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Aromatic diamine monomer and preparation method thereof

A technology of aromatic diamine and monomer, which is applied in the field of diamine monomer and its preparation, can solve the problems that hinder the pace of research and development of aramid fiber, the damage of fiber performance, broken filaments and wool, etc., and achieve improvement Overall performance, simplification of the dissolution process, and the effect of particles that are not easily gelled

Inactive Publication Date: 2016-06-08
DONGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it has been found through experiments that the polymerization product produces a large amount of gel in the spinning process, which is easy to cause blockage, broken filaments and wool.
This will greatly damage the performance of the fiber, and due to poor compatibility with the reaction system, it will greatly damage the original performance, thus seriously hindering the pace of domestic aramid fiber research and development.

Method used

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  • Aromatic diamine monomer and preparation method thereof
  • Aromatic diamine monomer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Add 2-chloro-4-nitroaniline (51.9g, 0.3mol), pyridine (23.7g, 0.3mol) and tetrahydrofuran (215ml) in the three-necked round-bottomed flask, then use the dropping funnel to slowly drop the solution dissolved in tetrahydrofuran ( Terephthaloyl chloride (20.3g, 0.1mol) in 108ml), the rate of addition was 120ml / h, and heated at 25°C for 12h. After the reaction, the solid was filtered and washed three times with water and acetone. Drying under low temperature gave a yellow solid which was the nitro compound (43 g, 90.5%). Under the protection of argon (three deoxygenation), add ethanol (280ml) palladium carbon (0.53g) to the nitro compound (23.8g, 0.05mol), react at 80°C for 8 hours under hydrogen, and filter after the reaction The crude product was obtained, and then separated by column chromatography (the eluent was dichloromethane / ethyl acetate with a volume ratio of 2:1) to obtain a light green solid that was N,N'-bis(4-amino-2-chloro phenyl) terephthalamide.

Embodiment 2

[0026] Add 2-chloro-4-nitroaniline (60.6g, 0.35mol), pyridine (23.7g, 0.3mol) (26.1g, 0.33mol) and tetrahydrofuran (215ml) in the three-necked round bottom flask, then use the dropping funnel Slowly add terephthaloyl chloride (20.3g, 0.1mol) dissolved in tetrahydrofuran (108ml) dropwise at a rate of 120ml / h, heat at 25°C for 12h, and filter to obtain a solid after the reaction, then water and Washed three times with acetone and dried under vacuum to obtain a yellow solid which is the nitro compound (43 g, 90.5%). Under the protection of argon (three deoxygenation), add ethanol (280ml) palladium carbon (0.53g) to the nitro compound (23.8g, 0.05mol), react at 100°C for 8 hours under hydrogen, and filter after the reaction The crude product was obtained, and then separated by column chromatography (the eluent was dichloromethane / ethyl acetate with a volume ratio of 2:1) to obtain a light green solid that was N,N'-bis(4-amino-2-chloro phenyl) terephthalamide.

Embodiment 3

[0028] Add 2-chloro-4-nitroaniline (69.2g, 0.4mol), pyridine (23.7g, 0.3mol) and tetrahydrofuran (215ml) in the three-neck round-bottomed flask, then use the dropping funnel to slowly drop the solution in tetrahydrofuran ( Terephthaloyl chloride (20.3g, 0.1mol) in 108ml), the rate of addition is 120ml / h, heated at 25°C for 12h, filtered to obtain a solid after the reaction, and then washed three times with water and acetone, and the Drying under low temperature gave a yellow solid which was the nitro compound (43 g, 90.5%). Under argon protection (three deoxygenation), add ethanol (280) palladium carbon (0.53g) in the nitro compound (23.8g, 0.05mol), under hydrogen condition, react at 100 ℃ for 8 hours, and the reaction ends After filtration, the crude product was obtained, and then separated by column chromatography (the eluent was dichloromethane / ethyl acetate with a volume ratio of 2:1) to obtain a light green solid that was N,N'-bis(4-amino-2 -chlorophenyl) terephthalamid...

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Abstract

The invention relates to an aromatic diamine monomer and a preparation method thereof. The aromatic diamine monomer is N,N'-bis(4-amino-2-chlorphenyl) terephthalamide and has a structural formula shown in the specification. The preparation method comprises steps as follows: 2-chloro-4-nitroaniline, alkali and tetrahydrofuran are mixed, a tetrahydrofuran solution of paraphthaloyl chloride is dropwise added, the mixture reacts for 8-12 h at the temperature of 25-35 DEG C, N,N'-bis(2-chloro-4-nitrobenzene) terephthalamide is obtained, ethanol and Pd / C are added to N,N'-bis(2-chloro-4-nitrobenzene) terephthalamide under the protection of argon, the mixture reacts for 5-12 h at the temperature of 80-100 DEG C under the protection of hydrogen, and the aromatic diamine monomer is obtained. The aromatic diamine monomer is simple in structure, has good development prospect and is an important constituent part for PPTA (poly(p-phenylene terephthalamide)) copolycondensation modification in the future. The preparation method is simple, and the yield is high.

Description

technical field [0001] The invention belongs to the field of diamine monomer and its preparation, in particular to an aromatic diamine monomer and its preparation method. Background technique [0002] Polyamide materials, as high-performance materials, have received full attention from countries all over the world, and play an important role in national construction and national defense construction. Among them, the representative poly-paraphenyleneterephthalamide (PPTA) fiber is called para-aramid fiber or aramid fiber 1414 in China, because aramid fiber has ultra-high modulus and high strength , high temperature resistance, light weight and other characteristics, so it has a wide range of applications in aerospace, military clothing, material reinforcement and other fields. However, due to the high rigidity of PPTA molecular chains, strong hydrogen bonds between molecular chains, tight packing and high crystallization of molecular chains, the melting point of PPTA resin i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/02C07C233/66C07C231/12C07C233/80C08G69/32D01F6/80
CPCC07C233/80C07C231/02C07C231/12C08G69/32D01F6/805
Inventor 余木火秦明林滕翠青李会张康刘百花刘静孔海娟余凡顾灏杨鹏
Owner DONGHUA UNIV
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