CN101497686A - 用于制备含异氰酸酯二聚体基团的高反应性聚氨酯组合物的干混方法 - Google Patents
用于制备含异氰酸酯二聚体基团的高反应性聚氨酯组合物的干混方法 Download PDFInfo
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- CN101497686A CN101497686A CNA2009100099444A CN200910009944A CN101497686A CN 101497686 A CN101497686 A CN 101497686A CN A2009100099444 A CNA2009100099444 A CN A2009100099444A CN 200910009944 A CN200910009944 A CN 200910009944A CN 101497686 A CN101497686 A CN 101497686A
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Abstract
本发明涉及用于制备含异氰酸酯二聚体基团的高反应性聚氨酯组合物的干混方法。具体地,本发明涉及包含异氰酸酯二聚体(Uretdion)基团的聚氨酯组合物,其可以在低温下固化,并更特别地用于聚氨酯粉末涂料和粘合剂组合物;还涉及其制备方法及其用途。
Description
技术领域
本发明涉及包含异氰酸酯二聚体(Uretdion)基团的聚氨酯组合物,其可以在低温下固化,并更特别地用于聚氨酯粉末涂料和粘合剂组合物;还涉及其制备方法及其用途。
背景技术
在室温下是固体的外部或内部封闭型多异氰酸酯对于可热交联的聚氨酯(PUR)粉末涂料和粘合剂组合物是有价值的交联剂。
例如,DE-OS 2735497记载了具有优异的气候稳定性和热稳定性的PUR粉末涂料。其制备在DE-OS 2712931中描述的交联剂由ε-己内酰胺封闭的包含异氰脲酸酯基团的异佛尔酮二异氰酸酯组成。其异氰酸酯基团被同样封闭的包含氨基甲酸酯基团、缩二脲基团或脲基团的多异氰酸酯也是已知的。
这些外部封闭体系的缺点在于在热交联反应期间封闭剂(Blockierungsmittel)的脱去。由于所述封闭剂因此被放出到环境中,出于生态学和职业卫生原因,必须采取净化废气和回收封闭剂的特殊预防措施。而且,所述封闭剂具有低反应性。需要170℃以上的固化温度。
DE-OS 3030539和DE-OS 3030572描述了用于制备包含异氰酸酯二聚体基团的加聚化合物的方法,且其末端异氰酸酯基团不可逆地被一元醇或一元胺封闭(blockieren)。缺陷特别在于,交联剂的链断裂组分导致PUR粉末涂料中的低网络密度(Networkdicht)并由此导致中度的溶剂稳定性。
EP 669353的主题是羟基封端的和包含异氰酸酯二聚体基团的加聚化合物。由于其官能度为2,其具有提高的耐溶剂性。基于这些包含异氰酸酯二聚体基团的粉末涂料组合物的共性是,在固化反应中其并不放出任何挥发性的化合物。但是,至少为180℃的烘烤温度处于高水平。
在EP 803 524中描述了在PUR粉末涂料组合物中使用脒作为催化剂。尽管这些催化剂确实导致固化温度的降低,它们仍然显示出相当大程度的发黄,这在涂料领域通常是不理想的。此发黄的原因据推测是在脒中的反应性氮原子。它们能够与大气氧反应而形成N-氧化物,这导致变色(Verfrbung)。EP 803 524还提及其它迄今用于此目的的催化剂,但是并没有指出在固化温度上的任何特别的影响。此催化剂包括聚氨酯化学中已知的有机金属催化剂,例如,二月桂酸二丁基锡(DBTL),或者还有叔胺,例如1,4-二氮杂双环[2.2.2]辛烷(DABCO)。
WO 00/34355要求保护基于金属乙酰丙酮化物的催化剂:例如,乙酰丙酮锌。此催化剂实际上能够降低包含异氰酸酯二聚体基团的聚氨酯粉末涂料组合物的固化温度,但其反应产物主要是脲基甲酸酯(M.Gedan-Smolka,F.Lehmann,D.Lehmann“New catalysts for the lowtemperature curing of uretdione powder coatings”International Waterborne,Highsolids and Powder Coatings Symposium,New Orleans,2001年2月21-23日)。脲基甲酸酯是一摩尔的醇与二摩尔的异氰酸酯的反应产物,然而在传统的聚氨酯化学中,一摩尔的醇与一摩尔的异氰酸酯的反应。因此,作为不理想的脲基甲酸酯的形成的结果,在技术上和经济上有价值的异氰酸酯基团被破坏了。
某些催化剂促进异氰酸酯二聚体基团以如下程度上再分裂,当使用包含异氰酸酯二聚体的固化剂时,粉末涂料或粘合剂组合物的固化温度可以明显降低。由于低的固化温度,具有降低的存贮稳定性。但是,过早反应导致降低的最终性能。
干燥混合物(干混物)的制备是已知的。但是,由于混合物的非均匀性,总是不能得到足够的最终性能的重现性(Pieter Gillis de Lange in“Powder Coatings Chemistry and Technology”Vincentz Network Hanover,2004,第168页,第214页)。这里要求显著提高该不足的重现性的方法。
发明内容
因此,本发明的目的是得到包含异氰酸酯二聚体基团的高反应性聚氨酯组合物,其在非常低的温度下已经能够固化,并且,显示出不寻常的存贮稳定性和更特别适于塑料和高光泽或无光的、光稳定的和气候稳定的粉末涂料和粘合剂的生产。同时,这些组合物应能够以可再现的方法制备。
令人惊讶地,上述复杂的需求组合已经通过本发明实现。
相应地,本发明提供了具有高于40℃的熔点的粉末状组合物,该组合物包含A)至少一种包含异氰酸酯二聚体基团的固化剂,B)至少一种季铵盐或鏻盐,C)至少一种环氧化物或乙酰丙酮化物形式的助催化剂,D)至少一种单体的、低聚的或聚合的一元或多元醇,任选地,E)至少一种单体的或聚合物形式的酸,和任选地,F)辅助剂和添加剂和/或额外的催化剂。
本发明的组合物具有高反应性并另外具有存贮稳定的优点。这意味着,本发明的组合物的NCO含量,在室温下存贮4周后,减少不超过25%。
优选地,固化剂A)基于芳族、脂族、脂(环)族和/或脂环族多异氰酸酯和含羟基化合物,所述固化剂具有小于5%重量的游离NCO含量和1%-25%重量的异氰酸酯二聚体基团含量(作为C2N2O2计算,分子量84)。
包含异氰酸酯二聚体基团的多异氰酸酯是公知的,并在例如US4,476,054,US 4,912,210,US 4,929,724和EP 0 417 603中描述。J.Prakt.Chem.336(1994)185-200提供了将异氰酸酯二聚化为异氰酸酯二聚体的工业相关方法的概括性综述。异氰酸酯至异氰酸酯二聚体的转化通常在可溶的二聚化催化剂,例如,二烷基氨基吡啶、三烷基膦、磷酰三胺或咪唑的存在下发生。此反应任选地在溶剂中进行,但是优选在不存在溶剂的情况下,当已经达到所需的转化率时,通过加入催化剂毒物来终止反应。其后通过短程蒸馏分离出过量单体异氰酸酯。如果催化剂是足够挥发性的,在单体分离过程中,反应混合物可以不含所述催化剂。在该情况下,不需加入催化剂毒物。原则上,宽范围的异氰酸酯适用于包含异氰酸酯二聚体基团的多异氰酸酯的制备。根据本发明优选使用异佛尔酮二异氰酸酯(IPDI)、六亚甲基二异氰酸酯(HDI)、2-甲基戊烷二异氰酸酯(MPDI)、二异氰酸根合二环己基甲烷(H12MDI)、2,2,4-三甲基六亚甲基二异氰酸酯/2,4,4-三甲基六亚甲基二异氰酸酯(TMDI)、降冰片烷二异氰酸酯(NBDI)、亚甲基二苯基二异氰酸酯(MDI)、甲苯胺二异氰酸酯(TDI)和四甲基亚二甲苯基二异氰酸酯(TMXDI)。非常特别优选的是IPDI和HDI。
这些具有异氰酸酯二聚体基团的多异氰酸酯到包含异氰酸酯二聚体基团的固化剂A)的转化,涉及游离的NCO基团与含羟基单体或聚合物(所述聚合物例如聚酯、聚硫醚、聚醚、聚己内酰胺、聚环氧化物、聚酯酰胺、聚氨酯)或低分子量的二元、三元和/或四元醇作为增链剂和,任选地,一元胺和/或一元醇作为链终止剂的反应,并且已经被广泛描述(EP 669 353,EP 669 354,DE 30 30 572,EP 639 598或EP 803 524)。优选的是聚酯和单体二元醇。除异氰酸酯二聚体基团,固化剂A)还可以包含异氰脲酸酯、缩二脲、脲基甲酸酯、氨基甲酸酯和/或脲结构。
所述固化剂的例子包括VESTAGON BF 9030、VESTAGON BF 1320和VESTAGON 1540(全部得自Evonik Degussa GmbH)和Crelan EF 403(Bayer AG)。特别优选的是VESTAGON BF 9030和VESTAGON BF 1320。
基于总的组合物,组分A)的份额特别地是5%-99%重量,优选是10%-80%重量和更优选是20%-50%重量。
作为组分B)提到的季铵盐或鏻盐用作催化剂。相应地,催化剂B)优选是具有卤素或有机或无机酸阴离子作为抗衡离子的四烷基铵盐或鏻盐。合适的催化剂的例子是甲酸四甲基铵、乙酸四甲基铵、丙酸四甲基铵、丁酸四甲基铵、苯甲酸四甲基铵、甲酸四乙基铵、乙酸四乙基铵、丙酸四乙基铵、丁酸四乙基铵、苯甲酸四乙基铵、甲酸四丙基铵、乙酸四丙基铵、丙酸四丙基铵、丁酸四丙基铵、苯甲酸四丙基铵、甲酸四丁基铵、乙酸四丁基铵、丙酸四丁基铵、丁酸四丁基铵和苯甲酸四丁基铵和乙酸四丁基鏻、甲酸四丁基鏻和乙酸乙基三苯基鏻、苯并三唑四丁基鏻(Tetrabutylphosphoniumbenzotriazolat)、苯酚四苯基鏻和癸酸三己基十四烷基鏻、氟化四甲基铵、氟化四乙基铵、氟化四丁基铵、氟化四辛基铵、氟化苄基三甲基铵、氢氧化四丁基鏻、氟化四丁基鏻、氯化四丁基铵、溴化四丁基铵、碘化四丁基铵、氯化四乙基铵、溴化四乙基铵、碘化四乙基铵、氯化四甲基铵、溴化四甲基铵、碘化四甲基铵、氯化苄基三甲基铵、氯化苄基三乙基铵、氯化苄基三丙基铵、氯化苄基三丁基铵、氯化甲基三丁基铵、氯化甲基三丙基铵、氯化甲基三乙基铵、氯化甲基三苯基铵、氯化苯基三甲基铵、溴化苄基三甲基铵、溴化苄基三乙基铵、溴化苄基三丙基铵、溴化苄基三丁基铵、溴化甲基三丁基铵、溴化甲基三丙基铵、溴化甲基三乙基铵、溴化甲基三苯基铵、溴化苯基三甲基铵、碘化苄基三甲基铵、碘化苄基三乙基铵、碘化苄基三丙基铵、碘化苄基三丁基铵、碘化甲基三丁基铵、碘化甲基三丙基铵、碘化甲基三乙基铵、碘化甲基三苯基铵和碘化苯基三甲基铵、氟化四甲基铵、氟化四乙基铵、氟化四丁基铵、氟化四辛基铵和氟化苄基三甲基铵。这些催化剂可以单独或以混合物形式添加。它们还可以被包封或经聚合地结合。所述催化剂还包含结晶水,当计算所用催化剂的量时,并不考虑此水;换而言之,将所述水的量减去。
在本发明的其它实施方案中,上述催化剂还可以施加于固体载体,例如二氧化硅(Kieselsure)。这带来提高的可研磨性并还带来更容易的加工性。为此目的,将所述催化剂溶解于合适的惰性溶剂中(例如,水),和加入相应量的合适的固体载体,所述量通常正好等于所述催化剂的量,所述载体的例子是Sipernat 2200(二氧化硅,来自EvonikDegussa GmbH)。其它沉淀磷酸钙或其它的煅制二氧化硅也是合适的。这些可以由Evonik Degussa GmbH在产品名SipernatTM或AEROSILTM下分别获得。在溶剂中混合后,去除后者。为此目的,适用于分离溶剂的所有技术装置都具有适合性,例子是干燥烘箱、蒸馏装置或者还有喷雾干燥器。所得产物可以以简单的方式处理。其不再具有粘连倾向,并且还可以显著更加容易地被研磨和筛分。
基于总的组合物,催化剂B)在本发明的组合物中的份额优选为0.1%重量-5%重量,优选为0.3%重量-3%重量。特别优选使用苯甲酸四乙基铵和氢氧化四丁基铵作为催化剂B)。
合适的C)的助催化剂为环氧化物或乙酰丙酮化物(Acetylacetonate)。环氧化物类的例子包括缩水甘油醚和缩水甘油酯、脂族环氧化物、基于双酚A的二环氧甘油醚和甲基丙烯酸缩水甘油酯。此过氧化物的例子是异氰脲酸三缩水甘油酯(TGIC,商品名Araldit 810,Huntsman)、对苯二甲酸二缩水甘油酯和偏苯三酸三缩水甘油酯(商品名Araldit PT 910和912,Huntsman)的混合物、叔碳酸缩水甘油酯(商品名Kardura E10,Shell)、3,4-环氧环己基甲基-3’,4’-环氧环己烷羧酸酯(ECC)、基于双酚A的二环氧甘油醚(商品名EPIKOTE 828,Shell)、乙基己基缩水甘油醚、丁基缩水甘油醚、季戊四醇四缩水甘油醚(商品名Polypox R 16,UPPC AG)和其它具有游离环氧基团的Polypox类型。而且,单-或多异氰酸酯和缩水甘油醇的反应产物也是合适的。
此外,合适的助催化剂包括金属乙酰丙酮化物,例子是乙酰丙酮锂或乙酰丙酮锌。
优选地,所述助催化剂是Araldit PT910和Araldit PT912。
当然,还可以使用上述助催化剂的混合物作为组分C)。
基于总的组合物,作为组分C)的所述助催化剂的份额更特别地为0.1%重量-5%重量,优选0.3%重量-3%重量。
本发明的一个变型包括上述催化剂B)或助催化剂C)的聚合地结合(polymere Anbindung)。例如,催化剂B)或助催化剂C)可以化学地结合(chemisch gebunden)到固化剂A)或醇D)上。为此目的,例如,所述助催化剂C)的环氧化物基团可以与羟基聚酯(D)的酸基团反应。或者,氢氧化四烷基铵B)可以与羟基聚酯D)的酸基团反应以形成盐。
另外,所述催化剂和助催化剂都可以以壳包裹并由此形成包封。
在“Microencapsulation and Particle Coating”Center for ProfessionalAdvancement(会议论文集),Amsterdam 2005提供了微型包封(microencapsulation)的例子。特别合适的壳材料包括聚合物,例子是聚酯、聚烯烃、聚丙烯酸酯、聚醚、聚氨酯、聚碳酸酯、聚乙烯基醚和其它在所述文献中论述的聚合物。
而且,作为必要组分D),本发明的组合物包含单体的、低聚的或聚合的一元或多元醇。在反应条件下,这些醇与所述固化剂的官能团(异氰酸酯二聚体)反应并由此导致交联。
特别合适的单体醇是具有至少32g/mol的分子量的一元、二元或多元醇。
所述一元醇包括例如,甲醇、乙醇、正丙醇、异丙醇、正丁醇、异丁醇、仲丁醇、异构的戊醇、己醇、辛醇和壬醇、正癸醇、正十二醇、正十四醇、正十六醇、正十八醇、环己醇、异构的甲基环己醇和羟甲基环己烷。
所述二元醇包括例如,乙二醇、三乙二醇、1,4-丁二醇、1,5-戊二醇、1,6-己二醇、3-甲基-1,5-戊二醇、新戊二醇、2,2,4(2,4,4)-三甲基己二醇和羟基新戊酸新戊二醇酯。
所述三元醇,例如,三羟甲基丙烷、二(三羟甲基)丙烷、三羟甲基乙烷、1,2,6-己三醇、1,2,4-丁三醇、三(β-羟乙基)异氰脲酸酯、季戊四醇、甘露醇或山梨醇。
在所述低聚的或聚合的醇的组中,优选使用具有5-500的OH数(OHZahl)(以mg KOH/克为单位)的聚酯、聚醚、聚丙烯酸酯、聚氨酯和/或聚碳酸酯。
更特别地,使用由羧酸及与优选地多元醇构造的聚酯作为组分D)。用于制备这些聚酯的优选羧酸可以在性质上是脂族的、脂环族的、芳族的和/或杂环族的和任选地可以是被卤原子取代的和/或不饱和的。其可以提及的例子包括:丁二酸、己二酸、辛二酸、十二烷二酸、十四烷二酸、壬二酸、癸二酸、邻苯二甲酸、对苯二甲酸、间苯二甲酸、偏苯三酸、均苯四酸(Pyromellitsure)、四氢邻苯二甲酸、六氢邻苯二甲酸、六氢对苯二甲酸、二-和四氯邻苯二甲酸、内亚甲基四氢邻苯二甲酸、戊二酸、马来酸和富马酸和-如可以-其酸酐、对苯二甲酸二甲酯、对苯二甲酸二乙二醇酯、以及环状单羧酸,例如,苯甲酸、对-叔丁基苯甲酸或六氢苯甲酸。
用于制备聚酯D)的合适的多元醇的例子包括乙二醇、1,2-和1,3-丙二醇、1,4-和2,3-丁二醇、二-β-羟乙基丁二醇、1,6-己二醇、1,8-辛二醇、新壬二醇、环己二醇、双(1,4-羟甲基)丙烷、2-甲基-1,3-丙二醇、2-甲基1,5-戊二醇、2,2,4(2,4,4)-三甲基-1,6-己二醇、甘油、三羟甲基丙烷、三羟甲基乙烷、1,2,6-己三醇、1,2,4-丁三醇、三(β-羟乙基)异氰脲酸酯、季戊四醇、甘露醇和山梨醇以及二乙二醇、三乙二醇、四乙二醇、二丙二醇、多丙二醇、多丁二醇、亚二甲苯基二甲醇(Xylylenglycol)和羟基新戊酸新戊二醇酯。
另外地,来自内酯的单酯和聚酯,例如,ε-己内酰胺,或羟基羧酸例如羟基新戊酸、ε-羟基癸酸、ε-羟基己酸、疏基乙酸,可以用作制备聚合物D)的起始材料。
此外,合适的聚酯是,上述多羧酸和/或其衍生物和多酚的聚酯,例如,氢醌、双酚A、4,4’-二羟基联苯或双(4-羟苯基)砜,或者碳酸的聚酯,其可由氢醌、二酚基丙烷、对亚二甲苯基二甲醇、乙二醇、丁二醇或己-1,6-二醇和其它多元醇通过例如与碳酰氯或碳酸二乙酯和/或二苯酯的典型的缩合反应获得,或由环状碳酸酯,例如,碳酸乙二酯或碳酸亚乙烯酯通过已知方法聚合获得。包含碳酸酯基团的示例性的聚合物D)可以如已知的通过示例性提到的具有62-300g/mol的分子量范围的二元或三元醇与碳酸二芳基酯反应而获得,所述碳酸二芳基酯例如,碳酸二苯基酯、碳酰氯或,优选地,环状碳酸酯,例如,亚丙基碳酸酯(Trimethylencarbonat)或2,2-二甲基亚丙基碳酸酯(Dimethyl-trimethylencarbonat)(NPC),或这些环状碳酸酯的混合物。特别优选的碳酸酯二醇是可以由所述二元醇作为起始分子和NPC发生开环反应制备的那些。
同样适合作为用于制备聚合物D)的起始材料是,硅酸(kieselsure)的聚酯、磷酸的聚酯,例如由甲烷-、乙烷-、β-氯乙烷-、苯-或苯乙烯-磷酸、-磷酰氯或-磷酸酯与上述种类的多元醇或多酚获得;硼酸的聚酯、聚硅氧烷,例如,通过二烷基二氯硅烷与水的水解和其后以多元醇的处理获得的产物,以及可通过聚硅氧烷二氢化物与烯烃例如烯丙醇或丙烯酸的加成反应获得的产物。
可以用作组分D)可能的聚酯的附加的例子是,如在例如DE-OS 24 10 513中所述的多羧酸与缩水甘油基化合物的反应产物。
可以使用的缩水甘油基化合物的例子是具有4-18个碳原子的2,3-环氧-1-丙醇与一元酸的酯,例子是棕榈酸缩水甘油酯、月桂酸缩水甘油酯和硬脂酸缩水甘油酯;具有4-18个碳原子的环氧烷,例如环氧丁烷,和缩水甘油醚,例如辛基缩水甘油醚。
上述聚酯可以以常规方法,如在例如Methoden der OrganischenChemie(Houben-Weyl);第14/2册,第1-5页,第21-23页,第40-44页,Georg Thieme Verlag,Stuttgart,1963,或者在C.R.Martens,Alkyd Resins,第51-59页,Reinhold Plastics Appl.Series,Reinhold Publishing Comp.,New York,1961中所述,在惰性气体气氛在100-270℃,优选130-230℃的温度下,在熔体中或在共沸过程中,通过缩合反应获得。
合适的聚合物D)还进一步包括羟基官能聚醚和聚碳酸酯。优选的聚醚可以例如通过环氧化物的加聚反应制备,所述环氧化物例如,环氧乙烷、环氧丙烷、环氧丁烷、氧杂环丁烷、3,3-双(氯甲基)氧杂双环丁烷、四氢呋喃、苯乙烯环氧化物或二酚基丙烷的双-2,5-环氧丙醚;在路易斯酸(例如,三氟化硼)存在下通过阳离子聚合;或通过与碱金属氢氧化物或碱金属醇盐的阴离子聚合反应;或通过这些环氧化物,任选地以混合物形式或相继地,与包含反应性氢原子的起始物组分的加成反应,所述起始物组分的例子是醇或胺,例如水、乙二醇、聚丙1,3-或1,2-二醇、戊二醇、己二醇、癸二醇、三羟甲基丙烷、甘油、苯胺、氨、乙醇胺、乙二胺、二(β-羟丙基)甲胺以及羟烷基化苯酚,例如二(β-羟基乙氧基)间苯二酚。
而且,还适合作为聚合物D)的是,例如,在聚氨酯化学领域已知的聚硫醚、聚缩醛、聚环氧化物、聚酯酰胺或聚氨酯,它们的分子量范围为250-8500g/mol并包含对于异氰酸酯基团具有反应性的羟基。
特别优选的是使用具有15-150的OH数和500-8000g/mol的平均分子量的含羟基聚酯作为组分D)。
当然,还可以使用上述单体、低聚物和/或聚合物的混合物。所述聚合物可以是非晶态的或部分结晶的。更特别地,基于总的组合物,所述D)的份额为1%重量-95%重量,优选2%重量-50%重量。
本发明的组合物可以进一步包含至少一种单体或聚合物形式的酸(组分E)。适用于本发明目的的酸包括具有布朗斯台德酸(Bronstedtsure)或路易斯酸性质的所有固体或液体的、有机或无机的、单体或聚合的物质。可以提及的例子包括:硫酸、乙酸、苯甲酸、丙二酸、对苯二甲酸、以及具有至少20的酸数的共聚酯或共聚酰胺。基于总的组合物,所述酸当存在时更特别地以0.1%-10%重量的份额存在。
本发明的组合物可以进一步包含在漆料或粘合剂技术中惯常的辅助剂和添加剂,和/或额外的催化剂作为组分F)。此辅助剂和添加剂的例子是流动控制剂(Verlaufsmittel),例如聚硅氧烷或丙烯酸酯,光稳定剂,例如空间位阻胺,或例如在EP 669 353中描述的其它的辅助剂。而且,作为辅助剂,其还可以是在总的组合物中以例如至多50%重量存在的填料和颜料,例如二氧化钛。基于总的组合物,所述辅助剂和添加剂当存在时的份额更特别地是0.001%-55%重量。
任选地,可以存在在聚氨酯化学中已知的额外的催化剂。这些主要是特别为0.001%-1%重量的量的有机金属催化剂,例如,二月桂酸二丁基锡、或还有叔胺,例如1,4-二氮杂双环[2.2.2]辛烷。
同样,本发明提供了用于制备本发明的粉末状组合物的方法,包括各组分A)-F)的干混或各组分A)-F)的均匀混合物的干混,前提条件是组分B)和C)不存在于同一种均匀混合物中。
因此本发明的方法是基于本发明的组合物的各组分的干混或各组分的混合物的干混。
在本发明的意义上,干混物(Trockenmuschung)是并非由所有组分的完全熔化或由所有组分的完全溶解导致的混合物。因此,此干混物还不是完全均匀的。所述干混的操作可以在任何本领域已知的并适于本目的的混合器中发生。所述的混合器更特别地包含所有类型的搅拌釜(例如,Ldige混合器)、振摇混合器(例如,管式)和其它能够在室温下混合该粉末状组合物的装置。
在最简单的情况下,将所述各组分干混,换而言之,无溶剂混合,以制备本发明的粉末状组合物。在本发明的方法的另一实施方案中,所述组合物的各组分的均匀混合物彼此干混。在此方法变型的情况下,组分B)和C)不得存在于同一种均匀混合物中,以避免不希望的预反应。
所述均匀混合物是指在溶剂中或在熔体中的混合物。
为制备所述部分混合物的目的的组分的均匀化可以在合适的装置中发生,例如可加热的搅拌釜、捏合机或还有挤出机,并且不应超过上限温度(120-130℃)。优选地,在一种均匀混合物中一起使用组分A)和D)。还优选在此A)和D)的混合物中加入组分C)。其后,将组分或部分混合物单独地或一起研磨并筛分。针对筛分的最大粒度为200μm,优选100μm。然后,所有研磨和筛分的组分在合适的混合装置(例如,管式)中仔细地彼此干燥混合。如果需要,此混合物可以在附加的步骤中在稍低于熔点的升高温度下再次烧结在一起(zusammengesintert),并然后又研磨和筛分至所需尺寸。
同样,本发明提供了包含本发明的组合物的粘合剂组合物,以及本发明的组合物用于制备金属、塑料、玻璃、木材、纺织品、纸或皮革的基材、纤维复合材料或其它耐热基底的粘合剂的用途。
同样,本发明提供了包含本发明的组合物的粉末涂料,以及本发明的组合物用于制备在金属、塑料、玻璃、木材或皮革基材或其它耐热基底的表面漆料的用途。
同样,本发明提供了包含本发明的组合物的金属涂料组合物,更特别地用于汽车车身、摩托车和自行车、建筑构件和家用器具、木材涂料组合物、玻璃涂料组合物、皮革涂料组合物和塑料涂料组合物。
在根据本发明的用途的情况下,本发明的组合物以合适的施加方式施加于基材,例如通过喷雾、流动床烧结或散布(Streuen)。准备好喷雾的粉末至合适的基材的施加可以根据已知的方法发生,例如,通过静电粉末喷雾、流动床烧结、或静电流动床烧结。在粘合的情况下,将粉末施加于将要被接合的基材,其然后被彼此压制。
在施加之后,通过加热至60-220℃的温度1至60分钟固化经涂覆的工件,优选地,在80-160℃的温度下加热6至30分钟。
即使没有进一步论述,认为本领域技术人员会能够在最宽范围的情况下利用上述说明书。因此,优选的实施方案和实施例将仅作为说明性内容理解,其无论如何不被理解为限制性公开。
使用以下实施例举例说明本发明。本发明的另外的实施方案可通过类推获得。
具体实施方式
实施例
根据DIN 53240-2测定OH数。
在此方法中,样品在存在4-二甲氨基吡啶作为催化剂的情况下与乙酸酐反应,羟基被乙酰化。这产生了每羟基一个分子的乙酸,而其后的过量乙酸酐的水解产生两个分子的乙酸。通过滴定法,由主值和平行进行的空白值之间的差异测定乙酸的消耗。
通过加入二丁胺和然后用盐酸靠溴酚蓝返滴定过量的二丁胺,湿化学测定NCO数。所使用的溶剂可以是异丙醇与水的混合物。
通过加入丁胺和然后用盐酸靠溴酚蓝返滴定过量的丁胺,湿化学测定异氰酸酯二聚体含量。所使用的溶剂可以是异丙醇与水的混合物。
组分 | 产品说明,生产商 |
VESTAGON EP BF9030 | 固化剂(A),异氰酸酯二聚体含量:11.5-13.0%,软化点:74-75℃,TG:40-50℃,Evonik Degussa GmbH,Coatings & Colorants |
TEAB | 催化剂,硼酸四乙基铵(B),Fluka |
DYNACOLL 7330 | (部分)结晶OH聚酯D),OH数31mg KOH/g,Schmp.:81℃,Evonik Degussa GmbH,Coatings& Colorants |
Sipernat 2200 | 沉积的二氧化硅,Evonik Degussa GmbH,Feststoffe und Pigmente |
ARALDIT PT 910 | 助催化剂C),包含环氧化物基团,Vantico, |
KRONOS 2160 | 二氧化钛,Kronos |
RESIFLOW PV 88 | 流动控制剂,Worlee |
Schmp.:熔点;TG:玻璃化转变温度
实施例1:
a)A)、C)和D)的均相混合物
61.65g的DYNACOLL 7330(组分D)在120℃下(恒温设定)加入钢罐中并在约1h内在搅拌下熔化。其后,在相同温度下,一次性加入35.35g的VESTAGON BF 9030(组分A)并持续搅拌约1.5-2h。其后,加入1g的Araldit PT 910(组分C)并再搅拌15min。当呈现均匀熔体时,可以卸出产物。将冷却的熔体在家用粉碎机(Braun,4142型)中进行初步破碎并然后研磨。在液氮的协助下,在快速转子磨(Fritsch,Pulverisette 14型)上进行研磨操作。N2冷却防止产物在研磨机中粘连。已经变得湿润的产物其后必须在室温下在真空干燥箱(50mbar)中干燥。一旦所述产物变干(由自由流动性视觉评价),将其应用于分析筛分机(Analysen-Siebmaschine)(Retsch,AS200 Basic型)并筛分至<63μm的粒度。
b)TEAB和Sipernat 2200的混合物的制备
在500ml圆底烧瓶中预先加入50g TEAB(组分B)与150ml的去离子水,并且在5分钟内在室温下溶解。其后,加入50g的Sipernat2200(载体),并在旋转蒸发仪中在50℃和约6mbar下浓缩。将尽可能干燥的产物在混合机中粉碎,然后在50℃(50mbar)下在真空干燥箱中干燥至质量恒定。然后将其研磨并筛分至<63μm。
c)本发明的组合物的制备
称量98g的均匀化的和粉碎的A)、C)和D)的混合物(实施例1a)与来自步骤b)的2g混合物一起加入1L Turbula塑料容器并在振摇混合器(Bachhofen AG,Turbula型,Schatz体系)中以46转/分混合30分钟。其后,所述混合物分布于干燥金属板上并在80℃下部分烧结约15-20分钟。然后,再次研磨并筛分至100-200μm的粒度。这提供了具有约90℃的熔点和4.40%的NCO含量(理论值:4.37%)的粉末。此NCO数在室温下即使在4星期后仍保持基本不变(4.20%),这证明了本发明的混合物的存贮稳定性。
d)对比实验
61.65g的DYNACOLL 7330在120℃下预先加入钢罐(恒温设定)中并在约1小时内在搅拌下熔化。其后,在相同温度下,加入35.35g的VESTAGON BF 9030、1g的PT910和2g的TEAB和Sipernat的混合物。
d1)在此温度下在15分钟内,所述混合物发生凝胶化。
d2)如果在加入最后的组分后,温度在10min内降低至室温,在研磨和筛分至100-200μm后,得到具有2.60%(理论值:4.37%)的NCO含量的粉末。在室温下,在4个星期后,NCO数下降至1.90%,并且所述粉末不再能被完全溶解。
实施例2:粘合纺织品的一般步骤
从棉织物切下两个尺寸为110mm X 110mm的布片。在一块棉布片的底面上,将所述粉末状组合物,借助于具有小于160μm的网眼尺寸的筛网,施加到待粘合的100mm X 50mm的区域。使用重量是约30g/m2。在热空气烘箱中,在高于所述粉末的熔点之上10℃的温度,在织物表面烧结所述粉末5分钟。
在冷却后在140℃的温度下,用粘合剂预涂覆的棉布片与未涂覆的布片在压制机中在10bar压力下被层压10分钟。
一天后,从织物复合物切下15mm宽和110mm长的测试条,粘合长度为50mm。去掉两个外部的条。
为测量剥离强度,根据DIN EN 28510将未粘合的织物条的端部固定于拉伸试验机的顶部和底部夹持装置,并且在180°的角度以50mm/分钟被分离。
所报告的数值是作为5次测量的平均值的以N为单位的最大力Fmax。高于4N的力Fmax,认为该粘合是好的。
实施例3:实施例1c)与实施例1 d2)的纺织品粘合
根据本发明的组合物1c)的纺织品粘合得到良好的粘合,具有6.9N的Fmax值。非发明组合物1d2)不再被熔化并因此不能用于粘合。
Claims (14)
1.具有高于40℃的熔点的粉末状组合物,该组合物包含A)至少一种包含异氰酸酯二聚体基团的固化剂,B)至少一种季铵盐或鏻盐,C)至少一种环氧化物或乙酰丙酮化物形式的助催化剂,D)至少一种单体的、低聚的或聚合的一元或多元醇,任选地,E)至少一种单体的或聚合物形式的酸,和任选地,F)辅助剂和添加剂和/或额外的催化剂。
2.根据权利要求1的组合物,其特征在于,所述固化剂A)基于芳族、脂族、脂(环)族和/或脂环族的多异氰酸酯和含羟基的化合物,所述固化剂具有小于5%重量的游离NCO含量和1%-25%重量的异氰酸酯二聚体基团含量。
3.根据权利要求1或2的组合物,其特征在于,基于总的组合物,A)的份额是5-99%重量。
4.根据权利要求1-3的一项或多项的组合物,其特征在于,B)涉及具有卤素或有机或无机酸阴离子作为抗衡离子的四烷基铵盐或鏻盐。
5.根据权利要求1-4的一项或多项的组合物,其特征在于,基于总的组合物,B)的份额是0.1-5%重量。
6.根据权利要求1-5的一项或多项的组合物,其特征在于,使用苯甲酸四乙基铵和氢氧化四丁基铵作为B)。
7根据权利要求1-6的一项或多项的组合物,其特征在于,基于总的组合物,C)的份额是0.1-5%重量。
8.根据权利要求1-7的一项或多项的组合物,其特征在于,使用聚酯作为组分D)。
9.根据权利要求1-8的一项或多项的组合物,其特征在于,使用具有15-150的OH数和500-8000g/mol的平均分子量的含羟基聚酯作为组分D)。
10.根据权利要求1-9的一项或多项的组合物,其特征在于,基于总的组合物,组分D)的份额是1-95%重量。
11.根据权利要求1-10的一项或多项的组合物,其特征在于,使用流动控制剂、光稳定剂、填料和颜料作为组分F)。
12.用于制备根据权利要求1-11的一项或多项的粉末状组合物的方法,包括:干混各组分A)-F),或干混各组分A)-F)的均匀混合物,前提条件是组分B)和C)不存在于同一种均匀混合物中。
13.包含根据权利要求1-11的一项或多项的粉末状组合物的粘合剂组合物、粉末涂料、金属涂料组合物、木材涂料组合物、玻璃涂料组合物、皮革涂料组合物和塑料涂料组合物。
14.根据权利要求1-11的一项或多项的粉末状组合物用于产生金属、塑料、玻璃、木材、纺织品、纸或皮革基材或纤维复合材料的粘合的用途。
15.根据权利要求1-11的一项或多项的粉末状组合物用于在金属、塑料、玻璃、木材或皮革基材上产生漆料涂层的用途。
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DE102004011004A1 (de) * | 2004-03-06 | 2005-09-22 | Degussa Ag | Verfahren zur Herstellung fester, hochreaktiver Uretdiongruppen haltiger Polyurethanzusammensetzungen |
DE102004017005A1 (de) | 2004-04-02 | 2005-10-20 | Bayer Materialscience Ag | Abspalterfreier Polyurethan-Pulverlack mit niedriger Einbrenntemperatur |
DE102004020451A1 (de) * | 2004-04-27 | 2005-12-01 | Degussa Ag | Uretdiongruppenhaltige Polyurethanzusammensetzungen, welche bei niedriger Temperatur härtbar sind und (teil-)kristalline Harze enthalten |
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DE102004048775A1 (de) * | 2004-10-07 | 2006-04-13 | Degussa Ag | Hoch reaktive uretdiongruppenhaltige Polyurethanzusammensetzungen |
DE102004062588A1 (de) | 2004-12-24 | 2006-07-06 | Degussa Ag | Hochreaktive uretdiongruppenhaltige Polyurethanzusammensetzungen auf Basis von 1,4-Diisocyanatocyclohexylmethan |
DE102005013329A1 (de) | 2005-03-23 | 2006-11-16 | Degussa Ag | Niedrigviskose uretdiongruppenhaltige Polyadditionsverbindungen, Verfahren zur Herstellung und Verwendung |
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DE102006042494A1 (de) * | 2006-09-07 | 2008-03-27 | Evonik Degussa Gmbh | Bei niedriger Temperatur härtbare, uretdiongruppenhaltige Polyurethanzusammensetzungen mit quartären Ammoniumhalogeniden |
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US20080265201A1 (en) | 2007-04-26 | 2008-10-30 | Degussa Gmbh | Low-temperature-curable polyurethane compositions with uretdione groups, containing polymers based on polyols that carry secondary oh groups |
WO2008138855A1 (de) * | 2007-05-11 | 2008-11-20 | Evonik Degussa Gmbh | Bei niedriger temperatur härtbare, uretdiongruppen aufweisende polyurethanzusammensetzungen enthaltend polymere auf der basis von sekundären oh-gruppen tragenden polyolen |
DE102007062316A1 (de) | 2007-12-21 | 2009-06-25 | Evonik Degussa Gmbh | Reaktive Isocyanatzusammensetzungen |
-
2008
- 2008-02-01 DE DE102008007386A patent/DE102008007386A1/de not_active Withdrawn
- 2008-11-19 JP JP2010544601A patent/JP6108652B2/ja not_active Expired - Fee Related
- 2008-11-19 US US12/809,911 patent/US8702899B2/en not_active Expired - Fee Related
- 2008-11-19 KR KR1020107017113A patent/KR20100115750A/ko not_active Application Discontinuation
- 2008-11-19 WO PCT/EP2008/065823 patent/WO2009095117A1/de active Application Filing
- 2008-11-19 CA CA2713399A patent/CA2713399A1/en not_active Abandoned
- 2008-11-19 EP EP08872017A patent/EP2238193A1/de not_active Ceased
-
2009
- 2009-01-23 TW TW98103014A patent/TWI469999B/zh not_active IP Right Cessation
- 2009-01-24 CN CN200910009944.4A patent/CN101497686B/zh not_active Expired - Fee Related
Cited By (8)
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CN102702461A (zh) * | 2012-05-24 | 2012-10-03 | 黑龙江大学 | 一种具有电致变色性能的聚氨酯及其制备方法 |
CN102702461B (zh) * | 2012-05-24 | 2013-12-25 | 黑龙江大学 | 一种具有电致变色性能的聚氨酯及其制备方法 |
CN107011774A (zh) * | 2017-04-10 | 2017-08-04 | 立邦涂料(天津)有限公司 | 一种高硬度粉末涂料组合物及其制备方法和用途 |
CN107236444A (zh) * | 2017-06-05 | 2017-10-10 | 靖江励创信息科技有限公司 | 一种疏水阻燃聚氨酯粉末涂料的制备方法 |
CN108608604A (zh) * | 2018-05-22 | 2018-10-02 | 郑州大学 | 一种塑料废弃物的分离方法 |
CN108608604B (zh) * | 2018-05-22 | 2020-06-16 | 郑州大学 | 一种塑料废弃物的分离方法 |
CN110305294A (zh) * | 2019-07-15 | 2019-10-08 | 万华化学集团股份有限公司 | 一种存储稳定的含有脲二酮基团的多异氰酸酯的制备方法 |
CN110305294B (zh) * | 2019-07-15 | 2021-04-20 | 万华化学集团股份有限公司 | 一种存储稳定的含有脲二酮基团的多异氰酸酯的制备方法 |
Also Published As
Publication number | Publication date |
---|---|
JP2011511109A (ja) | 2011-04-07 |
US8702899B2 (en) | 2014-04-22 |
JP6108652B2 (ja) | 2017-04-05 |
DE102008007386A1 (de) | 2009-08-06 |
US20100263792A1 (en) | 2010-10-21 |
CN101497686B (zh) | 2014-10-22 |
TWI469999B (zh) | 2015-01-21 |
CA2713399A1 (en) | 2009-08-06 |
TW200948841A (en) | 2009-12-01 |
WO2009095117A1 (de) | 2009-08-06 |
EP2238193A1 (de) | 2010-10-13 |
KR20100115750A (ko) | 2010-10-28 |
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