CN113631615A - 生产聚氨酯-聚异氰脲酸酯弹性体、密封材料以及具有长适用期的粘合剂的方法 - Google Patents
生产聚氨酯-聚异氰脲酸酯弹性体、密封材料以及具有长适用期的粘合剂的方法 Download PDFInfo
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- CN113631615A CN113631615A CN202080024634.4A CN202080024634A CN113631615A CN 113631615 A CN113631615 A CN 113631615A CN 202080024634 A CN202080024634 A CN 202080024634A CN 113631615 A CN113631615 A CN 113631615A
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- isocyanate
- catalyst
- process according
- alkaline earth
- earth metal
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Abstract
本发明涉及一种制备聚氨酯弹性体的方法,包含以下步骤:(A)通过混合(a1)至少一种包含选自聚酯多元醇、聚醚多元醇或其混合物的多元醇的异氰酸酯反应性组合物和(a2)至少一种多异氰酸酯并使混合物反应形成异氰酸酯预聚物(a)来制备异氰酸酯预聚物(a),所述多元醇平均官能度在≥1.8至≤2.5的范围内和OH值在≥20mg KOH/g至≤450mg KOH/g的范围内,其中异氰酸酯预聚物的异氰酸酯含量在≥1重量%至≤9重量%的范围内,和(B)在至少一种催化剂(c)存在下通过将至少一种环氧化物(b)与异氰酸酯预聚物(a)混合来制备反应混合物,并将混合物加热至至少80℃以获得聚氨酯弹性体,其中催化剂(c)为通过将碱金属或碱土金属盐引入化合物R‑NH‑CO‑OR’而获得的混合物,其中碱金属或碱土金属盐的量为0.00001至0.1mol每kg异氰酸酯预聚物(a)、环氧化物(b)和催化剂(c)的总重量。此外,本发明涉及通过根据本发明的方法获得的聚氨酯弹性体以及这种聚氨酯弹性体作为辊的一部分或作为密封料的用途。
Description
本发明涉及一种制备聚氨酯弹性体的方法,包含以下步骤:(A)通过混合(a1)至少一种包含选自聚酯多元醇、聚醚多元醇或其混合物的多元醇的异氰酸酯反应性组合物和(a2)至少一种多异氰酸酯,并使混合物反应形成异氰酸酯预聚物(a)来制备异氰酸酯预聚物(a),所述多元醇的平均官能度在≥1.8至≤2.5的范围内和OH值在≥20mg KOH/g至≤450mg KOH/g的范围内,其中异氰酸酯预聚物的异氰酸酯含量在≥1重量%至≤9重量%的范围内,和(B)在至少一种催化剂(c)存在下通过将至少一种环氧化物(b)与异氰酸酯预聚物(a)混合来制备反应混合物,并将混合物加热至至少80℃以获得聚氨酯弹性体,其中催化剂(c)为通过将碱金属或碱土金属盐引入化合物R-NH-CO-OR’而获得的混合物,其中R和R'可以相同或不同并且可以为有机化学里任何已知的基团,其中碱金属或碱土金属盐的量为0.00001至0.1mol每kg异氰酸酯预聚物(a)、环氧化物(b)和催化剂(c)的总重量。此外,本发明涉及通过本发明的方法获得的聚氨酯弹性体以及这种聚氨酯弹性体作为辊的一部分或作为密封料的用途。
特别是大表面积塑料部件(例如用于高负载应用的轮子和辊)的生产需要具有长的开放陈化时间(open assembly time)的塑料系统(plastics system)。因此,例如可在塑料系统固化之前填充模具来提供成品塑料。然而,塑料系统也被要求尽可能快地固化以提供塑料,从而使更快的脱模时间成为可能,因而提高盈利能力。此外要求特别是承受高负载的模塑制品为高机械强度以及特别是压缩变形。所需的开放陈化时间通常通过缓慢反应的扩链剂、剧烈还原催化作用或通过设置大气湿度来实现。然而,这样做的结果是,首先无法控制脱模时间,其次需要很长的固化时间。
US20110065885中记载了用于生产聚异氰脲酸酯-聚氨酯弹性体的一种方法。其中,使用基于乙酸钾的催化剂系统,开放陈化时间在此在10分钟的范围内。
专利文件EP0643086记载了聚氨酯预聚物在1,8-二氮杂二环十一碳烯(DBU)的2-乙基己酸盐作为催化剂系统的存在下的反应。材料的固化在此作为单组分系统实现以及可从50℃热引发。尽管如此,开放时间仍有待延长。
WO10121898记载了聚异氰酸酯组分,其部分地由脲预聚物(-NH-CO-NH-)朝向阴离子的双配位基组成,所述双配位基与氯化锂混合。当该组分与二缩水甘油醚和含有多元醇的第二组分混合,该混合物被加热至80至90℃时,会发生快速反应,导致材料的完全固化。然而,在WO10121898中没有提及具有低的压缩变形的弹性体。
WO2015/078740涉及大型纤维增强聚氨酯部件的生产。为了提供具有长的开放时间和快的固化时间的这种部件的生产方法,WO2015/078740提出了聚氨酯催化剂混合物的应用,所述聚氨酯催化剂混合物可通过将碱金属或碱土金属盐引入含氨基甲酸酯基团的化合物中而获得。
WO2015078740没有阐明弹性体的生产。
本发明的目的是提供一种生产聚氨酯弹性体的方法,其中用于生产聚氨酯弹性体的反应混合物显现长的开放时间,也允许较大部件的模具填充和快速固化。此外,本发明的目的是提供可通过这种方法获得的聚氨酯弹性体,其中所述弹性体包含低的压缩变形。
本发明的目的通过一种制备聚氨酯弹性体的方法实现,包含以下步骤:(A)通过混合(a1)至少一种包含选自聚酯多元醇、聚醚多元醇或其混合物的多元醇的异氰酸酯反应性组合物和(a2)至少一种多异氰酸酯,并使混合物反应形成异氰酸酯预聚物(a)来制备异氰酸酯预聚物(a),所述多元醇的平均官能度在≥1.8至≤2.5的范围内和OH值在≥20mg KOH/g至≤450mg KOH/g的范围内,其中异氰酸酯预聚物的异氰酸酯含量在≥1重量%至≤9重量%的范围内,和(B)在至少一种催化剂(c)存在下通过将至少一种环氧化物(b)与异氰酸酯预聚物(a)混合来制备反应混合物,并将混合物加热至至少80℃以获得聚氨酯弹性体,其中催化剂(c)为可通过将碱金属或碱土金属盐引入化合物R-NH-CO-OR’而获得的混合物,其中碱金属或碱土金属盐的量为0.00001至0.1mol每kg异氰酸酯预聚物(a)、环氧化物(b)和催化剂(c)的总重量。
本发明的弹性体根据DIN53504的断裂伸长率为至少80%,优选至少150%,更优选至少200%,特别是至少300%,和邵氏硬度最高达90邵氏A(shore A),优选最高达85邵氏A,更优选最高达75邵氏A,最优选最高达70邵氏A,同时邵氏硬度A优选大于20,更优选大于30,最优选大于40邵氏A。此外,本发明的弹性体的压缩变形优选不超过40%,更优选不超过25%,最优选不超过15%。
为了生产步骤(A)中的异氰酸酯预聚物(a),混合至少一种包含选自聚酯多元醇、聚醚多元醇或其混合物的多元醇的异氰酸酯反应性组合物(a1)和(a2)至少一种多异氰酸酯,所述多元醇的平均官能度在≥1.8至≤2.5的范围内和OH值在≥20mg KOH/g至≤450mgKOH/g的范围内。然后使混合物反应形成异氰酸酯预聚物(a)。该反应可通过众所周知的方式进行。例如,这些聚异氰酸酯预聚物可通过使过量的异氰酸酯(a2)在例如30℃至100℃的温度下(优选约80℃)与异氰酸酯反应组分(a2)反应以得到预聚物而获得。选择异氰酸酯(a2)和异氰酸酯反应组分(a1)的量以使成品预聚物的异氰酸酯含量在≥1重量%至≤9重量%的范围内,优选超过2重量%至低于8重量%,最优选超过4重量%至低于6重量%。
作为包含选自聚酯多元醇、聚醚多元醇及其混合物的多元醇的异氰酸酯反应性组合物,可以应用聚氨酯化学领域中已知的聚酯多元醇和/或聚醚多元醇,其平均官能度在≥1.8至≤2.5的范围内,优选1.9至2.3,更优选1.95至2.1,特别优选2.0,和OH值在≥20mgKOH/g至≤450mg KOH/g的范围内,优选25至200mg KOH/g,更优选30至120mg KOH/g,特别优选35至70mg KOH/g。
作为聚醚醇,其平均官能度在≥1.8至≤2.5的范围内,优选1.9至2.3,更优选1.95至2.1,特别优选2.0,和OH值在≥20mg KOH/g至≤450mg KOH/g的范围内,优选25至200mgKOH/g,更优选30至120mg KOH/g,特别优选35至70mg KOH/g,可以使用具有这些参数的常规聚醚多元醇。在此上下文中,本发明根据DIN53240确定OH值,并且所应用的多元醇的官能度应理解为理论官能度。对于聚醚多元醇,例如可通过基于起始分子的官能度来计算官能度从而获得理论官能度。当确定官能度时,不考虑聚醚多元醇制备过程中的副反应(例如歧化反应)的影响。
例如OH、SH和NH基团可以作为异氰酸酯反应性基团。作为异氰酸酯反应性基团,多元醇优选基本上具有OH基团,更优选只有OH基团。此处的平均OH值和平均官能度的计算基于所有使用的多元醇计。
聚醚多元醇在催化剂存在下通过已知方法而获得,例如通过至少加入一种起始分子的烷氧化物的阴离子聚合,所述起始分子包含1至4个,优选2至3个,更优选2个结合形式的反应性氢原子。使用的催化剂可以为碱金属氢氧化物,例如氢氧化钠或氢氧化钾;或碱金属醇盐,例如甲醇钠、乙醇钠或乙醇钾或异丙醇钾;或在阳离子聚合的情况下的路易斯酸,例如五氯化锑、三氟化硼乙醚化物或漂白土。还可使用双金属氰化物(被称为DMC催化剂)作为催化剂。
作为烷氧化物,优选使用一种或更多种在亚烷基中具有2至4个碳原子的化合物,例如四氢呋喃、1,2-环氧丙烷或1,2-和/或2,3-环氧丁烷,在每种情况下单独或以混合物的形式,优选1,2-环氧丙烷、1,2-环氧丁烷和/或2,3-环氧丁烷,特别是1,2-环氧丙烷。在一个优选的实施方案中,聚醚多元醇包含至少70重量%的环氧丙烷,更优选至少80重量%,特别是至少90重量%的环氧丙烷,基于烷氧化物的总重量计。
考虑的起始分子包括例如乙二醇、丙二醇、二甘醇、二丙二醇、丙三醇、三羟甲基丙烷、季戊四醇、甲胺、乙胺、异丙胺、丁胺、苄胺、苯胺、甲苯胺、甲苯二胺、萘胺、乙二胺、二乙醇胺、三乙醇胺,和其他,特别是二元醇。
在另一个优选的实施方案中,聚醚多元醇包含聚四亚乙基醚二醇(PTMEG),也称为聚四氢呋喃(PTHF)。如果PTHF作为聚醚多元醇存在,则异氰酸酯反应成分(a1)中PTHF的量为优选至少50%,更优选至少80%,最优选至少90%,基于异氰酸酯反应组分(a1)的总重量计。
作为平均官能度在≥1.8至≤2.5的范围内,优选1.9至2.3,更优选1.95至2.1,特别优选2.0,和OH值在≥20mg KOH/g至≤150mg KOH/g的范围内,优选25至200mg KOH/g,更优选30至120mg KOH/g,特别优选35至70mg KOH/g的聚酯多元醇,可使用具有这些参数的常规聚酯多元醇。
所用的聚酯醇通常通过多官能醇缩合而制备,优选具有1至12个碳原子的多官能醇,例如乙二醇、二甘醇、丁二醇、三羟甲基丙烷、丙三醇或季戊四醇;和具有2至12个碳原子的多官能羧酸,例如琥珀酸、戊二酸、己二酸、辛二酸、壬二酸、癸二酸、癸烷二羧酸、马来酸、富马酸、邻苯二甲酸、间苯二甲酸、对苯二甲酸和萘二甲酸的异构体,或其酸酐。除了具有1至12个碳原子的多官能醇之外,还可使用优选二官能起始分子的烷氧化产物。这种烷氧化产物优选OH值小于610mg KOH/g,并且优选大于100mg KOH/g,更优选大于200mg KOH/g,最优选大于400mg KOH/g。在本发明的一个优选的实施方案中,聚酯多元醇通过己二酸和丁二醇的酯化而获得。在一个更优选的实施方案中,聚酯包含至少70%重量,更优选至少80%重量,最优选至少90%重量的己二酸和丁二醇,基于用于制备本发明的聚酯的二元酸和二元醇计。
可使用疏水性物质作为制备聚酯的其他原料。疏水物质是水不溶性物质,其包含非极性有机基团并且还具有至少一个选自羟基、羧酸、羧酸酯或其混合物的反应性基团。疏水材料的当量重量优选为130至1000g/mol。例如可使用脂肪酸(例如硬脂酸、油酸、棕榈酸、月桂酸或亚油酸)以及脂肪和油(例如蓖麻油、玉米油、向日葵油、大豆油、椰子油、橄榄油或妥尔油)。在聚酯包含疏水性物质时,疏水性物质在聚酯醇的总的单体含量中的比例优选1至30mol%,更优选4至15mol%。
另一类优选使用的脂肪酸衍生的多元醇可以通过环氧化脂肪酸酯的开环,同时与醇反应,并任选地随后进行进一步的酯交换反应而获得。将羟基引入油和脂肪中主要是通过这些产物中存在的烯烃双键的环氧化,然后使生成的环氧基与一元或多元醇反应来实现的。这由环氧化物环产生了羟基,或在多官能醇的情况下产生具有较高数量的OH基团的结构。因为油和脂肪通常是甘油酯,在上述反应过程中还进行了平行的酯交换反应。由此获得的化合物优选分子量在500至1500g/mol的范围内。此类产品例如可从BASF以商品名获得。
在一个优选的实施方案中,除了异氰酸酯反应组分(a1)之外,使用小于30重量%,更优选小于10重量%,最优选不使用另外的具有异氰酸酯反应性基团的化合物来制备异氰酸酯预聚物(a)。
可使用已知的用于制备聚氨酯的所有脂族、脂环族和芳族异氰酸酯作为多异氰酸酯(a2)。它们优选平均官能度小于2.5。实例是2,2'-、2,4'-和4,4'-二苯甲烷二异氰酸酯、二苯甲烷二异氰酸酯单体和二苯甲烷二异氰酸酯的高级多环同系物(higher polycyclichomologs)(聚合MDI)的混合物、异佛尔酮二异氰酸酯(IPDI)或其低聚物、2,4-或2,6-甲苯二异氰酸酯(TDI)或其混合物、四亚甲基二异氰酸酯或其低聚物、六亚甲基二异氰酸酯(HDI)或其低聚物、萘二异氰酸酯(NDI)或其混合物。作为多异氰酸酯(a2),优选单体芳族二异氰酸酯,优选2,4-和2.6-TDI,或特别优选二苯甲烷二异氰酸酯单体,例如2,2'-二苯甲烷二异氰酸酯、2,4'-二苯甲烷二异氰酸酯、4,4'-二苯甲烷二异氰酸酯或其混合物。此处,二苯甲烷二异氰酸酯也可以与其衍生物混合使用。在那种情况下,二苯甲烷二异氰酸酯可特别优选包含最高达10重量%,还特别优选最高达5重量%的碳二亚胺、脲二酮或脲酮亚胺改性的二苯甲烷二异氰酸酯,特别是碳二亚胺改性的二苯甲烷二异氰酸酯。
在步骤(B)中,异氰酸酯(a)和至少一种环氧化物(b)在至少一种催化剂(c)存在下混合。对混合步骤而言,顺序不重要。在一个实施方案中,环氧化物(b)在异氰酸酯预聚物(a)的形成过程中已经存在。在一个优选的实施方案中,先生产异氰酸酯预聚物,然后加入环氧化物。此外,在一个优选的实施方案中,在形成异氰酸酯预聚物(a)时不存在催化剂(c)。
在一个优选的实施方案中,待在步骤(B)中使用的异氰酸酯预聚物(a)包含小于1重量%,更优选小于0.5重量%,最优选小于0.1%重量的单体二异氰酸酯,基于异氰酸酯(a)的总重量计。这可通过例如蒸馏(例如薄膜蒸馏)除去过量的未反应异氰酸酯来确保。
作为环氧化物(b)包含一个或更多个环氧基团的任何化合物,可使用通常用于制备环氧树脂的所有含有环氧化物的化合物。包含环氧基团的环氧化物(b)优选在25℃下为液体。这里也可使用这种化合物的混合物,其同样优选在25℃下是液体。
可用于本发明上下文的这种包含环氧基团的化合物的实例是
I)聚缩水甘油酯和聚(β-甲基缩水甘油基)酯,可通过使在分子中具有至少两个羧基的化合物在每种情况下与表氯醇和β-甲基表氯醇反应而获得。该反应在碱的存在下催化是有利的。
例如,脂族多元羧酸可用作具有至少两个羧基的化合物。这种脂族多元羧酸的例子是草酸、琥珀酸、戊二酸、己二酸、庚二酸、辛二酸、壬二酸和二聚或三聚的亚油酸。此外,也可使用环状脂族酸,例如四氢邻苯二甲酸、4-甲基四氢邻苯二甲酸、六氢邻苯二甲酸或4-甲基六氢邻苯二甲酸。也可使用芳族羧酸,例如邻苯二甲酸、间苯二甲酸或对苯二甲酸,以及这些羧酸任何所需的混合物。
II)聚缩水甘油基醚或聚(β-甲基缩水甘油基)醚,可通过具有至少两个醇羟基和/或酚羟基的化合物与表氯醇或β-甲基表氯醇在碱性条件下或酸性催化剂的存在下反应,然后用碱处理而获得。
这种类型的缩水甘油醚衍生自例如直链醇(例如乙二醇、二甘醇)或更高级的聚(氧化乙烯)二醇、1,2-丙二醇或聚(氧化丙烯)二醇、1,3-丙二醇、1,4-丁二醇、聚(氧四亚甲基)二醇、1,5-戊二醇、1,6-戊二醇、2,4,6-己三醇、丙三醇、1,1,1-三羟甲基丙烷、季戊四醇或山梨糖醇,以及聚表氯醇。
这种类型的其他缩水甘油醚可从脂环族醇获得,例如1,4-环己烷二甲醇、二(4-羟基环己基)甲烷或2,2-二(4-羟基环己基)丙烷;或从带有芳族基团和/或其他官能团的醇获得,例如N,N-二(2-羟乙基)苯胺或p,p'-二(2-羟乙基氨基)二苯基甲烷。
缩水甘油醚也可基于单环酚类,例如对叔丁基苯酚、间苯二酚或氢醌;或基于多环酚类,例如二(4-羟基苯基)甲烷、4,4'-二羟基联苯、二(4-羟基苯基)砜、1,1,2,2-四(4-羟基苯基)乙烷、2,2-二(4-羟基苯基)丙烷或2,2-二(3,5-二溴-4-羟基苯基)丙烷。
其他包含羟基并适用于制备缩水甘油醚的化合物是酚醛清漆,可通过将醛(如甲醛、乙醛、氯醛或糠醛)与酚类或二酚类缩合而获得,所述酚类或二酚类可以是未被取代的或被氯原子或C1至C9烷基取代的,例如苯酚、4-氯苯酚、2-甲基苯酚或4-叔丁基苯酚。
III)聚(N-缩水甘油基)化合物,可通过表氯醇与包含至少两个胺键合的氢原子的胺的反应产物的脱氯化氢反应而获得。这种胺为例如苯胺、正丁胺、二(4-氨基苯基)甲烷、间苯二甲胺或二(4-甲基氨基苯基)甲烷。聚(N-缩水甘油基)化合物还包括异氰脲酸三缩水甘油酯、环亚烷基脲的N,N'-二缩水甘油基衍生物,如亚乙基脲或1,3-亚丙基脲;和乙内酰脲的二缩水甘油基衍生物,如5,5-二甲基乙内酰脲。
IV)聚(S-缩水甘油基)化合物,例如可从二硫醇获得的二-S-缩水甘油基衍生物,所述二硫醇例如为1,2-乙烷二硫醇或二(4-巯基甲基苯基)醚。
V)脂环族环氧树脂,例如二(2,3-环氧环戊基)醚、2,3-环氧环戊基缩水甘油醚、1,2-二(2,3-环氧环戊氧基)乙烷或3',4'-环氧环己烷甲酸3,4-环氧环己基甲酯。
VI)单官能环氧树脂,如2-乙基己基缩水甘油醚、异丙基缩水甘油醚、丁基缩水甘油醚或甲苯缩水甘油醚。
在本发明的上下文中,可同样使用环氧树脂,其中1,2-环氧基与不同的杂原子或官能团键合。这些化合物包括4-氨基苯酚的N,N,O-三缩水甘油基衍生物、水杨酸的缩水甘油醚缩水甘油酯、N-缩水甘油基-N'-(2-缩水甘油基氧基丙基)-5,5-二甲基乙内酰脲和2-缩水甘油基氧基-1,3-二(5,5-二甲基-1-缩水甘油基乙内酰脲-3-基)丙烷。
特别优选的环氧化物(b)为(I)类和(II)类化合物,更具体而言为(II)类化合物。
环氧化物(b)的量优选0.3至15重量%,更优选0.5至10重量%,更具体而言0.8至5重量%,基于异氰酸酯预聚物(a)和环氧化物(b)的总重量计。
催化剂(c)为可通过将碱金属或碱土金属盐引入化合物R-NH-CO-OR'中而获得的混合物。
在本文中使用的碱金属盐或碱土金属盐是在环氧化物的存在下加速异氰酸酯预聚物(1)的固化反应的化合物。这些化合物特别包括钠、锂、镁和钾以及铵化合物(优选锂或镁)和任何所需的阴离子的盐,优选与有机酸阴离子如羧酸根,更优选与无机酸阴离子如硝酸根、卤化物、硫酸根、亚硫酸根和磷酸根,更优选与一元酸阴离子如硝酸根或卤化物,特别是硝酸根、氯化物、溴化物或碘化物。特别优选使用氯化锂、溴化锂和二氯化镁,特别是氯化锂。本发明的碱金属或碱土金属盐可单独使用或作为混合物使用。
除了碱金属或碱土金属盐之外,优选不使用其他加速异氰酸酯与对异氰酸酯具有反应性的基团的反应的化合物。
化合物R-NH-CO-OR'是包含至少一个氨基甲酸酯基团的化合物。所述化合物在20℃下优选为固体或优选为液体。在一个优选的实施方案中,R不表示氢和/或不表示COR”。在本文中,R、R’和R”可相同或不同,并且可以为有机化学中已知的任何基团。
此处在催化剂(c)中包含氨基甲酸酯基团的化合物优选可通过由第二多异氰酸酯和具有至少一个OH基团的化合物反应而获得。在此优选在50℃下为液体的化合物,更优选在室温下为液体的那些。在本发明的上下文中的物质或组分为“液体”意指在所述温度下具有不超过10Pas的粘度的那些。如果未指定温度,则数据基于20℃。本文中的测量根据ASTMD445-11进行。包含氨基甲酸酯基团的化合物优选具有至少两个氨基甲酸酯基团。这些包含氨基甲酸酯基团的化合物的分子量优选200至15000g/mol,更优选300至10000g/mol,更具体而言500至1300g/mol。包含氨基甲酸酯基团的化合物可通过例如将上述异氰酸酯(a1)作为第二异氰酸酯与具有至少一个对异氰酸酯具有反应性的氢原子的化合物例如醇反应而获得,所述醇的实例为一元醇如甲醇、乙醇、丙醇、丁醇、戊醇、己醇或更长链的丙氧基化或乙氧基化的一元醇如聚(环氧乙烷)单甲醚,例如来自BASF的单官能产品;二醇,例如乙二醇、二甘醇、三甘醇、丙二醇、二丙二醇、丁二醇、己二醇和/或所述异氰酸酯与上述多元醇(a1)和/或扩链剂的反应产物——单独或混合。为了制备包含氨基甲酸酯基团的化合物,不仅可使用化学计量过量的异氰酸酯而且可使用化学计量过量的多元醇。在使用一元醇时,也可以化学计量比使用异氰酸酯基团和OH基团。当包含氨基甲酸酯基团的化合物的每个分子中具有两个或更多个异氰酸酯基团时,它们可全部或部分替代多异氰酸酯(a2)。在这种情况下,预聚物(a)是在催化剂(c)中包含氨基甲酸酯基团的化合物,不需要进一步加入预聚物(a)。
反应通常在20至120℃的温度下、例如在80℃进行。用于制备包含氨基甲酸酯基团的化合物的第二异氰酸酯优选为二苯甲烷二异氰酸酯的异构体或同系物。更优选地,第二异氰酸酯是二苯甲烷二异氰酸酯单体,例如2,2'-二苯甲烷二异氰酸酯、2,4'-二苯甲烷二异氰酸酯、4,4'-二苯甲烷二异氰酸酯或其混合物。这种二苯甲烷二异氰酸酯也可与其衍生物混合使用。在那种情况下,二苯甲烷二异氰酸酯可特别优选包含最高达10重量%,更特别优选最高达5重量%的碳二亚胺、脲二酮或脲酮亚胺改性的二苯甲烷二异氰酸酯,特别是碳二亚胺改性的二苯甲烷二异氰酸酯。在一个特别优选的实施方案中,用于制备包含氨基甲酸酯基团的化合物的第一异氰酸酯(a)和第二异氰酸酯是相同的。
包含氨基甲酸酯基团的化合物也可通过其他反应途径获得,例如通过使碳酸酯与一元胺反应形成氨基甲酸酯基团。为此,例如碳酸亚丙酯以略微过量(1.1当量)与一元胺(例如Jeffamin M 600)在100℃反应。所得氨基甲酸酯同样可用作包含氨基甲酸酯基团的化合物。
包含碱金属或碱土金属盐和包含氨基甲酸酯基团的化合物的混合物可通过例如在室温或高温下将碱金属或碱土金属盐混合到包含氨基甲酸酯基团的化合物中而获得。这可使用任何混合器完成,例如单个搅拌器(single stirrer)。在这种情况下,碱金属或碱土金属盐可作为纯物质或以溶液形式在单或多官能醇(例如甲醇、乙醇)或扩链剂或水中使用。在一个特别优选的实施方案中,将可商购的基于预聚物的异氰酸酯与溶解的盐直接混合。适合此目的的是例如NCO含量为15%至30%的异氰酸酯预聚物,特别是基于二苯甲烷二异氰酸酯和聚醚多元醇。这种异氰酸酯例如可从BASF以商品名MP102商购。
在本发明的一个特别优选的实施方案中,将碱金属或碱土金属盐溶解在具有对异氰酸酯具有反应性的氢原子的化合物中,随后将所述溶液与异氰酸酯混合,任选地在高温下。
制备包含氨基甲酸酯基团的化合物特别优选使用分子量为30至15000g/mol,优选100至900g/mol的一元醇,在一个特别优选的方案中,400至600g/mol。
根据本发明,调节碱金属或碱土金属盐的量使盐以0.00001至0.1mol每kg异氰酸酯预聚物(a)、环氧化物(b)和催化剂(c)的总重量的量存在。在一个优选的实施方案中,催化剂(c)中相对于每个氨基甲酸酯基团的碱金属离子或碱土金属离子的量为0.0001至3.5,基于催化剂(c)中的碱金属或碱土金属离子和氨基甲酸酯基团的数量计。
除了催化剂(c)之外,剩余的化合物(a)和(b)以及另外的潜在存在的化合物优选包含小于0.0001重量%的碱金属离子或碱土金属离子,基于组分(a)和(b)的总重量计。特别优选组分(a)和(b)中碱金属或碱土金属离子的量小于0.00005,更优选0.00003,更具体而言0.00001重量%,基于组分(a)和(b)以及如果存在的其他化合物的总重量计。
相对于每个环氧基团的碱金属或碱土金属离子的量优选大于0.00001,更优选0.00005至0.3,在每种情况下基于碱金属或碱土金属离子和环氧基团的数量计。
步骤(B)中的反应混合物还可包含另外的异氰酸酯反应性化合物作为多元醇、扩链剂或交联剂。
作为多元醇,例如可使用聚氨酯化学中已知的并且与化合物(a1)相同或不同的聚醚、聚碳酸酯多元醇或聚酯。如果在步骤(B)中将另外的多元醇加入到反应混合物中,在一个优选的实施方案中,它们在异氰酸酯预聚物(a)的形成完成之后被加入。作为另外的多元醇,为了本发明的目的,可使用具有至少两个异氰酸酯反应性基团且分子量为至少350,优选至少400g/mol,更优选至少500g/mol的化合物。存在的异氰酸酯反应性基团可以为例如OH-、SH-、NH-和CH-酸基团。作为异氰酸酯反应性基团,多元醇优选基本上具有OH基团,更优选只有OH基团。在一个优选的实施方案中,多元醇具有至少40%,优选至少60%,更优选至少80%,更具体而言至少95%的仲OH基团,基于异氰酸酯反应性基团的数量计。
使用的多元醇优选为数均分子量为350至12000,优选400至6000,更具体而言500至小于3000,以及优选平均标称官能度为2至6,优选2至3的聚醚醇和/或聚酯醇。在一个优选的实施方案中,如果在混合步骤(B)中使用另外的多元醇,则与多元醇(a1)相同。
在使用低分子量扩链剂和/或交联剂的情况下,可使用在聚氨酯生产中已知的扩链剂,其中扩链剂的官能度为2,交联剂的官能度为3或更高。这些优选具有至少两个异氰酸酯反应性基团的低分子量化合物,并且分子量小于350g/mol、更优选60至小于300g/mol。扩链剂和/或交联剂可用于调节机械性能例如硬度或伸长率。这是本领域技术人员已知的。扩链剂和交联剂的实例包括具有2至14个、优选2至10个碳原子的脂族、脂环族和/或芳脂族或芳族二醇,例如乙二醇、1,3-丙二醇、1,4-丁二醇、1,6-己二醇、1,10-癸二醇和二(2-羟乙基)氢醌、1,2-、1,3-、1,4-二羟基环己烷、二甘醇、二丙二醇、三丙二醇;三醇,例如1,2,4-、1,3,5-三羟基环己烷、丙三醇和三羟甲基丙烷,以及基于环氧乙烷和/或基于1,2-环氧丙烷并以上述二醇和/或三醇作为起始分子的低分子量含羟基的聚环氧烷。其他可能的低分子量的扩链剂和/或交联剂在例如“Kunststoffhandbuch,volume 7,Polyurethane”,CarlHanser Verlag,3rd edition 1993,sections 3.2和3.3.2中详细说明。如果使用扩链剂,则优选使用丙二醇、1,4-丁二醇或1,6-己二醇。优选不使用扩链剂。
向混合步骤(B)中生产的反应混合物中加入另外的多元醇是任选的。优选不使用另外的多元醇。在使用另外的多元醇的情况下,多元醇(d)的基于组分(a)、(b)和(c)的总重量计的比例优选为使得根据步骤(B)的混合在异氰酸酯指数大于200,优选大于500,更优选大于1000时进行的量,最优选在步骤(B)中不加入具有异氰酸酯反应性基团的化合物。为了本发明的目的,异氰酸酯指数是异氰酸酯预聚物(a)的异氰酸酯基团与在步骤(B)中加入到混合物中的异氰酸酯反应性基团的化学计量比乘以100。异氰酸酯反应性基团是反应混合物中存在的所有异氰酸酯反应性基团,包括化学发泡剂和具有环氧基团的化合物,但不包括异氰酸酯基团本身。
可向步骤(B)中生产的反应混合物中加入另外的添加剂。此类添加剂在聚氨酯化学中是众所周知的,包括填料、吸水添加剂、阻燃剂、水解抑制剂、抗氧化剂和内部脱模剂。此类物质在例如“Kunststoffhandbuch,volume 7,Polyurethane”,Carl Hanser Verlag,3rd edition 1993,sections3.4.4和3.4.6至3.4.11中陈述。
使用的吸水添加剂优选为硅铝酸盐,选自硅铝酸钠、硅铝酸钾、硅铝酸钙、硅铝酸铯、硅铝酸钡、硅铝酸镁、硅铝酸锶、磷铝酸钠、磷铝酸钾、磷铝酸钙及其混合物。特别优选在用作载体物质的蓖麻油中的钠、钾、和钙的硅铝酸盐的混合物。
优选吸水添加剂的平均粒径不大于200μm,更优选不大于150μm,更具体而言不大于100μm。本发明的吸水添加剂的孔径优选为2至5埃。除了用于吸水的无机添加剂之外,还可使用用于吸水的已知有机添加剂,例如原甲酸酯、原甲酸三异丙酯。
如果加入吸水添加剂,其加入量优选大于1重量份,更优选1.2至2重量份,基于聚异氰脲酸酯系统的总重量计。
合适的阻燃剂的例子是溴化醚(Ixol B251)、溴化醇,例如二溴新戊醇、三溴新戊醇和PHT-4-二醇;以及氯化磷酸酯,例如磷酸三(2-氯乙基)酯,磷酸三(2-氯异丙基)酯(TCPP)、磷酸三(1,3-二氯异丙基)酯、磷酸三(2,3-二溴丙基)酯和四(2-氯乙基)亚乙基二磷酸酯,或其混合物。
除了已经陈述的卤素取代的磷酸酯,还可使用无机阻燃剂,例如红磷、包含红磷的制剂、可膨胀石墨、氧化铝水合物、三氧化锑、氧化砷、多磷酸铵和硫酸钙;或氰脲酸衍生物,例如三聚氰胺;或至少两种阻燃剂的混合物,如多磷酸铵和三聚氰胺;以及任选地,淀粉;或使根据本发明生产的硬质聚氨酯泡沫具有阻燃性。
作为其他液态无卤阻燃剂,可使用乙基膦酸二乙酯(DEEP)、磷酸三乙酯(TEP)、膦酸二甲基丙酯(DMPP)、磷酸二苯基甲酚基酯(DPC),和其他。
为了本发明的目的,使用的阻燃剂的量优选0至60重量%,更优选5至50重量%,更具体而言5至40重量%,基于组分(a)至(c)的总重量计。
作为内部脱模剂,可使用聚氨酯生产中常用的所有脱模剂,实例为金属盐,例如硬脂酸锌(在二胺溶液中)和聚异亚丁基琥珀酸的衍生物。
本发明的聚氨酯系统优选具有小于0.5重量%,更优选小于0.3重量%的水,基于组分(a)至(c)的总重量计。
例如本发明的反应混合物在25℃下具有超过60分钟的长的开放时间,优选超过90分钟,更优选超过120分钟。所述开放时间通过如上所述的粘度的增加来确定。在温度升高至大于至少80℃的温度时,优选大于80至200℃,更优选90至150℃,例如本发明的反应混合物在少于50分钟内快速固化,优选少于30分钟,更优选少于10分钟,更具体而言为少于5分钟。为了本发明的目的,反应混合物的固化理解为初始粘度增加至初始粘度的10倍。此处在25℃下的开放时间与在130℃下的开放时间的差优选至少40分钟,更优选至少1小时,非常优选至少2小时。在一个优选的实施方案中,固化在加热的模具中进行。
优选通过本发明的方法获得致密的材料,这意味着不加入发泡剂。此处不包括少量发泡剂,例如在加工过程中通过大气水分冷凝进入反应混合物或起始组分的少量水。致密聚氨酯是基本上不含气体夹杂物的聚氨酯。致密聚氨酯的密度优选大于0.8g/cm3,更优选大于0.9g/cm3,更具体而言大于1.0g/cm3。
通过本发明的方法可获得的聚氨酯弹性体在优选小于90邵氏A的相对低硬度值和低磨损值下显示良好的机械性能,如低压缩变形、高弹性和高拉伸强度。此外,本发明聚氨酯的生产导致低收缩值。因此,本发明的方法非常适合聚氨酯密封料或聚氨酯辊的生产,特别是需要长的开放时间和快速固化的大型的辊或大型的密封料。
在下文中,通过实施例阐述本发明:
输入材料:
异氰酸酯1 4,4'-二苯基甲烷二异氰酸酯(4,4'-MDI),摩尔质量为250.26g/mol
异氰酸酯2 2,4-甲苯二异氰酸酯和2,6-甲苯二异氰酸酯的混合物(80:20)
多元醇1 OH值约56的聚醚二醇(分子量:约2000),由四氢呋喃构造
多元醇2 OH值约为56、官能度约为2的聚醚二醇(分子量:约2000),由丙二醇和环氧丙烷(PO)构造
多元醇3 OH值约为56、官能度为2的聚酯二醇(分子量:约2000),由己二酸、1,2-乙二醇和1,4-丁二醇构造
多元醇4 OH值为约56、官能度为2的聚酯二醇(分子量:约2500),由己二酸和1,4-丁二醇构造
多元醇5 OH值约为104、官能度约为2的聚醚二醇(分子量:约1000),由丙二醇和环氧丙烷(PO)构造
多元醇6 OH值约为248、官能度约为2的聚醚二醇(分子量:约450),由丙二醇和环氧丙烷(PO)构造
多元醇7 OH值约为28、官能度约为2的聚醚二醇(分子量:约4000),由丙二醇和环氧丙烷(PO)构造
环氧化物 基于双酚A的二缩水甘油醚,例如来自Huntsman的Araldite GY250
添加剂1 二甘醇二氯甲酸酯
添加剂2 消泡剂,例如来自Momentive的AF9000 NE有机硅消泡剂
添加剂3 蓖麻油中的K-Ca-Na-沸石A
催化剂1 异氰酸酯3与数均分子量为500g/mol的单官能聚环氧乙烷的反应产物(可从BASF以商品名“A500E”获得)为与LiCl的混合物;0.50当量的LiCl,基于本发明的氨基甲酸酯化合物的数量计
催化剂2 乙酸钾
催化剂3 LiCl和脲预聚物的混合物(非本发明),可通过Jeffamin M600和异氰酸酯3以及0.70当量的LiCl(基于预聚物中脲化合物数量计)反应而获得,例如WO10121898相应记载。
扩链剂1 1,4-丁二醇
比较例和发明例:
1.预聚物
预聚物的生产
异氰酸酯最初在约50℃下加入到配置有PT100热电偶、氮气进料器、搅拌器和加热套的4000 ml的圆颈烧瓶中,并在此温度下加入多元醇。将反应混合物加热至80℃并在80℃下搅拌2小时。然后使所得预聚物达到室温,无需进一步处理即可用于以下应用。
预聚物1 | 预聚物2 | 预聚物3 | |
异氰酸酯1[g] | 26.50 | 24.70 | 25.0 |
多元醇1[g] | 73.48 | ||
多元醇2[g] | 75.29 | ||
多元醇3[g] | 75.0 | ||
添加剂1[g] | 0.02 | 0.01 | |
NCO[%] | 5.6 | 5.2 | 5.2 |
预聚物4 | 预聚物5 | 预聚物6 | |
异氰酸酯1[g] | 20 | 35 | 50 |
多元醇3[g] | 80 | 65 | 50 |
NCO[%] | 3.3 | 8.9 | 14.7 |
2.弹性体、密封料和粘合剂
基于预聚物的聚氨酯的生产
将组分(参见配方)在真空速度混合器中以1800 rpm混合20秒,然后倒入阶梯模具(110℃)中。随后将固化的测试片在90℃下调节24 h。
固体聚氨酯和所得试样的性能:
所得聚氨酯的以下性能通过所述方法测定:
密度:DIN EN ISO 1183-1,A。
硬度(邵氏A/D):DIN ISO 7619-1
拉伸强度/断裂伸长率:DIN 53504
抗撕裂性:DIN ISO 34-1,B(b)
磨损测量:DIN ISO 4649
玻璃化转变温度:Tg通过差示扫描量热法测定。
固化和机械性能:反应混合物的配方:
比较例1、3至6 | 比较例2 | 实施例1至7 | |
预聚物 | 91.5 | 94.5 | 91.5 |
催化剂[g] | 1 | 3 | 1 |
环氧化物[g] | 5 | - | 5 |
添加剂2[g] | 0.5 | 0.5 | 0.5 |
添加剂3[g] | 2 | 2 | 2 |
实施例显示在选定的NCO范围内,如果使用本发明的多元醇生产预聚物,可获得非常好的机械性能,特别是伸长率和压缩变形,且硬度小于90邵氏A。如果使用非本发明的朝向阴离子的双配位基催化剂,例如WO10121898中公开的这种催化剂,合理的催化剂的量对高温下固化而言是不足的。当大量使用时,例如10重量份而不是1重量份,固化可以在高温下发生,但是如此大量的催化剂是不良的,并且导致所获得的弹性体的机械性能的不希望的劣化。
下表显示了在其他异氰酸酯反应性组分存在下固化的配方。
具有共聚醇或扩链剂的反应混合物的配方:
本发明的配制方在另外的异氰酸酯反应性组分的存在下固化,在室温下显示长的开放时间以及在高于80℃的温度下显示快速固化。
Claims (13)
1.一种聚氨酯弹性体的制备方法,包括以下步骤:
A)制备异氰酸酯预聚物(a),通过混合
(a1)至少一种包含选自聚酯多元醇、聚醚多元醇或其混合物的多元醇的异氰酸酯反应性组合物,所述多元醇平均官能度在≥1.8至≤2.5的范围内和OH值在≥20mg KOH/g至≤450mg KOH/g的范围内,
和
(a2)至少一种多异氰酸酯,
并使混合物反应形成异氰酸酯预聚物(a)而进行,其中异氰酸酯预聚物的异氰酸酯含量在≥1重量%至≤9重量%范围内,
和
B)通过在至少一种催化剂(c)的存在下将至少一种环氧化物(b)与异氰酸酯预聚物(a)混合来制备反应混合物,其中催化剂(c)是可通过将碱金属或碱土金属盐引入化合物R-NH-CO-OR’而获得的混合物,其中R和R’可以相同或不同并且可为有机化学里任何已知的基团,其中碱金属或碱土金属盐的量为0.00001至0.1mol每kg异氰酸酯预聚物(a)、环氧化物(b)和催化剂(c)的总重量,和
C)将混合物加热至至少80℃以获得聚氨酯弹性体。
2.根据权利要求1所述的方法,其特征在于催化剂(c)通过将碱金属或碱土金属盐引入至异氰酸酯预聚物(a)的至少一部分中而获得。
3.根据权利要求1所述的方法,其特征在于第一多异氰酸酯用作多异氰酸酯(a2),并且在催化剂(c)中的含氨基甲酸酯基团的化合物为第二多异氰酸酯和具有OH基团的化合物的反应产物。
4.根据权利要求1至3中一项或更多项所述的方法,其特征在于催化剂(c)中相对于每个氨基甲酸酯基团的碱金属离子或碱土金属离子的量为0.0001至3.5,基于催化剂(c)中碱金属或碱土金属离子和氨基甲酸酯基团的数量计。
5.根据权利要求1至4中一项或更多项所述的方法,其特征在于碱金属盐或碱土金属盐为氯化锂。
6.根据权利要求1至5中一项或更多项所述的方法,其特征在于根据步骤B)的混合在异氰酸酯指数大于200的情况下进行。
7.根据权利要求1至6中一项或更多项所述的方法,其特征在于异氰酸酯反应性组分(a1)包含聚四氢呋喃。
8.根据权利要求1至7中一项或更多项所述的方法,其特征在于异氰酸酯反应性组分(a1)包含通过起始分子的烷氧基化而获得的聚醚多元醇,其中环氧烷烃包含至少70重量%的环氧丙烷。
9.根据权利要求1至8中一项或更多项所述的方法,其特征在于异氰酸酯反应性组分(a1)包含通过己二酸和丁二醇的酯化而获得的聚酯醇。
10.根据权利要求1至9中一项或更多项所述的方法,其特征在于异氰酸酯(a2)包含单体芳族二异氰酸酯。
11.根据权利要求1至10中一项或更多项所述的方法,其特征在于待在步骤(B)中使用的异氰酸酯预聚物包含小于1重量%的二异氰酸酯单体。
12.根据权利要求1至11中任一项所述的方法而获得的聚氨酯弹性体。
13.根据权利要求12所述的聚氨酯弹性体作为辊的一部分或密封料的用途。
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