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Norbornene imide heat-resistant polymer porous material and preparation method thereof

A technology of bornene imide and porous materials, applied in the field of materials, can solve the problems of high price, poor stability of polyamide carboxylic acid, and limited types of dibasic acid anhydrides

Inactive Publication Date: 2015-09-02
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, polyimide materials are usually prepared by a two-step method of diamine and dibasic acid anhydride, which has some disadvantages: (1). The types of dibasic anhydrides are limited, and the price is relatively expensive; (2). The resulting polyamide Carboxylic acid has poor stability and needs to be stored at low temperature; (3). The imidization temperature is relatively high, usually above 300°C, such a high operating temperature is likely to cause product decomposition, etc.
The design of this type of material utilizes the rigidity of polyamines and dibasic anhydrides to ensure the maintenance of permanent pores, but the synthesis method still has the shortcomings of traditional polyimide materials.

Method used

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  • Norbornene imide heat-resistant polymer porous material and preparation method thereof
  • Norbornene imide heat-resistant polymer porous material and preparation method thereof
  • Norbornene imide heat-resistant polymer porous material and preparation method thereof

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[0038] The invention provides a kind of heat-resistant polymer porous material of norbornene imide and a preparation method thereof. The method comprises two steps: 1. The norbornene imide monomer is prepared by reacting the norbornene anhydride with polyamine compounds; Polymerization reaction, the obtained polymer is washed with a solvent and then dried to obtain a heat-resistant polymer porous material. The present invention utilizes the tension-containing five-membered ring in norbornene and its analogs to easily carry out ring-opening metathesis polymerization reaction under the action of Grubbs catalyst, and the rigidity and non-planar configuration of the pentapentafused ring structure in the reaction product, And the double bond has the characteristics of inhibiting rotation, and introduces a rigid structure, thereby generating non-close packing to ensure the existence of permanent holes. At the same time, the polymerization reaction conditions are relatively mild, an...

Embodiment 1

[0054] Example 1: Hydrazine hydrate linked norbornene imide monomer II(a)

[0055]

[0056] Add hydrazine hydrate IV (a) (400mg, 4mmol, 1eq, 50%) dropwise to the toluene suspension of NA acid anhydride V(a) (656.64mg, 4mmol, 1eq), stir at room temperature for 20min, TLC shows that the reaction is complete, stop reaction. The solvent was removed under reduced pressure, and the resulting solid product was recrystallized from ethanol to obtain white needle-like crystals, namely NA hydrazide III(a) (581 mg, yield 82%). Rf: 0.26 [V(EtOAc) / V(Petroleum Ether)=2 / 0.5 (2 drops of acetic acid)]; 1 H-NMR (400MHz, CDCl 3 )δ (ppm): 6.09 (s, 2H), 4.12 (s, 2H), 3.38 (s, 2H), 3.24 (s, 2H), 1.75 (d, 1H, J=8.8Hz), 1.54 (d, 1H, J=8.8Hz). The NA hydrazide III (a) (448.3mg, 2.52mmol, 1eq) and NA acid anhydride V (a) (413.7mg, 2.52mmol, 1eq) were added to the acetic acid solvent, heated to reflux for 10h, stopped the reaction, and removed under reduced pressure Acetic acid, the obtained soli...

Embodiment 2

[0062] Example 2: p-Phenylenediamine linked norbornene imide monomer II(b)

[0063]

[0064] NA anhydride V(a) (164.16mg, 1mmol, 1eq) was dissolved in DMF (15ml), p-phenylenediamine (54mg, 0.5mmol, 0.5eq) and triethylamine (101mg, 1mmol, 1eq) were added The reaction system was reacted at 80°C for 2h. After the reaction, the mixture was poured into water, filtered to obtain a solid powder, and recrystallized from acetonitrile to obtain a white solid (184 mg, yield 92%).

[0065] Figure 5 , Figure 6 with Figure 7 Respectively be the proton nuclear magnetic resonance spectrum of II (a) in the embodiment 2, the carbon nuclear magnetic resonance spectrum and the infrared spectrogram.

[0066] H NMR spectrum 1 H NMR (400 MHz, DMSO-d6) δ (ppm): 7.19 (s, 4H), 6.22 (s, 4H), 3.50 (s, 4H), 3.34 (s, 4H), 1.5 (s, 4H).

[0067] C NMR spectrum 13 C-NMR: (100MHz, DMSO-d6) δ (ppm): 176.6, 134.5, 131.9, 127.5, 51.7, 45.4, 44.8.

[0068] Infrared spectrum (KBr, cm -1 ): 2992(w), 2...

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Abstract

The invention provides a norbornene imide heat-resistant polymer porous material and its preparation method. The method comprises the following steps: Step 1, a norbornene imide monomeric compound is prepared from norbornene anhydride and a multi-element organic amine compound by a one-step method or a two-step method, and the norbornene imide monomeric compound is purified; Step 2, the purified product obtained from the step 1 is dissolved in an organic solvent b, temperature is maintained at minus 10-100 DEG C, a Grubbs catalyst is added to carry out a polymerization reaction at the reaction temperature of minus 10-120 DEG C for 5 minutes-2 weeks; and Step 3, aftertreatment is carried out to obtain the heat-resistant polymer porous material.

Description

technical field [0001] The invention relates to the field of material technology, in particular to a heat-resistant polymer porous material of norbornene imide and a preparation method of the heat-resistant polymer porous material of norbornene imide. Background technique [0002] As one of the organic polymer materials with the best comprehensive performance, polyimide material has the widest service temperature range, which can reach -250℃~450℃. This type of material can be used at high temperature for a long time, and it also has excellent flame retardancy, mechanical properties, stability, low dielectric properties, etc., so it is widely used in aerospace, microelectronics, nuclear power and other high-tech field. However, polyimide materials are usually prepared by a two-step method of diamine and dibasic acid anhydride, which has some disadvantages: (1). The types of dibasic anhydrides are limited, and the price is relatively expensive; (2). The resulting polyamide C...

Claims

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Application Information

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IPC IPC(8): C08G61/12C07D209/94C08J9/28
Inventor 黄木华李婷婷罗运军葛震李国平柴春鹏贾瑜珲黑泽峘
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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