CN114144259A - 用于聚氨酯发泡体的酸封闭的吡咯烷催化剂 - Google Patents
用于聚氨酯发泡体的酸封闭的吡咯烷催化剂 Download PDFInfo
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- CN114144259A CN114144259A CN202080051942.6A CN202080051942A CN114144259A CN 114144259 A CN114144259 A CN 114144259A CN 202080051942 A CN202080051942 A CN 202080051942A CN 114144259 A CN114144259 A CN 114144259A
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- polyurethane
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- -1 olefin compound Chemical class 0.000 claims abstract description 36
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- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 4
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- Polyurethanes Or Polyureas (AREA)
Abstract
本发明涉及用于聚氨酯配制物的酸封闭的吡咯烷催化剂。该聚氨酯配制物包括酸封闭的吡咯烷催化剂，含有异氰酸酯官能团的化合物，含活性氢的化合物和卤化烯烃化合物。使用这样的酸封闭的吡咯烷催化剂表现出与卤化烯烃化合物的令人惊讶的低反应性，但是对于催化聚氨酯形成来说足够的反应性。
Description
交叉参考的相关申请
本申请要求2019年7月18日提交的美国临时专利申请62/875,629的优先权。所述申请通过参考引入本文。
关于联邦发起的研究或开发的声明
不适用。
技术领域
本发明总体上涉及用于生产软质和硬质聚氨酯发泡体和其他聚氨酯材料的酸封闭的吡咯烷催化剂。
背景技术
聚氨酯发泡体是广泛已知的，并且用于多种应用中，例如用于汽车和住宅工业。这些发泡体通过多异氰酸酯与多元醇在不同的添加剂存在下反应来生产。一种这样的添加剂是胺催化剂，其用于加速发泡(水与多异氰酸酯反应来产生CO2)和凝胶化(多元醇与多异氰酸酯的反应)。
在聚氨酯发泡体生产中使用常规胺催化剂(例如双二甲基氨基乙基醚)的缺点包括：由于它们的高挥发性而导致发生安全和毒性问题，这导致空气携带的蒸气，其被认为导致了蓝灰视障(glaucopsia)，也称作蓝雾(blue haze)或目晕(halovision)，其是视觉清晰度的一种临时失调；这些催化剂生产的汽车内部发泡体所引起的汽车挡风玻璃的雾化；和恶臭性能。
另外，许多胺催化剂在与某些发泡剂一起使用时也是不稳定的，特别是与更新的、低全球变暖潜力(GWP)卤化烯烃发泡剂例如反式-1-氯-3,3,3-三氟丙烯(称作1233zd(E))或顺式-1,1,1,3,3,3-六氟-2-丁烯(称作1366mzz(Z))一起使用时，由于它们的活化双键，其会与胺反应。已经进行了不同的尝试来改进含有胺和卤化烯烃发泡剂的共混物的存储寿命，而不影响它们以合理速率催化聚氨酯发泡体配制物的能力。大部分的这些尝试聚焦于使用这样的胺，其是以一种方式或另一方式失活的(例如用吸电子基团来空间受阻的或键合的)或者通过包括添加剂来防止它们与卤化烯烃发泡剂反应(参见例如US10023681，US20150266994A1，US20160130416A1，US9550854，US9556303B2，US10308783B2，US9868837B2，US20190177465A1)。但是，这样的尝试仍未实现具有存储寿命稳定性和催化活性的共混物，其与含有胺和常规的非卤化发泡剂的共混物相当。
因此，一直需要开发用于生产硬质或软质聚氨酯发泡体和其他聚氨酯材料的新型胺催化剂，其可以与上述的更新的、低全球变暖潜力(GWP)卤化烯烃发泡剂相组合来形成具有可接受的催化活性和相比于目前的常规胺催化剂来说改进的存储寿命的共混物。
发明内容
本发明提供一种聚氨酯配制物，其包含酸封闭的吡咯烷催化剂，卤化烯烃化合物，含有异氰酸酯官能团的化合物和含活性氢的化合物。
根据另一实施方案，提供了一种催化剂包，其用于例如但不限于形成包含酸封闭的吡咯烷催化剂和卤化烯烃化合物的聚氨酯材料。
在又一实施方案中，提供一种形成聚氨酯材料的方法，其包括将含有异氰酸酯官能团的化合物，含活性氢的化合物和任选的辅助组分在酸封闭的吡咯烷催化剂和卤化烯烃化合物存在下接触。
附图说明
图1显示了使用酸封闭的工业常规催化剂以及本发明的酸封闭的吡咯烷催化剂生产的聚氨酯发泡体在50℃存储之前和之后的消粘时间。
具体实施方式
下面的术语应当具有下面的含义：
术语“包含/包括”及其派生词并非打算排除任何另外的组分、步骤或程序的存在，无论其是否在此公开。为了避免任何疑义，本文通过使用术语“包含/包括”要求保护的全部组合物可以包含任何另外的添加剂或化合物，除非有相反指示。相反，术语“基本上由……组成”如果在本文出现，则从任何随后引用的任何其他组分、步骤或程序的范围中排除，除了对于操作性来说并非本质的那些之外，和术语“由……组成”在使用时排除没有明确描述或列举的任何组分、步骤或程序。除非另有规定，否则术语“或”指的是列举的单个以及任意组合的元素。
冠词“一个”和“一种”在此用于表示一个/种或多于一个/种(即至少一个/种)的该冠词的语法宾语。作为例子，“一种催化剂”表示一种催化剂或多于一种催化剂。措辞“在一个实施方案中”、“根据一个实施方案”等通常表示该措辞之后的具体特征、结构或特性包括在本发明的至少一个实施方案中，并且可以包括在本发明的多于一个实施方案中。重要地，这样的措辞不必需指的是相同的方面。如果说明书声称组分或特征“可以”、“能够”、“能”或“可能”被包括或具有一定特性，即该具体组分或特征不需要被包括或具有该特性。
如本文所使用，术语“约”可以允许在值或范围中的一定的变化度，例如它可以处于所述值或所述范围限度的10％内，5％内或1％内。
以范围形式表达的值应当以灵活方式解释为不仅包括作为该范围限度而明确表述的数值，而且还包括囊括在那个范围内的全部单个数值或子范围，如同每个数值和子范围明确表述一样。例如，范围例如1-6应当被认为已经明确公开了子范围例如1-3，2-4，3-6等，以及那个范围内的单个数例如1，2，3，4，5和6。这是适用的，无论范围幅度如何。
术语“优选的”和“优选地”指的是在某些情形下可以提供某些益处的实施方案。但是，其他实施方案在相同的或其他情形下也可以是优选的。此外，一个或多个优选的实施方案的表述不意味着其他实施方案不可使用，并非打算从本发明范围内排除其他实施方案。
术语“基本上不含”指的是这样的组合物，其中具体化合物或结构部分的存在量不实质性影响该组合物。在一些实施方案中，“基本上不含”可以指的是这样的组合物，其中具体化合物或结构部分在该组合物中的存在量小于2重量％，或小于1重量％，或小于0.5重量％，或小于0.1重量％，或小于0.05重量％，或甚至小于0.01重量％，基于该组合物的总重量计，或者具体化合物或结构部分在各自组合物中没有存在量。
在取代基以它们的常规化学式(从左到右书写)来规定的情况中，它们同等地囊括化学上相同的取代基，其将由从右到左书写的结构来产生，例如-CH2O-等价于-OCH2-。
术语“烷基”指的是具有1-10个碳原子的直链或支链饱和烃基。在一些实施方案中，烷基取代基可以是低级烷基。术语“低级”指的是具有1-6个碳原子的烷基。“低级烷基”的例子包括但不限于甲基，乙基，正丙基，异丙基，丁基和戊基。
术语“卤化烯烃”指的是烯烃化合物或结构部分，其可以包括氟，氯，溴或碘。
术语“任选的”或“任选地”表示随后所述的事件或情形可以发生或可以不发生，并且该描述包括其中发生所述的事件或情形的情况，和其中不发生所述的事件或情形的情况。
本发明总体上涉及新颖的酸封闭的吡咯烷催化剂和它们在聚氨酯配制物中的用途，其可以包括含有异氰酸酯官能团的化合物，含活性氢的化合物和作为发泡剂的卤化烯烃化合物。本发明还涉及硬质或软质聚氨酯发泡体或其他聚氨酯材料，其由包含本文所述的酸封闭的吡咯烷催化剂，含有异氰酸酯官能团的化合物，含活性氢的化合物和作为发泡剂的卤化烯烃化合物的配制物制成。如本文所使用，术语“聚氨酯”被理解为囊括纯聚氨酯，聚氨酯聚脲和纯聚脲。已经令人惊讶地发现，根据本发明，将卤化烯烃化合物发泡剂与酸封闭的吡咯烷催化剂相组合，以代替大部分或代替全部的常规胺催化剂，这产生了具有改进的存储寿命稳定性和催化活性的共混物。
根据一个实施方案，酸封闭的吡咯烷催化剂是式(1)或式(2)中的至少一个所示的一种或多种催化剂：
其中x是1-10的整数和A是酸性化合物的离子，其中该酸性化合物具有式(OH)n-R-(COOH)m，其中R是氢、烷基、烯基、脂环族的、芳族的或烷基芳族的基团，n和m是0-3的整数，条件是n+m≥1，并且当n＝1和m＝0时，R是芳族的或烷基芳族的。
根据一个实施方案，x是1-9，或1-8，或1-7，或1-6，或1-5，或1-4的整数。在一个具体实施方案中，x是2、3或4。在另一实施方案中，x是使得(CH2)x基团是低级烷基的整数。
根据本发明的另一实施方案，每个A具有1-10个碳原子和A是羧酸，二羧酸，三羧酸，酚酸，取代的酚酸或其羟基取代的衍生物的离子。
R烷基的例子包括但不限于甲基，乙基，正丙基，异丙基，丙基，丁基，异丁基，苯基，乙烯基，正戊基，正癸基或2-乙基己基。虽然前述烷基可以包含两个可利用的取代位置，但是可以想到烃上另外的氢可以用另外的羧基和/或羟基取代。
可以用作组分A的具体化合物包括但不限于羟基羧酸，二羧酸，甲酸，乙酸，丙二酸，戊二酸，马来酸，乙醇酸，乳酸，2-羟基丁酸，柠檬酸，AGS酸，酚，甲酚，对苯二酚，或其组合。AGS酸是二羧酸(即己二酸，戊二酸和琥珀酸)的混合物，其作为己二酸制造方法中环己醇和/或环己酮氧化的副产物而获得。可以用作组分A的合适的AGS酸包括
酸(可获自Solvay S.A.)，DIBASIC酸(可获自Invista S.a.r.l)，FLEXATRACTM-AGS-200酸(可获自Ascend Performance Materials LLC)，和工业级戊二酸(AGS)(获自Lanxess A.G.)。
在一个实施方案中，式(1)和(2)的酸封闭的吡咯烷催化剂可以通过在聚氨酯配制物中，通过将吡咯烷和式(OH)n-R-(COOH)m的化合物分别添加到该聚氨酯配制物中来原位制备，而在其他实施方案中，上述酸封闭的吡咯烷催化剂可以在添加到聚氨酯配制物之前制备。
根据另一实施方案，式(1)或(2)的酸封闭的吡咯烷催化剂可以与式(3)的吡咯烷催化剂相组合来形成催化剂混合物。
式(3)的吡咯烷催化剂可以与式(1)或(2)(或(1)和(2))的酸封闭的吡咯烷催化剂以约0.1重量％至约99.9重量％的量相组合，基于该催化剂混合物的总重量计。在另一实施方案中，式(3)的吡咯烷催化剂可以与式(1)或(2)(或(1)和(2))的酸封闭的吡咯烷催化剂以约1重量％至约90重量％，或约10重量％至约80重量％，或约20重量％至约70重量％，或约30重量％至约60重量％，或约40重量％至约50重量％的量相组合，基于该催化剂混合物的总重量计。
根据一些实施方案，式(1)和/或(2)的酸封闭的吡咯烷催化剂(和任选的式(3)的吡咯烷催化剂)可以单独用于形成聚氨酯发泡体或材料。在仍然其他实施方案中，上述催化剂可以与含有至少一个叔胺基团的胺催化剂和/或非胺催化剂相组合来用于形成聚氨酯发泡体或材料。在酸封闭的吡咯烷催化剂(1)和/或(2)与含有至少一个叔胺基团的胺催化剂和/或非胺催化剂相组合的实施方案中，式(1)和/或(2)的酸封闭的吡咯烷催化剂与含有至少一个叔胺基团的胺催化剂和/或非胺催化剂的重量比是至少1:1，和在一些实施方案中是至少1.5:1，和在仍然其他实施方案中是至少2:1，和在另一实施方案中是至少5:1，而在又一实施方案中是至少10:1。在仍然其他实施方案中，式(1)和/或(2)的酸封闭的吡咯烷催化剂与含有至少一个叔胺基团的胺催化剂和/或非胺催化剂的重量比是0.1:99.9至99.9:0.1，和在仍然其他实施方案中是1:99至99:1，和在仍然其他实施方案中是5:95至95:5，和在另一实施方案中是10:90至90:10，而在又一实施方案中是25:75至75:25。
代表性的含有至少一个叔胺基团的胺催化剂包括但不限于双-(2-二甲基氨基乙基)醚(
ZF-20催化剂)，N,N,N'-三甲基-N'-羟乙基双氨基乙基醚(
ZF-10催化剂)，N-(3-二甲基氨基丙基)-N,N-二异丙醇胺(
DPA催化剂)，N,N-二甲基乙醇胺(
DMEA催化剂)，三乙烯二胺(
TEDA催化剂)，N,N-二甲基乙醇胺乙烯二胺的共混物(例如
TD-20催化剂)，N,N-二甲基环己基胺(
DMCHA催化剂)，苄基二甲基胺(
BDMA催化剂)，五甲基二乙基醚胺(
PMDETA催化剂)，N,N,N',N”,N”-五甲基二丙烯三胺(
ZR-40催化剂)，N,N-双(3-二甲基氨基丙基)-N-异丙醇胺(
ZR-50催化剂)，N'-(3-(二甲基氨基)丙基-N,N-二甲基-1,3-丙烷二胺(
Z-130催化剂)，2-(2-二甲基氨基乙氧基)乙醇(
ZR-70催化剂)，N,N,N-三甲基氨基乙基-乙醇胺(
Z-110催化剂)，N-乙基吗啉(
NEM催化剂)，N-甲基吗啉(
NMM催化剂)，4-甲氧基乙基吗啉，N,N'-二甲基哌嗪(
DMP催化剂)，2,2'-二吗啉基二乙基醚(
DMDEE催化剂)，1,3,5-三(3-(二甲基氨基)丙基)-六氢-s-三嗪(
TR-90催化剂)，1-丙烷胺，3-(2-(二甲基氨基)乙氧基)，取代的咪唑例如1,2-二甲基咪唑和1-甲基-2-羟乙基咪唑，N,N'-二甲基哌嗪或双取代的哌嗪如氨基乙基哌嗪，N,N',N'-三甲基氨基乙基哌嗪或双-(N-甲基哌嗪)脲，N-甲基吡咯烷和取代的甲基吡咯烷例如2-氨基乙基-N-甲基吡咯烷或双-(N-甲基吡咯烷)乙基脲，3-二甲基氨基丙基胺，N,N,N”,N”-四甲基二丙烯三胺，四甲基胍，1,2-双-二异丙醇。胺催化剂的其他例子包括N-烷基吗啉，例如N-甲基吗啉，N-乙基吗啉，N-丁基吗啉和二吗啉基二乙基醚，N,N'-二甲基氨基乙醇，N,N-二甲基氨基乙氧基乙醇，双-(二甲基氨基丙基)-氨基-2-丙醇，双-(二甲基氨基)-2-丙醇，双-(N,N-二甲基氨基)乙基醚；N,N,N'-三甲基-N'-羟乙基-双-(氨基乙基)醚，N,N-二甲基氨基乙基-N'-甲基氨基乙醇和四甲基亚氨基双丙基胺。前述的
催化剂可获自美国德克萨斯州伍德兰兹的Huntsman Petrochemical LLC。
可以用于本发明的其他胺催化剂可以在Herrington等人的“Dow PolyurethanesFlexible Foams”的附录D，第D.1-D.23页(1997)中找到，其通过参考引入本文。另外的例子可以在“
Amine Catalysts for the Polyurethane Industry”的JCT-0910版中找到，其通过参考引入本文。
非胺催化剂是具有用于异氰酸酯基团与多元醇或水反应的催化活性的化合物(或其混合物)，但不是落入上述胺催化剂的说明中的化合物。这样的另外的非胺催化剂的例子包括，例如：
叔膦例如三烷基膦和二烷基苄基膦；
不同金属的螯合物，例如可以获自乙酰基丙酮，苯甲酰丙酮，三氟乙酰基丙酮，乙酰乙酸乙酯等的那些，其中金属例如是Be，Mg，Zn，Cd，Pd，Ti，Zr，Sn，As，Bi，Cr，Mo，Mn，Fe，Co和Ni；
金属羧酸盐例如乙酸钾和乙酸钠；
强酸的酸性金属盐，例如氯化铁，氯化锡，氯化亚锡，三氯化锑，硝酸铋和氯化铋；
强碱，例如碱金属和碱土金属氢氧化物，烷氧化物和苯氧化物；
不同金属的醇盐和酚盐，例如Ti(OR6)4，Sn(OR6)4和Al(OR6)3，其中R6是烷基或芳基，和醇盐与羧酸，β-二酮和2-(N,N-二烷基氨基)醇的反应产物；
碱土金属，Bi，Pb，Sn或Al的羧酸盐；和四价锡化合物，和三价或五价铋、锑或砷化合物。
式(1)和/或(2)的酸封闭的吡咯烷催化剂可以以催化有效量使用来催化用于制造硬质或软质聚氨酯发泡体或其他聚氨酯材料的含有异氰酸酯官能团的化合物与含活性氢的化合物之间的反应。式(1)和/或(2)的酸封闭的吡咯烷催化剂的催化有效量可以是约0.01至15份/100份含活性氢的化合物，和在一些实施方案中是约0.05至12.5份/100份含活性氢的化合物，和在甚至另一实施方案中是约0.1至7.5份/100份含活性氢的化合物，和仍然在甚至另一实施方案中是约0.5至5份/100份含活性氢的化合物。
在一个实施方案中，含有异氰酸酯官能团的化合物是多异氰酸酯和/或异氰酸酯端接的预聚物。
多异氰酸酯包括通式Q(NCO)a所示的那些，其中a是2-5，例如2-3的数，和Q是含有2-18个碳原子的脂肪族烃基，含有5-10个碳原子的脂环族烃基，含有8-13个碳原子的芳脂族烃基，或含有6-15个碳原子的芳烃基。
多异氰酸酯的例子包括但不限于亚乙基二异氰酸酯；1,4-四亚甲基二异氰酸酯；1,6-六亚甲基二异氰酸酯；1,12-十二烷二异氰酸酯；环丁烷-1,3-二异氰酸酯；环己烷-1,3-和1,4-二异氰酸酯，和这些异构体的混合物；异佛尔酮二异氰酸酯；2,4-和2,6-六氢甲苯二异氰酸酯和这些异构体的混合物；二环己基甲烷-4,4'-二异氰酸酯(氢化的MDI，或HMDI)；1,3-和1,4-亚苯基二异氰酸酯；2,4-和2,6-甲苯二异氰酸酯和这些异构体的混合物(TDI)；二苯基甲烷-2,4'-和/或-4,4'-二异氰酸酯(MDI)；亚萘基-1,5-二异氰酸酯；三苯基甲烷-4,4',4”-三异氰酸酯；下述类型的多苯基-多亚甲基-多异氰酸酯，其可以通过将苯胺与甲醛缩合，随后光气化来获得(粗MDI)；降冰片烷二异氰酸酯；间-和对-异氰酸酯根合苯基磺酰基异氰酸酯；全氯化的芳基多异氰酸酯；含有碳二酰亚胺基团，氨酯基团，脲基甲酯基团，异氰尿酸酯基团，脲基或缩二脲基团的改性的多异氰酸酯；通过调聚反应获得的多异氰酸酯；含有酯基的多异氰酸酯；和含有聚合物脂肪酸基团的多异氰酸酯。本领域技术人员将认可还可以使用上述的多异氰酸酯的混合物。
异氰酸酯端接的预聚物也可以用于制备聚氨酯。异氰酸酯端接的预聚物可以将过量的多异氰酸酯或其混合物与少量的含活性氢的化合物反应来制备，如通过公知的泽列维季诺夫(Zerewitinoff)测试确定的。
在另一实施方案中，含活性氢的化合物是多元醇。适用于本发明的多元醇包括但不限于聚亚烷基醚多元醇，聚酯多元醇，聚合物多元醇，不易燃多元醇例如含磷的多元醇或含卤素的多元醇。这样的多元醇可以单独使用或作为混合物来合适的组合使用。
聚亚烷基醚多元醇包括聚(环氧烷)聚合物例如聚环氧乙烷和聚环氧丙烷聚合物和具有衍生自多羟基化合物(包括二醇和三醇)的端羟基的共聚物；例如乙二醇，丙二醇，1,3-丁二醇，1,4-丁二醇，1,6-己二醇，新戊二醇，二甘醇，二丙二醇，季戊四醇，甘油，二甘油，三羟甲基丙烷和类似的低分子量多元醇。
聚酯多元醇包括但不限于通过二羧酸与过量二醇反应例如己二酸与乙二醇或丁二醇反应生产的那些，或者内酯与过量二醇反应例如己内酯与丙二醇反应生产的那些。
除了聚亚烷基醚多元醇和聚酯多元醇之外，聚合物多元醇也适用于本发明。聚合物多元醇用于聚氨酯材料中来增加抗变形性，例如来改进发泡体或材料的承重性能。聚合物多元醇的例子包括但不限于接枝多元醇或聚脲改性的多元醇(PolyharnstoffDispersion多元醇)。接枝多元醇包含三醇，其中乙烯基单体是接枝共聚的。合适的乙烯基单体包括例如苯乙烯，或丙烯腈。聚脲改性的多元醇是这样的多元醇，其含有通过二胺和二异氰酸酯在多元醇存在下反应形成的聚脲分散体。聚脲改性的多元醇的一种变体是多异氰酸酯加聚(PIPA)多元醇，其通过异氰酸酯和烷醇胺在多元醇中的原位反应来形成。
不易燃的多元醇可以例如是含磷的多元醇，其可以通过将环氧烷加成到磷酸化合物来获得。含卤素的多元醇可以例如是可以通过表氯醇或三氯环氧丁烷的开环聚合获得的那些。
聚氨酯配制物还可以含有充当发泡剂的一种或多种卤化烯烃化合物。卤化烯烃化合物包含至少一种包含3-4个碳原子和至少一个碳-碳双键的卤代烯烃(例如氟烯烃或氯氟烯烃)。合适的化合物可以包括氢卤化烯烃例如三氟丙烯，四氟丙烯(例如四氟丙烯(1234))，五氟丙烯(例如五氟丙烯(1225))，氯三氟丙烯(例如氯三氟丙烯(1233))，氯二氟丙烯，氯三氟丙烯，氯四氟丙烯，六氟丁烯(例如六氟丁烯(1336))，或其组合。在某些实施方案中，四氟丙烯，五氟丙烯和/或氯三氟丙烯化合物具有不多于一个的连接到不饱和碳链的端碳原子的氟或氯取代基(例如1,3,3,3-四氟丙烯(1234ze)；1,1,3,3-四氟丙烯，1,2,3,3,3-五氟丙烯(1225ye)，1,1,1-三氟丙烯，1,2,3,3,3-五氟丙烯，1,1,1,3,3-五氟丙烯(1225zc)，1,1,2,3,3-五氟丙烯(1225yc)，(Z)-1,1,1,2,3-五氟丙烯(1225yez)，1-氯-3,3,3-三氟丙烯(1233zd)，1,1,1,4,4,4-六氟丁-2-烯(1336mzzm)，或其组合)。
可以与上述的卤化烯烃化合物组合使用的其他发泡剂包括空气，氮气，二氧化碳，氢氟烃(“HFC”)，烷烃，烯烃，单羧酸盐，酮，醚，或其组合。合适的HFC包括1,1-二氟乙烷(HFC-152a)，1,1,1,2-四氟乙烷(HFC-134a)，五氟乙烷(HFC-125)，1,1,1,3,3-五氟丙烷(HFC-245fa)，1,1,1,3,3-五氟丁烷(HFC-365mfc)，或其组合。合适的烷烃和烯烃包括正丁烷，正戊烷，异戊烷，环戊烷，1-戊烯，或其组合。合适的单羧酸盐包括甲酸甲酯，甲酸乙酯，乙酸甲酯，或其组合。合适的酮和醚包括丙酮，二甲醚，或其组合。
另外，聚氨酯配制物可以任选地包括一种或多种辅助组分。辅助组分的例子包括但不限于泡孔稳定剂，表面活性剂，扩链剂，颜料，填料，阻燃剂，可热膨胀微球，水，增稠剂，防烟剂，增强剂，抗氧化剂，UV稳定剂，抗静电剂，红外辐射吸收剂，染料，脱模剂，抗真菌剂，杀生物剂，或其任意组合。
泡孔稳定剂可以包括例如硅表面活性剂或阴离子表面活性剂。合适的硅表面活性剂的例子包括但不限于聚烷基硅氧烷，聚氧亚烷基多元醇改性的二甲基聚硅氧烷，烷二醇改性的二甲基聚硅氧烷，或其任意组合。
合适的表面活性剂包括乳化剂和发泡稳定剂，例如本领域已知的硅酮表面活性剂例如聚硅氧烷，以及不同的脂肪酸的胺盐，例如二乙基胺油酸盐或二乙醇胺硬脂酸盐，以及蓖麻油酸的钠盐。
扩链剂的例子包括但不限于具有羟基或氨基官能团的化合物，例如二醇，胺，二醇和水。扩链剂的另外的非限定性例子包括乙二醇，丙二醇，1,4-丁二醇，1,3-丁二醇，1,5-戊二醇，1,6-己二醇，1,10-癸二醇，1,12-十二烷二醇，乙氧化的对苯二酚，1,4-环己二醇，N-甲基乙醇胺，N-甲基异丙醇胺，4-氨基环己醇，1,2-二氨基乙烷，或其任意混合物。
颜料可以用于在制造过程中对聚氨酯材料进行颜色编码，来识别产品等级，或遮掩黄变。颜料可以包括任何合适的有机或无机颜料。例如，有机颜料或着色剂包括但不限于偶氮/二偶氮染料，酞菁染料，二噁嗪，或炭黑。无机颜料的例子包括但不限于二氧化钛，铁氧化物，或氧化铬。
填料可以用于增加聚氨酯发泡体或材料的密度和承重性能。合适的填料包括但不限于硫酸钡，炭黑，或碳酸钙。
阻燃剂可以用于降低可燃性。例如，这样的阻燃剂包括但不限于氯化的磷酸酯，氯化石蜡，或蜜胺粉末。
可热膨胀微球包括含有(环)脂肪族烃的那些。这样的微球通常是干燥的、未膨胀的或部分未膨胀的微球，其由平均直径通常是10-15微米的小的球形颗粒组成。该球由气密性聚合物壳(例如由丙烯腈或PVDC组成)形成，其包纳着一分钟滴下的(环)脂肪族烃例如液体异丁烷。当这些微球在升高的温度水平(例如150℃至200℃)进行足以软化热塑性壳和使得其中包封的(环)脂肪族烃挥发的加热时，形成的气体使壳膨胀和增加微球的体积。当膨胀时，微球的直径是它们初始直径的3.5至4倍，作为其结果，它们的膨胀体积比它们在未膨胀态时初始体积增大约50至60倍。这样的微球的例子是
-DU微球，其由瑞典的AKZO Nobel Industries销售。
由根据本发明的聚氨酯配制物生产聚氨酯材料的方法是本领域技术人员公知的，并且可以例如在美国专利号5,420,170，5,648,447，6,107,359，6,552,100，6,737,471和6,790,872中找到，其内容通过参考引入本文。不同类型的聚氨酯材料可以制造例如硬质发泡体，软质发泡体，半软质发泡体，微泡孔弹性体，纺织品衬背，喷雾弹性体，流延弹性体，聚氨酯-异氰尿酸酯发泡体，反应注塑聚合物，结构反应注塑聚合物等。
通用的含有式(1)和(2)的酸封闭的吡咯烷催化剂的密度为15至150kg/m3的软质聚氨酯发泡体配制物的一个非限定性例子(例如汽车座椅)可以包含下面的重量份(pbw)的组分：
| 软质发泡体配制物 | pbw |
| 多元醇 | 20-100 |
| 表面活性剂 | 0.3-3 |
| 发泡剂 | 1-6 |
| 交联剂 | 0-3 |
| 酸封闭的吡咯烷催化剂 | 0.2-2.5 |
| 异氰酸酯指数 | 70-115 |
通用的含有式(1)或(2)的酸封闭的吡咯烷催化剂的密度为15至70kg/m3的硬质聚氨酯发泡体配制物的一个非限定性例子可以包含下面的重量份的组分(pbw)：
| 硬质发泡体配制物 | pbw |
| 多元醇 | 100 |
| 表面活性剂 | 1-3 |
| 发泡剂 | 20-40 |
| 水 | 0-3 |
| 酸封闭的吡咯烷催化剂 | 0.5-3 |
| 硬脂酸酯指数 | 80-400 |
对于含有异氰酸酯官能团的化合物的量没有限制，但是通常将处于本领域技术人员已知的那些范围内。上面给出的一个示例性范围是涉及异氰酸酯指数来表示的，其定义为异氰酸酯当量数除以活性氢当量总数，乘以100。
因此，在又一实施方案中，本发明提供一种生产聚氨酯材料的方法，其包括将含有异氰酸酯官能团的化合物，含活性氢的化合物，卤化烯烃和任选的辅助组分在根据本发明的酸封闭的吡咯烷催化剂存在下接触。
在一个具体实施方案中，聚氨酯材料是硬质或软质发泡体，其通过将至少一种多元醇和至少一种多异氰酸酯在式(1)和/或(2)的酸封闭的吡咯烷催化剂和卤化烯烃化合物存在下组合在一起来形成反应混合物和将该反应混合物经历足以引起该多元醇与该多异氰酸酯反应的条件来制备。多元醇，多异氰酸酯，酸封闭的吡咯烷催化剂和卤化烯烃化合物可以在将它们混合和形成反应混合物之前进行加热。在其他实施方案中，多元醇，多异氰酸酯，酸封闭的吡咯烷催化剂和卤化烯烃化合物在环境温度(例如约15℃至40℃)混合，并且可以将热施加到该反应混合物，但是在一些实施方案中施加热会是不必需的。聚氨酯发泡体可以在自由增长(块状)方法中制造，其中该发泡体在最小或没有垂直约束下自由增长。可选地，模制的发泡体可以通过将反应混合物引入到封闭模具中，并且使它在该模具中发泡来制造。具体的多元醇和多异氰酸酯根据形成的发泡体的期望特性来选择。可用于制造聚氨酯发泡体的其他辅助组分例如上述那些也可以包括来生产具体类型的发泡体。
根据另一实施方案，聚氨酯材料可以在一步法中生产，其中A侧反应物与B侧反应物反应。A侧反应物可以包含多异氰酸酯，而B侧反应物可以包含多元醇，酸封闭的吡咯烷催化剂和卤化烯烃化合物。在一些实施方案中，A侧和/或B侧还可以任选地含有其他辅助组分例如上述那些。
生产的聚氨酯材料可以用于多种应用，例如预涂层；地毯衬背材料；建筑复合材料；绝缘体；喷雾发泡绝缘体；需要使用冲击混合喷枪的应用；氨酯/脲杂合弹性体；车辆内部件和外部件例如床衬垫，挡泥板，门板和方向盘；软质发泡体(例如家具发泡体和车辆部件发泡体)；连皮发泡体；硬质喷雾发泡体；硬质现浇发泡体；涂料；粘结剂，密封剂；长丝缠绕；和其他聚氨酯复合材料，发泡体，弹性体，树脂和反应注塑(RIM)应用。
现在将参考下面的非限定性实施例来进一步描述本发明。
实施例
实施例1
聚氨酯发泡体由MDI和多元醇树脂共混物(如表1所示)制造，其中该多元醇树脂共混物中的催化剂选自不同的现有技术的胺催化剂(
ZF-10，ZF-20，Z-110，Z-130，ZR-70，如前所述，其已经与戊二酸或甲酸混合)或本文所述的本发明的酸封闭的吡咯烷催化剂的一个例子(“XP CAT”)，其用式1和2的催化剂的混合物表示，并且两个式的x＝4。在XP CAT的一个样品中，A(如式1和2所示)是甲酸的离子。在XP CAT的第二样品中，A(如式1和2所示)是戊二酸的离子。
表1
如所示的，表1显示了多元醇树脂共混物的组分。
649多元醇是一种改性的芳族聚酯多元醇。
R-425-X聚醚多元醇是一种胺基聚醚多元醇。
SG-522多元醇是一种蔗糖基多元醇。
聚醚多元醇产品和
芳族聚酯多元醇产品商购自Huntsman Corporation(美国德克萨斯州伍德兰兹)。阻燃剂A是四溴邻苯二甲酸酯二醇，其作为PHT4-DiolTM反应性卤化阻燃剂商购自LANXESS AG(德国科隆)。阻燃剂B是一种氯化磷酸酯。所用硅酮表面活性剂是
DC-193硅酮表面活性剂，其商购自Evonik Industries AG(德国埃森)。所用发泡剂是卤化烯烃发泡剂，由Honeywell Corporation以名称
LBA发泡剂来生产。
依照程序例如ASTM D 7487-18，发泡体在杯中使用50g多元醇树脂共混物和50g的MDI强力混合4秒，然后使用秒表测量发泡曲线。发泡体在它们形成时的“消粘时间”在初始时和在存储6周后测量，作为体系稳定性的指示，其结果在图1中给出。不稳定的多元醇共混物将固有地生产具有较慢的消粘时间的发泡体，因为发泡剂和/或催化剂通过一起反应而失活。如从图1中明显的，含有本发明的酸封闭的吡咯烷催化剂(“XP CAT”)的共混物比现有技术的催化剂和甲酸或戊二酸的混合物明显更稳定。这是出人意料的，因为XP CAT的吡咯烷基氮具有与常规催化剂的氨基甲基部分类似或更高的pKa(表2)，并且具有更高的pKa值的胺预期具有与卤化烯烃发泡剂更大的反应性。实际上，给定吡咯烷基的高亲核性(其已经由Mayr等人实验测量(J.Org.Chem.2007,72,3679-3688))，完全出人意料的是这些本发明的具有卤化烯烃发泡剂的组合物比它们的线性烷基氨基类似物更稳定。
表2
1使用Advanced Chemistry Development(ACD/Labs)软件V11.02(
1994-2019ACD/Labs)计算
2 CRC Handbook of Chemistry and Physics
3 US9051442
4 J.Org.Chem.1961,26,3,779-782
5 J.Chem.Eng.Data 2016,61,247-254
实施例2
当与通常用于聚氨酯喷雾发泡体的金属助催化剂一起存储时，许多酸封闭的胺催化剂在卤化烯烃发泡剂存在下不相容，通常在多元醇树脂共混物中形成固体沉淀物和抑制发泡体反应性。使用表1的配制物来评价聚氨酯发泡体，其中表1中的催化剂包含XP CAT和甲酸，具有和不具有铋助催化剂。依照例如ASTM D 7487-18的程序，在共混这样的配制物(具有和不具有铋)之后立即和在这样的配制物在50℃老化了6周后(二者具有和不具有铋)再次测量生产的聚氨酯发泡体的乳白期和线凝胶(string gel)时间。在具有铋的体系中，来自于Shepherd chemical的
8842的使用量是0.5wt％，基于表1的配制物的总重量计。
乳白期和线凝胶时间测量依照例如ASTM D 7487-18的程序来进行。
图2显示了具有和不具有铋时，聚氨酯发泡体的稳定性良好，在配制物在50℃老化6周后反应性仅具有小的漂移。
实施例3
使用与实施例1相同的程序，与作为式1和2中的“A”的不同的酸(即甲酸，2-乙基己酸，戊二酸，柠檬酸和苹果酸)相组合的XP CAT存储稳定性通过在制备XP CAT和酸(如表1所示)的多元醇共混物后不久以及该多元醇共混物在50℃老化6周后，测量使用该多元醇共混物制备的聚氨酯配制物的乳白期和线凝胶的变化来评价。如图3中可见，在50℃存储6周后漂移(即乳白期和线凝胶的变化率)不大于60％。这证实了本发明要求保护的酸封闭的催化剂作为聚氨酯催化剂用于使用卤化烯烃发泡剂的体系的出人意料的优异的稳定性。
实施例4
使用与实施例1相同的程序，与不同的酸(即甲酸，乳酸，2-乙基己酸，丙酸和乙酸)相组合的对比催化剂
LE-30的存储稳定性通过在制备XP CAT和酸作为催化剂(如表1所示)的多元醇共混物后不久以及该多元醇共混物在50℃老化6周后，测量使用该多元醇共混物制备的聚氨酯配制物的乳白期和线凝胶的变化来评价。如图3中可见，在50℃存储6周后漂移高达260％。这进一步证实了与现有技术的催化剂相比，本发明要求保护的酸封闭的催化剂作为使用卤化烯烃发泡剂的体系的聚氨酯催化剂的出人意料的优异的稳定性。
Claims (11)
1.聚氨酯配制物，其包含：(i)式(1)和/或式(2)中至少一个所示的酸封闭的吡咯烷催化剂：
其中x是1-10的整数和A是酸性化合物的离子，其中该酸性化合物具有式(OH)n-R-(COOH)m，其中R是氢、烷基、烯基、脂环族的、芳族的或烷基芳族的基团，n和m是0-3的整数，条件是n+m≥1，并且当n＝1和m＝0时，R是芳族的或烷基芳族的；(ii)含有异氰酸酯官能团的化合物；(iii)含活性氢的化合物；和(iv)卤化烯烃化合物。
2.根据权利要求1所述的聚氨酯配制物，其中x是1-4的整数。
3.根据权利要求1所述的聚氨酯配制物，其中R是甲基、乙基、正丙基、异丙基、丙基、丁基、异丁基、正戊基、正癸基或2-乙基己基。
4.根据权利要求1所述的聚氨酯配制物，其中该聚氨酯配制物进一步包含含有至少一个叔胺基团的胺催化剂和/或非胺催化剂。
5.聚氨酯配制物，其包含：(i)式(1)和/或式(2)中至少一个所示的酸封闭的吡咯烷催化剂：
其中x是1-10的整数和A是酸性化合物的离子，其中该酸性化合物具有式(OH)n-R-(COOH)m，其中R是氢、烷基、烯基、脂环族的、芳族的或烷基芳族的基团，n和m是0-3的整数，条件是n+m≥1，并且当n＝1和m＝0时，R是芳族的或烷基芳族的；(ii)含有异氰酸酯官能团的化合物；(iii)含活性氢的化合物；(iv)卤化烯烃化合物；和(v)式(3)的吡咯烷催化剂：
6.催化剂包，其包含：(i)式(1)和/或式(2)中至少一个所示的酸封闭的吡咯烷催化剂：
其中x是1-10的整数和A是酸性化合物的离子，其中该酸性化合物具有式(OH)n-R-(COOH)m，其中R是氢、烷基、烯基、脂环族的、芳族的或烷基芳族的基团，n和m是0-3的整数，条件是n+m≥1，并且当n＝1和m＝0时，R是芳族的或烷基芳族的；和
卤化烯烃化合物。
7.根据权利要求6的催化剂包，其进一步包含式(3)的吡咯烷催化剂：
8.生产聚氨酯材料的方法，其包括将含有异氰酸酯官能团的化合物，含活性氢的化合物和任选的辅助组分在式(1)和/或式(2)中至少一个所示的酸封闭的吡咯烷催化剂和卤化烯烃化合物存在下进行接触：
其中x是1-10的整数和A是酸性化合物的离子，其中该酸性化合物具有式(OH)n-R-(COOH)m，其中R是氢、烷基、烯基、脂环族的、芳族的或烷基芳族的基团，n和m是0-3的整数，条件是n+m≥1，并且当n＝1和m＝0时，R是芳族的或烷基芳族的。
9.根据权利要求8所述的方法生产的聚氨酯材料。
10.根据权利要求9所述的聚氨酯材料，其中该聚氨酯材料是硬质发泡体或软质发泡体。
11.根据权利要求8所述的方法生产的聚氨酯材料，其用作预涂层，地毯衬背材料，建筑复合材料，绝缘体，喷雾发泡绝缘体，氨酯/脲杂合弹性体；车辆内部件和外部件，软质发泡体，连皮发泡体，硬质喷雾发泡体，硬质现浇发泡体；涂料；粘结剂，密封剂或长丝缠绕。
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