Preparation method of side chain type imidazolyl benzdine

A technology of imidazole-based benzidine and hydroxybenzidine, which is applied in the field of preparation of aromatic diamine monomers, can solve the problem of poor hydrolytic stability of sulfonated polyimide, few varieties of imidazole-based diamine monomers, and restrictions on imidazole-based Polymer development and other issues to achieve the effect of improving polymer performance and enriching types

Active Publication Date: 2013-07-17
上海东赤电子科技有限公司
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  • Abstract
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Problems solved by technology

[0005] Due to the lack of varieties of imidazole-based diamine monomers, there are fewer varieties of imidazole-based polymers, which seriously restricts the development of imidazole-based polymers, and the relevant research results (Zhang Guimei, master's degree thesis of Shanghai Jiaotong University; Xu Nan, Shanghai Jiaotong University doctoral dissertation) showed that the hydrolytic stability of the sulfonated polyimide prepared from the above-mentioned commercially available imidazole-based diamine-containing monomer (A) was poor

Method used

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  • Preparation method of side chain type imidazolyl benzdine
  • Preparation method of side chain type imidazolyl benzdine
  • Preparation method of side chain type imidazolyl benzdine

Examples

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Embodiment 1

[0032] Synthesis of 2,2'-bis(4-(1H-benzimidazol-2-yl)phenoxy)benzidine

[0033] (1) Under nitrogen protection, add 2.16g (0.010mol) of 2,2'-dihydroxybenzidine and 2.42g (0.020mol) of p-fluorobenzidine into a 100mL three-necked flask equipped with a water separator and fully dried Cyanide, 3.50g (0.025mol) potassium carbonate, 15mL N,N-dimethylacetamide, stir evenly and heat to 140°C, slowly add 10mL toluene dropwise with a constant pressure dropping funnel, react at this temperature for 4 hours and The toluene and water were distilled off completely. Then the temperature was raised to 150° C. for 20 hours of reaction. After the reaction, the system was cooled to room temperature and poured into deionized water. A large amount of reddish-brown solids were precipitated. Filtered with suction to collect the filter cake. The filter cake was washed repeatedly with deionized water and vacuum-dried at 60°C for 12 hours to obtain a reddish-brown solid. , and the yield was 85%.

[0...

Embodiment 2

[0040] Preparation of Side Chain Type Imidazolyl Sulfonated Polyimide Proton Exchange Membrane

[0041] (1) Under nitrogen protection, add 0.9504g (1.8mmol) of 4,4'-bis(4-aminophenoxy)biphenyl-3,3'-disulfonic acid ( BAPBDS), 0.1200g (0.2mmol) 2,2'-bis(4-(1H-benzimidazol-2-yl)phenoxy)benzidine, add 0.7mL triethylamine, 15mL m-cresol, stir to make The solid dissolves. After the solid is completely dissolved, add 0.5360g (2mmol) of 1,4,5,8-naphthalene tetracarboxylic dianhydride (NTDA), 0.4884g of benzoic acid, react at 80°C for 8 hours, and then heat up to 180°C React for 20 hours. The system was cooled to room temperature, poured into 150 mL of methanol to obtain a reddish-brown fibrous solid, which was filtered with suction, and the solid was dried in vacuum at 60°C.

[0042] (2) Add 0.5 g of the polymer synthesized in step (1) to a 25 mL Erlenmeyer flask, and add 10 mL of m-cresol to dissolve it completely. Filter, cast the filtrate on a glass plate, and dry it at 110°C f...

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Abstract

The invention discloses a side chain type imidazolyl benzdine and a preparation method thereof. The preparation method comprises the following steps of: utilizing 3, 3'-dihydroxydiphenylamine as a raw material, carrying out three reaction steps of etherification grafting, acidification hydrolyzing and condensation cyclizing, and thus obtaining the side chain type imidazolyl benzdine. An imidazole group of a diamine monomer is grafted with a side chain which is far from a main chain, so that the performance of a polymer can be effectively improved, and particularly, the anti-radical oxidation stability and hydrolytic stability of sulfonated polyimide are improved. The side chain type imidazolyl benzdine can also be served as the raw material for synthesizing polymers such as polyimide, polyamide, polyurethane, polyether amine and the like, and has a wide application prospect on the aspects of high-performance fibers and fuel cells.

Description

technical field [0001] The invention relates to a preparation method of an aromatic diamine monomer, in particular to a preparation method of a side chain imidazolyl benzidine monomer. Background technique [0002] Aromatic diamines containing imidazole groups are an important class of functional monomers, which are used in the preparation of high-performance polymers such as polyimides and polyamides. The Chinese invention patent with publication number CN101200822A reports that imidazole-containing polyimide fibers have higher mechanical properties and heat resistance than corresponding imidazole-free polyimide fibers. Document J.Membr.Sci.2009, 326, 708-713 reported that the introduction of imidazole groups into the structure of sulfonated polyimide can significantly improve the free radical oxidation resistance of proton exchange membranes. In addition, imidazole groups, as a type of functional group, can endow polymers with more special properties, such as flame retard...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/12C08G73/10H01M2/16
CPCY02E60/10
Inventor 房建华李威郭晓霞
Owner 上海东赤电子科技有限公司
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