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Phthalonitrile monomer containing aromatic polyamide, synthetizing method thereof and poly phthalonitrile resin produced through solidification of phthalonitrile monomer

A technology of polyphthalonitrile resin and phthalonitrile, which is applied to the preparation of carboxylic acid nitrile, the preparation of organic compounds, chemical instruments and methods, etc., and can solve the problem of increasing the complexity of resin processing and the large difference in molecular structure , unfavorable industrial production and other issues, to achieve the effect of avoiding complex blending process, simple method and easy promotion

Inactive Publication Date: 2012-09-12
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it is very regrettable that the molecular structure of the commonly used diarylamine or phenolic curing agent and phthalonitrile derivatives is quite different. If only through simple physical blending, it is often difficult to achieve molecular level mixing, while Although melt blending can meet the mixing requirements, it increases the complexity of resin processing and high energy consumption, which is not conducive to industrial production

Method used

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  • Phthalonitrile monomer containing aromatic polyamide, synthetizing method thereof and poly phthalonitrile resin produced through solidification of phthalonitrile monomer
  • Phthalonitrile monomer containing aromatic polyamide, synthetizing method thereof and poly phthalonitrile resin produced through solidification of phthalonitrile monomer
  • Phthalonitrile monomer containing aromatic polyamide, synthetizing method thereof and poly phthalonitrile resin produced through solidification of phthalonitrile monomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Add 4-(4-carboxyphenoxy)phthalonitrile and m-phenylenediamine in a molar ratio of 2:1 to DMF, stir and mix at room temperature, and make the solid content 30% (w / v), then add The dehydrating agent DCC is 1:2.5 based on the molar ratio of carboxylic acid raw materials, and reacted at 10°C for 12h. After the reaction, the filtrate was collected by filtration, and the filtrate was distilled to a solid content of 80% (w / v), and then the filter cake was collected by filtration. After the filter cake was dried at 80°C to constant weight, the phthalophthalamide containing aromatic amide with the following structure was obtained. Carbonitrile monomer 1. The minimum melt viscosity of the monomer 1 is 0.12Pa.S; IR(KBr, cm -1 ): 3315(N-H), 2231(C≡N), 1655(C=O), 1088(C-O-C); 1 H-NMR (DMSO-d6): 10.05 (2H, N-H), 8.02 (1H, Ar-H), 7.91 (4H, Ar-H), 7.65 (2H, Ar-H), 7.38 (4H, Ar-H ), 7.35(2H, Ar-H), 7.22(1H, Ar-H), 7.10(4H, Ar-H).

[0033] Put the above monomer 1 in a nitrogen atmosp...

Embodiment 2

[0035] Add 3-(4-carboxyphenoxy)phthalonitrile and p-phenylenediamine in a molar ratio of 2.1:1 into DMAc and stir at room temperature to mix evenly, and make the solid content 50% (w / v), then add The dehydrating agent TPP is 1:3 based on the molar ratio of the carboxylic acid raw material, and reacted at 80° C. for 4 hours. After the reaction, the filtrate was collected by filtration, and the filtrate was distilled to a solid content of 85% (w / v), and then the filter cake was collected by filtration. After the filter cake was dried at 90°C to a constant weight, the phthalophthalamide containing aromatic amide with the following structure was obtained. Carbonitrile monomer 2. The minimum melt viscosity of the monomer 2 is 0.32Pa.S; IR(KBr, cm -1 ): 3300(N-H), 2232(C≡N), 1658(C=O), 1091(C-O-C); 1H-NMR (DMSO-d6): 10.1 (2H, N-H), 7.91 (4H, Ar-H), 7.68 (2H, Ar-H), 7.62 (4H, Ar-H), 7.41 (2H, Ar-H ), 7.38(2H, Ar-H), 7.10(4H, Ar-H).

[0036] Put the above monomer 2 in a nitrogen a...

Embodiment 3

[0038] Add 4-(3-carboxyphenoxy)phthalonitrile and 1,3,5-m-phenylenediamine in a molar ratio of 3.5:1 into NMP, stir and mix evenly at room temperature, and make the solid content 20% (w / v), then add the dehydrating agent NNPB with a molar ratio of carboxylic acid raw materials of 1:5, and react at 30°C for 6h. After the reaction, the filtrate was collected by filtration, and the filtrate was distilled to a solid content of 90% (w / v), and then the filter cake was collected by filtration. After the filter cake was dried at 120°C to constant weight, the phthalamide containing aromatic amide of the following structure was obtained: Carbonitrile monomer 3. The minimum melt viscosity of the monomer 3 is 0.32Pa.S; IR(KBr, cm -1 ): 3308(N-H), 2230(C≡N), 1654(C=O), 1090(C-O-C);

[0039] 1 H-NMR (DMSO-d6): 10.08 (3H, N-H), 7.76 (3H, Ar-H), 7.67 (3H, Ar-H), 7.65 (3H, Ar-H), 7.61 (3H, Ar-H ), 7.40(3H, Ar-H), 7.38(3H, Ar-H), 7.35(3H, Ar-H), 7.17(3H, Ar-H).

[0040] Put the above-ment...

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Abstract

The invention discloses a phthalonitrile monomer containing aromatic polyamide, which is characterized in that a structural formula of the monomer is shown in the description, wherein R1, R2 and R3 are groups shown in the description or H atoms, which can be identical or can be different, and at least one substituent group of the R1, R2 and R3 contains an amide group, and a carbonyl C=0 characteristic peak displayed through an infrared spectrogram of the monomer is between 1650 and 1660. The invention also discloses a preparation method of the monomer and prepared poly phthalonitrile resin by using the monomer. The phthalonitrile is a monomer having an autoacceleration thermal polymerization behavior, during solidification of the phthalonitrile, no arylamine or phenolic curing agent is required to be added, the cost is saved, the operation is simplified, the quality can be controlled easily, besides, defects of a traditional phthalonitrile resin two-component system that the blending process is complex, the energy consumption is high and the like are avoided, and industrial production is facilitated. The method is simple, mature, easy to operate and control, and convenient for application.

Description

technical field [0001] The invention belongs to the technical field of phthalonitrile monomer and its synthesis, and in particular relates to the synthesis of aramid-containing phthalonitrile monomer (APN) and its synthesis method and its solidification to prepare polyphthalonitrile Resin method. Background technique [0002] Polyphthalonitrile resin obtained by thermal curing of phthalonitrile monomer is a kind of high-performance thermosetting resin. Due to its excellent flame retardancy and high-temperature mechanical properties, it has been widely used in high-tech fields such as aerospace and aerospace as a matrix resin for high-performance composite materials and high-temperature-resistant hot-melt adhesives. [0003] However, the thermal curing reaction of polyphthalonitrile resin is very slow, and the gel of the resin has not been observed after nearly 100 hours of reaction at 260°C, resulting in a long processing cycle and increased cost. In order to change this s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/54C07C253/30C08G73/06
Inventor 杨刚曾科武迪蒙邱凯
Owner SICHUAN UNIV
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