地因为相比于用于制备已知的具有耐化学性的聚脲的起始化合物，包含分散的填料颗粒的多元胺(b)的粘度较低。所得的新聚脲弹性体还具有非常好的机械性能，例如具有至少80肖氏(Shore)A，优选至少85肖氏A，尤其至少40肖氏D的高硬度。
下文将通过实施例来说明本发明。
实施例
根据ASTM D7042测定粘性；根据DIN 53240测定OH值；根据DIN 13717测定胺值。
借助马尔文激光粒度分析仪(Malvern Mastersizer)测定粒径分布。各数值具有以下含义：
D10：颗粒总体积的10％具有比示值小的直径
D50：颗粒总体积的50％具有比示值小的直径
D90：颗粒总体积的90％具有比示值小的直径
激光粒度分析仪(粒径分布的测定)：激光粒度分析仪2000(静态光散射原理)；利用异丙醇稀释样品至测量所需浓度。
起始物料：
聚醚胺1：胺值为56.7mg KOH/g的脂族伯胺封端的聚氧亚丙基二胺(polyoxypropylene diamine)。
聚醚胺2：胺值为249.5mg KOH/g的脂族伯胺封端的聚氧亚丙基二胺。
扩链剂：重量比为80重量％:20重量％的3,5-二乙基-2,4-甲苯二胺与3,5-二乙基-2,6-甲苯二胺的混合物。
异氰酸酯：比例为50:50的4,4’-MDI和2,4’-MDI的混合物。
大分子单体：与(Meta)反应的羟值为18.4mg KOH/g的六官能聚醚醇。
(Meta)＝购自Cytec Industries的不饱和脂族异氰酸酯
DBTL：二月桂酸二丁基锡，TRIGON Chemie GmbH
64＝购自DuPont的自由基引发剂
实施例1：聚合物聚醚胺的制备
将663.4g聚醚胺1与5.4g大分子单体添加到搅拌高压釜中，并加热至125℃。随后在150分钟内，将溶解在663.4g聚醚胺1中的363.2g丙烯腈、726.5g苯乙烯、11.4g十二硫醇、6.5g64和60g大分子单体加入到反应混合物中。反应15分钟后，通过施加7mbar的真空，从产物中除去残余的单体。由此产生25℃下粘度为2832mPas且胺值为29.8mg KOH/g的聚合物聚醚胺。粒径分布的结果：D10＝0.328μm，D50＝0.662μm以及D90＝0.999μm。
聚脲弹性体的制备
由异氰酸酯(51.6重量％，以异氰酸酯预聚物的总重量计)和OH值为56mg KOH/g的双官能聚丙二醇(48.4重量％，以异氰酸酯预聚物的总重量计)制备异氰酸酯预聚物，作为用于制备聚脲弹性体的异氰酸酯组分。所得的异氰酸酯预聚物的NCO含量为15.0±0.1％，并且在25℃下的粘度为800±100mPas。
在温度为60至80℃且压力为150至180bar的条件下，借助市售的Isotherm PSM3000喷涂机，根据表1，将起始物质喷涂在聚四氟乙烯板(60cm*60cm)上，以形成层厚度为约20mm的聚脲弹性体。
苯乙烯-丙烯腈填充的聚脲体系的反应性(凝胶时间和表干时间)与参考体系相当。所得的聚脲弹性体的机械特性同样显示于表1中。
表1
相比于无填料的参照组，根据本发明制备的聚脲弹性体1和2随着填料含量的增加显示出明显改善的磨损值。
喷涂板的耐酸性和抗氧化性显示于表2、3、4和5中。为此，将所制备的样品各自在23℃下在指定的酸中存储指定的时间。SAN填充的聚脲在耐硝酸和硫酸方面具有显著提高。随着苯乙烯-丙烯腈颗粒的比例增加，硝酸的高度氧化作用被降低。在10％浓度的硝酸溶液中，即使在几周之后也几乎未观察到实施例1和2的外部变化，然而参照组1的实施例在几天后颜色变黑。在浓硝酸(68％)中，本发明的实施例(即，聚脲弹性体1和聚脲弹性体2)相比于参照组同样显示出显著减少的降解。
表2
表3
表4
表5
Claims (12)
1.一种用聚脲弹性体涂布表面的方法，其中
将a)多异氰酸酯，包含二苯甲烷-4,4’-二异氰酸酯和/或二苯甲烷-2,4’-二异氰酸酯或其预聚物，与
b)可通过多元醇的催化胺化获得的多元胺，
c)任选地，包含伯胺或仲胺基团的胺扩链剂，
d)任选地，多元醇，以及
e)任选地，助剂和添加剂，
混合形成反应混合物，并将所述反应混合物施加至待涂布的表面上并进行固化，其中组分(a)至(d)中至少一种包含分散的填料颗粒，所述填料颗粒通过苯乙烯和丙烯腈的混合物的单体进行聚合而获得；
其中所述填料颗粒存在于反应混合物中；
其中所述填料颗粒通过单体的聚合而引入；
其中聚脲弹性体具有的填料颗粒含量为5至27重量％，基于聚脲弹性体的总重量计；且
其中所述分散的填料颗粒沿着最长轴的平均粒径为0.001至<100μm。
2.权利要求1的方法，其中多异氰酸酯预聚物被用作多异氰酸酯(a)。
3.权利要求1或2的方法，其中多元胺的比例为至少75重量％，基于多元胺(b)和多元醇(d)的总重量计。
4.权利要求1或2的方法，其中通过喷涂施加至待涂布的表面。
5.权利要求1或2的方法，其中待涂布的表面选自矿物表面和金属表面。
6.权利要求5的方法，其中待涂布的表面选自工业地板；停车甲板；屋顶；桥梁；隧道；用于化学品槽或废水槽、油槽、危险货物装载区的收集池；载货汽车和有轨电车的装载区；废水井；水处理厂和反应器。
7.权利要求6的方法，其中待涂布的表面选自皮卡的装载区。
8.权利要求1或2的方法，其中热塑性聚合物的填料颗粒以其熔体的形式分散在异氰酸酯组分和/或多元胺(b)中。
9.权利要求1或2的方法，其中多元胺(b)包括聚合物多元胺。
10.权利要求1或2的方法，其中多元胺(b)包括聚合物聚醚胺。
11.一种聚脲弹性体涂层，其可通过权利要求1至10中任一项的方法获得。
12.权利要求11的聚脲弹性体涂层作为反应器、用于化学品或接触废水的收集池中的涂层的用途。
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| EP12179380.6A EP2695899A1 (de) | 2012-08-06 | 2012-08-06 | Polyharnstoff-Elastomere mit erhöhter Chemikalienbeständigkeit |
| EP12179380.6 | 2012-08-06 | ||
| PCT/EP2013/065760 WO2014023583A1 (de) | 2012-08-06 | 2013-07-25 | Polyharnstoff-elastomere mit erhöhter chemikalienbeständigkeit |
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| JO3155B1 (ar) | 2013-02-19 | 2017-09-20 | Senomyx Inc | معدِّل نكهة حلوة |
| CN105102420B (zh) * | 2013-03-28 | 2018-09-21 | 巴斯夫欧洲公司 | 基于1,3-二醇的聚醚胺 |
| US11059271B2 (en) * | 2014-09-19 | 2021-07-13 | Basf Se | Component composed at least to some extent of a layer structure and process for production thereof |
| US20180187046A1 (en) * | 2015-07-07 | 2018-07-05 | Akzo Nobel Coatings International B.V. | Coating Agent Composition for Producing Peelable and Chemically-Resistant Coatings |
| WO2017072033A1 (de) * | 2015-10-30 | 2017-05-04 | Akzo Nobel Coatings International B.V. | Verwendung einer beschichtungsmittelzusammensetzung zur innenbeschichtung von behältern |
| CN106753151B (zh) * | 2016-11-30 | 2019-05-10 | 青岛爱尔家佳新材料股份有限公司 | 一种防爆破冲击聚脲涂层及其制备方法 |
| CN107602799B (zh) * | 2017-08-22 | 2021-12-10 | 山西省建筑科学研究院 | 聚脲珍珠岩复合保温板的制备方法 |
| SG11202100846YA (en) | 2018-08-07 | 2021-02-25 | Firmenich Incorporated | 5-substituted 4-amino-1h-benzo[c][1,2,6]thiadiazine 2,2-dioxides and formulations and uses thereof |
| CN111454566A (zh) * | 2019-01-21 | 2020-07-28 | 宝山钢铁股份有限公司 | 一种快速修复材料 |
| US11198790B2 (en) * | 2019-03-21 | 2021-12-14 | Ddp Specialty Electronic Materials Us, Llc | Water-resistive coating composition |
| CN110256946A (zh) * | 2019-06-24 | 2019-09-20 | 江苏凯伦建材股份有限公司 | 聚脲防水涂料生产工艺 |
| CN111269557A (zh) * | 2020-04-14 | 2020-06-12 | 烟台恒诺新材料有限公司 | 一种中空纳米微球改性高分子隔热保温材料的制备方法 |
| KR102340369B1 (ko) * | 2021-07-19 | 2021-12-16 | (주)펜테크 | 차열 특성이 우수한 폴리우레아 도막방수재 및 이의 제조 방법 |
| CN113683749A (zh) * | 2021-08-27 | 2021-11-23 | 重庆中科超容科技有限公司 | 一种抗高过载轻质聚脲及其制备方法 |
| CN113956435B (zh) * | 2021-11-03 | 2022-06-21 | 湖南大学 | 一种聚脲交联网络弹性体的制备方法 |
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| CA2879661C (en) | 2020-07-21 |
| TR201908105T4 (tr) | 2019-06-21 |
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| JP2015527453A (ja) | 2015-09-17 |
| EP2880069B1 (de) | 2019-03-27 |
| EP2695899A1 (de) | 2014-02-12 |
| EA201590316A1 (ru) | 2015-07-30 |
| BR112015001842A2 (pt) | 2017-07-04 |
| ES2732376T3 (es) | 2019-11-22 |
| CA2879661A1 (en) | 2014-02-13 |
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| CL2015000302A1 (es) | 2015-07-10 |
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| CO7200275A2 (es) | 2015-02-27 |
| EA027428B1 (ru) | 2017-07-31 |
| PL2880069T3 (pl) | 2019-09-30 |
| MX2015001737A (es) | 2015-06-05 |
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