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High-molecular-weight furyl aromatic polyamide, preparation method and application thereof

A furan-based aromatic polyamide, high molecular weight technology, applied in the direction of one-component polyamide rayon, one-component synthetic polymer rayon, wet spinning, etc. The mechanical properties and mechanical properties of the amide product have no problems such as actually obtaining polymers, and achieve excellent thermodynamic properties and mechanical properties, simple process, and mild reaction conditions.

Active Publication Date: 2019-09-20
UNIV OF SCI & TECH OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, wherein the basic monomers used to obtain the furan-based polyamide polymer are furandicarboxylic acid or its derivatives and m-phenylenediamine, and although it is mentioned that the molecular weight of the obtained furan-based polyamide polymer may be very high, However, the highest weight-average molecular weight of the polymer actually synthesized in the examples is also in the lower range of tens of thousands to hundreds of thousands, and no polymer with a molecular weight higher than 200,000 is actually obtained.
And, in fact, as can be seen from Example 2 of this document, in the method for synthesizing the furan-based polyamide polymer of its high weight-average molecular weight (being 100994g / mol), it is also necessary to use inorganic metal salts such as LiCl as a catalyst to Therefore, it also has the same problem as above, that is, inorganic metal salts such as LiCl are difficult to completely remove in the reaction system, and the residual inorganic salts will reduce the mechanical properties and mechanical properties of the polyamide product.

Method used

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  • High-molecular-weight furyl aromatic polyamide, preparation method and application thereof
  • High-molecular-weight furyl aromatic polyamide, preparation method and application thereof
  • High-molecular-weight furyl aromatic polyamide, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0079] Embodiment 1: the high molecular weight furyl polyamide of preparation formula (III)

[0080] In an argon-protected glove box, 100 ml of N-methylpyrrolidone was added to a 250-ml three-necked round-bottomed flask equipped with a mechanical stirrer, an argon inlet, and an addition port, and stirred under mechanical stirring in an argon atmosphere. 20 g of 2,5-furandicarboxylic acid chloride were added. Then, the temperature was controlled by a water bath at a temperature of 20° C., and 20.8 g of 4,4-diaminodiphenyl ether was added under stirring, and 0.8 g of 2-(7-benzotriazole oxide)-N , N, N', N'-tetramethyluronium hexafluorophosphate, after continuing to stir for 5 hours, the reaction was terminated.

[0081] figure 1 The proton nuclear magnetic resonance spectrum of the furanyl aromatic polyamide polymer obtained according to the present embodiment 1 is shown, by figure 1 It was confirmed that the obtained polymer was a furyl aromatic polyamide polymer obtained by...

Embodiment 2

[0082] Embodiment 2: the high molecular weight furyl polyamide of preparation formula (IV)

[0083] In an argon-protected glove box, 100 ml of N-methylpyrrolidone was added to a 250-ml three-necked round-bottomed flask equipped with a mechanical stirrer, an argon inlet, and an addition port, and stirred under mechanical stirring in an argon atmosphere. 10 g of 2,5-furandicarboxylic acid chloride and 8.6 g of terephthalic acid were added. Then, the temperature was controlled by a water bath at a temperature of 20° C., and 10.4 g of 4,4-diaminodiphenyl ether and 11.25 g of p-phenylenediamine were added under stirring, while 0.8 g of 2-(7-phenylene oxide was added. and triazole)-N, N, N', N'-tetramethyluronium hexafluorophosphate, and continued stirring for 5 hours. After the reaction, sampling and analysis by gel permeation chromatography (GPC) instrument showed that the number average molecular weight of the obtained furyl polyamide was 321255, and the molecular weight distrib...

Embodiment 3

[0084] Embodiment 3: the high molecular weight furyl polyamide of preparation formula (V)

[0085] In an argon-protected glove box, 100 ml of N-methylpyrrolidone was added to a 250-ml three-necked round-bottomed flask equipped with a mechanical stirrer, an argon inlet, and an addition port, and stirred under mechanical stirring in an argon atmosphere. 20 g of 2,5-furandicarboxylic acid chloride were added. Then, the temperature was controlled by a water bath at a temperature of 20° C., and 10.4 g of 4,4-diaminodiphenyl ether and 11.25 g of p-phenylenediamine were added under stirring, and 0.8 g of 2-(7-benzoxyl oxide was added. Triazole)-N, N, N', N'-tetramethyluronium hexafluorophosphate, continued to stir and react for 5 hours. After the reaction was finished, the number average molecular weight of the obtained furanyl polyamide was 293768, and the molecular weight distribution coefficient was 1.50.

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Abstract

The present invention relates to a high molecular weight furyl aromatic polyamide derived from a diacid monomer, comprising a substituted or unsubstituted furandicarboxylic acid or a derivative thereof, and a diamine monomer comprising a substituted or unsubstituted 4,4'-diaminodiphenyl ether or a derivative thereof, and comprising a repeating unit having the following formula (I); wherein R1 to R10 are each independently H or a C1-C6 alkyl group. The method is mild in preparation condition and simple in process. The high molecular weight furan-based aromatic polyamide has excellent thermodynamic properties and mechanical properties, and can be applied to preparation of fibers, membrane materials and nanoparticle / polymer composite materials.

Description

technical field [0001] The invention belongs to the field of polyamide and its preparation, and in particular relates to a high-molecular-weight furyl aromatic polyamide and its preparation method and application. Background technique [0002] Polyamide has outstanding advantages such as excellent mechanical properties, good self-lubrication and friction resistance, high heat resistance temperature, and high electrical insulation. It is widely used in machinery, automobiles, electrical appliances, textile equipment, chemical equipment, aviation, metallurgy and other fields. It is a bulk engineering plastic, which is of great significance to national economy, social development and national defense security. With the development of society, the demand for polyamide compounds continues to grow rapidly. [0003] Compared with petroleum-based polyamides, the monomer 2,5-furandicarboxylic acid of furan-based polyamides is produced from biomass derived from renewable resources, a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G69/40D01F6/60C08J5/18C08L77/06
CPCC08G69/40D01F6/60C08J5/18C08L77/06C08J2377/06D01F6/82D01D5/06C08G69/265C08G69/32C08L77/10C08L2203/12C08G69/28C08L2203/16
Inventor 傅尧李锋高敬民朱俊盛天然李兴龙付明臣
Owner UNIV OF SCI & TECH OF CHINA
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