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CN104144968A - 用于聚酰胺酰亚胺树脂的低毒性溶剂系统和溶剂系统的制备 - Google Patents

用于聚酰胺酰亚胺树脂的低毒性溶剂系统和溶剂系统的制备 Download PDF

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CN104144968A
CN104144968A CN201280061393.6A CN201280061393A CN104144968A CN 104144968 A CN104144968 A CN 104144968A CN 201280061393 A CN201280061393 A CN 201280061393A CN 104144968 A CN104144968 A CN 104144968A
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约翰·思登斯迪克
大卫·诺格
凯瑟琳·穆林斯
梅斯·菲利普斯
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Fujifilm Hunt Chemicals USA Inc
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    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
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    • C08L79/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen or carbon only, not provided for in groups C08L61/00 - C08L77/00
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Abstract

本发明公开了一种用于聚酰胺酰亚胺树脂的制备和应用的低毒性的非质子烷基酰胺溶剂系统，和一种用于在溶剂系统中以带有蒸馏的单一反应制备聚酰胺酰亚胺树脂的有效方法，所述蒸馏允许回收利用中间流。所述溶剂系统可用于聚酰胺酰亚胺树脂的制备或溶解。

Description

用于聚酰胺酰亚胺树脂的低毒性溶剂系统和溶剂系统的制备
优先权
本专利申请要求2011年12月15日递交的标题为“Low Toxicity SolventSystem for Polyamidimide Resins and Solvent System Manufacture”的第61/576,247号的相应临时专利申请的优先权，且以引用的方式并入本文。
技术领域
本发明的实施方式涉及溶剂的领域；更具体地，本发明的实施方式涉及溶剂以及它们在制备聚酰胺酰亚胺中的用途。
背景技术
聚酰胺酰亚胺(PAI)聚合物由于其优异的耐热性和高强度而用于多种高性能的涂料用途。合成以便于制备涂料的形式的聚酰胺酰亚胺聚合物的主要途径是：使二异氰酸酯(通常是4,4’-亚甲基二苯基二异氰酸酯(MDI))与偏苯三酸酐(TMA)反应。在该方法中，PAI聚合物通常在极性非质子溶剂中合成，例如，该极性非质子溶剂包括二甲基甲酰胺、二甲基乙酰胺、N-甲基吡咯烷酮(NMP)、N-乙基吡咯烷酮的N-甲基酰胺化合物。例如，参见第2,421,021号、第3,260,691号、第3,471,444号、第3,518,230号、第3,817,926号、和第3,847,878号的美国专利。在该合成路径中获得的典型的聚合物固体含量是35％至45％，根据涂料应用的最终用途，其可以采用稀释剂进一步稀释。
替选的溶剂(如，四氢呋喃、甲基乙基酮、γ-丁内酯、或二甲亚砜)具有如下缺点：例如，对于用作反应溶剂而言沸点太低、聚合物溶解度低、或存储稳定性差，这些缺点会改变聚合物树脂的应用性能。
第4,950,700号美国专利和第5,095,070号美国专利列举了γ-丁内酯与N-甲基酰胺助溶剂和二羟甲基亚乙基脲作为替代溶剂合成PAI树脂的实例。然而，γ-丁内酯具有使其受制于法规且不适于在配方中一般用途的神经系统属性。二羟甲基亚乙基脲还没有进行广泛的毒理学研究，且含有疑似对环境和健康负面影响的N-甲基酰胺官能团。如在第20100076223A1号美国专利申请公开中所描述的那些新溶剂(例如，3-甲氧基-N，N-二甲基丙酰胺)太贵，或还未充分测试长期毒性。
此外，质子溶剂(如，乳酸乙酯和丙二醇)不适于用作PAI反应介质。
在实际应用中，虽然本领域中已知的这些溶剂对于制备PAI是有用的或对于其他有机合成反应是有效的，但还要认识到其毒性方面的问题。因此，利用具有对健康和安全最小影响的合成方法制备聚酰胺酰亚胺聚合物是一个优势。
发明内容
公开了一种用于制备聚酰胺酰亚胺的方法。在一个实施方式中，该方法包括利用至少一种非质子二烷基酰胺溶剂。
具体实施方式
为了实现更安全的替选方式，特别是不含常用的N-甲基酰胺溶剂的合成途径，替选的更低毒性的溶剂是必要的。乙酰胺受到关注是因为：乙酰胺具有较低的毒性且易于由工业上可利用的二烷基胺制备，以及具有长期的低的慢性毒性。特别地，二烷基酰胺是有用的。低毒性的溶剂N-乙酰基吗啉(NAM)已被发现可适用于制备聚酰胺酰亚胺树脂。本发明的其他有用的、低毒性的溶剂为二乙基乙酰胺(DEAc)、二-n-丙基乙酰胺、N-甲酰基吗啉、二乙酰基哌嗪、N,N-二异丙基乙酰胺(DIPAc)、二-n-丁基乙酰胺(DIBAc)、二-n-丙基乙酰胺(DIPA)、和N-丙酰基吗啉(NPM)。为了实现更低的毒性方法，现已发现，PAI的合成可通过单独地或彼此组合的方式利用本发明的非质子二烷基酰胺溶剂，或借助于提供独特溶剂系统的助溶剂来完成。例如，对于PAI的各种工业应用，会需要使用溶剂的组合，其中，希望得到在特定范围内的粘度。此外，这些溶剂还可充当稀释剂。为了实现这点，二烷基酰胺溶剂的组合可用来获得所期望的粘度。其他优选的可用于合成PAI树脂或用作溶解PAI树脂的稀释剂的具有低毒性的助溶剂为：水、邻二甲苯、三乙胺、二甲基乙醇胺、吗啉、N-甲基吗啉、丙酮、三甲胺、三丙胺、二乙胺、二异丙胺、和己内酰胺。
还已发现，本发明的实施方式的另一优点是：通过在合成方法中利用一种或多种非质子二烷基酰胺，一锅法两步反应是可以的。
此外，由于用于合成PAI树脂的现有技术的溶剂(如N-甲基酰胺)的毒性，故避免这些化合物的使用。
特别地，非质子二烷基酰胺与其他的工艺助溶剂的优选摩尔比为大约19:1至大约1:1。更优选的比例为大约80:20至大约70:30。最优选的比例为大约78:22。
实施例：
实施例1-合成助溶剂系统的方法：向1L的配备有温度计、冷凝器和机械搅拌器的四颈烧瓶中加入200g的二乙胺。在保持低于55℃的温度的同时，加入279.16g的乙酸酐。然后加入250.15g的吗啉。反应被加热至大约130℃，直到乙酸被耗尽(大约8小时)。通过蒸馏水/过量的吗啉来提高转化率。
实施例2(KM-1145)：装入51g的N-乙酰基吗啉(NAM)、0.85g的己内酰胺、19.8g的MDI、15.65g的TMA，然后加热至100℃。溶液在96℃下保持1.5小时。在一整夜后，温度降至70℃，然后加热至130℃，保持1.25小时。粘度太高；加入12.2g的来自实施例1的NAM助溶剂。
固体％＝33.82％，粘度(DVII，23℃)＝63000cps。
实施例3(JES-3-29)：装入1.68g的己内酰胺、31.49g的TMA、39.66g的MDI和102.12g的来自实施例1的NAM助溶剂，然后在1.5小时内加热至110℃。加热至130℃，监测粘度，直到粘度大于2000cps/120℃(约7小时)。冷却至低于80℃，加入来自实施例1的NAM助溶剂，保持搅拌。在保持90℃的温度下，缓慢地加入TEA(三乙胺)。在大于60℃的温度下保持1小时至2小时。加入水以调节至大约28％的固体。加热、保持在85℃，通过TEA和水调节pH值大于8，根据需要以获得均一性。
实施例4(KM277)：250mL的配备有机械搅拌器、冷凝器和氮气鼓泡器的圆底烧瓶被装有：57.6g的N-乙酰基吗啉、18.9g的邻二甲苯、1.3g的己内酰胺、29.7g的亚甲基二苯基二异氰酸酯、和23.5g的偏苯三酸酐。反应被加热至90℃，保持2小时。然后，反应温度被加热至130℃保持5小时，然后，加入14.7g的N-乙酰基吗啉和3.68g的邻二甲苯，反应器被冷却至室温。利用DVII博勒菲(Brookfield)粘度仪，在23℃下，最终粘度为13834cps。
实施例5(MP-2-11)：250mL的配备有机械搅拌器、冷凝器和氮气鼓泡器的圆底烧瓶被装有：49g的N-乙酰基吗啉、18.9g的二乙基乙酰胺、1.3g的邻二甲苯、29.7g的亚甲基二苯基二异氰酸酯、和23.6g的偏苯三酸酐。反应被加热至90℃保持2小时。然后，反应温度加热至130℃保持3小时，然后，加入3.74g的N-乙酰基吗啉，反应器被冷却至60℃。然后，逐滴加入14.7g的丙酮，反应器被冷却至室温。利用DVII博勒菲粘度仪，在23℃下，最终粘度为3076cps。
实施例6(KM38)：500mL的配备有机械搅拌器、冷凝器和氮气鼓泡器的圆底烧瓶被装有：121g的N-乙酰基吗啉、52.9g的亚甲基二苯基二异氰酸酯、和40.92g的偏苯三酸酐。反应被加热至88℃保持3小时。然后，反应温度被加热至120℃，直到淬火粘度达到1680cps(约2.5小时)，然后，加入41.81g的N-甲酰基吗啉和41.81g的邻二甲苯以淬火冷却反应。反应器被冷却至室温。利用DVII博勒菲粘度仪，在23℃下，最终粘度为8573cps。
实施例7(JES-4-21)：50.27g的亚甲基二苯基二异氰酸酯、38.62g的偏苯三酸酐、和206.56g的N-甲酰基吗啉被装入400mL的烧杯中。反应混合物被加热至80℃，直到通过失重逐步生成大约1当量的CO2。然后，反应温度被加热至130℃，直到骤冷粘度达到730cps，然后，加入41.51g的额外的N-甲酰基吗啉，以骤冷反应。反应器被冷却至室温。最终固体含量被分析为26.02％，最终粘度为10264cps(利用DVII博勒菲粘度仪)。
然而，本领域的普通技术人员在阅读前述说明书之后，本发明的多个变更和变型对于本领域的普通技术人员来说将毫无疑问是显而易见的，应该理解，以实例说明的任何示出和描述的具体实施方式不应该视为限制。因此，引用的多个实施方式的细节不旨在限制权利要求书的范围，它们本身仅提到被视为本发明必要技术特征的那些特征。

Claims (14)

1.一种用于制备聚酰胺酰亚胺的方法，包括：利用至少一种非质子二烷基酰胺溶剂。
2.根据权利要求1所述的方法，其中，所述溶剂为N-乙酰基吗啉。
3.根据权利要求1所述的方法，其中，所述溶剂为二乙基乙酰胺。
4.根据权利要求1所述的方法，其中，所述溶剂为二-N-丙基乙酰胺。
5.根据权利要求1所述的方法，其中，所述溶剂为N-甲酰基吗啉。
6.根据权利要求1所述的方法，其中，所述溶剂为二乙酰基哌嗪。
7.根据权利要求1所述的方法，其中，所述溶剂为N,N-二异丙基乙酰胺。
8.根据权利要求1所述的方法，其中，所述溶剂为二-N-丁基乙酰胺。
9.根据权利要求1所述的方法，其中，所述溶剂为二-N-丙基乙酰胺。
10.根据权利要求1所述的方法，其中，所述溶剂为N-丙酰基吗啉。
11.根据权利要求1所述的方法，其中，非质子二烷基酰胺与其他的工艺助溶剂的比例为大约19:1至大约1:1。
12.根据权利要求1所述的方法，其中，非质子二烷基酰胺与其他溶剂的摩尔比为78:22。
13.根据权利要求4所述的方法，其中，所述助溶剂选自水、邻二甲苯、三乙胺、二甲基乙醇胺、吗啉、N-甲基吗啉、丙酮、三甲胺、三丙胺、二乙胺、二异丙胺、和己内酰胺。
14.一种聚酰胺酰亚胺产品，所述聚酰胺酰亚胺产品通过权利要求1至13所述的方法来制备。
CN201280061393.6A 2011-12-15 2012-12-17 用于聚酰胺酰亚胺树脂的低毒性溶剂系统和溶剂系统的制备 Pending CN104144968A (zh)

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CN109312072A (zh) * 2016-06-06 2019-02-05 西莫-戴顿有限责任公司 使用n-甲酰基吗啉:3-甲氧基n,n-二甲基丙酰胺制备聚酰胺-酰亚胺树脂
CN115926163A (zh) * 2022-12-21 2023-04-07 开封夸克新材料有限公司 一种水性聚酰胺酰亚胺树脂分散液及其制备方法

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