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Diamine with novel structure and preparation method and application thereof

A new type of structure, diamine technology, applied in the field of material science, can solve the problems of limited barrier performance and inability to meet the performance requirements of polyimide, achieve high electron density, broad-spectrum antibacterial and antibacterial activities, improve heat resistance and The effect of mechanical properties

Inactive Publication Date: 2020-05-01
HUNAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The improvement of barrier performance by this technology is limited, and it cannot meet the performance requirements of polyimide in the field of high barrier

Method used

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  • Diamine with novel structure and preparation method and application thereof
  • Diamine with novel structure and preparation method and application thereof
  • Diamine with novel structure and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] This example provides the synthesis of 4,4'-(10H-phenoxazine-2,8-diyl)dianiline:

[0037]

[0038] S1. Add 3.41g (0.01mol) 2,8-dibromo-10H-phenoxazine, 4.335g (0.025mol) p-aminophenyl borate hydrochloride into a 500ml three-necked flask, tetrahydrofuran (THF) as the solvent, and then add 2mol / L of potassium carbonate solution 37.5ml and appropriate amount of Aliquat336, magnetic stirring and argon gas, after heating the oil bath to 75°C, add 0.020g tetrakistriphenylphosphine palladium, reflux reaction for 24h, add water to quench the reaction, and then use organic Solvent extraction, and then distill off the solvent under reduced pressure.

[0039] S2. the product after the step S1 is evaporated to remove the solvent is purified by column chromatography with dichloromethane: normal hexane=1:1 (volume ratio) as the mobile phase silica gel as the stationary phase, and the product is collected and spin-dried, and dried in a vacuum at 80°C 24h, the product was obtained...

Embodiment 2

[0041] This example provides the synthesis of 4,4'-(10H-phenoxazine-2,7-diyl)dianiline:

[0042]

[0043]S1. Add 3.41g (0.01mol) 2,7-dibromo-10H-phenoxazine, 4.335g (0.025mol) p-aminophenyl borate hydrochloride into a 500ml three-necked flask, tetrahydrofuran (THF) as the solvent, and then add 2mol / L of potassium carbonate solution 37.5ml and appropriate amount of Aliquat336, magnetic stirring and argon gas, after heating the oil bath to 75°C, add 0.020g tetrakistriphenylphosphine palladium, reflux reaction for 24h, add water to quench the reaction, and then use organic Solvent extraction, and then distill off the solvent under reduced pressure.

[0044] S2. the product after the solvent is evaporated in step S1 is purified by column chromatography with dichloromethane: n-hexane=1:2 (volume ratio) as the mobile phase silica gel as the stationary phase, and the product is collected and spin-dried, and dried in a vacuum at 80°C 24h, the product was obtained.

Embodiment 3

[0046] This example provides the synthesis of 5,5'-(10H-phenoxazine-2,8-diyl)bis(thiophen-2-amine):

[0047]

[0048] S1. Add 3.41g (0.01mol) 2,8-dibromo-10H-phenoxazine, 3.574g (0.025mol) (5-aminothiophen-2-yl) boronic acid into a 500ml three-necked flask, tetrahydrofuran (THF) is the solvent, Then add 2mol / L potassium carbonate solution 37.5ml and an appropriate amount of Aliquat336, stir magnetically and pass argon, heat the oil bath to 75°C, add 0.020g tetrakistriphenylphosphine palladium, reflux reaction for 24h, add water to quench the reaction, Then it was extracted with an organic solvent, and the solvent was distilled off under reduced pressure.

[0049] S2. the product after the solvent is evaporated in step S1 is purified by column chromatography with dichloromethane: normal hexane=2: 1 (volume ratio) as the mobile phase silica gel as the stationary phase, and the product is collected and spin-dried, and dried in a vacuum at 80°C 24h, the product was obtained. ...

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Abstract

The invention discloses diamine with a novel structure and a preparation method and application thereof. According to the invention, starting from dihalogenated phenoxazine, a diamine monomer is prepared through a Suzuki reaction and a reduction reaction. The lowest-energy-state molecular structure of the novel diamine monomer has high planarity and a certain antibacterial property; and the molecular chains of a polymer taking the diamine monomer as a monomer are tightly piled up, and the polymer is small in free volume and has high barrier property and antibacterial property. The diamine disclosed by the invention can be used for synthesizing high-performance and functionalized polymers such as polyamide, polyimide, polyamideimide, polyesterimide and the like.

Description

technical field [0001] The present invention relates to the field of material science and technology, and more specifically, relates to a novel structure of diamine and its preparation method and application. Background technique [0002] Aromatic polyimide (PI) is a class of high-temperature-resistant materials with excellent performance. It contains strong rigid benzene rings and imide rings, and has excellent high-temperature resistance, mechanical properties, corrosion resistance and electrical properties. Widely used in aerospace, electronic devices, precision machinery, high-performance packaging, microelectronics and other new technology fields. However, polyimide has poor barrier properties to water and oxygen, which limits its application in fields requiring high barrier properties. [0003] The improvement of the barrier properties of polyimide in the prior art includes the use of multi-layer high barrier film composites to improve the barrier properties, such as ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D265/38C07D413/14C08G73/10
CPCC07D265/38C07D413/14C08G73/1085
Inventor 刘亦武谭井华
Owner HUNAN UNIV OF TECH
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