Aromatic diamine containing phthalonitrile side group and synthesis method and application thereof

A technology of phthalonitrile and aromatic diamine, applied in chemical instruments and methods, preparation of carboxylic acid nitrile, preparation of organic compounds, etc. The effect of improved properties such as thermal properties and solvent resistance

Inactive Publication Date: 2013-03-27
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it can be seen from the structure of polyamide-imide that it has the advantages of both polyimide and polyamide, and at the same time it will also show the disadvantages of their poor additive properties as mentioned above, but so far, no There are reports of introducing nitrile groups into polyamideimide to improve its processing properties

Method used

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  • Aromatic diamine containing phthalonitrile side group and synthesis method and application thereof
  • Aromatic diamine containing phthalonitrile side group and synthesis method and application thereof
  • Aromatic diamine containing phthalonitrile side group and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Example 1: Synthesis of aromatic diamine 2a containing phthalonitrile side groups (R in the structural formula is CF3CCF3)

[0045] Raw materials include 4-nitrophthalonitrile, 1a, potassium carbonate, and dimethylsulfoxide, wherein the molar ratio of 4-nitrophthalonitrile to 1a is 2:1, and the molar ratio of potassium carbonate to 1a The ratio is 3:1, the volume of dimethyl sulfoxide: the sum of the mass of 4-nitrophthalonitrile and 1a is 10:2, the unit of measurement of the volume is mL, and the unit of measurement of the mass is g.

[0046] Add 4.73g (27.3mmol) 4-nitrophthalonitrile, 5g (13.65mmol) 1a, 5.67g (40.95mmol) potassium carbonate, 48.7ml dimethyl sulfoxide to the reaction vessel, under nitrogen protection, React at 5°C for 24h. After the reaction, pour the reaction solution into tap water to precipitate, then filter, wash the obtained filter cake with tap water until neutral, and dry it under vacuum at 50°C for 24h to obtain 2a with a yield of 90.3%.

[0...

Embodiment 2

[0048] Example 2: Synthesis of aromatic diamine 2b containing phthalonitrile side groups (R in the structural formula is CH3CCH3)

[0049] Raw materials include 3-nitrophthalonitrile, 1b, potassium carbonate, N,N-dimethylformamide, wherein the molar ratio of 3-nitrophthalonitrile to 1b is 2.05:1, potassium carbonate The molar ratio to 1b is 3.5:1, the volume of N,N-dimethylformamide: the sum of the masses of 3-nitrophthalonitrile and 1b is 10:2.2, and the unit of measurement for said volume is mL , the unit of measurement of the mass is g.

[0050] Add 5.5 g (31.73 mmol) 3-nitrophthalonitrile, 4 g (15.48 mmol) 1b, 7.49 g (54.18 mmol) potassium carbonate, 43.2 ml N,N-dimethylformamide to the reaction vessel under nitrogen atmosphere Under protection, react at 15°C for 20h. After the reaction, pour the reaction solution into deionized water to precipitate, then filter, wash the obtained filter cake with deionized water until neutral, and vacuum dry at 60°C for 20h to obtain 2b....

Embodiment 3

[0052] Example 3: Synthesis of aromatic diamine 2c containing phthalonitrile side groups (R in the structural formula is O)

[0053] Raw materials include 4-nitrophthalonitrile, 1c, potassium carbonate, N,N-dimethylacetamide, wherein the molar ratio of 4-nitrophthalonitrile to 1c is 2.1:1, potassium carbonate The molar ratio to 1c is 4:1, the volume of N,N-dimethylacetamide: the sum of the masses of 4-nitrophthalonitrile and 1c is 10:2.5, and the unit of measurement for said volume is mL , the unit of measurement of the mass is g.

[0054] Add 15.66 g (90.43 mmol) 4-nitrophthalonitrile, 10 g (43.06 mmol) 1c, 23.8 (172.24 mmol) g potassium carbonate, 102.6 ml N,N-dimethylacetamide to the reaction vessel under nitrogen atmosphere Under protection, react at 20°C for 15h. After the reaction, pour the reaction solution into deionized water to precipitate, then filter, wash the obtained filter cake with deionized water until neutral, and dry it in vacuum at 80°C for 10h to obtain 2...

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Abstract

The invention discloses aromatic diamine containing phthalonitrile side group, which is characterized in that the structural formula is shown in the specification, wherein R is one of CF3CCF3, CH3CCH3, O, CO and S. A preparation method of the aromatic diamine containing phthalonitrile side group comprises the following steps of: adding 4-nitrophthalonitrile or 3-nitrophthalonitrile, a compound 1, potassium carbonate and a high-boiling point solvent into a reaction container; conducting reaction for 10-24 hours at room temperature under protection of nitrogen; and then precipitating, filtering and drying. The aromatic diamine containing phthalonitrile side group can be applied to the preparation of polyimide, polyamide and polyamide-imide.

Description

technical field [0001] The invention belongs to the field of polymer materials, in particular to aromatic diamines containing phthalonitrile side groups and their synthesis methods and applications. Background technique [0002] Polyimide refers to a class of polymers containing imide rings in the main chain structure. It has attracted extensive attention due to its excellent thermal stability, mechanical properties, chemical inertness, dielectric properties and radiation resistance. Commodity forms such as coatings, fibers, plastics, adhesives and resin-based composites are widely used in high-tech fields such as aerospace and electronics industries. Polyimide can be mainly divided into non-crosslinked polyimide and thermosetting polyimide, among which, thermosetting polyimide has better processability and comprehensive performance. Most of the existing thermosetting polyimides are oligomers or polymers with active phenylacetylene or acetylene groups as end groups, side gr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/37C07C319/20C07C253/30C07C255/54C08G73/10C08G69/32
Inventor 杨刚曾科向首容武迪蒙
Owner SICHUAN UNIV
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