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Phthalonitrile monomer containing phthalimide and its preparation method and application

A technology of phthalimide and phthalonitrile, applied in the field of polymer material processing, which can solve the problems of small molecular weight, poor thermal stability and thermal oxygen stability, and reduced performance

Active Publication Date: 2017-01-25
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But above-mentioned curing agent all has two fatal shortcoming: 1, the general molecular weight of used curing agent is relatively small, and the curing process of phthalonitrile resin is a high-temperature process (requires more than 375 ℃ for post-curing), small in the curing process The molecular curing agent will inevitably volatilize, so that there are defects in the material, and the performance is reduced (S B.Sastri, TM.Keller.Phthalonitrile CureReaction with Aromatic Diamines.J.Polym.Sci., Part A.:Polym.Chem. .Vol.36,1885–1890(1998)
2. Phthalonitrile resins often need to withstand high temperatures above 300°C for a long time when used as high-temperature resistant materials, and amines and other curing agents have poor thermal stability and thermal oxygen stability at high temperatures. Will reduce the mechanical properties of the resin

Method used

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  • Phthalonitrile monomer containing phthalimide and its preparation method and application
  • Phthalonitrile monomer containing phthalimide and its preparation method and application
  • Phthalonitrile monomer containing phthalimide and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] (1) Synthesis of Intermediate 1

[0057] Using 3.10g of 3,3',4,4'-diphenyl ether tetra-acid dianhydride (ODPA), 4-(3-aminophenoxy)phthalonitrile, acetic anhydride and pyridine as raw materials, tetra-acid di The mol ratio of anhydride and 4-(3-aminophenoxy) phthalonitrile is 1.0:1.0, and the mol ratio of tetraacid dianhydride, acetic anhydride, pyridine is: tetraacid dianhydride: acetic anhydride: pyridine=1.0 :6.0:6.0.

[0058] Dissolve tetra-acid dianhydride (ODPA) in 6.2mL NMP, heat to dissolve completely and cool to room temperature, dissolve 4-(3-aminophenoxy)phthalonitrile in twice its mass (g) In the polar solvent NMP of volumetric amount (mL), form solution, under stirring, 4-(3-aminophenoxy group) phthalonitrile solution is dripped in ODPA solution with the rate of addition of 0.15mL / min, After the dropwise addition, react at room temperature for 6 hours under stirring, then add acetic anhydride and pyridine to the above reaction solution under stirring, and ...

Embodiment 2

[0077] (1) Synthesis of intermediate 1

[0078] With 2.18g pyromellitic anhydride (PMDA), 4-(2-aminophenoxy) phthalonitrile, acetic anhydride and pyridine as raw materials, PMDA and 4-(2-aminophenoxy) phthalonitrile The mol ratio of formonitrile is 1.0:1.2, and the mol ratio of PMDA, acetic anhydride, pyridine is: PMDA acetic anhydride: pyridine=1.0:3.0:3.0;

[0079] Dissolve PMDA in 21.8mL DMF, heat it to dissolve completely and cool to room temperature, dissolve 4-(2-aminophenoxy)phthalonitrile in volume (mL) 10 times its mass (g) In the limiting solvent DMF, under stirring, 4-(2-aminophenoxy) phthalonitrile solution was dripped into PMDA solution at a rate of 1.5mL / min, and reacted at room temperature under stirring after the dropwise addition 8h, then add acetic anhydride and pyridine to the above reaction solution under stirring, and heat up to 115°C for 5h of heat preservation reaction, after the reaction is completed, naturally cool to room temperature, then pour the r...

Embodiment 3

[0096] (1) Synthesis of Intermediate 1

[0097] With 2.94g 3,3',4,4'-biphenyltetracarboxylic anhydride (BPDA), 4-(4-aminophenoxy)phthalonitrile, acetic anhydride and pyridine as raw materials, BPDA and 4-( The molar ratio of 4-aminophenoxy)phthalonitrile is 1.0:1.1, and the molar ratio of tetraacid dianhydride, acetic anhydride, and pyridine is: tetraacid dianhydride:acetic anhydride:pyridine=1.0:7.0:7.0.

[0098] Dissolve BPDA in 11.8mL polar solvent DMAC, heat it to dissolve completely and cool to room temperature, dissolve 4-(4-aminophenoxy)phthalonitrile in a volume that is 4 times its mass (g) (mL) of the limiting solvent DMAC, under stirring, the 4-(4-aminophenoxy) phthalonitrile solution was dripped into the BPDA solution at a rate of 0.60mL / min, and after the dropwise addition, under stirring React at room temperature for 11 hours, then add acetic anhydride and pyridine to the above reaction solution with stirring, and heat up to 125°C for 3.5 hours. After the reactio...

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Abstract

The invention discloses a phthalimide-containing phthalonitrile monomer. The phthalimide-containing phthalonitrile monomer has a structural formula shown in the description. In the structural formula, R1 represents one of the groups shown in the description and in the above group, R3 represents one of two groups shown in the description, O, S, SO2, CO, C(CH3)2 and C(CF3)2. In the structural formula, R2 represents the group shown in the description and in the above group, R4 represents H or the group shown in the description. A preparation method of the phthalimide-containing phthalonitrile monomer utilizes a three-step method or a two-step method. The invention also provides a use of the phthalimide-containing phthalonitrile monomer in preparation of phthalonitrile resin.

Description

technical field [0001] The invention belongs to the technical field of polymer material processing, and relates to a compound containing a phthalimide group and a phthalonitrile group and a preparation method thereof. Background technique [0002] Due to its high thermal stability, thermal oxygen stability, low flammability, chemical corrosion resistance and excellent high-temperature mechanical properties, phthalonitrile resin has been widely used as a matrix resin for high-performance composite materials in aerospace, etc. high-tech field. Phthalonitrile resins are formed by curing phthalonitrile monomers, but the existing phthalonitrile monomers are cured without a curing agent is an extremely slow process (generally at 300 ° C, more than a week Viscosity can not be significantly increased), resulting in difficult processing and high processing costs, thereby limiting the application of this type of resin. Adding curing agent can increase the curing speed of phthalonitr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/48C07D487/04C08G73/06
CPCC07D209/48C07D487/04C08G73/06
Inventor 杨刚曾科胡江淮刘燕翠姬素春袁萍刘娇建卞棋牛彦存
Owner SICHUAN UNIV