Low-viscosity thermosetting polyimide resin and preparation method and application thereof

A polyimide resin, thermosetting technology, applied in the field of low viscosity thermosetting polyimide resin and its preparation, can solve the problems of poor solubility, limit polyimide processing and application, high melt viscosity, etc., and achieve low melting Viscosity, easy proportioning of reaction raw materials, and the effect of reducing melt viscosity

Active Publication Date: 2016-04-06
NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the traditional polyimide resin has a rigid aromatic ring structure in the main chain, and the structure is a geometrically symmetrical and coplanar structure, which makes the traditional polyimide resin have strong intermolecular forces, resulting in high melt viscosity. , poor solubility, which limits the processing and application of polyimide

Method used

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  • Low-viscosity thermosetting polyimide resin and preparation method and application thereof
  • Low-viscosity thermosetting polyimide resin and preparation method and application thereof
  • Low-viscosity thermosetting polyimide resin and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] In this example, the mixed thioether dianhydride contains three structures of 3,3'-TDPA, 3,4'-TDPA and 4,4'-TDPA. Wherein the molar ratio is n(3,3'-TDPA):n(3,4'-TDPA):n(4,4'-TDPA)=17:58:25.

[0048] In this embodiment, the polyimide resin has the following structural formula:

[0049]

[0050] Add 4.0048g (0.02mol) 4,4′-diaminodiphenyl ether into a dry and clean 100mL three-necked flask, add N-methylpyrrolidone as a solvent, protect it with nitrogen, stir at room temperature, and add 3.2628g (0.01mol) ) mixed thioether dianhydride, reacted for 5 hours and then added 4.9648 g (0.02 mol) of end-capping agent 4-phenylacetylene phthalic anhydride, added N-methylpyrrolidone until the solid content of the solution was 30%, and continued to react for 10 hours. Add 10ml of toluene to the solution and raise the temperature to 180°C. Reflux with water for 2h. Release the toluene in the water separator, and when the toluene condensed in the water separator reaches about 10ml...

Embodiment 2

[0054] In this example, the mixed thioether dianhydride contains three structures of 3,3'-TDPA, 3,4'-TDPA and 4,4'-TDPA. Wherein the molar ratio is n(3,3'-TDPA):n(3,4'-TDPA):n(4,4'-TDPA)=15:61:24.

[0055] In this embodiment, the polyimide resin has the following structural formula:

[0056]

[0057] Add 4.8058g (0.024mol) 4,4'-diaminodiphenyl ether into a dry and clean 100mL three-necked flask, add N-methylpyrrolidone as a solvent, protect it with nitrogen, stir at room temperature, and add 6.5256g (0.02mol) ) mixed thioether dianhydride, reacted for 4 hours and then added 1.9859 g (0.008 mol) of end-capping agent 4-phenylacetylene phthalic anhydride, added N-methylpyrrolidone until the solid content of the solution was 30%, and continued to react for 12 hours. Add 10ml of toluene to the solution, raise the temperature to 180°C, and reflux with water for 3h. Release the toluene in the water separator, and when the toluene condensed in the water separator reaches about 10...

Embodiment 3

[0061] In this example, the mixed thioether dianhydride contains three structures of 3,3'-TDPA, 3,4'-TDPA and 4,4'-TDPA. Wherein the molar ratio is n(3,3'-TDPA):n(3,4'-TDPA):n(4,4'-TDPA)=19:54:27.

[0062] In this embodiment, the polyimide resin has the following structural formula:

[0063]

[0064] Add 6.4077g (0.032mol) 4,4'-diaminodiphenyl ether into a dry and clean 100mL three-necked flask, add N-methylpyrrolidone as a solvent, protect it with nitrogen, stir at room temperature, and add 9.1358g (0.028mol) ) mixed with thioether dianhydride, after 5 hours of reaction, 1.9857 g (0.008 mol) of 4-phenylacetylene phthalic anhydride was added, and N-methylpyrrolidone was added until the solid content of the solution was 30%, and the reaction was continued for 10 hours. Add 10ml of toluene to the solution and raise the temperature to 180°C. Reflux with water for 2h. Release the toluene in the water separator, and when the toluene condensed in the water separator reaches ab...

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Abstract

The invention relates to low-viscosity thermosetting polyimide resin and a preparation method thereof. The method comprises the following steps that diamine monomers and mixed thioether dianhydride are added to organic solvent to be reacted for 4-6 h; an end capping agent is added to be reacted continuously for 8-12 h; a water removing agent is added, the temperature of a reaction system rises to 175-185 DEG C, reflux is conducted for 1-3 h, and the water removing agent and water in the system are removed through distillation; the temperature rises continuously to 190-210 DEG C, and a reflux condensation reaction is conducted for 1-3 h; the reaction system is cooled and poured into precipitator, filtration, cleaning and drying are conducted, and the low-viscosity thermosetting polyimide resin is obtained. The invention further relates to application of the low-viscosity thermosetting polyimide resin in thin films or engineering plastics or composites. Due to the fact that -S- and -O- flexible units are introduced into a main chain of the low-viscosity thermosetting polyimide resin, and the main chain contains asymmetric and non-coplanar structural units, the low melt viscosity, good dissolving property and high vitrification transition temperature are achieved.

Description

technical field [0001] The invention relates to the technical field of polyimide resin and its preparation method, in particular to a low-viscosity thermosetting polyimide resin and its preparation method and application. Background technique [0002] Due to its excellent comprehensive properties, such as excellent thermal stability, good mechanical properties and chemical stability, polyimide has been widely used in high-tech fields such as aerospace and electronic appliances. Compared with thermoplastic polyimide, thermosetting polyimide has higher temperature resistance and better processing performance, and is often used as resin matrix for advanced composite materials and high-temperature adhesives. [0003] U.S. Patent US5412066 "Phenylethynylterminated oligomers" reported the preparation method of thermosetting polyimide resin using 4-phenylacetylene phthalic anhydride as the end-capping agent. The obtained prepolymer has a wide processing window, good solubility, low...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/10C08L79/08
CPCC08G73/1014C08G73/1067C08L79/08
Inventor 方省众孙璐王玮陈国飞
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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