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2-amino-fluorene containing ester group and preparation method thereof

A technology containing ester group-containing diaminofluorene and ester group-containing dinitrofluorene, which is applied in the field of organic polymer materials, can solve the problems of poor toughness of polymers and high rigidity of molecular chains, and achieve the effect of improving flexibility

Inactive Publication Date: 2012-08-01
HARBIN ENG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of the above-mentioned diamines is that the molecular chain is rigid, resulting in poor toughness of the polymer

Method used

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  • 2-amino-fluorene containing ester group and preparation method thereof
  • 2-amino-fluorene containing ester group and preparation method thereof
  • 2-amino-fluorene containing ester group and preparation method thereof

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preparation example Construction

[0018] The basic preparation method of ester group-containing diaminofluorene of the present invention comprises:

[0019] The first step: Add dihydroxyfluorene, organic solvent and triethylamine in sequence to the container equipped with agitator, condenser and thermometer. The concentration of dihydroxyfluorene in the organic solvent is 50-200g / L, organic solvent and triethylamine The volume ratio of ethylamine is 1:1. Under the condition of -10~10℃, add dropwise to the organic solvent containing p-nitrobenzoyl chloride prepared in advance. The concentration of p-nitrobenzoyl chloride solution is 10~40g / L, the molar ratio of dihydroxyfluorene to p-nitrobenzoyl chloride is 1:2~2.2, after the dropwise addition, react at room temperature for 1~5 hours, heat to reflux, reaction time 10~24 hours, rotary evaporation Remove the organic solvent, then wash with water, methanol or ethanol, filter, and vacuum-dry to obtain dinitrofluorene containing ester groups;

[0020] The second ...

Embodiment 1

[0028] Synthesis of 9,9-bis(4-nitrobenzoic acid methyl)fluorene

[0029] Into a container equipped with a stirrer, a condenser, and a thermometer, add anhydrous chloroform 50mL, 9,9-bishydroxymethylfluorene 4.52g and triethylamine 50mL in sequence at 2 to 4°C, and then add dropwise at a concentration of 20g / L p-nitrobenzoyl chloride chloroform solution 375mL, after dropwise addition, react at room temperature for 3 hours, and at reflux temperature for 16 hours, after the reaction is over, distill off chloroform and triethylamine under reduced pressure, then wash with water, Wash with methanol or ethanol, filter, and vacuum-dry to obtain light yellow 9,9-bis(4-nitrobenzoic acid methyl)fluorene with a yield of 90%.

[0030] Proton NMR spectrum test result (500M, CDCl 3 , ppm): 7.35~7.84 (16H, Ar-H), 4.80 (4H, -CH 2 -). Infrared spectrum test results (KBr, cm -1): 2942 and 2833 are C-H stretching vibrations, 1740 shows typical carboxylate C=O stretching vibrations, 1601, 150...

Embodiment 2

[0032] Except the raw material 9,9-bishydroxymethyl fluorene was changed to 9,9-bis hydroxybutyl fluorene, the dosage was 6.2g, anhydrous chloroform was changed to dioxane, and the concentration of p-nitrobenzoyl chloride dioxane solution was It is 40g / L, and consumption is 190mL, other conditions are the same as embodiment 1, finally obtain light yellow 9,9-bis(4-nitrobenzoic acid butyl) fluorene, yield 85%.

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Abstract

The invention provides 2-amino-fluorene containing an ester group and a preparation method thereof. The preparation method includes reacting 2-hydroxy-fluorene with p-nitrobenzoyl chloride at a room temperature for 1-5 hours, wherein the mass ratio of the 2-hydroxy-fluorene and the p-nitrobenzoyl chloride is 1:(2-2.2), subjecting the mixture to a reaction under a reflux condition for 10-24 hours to obtain 2-nitrofluorene containing the easter group; and subjecting the 2-nitrofluorene containing the easter group to reduction through hydrazine hydrate to obtain the white 2-amino-fluorene containing the ester group in the presence of a catalyst for 24-60 hours of reflux reaction, wherein the mass ratio of the 2-nitrofluorene containing the easter group and the hydrazine hydrate is 1:(3.2-4.8). According to the 2-amino-fluorene containing the ester group, flexibility of molecules is improved while thermal performance cannot be reduced greatly due to the induction of the ester group; and the 2-amino-fluorene containing the ester group can serve as a raw material for a curing agent for epoxy resin, polyimide and benzoxazine.

Description

technical field [0001] The invention relates to an organic polymer material, and also relates to a preparation method of the organic polymer material. Specifically, it is an ester group-containing diaminofluorene and a preparation method thereof. Background technique [0002] With the rapid development of aerospace, transportation, information transmission, household appliances and other technical fields, people's requirements for polymer materials are also getting higher and higher. Excellent mechanical properties, heat resistance, weather resistance and electrical insulation have become the goals pursued by people. At the same time, people's research on polymer materials is constantly developing in the direction of lightweight, low cost, high performance and multifunctionality, and the key to achieving this goal requires high-performance resins with different structures. To be done. The development of high-performance resins can be attributed to three aspects: heat resi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C229/60C07C227/04
Inventor 刘文彬李新王军何轩宇白建伟韩丽李悦刘珺婷
Owner HARBIN ENG UNIV
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