CN101007778A - 一种链延长型芴基双马来酰亚胺及其制备方法 - Google Patents

一种链延长型芴基双马来酰亚胺及其制备方法 Download PDF

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CN101007778A
CN101007778A CN 200710036307 CN200710036307A CN101007778A CN 101007778 A CN101007778 A CN 101007778A CN 200710036307 CN200710036307 CN 200710036307 CN 200710036307 A CN200710036307 A CN 200710036307A CN 101007778 A CN101007778 A CN 101007778A
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胡志强
李善君
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Fudan University
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Abstract

本发明属高分材料技术领域，具体为一种新结构的链延长型芴基双马来酰亚胺及其制备方法。具体过程为：在低温，惰性气体保护下，9，9－双(4－氨基苯基)芴溶解于N，N－二甲基乙酰胺等非质子极性溶剂中，搅拌下滴加等摩尔马来酸酐的N，N－二甲基乙酰胺溶液，滴加完毕反应2小时左右，直接加入等摩尔的二酐，继续搅拌反应3小时左右，加入醋酐及醋酸钾的混合物，室温搅拌，反应4小时左右，水中沉淀得到链延长型芴基双马来酰亚胺，收率超过95％。合成的产物在保持双马来酰亚胺的特性的同时，大幅度提高了溶解性及加工性能。

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一种链延长型芴基双马来酰亚胺及其制备方法
技术领域
本发明属高分子材料技术领域，具体涉及一种链延长型芴基双马来酰亚胺及其制备方法。
背景技术
双马来酰亚胺树脂拥有优异的热稳定性、高的拉伸强度和模量，优异的耐化学腐蚀性以及耐湿热性，从而作为高性能热固性树脂广泛用作先进复合材料基体树脂。而由9，9-双(4-氨基苯基)芴合成的双马来酰亚胺单体9，9-双(4-马来酰亚胺基苯基)芴(见结构式(A))具有诸多优异的性能，如优异的耐热性，高的残碳率，高的极限氧指数(LOI)以及好的阻燃性等而引起人们重视。但是，该单体具有非常高的熔点，其熔点超过300℃；而且其在大部分的有机溶剂中均有很差的溶解性，因而对于其双马来酰亚胺的合成及加工都非常困难，尤其是它在粘合剂与复合材料中的应用。
Figure A20071003630700031
9，9-双(4-马来酰亚胺基苯基)芴结构式
对于链延长型芴基双马来酰亚胺的合成，目前仅有文献Journal of Polymer Science：PartA：Polymer Chemistry edition，1982，20有过报道，且其仅提及了含3，3’，4’4’-二苯甲酮四酸二酐结构的链延长芴基双马来酰亚胺，并未详细讨论其合成以及溶解性等，更未提及其它结构的链延长型芴基双马来酰亚胺。
发明内容
本发明的目的在于提供一种溶解性和加工性好、耐热性能优良的链延长型芴基双马来酰亚胺及其制备方法。
本发明提供的链长型芴基双马来酰亚胺，其结构式如下：
其中，Ar代表芳香族或脂肪族二酐。Ar具体可以是3，3’，4’4’-氧撑邻苯四甲酸二酐(ODPA)、3，3’，4’4’-二苯甲酮四酸二酐(BTDA)，双酚A型二酐(BPADA)、均苯四甲酸二酐(PMDA)、3，3’，4，4’-联苯四甲酸二酐(BPDA)等，也可以是其他芳香族或脂肪族二酐。
本发明提出的链长型芴基双马来酰亚胺合成路线如下：
链延长型芴基双马来酰亚胺的合成路线
本发明的制备步骤为：在低温，惰性气体保护下，将9，9-双(4-氨基苯基)芴溶解于非质子极性溶剂(如N，N-二甲基乙酰胺(DMAc)等)中，搅拌下滴加等摩尔马来酸酐的同样非质子极性溶剂的溶液，滴加完毕，反应2.5-3.5小时，然后直接加入等摩尔的芳香族或脂肪族二酐，继续搅拌反应2.5-3.5小时，最后加入醋酐及醋酸钾的混合物，室温搅拌50-70分钟，55-65℃反应3-5小时，水中沉淀即得到链延长型芴基双马来酰亚胺。
在此过程中，低温范围可以是-20℃～+20℃之间，非质子极性溶剂还可以是N，N-二甲基酰胺或N-甲基吡咯烷酮等。
采用本发明制得的链延长型芴基双马来酰亚胺收率超过95％％。经红外图谱、元素分析和核磁共振光谱分析产品结构得到确认。结果见表1：
表1链延长型芴基双马来酰亚胺的结构表征
样品 分子式 FTIR(KBr)   1H-NMR(DMSO-d6) 元素分析 外观
I C33H20N2O4 1770，1707，1378cm-1(亚胺结构)，1605cm-1(烯键) 7.16(4H，烯烃质子)7.24-7.98(16H，芳烃质子)    计算值：C，77.94；H，3.96；N，5.51测量值：6.83；H，4.15；N，5.42 亮黄
II C74H42N4O9 1777，1716，1371cm-1(亚胺结构)，1605cm-1(烯键) 7.16(4H，烯烃质子)7.25-7.98(38H，芳烃质子)    计算值：C，78.57；H，3.74；N，4.95；测量值：C，77.08；H，3.74；N，4.65； 黄
III C75H42N4O9 1778，1716，1372cm-1(亚胺结构)1618cm-1(烯键) 7.16(4H，烯烃质子)7.24-8.16(38H，芳烃质子)    计算值：C，78.80；H，3.70；N，4.90；测量值：C，74.38；H，3.65；N，4.35； 黄
IV C89H56N4O10 1777，1716，1370cm-1(亚胺结构)1612cm-1(烯键) 1.69(6H，CH3)7.10(4H，烯烃质子)7.11-7.98(38H，芳烃质子)    计算值：C，79.69；H，4.21；N，4.18；测量值：C，78.01；H，3.74；N，4.18； 黄
其中：(I)(II)(III)(IV)的结构式如下：
Figure A20071003630700061
所有的链延长型芴基双马来酰亚胺与9，9-双(4-马来酰亚胺基苯基)芴相比，溶解性有大幅的提高(见表2)。
表2链延长型芴基双马来酰亚胺的溶解性
  样品    NMP     DMAc    CHCl3   CH2Cl2   DMSO    THF   Acetone
  I    Ins     Ins    Ins   Ins   S    Ins   Ins
  II    S     S    S   S   S    S   Ins
  III    S     S    S   S   S    S   Ins
  IV    S     S    S   S   S    S   Ins
a.S，室温溶解；Ins，不溶；
具体实施方式
为了更好地实施本发明，特举例说明之，但不是对本发明的限制。
实施例1
17.4g(0.05mol)9，9-双(4-氨基苯基)芴溶解于120ml N，N-二甲基乙酰胺(DMAc)中，冰浴冷却至0℃，不断搅拌下滴加等摩尔马来酸酐的N，N-二甲基乙酰胺溶液，滴加完毕反应3小时后，直接加入等摩尔的3，3’，4’4’-氧撑邻苯四甲酸二酐(ODPA)，继续搅拌反应3小时后，加入醋酐及醋酸钾的混合物，室温搅拌1小时，60℃反应4小时，水中沉淀得到醚酐链延长型芴基双马来酰亚胺。
实施例2
除使用0.05mol 3，3’，4’4’-二苯甲酮四酸二酐外，其他配方操作步骤和结果和实施例1完全一样，得到酮酐链延长型芴基双马来酰亚胺。
实施例3
除使用0.05mol双酚A二酐外，其他配方操作步骤和结果和实施例1完全一样，得到双酚A二酐链延长型芴基双马来酰亚胺。
以上得到的芴基双马来酰亚胺经热环化均聚后的热重分析结果如表3及图4所示，可见链延长型芴基双马来酰亚胺的固化后的树脂热稳定性要好于未链延长的单体9，9-双(4-马来酰亚胺基苯基)芴的固化树脂。因此，链延长型芴基双马来酰亚胺能提高加工性能而同时保持热稳定性能，树脂可以用于各种预浸料、复合材料和粘合剂的添加组分，提高材料的耐热性。
表3固化的链延长型芴基双马来酰亚胺热失重分析结果
固化样品    Tid(℃)    T5(℃)   Tmax(℃)    Yc(％)
    PI     439     453    574     60
    PII     455     484    596     58
    PIII     478     500    598     65
    PIV     477     485    541     57
Tid＝外推得到的起始分解温度
T5＝失重5％的温度
Tmax＝最大分解温度
Yc＝800℃.残碳率

Claims (4)

1、一种链延长型芴基双马来酰亚胺，其特征在于具有如下结构式：
Figure A2007100363070002C1
其中，Ar代表芳香族或脂肪族二酐。
2、根据权利要求1所述的链延长型芴基双马来酰亚胺，其特征在于所述Ar为3，3’，4’4’-氧撑邻苯四甲酸二酐、3，3’，4’4’-二苯甲酮四甲酸二酐、双酚A型二酐、均苯四甲酸二酐、3，3’，4，4’-联苯四甲酸二酐。
3、一种如权利要求1所述的链延长型芴基双马来酰亚胺的制备方法，其特征在于具体步骤如下：在-20℃-20℃范围内，惰性气体保护下，将9，9-双(4-氨基苯基)芴溶解于非质子极性溶剂中，搅拌下滴加等摩尔马来酸酐的非质子极性溶剂溶液；滴加完毕，反应2.5-3.5小时，然后直接加入等摩尔的芳香族或脂肪族二酐，继续搅拌反应2.5-3.5小时，最后加入醋酐及醋酸钾的混合物，室温搅拌50-70分钟，55-65℃反应3-5小时，水中沉淀即得到链延长型芴基双马来酰亚胺。
4、根据权利要求3所述的链延长型芴基双马来酰亚胺的制备方法，其特征在于所述溶剂为N，N-二甲基甲酰胺、N，N-二甲基乙酰胺和N-甲基吡咯烷酮中之一种。
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