CN104755523A - 基于乙烯基酯聚氨酯树脂的树脂混合物及其应用 - Google Patents
基于乙烯基酯聚氨酯树脂的树脂混合物及其应用 Download PDFInfo
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- CN104755523A CN104755523A CN201380055671.1A CN201380055671A CN104755523A CN 104755523 A CN104755523 A CN 104755523A CN 201380055671 A CN201380055671 A CN 201380055671A CN 104755523 A CN104755523 A CN 104755523A
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Abstract
本发明公开了具有乙烯基酯聚氨酯树脂作为基础树脂的树脂混合物,其中所述的乙烯基酯聚氨酯树脂可通过(i)双脱水己糖醇化合物与二异氰酸酯反应,及随后(ii)将所得到的产物与羟基取代的(甲基)丙烯酸反应获得。所述基础树脂的优点在于,其可完全由基于可再生原料的原料化合物获得。此外,此树脂混合物适合作为粘结剂用于反应性树脂组合物,通过其可提供化学固定体系。
Description
技术领域
本发明涉及具有基于可再生原料的乙烯基酯聚氨酯树脂,特别是基于双脱水己糖醇的乙烯基酯聚氨酯树脂作为基础树脂的树脂混合物,含有该树脂混合物的反应性树脂灰浆以及其用于化学固定的应用。
背景技术
基于可自由基固化化合物作为粘结剂的反应性树脂灰浆的应用早已熟知。在固定技术领域,已经实现树脂混合物作为有机粘结剂用于化学固定技术,例如作为销接组合物使用。此处指的是接合组合物,其作为多组分体系配制,其中一种组分包含树脂混合物,另一种组分包含固化性试剂。其他常规的成分,例如溶剂包括反应性溶剂(反应性稀释剂)可以包含在所述一种组分中和/或所述另一种组分中。通过混合这两种组分,然后通过自由基形成,引发固化反应即聚合反应,且所述的树脂固化为热固性塑料。作为可自由基固化化合物经常(特别是用于化学固定技术)使用乙烯基酯树脂和不饱和聚酯树脂。
由于其有利的特性,乙烯基酯树脂(特别是乙烯基酯聚氨酯树脂)用作基础树脂,其可通过单体或聚合物型的芳族二异氰酸酯和羟基取代的甲基丙烯酸酯如甲基丙烯酸羟烷基酯获得。例如EP0713015 B1描述了具有不饱和聚酯树脂,乙烯基酯树脂包括乙烯基酯聚氨酯树脂作为基础树脂的销接组合物。这种体系的化合物基于经典石油化学,其中原料从化石原料源,如石油获得。
众所周知,化石原料源,如石油,不是取之不尽的,且在某个时候将枯竭。对于化石原料源的可获得性降低的情况存在危险,即对于化学固定体系提出的高要求必需的化合物也许不再可获得。
因此,将来需求具有来自可再生原料的高含量碳的基于可再生原料的替代体系,以便将来也进一步能够提供高度专业化的化学固定体系。
发明内容
因此本发明的目的在于,提供一种用于化学固定技术的反应性树脂灰浆,其树脂组分包含基础树脂和任选的其他成分(如反应性稀释剂),其具有非常高含量的来自可再生原料的碳。
这个目的通过使用基于双脱水己糖醇化合物的乙烯基酯聚氨酯树脂作为基础树脂解决。这样的优点在于,为了合成基础树脂可以追溯至原料化合物,其可以由可再生原料以足够的数量和质量获得。
为了更好地理解本发明,本文中所使用的术语的以下解释被视为是合理的。本发明中指的是:
-“基础树脂”是纯的,固化性的或可固化的化合物,其自身或采用反应试剂例如固化性试剂、促进剂等(不包含在基础树脂中)通过聚合反应固化;所述的可固化化合物可以是单体、二聚物、低聚物和预聚物;
-“树脂母料”是合成后(没有分离基础树脂)基础树脂的制备产物,其可能包含反应性稀释剂、稳定剂和催化剂(也称为合成溶液);
-“树脂混合物”是指由树脂母料和促进剂以及稳定剂和任选的其他反应性稀释剂组成的混合物;此术语与术语“有机粘结剂”同义使用;
-“反应性树脂灰浆”是由树脂混合物和无机附加料组成的混合物;此处术语“A组分”同义使用;
-“固化性试剂”是导致基础树脂聚合(固化)的物质;
-“固化剂”是由固化性试剂和有机和/或无机附加料组成的混合物;此处术语“B组分”同义使用;
-“促进剂”是能够促进聚合反应(固化)的化合物,其用于促进自由基引发剂的形成;
-“阻聚剂”是能够抑制聚合反应(固化)的化合物,其一次性(einmal)用于避免聚合反应以及由此避免自由基可聚合化合物在贮存期间的过早发生的不期望的聚合,其中这些化合物通常以如此少量使用,使得凝胶时间不被影响;另一方面,阻聚剂用于延迟加入固化性试剂后立即发生的聚合反应,其中这些化合物通常以这样的量使用,即使得凝胶时间受影响;
-“反应性稀释剂”是液态的或低粘度的基础树脂,其稀释其他基础树脂、树脂母料或树脂混合物,并由此提供其应用时所需的粘度,包含能与基础树脂反应的官能团,且在聚合(固化)时以主要部分成为经固化组合物(灰浆)的成分;
-“凝胶时间”用于其通常采用过氧化物固化的不饱和聚酯树脂或乙烯基树脂,树脂的固化阶段的时间对应于凝胶时间,其中树脂的温度由+25℃升高至+35℃。这大致对应于这样的时间段,其中树脂的流动性或粘度仍然处于一定范围,所述的反应性树脂或反应性树脂组合物仍然能够容易地加工或处理;
-“胶凝时间漂移”(对于特别选择的时间段,例如30或60天),指的是这种现象,当固化的时间点与固化的参考物标准时间点不同,例如在制备反应性树脂或反应性树脂组合物后的24小时时,所观察到的凝胶时间偏离参考物的时间点;
-“灰浆组合物”指的是一种制剂,其除了反应性树脂组合物还含有其它有机和/或无机填料,并且其可以原样直接用于化学固定;
-“双组分灰浆体系”指的是一种体系,其包括组分A(反应性树脂灰浆)和组分B(固化剂),其中所述的两种组分分开存放以抑制反应,使得反应性树脂灰浆的固化仅在其混合之后发生;
-“(甲基)丙烯酸.../...(甲基)丙烯酸...”是指“甲基丙烯酸.../...甲基丙烯酸...”以及“丙烯酸.../…丙烯酸....”-化合物都应当被包括;
-“乙烯基酯聚氨酯”是指乙烯基酯,其仲羟基在聚加成反应中与多异氰酸酯反应,由此生成氨酯桥;
-“可再生原料”指的是原料,特别是植物或动物来源的有机物质,其全部或部分地作为原料用于工业,并且其不同于化石原料是生物可再生的,即适当(überschaubar)的时间段内可更新;包括非矿物或非化石原料,其可以用于工业或工商业加工工艺;
-“冷固化”是指该树脂混合物和反应性树脂灰浆可以在室温下完全固化。
反应性树脂灰浆通常通过如下方式制备:用于制备基础树脂所需的原料化合物任选地与催化剂和溶剂,特别是反应性稀释剂一起加入反应器中并相互反应。反应结束后并且任选地已经开始反应时,为了贮存稳定性而将阻聚剂添加至反应混合物中,由此得到所谓的树脂母料。向树脂母料中经常加入促进剂用于基础树脂固化,任选地其他阻聚剂(其可以与用于贮存稳定性的阻聚剂相同或不同),用以调节凝胶时间,且任选地其他溶剂(特别是反应性稀释剂),由此获得树脂混合物。向这种树脂混合物中掺混无机和/或有机附加料以用于调节各种性能,如基础树脂的流变学和浓度,由此获得反应性树脂灰浆。
优选的树脂混合物相应地含有至少一种基础树脂,至少一种反应性稀释剂,至少一种促进剂,至少一种阻聚剂。反应性树脂灰浆除了包含上述的树脂混合物还包含无机和/或有机的附加料,其中特别优选无机附加料,如以下更详细地描述的那些。
本发明基于如下构思:提供一种含有基础树脂的树脂混合物,所述基础树脂可以由生物质组成的原料化合物以及因而可以由可再生原料制备。相应地,原料化合物依据其潜能进行选择,可由可再生原料获得。
本发明的第一主题涉及具有乙烯基酯聚氨酯树脂作为基础树脂的树脂混合物,其中所述的乙烯基酯聚氨酯树脂可通过(i)双脱水己糖醇化合物与二异氰酸酯反应,及随后的(i i)将所得到的产物与羟基取代的(甲基)丙烯酸反应获得。
令人惊奇地成功实现,在基于双脱水己糖醇的乙烯基酯聚氨酯树脂作为基础树脂的基础上提供反应性树脂灰浆,其具有可接受的连接头承载能力,因而其适合例如作为有机粘结剂用于化学固定技术。
根据本发明,通常作为原料化合物用于乙烯基酯聚氨酯树脂合成所使用的二异氰酸酯通过二羟基化合物与二异氰酸酯反应获得,使得所述产物必然在分子末端具有异氰酸酯基和在分子主链上具有两个氨基甲酸酯基团。适宜地,每摩尔二羟基化合物使用至少两摩尔二异氰酸酯,使得每种情况下所述二异氰酸酯的一个异氰酸酯基与二羟基化合物的一个羟基反应形成氨酯基团。但是优选二异氰酸酯以稍微过量加入,以基本上防止低聚。所述的异氰酸酯端基在每种情况下与一个羟基取代的(甲基)丙烯酸酯反应。
为了原料化合物可以由可再生原料获得,二羟基化合物根据本发明是一种双脱水己糖醇化合物。双脱水己糖醇化合物,更确切地说1,4:3,6-双脱水己糖醇化合物,是淀粉工业的副产物。它们可以例如通过D-己糖醇脱水获得,而D-己糖醇又可通过简单还原己糖获得。所述的双脱水己糖醇化合物因而是可以由生物质获得的手性产物。根据两个羟基的构型,区分为三种异构体(异山梨醇(结构A),异甘露醇(结构B)和异艾杜醇(结构C)),其可通过由D-葡萄糖、D-甘露糖或L-果糖进行氢化和后续双脱水得到。
用作原料使用的双脱水己糖醇化合物因而可以是异山梨醇,异甘露醇,或异艾杜醇,或者可以是这些双脱水己糖醇化合物的混合物。下文中因而术语“双脱水己糖醇化合物”应理解为各自独立的化合物以及各种单独化合物的任何混合物。由于异山梨醇是最广泛分布的,因此其优选作为原料化合物用于与二异氰酸酯反应。
所述的双脱水己糖醇化合物和其制备方法本身是已知的,并且相应的产物可在市场上购得。
为了二异氰酸酯也可以由可再生原料获得,适宜地,二异氰酸酯是脂族二异氰酸酯,如四亚甲基二异氰酸酯,六亚甲基二异氰酸酯或十亚甲基二异氰酸酯。
四亚甲基二异氰酸酯的应用具有的优点是,其可由植物来源的C4-母体结构单元,即琥珀酸获得(Chemical Engineering&Technology Special Issue:原料变化,第31卷,第5期,第647页(2008),文章“琥珀酸:用于来自可再生资源的生物基聚合物的新化学平台”,I.Bechthold,K.Bretz,S Kabasci,R.Kopitzky和A.Springer)。作者认为琥珀酸是将来的基础化学品之一,其可由可再生原料获得。
此外,目前也可由可再生原料获得六亚甲基二异氰酸酯(HDMI),因为根据美国专利US 8,421,879相应的前体(己二酸)可从生物质获得。
十亚甲基二异氰酸酯的应用同样具有的优点是,其可由植物来源的C10-母体结构单元(即癸二酸)获得。可由生物基蓖麻油获得的C10-母体结构单元在文献中有详细描述(European Journal of LipidScience and Technology,特刊:油和脂肪作为可再生资源用于化学工业,第112卷,第1期,第10页(2010年),文章“蓖麻油作为可再生资源用于化工行业”,Hatice Mutlu和Michael A.R.Meier)。作者还在此认为,蓖麻油是非常有价值的用于化学工业的可再生原料的来源。
然而,此外,其它可由可再生原料获得的二异氰酸酯也可以根据本发明使用,例如来自脂肪酸或其它来源的二异氰酸酯,如WO2011/098272 A2中所述。
羟基取代的(甲基)丙烯酸酯也可以由可再生原料获得。特别是其涉及脂族(甲基)丙烯酸羟烷基酯,如(甲基)丙烯酸羟丙基酯或(甲基)丙烯酸羟乙基酯,其中甲基丙烯酸酯化合物是特别优选的。
用于合成甲基丙烯酸羟丙酯所需的丙二醇可以由甘油获得(CEPmagazine.org,www.aiche.org/cep(2007年8月),SuzanneShelley的文章“得到丙二醇的可再生途径”)。甘油是制备生物柴油的主要的副产物。因此,对于制备丙二醇,它是常规原料的廉价的,可持续和环保的替代品,其可由石油获得。
用于合成甲基丙烯酸羟乙基酯所需的乙二醇同样可以由原料如环氧乙烷和它们的衍生物,例如二醇类(其可从生物质如糖蜜(Molasse)或甘蔗获得)获得。
所述的甲基丙烯酸C2-和C3-羟烷基酯可在市场上购得。
此外,然而,还有其它可由可再生原料获得的羟基取代的(甲基)丙烯酸酯可以根据本发明使用。
特别优选的基础树脂具有下式:
其中n为4,6或10,R是氢或甲基。
如果所有原料化合物由可再生原料(如生物质)获得,且为了制备树脂混合物,制备由乙烯基酯聚氨酯树脂在甲基丙烯酸羟丙基酯或甲基丙烯酸羟乙基酯中构成的65重量%的溶液,则树脂混合物的最高至80%的碳含量可以来源于可再生原料。
在本发明的一个优选的实施方案中,所述的树脂混合物含有其它低粘度,可自由基聚合化合物,优选可以由可再生原料获得的那些,作为反应性稀释剂,以在必要时,例如在制备乙烯基酯聚氨酯树脂或其前体时适应性调节其粘度。所述的反应性稀释剂可以以基于树脂混合物计的90至10重量%,优选70至30重量%加入。在此方面,参见WO 09/156648 A1,WO 10/061097 A1,WO 10/079293 A1和WO10/099201 A1,其中的内容在此结合入本申请。
所述的树脂混合物可另选含有任何适合的反应性稀释剂。适宜地,所述的树脂组合物包含脂族或芳族C5-C15(甲基)丙烯酸酯作为反应性稀释剂,其中特别优选(甲基)丙烯酸酯,其选自(甲基)丙烯酸羟丙基酯、1,2-乙二醇二(甲基)丙烯酸酯、1,3-丙二醇二(甲基)丙烯酸酯、1,2-丁二醇二(甲基)丙烯酸酯、1,4-丁二醇二(甲基)丙烯酸酯、三羟甲基丙烷三(甲基)丙烯酸酯、(甲基)丙烯酸苯乙基酯、(甲基)丙烯酸四氢糠基酯、乙基三甘醇(甲基)丙烯酸酯、(甲基)丙烯酸N,N-二甲基氨基乙基酯、(甲基)丙烯酸N,N-二甲基氨基甲基酯、(甲基)丙烯酸乙酰乙酰氧乙基酯、(甲基)丙烯酸异冰片基酯、(甲基)丙烯酸2-乙基己基酯、二乙二醇二(甲基)丙烯酸酯、甲氧基聚乙二醇单(甲基)丙烯酸酯、(甲基)丙烯酸酯三甲基环己基、(甲基)丙烯酸2-羟乙基酯、(甲基)丙烯酸二环戊烯基氧乙基酯和/或三环戊二烯基二(甲基)丙烯酸酯、双酚A-(甲基)丙烯酸酯、酚醛清漆环氧基二(甲基)丙烯酸酯、二-[(甲基)丙烯酰基-马来酰基]三环-5.2.1.0.2,6-癸烷、二环戊烯基氧乙基巴豆酸酯、3-(甲基)丙烯酰氧甲基-三环5.2.1.0.2,6-癸烷、3-(甲基)环戊二烯基(甲基)丙烯酸酯、(甲基)丙烯酸异冰片基酯和萘烷基(Decalyl)-2-(甲基)丙烯酸酯;PEG-二(甲基)丙烯酸酯,如PEG200二(甲基)丙烯酸酯、四乙二醇二(甲基)丙烯酸酯、(甲基)丙烯酸丙酮缩甘油(Solketal)酯,(甲基)丙烯酸环己基酯、苯氧基乙基二(甲基)丙烯酸酯、(甲基)丙烯酸甲氧基乙基酯,(甲基)丙烯酸四氢糠基酯、(甲基)丙烯酸叔丁基酯和(甲基)丙烯酸降冰片基酯。原则上,还可以使用其它常用的可自由基聚合化合物,单独或与(甲基)丙烯酸酯混合使用,例如苯乙烯,α-甲基苯乙烯,烷基化苯乙烯,如叔丁基苯乙烯,二乙烯基苯和烯丙基化合物,其中所述其中的可由基于可再生原料的基础化学品获得的那些是优选的。
为了稳定化而对抗过早的聚合反应(存贮稳定性),以及为了调节凝胶时间和反应性,所述的树脂混合物可以包含阻聚剂。为了确保存贮稳定性,所述的阻聚剂优选以基于树脂混合物计0.0005至2重量%,更优选0.01至1重量%的量存在。为了调节凝胶时间和反应性,所述的树脂混合物可额外包含0.005至3重量%,优选0.05至1重量%的阻聚剂。
根据本发明,对于可自由基聚合的化合物通常所使用的阻聚剂适合作为所述阻聚剂,如本领域技术人员熟知的那些。
为了稳定化而对抗过早的聚合反应,所述的树脂混合物和反应性树脂灰浆通常包含阻聚剂,如氢醌,取代的氢醌,例如4-甲氧基苯酚,吩噻嗪,苯醌或叔丁基邻苯二酚(如例如在EP1935860 A1或EP 0965619A1中所描述),稳定的硝酰基自由基,也称为N-氧基自由基,如哌啶基-N-氧基或四氢吡咯-N-氧基,例如在DE 19531649 A1中所描述的那些。特别优选4-羟基-2,2,6,6-四甲基哌啶-N-氧基(以下称为Tempol)用于稳定化,其具有的优点是由此还可以调节凝胶时间。
优选所述的阻聚剂选自酚类化合物和非酚类化合物,如稳定的自由基和/或吩噻嗪。
作为经常是商业自由基固化性的反应性树脂的组分的酚类阻聚剂,可考虑酚类,如2-甲氧基苯酚、4-甲氧基苯酚、2,6-二叔丁基-4-甲基苯酚、2,4-二叔丁基苯酚、2,6-二-叔丁基苯酚、2,4,6-三甲基苯酚、2,4,6-三(二甲基氨基甲基)苯酚、4,4'-硫代双(3-甲基-6-叔丁基苯酚)、4,4'-异亚丙基二苯酚、6,6'-二叔丁基-4,4'-双(2,6-二-叔丁基苯酚)、1,3,5-三甲基-2,4,6-三(3,5-二叔丁基-4-羟基苄基)苯、2,2'-亚甲基-二-对甲酚、邻苯二酚和丁基邻苯二酚,如4-叔丁基邻苯二酚、4,6-二-叔-丁基邻苯二酚、氢醌类,如氢醌、2-甲基氢醌、2-叔丁基氢醌、2,5-二叔丁基氢醌、2,6-二叔丁基氢醌、2,6-二甲基氢醌、2,3,5-三甲基氢醌、苯醌、2,3,5,6-四氯-1,4-苯醌、甲基苯醌、2,6-二甲基苯醌、萘醌、或以上物质中两种或更多种的混合物。
作为非酚类阻聚剂优选考虑吩噻嗪类,如吩噻嗪和/或其衍生物或它们的组合,或稳定的有机自由基,如加尔万氧基自由基和N-氧基自由基。
适合的稳定的N-氧基自由基(硝酰基自由基)可以选自1-氧基-2,2,6,6-四甲基哌啶、1-氧基-2,2,6,6-四甲基哌啶-4-醇(也称为TEMPOL)、1-氧基-2,2,6,6-四甲基哌啶-4-酮(也称为TEMPON)、1-氧基-2,2,6,6-四甲基-4-羧基-哌啶(也称为4-羧基-TEMPO)、1-氧基-2,2,5,5-四甲基吡咯烷、1-氧基-2,2,5,5-四甲基-3-羧基吡咯烷(也称为3-羧基-PROXYL)、铝-N-亚硝基苯基羟胺、二乙基羟胺,如在DE 199 56 509中所述。此外适合的N-氧基化合物是肟类如乙醛肟、丙酮肟、甲基乙基酮肟、水杨酸肟、苯并肟、乙二肟、二甲基乙二肟、丙酮-O-(苄氧羰基)肟等。此外,在羟基基团对位取代的嘧啶醇化合物或吡啶醇化合物可以,如在未在先公开的专利申请DE102011077248 B1中所描述的,作为稳定剂使用。
取决于所期望的树脂混合物的特性和用途,所述的阻聚剂可以单独或者作为其中两种或更多种的组合使用。酚类和非酚类阻聚剂的组合在此可以实现协同作用,以及显示基本上无偏差的调节反应性树脂制剂的凝胶时间的调节。
优选的是,树脂成分的固化采用自由基引发剂(如过氧化物)引发。除了自由基引发剂,还可以使用促进剂。由此获得快速固化性的反应性树脂灰浆,其是冷固化的,即其在室温下固化。通常加入到树脂混合物中的适合的促进剂是本领域技术人员公知的。这些例如是胺,优选叔胺和/或金属盐。
适合的胺选自以下化合物,例如在申请US 2011071234 A1中所描述的那些:二甲胺、三甲胺、乙胺、二乙胺、三乙胺、正丙胺、二正丙胺、三正丙胺、异丙胺、二异丙胺、三异丙胺、正丁胺、异丁胺、叔丁胺、二正丁胺、二异丁胺、三异丁胺、戊胺、异戊胺、二异戊胺、己胺、辛胺、十二烷基胺、月桂胺、硬脂胺、氨基乙醇、二乙醇胺、三乙醇胺、氨基己醇、乙氧基氨基乙烷、二甲基-(2-氯乙基)胺、2-乙基己胺、双(2-氯乙基)胺、2-乙基己胺、双(2-乙基己基)胺、N-甲基硬脂胺、二烷基胺、乙二胺、N,N'-二甲基乙二胺、四甲基乙二胺、二亚乙基三胺、全甲基二亚乙基三胺、三亚乙基四胺、四亚乙基五胺、1,2-二氨基丙烷、二亚丙基三胺、三亚丙基四胺、1,4-二氨基丁烷、1,6-二氨基己烷、4-氨基-1-二乙基氨基戊烷、2,5-二氨基-2,5-二甲基己烷、三甲基六亚甲基二胺、N,N-二甲基氨基乙醇、2-(2-二乙基氨基乙氧基)乙醇、双(2-羟乙基)油基胺、三[2-(2-羟基-乙氧基)乙基]胺、3-氨基-1-丙醇、甲基-(3-氨基丙基)醚、乙基-(3-氨基丙基)醚、1,4-丁二醇-双(3-氨基丙基醚)、3-二甲基氨基-1-丙醇、1-氨基-2-丙醇、1-二乙基氨基-2-丙醇、二异丙醇胺、甲基-双-(2-羟丙基)胺、三-(2-羟丙基)胺、4-氨基-2-丁醇、2-氨基-2-甲基丙醇、2-氨基-2-甲基丙二醇、2-氨基-2-羟甲基丙二醇、5-二乙基(Aiethyl)氨基-2-戊酮、3-甲基氨基丙腈、6-氨基己酸、11-氨基十一烷酸、6-氨基己酸乙酯、11-氨基己酸异丙基酯、环己胺、N-甲基环己胺、N,N-二甲基环己胺、二环己胺、N-乙基环己胺、N-(2-羟乙基)环己胺、N,N-双(2-羟乙基)环己胺、N-(3-氨基丙基)-环己胺、氨基甲基环己烷、六氢甲苯胺、六氢苄胺、苯胺、N-甲基苯胺、N,N-二甲基苯胺、N,N-二乙基苯胺、N,N-二丙基苯胺、异丁基苯胺、甲苯胺、二苯基胺、羟乙基苯胺、双(羟乙基)苯胺、氯苯胺、氨基苯酚、氨基苯甲酸及其酯、苄胺、二苄胺、三苄胺、甲基二苄胺、α-苯乙胺,二甲苯胺、二异丙基苯胺、十二烷基苯胺、氨基萘、N-甲基氨基萘、N,N-二甲基氨基萘、N,N-二苄基萘、二氨基环己烷、4,4'-二氨基二环己基甲烷、二氨基二甲基二环己基甲烷、苯二胺、苯二甲二胺、二氨基联苯、萘二胺、甲苯胺、联苯胺、2,2-双(氨基苯基)丙烷、氨基苯甲醚、氨基苯硫酚、氨基二苯基醚、氨基甲酚、吗啉、N-甲基吗啉、N-苯基吗啉、羟乙基吗啉、N-甲基吡咯烷、吡咯烷、哌啶、羟乙基哌啶、吡咯、吡啶、喹啉、吲哚、假吲哚、咔唑、吡唑、咪唑、噻唑、嘧啶、喹喔啉、氨基吗啉、二吗啉乙烷、[2,2,2]-二氮杂二环辛烷和N,N-二甲基-对-甲苯胺。
优选的胺是苯胺衍生物和N,N-二烷基芳胺,如N,N-二甲基苯胺、N,N-二乙基苯胺、N,N-二甲基-对甲苯胺、N,N-双(羟烷基)芳基胺、N,N-双(2-羟乙基)苯胺、N,N-双(2-羟乙基)甲苯胺、N,N-双(2-羟丙基)苯胺、N,N-双(2-羟丙基)甲苯胺、N,N-双(3-甲基丙烯酰基-2-羟丙基)-对甲苯胺、N,N-二丁氧基羟丙基-对甲苯胺和4,4'-双(二甲基氨基)二苯基甲烷。
聚合物型胺类,如通过由N,N-双(羟烷基)苯胺与二羧酸的缩聚反应或通过由环氧乙烷在这些胺上的聚加成获得的那些,也适合作为促进剂。
适合的金属盐是,例如辛酸钴或环烷酸钴,以及羧酸钒、羧酸钾、羧酸钙、羧酸铜、羧酸锰或羧酸锆。
如果使用促进剂,则其以基于所述的树脂混合物计0.01至10重量%,优选为0.2至5重量%的量使用。
本发明的另一个主题是除了上述的树脂组合物以外,还含有有机粘结剂、无机和/或有机附加料,例如填料和/或其它添加剂的反应性树脂灰浆。
反应性树脂灰浆中树脂混合物的比例优选为基于所述的反应性树脂灰浆计的10至60重量%,更优选20至30重量%。因此,附加料的比例优选为基于所述的反应性树脂灰浆计的90至40重量%,更优选为80至70重量%。
作为填料可使用常规的填料,优选矿物或类矿物填料,如石英、玻璃、砂、石英砂、石英粉、瓷、刚玉、陶瓷、滑石、硅石(如锻制二氧化硅)、硅酸盐、粘土、二氧化钛、白垩、重晶石、长石、玄武岩、氢氧化铝、花岗岩或沙岩,聚合物型填料,如热固性塑料,水硬性填料,如石膏、生石灰或水泥(例如高铝水泥或波特兰水泥),金属,例如铝、炭黑;此外,木材、矿物的或有机的纤维等,或上述物质中两种或更多种的混合物,其可作为粉末形式、以颗粒形式或以成型体的形式加入。所述的填料可以以任意形式存在,例如作为粉末或粉或作为成型体,例如以圆柱形,环形,球形,薄片状,小棒状,鞍形或晶体形式或另外以纤维形式(纤维状填料),且相应的基础颗粒优选具有10mm的最大直径。填料存在于各成分中,优选以最高至90重量%的量,特别是3至85重量%,尤其5至70重量%的量存在。但是,优选并且作用更明显增强的是球形的惰性物质(球状)。
其它可想到的添加剂还有触变剂,例如任选的经有机后处理的锻制二氧化硅、膨润土、烷基纤维素和甲基纤维素、蓖麻油衍生物等,增塑剂如苯二甲酸酯或癸二酸酯,稳定剂、抗静电剂、增稠剂、增韧剂、固化催化剂、流变助剂、润湿剂、着色添加剂如染料或特别是颜料,例如用于组分的不同着色以更好地控制其充分混合,或类似物,或上述物质中两种或更多种的混合物。还有非反应性的稀释剂(溶剂)可以,优选以基于各自的组分(反应性树脂灰浆,固化剂)计最高至30重量%(例如1至20重量%)的量存在,如低级烷基酮例如丙酮,二低级烷基-低级烷酰胺如二甲基乙酰胺,低级烷基苯如二甲苯或甲苯,苯二甲酸酯或链烷烃,或水。
在本发明的一个优选实施方案中,根据本发明的反应性树脂灰浆作为双组分或多组分体系,特别是双组分体系配制,其中所述的树脂成分和固化剂成分分开放置以抑制反应。因此,第一组分(A组分)包含反应性树脂灰浆,和第二组分(B组分)包含固化剂。由此达到了可固化化合物和固化性试剂仅在即将使用之前才彼此混合并引发固化反应。
固化剂含有固化性试剂用以引发树脂成分的聚合(固化)。如上所述,这是自由基引发剂,优选过氧化物。
本领域技术人员已知的所有用于乙烯基酯树脂固化的过氧化物都可根据本发明用于固化基于双脱水己糖醇的乙烯基酯聚氨酯树脂。这类过氧化物包括有机和无机过氧化物,无论是液体的或固体的,其中也可以使用过氧化氢。适合的过氧化物的实例是过氧化碳酸酯(式-OC(O)OO-),过氧化酯(式-C(O)OO-),二酰基过氧化物(式-C(O)OOC(O)-),二烷基过氧化物(式-OO-)等。这些可以作为低聚物或聚合物存在。广泛系列的适合的过氧化物的实例例如在申请US2002/0091214-A1,段落[0018]中进行了描述。
优选所述的过氧化物选自有机过氧化物。适合的有机过氧化物是:叔烷基氢过氧化物,如叔丁基氢过氧化物,和其它氢过氧化物,如氢过氧化异丙苯,过氧化酯或过酸,如叔丁基过酸酯、过氧化苯甲酰、过乙酸酯和过苯甲酸酯,过氧化月桂酰,包括(二)过氧化酯,过醚如过氧二乙醚,过酮如过氧化甲乙酮。作为固化剂所使用的有机过氧化物经常是叔过酸酯或叔氢过氧化物,即具有直接键合在-O-O-酰基或-OOH基团上的叔碳原子的过氧化合物。但也可根据本发明使用这些过氧化物与其它过氧化物的混合物。所述的过氧化物也可以是混合的过氧化物,即在一个分子中具有两种不同过氧化物携带单元的过氧化物。优选使用过氧化苯甲酰(BPO)用于固化。
优选双组分灰浆体系的固化剂还包含无机附加料,其中所述的附加料与可以加入反应性树脂灰浆中的那些相同。
在一个特别优选的双组分灰浆体系的实施方案中,A组分除了反应性树脂灰浆,还额外包含水硬性的或可缩聚的无机化合物,以及B组分除了固化性试剂以外还包含水。这类灰浆组合物在DE 4231161 A1中有详细描述。此处,优选A组分含有水泥作为水硬性的或可缩聚的无机化合物,例如波特兰水泥或铝酸盐水泥,其中不含氧化铁的或含低氧化铁的水泥是特别优选的。作为水硬性的无机化合物还可以使用石膏自身或者以与水泥混合的形式使用。作为可缩聚的无机化合物还可以使用硅酸盐类的可缩聚化合物,特别是可溶性的,已溶解的和/或含无定形二氧化硅的物质。
所述的双组分灰浆体系优选包括A组分和B组分,它们分开置于不同的容器中以抑制反应,例如多室的装置如多室的弹筒和/或多室的料盒(Kartusche),从这些容器中所述两种组分通过机械压力的作用或在气体压力作用下挤压出来并混合。另一种可能性在于,所述的双组分灰浆体系作为双组分胶囊配制,其被插入到钻孔并通过紧固元件的冲击旋转装入而破坏,同时灰浆组合物的所述两种组分充分混合。优选使用弹筒体系或者注射体系,其中所述两种组分从分开的容器中压出,并导引通过静态混合器,在其中将它们均匀地混合,然后通过喷嘴(优选直接)施加入钻孔。
根据本发明的树脂混合物,反应性树脂灰浆以及双组分灰浆体系可主要用于建筑领域,例如用于混凝土修补,作为聚合物混凝土,作为基于合成树脂的涂层材料或作为冷固化道路标记。其特别适合用于锚固元件,如锚栓、钢筋、螺钉等的化学固定,在钻孔中使用,特别是在各种基底中的钻孔中,特别是矿物基底,如基于混凝土、多孔混凝土、砖材(Ziegelwerk)、灰砂砖、沙岩、天然石材等那些。
下面的实施例用来进一步说明本发明。
具体实施方式
实施例:
A)树脂母料合成
A1)四亚甲基二异氰酸酯(TMDI)的应用
实施例A1.1
在500mL的三颈烧瓶中预先放入260g 1,3-丙二醇二甲基丙烯酸酯(Sarbio6200;Sartomer)和50gTMDI并且将其掺混30mg二月桂酸二辛基锡(Tegokat216;Goldschmidt Industrial ChemicalCorporation),20mg丁基羟基甲苯(BHT)以及40mg 4-羟基-2,2,6,6-四甲基哌啶-N-氧基(Tempol)。将该溶液在60℃下调温处理。然后将20g异山梨醇以20等份历时60分钟加入经搅拌的溶液中。在完成异山梨醇的加入后,将混合物加热至70℃,并在此温度下搅拌5小时。通过薄层色谱法,控制异山梨醇的反应。5小时后,异山梨醇完全反应。随后将50g甲基丙烯酸羟丙酯(HPMA)(VISIOMERHPMA98;EvonikIndustries)历时60分钟滴加入,并进一步在80℃下搅拌直至根据DIN EN 1242测定的NCO含量小于0.2%。
实施例A1.2
在500mL的三颈烧瓶中预先加入250g 1,4-丁二醇二甲基丙烯酸酯和40g TMDI,并将其掺混60mg二月桂酸二辛基锡(Tegokat216),40mg BHT以及90mg Tempol。将所述的溶液在60℃下调温处理。然后将20g异山梨醇以20等份历时60分钟加入经搅拌的溶液中。在完成异山梨醇的加入后,将混合物加热至70℃,并在此温度下搅拌5小时。通过薄层色谱法,控制异山梨醇的反应。5小时后,异山梨醇完全反应。随后将40g HPMA历时60分钟滴加入,并进一步在80℃下搅拌直至根据DIN EN 1242测定NCO含量小于0.2%。
A2)六亚甲基二异氰酸酯(HMDI)的应用
实施例A2.1
在500mL的三颈烧瓶中预先放入130g 1,3-丙二醇二甲基丙烯酸酯(Sarbio6200),130g 1,4-丁二醇二甲丙烯酸酯和50g HMDI,并将其掺混30mg二月桂酸二辛基锡(Tegokat216),20mg BHT以及40mg Tempol。所述的溶液在60℃下恒温处理。然后将20g异山梨醇以20等份历时60分钟加入经搅拌的溶液中。在完成异山梨醇的加入后,将混合物加热至70℃,并在此温度下搅拌5小时。通过薄层色谱法,控制异山梨醇的反应。5小时后,异山梨醇完全反应。随后将50g HPMA历时60分钟滴加入,并进一步在80℃下搅拌直至根据DIN EN 1242测定的NCO含量小于0.2%。
实施例A2.2
在500mL的三颈烧瓶中预先放入250g甲基丙烯酸(2,2-二甲基-1,3-二氧戊环-4-基)甲酯(甲基丙烯酸丙酮缩甘油酯)和45g HMDI,并将其掺混30mg二月桂酸二辛基锡(Tegokat216),30mg BHT以及40mg Tempol。所述的溶液在60℃下恒温处理。然后将20g异山梨醇以20等份历时60分钟加入经搅拌的溶液中。在完成异山梨醇的加入后,将混合物加热至70℃,并在此温度下搅拌5小时。通过薄层色谱法,控制异山梨醇的反应。5小时后,异山梨醇完全反应。随后将45g HPMA历时60分钟滴加入,并进一步在80℃下搅拌直至根据DIN EN 1242测定的NCO含量小于0.2%。
A3)十亚甲基二异氰酸酯(DMDI)的应用
实施例A3.1
在500mL的三颈烧瓶中预先放入230g 1,3-丙二醇二甲基丙烯酸酯(Sarbio6200)和60g DMDI,并将其掺混60mg二月桂酸二辛基锡(Tegokat216),40mg BHT以及90mg Tempol。所述的溶液在60℃下调温处理。然后将20g异山梨醇以20等份历时60分钟加入经搅拌的溶液中。在完成异山梨醇的加入后,将混合物加热至70℃,并在此温度下搅拌5小时。通过薄层色谱法,控制异山梨醇的反应。5小时后,异山梨醇反应完全。为了降低混合物的粘度,用35g甲基丙烯酸四氢糠基酯(Sarbio6100)稀释。随后将40g HPMA历时60分钟滴加入,并进一步在80℃下搅拌直至根据DIN EN 1242测定的NCO含量小于0.2%。
B)树脂混合物
B1)四亚甲基二异氰酸酯(TMDI)的应用
实施例B1.1
将根据实施例A1.1制备的380g树脂母料在50℃下与100g 1,4-丁二醇二甲基丙烯酸酯(BDDMA)以及2g叔丁基-邻苯二酚(tBBK)掺混,且随后在室温下将凝胶时间通过添加芳族胺调节至6分钟。
实施例B1.2
将根据实施例A1.2制备的350g树脂母料在50℃下与90g BDDMA以及2g tBBK掺混,且随后在室温下将凝胶时间通过添加芳族胺调节至6分钟。
B2)六亚甲基二异氰酸酯的应用
实施例B2.1
将根据实施例A2.1制备的380g树脂母料在50℃下与100g BDDMA以及2g tBBK掺混,且随后在室温下将凝胶时间通过添加芳族胺调节至6分钟。
实施例B2.2
将根据实施例A2.2制备的360g树脂母料在50℃下与90g BDDMA以及2g tBBK掺混,且随后在室温下将凝胶时间通过添加芳族胺调节至6分钟。
B3)十亚甲基二异氰酸酯的应用
实施例B3.1
将根据实施例A3.1制备的300g树脂母料在50℃下与40g BDDMA以及2g tBBK掺混,且随后在室温下将凝胶时间通过添加芳族胺调节至6分钟。
C)制备反应性树脂灰浆
为了制备混杂灰浆,将由B)具有30-45重量份的石英砂,15-25重量份的水泥和1-5重量份的锻制二氧化硅构成的树脂混合物在溶解器中混合形成均匀的灰浆组合物。
D)固化剂组分
为了制备固化剂组分,将40g过氧化二苯甲酰,250g水,25g煅制二氧化硅,5g层状硅酸盐和700g合适的粒子尺寸分布的石英粉在溶解器中混合形成均匀组合物。
将相应的反应性树脂灰浆与固化剂组分以5:1的体积比彼此混合并测量其接头承载能力。
测量失效接头应力
为了测量经固化组合物的失效接头应力,使用锚固螺杆M12,其用实施例的反应性树脂灰浆组合物销接到直径14mm和钻孔深72mm的混凝土中的钻孔中。此处涉及很好清洁过的锤钻的钻孔,其始终在20℃下固化。平均失效载荷通过从中心拨出锚固螺杆确定。每种情况下销接入5个锚固螺杆且在固化24小时后测量其负载值。此处所确定的接头负荷σ(N/mm2)作为平均值列于下表1中。
市场上具有非常高接头负荷的现有产品,例如Hilti公司的HITHY200A在可比条件下达到约30N/mm2的值。这表明,所测试的样品,特别是基于TMDI的变体C1.2,具有非常有前景的负荷特性。
Claims (16)
1.具有乙烯基酯聚氨酯树脂作为基础树脂的树脂混合物,其中所述的乙烯基酯聚氨酯树脂可通过(i)双脱水己糖醇化合物与二异氰酸酯反应,及随后(ii)将所得到的产物与羟基取代的(甲基)丙烯酸酯反应获得。
2.根据权利要求1的树脂混合物,其中每摩尔的双脱水己糖醇化合物至少与两摩尔的二异氰酸酯反应。
3.根据权利要求1或2的树脂混合物,其中每摩尔的反应(i)的产物与两摩尔的羟基取代的(甲基)丙烯酸酯反应。
4.根据前述权利要求任一项的树脂混合物,其中所述的双脱水己糖醇化合物是异山梨醇。
5.根据前述权利要求任一项的树脂混合物,其中所述的二异氰酸酯是脂族二异氰酸酯。
6.根据权利要求5的树脂混合物,其中所述的脂族二异氰酸酯是四亚甲基二异氰酸酯、六亚甲基二异氰酸酯或十亚甲基二异氰酸酯。
7.根据前述权利要求任一项的树脂混合物,其中所述的羟基取代的(甲基)丙烯酸酯是(甲基)丙烯酸羟烷基酯。
8.根据权利要求7的树脂混合物,其中所述的(甲基)丙烯酸羟烷基酯是(甲基)丙烯酸羟丙基酯或(甲基)丙烯酸羟乙基酯。
9.根据前述权利要求任一项的树脂混合物,其中所述的用于制备基础树脂的原料化合物可从可再生原料获得。
10.根据前述权利要求任一项的树脂混合物,其中最高至80%的碳来源于可再生原料。
11.反应性树脂灰浆,其包含权利要求1至10中任一项的树脂混合物,以及无机和/或有机附加料。
12.根据权利要求11的反应性树脂灰浆,其中所述附加料选自填料和添加剂。
13.根据权利要求11或12的反应性树脂灰浆,其中所述的树脂混合物以10至60重量%的量存在。
14.双组分反应性树脂灰浆体系,其包含根据权利要求11至13中任一项的反应性树脂灰浆,和固化剂。
15.根据权利要求14的双组分反应性树脂灰浆体系,其中所述固化剂包含自由基引发剂作为固化性试剂,和任选的无机和/或有机附加料。
16.根据权利要求11至13中任一项的反应性树脂灰浆用于化学固定的用途。
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DE102012219476.2 | 2012-10-24 | ||
PCT/EP2013/072018 WO2014064072A1 (de) | 2012-10-24 | 2013-10-22 | Harzmischung auf vinylesterurethanharz-basis und deren verwendung |
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CN105885004A (zh) * | 2016-06-22 | 2016-08-24 | 江南大学 | 一种生物基光固化聚氨酯及其制备的光刻胶 |
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CN110831995A (zh) * | 2017-07-03 | 2020-02-21 | 喜利得股份公司 | 包含氨基甲酸酯甲基丙烯酸酯化合物的反应性树脂、反应性树脂组分以及反应性树脂体系及其用途 |
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CN110831995B (zh) * | 2017-07-03 | 2022-11-25 | 喜利得股份公司 | 包含氨基甲酸酯甲基丙烯酸酯化合物的反应性树脂、反应性树脂组分以及反应性树脂体系及其用途 |
CN113950498A (zh) * | 2019-06-18 | 2022-01-18 | 湛新比利时股份有限公司 | 用于包覆的生物基聚氨酯(甲基)丙烯酸酯 |
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DK2912085T3 (da) | 2017-11-06 |
DE102012219476A1 (de) | 2014-04-24 |
ES2646914T3 (es) | 2017-12-18 |
US9879111B2 (en) | 2018-01-30 |
JP2015533905A (ja) | 2015-11-26 |
WO2014064072A1 (de) | 2014-05-01 |
EP2912085B1 (de) | 2017-08-09 |
US20150232610A1 (en) | 2015-08-20 |
CA2888875C (en) | 2021-02-16 |
AU2013336821A1 (en) | 2015-05-14 |
RU2650508C2 (ru) | 2018-04-16 |
RU2015119366A (ru) | 2016-12-20 |
EP2912085A1 (de) | 2015-09-02 |
CA2888875A1 (en) | 2014-05-01 |
JP6236087B2 (ja) | 2017-11-22 |
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