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Side-chain modified dianhydride intermediate containing biphenyl structure and preparation method and application thereof

A biphenyl structure and intermediate technology, which is applied in the field of polymer material preparation, can solve the problems of low yield of dianhydride intermediates and increased reaction costs, and achieve the effects of improving processing performance and increasing solubility

Inactive Publication Date: 2011-10-19
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] This method solves the contradiction between high strength, high modulus, high heat resistance, high dimensional stability and polyimide processability to a certain extent, but the yield of the dianhydride intermediate of this synthesis is very low, Less than 20%
In addition, due to the introduction of palladium carbon as a coupling catalyst, the reaction cost is greatly increased [Lin SH, Li F, Cheng SZD, Harris FW. Macromolecules1998; 31: 2080]

Method used

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  • Side-chain modified dianhydride intermediate containing biphenyl structure and preparation method and application thereof
  • Side-chain modified dianhydride intermediate containing biphenyl structure and preparation method and application thereof
  • Side-chain modified dianhydride intermediate containing biphenyl structure and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Example 1 Preparation of 2-methoxy-4,4',5,5'-biphenyltetraacid dianhydride monomer

[0051]Add 1 part (0.015mol) of sodium metal and 12 parts (0.125mol) of methanol into a three-necked flask with a mechanical stirrer and a thermometer, stir the reaction at a temperature of 0°C for 1h, then remove residual methanol by distillation, and add 29 parts (0.027mol) 2-nitro 4,4',5,5'-biphenylimide, 58 parts (0.2mol) of N-methylpyrrolidone (NMP), heated to 40°C and stirred for 2 hours. The reaction solution was poured into tap water to precipitate, and the filter cake was obtained by suction filtration, and the filter cake was washed with water until neutral. After the filter cake was air-dried, 2-methoxy 4,4',5,5'-biphenylimide was obtained. Add 15 parts (0.017mol) of 2-methoxy 4,4',5,5'-biphenylimide, 36 parts (0.26mol) of KOH and 49 parts (1.1mol) of distilled water into a single-necked bottle, heat Reaction at 100°C for 12h. Use concentrated hydrochloric acid to adjust th...

Embodiment 2

[0052] Example 2 Preparation of 2-styryl acid ester-4,4',5,5'-biphenyltetraacid dianhydride

[0053] 8 parts (0.064mol) of 2-nitro 4,4',5,5'-biphenylimide monomer, 87 parts (3.42mol) of N,N-dimethylformamide (DMF), 3 parts (0.064mol) of anhydrous potassium carbonate and 2 parts (0.064mol) of sodium nitrite were sequentially added into a three-necked bottle with a stirring device and a thermometer, and reacted at a temperature of 130° C. for 12 hours under a nitrogen atmosphere. The pH of the reaction solution was adjusted to 1 with concentrated hydrochloric acid. Stir well, a large amount of yellow precipitate appears, the precipitate is suction filtered, washed with water and air-dried to obtain 2-hydroxyl 4,4',5,5'-biphenylimide. Add 15 parts (0.045mol) of 2-hydroxyl 4,4',5,5'-biphenylimide, 36 parts (0.65mol) of KOH and 49 parts (2.7mol) of distilled water into a single-necked bottle and heat to 100°C Reaction 12h. Use concentrated hydrochloric acid to adjust the pH of t...

Embodiment 3

[0054] Example 3 Preparation of 2,2'-p-tert-butylphenylsulfide-4,4',5,5'-biphenyltetraacid dianhydride

[0055] With 20 parts (50.0mmol) p-tert-butylthiophenol, 5 parts (50.0mmol) sodium hydroxide, 25 parts (0.12mol) N, N-dimethylacetamide (DMAc) and 25 parts (0.11mol) Toluene was sequentially added to a three-necked flask equipped with a stirrer, a thermometer and a reflux condenser. Under the protection of nitrogen, react at room temperature for 1 hour, then raise the temperature to 130°C for reflux for 3 hours, and cool the reaction to 80°C after water and toluene are separated. Add 25 parts (25.0 mmol) of 2,2'-dinitro-4,4',5,5'-biphenylimide, react at a temperature of 80°C for 2 hours, cool the reaction solution and pour it into water for precipitation. The product 2,2'-p-tert-butylphenylsulfide-4,4',5,5'-biphenylimide was obtained. 27 parts (0.024mol) of 2,2'-p-tert-butylphenylsulfide-4,4',5,5'-biphenylimide, 28 parts (0.28mol) of KOH and 45 parts (1.38mol) Distilled w...

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Abstract

The invention discloses a side-chain modified dianhydride intermediate containing biphenyl structure and a preparation method and applications thereof. The invention is characterized in that the method comprises the following steps of: reacting dibenzoyl imine compounds with nitric acids of different mol ratios to obtain dinitrated and mononitrated products, conducting nucleophilic substitution with compounds containing alcohol or phenol in different structures, and then conducting acidification ring-closure reaction to obtain the side-chain modified dianhydride intermediate containing biphenyl structure. The side-chain modified dianhydride intermediate containing biphenyl structure and different diamines can be polymerized into various kinds of functional polyimide by using a one-step method or two-step method. Modified groups are introduced to a side chain by using the method, so that the dissolubility and the meltability of the polyimide are raised, the processability of polyimide materials is effectively improved, and new functions and applications are given to polyimide materials.

Description

technical field [0001] The invention relates to a side-chain modified dianhydride intermediate containing a biphenyl structure, a preparation method and application thereof, and belongs to the field of preparation of polymer materials. Background technique [0002] Polyimide (PI) is a high-performance polymer containing imide rings in the main chain. Due to the excellent thermal stability, mechanical properties, chemical inertness, dielectric properties and radiation resistance of aromatic polyimides, Much of the current research focuses on this. Among them, polyimides with 3,3',4,4'-biphenyl structures are superior to ordinary fully aromatic polyimides in terms of heat resistance, mechanical properties, hydrolysis resistance, and flexibility. It is the variety with the highest heat resistance among polyimides that have been industrialized so far. Such as: [0003] [0004] Because of its outstanding strength, wear resistance, excellent shape and industrial stability a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/89C08G73/10
Inventor 杨刚郭乔曾科武迪蒙
Owner SICHUAN UNIV