CN103025783A - 具有良好尺寸稳定性的聚氨酯整体泡沫材料 - Google Patents
具有良好尺寸稳定性的聚氨酯整体泡沫材料 Download PDFInfo
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- CN103025783A CN103025783A CN2011800287627A CN201180028762A CN103025783A CN 103025783 A CN103025783 A CN 103025783A CN 2011800287627 A CN2011800287627 A CN 2011800287627A CN 201180028762 A CN201180028762 A CN 201180028762A CN 103025783 A CN103025783 A CN 103025783A
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Abstract
本发明涉及一种生产密度为100-800g/l的聚氨酯整体泡沫材料的方法，其中将a)包含多异氰酸酯和热塑性聚合物的溶液与b)多元醇、c)发泡剂以及任选d)扩链剂和/或交联剂、e)催化剂和f)其他助剂和/或添加剂混合而形成反应混合物，将该反应混合物引入模具中并使其完全固化而形成聚氨酯泡沫模塑体。本发明进一步涉及可以由该方法得到的聚氨酯整体泡沫材料。
Description
本发明涉及一种生产密度为100-800g/l的聚氨酯整体泡沫的方法，其中将a)包含多异氰酸酯和脂族热塑性聚合物的溶液与b)多元醇、c)发泡剂以及任选d)扩链剂和/或交联剂、e)催化剂和f)其他助剂和/或添加剂混合而得到反应混合物，将该反应混合物引入模具中并使其反应而得到聚氨酯泡沫模制品。本发明进一步提供了可以由该方法得到的聚氨酯整体泡沫。
聚氨酯整体泡沫是具有紧凑表面和多孔状芯的聚氨酯模制品。聚氨酯整体泡沫及其生产长时间已知且例如描述于Modern Shoemaking No.61：Solings，2001年11月，Stephen Abbott和Mike George，Satra TechnologyCentre 2001中。聚氨酯整体泡沫用于各种领域中。典型的应用是作为鞋底，例如用于系带鞋(schuhsohle)、运动鞋、凉鞋和长筒靴，以及还用于汽车内饰领域中，例如作为方向盘、头枕或变速器把手。其他可能的应用是作为椅子的扶手或作为摩托车车座。
改善聚氨酯的尺寸稳定性的各种可能方式已经在文献中讨论。例如，EP 1 042 384描述了通过使用大量聚醚接枝多元醇生产基于聚醚醇的低密度、尺寸稳定的鞋底。该方法的缺点是与基于聚酯醇的鞋底相比机械性能显著更差。此外，高比例的聚合物聚醚醇对多元醇组分的粘度具有不利影响。
EP 1 790 675和EP 1 756 187描述了在聚酯聚氨酯中使用基于聚酯醇的聚合物多元醇。作为大量聚酯聚合物多元醇的更高粘度的结果，这些体系显著更难加工。此外，EP 1 790 675和EP 1 756 187公开了在聚酯醇聚氨酯体系中使用基于聚醚醇的聚合物多元醇。这些文献教导了使用醚聚合物多元醇对泡沫形态具有不利影响。
WO 03/099899描述了使用聚合物改性的多异氰酸酯生产聚氨酯模制品如鞋底，其中将优选数均分子量为15000-90000g/mol的树脂状热塑性乙烯基聚合物用作聚合物改性剂，其中仅提到了基于一种或多种基于苯乙烯或取代苯乙烯的乙烯基芳族单体和任选其他烯属不饱和单体如丙烯腈的聚合物。尽管所得聚氨酯模制品具有高硬度，但它们难以加工和收缩，这导致更低质量的整体泡沫。
US 4283500描述了一种其中将基于聚丙烯腈的聚合物用作聚合物的聚合物/多异氰酸酯组合物。该聚合物/多异氰酸酯组合物可以用于生产任何聚氨酯且得到高弯曲模量和高抗压模量。没有描述聚氨酯整体泡沫和所得模制品缺乏尺寸稳定性的问题。
US 4772658描述了一种聚合物/多异氰酸酯组合物，对其也使用不含碳二亚胺的多异氰酸酯和含羟基的烯属不饱和单体的加合物制备聚合物。该聚合物/多异氰酸酯组合物可以用于生产任何聚氨酯且导致所得聚氨酯的高热稳定性。没有包括聚氨酯泡沫的实例。没有描述聚氨酯整体泡沫和所得模制品缺乏尺寸稳定性的问题。
因此，本发明的目的是提供一种生产聚氨酯整体泡沫的方法，所述整体泡沫不收缩或者仅不显著地收缩并且具有优异性能如硬度、拉伸强度和抗撕裂传播性。
本发明的该目的惊人地由如下一种方法解决，其中将a)包含多异氰酸酯和脂族热塑性聚合物的溶液与b)多元醇、c)发泡剂以及任选d)扩链剂和/或交联剂、e)催化剂和f)其他助剂和/或添加剂混合而得到反应混合物，将该反应混合物置于模具中并使其反应而得到聚氨酯泡沫模制品。
对本发明而言，聚氨酯整体泡沫是按照DIN 7726具有外部区的聚氨酯泡沫，该外部区由于成型工艺而具有比芯高的密度。在芯和外部区上平均的总体泡沫密度为80-800g，优选100-500g/l，特别优选120-400gl，尤其是150-300g/l。
用于本发明溶液a)中的脂族热塑性聚合物是具有线性或支化链结构、可溶于(有机)溶剂中且具有在使用温度以上的流动转变范围的聚合物。此外，脂族热塑性聚合物对本发明而言基本不含芳族成分，如芳族成分。此时“基本不含芳族成分”是指芳族基团在该热塑性聚合物中的含量小于20重量%，优选小于10重量%，特别优选小于5重量%，甚至更优选小于1重量%，尤其是在该脂族热塑性聚合物中不含芳族基团，在每种情况下基于该脂族热塑性聚合物的总重量。对本发明而言，该脂族热塑性聚合物包括由至少4个相同或不同单体单元构成且分子量至少为500g/mol的聚合物。该脂族热塑性聚合物优选由至少6个，尤其是至少10个单体单元构成。此外，该脂族热塑性聚合物优选具有至少1000g/mol，尤其是至少5000g/mol的分子量。在特别优选的实施方案中，重均分子量大于20000g/mol，尤其大于50000g/mol。多异氰酸酯和脂族热塑性聚合物的溶液优选基本没有基于苯乙烯和/或丙烯腈作为单体结构单元的聚合物。此时“基本没有基于苯乙烯和/或丙烯腈作为单体结构单元的聚合物”是指苯乙烯和/或丙烯腈的含量基于溶解在异氰酸酯中的聚合物总重量小于20重量%，优选小于10重量%，特别优选小于5重量%，甚至更优选小于1重量%，尤其是没有苯乙烯和/或丙烯腈包含在该脂族热塑性聚合物中。
可以使用的脂族热塑性聚合物优选为丙烯酸或甲基丙烯酸的C1-C20酯的均聚物，例如聚(甲基)丙烯酸甲酯、聚(甲基)丙烯酸乙酯、聚(甲基)丙烯酸丙酯或聚(甲基)丙烯酸丁酯，丙烯酸或甲基丙烯酸的C1-C20酯的共聚物，例如与如下单体的共聚物：羟基丙烯酸酯和羟基甲基丙烯酸酯如丙烯酸羟乙基酯、甲基丙烯酸羟乙基酯、丙烯酸羟丙基酯、甲基丙烯酸羟丙基酯、丙烯酸羟丁基酯、甲基丙烯酸羟丁基酯、甲基丙烯酸羟戊基酯、甲基丙烯酸羟戊基酯、丙烯酸羟己基酯、甲基丙烯酸羟己基酯，丙烯酸或甲基丙烯酸，丙烯酸或甲基丙烯酸的C1-C20酯，丙烯酸或甲基丙烯酸与基于氧化乙烯和/或氧化丙烯的多元醇的酯，马来酸或马来酸酐、巴豆酸、富马酸、衣康酸、丙烯酰胺、N,N-二甲基丙烯酰胺、N,N-二苄基丙烯酰胺、N-丁基丙烯酰胺、甲基丙烯酰基甲酰胺和类似衍生物；乙烯基酯、乙烯基醚、乙烯基酮等等，例如乙酸乙烯酯、丁酸乙烯酯、乙酸异丙烯酯、甲酸乙烯酯、丙烯酸乙烯基酯、甲氧基乙酸乙烯酯、乙烯基甲基醚、乙烯基丙基醚、乙烯基丁基醚、乙烯基2-乙基己基醚、乙烯基2-甲氧基乙基醚、甲氧基丁二烯、乙烯基2-丁氧基乙基醚、2,4-二氢-1,2-吡喃、2-丁氧基乙基2’-乙烯氧基乙基醚、乙烯基甲基酮、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、乙烯基咪唑或季化乙烯基咪唑、二乙烯基亚砜、二乙烯基砜、乙烯基磺酸钠、乙烯基磺酸甲酯、N-乙烯基吡咯、乙烯基膦酸酯和类似衍生物；富马酸二甲酯、马来酸二甲酯、衣康酸单甲酯、甲基丙烯酸叔丁基氨基乙酯、甲基丙烯酸二甲氨基乙酯、丙烯酸缩水甘油酯或甲基丙烯酸缩水甘油酯、烯丙醇、衣康酸的二醇单酯、丁二烯或异戊二烯、乙烯或丙烯或乙烯基吡咯烷酮或乙酸乙烯酯的均聚物和/或与上述单体之一的共聚物。脂族热塑性聚合物特别优选选自(甲基)丙烯酸的C1-C20酯的均聚物、(甲基)丙烯酸的C1-C20酯的共聚物、丁二烯共聚物、聚乙烯基吡咯烷酮或乙烯基吡咯烷酮共聚物、聚乙酸乙烯酯或乙酸乙烯酯共聚物或者两种或更多种这些脂族热塑性聚合物的混合物。
为了生产本发明的溶液a)，将脂族热塑性聚合物溶于多异氰酸酯中。作为多异氰酸酯，可以使用任何对生产聚氨酯已知的多异氰酸酯。这些包括由现有技术已知的脂族、脂环族和芳族双官能或多官能异氰酸酯以及其任何混合物。实例是二苯基甲烷-2,2’-、2,4’-和4,4’-二异氰酸酯(MDI)或环氢化类似化合物，单体二苯基甲烷二异氰酸酯和具有不止两个环的二苯基甲烷二异氰酸酯的同系物(聚合MDI)的混合物，异佛尔酮二异氰酸酯(IPDI)或其低聚物，甲苯-2,4-或2,6-二异氰酸酯(TDI)或其混合物，四亚甲基二异氰酸酯或其低聚物，六亚甲基异氰酸酯(HDI)或其低聚物，萘二异氰酸酯(NDI)或其混合物。
优选使用芳族二异氰酸酯和/或多异氰酸酯，即每分子具有至少两个异氰酸酯基团的异氰酸酯，其中异氰酸酯基团直接键合于芳族体系上。作为芳族异氰酸酯，优选使用4,4’-MDI、2,2’-MDI、2,4’-MDI、聚合MDI和/或TDI以及这些异氰酸酯的混合物，特别优选4,4’-MDI、2,2’-MDI、2,4’-MDI、聚合MDI。特别优选包含在多异氰酸酯中的4,4’-MDI可以包括一定比例的二氮杂环丁二酮(uretdione)-、脲基甲酸酯-或二氮杂环丁酮亚胺(uretonimine)改性的多异氰酸酯。
多异氰酸酯还可以以多异氰酸酯预聚物的形式使用。这些多异氰酸酯预聚物可以通过使过量的上述多异氰酸酯与多元醇例如在30-120°C，优选约80°C的温度下反应以形成预聚物而得到。作为多元醇可以使用所有在b)下描述的多元醇。
任选地也可以在该反应中加入扩链剂以形成该多异氰酸酯预聚物。作为该预聚物的扩链剂，可以使用所有也在c)下描述的扩链剂。合适的扩链剂例如为二元醇，例如二丙二醇、三丙二醇和/或二丙二醇与氧化烯，优选氧化丙烯、氧化乙烯和/或其混合物的加合物。
若使用多异氰酸酯预聚物，则所用多异氰酸酯优选具有大于5重量%，特别优选大于7.5重量%的异氰酸酯含量。
作为溶液a)，尤其可以使用聚甲基丙烯酸甲酯和MDI的溶液；聚(甲基丙烯酸甲酯-co-丙烯酸羟乙基酯)和MDI的溶液；聚(甲基丙烯酸甲酯-co-甲基丙烯酸羟乙基酯)和MDI的溶液；聚(甲基丙烯酸甲酯-co-丙烯酸)和MDI的溶液；聚(甲基丙烯酸甲酯-co-甲基丙烯酸)和MDI的溶液；聚(甲基丙烯酸甲酯-co-丙烯酸丁酯)和MDI的溶液；聚(甲基丙烯酸甲酯-co-甲基丙烯酸丁酯)和MDI的溶液；聚(甲基丙烯酸甲酯-co-丙烯酸乙基己基酯)和MDI的溶液，聚(甲基丙烯酸甲酯-co-甲基丙烯酸羟乙基酯-co-丙烯酸乙基己基酯)和MDI的溶液；聚(甲基丙烯酸甲酯-co-乙烯基咪唑)与MDI的溶液；聚(甲基丙烯酸甲酯-co-季化乙烯基咪唑)和MDI的溶液；聚甲基丙烯酸甲酯和MDI的溶液；聚甲基丙烯酸丁酯和MDI的溶液；聚(甲基丙烯酸甲酯-co-甲基丙烯酸月桂基酯)和MDI的溶液；聚乙酸乙烯酯和MDI的溶液；聚乙烯基吡咯烷酮和MDI的溶液；聚(乙烯基吡咯烷酮-co-乙酸乙烯酯)和MDI的溶液；聚(甲基丙烯酸甲酯-co-丙烯酸羟乙基酯)和PMDI的溶液；聚(甲基丙烯酸甲酯-co-甲基丙烯酸羟乙基酯)和PMDI的溶液；聚(甲基丙烯酸甲酯-co-丙烯酸)和PMDI的溶液；聚(甲基丙烯酸甲酯-co-甲基丙烯酸)和PMDI的溶液；聚(甲基丙烯酸甲酯-co-丙烯酸丁酯)和PMDI的溶液；聚(甲基丙烯酸甲酯-co-甲基丙烯酸丁酯)和PMDI的溶液；聚(甲基丙烯酸甲酯-co-丙烯酸乙基己基酯)和PMDI的溶液，聚(甲基丙烯酸甲酯-co-甲基丙烯酸羟乙基酯-co-丙烯酸乙基己基酯)和PMDI的溶液；聚(甲基丙烯酸甲酯-co-乙烯基咪唑)与PMDI的溶液；聚(甲基丙烯酸甲酯-co-季化乙烯基咪唑)和PMDI的溶液；聚甲基丙烯酸甲酯和PMDI的溶液；聚甲基丙烯酸丁酯和PMDI的溶液；聚(甲基丙烯酸甲酯-co-甲基丙烯酸月桂基酯)和PMDI的溶液；聚乙酸乙烯酯和PMDI的溶液；聚乙烯基吡咯烷酮和PMDI的溶液；聚(乙烯基吡咯烷酮-co-乙酸乙烯酯)和PMDI的溶液，或与TDI、MDI、PMDI或HDI的混合物的溶液。
本发明溶液优选基本不含其他溶剂。对本发明而言，溶剂是所有传统溶剂，但不为该异氰酸酯或该脂族热塑性聚合物本身。“基本不含其他溶剂”是指本发明所用溶液a)基于溶液a)的总重量包含小于2重量%，特别优选小于0.5重量%，尤其小于0.01重量%的溶剂。优选在不加入溶剂来生产溶液a)且在用于生产溶液a)的起始组分中不包含溶剂。由于该生产方法而包含在用于生产溶液a)的起始组分中的溶剂残留物不在该限制之下。同样，多异氰酸酯本身或脂族热塑性聚合物本身不考虑为该限制的溶剂。
为了生产溶液a)，将脂族热塑性聚合物和多异氰酸酯混合并任选加热。优选在混合之后将该混合物加热至20-200°C，特别优选30-150°C，尤其是60-120°C的温度。
除了多异氰酸酯和脂族热塑性聚合物外，溶液a)优选基于溶液(a)的总重量包含小于5重量%，特别优选小于2重量%，尤其是小于1重量%的其他材料。
脂族热塑性聚合物在溶液a)中的比例基于多异氰酸酯和脂族热塑性聚合物的总重量优选为0.1-50重量%，特别优选0.5-30重量%，尤其是1-20重量%。
生产溶液a)的另一方法是将脂族热塑性聚合物的单体溶解在该异氰酸酯中并随后通过自由基机理将这些聚合。此时可以使用传统自由基引发剂。单体在该异氰酸酯中的比例对应于该脂族热塑性聚合物的将来浓度。
溶液a)作为稳定的清澈溶液存在。此时“清澈溶液”是指在将脂族热塑性聚合物溶于多异氰酸酯中之后溶液a)在80°C和1cm路径长度下的透射改变与纯异氰酸酯相比小于50%。清澈溶液优选为按照DIN ISO15715:2003测量的福尔马肼浊度值小于200FTU(FTU=福尔马肼浊度单位)的溶液。该溶液优选具有小于100FTU，特别优选小于50FTU的福尔马肼浊度值。
溶液a)优选在25°C下具有小于110000mPas，特别优选小于75000mPas，尤其优选小于50000mPas的零剪切粘度。
本发明的溶液a)优选具有大于5重量%，特别优选大于7.5重量%的NCO含量。
作为多元醇b)可以使用所有常用于聚氨酯化学中的多元醇。用于本发明目的的多元醇是所有分子量为至少500g/mol且每分子具有至少两个对异氰酸酯呈反应性的氢原子的化合物。这些包括常规聚醚醇和聚酯醇。
聚醚醇通过已知方法制备，例如由一种或多种在亚烷基中具有2-4个碳原子的氧化烯使用碱金属氢氧化物或碱金属醇盐作为催化剂并加入至少一种以键合形式包含2或3个反应性氢原子的起始剂分子通过阴离子聚合制备或者使用路易斯酸如五氯化锑或醚合氟化硼通过阳离子聚合制备。合适的氧化烯例如为四氢呋喃、1,3-氧化丙烯、1,2-或2,3-氧化丁烯以及优选氧化乙烯和1,2-氧化丙烯。也可以将已知为DMC催化剂的多金属氰化物用作催化剂。氧化烯可以单独、依次交替或者作为混合物使用。优选1,2-氧化丙烯和氧化乙烯的混合物，其中氧化乙烯以10-50%的量作为氧化乙烯端嵌段(“EO封端”)使用，从而使得形成的多元醇具有大于70%的伯OH端基。
可能的起始剂分子是水或二元和三元醇，如乙二醇、1,2-和1,3-丙二醇、二甘醇、二丙二醇、1,4-丁二醇、甘油或三羟甲基丙烷。
聚醚多元醇，优选聚氧丙烯-聚氧乙烯多元醇优选具有的官能度为2-3且分子量为1000-8000g/mol，优选2000-6000g/mol。
聚酯多元醇例如可以由具有2-12个碳原子的有机二羧酸，优选具有4-6个碳原子的脂族二羧酸和具有2-12个碳原子，优选2-6个碳原子的多元醇，优选二醇制备。可能的羧酸例如为琥珀酸、戊二酸、己二酸、辛二酸、壬二酸、癸二酸、癸烷二甲酸、马来酸、富马酸、邻苯二甲酸、间苯二甲酸和对苯二甲酸。二羧酸可以单独或者相互混合使用。代替游离二羧酸，还可以使用相应的二羧酸衍生物，例如具有1-4个碳原子的醇的二羧酸酯或二羧酸酐。优选使用重量比例如为20-35:35-50:20-32的琥珀酸、戊二酸和己二酸的二羧酸混合物，尤其是己二酸。二元和多元醇，尤其是二醇的实例是乙二醇、二甘醇、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、甘油和三羟甲基丙烷。优选使用乙二醇、二甘醇、1,4-丁二醇、1,5-戊二醇和1,6-己二醇。还可以使用衍生于内酯，例如ε-己内酯或羟基羧酸，如ω-羟基己酸的聚酯多元醇。
为了制备聚酯多元醇，可以在没有催化剂存在下或者优选在酯化催化剂存在下，有利的是在惰性气体如氮气、一氧化碳、氦气、氩气等的气氛中，在熔体中在150-250°C，优选180-220°C的温度下，任选在减压下使例如芳族和优选脂族有机多羧酸和/或其衍生物与多元醇缩聚至优选小于10，特别优选小于2的所需酸值。在优选实施方案中，使酯化混合物在上述温度下在大气压力以及随后在小于500毫巴，优选50-150毫巴的压力下缩聚至酸值为80-30，优选40-30。可能的酯化催化剂例如为金属、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，缩聚还可以在液相中在稀释剂和/或夹带剂如苯、甲苯、二甲苯或氯苯存在下进行以共沸蒸除缩合的水。为了制备聚酯多元醇，有机多羧酸和/或其衍生物与多元醇有利地以1:1-1.8，优选1:1.05-1.2的摩尔比缩聚。
所得聚酯多元醇优选具有的官能度为2-4，尤其是2-3且分子量为500-5000g/mol，优选1000-3000g/mol。
其他合适的具有至少两个对异氰酸酯呈反应性的氢原子的较高分子量化合物b)是聚合物改性的多元醇，优选聚合物改性的聚酯醇或聚醚醇，特别优选接枝聚醚醇或接枝聚酯醇。这些为通常含有5-60重量%，优选10-55重量%，特别优选30-55重量%，尤其是40-50重量%优选为热塑性的聚合物的聚合物多元醇。这些聚合物聚酯醇例如描述于WO 05/098763和EP-A-250351中且通常通过合适的烯属单体，例如苯乙烯、丙烯腈、(甲基)丙烯酸酯、(甲基)丙烯酸和/或丙烯酰胺在用作接枝基质的聚酯醇中自由基聚合而制备。侧链通常通过增长的聚合物链的自由基向聚酯醇或聚醚醇转移而形成。该聚合物多元醇除了接枝共聚物外还主要包括分散在不变的聚酯醇或聚醚醇中的烯烃的均聚物。
在优选实施方案中，将丙烯腈、苯乙烯、丙烯腈和苯乙烯用作单体，特别优选仅将苯乙烯用作单体。单体任选在其他单体、大分子单体、调节剂存在下使用自由基引发剂，通常为偶氮或过氧化物化合物在作为连续相的聚酯醇或聚醚醇中聚合。该方法例如描述于DE 111 394、US 3 304 273、US 3 383 351、US 3 523 093、DE 1 152 536和DE 1 152 537中。
在自由基聚合过程中，将大分子单体掺入共聚物链中。这导致形成具有聚酯或聚醚嵌段和聚(丙烯腈-苯乙烯)嵌段的嵌段共聚物，其在连续相和分散相的界面中起相相容剂的作用并抑制聚合物聚酯醇颗粒的附聚。大分子单体的比例基于用于制备该聚合物多元醇的单体总重量为1-20重量%。
若在多元醇b)中包含聚合物多元醇，则这优选与其他多元醇，例如聚醚醇、聚酯醇或聚醚醇和聚酯醇的混合物一起存在。聚合物多元醇的比例基于组分b)的总重量特别优选大于5重量%。该聚合物多元醇特别优选为聚合物聚酯醇或聚合物聚醚醇。
作为多元醇b)，优选使用包含聚酯醇和任选聚合物聚酯醇的混合物，特别优选仅使用聚酯醇和/或聚合物聚酯醇。
此外，在聚氨酯整体泡沫的生产中存在发泡剂c)。这些发泡剂c)可以包括水。作为发泡剂c)不仅可以使用水，此外还可以使用通常已知起化学和/或物理作用的化合物。化学发泡剂是通过与异氰酸酯反应形成气态产物的化合物，例如水或甲酸。物理发泡剂是溶解或乳化在聚氨酯生产用原料中并在聚氨酯形成条件下汽化的化合物。这些例如为烃类、卤代烃类和其他化合物，例如全氟化链烷烃如全氟己烷、氯氟烃类和醚类、酯类、酮类、缩醛类或其混合物，例如具有4-8个碳原子的(环)脂族烃类或氟代烃类如来自Solvay Fluorides LLC的
365mfc。在优选实施方案中，将包含这些发泡剂中的至少一种和水的混合物用作发泡剂；尤其将水用作唯一发泡剂。若不将水用作发泡剂，则优选仅使用物理发泡剂。
在优选实施方案中，水的含量基于组分a)-f)的总重量为0.1-2重量%，优选0.2-1.5重量%，特别优选0.3-1.2重量%，尤其是0.4-1重量%。
在另一优选实施方案中，将包含物理发泡剂的中空微球作为额外发泡剂加入组分a)、b)和任选d)的反应。中空微球也可以与上述发泡剂混合使用。
中空微球通常包含热塑性聚合物的壳且在芯中填充基于链烷烃的低沸点液态物质。该类中空微球的生产例如描述于US 3 615 972中。中空微球通常具有5-50μm的直径。合适中空微球的实例可以以商品名
由Akzo Nobel得到。
中空微球基于组分b)、c)和d)的总重量通常以0.5-5重量%的量加入。
作为扩链剂和/或交联剂d)使用分子量优选小于500g/mol，特别优选60-400g/mol的物质，其中扩链剂具有2个对异氰酸酯呈反应性的氢原子且交联剂具有3个对异氰酸酯呈反应性的氢原子。这些可以单独使用或者优选以混合物形式使用。优选使用分子量小于400，特别优选60-300，尤其是60-150的二醇和/或三醇。例如可能的是具有2-14个，优选2-10个碳原子的脂族、脂环族和/或芳脂族二醇，例如乙二醇，1,3-丙二醇，1,10-癸二醇，1,2-、1,3-、1,4-二羟基环己烷，二甘醇，二丙二醇以及优选1,4-丁二醇、1,6-己二醇和二(2-羟基乙基)氢醌，三醇如1,2,4-、1,3,5-三羟基环己烷、甘油和三羟甲基丙烷，以及基于氧化乙烯和/或1,2-氧化丙烯的低分子量含羟基聚氧化烯和作为起始剂分子的上述二醇和/或三醇。特别优选使用单乙二醇、1,4-丁二醇、甘油或其混合物，尤其是单乙二醇或包含单乙二醇的混合物作为扩链剂d)。
若使用扩链剂、交联剂或其混合物，则这些有利地基于组分b)和d)的重量以1-60重量%，优选1.5-50重量%，尤其是2-40重量%的量使用。
作为生产聚氨酯泡沫的催化剂e)，优选使用强力促进组分b)和任选c)的含羟基化合物与a)中的多异氰酸酯反应的化合物。例如可以提到脒类，如2,3-二甲基-3,4,5,6-四氢嘧啶，叔胺如三乙胺、三丁胺、二甲基苄基胺、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、二(二甲氨基乙基)醚、二(二甲氨基丙基)脲、二甲基哌嗪、1,2-二甲基咪唑、1-氮杂双环[3.3.0]辛烷和优选1,4-二氮杂双环[2.2.2]辛烷以及链烷醇胺如三乙醇胺、三异丙醇胺、N-甲基二乙醇胺、N-乙基二乙醇胺和二甲基乙醇胺。同样可以使用有机金属化合物，优选有机锡化合物如有机羧酸的锡(II)盐，例如乙酸锡(II)、辛酸锡(II)、乙基己酸锡(II)和月桂酸锡(II)，以及有机羧酸的二烷基锡(IV)盐，例如二乙酸二丁基锡、二月桂酸二丁基锡、马来酸二丁基锡和二乙酸二辛基锡，还有羧酸铋如新癸酸铋(III)、2-乙基己酸铋和辛酸铋或其混合物。有机金属化合物可以单独使用或者优选与强碱性胺组合使用。若组分b)之一为酯，则优选仅使用胺催化剂。
优选基于组分b)的重量使用0.001-5重量%，尤其是0.05-2重量%的催化剂或催化剂组合。
任选地也可以将助剂和/或添加剂f)加入生产聚氨酯泡沫的反应混合物中。例如可以提到表面活性物质、泡沫稳定剂、泡孔调节剂、脱模剂、橡胶硫化助剂、填料、染料、颜料、水解抑制剂、臭味吸收物质和抑制真菌和/或抑制细菌的物质。
可能的表面活性物质例如为用于帮助均化原料并且任选也适合调节泡孔结构的化合物。例如可以提到乳化剂如蓖麻油硫酸或脂肪酸的钠盐，还有脂肪酸与胺的盐，如二乙基胺油酸盐、二乙醇胺硬脂酸盐、二乙醇胺蓖麻醇酸盐，磺酸的盐，例如十二烷基苯磺酸或二萘基甲烷二磺酸的碱金属或铵盐，以及蓖麻油酸；泡沫稳定剂如硅氧烷-氧化烯共聚物和其他有机聚硅氧烷，乙氧基化烷基酚，乙氧基化脂肪醇，石蜡油，蓖麻油酯或蓖麻油酸酯，土耳其红油和花生油，以及泡孔调节剂如石蜡、脂肪醇和二甲基聚硅氧烷。具有聚氧化烯和氟代链烷烃基团作为侧基的低聚丙烯酸酯也适合改善乳化作用、泡孔结构和/或稳定该泡沫。表面活性物质基于100重量份组分(b)通常以0.01-5重量份的量使用。
合适脱模剂的实例是脂肪酸酯与多异氰酸酯的反应产物、包含氨基的聚硅氧烷与脂肪酸的盐、具有至少8个碳原子的饱和或不饱和(环)脂族羧酸与叔胺的盐以及尤其是内部脱模剂如通过将褐煤酸和至少一种具有至少10个碳原子的脂族羧酸的混合物用分子量为60-400g/mol的至少双官能链烷醇胺、多元醇和/或多胺酯化或酰胺化而制备的羧酸酯和/或羧酰胺，例如如EP 153 639所公开，有机胺、硬脂酸金属盐和有机单羧酸和/或二羧酸或其酸酐的混合物，例如如DE-A-3 607 447所公开，或者亚氨基化合物、羧酸金属盐和任选羧酸的混合物，例如如US 4 764 537所公开。
填料，尤其增强填料是本身已知的常规有机和无机填料、增强材料、填充剂、涂料组合物等。具体实例是无机填料如硅质矿物，例如片状硅酸盐如叶蛇纹石、膨润土、蛇纹石、角闪石、闪石、纤蛇纹石和滑石，金属氧化物如高岭土、铝氧化物、钛氧化物、氧化锡和铁氧化物，金属盐如白垩和重晶石，以及无机颜料如硫化镉、硫化锌，还有玻璃等。优选使用高岭土(陶土)、硅酸铝以及硫酸钡和硅酸铝的共沉淀，还有天然和合成纤维状矿物如硅灰石，金属纤维，尤其是各种长度的玻璃纤维，它们可以任选用施胶剂涂敷。可能的有机填料例如为碳黑、蜜胺、松香、环戊二烯基树脂和接枝聚合物，还有纤维素纤维、聚酰胺、聚丙烯腈、聚氨酯和基于芳族和/或脂族二羧酸酯的聚酯纤维，以及尤其是碳纤维。
无机和有机填料可以单独使用或者作为混合物使用并且有利地基于组分a)-c)的重量以0.5-50重量%，优选1-40重量%的量加入反应混合物中，但天然和合成纤维的垫、非织造织物和机织物的含量可以达到至多80重量%的值。
作为增塑剂和水解抑制剂，例如可以使用γ-丁内酯或有机碳酸酯。
为了生产本发明的聚氨酯整体泡沫，以使得来自a)的异氰酸酯的NCO基团与组分b)、c)和d)的反应性氢原子之和的当量比为1:0.8-1:1.25，优选1:0.9-1:1.15的量将组分a)-f)相互混合。
本发明的聚氨酯整体泡沫优选通过一步法借助低压或高压技术在密闭、有利地加热的模具中生产。模具通常包括金属，例如铝或钢。这些方法例如由Piechota和
在“Integralschaumstoff”，Carl-Hanser-Verlag，Munich，Vienna，1975或“Kunststoff-Handbuch”，第7卷，Polyurethane，第3版，1993，第7章中所述。
为此，优选将起始组分a)-f)在15-90°C，特别优选25-55°C的温度下混合并任选在超计大气压力下将该混合物引入密闭模具中。混合可以借助搅拌器或搅拌螺杆机械地进行或在高压下以逆流注入方法进行。模具温度有利地为20-160°C，优选30-120°C，特别优选30-60°C。对本发明而言，组分a)-f)的混合物在反应转化率基于异氰酸酯基团小于90%下称为反应混合物。
计算引入模具中的反应混合物量以使所得整体泡沫模制品的密度为80-800g，优选100-500g/l，特别优选120-400g，尤其是150-300g。生产本发明聚氨酯整体泡沫的密实度为1.1-8.5，优选1.5-7.0，特别优选1.9-6。
本发明进一步提供了一种可以由本发明方法得到的聚氨酯整体泡沫。其显示出高尺寸稳定性，即泡沫在模具中或在脱模后不收缩。本发明的聚氨酯整体泡沫优选用作鞋底，例如用于户外鞋(straβenschuhe)、运动鞋、凉鞋和长筒靴，但也用于汽车内饰领域，例如用作方向盘、头枕或变速器把手，或用作椅子的扶手或用作摩托车车座。本发明的聚氨酯整体泡沫特别优选用作尤其用于低密度中底(zwischensohlen)的鞋底或用作轻质外底。此时发现溶液a)的使用对脂族热塑性聚合物，尤其对泡孔尺寸分布和尺寸稳定性以及机械性能如硬度、拉伸强度、伸长率和抗撕裂传播性发挥积极影响，这使得可以在机械性能相同下降低密度。
本发明下面借助实施例说明。
所用原料：
MMA：Aldrich的甲基丙烯酸甲酯
EHA：Aldrich的丙烯酸乙基己基酯
HEMA：Aldrich的甲基丙烯酸羟乙基酯
MEK：Aldrich的甲基乙基酮
V65：Wako的偶氮引发剂
多元醇1：基于己二酸、单乙二醇、二甘醇和三羟甲基丙烷且OH值为44mg KOH/g的聚酯醇
多元醇2：基于己二酸、单乙二醇和丁二醇且OH值为56mg KOH/g的聚酯醇
多元醇3：Synthesia的聚合物聚酯醇Hoopol PM
多元醇4：基于己二酸、单乙二醇、丁二醇和三羟甲基丙烷且OH值为48mg KOH/g的聚酯醇
多元醇5：Synthesia的聚合物聚酯醇Hoopol PM
多元醇6：基于己二酸、单乙二醇、二甘醇和甘油且OH值为61mgKOH/g的聚酯醇
多元醇7：基于己二酸、单乙二醇、二甘醇和甘油且OH值为60mgKOH/g的聚酯醇
KV 1：单乙二醇
KV 2：二丙二醇
Cross 1：三乙醇胺
KAT 1：BASF的N 203
KAT 2：在二丙二醇中的二(2-二甲氨基乙基醚)
KAT 3：Air Products的Catalyst XD 103
KAT 4：1-甲基咪唑
Stabi 1：GE Silicones的Niax Silicone L-1540
Stabi 2：Degussa的
BF 2370
Stabi 3：Air Products的
LK 221
Stabi 4：Momentive的
Silicone SR 234
Ad 1：Akzo Nobel的
051 DU 40
MDI 1：BASF Polyurethanes的
MES(4,4’-MDI)
MDI 2：BASF Polyurethanes GmbH的
MM103(4,4’-MDI和碳二亚胺改性的4,4’-MDI的混合物)
MDI 3：BASF Polyurethanes GmbH的
MI(2,4’-MDI和4,4’-MDI的混合物)
BH：BASF SE的H(六亚甲基二异氰酸酯)
HS：水解抑制剂
BC：苯甲酰氯
聚合物1：聚(甲基丙烯酸甲酯-co-丙烯酸乙基己基酯)
聚合物2：聚(甲基丙烯酸甲酯-co-甲基丙烯酸羟乙基酯)
聚合物3：Lucite International的基于甲基丙烯酸甲酯和甲基丙烯酸月桂基酯的
2552聚合物，重均分子量Mw为75000g/mol
聚合物4：Lucite International的基于甲基丙烯酸甲酯和甲基丙烯酸的
4055聚合物，重均分子量为5500g/mol
聚合物5：Lucite International的
2044，聚甲基丙烯酸丁酯，重均分子量Mw为142000g/mol
聚合物6：Lucite International的基于甲基丙烯酸甲酯和甲基丙烯酸的
2008聚合物，重均分子量Mw为37000g/mol
聚合物7：Aldrich的聚甲基丙烯酸甲酯Mw 120000g/mol
聚合物8：Aldrich的聚(苯乙烯-co-丙烯腈)，重均分子量Mw=165000g/mol且数均分子量Mn=68000g/mol
聚合物合成
聚合物1：合成聚(甲基丙烯酸甲酯-co-丙烯酸乙基己基酯)
将100g甲基乙基酮(MEK)、15g丙烯酸乙基己基酯和15g甲基丙烯酸甲酯(MMA)放入装有温度计、桨叶搅拌器、氮气吹管和滴液漏斗的500ml四颈烧瓶中，与50mg Wako V-65混合并加热至68°C。在达到该温度之后，在2小时内引入70g MMA并在每种情况下在1小时后加入1.5ml 1.25gWako V65在50ml MEK中的溶液。在加料完成后，将该混合物在68°C下进一步搅拌1小时，然后加入40ml 1.25g Wako V65在50ml MEK中的溶液。然后将该混合物加热至75°C并在75°C下再搅拌2小时。将该混合物冷却至室温，加入100g MEK，然后通过在水中沉淀而将该聚合物分离并在75°C和减压下干燥至恒重。
产物通过IR和NMR光谱法表征且用于进一步合成。
实施例2：合成聚(甲基丙烯酸甲酯-co-甲基丙烯酸羟乙基酯)
溶液1包含99g MMA、1g甲基丙烯酸羟乙基酯和100g MEK
溶液2包含1.25g Wako V65和50ml MEK
将10g溶液1、1ml溶液2和150g MEK置于装有温度计、桨叶搅拌器、氮气吹管和滴液漏斗的500ml四颈烧瓶中并加热至65°C。在达到该温度之后，在2小时内引入溶液1并在每种情况下在1小时后引入1.5ml溶液2。在加料完成后，将该混合物在65°C下进一步搅拌1小时，然后引入40ml溶液2。然后将该混合物加热至75°C并在75°C下再搅拌2小时。将该混合物冷却至室温，然后通过在水中沉淀而将该聚合物分离并在75°C和减压下干燥至恒重。
产物通过IR和NMR光谱法以及凝胶渗透色谱法表征且用于进一步合成。GPC表明重均分子量为42000g/mol。
含有试验E1-E5的表1表明脂族热塑性聚合物在各种异氰酸酯中的溶解性。对于这一目的，在每种情况下将5g聚合物5、6或7加入所示异氰酸酯中并在搅拌的同时加热至80°C。
表1：
| 试验 | 聚合物 | 异氰酸酯 | 溶解性 |
| E1 | 聚合物5 | MDI 3 | + |
| E2 | 聚合物6 | MDI 3 | + |
| E3 | 聚合物7 | MDI 3 | + |
| E4 | 聚合物7 | MDI 2 | + |
| E5 | 聚合物7 | BH | + |
+完全可溶；-不可溶
可见在实施例E1-E5中脂族热塑性聚合物完全溶解在异氰酸酯中。
下表中所列配制剂说明预聚物的制备。这经由均匀程序进行。首先将MDI 1和MDI 2置于装有搅拌器、温度计和氮气入口管的合适烧瓶中并加热至60°C的温度。在该温度下首先将BC加入异氰酸酯的混合物中。然后加入多元醇(多元醇2和多元醇4)与水解抑制剂HS的混合物并将该混合物在60°C下搅拌1小时，然后加热至80°C的温度并在80°C下搅拌2小时。在ISO 2-ISO 5的情况下，加入聚合物1、聚合物3或聚合物8并将该混合物搅拌直到形成清澈溶液，然后加入多元醇的混合物中。所用原料示于表2中。
表2：制备预聚物：
| ISO 1(C) | ISO 2(E) | ISO 3(E) | ISO 4(E) | 1505(C) | |
| MDI 1 | 53.999 | 53.999 | 52.940 | 52.426 | 53.997 |
| MDI 2 | 8.000 | 8.000 | 7.843 | 7.767 | 8.000 |
| HS | 1.000 | 1.000 | 0.980 | 0.971 | 1.000 |
| BC | 0.003 | 0.001 | 0.001 | 0.001 | 0.003 |
| 多元醇2 | 27.000 | 24.000 | 26.471 | 26.214 | 24.000 |
| 多元醇4 | 10.000 | 10.000 | 9.804 | 9.709 | 10.000 |
| 聚合物1 | - | 3.000 | - | - | |
| 聚合物3 | - | - | 1.961 | 2.913 | |
| 聚合物8 | 3.000 | ||||
| NCO预聚物 | 18.9 | 18.8 | 18.5 | 18.4 | 19.0 |
所得预聚物进一步按表3加工并且在每种情况下均自由发泡且引入鞋底模具中以形成密度为300g/l的模制品。
表3：
| 对比例C1 | E6 | E7 | E8 | C2 | |
| 多元醇1 | 32.40 | 32.40 | 32.40 | 32.40 | 32.40 |
| 多元醇2 | 41.66 | 41.66 | 41.66 | 41.66 | 41.66 |
| 多元醇3 | 6.94 | 6.94 | 6.94 | 6.94 | 6.94 |
| 多元醇4 | 4.63 | 4.63 | 4.63 | 4.63 | 4.63 |
| KV 1 | 7.41 | 7.41 | 7.41 | 7.41 | 7.41 |
| KAT 1 | 0.60 | 0.60 | 0.60 | 0.60 | 0.60 |
| KAT 2 | 0.06 | 0.06 | 0.06 | 0.06 | 0.06 |
| KAT 3 | 1.67 | 1.67 | 1.67 | 1.67 | 1.67 |
| Stabi 1 | 0.42 | 0.42 | 0.42 | 0.42 | 0.42 |
| Stabi 2 | 0.42 | 0.42 | 0.42 | 0.42 | 0.42 |
| Stabi 3 | 0.28 | 0.28 | 0.28 | 0.28 | 0.28 |
| Ad 1 | 2.78 | 2.78 | 2.78 | 2.78 | 2.78 |
| 水 | 0.74 | 0.74 | 0.74 | 0.74 | 0.74 |
| 指数 | 94 | 94 | 94 | 94 | 94 |
| 预聚物 | ISO 1 | ISO 2 | ISO 3 | ISO 4 | ISO 5 |
24小时后检测自由发泡泡沫和模制品的收缩。表4显示了评价结果：
表4
| C1 | E6 | E7 | E8 | C2 | |
| 自由发泡 | -- | ++ | + | ++ | -- |
| 模制品 | -- | ++ | ++ | ++ | -- |
--强烈收缩；-收缩；+很少有任何收缩；++不收缩
由实施例E6-E8可见，溶解在预聚物中的聚甲基丙烯酸甲酯共聚物导致所得聚氨酯的更好尺寸稳定性。使用溶解在预聚物中的聚(苯乙烯-co-丙烯腈)共聚物并不导致尺寸稳定性的任何改进。
除了尺寸稳定性的改进外，使用溶解在预聚物中的特定聚合物还可能导致所得聚氨酯泡沫的机械性能改进。为了说明这一点，如表5所示制备异氰酸酯预聚物ISO 6-ISO 10：
表5
| ISO 6(C) | ISO 7(C) | ISO 8(E) | ISO 9(E) | ISO 10(E) | |
| MDI 1 | 61.347 | 66.997 | 61.100 | 66.983 | 66.495 |
| MDI 2 | 9.000 | 6.000 | 9.000 | 5.999 | 6.000 |
| HS | 0.65 | - | 0.65 | - | - |
| BC | 0.001 | 0.003 | 0.01 | 0.01 | 0.003 |
| KV 2 | - | - | - | 2.000 | - |
| 多元醇2 | 10.000 | - | 10.000 | - | - |
| 多元醇6 | 19.000 | - | 14.240 | - | - |
| 多元醇7 | - | 27.000 | - | 11.999 | 24.499 |
| 聚合物2 | - | - | 5.000 | - | - |
| 聚合物4 | - | - | - | 12.999 | 3.000 |
| NCO预聚物 | 22.0 | 23 | 21.9 | 22.3 | 22.8 |
预聚物通过均匀程序制备。首先将MDI 1和MDI 2置于装有搅拌器、温度计和氮气入口管的合适烧瓶中并加热至60°C的温度。在该温度下将BC加入异氰酸酯的混合物中。然后加入多元醇的混合物并将该混合物在60°C下搅拌1小时，然后加热至80°C的温度并在80°C下搅拌2小时。在ISO 8-ISO 10的情况下，加入聚合物2或聚合物4并将该混合物搅拌直到形成清澈溶液，然后加入多元醇的混合物。
将制备的异氰酸酯预聚物ISO 6-ISO 10在试验C3和C4以及E9-E11中与表6所示多元醇组分在94的异氰酸酯指数下混合并在每种情况下自由发泡以确定自由泡沫密度以及还引入尺寸为20cm*20cm*1cm的模具中以生产用于测定机械性能的测试板。
表6
| C3 | C4 | E9 | E10 | E11 | |
| 多元醇2 | 62.91 | 84.80 | 62.91 | 84.80 | 84.80 |
| 多元醇3 | 27.64 | - | 27.64 | - | - |
| 多元醇5 | - | 5.00 | - | 5.00 | 5.00 |
| KV 1 | 6.89 | 7.50 | 6.89 | 7.50 | 7.50 |
| Cross 1 | 0.37 | - | 0.37 | - | - |
| Kat 1 | 1.29 | 1.30 | 1.29 | 1.30 | 1.30 |
| Kat 4 | - | 0.20 | - | 0.20 | 0.20 |
| Stabi 4 | 0.09 | - | 0.09 | - | - |
| 水 | 0.77 | 1.20 | 0.77 | 1.20 | 1.20 |
| 指数 | 94 | 94 | 94 | 94 | 94 |
| 预聚物 | ISO 6 | ISO 7 | ISO 8 | ISO 9 | ISO 10 |
所得聚氨酯整体泡沫的反应特性和性能示于表7中。
表7：
由实施例可见，使用聚甲基丙烯酸甲酯共聚物导致剖层撕裂的改进和更高硬度。
Claims (11)
1.一种生产密度为80-800g/l的聚氨酯整体泡沫的方法，其中将
a)包含多异氰酸酯和脂族热塑性聚合物的溶液与
b)多元醇，
c)发泡剂以及任选
d)扩链剂和/或交联剂，
e)催化剂和
f)其他助剂和/或添加剂混合而得到反应混合物，将所述反应混合物引入模具中并使其反应而得到聚氨酯泡沫模制品。
2.根据权利要求1的方法，其中所述溶液a)基本不含其他溶剂。
3.根据权利要求1或2的方法，其中脂族热塑性聚合物在所述溶液a)中的比例基于溶液a)的总重量为0.1-50重量%。
4.根据权利要求1-3中任一项的方法，其中所述多异氰酸酯为芳族二异氰酸酯和/或多异氰酸酯。
5.根据权利要求1-4中任一项的方法，其中所述溶液a)具有至少5重量%的NCO含量。
6.根据权利要求1-5中任一项的方法，其中所述脂族热塑性聚合物选自(甲基)丙烯酸的C1-C20酯的均聚物、(甲基)丙烯酸的C1-C20酯的共聚物、丁二烯共聚物、聚乙烯基吡咯烷酮和乙烯基吡咯烷酮共聚物、聚乙酸乙烯酯和乙酸乙烯酯共聚物或这些脂族热塑性聚合物中两种或更多种的混合物。
7.根据权利要求1-6中任一项的方法，其中将聚酯用作多元醇。
8.根据权利要求1-7中任一项的方法，其中所述多元醇b)包括聚合物多元醇。
9.根据权利要求1-7中任一项的方法，其中所述聚氨酯整体泡沫具有的密度为100-500g/l。
10.一种可以根据权利要求1-8中任一项得到的聚氨酯整体泡沫。
11.根据权利要求9的聚氨酯整体泡沫，其中所述聚氨酯整体泡沫为鞋底、方向盘、变速器把手、摩托车车座或扶手。
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP10165724.5 | 2010-06-11 | ||
| EP10165724A EP2395038A1 (de) | 2010-06-11 | 2010-06-11 | Polyurethanintegralschaumstoffe mit guter Dimensionsstabilität und hoher Härte |
| PCT/EP2011/059396 WO2011154406A1 (de) | 2010-06-11 | 2011-06-07 | Polyurethanintegralschaumstoffe mit guter dimensionsstabilität |
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| Country | Link |
|---|---|
| EP (2) | EP2395038A1 (zh) |
| CN (1) | CN103025783B (zh) |
| WO (1) | WO2011154406A1 (zh) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111763416A (zh) * | 2020-06-23 | 2020-10-13 | 中交上海三航科学研究院有限公司 | 抗水分散型聚氨酯硬质泡沫注浆止水加固材料及制备方法 |
| CN112771092A (zh) * | 2018-09-28 | 2021-05-07 | 汉高知识产权控股有限责任公司 | 聚乙酸乙烯酯聚合物或共聚物用于增加双组分可固化聚合物体系的异氰酸酯组分的粘度的用途 |
| CN113906074A (zh) * | 2019-05-16 | 2022-01-07 | 巴斯夫欧洲公司 | 具有高剖层撕裂的低密度聚氨酯泡沫系 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115181230B (zh) * | 2022-08-19 | 2023-10-31 | 盛鼎高新材料有限公司 | 一种嵌段共聚聚氨酯弹性体的制备方法 |
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Also Published As
| Publication number | Publication date |
|---|---|
| EP2580263A1 (de) | 2013-04-17 |
| EP2395038A1 (de) | 2011-12-14 |
| EP2580263B1 (de) | 2017-10-11 |
| CN103025783B (zh) | 2015-11-25 |
| WO2011154406A1 (de) | 2011-12-15 |
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