Polyimide polymer material based on 2,5-diallyloxy-p-phenylenediamine monomer and preparation method thereof

A diallyloxy-p-phenylenediamine and diallyloxydiamino technology, which is applied in the field of new polyimide polymer materials and their preparation, can solve the trade-off between gas permeability and gas selectivity It can improve the separation performance and plasticization resistance, improve the plasticization resistance and excellent mechanical properties.

Active Publication Date: 2020-11-10
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

After several years of in-depth research and work accumulation, researchers have developed polyimide gas separation membranes with various structures. However, the current research still has shortcomings: (1) gas permeability and gas selectivity are trade-offs, No significant method has been developed to keep both excellent; (2) After long-term use of the separation membrane, plasticization and aging will occur, seriously reducing the performance

Method used

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  • Polyimide polymer material based on 2,5-diallyloxy-p-phenylenediamine monomer and preparation method thereof
  • Polyimide polymer material based on 2,5-diallyloxy-p-phenylenediamine monomer and preparation method thereof
  • Polyimide polymer material based on 2,5-diallyloxy-p-phenylenediamine monomer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] In this embodiment, the novel polyarylimide resin material of allyloxy group has the following repeating structural unit:

[0060]

[0061] The specific preparation method is as follows: when equipped with stirring paddle, drying tube and N 2 Add 50ml of solvent N-methylpyrrolidone and 12.50mmol (2.7500g) of 2,5-diallyloxy-p-phenylenediamine to the three-necked flask at the inlet, stir to dissolve them all, and add 12.50mmol of 6FDA anhydride under ice bath (5.5500g), the mixture was stirred under ice bath for 1h, removed the ice bath, stirred at room temperature for 12h, added Et 3 N and Ac 2 O (1.25ml and 2.50ml), stirred at room temperature for 24h and at 80°C for 3h. The mixture was poured into 700ml of methanol for precipitation, washed three times with methanol and then vacuum-dried at 80°C for 24h to obtain 6.72g of yellow-white polymer ANPI-6FDA with a yield of 86%.

[0062] image 3 The proton nuclear magnetic resonance spectrum of the novel aromatic pol...

Embodiment 2

[0065] In this example, the novel polyarylimide resin material containing hydroxyl and allyl groups has the following repeating structural units:

[0066]

[0067] The specific preparation method is as follows: add 500 mg of the polymer ANPI-6FDA prepared in Example 1 to the polymerization tube, vacuum three times with nitrogen, seal the tube under vacuum conditions, and place it in a 250° C. sand bath for 6-8 hours of reaction. After the reaction was completed, the polymerization tube was broken to obtain 500 mg of the polymer CRNPI-6FDA, with a yield of nearly 100%.

[0068] Figure 4 The proton nuclear magnetic resonance spectrum of the novel aromatic polyimide (CRNPI-6FDA) containing hydroxyl group and allyl group prepared in embodiment 2;

[0069] Figure 4 Among them, the peaks in the spectrum can be well assigned to the molecular structure, and the integral area and the peak position correspond reasonably. After the Claisen rearrangement, the OH peak appears at 9....

Embodiment 3

[0071] In this embodiment, the novel polyarylimide film of allyloxy group has the following repeating structural units:

[0072]

[0073] The specific preparation method is as follows: 1.00 g of ANPI-6FDA polymer is dissolved in 20 ml of dichloromethane, and filtered with a 20 μm polytetrafluoroethylene filter membrane to obtain a clear orange solution. Add the solution dropwise on a clean flat glass to make the solution cover evenly, and slowly evaporate the solvent. After the film is formed, put it in a vacuum oven for heat treatment at 80°C-200°C in stages, take it out, put it in water, and peel it off to obtain a film.

[0074] Figure 5 The ATR-IR spectrum of the allyloxy-containing novel aromatic polyimide film (ANPI-6FDA) prepared in Example 3.

[0075] at 1789 and 1724cm -1 The stretching vibration peak attributed to imide C=O appears at 1625cm -1 The peak is the vibration peak of the benzene ring skeleton. Show above, polymkeric substance has typical polyimide...

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Abstract

The invention discloses a preparation method and application of allyloxy-containing aromatic polyimide. The allyloxy-containing high polymer compound has a repeated structure unit of a formula I shownin the description. According to the preparation method, a diallyloxy diamine monomer is selected as a basic monomer, the basic monomer is copolycondensed with binary aromatic primary amine and quaternary anhydride according to a ratio, and thus a series of novel aromatic polyimide of different contents of allyloxy is prepared. Hydroxyl and allyl can be obtained from a prepared allyloxy-modifiedpolyimide film through claisen rearrangement. Due to the hydroxyl, the separation selectivity of the film upon gases can be improved, and the allyl can be used as a crosslinking reaction site to improve the plastification resistance of the film. Due to the novel molecular structure designing, a new generation of gas separation films with both separation and plastification resistance can be prepared.

Description

technical field [0001] The invention belongs to the field of polymer material synthesis, and in particular relates to a novel polyimide polymer material based on 2,5-diallyloxy-p-phenylenediamine monomer and a preparation method thereof. Background technique [0002] Polyimide refers to a high-performance polymer with a phthalimide structure in the main chain. Its molecular chain does not contain weak chemical bonds, has high rigidity, and requires a high energy barrier for thermal movement, resulting in good mechanical properties, small thermal expansion coefficient, and low hygroscopicity. , The above characteristics endow polyimide with unique application value in the fields of membrane separation, high-performance fiber, composite material matrix, insulating coating and so on. [0003] Recently, the unique properties of polyimide films in gas separation have attracted attention. After several years of in-depth research and work accumulation, researchers have developed p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G73/10C08L79/08C08J5/18
CPCC08G73/1057C08G73/1067C08J5/18C08J2379/08
Inventor 宛新华齐翔章斐张杰
Owner PEKING UNIV
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