Multi-alkyl-substituted diamine compound containing polycyclic aromatic hydrocarbon structure and preparation method and application thereof

A technology for amine compounds and fused-ring aromatics, which is applied in the field of diamine compounds substituted by polyalkylenes containing fused-ring aromatics and its preparation, can solve the problem of single substitution positions of alkyl groups, and achieve large number of alkyl groups and tight packing Small, CTC effect inhibition effect

Inactive Publication Date: 2017-06-13
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The side groups of the polyalkyl-substituted diamine monomers reported in these patents are all phenyl or fluorinated benzene derivatives, and at the same time, the alkyl substitution position is single

Method used

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  • Multi-alkyl-substituted diamine compound containing polycyclic aromatic hydrocarbon structure and preparation method and application thereof
  • Multi-alkyl-substituted diamine compound containing polycyclic aromatic hydrocarbon structure and preparation method and application thereof
  • Multi-alkyl-substituted diamine compound containing polycyclic aromatic hydrocarbon structure and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] The diamine structural formula that present embodiment synthesizes is as follows:

[0039]

[0040] The synthesis steps of the above-mentioned diamine are as follows: put 16.63g of aniline in a 100mL three-necked flask, stir, blow nitrogen to replace the air in the bottle, and after heating to 130°C, use a dropping funnel to mix 7.87g of 1-naphthaldehyde and 4.2mL of concentrated The hydrochloric acid mixed solution was dropped into the reaction system, and the temperature was maintained for 18 hours. The reaction system became thick and dark brown. After the reaction, the temperature of the system was lowered to 60° C., and 10 g of 20 wt % sodium hydroxide aqueous solution was added dropwise with stirring, and then dropped into 100 mL of methanol to precipitate a solid. After filtration, the solid was washed with methanol and water for several times, and then recrystallized with methanol to precipitate brown-yellow crystals, which were collected by filtration and dr...

Embodiment 2

[0046] The diamine structural formula that present embodiment synthesizes is as follows:

[0047]

[0048] The synthesis steps of the above-mentioned diamine are as follows: 15.59 g of 2,6-dimethylaniline was placed in a 100 mL three-necked flask, stirred, the air in the flask was replaced by nitrogen gas, and heated to 80°C. Mix 4.29g of 1-naphthaldehyde with 2.5mL of concentrated hydrochloric acid to activate it, and drop the activated 1-naphthaldehyde solution into the reaction system within 1.5h. Then heated to 120 ° C, reflux reaction 10h. As the reaction progressed, the reaction system changed from a brown solution to a blue one, and finally turned into a blue viscous liquid. After the system dropped to 60° C., 7.5 g of 20 wt % sodium hydroxide aqueous solution was added. The temperature was then lowered to room temperature, and the reaction system was added into 200 mL of methanol under stirring, and a pale yellow solid was precipitated. After filtering, washing t...

Embodiment 3

[0054] The diamine structural formula that present embodiment synthesizes is as follows:

[0055]

[0056] The synthesis steps of the above-mentioned diamine are as follows: sequentially add 22.33g of 2,6-diisopropylaniline, 15mL of water, and 30mL of ethylene glycol methyl ether into a 100mL three-necked bottle, replace the air in the bottle with nitrogen, and heat to 90°C. Slowly drop 7.5mL of concentrated sulfuric acid into the bottle to obtain a colorless and transparent solution, then drop in 10.40g of 1-naphthaldehyde, raise the temperature to 100°C, and react for 14h. A yellow precipitate appeared in the reaction system. After the reaction, cool down to room temperature, add the reaction system to 800 mL of water, adjust the pH to 9-10, stir for 4 hours, obtain a solid by filtration, and wash the solid repeatedly with a large amount of water. Dissolve the solid in dichloromethane, extract it with water three times, remove the inorganic salt, remove the dichlorometha...

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Abstract

The invention belongs to the technical field of material science, and particularly discloses a multi-alkyl-substituted diamine compound containing a polycyclic aromatic hydrocarbon structure. A structural formula is shown in formula (I) or formula (II), wherein X is hydrogen or an alkyl group; Y is hydrogen, a phenyl group, a substituted phenyl group, a polycyclic aromatic hydrocarbon group, a hydroxyl group or a halide group. The multi-alkyl-substituted diamine compound containing the polycyclic aromatic hydrocarbon structure is characterized in that the steric hindrance of the polycyclic aromatic hydrocarbon group on a molecular structure is large, the number of alkyl groups is more, the structure is favorably regulated and controlled, the structure of a polyimide molecular chain prepared by the monomer is twisted, the stacking compactness is little, and the CTC (charge transfer complex) effect in molecular chains and between the molecular chains is inhibited; because the stability of the polycyclic aromatic hydrocarbon structure is high, the heat stability of the polymer is favorably maintained. The multi-alkyl-substituted diamine compound has the advantages that the synthesis is simple, the obtaining of raw materials is easy, and the diamine compound is suitable for industrial production; the diamine compound has large potential in preparation of dissolvable and transparent polyimide, and is suitable for synthesizing polyamide and polyamideimide high-performance materials.

Description

technical field [0001] The invention belongs to the technical field of material science, and more specifically relates to a polyalkyl-substituted diamine compound containing a polycyclic aromatic hydrocarbon structure and a preparation method and application thereof. Background technique [0002] Polyimide is a kind of polymer material containing imide ring structure. It has excellent heat resistance, chemical stability, mechanical properties and dielectric properties. It has been widely used in aerospace, electrical, and automotive and many other fields. However, due to the high conjugation of the molecular chains of traditional polyimides, charge transfer complexes (charge transfer complexes, CTCs) are formed between molecules and within molecules, which makes polyimides poor in solubility and dark in color, which limits It is used in high-tech fields such as microelectronics and optoelectronics. Therefore, the research and development of soluble and colorless polyimide ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/50C07C209/78C08G73/10
CPCC07C209/78C08G73/10
Inventor 陈永明黎天云王雷黄华华
Owner SUN YAT SEN UNIV
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