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Phenylenediamine monomer containing 1,4:3,6-dianhydro hexitol pendant group and preparation and application thereof

A technology of dianhydrohexitol and phenylenediamine, applied in ultrafiltration, organic chemistry, membrane technology and other directions, can solve the problems of hydrophobicity and easy pollution of separation membrane, and achieve the effects of abundant raw materials, low price and improved solubility

Active Publication Date: 2018-01-12
JILIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The technical problem to be solved by the present invention is that the separation membrane prepared by the existing polyethersulfone resin material has the problems of hydrophobicity and easy pollution in application.

Method used

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  • Phenylenediamine monomer containing 1,4:3,6-dianhydro hexitol pendant group and preparation and application thereof
  • Phenylenediamine monomer containing 1,4:3,6-dianhydro hexitol pendant group and preparation and application thereof
  • Phenylenediamine monomer containing 1,4:3,6-dianhydro hexitol pendant group and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] (1) Under normal temperature and pressure, add 20mmol 3,5-dinitrobenzoyl chloride, 200mmol isomannitol and 2mmol15-crown-5 into a three-neck round bottom flask equipped with a mechanical stirrer, a condenser and a thermometer , heated to 60°C to melt and continue to stir for 20 minutes; add 100mL N,N-dimethylformamide to the system and stir rapidly, cool to room temperature, the product precipitates after 60 minutes, filter with suction, and the precipitated solid is deionized Washed with water for 5 times, dried at 80°C for 10 hours, and recrystallized with methanol to obtain 18.5 mmol light yellow benzenedinitromonomer containing 1:4; 3:6-dianhydrohexitol structure: 2-hydroxy-5 -(3,5-Dinitrobenzoyl)isomannitol;

[0030] (2) 10mmol 2-hydroxyl-5-(3,5-dinitrobenzoyl) isomannitol was dissolved in 30mmol ethanol, and under nitrogen protection, 2mmol mass fraction of 10% palladium carbon was added, and the temperature was raised To reflux, add 100mmol hydrazine hydrate dro...

Embodiment 2

[0033] (1) under normal temperature and pressure, 20mmol 3,5-dinitrobenzoyl chloride, 40mmol isosorbide and 2mmol 18-crown-6 were added in a three-neck round bottom flask equipped with a mechanical stirrer, a condenser and a thermometer, Heat to 60°C to melt and continue to stir for 10 minutes; add 100mL N,N-dimethylacetamide to the system and stir rapidly, cool to room temperature, the product precipitates after 20 minutes, filter with suction, and wash the precipitated solid with deionized water Washed 3 times, dried at 80°C for 10 hours, and recrystallized with methanol to obtain 18 mmol light yellow benzenedinitromonomer containing 1:4; 3:6-dianhydrohexitol structure: 2-hydroxyl-5-( 3,5-Dinitrobenzoyl) isosorbide;

[0034] (2) Dissolve 10 mmol 2-hydroxy-5-(3,5-dinitrobenzoyl) isosorbide in 12 mmol 1,4-dioxane, and add 2 mmol mass fraction of 10 % palladium carbon, warming up to reflux, drop 20mmol hydrazine hydrate at a rate of 0.20mL / min with a constant pressure dropping...

Embodiment 3

[0036] (1) Under normal temperature and pressure, add 20mmol 3,5-dinitrobenzoyl chloride, 100mmol iditol and 2mmol cyclodextrin into a three-necked round-bottomed flask equipped with a mechanical stirrer, a condenser and a thermometer, Heat to 60°C to melt and continue to stir for 15 minutes; add 100mL N-methylpyrrolidone to the system and stir rapidly, cool to room temperature, the product precipitates after 120 minutes, suction filter, and the precipitated solid is washed 4 times with deionized water, After drying at 80°C for 10 hours, recrystallize with methanol to obtain 17 mmol light yellow benzene dinitro monomer containing 1:4; 3:6-dianhydrohexitol structure, namely 2-hydroxyl-5-(3,5 - dinitrobenzoyl) iditol;

[0037] (2) 10mmol 2-hydroxyl-5-(3,5-dinitrobenzoyl) iditol was dissolved in 15mmol methanol, and under nitrogen protection, 2mmol mass fraction of 10% palladium carbon was added, and the temperature was raised To reflux, add 50mmol hydrazine hydrate dropwise at ...

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Abstract

The invention discloses a phenylenediamine monomer containing a 1,4:3,6-dianhydro hexitol structure and preparation and application thereof, and belongs to the technical field of polymer synthesis. The invention provides the phenylenediamine monomer containing a 1,4:3,6-dianhydro hexitol structure and the preparation and the application thereof. 3,5-dinitrobenzoyl chloride and 1,4:3,6-dianhydro hexitol react through a solvent-free fusion method to prepare a benzene binitro monomer containing the 1,4:3,6-dianhydro structure; after reduction, the phenylenediamine monomer containing the 1,4:3,6-dianhydro hexitol structure is obtained; the phenylenediamine monomer containing the 1,4:3,6-dianhydro hexitol structure and a diacid monomer can be prepared into polyamide containing the 1,4:3,6-dianhydro hexitol through polycondensation, and the polyamide containing the 1,4:3,6-dianhydro hexitol and polyether sulfone are doped to prepare a polyether sulfone hybridized ultrafiltration membrane. According to the polyamide containing the 1,4:3,6-dianhydro hexitol, the hydrophilia, the water flux and the pollution resistance of the polyether sulfone ultrafiltration membrane are obviously improved.

Description

technical field [0001] The invention relates to the field of polymer synthesis, in particular to a phenylenediamine monomer containing 1,4:3,6-dianhydrohexitol side groups for improving the hydrophilicity and antifouling properties of polyethersulfone resins and its Preparation and application. Background technique [0002] Due to the advantages of high efficiency, low cost, good selectivity and no phase change, membrane technology is widely used in food, pharmaceutical, biotechnology and water treatment and other fields. In recent years, polyethersulfone resin has been prepared into ultrafiltration membranes and used in industrial water treatment due to its good thermal properties, acid and alkali resistance, high mechanical properties and good film-forming properties. However, due to the strong hydrophobicity of the polyethersulfone resin membrane, the organic or inorganic substances often contained in the wastewater are easily adsorbed or deposited on the membrane surfac...

Claims

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Application Information

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IPC IPC(8): C07D493/04B01D61/14B01D71/68B01D69/02C08G69/32
Inventor 陈春海刘志晓米智明周宏伟赵晓刚王大明
Owner JILIN UNIV