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Synthesis method of phthalonitrile and arylacetylene-terminated aromatic imide

A technology of phthalonitrile and arylimide, applied in the field of synthesis of arylimide monomers, can solve the problems of low processing efficiency, difficult processing, slowness and the like

Active Publication Date: 2014-11-05
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, polyphthalonitrile resins and polyarylene resins also have some difficulties that need to be improved during processing.
For example, the curing of phthalonitrile resins is an extremely slow, high-temperature process, resulting in inefficient and costly processing
However, the curing process of arylacetylene resin is too intense, and even violent polymerization may occur, resulting in a narrow processing window and difficult processing

Method used

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  • Synthesis method of phthalonitrile and arylacetylene-terminated aromatic imide
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  • Synthesis method of phthalonitrile and arylacetylene-terminated aromatic imide

Examples

Experimental program
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Effect test

Embodiment 1

[0069] 1.1. Synthesis of one-component system phthalonitrile and phenylacetylene-terminated imide monomer a1

[0070] 1.1.1. Synthesis of Intermediate 1

[0071] Put 3.10g of 4,4'-biphenyl ether dianhydride (ODPA) into 7ml of NMP, and after ODPA is completely dissolved, slowly add compound B (the structural formula of compound B) into the ODPA solution dropwise at room temperature The NMP solution (the mol ratio of ODPA and compound B is 1:1, V NMP =(total solid mass (g)*2)mL), after the dropwise addition was completed, react at room temperature for 6h. Then add acetic anhydride and pyridine (ODPA: acetic anhydride: pyridine molar ratio is 1:6:6) into the reaction solution, after the addition is completed, the temperature is raised to 100° C. for 3 h. Then lower the temperature, precipitate with anhydrous methanol, filter, collect the filtrate, and distill the filtrate under reduced pressure to remove methanol. Afterwards, the obtained concentrated solution was washed with ...

Embodiment 2

[0085] 2.1. Synthesis of one-component system phthalonitrile and phenylacetylene-terminated imide monomer a2

[0086] 2.1.1. Synthesis of intermediate 1

[0087] With the pyromellitic anhydride (PMDA) of 2.18g, drop in the DMF of 22ml, after treating that PMDA dissolves completely, in the PMDA solution, slowly add the DMF solution that dissolves compound B (the mol of PMDA and compound B) in the PMDA solution at room temperature The ratio is 1:1.2, V DMF =(Total solid mass (g)*10)mL) After the dropwise addition was completed, react at room temperature for 12 hours. Then add acetic anhydride and pyridine (the molar ratio of PMDA: acetic anhydride: pyridine is 1:6:6) to the reaction liquid, and after the addition is completed, the temperature is raised to 120° C. for 6 h. Then lower the temperature, precipitate with anhydrous methanol, filter, collect the filtrate, and distill the filtrate under reduced pressure to remove methanol. Afterwards, the obtained solid was washed wi...

Embodiment 3

[0101] 3.1. Synthesis of one-component system phthalonitrile and phenylacetylene-terminated imide monomer a3

[0102] 3.1.1. Synthesis of intermediate 1

[0103] Put 2.94g of 3,3',4,4'-biphenyltetracarboxylic anhydride (BPDA) into 10ml of DMAc, and after the BPDA is completely dissolved, slowly add the dissolved compound B into the BPDA solution at room temperature (the structural formula of compound B is as shown in the following synthesis process) DMAc solution (the mol ratio of BPDA and compound B is 1:1.1, V DMAC =(total solid mass (g)*3.3)mL) After the dropwise addition, react at room temperature for 9h. Then add acetic anhydride and pyridine (the molar ratio of BPDA: acetic anhydride: pyridine is 1:6:6) to the reaction solution, and after the addition is completed, the temperature is raised to 110° C. for 4.5 hours. Then lower the temperature, precipitate with anhydrous methanol, filter, collect the filtrate, and distill the filtrate under reduced pressure to remove me...

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Abstract

The invention discloses a synthesis method of phthalonitrile and arylacetylene-terminated aromatic imide. The method comprises the following steps: I, synthesis of a single-component system: reacting tetracid dianhydride serving as a raw material with a raw material containing amine phthalonitrile in a polar solvent to obtain an intermediate 1, adding acetic anhydride to obtain an intermediate 2, and reacting the intermediate 2 with a raw material containing amine arylacetylene to obtain a target product; and II, synthesis of a multi-component system: reacting the tetracid dianhydride serving as the raw material with the raw material containing the amine phthalonitrile to obtain a first monomer; reacting the raw material containing the amine arylacetylene with the tetracid dianhydride serving as the raw material to obtain a second monomer; and performing melt blending or solution blending on the first monomer and the second monomer to obtain a target product. By adopting the synthesis method, the aromatic polyimide, a polyphthalonitrile resin and a polyarylacetylene resin are introduced into the same curing system through physical blending or chemical modification, so that the processing performance of the product can be improved effectively, and the processing cost is lowered.

Description

technical field [0001] The invention relates to a synthesis method of an aromatic imide monomer whose end-capping groups are phthalonitrile and arylacetylene and the technical field of its use in the preparation of polyphthalonitrile and polyarylacetylene blended resins. Background technique [0002] Aromatic polyimide has become the most potential material of choice for manufacturing aerospace vehicles and propulsion systems due to its outstanding heat resistance, excellent mechanical properties and stability. However, due to the extremely strong rigidity and intermolecular force of the polyimide molecular chain, it is difficult to melt and dissolve and is not easy to process. Polyphthalonitrile resin and polyarylene resin are two types of thermosetting resins with excellent heat resistance, mechanical properties and flame retardancy. They are at the same level as polyimide in terms of heat resistance and mechanical properties and they are During the curing process, no sma...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/48C07D487/04C08G73/10
CPCC07D209/48C07D487/04C08G73/1007
Inventor 曾科杨刚刘燕翠胡江淮袁萍刘娇健卞棋牛彦存
Owner SICHUAN UNIV
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