CN108017786A - 利用二苯酮四酸二酐制备聚酰亚胺薄膜的方法 - Google Patents

利用二苯酮四酸二酐制备聚酰亚胺薄膜的方法 Download PDF

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CN108017786A
CN108017786A CN201711413756.9A CN201711413756A CN108017786A CN 108017786 A CN108017786 A CN 108017786A CN 201711413756 A CN201711413756 A CN 201711413756A CN 108017786 A CN108017786 A CN 108017786A
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kapton
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徐旭
黄孝华
李裕琪
陆绍荣
韦春
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Guilin University of Technology
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Abstract

本发明公开了一种利用二苯酮四酸二酐制备聚酰亚胺薄膜的方法。利用3,4‑二氟苯甲醛、对硝基苯乙酮、乙酸铵和乙酸制得二硝基单体4‑(3,4‑二氟苯基)‑2,6双(4‑硝基苯基)吡啶，再加入水合肼反应制得二胺单体4‑(3,4‑二氟苯基)‑2,6双(4‑氨基苯基)吡啶，再与二苯酮四酸二酐反应制得前驱体聚酰胺酸（PAA）溶液，在模具上流延成膜，然后将模具放在80 ℃的烘箱里过夜，之后放入马弗炉中进行热亚胺化反应，最后制得聚酰亚胺薄膜。本发明方法操作简单，易于大规模推广应用，且制得的聚酰亚胺聚酰亚胺薄膜具有优异的耐热性、耐溶剂性、疏水性以及良好的拉伸性能和一定的形状记忆性能，在军工方面、航天航空方面有一定的应用前景。

Description

利用二苯酮四酸二酐制备聚酰亚胺薄膜的方法
技术领域
本发明属于智能复合材料技术领域，特别涉及一种利用二苯酮四酸二酐制备聚酰亚胺薄膜的方法。
背景技术
随着社会科学的发展，人类在太空领域的探索中对大型构建提出更高的要求，航天器的一些大型结构部件，由于受到尺寸限制，所以需要在发射前进行折叠，当升入太空后在一定条件下恢复其原始形状，形状记忆聚合物由于独特的形状记忆机理和性能，成为最具前途的材料之一。目前SMP在航天飞行器方面的主要的应用包括太阳能电池阵、天线、衔架等复杂结构部件中。然而，大多数航天器运行在低地球轨道中，它的环境温度在-160~+120 ℃之间，但是目前常用SMP的Tg主要集中在低温和中等温度(-10~+120 ℃)。研究表明，要使一个高分子能长期应用，其Tg通常需要比环境温度高50 ℃以上。因此，需要开发高Tg的新型SMP。
聚酰亚胺是指其主链结构单元中含有酰亚胺特征基团的芳杂环聚合物，因其分子主链中含酰亚胺环和苯环平面共轭的刚性结构，使得聚酰亚胺拥有一些优于大多数聚合物的优秀性能，如超强的耐高温性、低热膨胀系数、低介电常数以及良好的机械性能己被广泛应用于航空航天、电气、汽车、微电子等领域。由化学交联而得到的热固性聚酰亚胺还具有很强得结构稳定、不易蠕变等特性，可在恶劣的环境下长期使用。形状记忆聚酰亚胺由于其突出的热稳定性、良好的力学性能等弥补了传统形状记忆聚合物的不足，有望作为大型结构部件的基体材料而应用在航天航空等领域。
虽然聚酰亚胺是一种具有代表性的综合性能优异的聚合物，但是大多数芳香族聚酰亚胺分子链刚性很强，导致很难对其进行加工，从而限制了它们在某些特殊领域的应用。常规聚酰亚胺已经满足不了人们的要求，开发新型高性能的聚酰亚胺已经成为当今科研者的目标。为解决上述缺点，科研者们做了很多研究。结构改性是改善聚酰亚胺性能的一种有效的方法，在聚酰亚胺的分子主链上引入特殊基团，如柔性基团、大取代基、非共平面结构，不对称结构，如：-O-、-S-、-CH2-、-SO2-、含氟基团、脂肪族基团等。
在本申请中，我们通过分子设计在聚酰亚胺的主链中引入含氟基团及吡啶环，提高聚合物的耐溶解性能并维持其机械性能、热稳定性，制得新型热固性含氟聚酰亚胺聚合物，使其除具备普通树脂良好的性能之外还兼具一定的形状记忆效应，本思路未见文献报道。
发明内容
本发明的目的是提供一种利用二苯酮四酸二酐制备聚酰亚胺薄膜的方法。
具体步骤为：
(1) 在一个配有磁力搅拌、回流冷凝管及氮气入口的500 mL三口烧瓶中，依次加入3,4-二氟苯甲醛（15.00 g，n=0.11 mol）、对硝基苯乙酮（34.86 g，n=0.21 mol）、乙酸铵（97.63 g，n=1.27 mol）和乙酸（200 mL），开动磁力搅拌，通入N2半小时后，加热至125 ℃保持12 h，待反应结束后将得到的混合物抽滤，得到淡黄色固体，放入真空干燥箱120 ℃下干燥12 h，将得到的产物用DMF重结晶，得到针状晶体，即为二硝基单体4-(3,4-二氟苯基)-2,6双(4-硝基苯基)吡啶，简称FPNP。
(2) 在一个配有磁力搅拌、回流冷凝管、恒压滴液漏斗和氮气进出口的500 mL三口烧瓶中，依次加入步骤(1)制得的二硝基单体4-(3,4-二氟苯基)-2,6双(4-硝基苯基)吡啶（8.00 g，n=18.46 mmol）、Pd/C（2.00 g）和乙醇（152 mL），开通磁力搅拌，通入氮气半小时后加热至85 ℃，回流，待温度稳定在85 ℃时候开始滴加水合肼45 mL，水合肼1 h滴完，继续搅拌回流8 h后停止反应，再加入过量的四氢呋喃并趁热过滤，除掉Pd/C，得到澄清淡黄的溶液，使用旋转蒸发仪减压蒸馏，除去乙醇和未反应的水合肼，得到淡黄色的固体于真空干燥箱120 ℃干燥过夜，再将得到的粗产物用乙醇重结晶，得到淡黄色固体即为二胺单体4-(3,4-二氟苯基)-2,6双(4-氨基苯基)吡啶，简称FPAP。
(3) 在一个具有氮气进出口和磁力搅拌的50 mL的两口瓶中加入步骤(2)制得的二胺单体4-(3,4-二氟苯基)-2,6双(4-氨基苯基)吡啶（0.6500 g，1.741 mmol）和NMP（4.68g），在氮气保护下搅拌1 h，然后加入二苯酮四酸二酐（0.5610 g，1.741 mmol）冰浴4 h后，在室温下搅拌24 h，得到黏稠的前驱体聚酰胺酸（PAA）溶液用NMP溶剂配制固含量为8 wt.%的PAA溶液，在模具上流延成膜，然后将模具放在80 ℃的烘箱里过夜，之后放入马弗炉中进行热亚胺化，程序升温120 ℃、150 ℃、180 ℃、200 ℃、250 ℃和300 ℃各1 h，待降至室温后，将模具放入蒸馏水中脱模烘干，最后制得聚酰亚胺薄膜。
本发明方法操作简单，易于大规模推广应用，且制得的聚酰亚胺聚酰亚胺薄膜具有优异的耐热性、耐溶剂性、疏水性以及良好的拉伸性能和一定的形状记忆性能，在军工方面、航天航空方面有一定的应用前景。
附图说明
图1为本发明实施例中制得的二硝基单体4-(3,4-二氟苯基)-2,6双(4-硝基苯基)吡啶的FT-IR谱图。
图2为本发明实施例中制得的二胺单体4-(3,4-二氟苯基)-2,6双(4-氨基苯基)吡啶的FT-IR谱图。
图3为本发明实施例中制得的二胺单体4-(3,4-二氟苯基)-2,6双(4-氨基苯基)吡啶的1H-NMR(a)和13C-NMR(b)图谱(DMSO-d6)。
图4为本发明实施例中制得的聚酰亚胺薄膜上液滴的轮廓对比照片。
具体实施方式
实施例：
(1) 在一个配有磁力搅拌、回流冷凝管及氮气入口的500 mL三口烧瓶中，依次加入3,4-二氟苯甲醛（15.00 g，n=0.11 mol）、对硝基苯乙酮（34.86 g，n=0.21 mol）、乙酸铵（97.63 g，n=1.27 mol）和乙酸（200 mL），开动磁力搅拌，通入N2半小时后，加热至125 ℃保持12 h，待反应结束后将得到的混合物抽滤，得到淡黄色固体，放入真空干燥箱120 ℃下干燥12 h，将得到的产物用DMF重结晶，得到针状晶体，即为二硝基单体4-(3,4-二氟苯基)-2,6双(4-硝基苯基)吡啶，简称FPNP。
(2) 在一个配有磁力搅拌、回流冷凝管、恒压滴液漏斗和氮气进出口的500 mL三口烧瓶中，依次加入步骤(1)制得的二硝基单体4-(3,4-二氟苯基)-2,6双(4-硝基苯基)吡啶（8.00 g，n=18.46 mmol）、Pd/C（2.00 g）和乙醇（152 mL），开通磁力搅拌，通入氮气半小时后加热至85 ℃，回流，待温度稳定在85 ℃时候开始滴加水合肼45 mL，水合肼1 h滴完，继续搅拌回流8 h后停止反应，再加入过量的四氢呋喃并趁热过滤，除掉Pd/C，得到澄清淡黄的溶液，使用旋转蒸发仪减压蒸馏，除去乙醇和未反应的水合肼，得到淡黄色的固体于真空干燥箱120 ℃干燥过夜，再将得到的粗产物用乙醇重结晶，得到淡黄色固体即为二胺单体4-(3,4-二氟苯基)-2,6双(4-氨基苯基)吡啶，简称FPAP。
(3) 在一个具有氮气进出口和磁力搅拌的50 mL的两口瓶中加入步骤(2)制得的二胺单体4-(3,4-二氟苯基)-2,6双(4-氨基苯基)吡啶（0.6500 g，1.741 mmol）和NMP（4.68g），在氮气保护下搅拌1 h，然后加入二苯酮四酸二酐（0.5610 g，1.741 mmol）冰浴4 h后，在室温下搅拌24 h，得到黏稠的前驱体聚酰胺酸（PAA）溶液用NMP溶剂配制固含量为8 wt.%的PAA溶液，在模具上流延成膜，然后将模具放在80 ℃的烘箱里过夜，之后放入马弗炉中进行热亚胺化，程序升温120 ℃、150 ℃、180 ℃、200 ℃、250 ℃和300 ℃各1 h，待降至室温后，将模具放入蒸馏水中脱模烘干，最后制得聚酰亚胺薄膜。
将本实施例制得的聚酰亚胺薄膜进行性能表征，发现其玻璃化转变温度为346℃，T5%热失重温度为575 ℃，T10%热失重温度为602 ℃，Td为564 ℃，800 ℃下的残炭率为70%，表现出优异的耐热性；同时，在常规有机溶剂中都不溶，具有很好的耐溶剂性；另外，接触角为93.6°，表现出优异的疏水性；最后，具有良好的拉伸性能和一定的形状记忆性能，其拉伸强度和断裂伸长率分别为80 MPa和8.8％，形状固定率和形状回复率达到66.11%和69.75%。

Claims (1)

1.一种利用二苯酮四酸二酐制备聚酰亚胺薄膜的方法，其特征在于具体步骤为：
(1) 在一个配有磁力搅拌、回流冷凝管及氮气入口的500 mL三口烧瓶中，依次加入0.11 mol 3,4-二氟苯甲醛、0.21 mol对硝基苯乙酮、1.27 mol乙酸铵和200 mL乙酸，开动磁力搅拌，通入N2半小时后，加热至125 ℃保持12 h，待反应结束后将得到的混合物抽滤，得到淡黄色固体，放入真空干燥箱120 ℃下干燥12 h，将得到的产物用DMF重结晶，得到针状晶体，即为二硝基单体4-(3,4-二氟苯基)-2,6双(4-硝基苯基)吡啶；
(2) 在一个配有磁力搅拌、回流冷凝管、恒压滴液漏斗和氮气进出口的500 mL三口烧瓶中，依次加入18.46 mmol步骤(1)制得的二硝基单体4-(3,4-二氟苯基)-2,6双(4-硝基苯基)吡啶、2.00 g Pd/C和152 mL乙醇，开通磁力搅拌，通入氮气半小时后加热至85 ℃，回流，待温度稳定在85 ℃时候开始滴加水合肼45 mL，水合肼1 h滴完，继续搅拌回流8 h后停止反应，再加入过量的四氢呋喃并趁热过滤，除掉Pd/C，得到澄清淡黄的溶液，使用旋转蒸发仪减压蒸馏，除去乙醇和未反应的水合肼，得到淡黄色的固体于真空干燥箱120 ℃干燥过夜，再将得到的粗产物用乙醇重结晶，得到淡黄色固体即为二胺单体4-(3,4-二氟苯基)-2,6双(4-氨基苯基)吡啶；
(3) 在一个具有氮气进出口和磁力搅拌的50 mL的两口瓶中加入1.741 mmol步骤(2)制得的二胺单体4-(3,4-二氟苯基)-2,6双(4-氨基苯基)吡啶和4.68 g NMP，在氮气保护下搅拌1 h，然后加入1.741 mmol二苯酮四酸二酐冰浴4 h后，在室温下搅拌24 h，得到黏稠的前驱体聚酰胺酸溶液用NMP溶剂配制固含量为8 wt.% 的前驱体聚酰胺酸溶液，在模具上流延成膜，然后将模具放在80 ℃的烘箱里过夜，之后放入马弗炉中进行热亚胺化，程序升温120 ℃、150 ℃、180 ℃、200 ℃、250 ℃和300 ℃各1 h，待降至室温后，将模具放入蒸馏水中脱模烘干，最后制得聚酰亚胺薄膜。
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113549234A (zh) * 2021-07-22 2021-10-26 江苏传艺科技股份有限公司 一种疏水性聚酰亚胺薄膜的生产工艺

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1048551A (zh) * 1989-06-22 1991-01-16 沃纳-兰伯特公司 含结构被破坏淀粉的聚合物基混合组合物
CN101402795A (zh) * 2008-11-19 2009-04-08 北京航空航天大学 一种新型耐高温聚酰亚胺泡沫及其制备方法
CN101451013A (zh) * 2007-11-29 2009-06-10 比亚迪股份有限公司 一种聚酰亚胺材料及其制备方法
CN101560298A (zh) * 2009-05-26 2009-10-21 东华大学 热塑性含氟全芳型聚酰亚胺粉末及其制备方法
CN101663347A (zh) * 2007-04-03 2010-03-03 Solpit工业株式会社 可溶于溶剂的6,6-聚酰亚胺共聚物及其制造方法
CN101787129A (zh) * 2010-03-04 2010-07-28 南京航空航天大学 可溶性耐高温芳香族聚酰亚胺及其制备方法
CN101812232A (zh) * 2010-04-09 2010-08-25 北京航空航天大学 一种聚酰亚胺泡沫塑料及其制备方法
CN102093714A (zh) * 2010-12-22 2011-06-15 北京航空航天大学 一种轻质柔性聚酰亚胺泡沫材料及其制备方法

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1048551A (zh) * 1989-06-22 1991-01-16 沃纳-兰伯特公司 含结构被破坏淀粉的聚合物基混合组合物
CN101663347A (zh) * 2007-04-03 2010-03-03 Solpit工业株式会社 可溶于溶剂的6,6-聚酰亚胺共聚物及其制造方法
CN101451013A (zh) * 2007-11-29 2009-06-10 比亚迪股份有限公司 一种聚酰亚胺材料及其制备方法
CN101402795A (zh) * 2008-11-19 2009-04-08 北京航空航天大学 一种新型耐高温聚酰亚胺泡沫及其制备方法
CN101560298A (zh) * 2009-05-26 2009-10-21 东华大学 热塑性含氟全芳型聚酰亚胺粉末及其制备方法
CN101787129A (zh) * 2010-03-04 2010-07-28 南京航空航天大学 可溶性耐高温芳香族聚酰亚胺及其制备方法
CN101812232A (zh) * 2010-04-09 2010-08-25 北京航空航天大学 一种聚酰亚胺泡沫塑料及其制备方法
CN102093714A (zh) * 2010-12-22 2011-06-15 北京航空航天大学 一种轻质柔性聚酰亚胺泡沫材料及其制备方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
XU XU等: "《High Glass Transition of Fluorinated Polyimides Derived from 4-(3,4-Difluorophenyl)-2,6-bis(4-aminophenyl)pyridine》", 《CHINESE JOURNAL OF CHEMISTRY》 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113549234A (zh) * 2021-07-22 2021-10-26 江苏传艺科技股份有限公司 一种疏水性聚酰亚胺薄膜的生产工艺
CN113549234B (zh) * 2021-07-22 2023-05-16 江苏传艺科技股份有限公司 一种疏水性聚酰亚胺薄膜的生产工艺

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