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Six-membered ring fragrant trianhydride and preparation method thereof

A six-membered ring and aromatic technology, which is applied in the field of six-membered ring aromatic trianhydrides and its preparation, has achieved wide application prospects and excellent mechanical properties

Active Publication Date: 2011-04-06
SHANGHAI JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since there is only one commercial six-membered ring dianhydride currently required for the synthesis of sulfonated polyimides, different sulfonated polyimides can only be obtained by changing the structure of the diamine, and the six-membered ring di Reaction of anhydrides with sulfonated or non-sulfonated diamines can only produce linear sulfonated polyimides

Method used

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  • Six-membered ring fragrant trianhydride and preparation method thereof
  • Six-membered ring fragrant trianhydride and preparation method thereof
  • Six-membered ring fragrant trianhydride and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0022] In a 100mL three-necked flask equipped with nitrogen inlet, magnetic stirring, water separator and reflux condenser, add 0.6305g (5mmol) 1,3,5-trihydroxybenzene, 15mL methanol, 0.60g (15mmol) sodium hydroxide , heated up to 100°C, evaporated methanol and water, evaporated to dryness, cooled to room temperature, added 4.156 grams (15 mmol) of 4-bromo-1,8-naphthalene anhydride, 16 mL of N-methylacetamide to the reaction flask, and heated To 120°C, drop 15mL of toluene into the reaction system through the dropping funnel, raise the temperature to 140°C, react for 4 hours, distill off the toluene, raise the temperature to 150°C, and continue the reaction for 18 hours. After the reaction, the system is cooled to room temperature. Then the resultant was poured into 150 mL of acetone, and the precipitated solid in the system was washed with water, filtered, and vacuum-dried to obtain 2.87 g of crude product. The obtained crude product was recrystallized with acetic anhydride t...

Embodiment 2

[0027] In a 100mL three-necked flask equipped with nitrogen inlet, magnetic stirring, water separator and reflux condenser, add 0.3783g (3mmol) 1,3,5-trihydroxybenzene, 9mL methanol, 0.36g (9mmol) sodium hydroxide , heated up to 100°C, evaporated methanol and water, evaporated to dryness, cooled to room temperature, added 2.494 g (9 mmol) 4-bromo-1,8-naphthalene anhydride, 6.35 mL N-methylacetamide to the reaction flask, Raise the temperature to 120°C, drop 10mL of toluene into the reaction system through the dropping funnel, raise the temperature to 140°C, react for 4 hours, distill off the toluene, raise the temperature to 150°C, and continue the reaction for 20 hours. After the reaction, the system was cooled to room temperature. Then the resultant was poured into 100 mL of acetone, and the solid precipitated in the system was washed with water, filtered, and vacuum-dried to obtain 1.79 g of a crude product. The obtained crude product was recrystallized with acetic anhydrid...

Embodiment 3

[0029] In a 100mL three-necked flask equipped with nitrogen inlet, magnetic stirring, water separator and reflux condenser, add 0.6305g (5mmol) 1,3,5-trihydroxybenzene, 8mL methanol, 0.60g (15mmol) sodium hydroxide , heated up to 100°C, evaporated methanol and water, evaporated to dryness, cooled to room temperature, added 4.156 grams (15 mmol) of 4-bromo-1,8-naphthalene anhydride, 10 mL of N-methylacetamide to the reaction flask, and heated To 120°C, drop 15mL of toluene into the reaction system through the dropping funnel, raise the temperature to 140°C, react for 4 hours, distill off the toluene, raise the temperature to 150°C, and continue the reaction for 22 hours. After the reaction, the system is cooled to room temperature. Then the resultant was poured into 100 mL of acetone, and the precipitated solid in the system was washed with water, filtered, and vacuum-dried to obtain 2.58 g of crude product. The obtained crude product was recrystallized with acetic anhydride to...

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Abstract

The present invention relates to hexahydric aromatic trianhydride and a preparation method thereof. Under the conditions of protective nitrogen, magnetic stirring and a water separator, trihydroxy compounds, alcohol and alkali are added into a reactor; the mixture is heated to completely distill out the alcohol and water; after the mixture is cooled, halogenated or nitro substituting anhydride naphthalene, organic solvents and azeotropic agents are added; the mixture reacts under the reflux condition; the azeotropic agents and water are distilled; at the temperature, crude aromatic trianhydride can be prepared; the crude aromatic trianhydride is recrystallized by acetic anhydride. The hexahydric aromatic trianhydride is basic material that is used for preparing hyper branched sulfonate ornon-sulfonate polyimide. The hyper branched sulfonate or non-sulfonate polyimide has a terminated functional group that can react and thus can be used for preparing membranes through coupling reaction. Because of the excellent mechanical properties, heat resistance and solvent resistance, the hexahydric aromatic trianhydride has broad application prospects in the proton conductive membrane of fuel batteries, the separation membrane of fuel batteries, the ion exchange membrane in the chlor-alkali industry, and other aspects.

Description

technical field [0001] The invention relates to a six-membered ring aromatic trianhydride and a preparation method thereof. The obtained six-membered ring aromatic trianhydride can be used as a raw material for preparing hyperbranched six-membered ring sulfonated or non-sulfonated polyimide, which belongs to the organic compound technology field. Background technique [0002] Hyperbranched polymers are a class of dendritic macromolecules with a special three-dimensional structure. Compared with traditional linear polymers, hyperbranched polymers have better solubility and lower viscosity, so they have better processing performance. In addition, there are a large number of end groups in hyperbranched polymers, which can be used for further chemical modification. In recent years, sulfonated polymers have attracted much attention due to their application prospects in polymer electrolyte fuel cells, among which six-membered ring sulfonated polyimide has excellent film-forming ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/92C08G73/10
Inventor 郭晓霞张桂梅房建华徐宏杰
Owner SHANGHAI JIAOTONG UNIV
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