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High-purity ptyltetracid dianhydride and synthesis method thereof, and polyimides synthesized on basis of ptyltetracid dianhydride

A technology of pterene tetra-acid dianhydride and synthesis method, which is applied in the direction of organic chemistry, can solve the problems of high loss of dianhydride compounds and the inability to recrystallize and purify dianhydride, so as to reduce the force, improve the glass transition temperature, and rigidity increased effect

Active Publication Date: 2015-11-11
HUAQIAO UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] The second object of the present invention is to provide a high-yield synthesis method of high-purity pterene tetra-acid dianhydride, so as to solve the problem that part of the dianhydride cannot be recrystallized and purified under normal pressure and the problem of high loss of the dianhydride compound purified by sublimation

Method used

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  • High-purity ptyltetracid dianhydride and synthesis method thereof, and polyimides synthesized on basis of ptyltetracid dianhydride
  • High-purity ptyltetracid dianhydride and synthesis method thereof, and polyimides synthesized on basis of ptyltetracid dianhydride
  • High-purity ptyltetracid dianhydride and synthesis method thereof, and polyimides synthesized on basis of ptyltetracid dianhydride

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0075] Example 1: Preparation of high-purity 2,3,6,7-triptycene tetraacid dianhydride (TM1)

[0076] Under the conditions of ice-salt bath and vigorous stirring, in a 250ml three-necked flask with 120ml of o-xylene and 70ml of dichloromethane, add 60g of aluminum trichloride in four times, and keep the system temperature at 0°C during the addition. After the addition, react at room temperature for 0.5 h, and then react in a water bath at 65° C. for 4 h. Afterwards, the mixed reactant was slowly dispersed in 300ml of 5% hydrochloric acid ice-water mixed solution. During the pouring process, vigorous stirring was required. After standing still, suction filtration, the filter cake was washed with anhydrous acetone, dried, and o-xylene was recrystallized to obtain white 20g of flaky 2,3,6,7-tetramethylanthracene solid, with a melting point of 299°C.

[0077] 1 HNMR (400MHz, CDCl3): δ=2.43(s,12H),7.68(s,4H),8.13(s,2H)

[0078] Weigh 2g of 2,3,6,7-tetramethylanthracene into a 500...

Embodiment 2

[0099] Example 2: Preparation of high-purity 13,14,15,16-tetrachloro-2,3,6,7-triptycene tetraacid dianhydride (TM2)

[0100] Under the conditions of ice-salt bath and vigorous stirring, in a 250ml three-neck flask with 120ml of o-xylene and 70ml of dichloromethane, add 73g of aluminum trichloride in four times, and keep the system temperature at -5°C during the addition process. After the addition, react at room temperature for 0.75h, and then react in a water bath at 60°C for 3h. Afterwards, the mixed reactant was slowly dispersed in 300ml of 5% hydrochloric acid ice-water mixed solution. During the pouring process, vigorous stirring was required. After standing still, suction filtration, the filter cake was washed with anhydrous acetone, dried, and o-xylene was recrystallized to obtain white 24g of flaky 2,3,6,7-tetramethylanthracene solid, with a melting point of 299°C.

[0101] 1 HNMR (400MHz, CDCl3): δ=2.43(s,12H),7.68(s,4H),8.13(s,2H)

[0102] Weigh 2g of 2,3,6,7-tetr...

Embodiment 3

[0122] Example 3: Preparation of high-purity 14,15-dimethoxy-2,3,6,7-triptycene tetraacid dianhydride (TM4)

[0123] Under the conditions of ice-salt bath and vigorous stirring, in a 250ml three-neck flask with 120ml of o-xylene and 70ml of dichloromethane, add 50g of aluminum trichloride in four times, and keep the system temperature at 5°C during the addition process. After the addition, react at room temperature for 1.0 h, and then react in a water bath at 70° C. for 5 h. Afterwards, the mixed reactant was slowly dispersed in 300ml of 5% hydrochloric acid ice-water mixed solution. During the pouring process, vigorous stirring was required. After standing still, suction filtration, the filter cake was washed with anhydrous acetone, dried, and o-xylene was recrystallized to obtain white 19g of flaky 2,3,6,7-tetramethylanthracene solid, melting point is 299°C.

[0124] 1 HNMR (400MHz, CDCl3): δ=2.43(s,12H),7.68(s,4H),8.13(s,2H)

[0125] Weigh 2g of 2,3,6,7-tetramethylanthra...

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Abstract

The invention discloses a high-purity ptyltetracid dianhydride and a synthesis method thereof, and polyimides synthesized on the basis of the ptyltetracid dianhydride. The method comprises the following steps: carrying out Friedel-Crafts reaction on cheap accessible industrial dichloromethane and o-xylene by using anhydrous AlCl3 as a catalyst to obtain 2,3,6,7-tetramethyl anthracene, carrying out D-A addition on the 2,3,6,7-tetramethyl anthracene and anthranilic acid or equivalent thereof to obtain 2,3,6,7-tetramethyl triptycene and derivative thereof tetramethylptycene, and oxidizing to obtain high-value ptyltetraformic acid; and carrying out high-temperature high-pressure solvothermal synthesis on the ptyltetraformic acid to obtain the corresponding high-purity high-yield ptyltetracid dianhydride. The solvothermal method for synthesizing dianhydride is suitable for dianhydride which can not be easily purified under normal pressure, and has the advantages of low loss and high yield. The ptyltetracid dianhydride and biphenyl diamines with different substituent groups are polycondensed by a one-step process to obtain a series of novel polyimides.

Description

【Technical field】 [0001] The invention relates to a high-purity pterene tetraacid dianhydride, a synthesis method thereof and a polyimide synthesized based on the dianhydride monomer. 【Background technique】 [0002] Aromatic polyimide, as a class of important structural and functional materials, has a wide range of uses in microelectronics technology, aerospace, etc. Due to the very stable aromatic heterocyclic structure in polyimide molecules, it reflects other Polymer materials have incomparable excellent performance, but the contradiction between high performance and processability greatly limits its application. Nowadays, the more common method for synthesizing linear polyarimides is the polycondensation reaction between dianhydride and diamine monomers. Since the commercialization of diamines has been very mature, it is of great significance to develop new dianhydride monomers from the design of monomer molecules to expand the application of polyimides. [0003] In re...

Claims

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Application Information

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IPC IPC(8): C07D493/08C08G73/10
CPCC07D493/08C08G73/1067
Inventor 程琳肖友华邵宇
Owner HUAQIAO UNIVERSITY
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