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Diamine with antibacterial effect and preparation method thereof

A technology of diamine and diamine monomer, which is applied in the field of material science, can solve the problems such as the adverse effects of polyimide on mechanical properties and thermal stability, the inability to meet the performance requirements of polyimide, and the limited improvement of barrier properties. Achieve high glass transition temperature and thermal stability, broad-spectrum antibacterial and antibacterial activity, and high electron density

Inactive Publication Date: 2020-05-08
HUNAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, polyimide has the disadvantages of low barrier performance and high water oxygen transmission rate, and the antibacterial property of polyimide is insufficient, so it is difficult to ensure that the contents are not polluted under the condition of high water oxygen transmission rate.
[0003] In the prior art, the improvement of the barrier performance of polyimide is mostly prepared by adding nano-inorganic substances to prepare composite films. Through operations such as selection, stripping, and modification of nano-inorganic substances, the dispersion of nano-inorganic substances in the matrix is ​​improved The barrier performance of imide, 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
To make the polyimide film have antibacterial effect, it is necessary to add antibacterial agents, such as silver, copper, zinc metal oxides or chitosan and other organic substances. Detrimental effect on mechanical properties and thermal stability of polyimide

Method used

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  • Diamine with antibacterial effect and preparation method thereof
  • Diamine with antibacterial effect and preparation method thereof
  • Diamine with antibacterial effect and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] This example provides the synthesis of 2,7-bis(4-aminophenyl)-9H-xanthen-9-one:

[0036]

[0037] S1. Add 3.54g (0.01mol) 2,7-dibromo-9H-xanthen-9-one, 4.335g (0.025mol) p-aminophenyl borate hydrochloride into a 500ml three-necked flask, tetrahydrofuran (THF) as solvent , then add 37.5ml of 2mol / L potassium carbonate solution and an appropriate amount of Aliquat336, stir magnetically and pass argon, heat the oil bath to 50°C, add 0.020g tetrakistriphenylphosphine palladium, reflux for 48 hours, and then quench the reaction with water , and then extracted with an organic solvent, and then distilled off the solvent under reduced pressure.

[0038] S2. The product after the solvent is evaporated in step S1 is purified by column chromatography with dichloromethane:n-hexane=1:1 (volume ratio) as the mobile phase silica gel as the stationary phase, the product is collected and spin-dried, and dried in a vacuum at 120°C 6h, the product was obtained.

Embodiment 2

[0040] This example provides the synthesis of 2,6-bis(4-aminophenyl)-9H-xanthen-9-one:

[0041]

[0042]S1. Add 3.54g (0.01mol) 2,6-dibromo-9H-xanthen-9-one, 4.335g (0.025mol) p-aminophenyl borate hydrochloride into a 500ml three-necked flask, tetrahydrofuran (THF) as solvent , then add 37.5ml of 2mol / L potassium carbonate solution 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 , and then extracted with an organic solvent, and then distilled off the solvent under reduced pressure.

[0043] S2. The product after the step S1 is evaporated to remove the solvent 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

[0045] This example provides the synthesis of 2,7-bis(5-aminothiophen-2-yl)-9H-xanthen-9-one:

[0046]

[0047] S1. Add 3.54g (0.01mol) 2,7-dibromo-9H-xanthen-9-one, 3.574g (0.025mol) (5-aminothiophen-2-yl) boronicacid into a 500ml three-necked flask, tetrahydrofuran (THF) As a solvent, add 37.5ml of 2mol / L potassium carbonate solution and an appropriate amount of Aliquat336, stir magnetically and pass argon, heat the oil bath to 75°C, add 0.020g tetrakistriphenylphosphine palladium, reflux for 24h, add water to quench The reaction was quenched, then extracted with an organic solvent, and the solvent was distilled off under reduced pressure.

[0048] 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 an antibacterial effect and a preparation method thereof. According to the invention, a two-halogen-atom-substituted xanthone monomer is grafted with an amino-containing group through the Suzuki reaction, or grafted with a nitro-containing group through the Suzuki reaction and then reduced to obtain a diamine monomer containing a xanthone structure. The xanthone structure has high electron density and a good rigid structure; and the planar rigid structure is beneficial for regular stacking of polymer molecular chains and induction of polymer crystallization, and a polymer with tightly stacked molecular chains, small free volume and high barrier property can be prepared. Meanwhile, the diamine disclosed by the invention takes the xanthone structure as acore and has good antibacterial and bacteriostatic effects, and the polymer prepared by taking the diamine as a raw material also has a certain antibacterial property.

Description

technical field [0001] The invention relates to the technical field of material science, more specifically, to a diamine with antibacterial effect and a preparation method thereof. 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 characteristics such as high glass transition temperature, high strength, and low thermal expansion coefficient. Polyimide is used as a packaging material, and its heat resistance, stability, flame retardancy and non-toxicity all meet the requirements of packaging materials. However, polyimide has the disadvantages of low barrier performance and high water oxygen transmission rate, and the antibacterial property of polyimide is insufficient, so it is difficult to ensure that the contents are not polluted under the condition of high water oxygen transmission rate. [0003] In the prior art, the...

Claims

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Application Information

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IPC IPC(8): C07D311/86C07D409/14C07D405/14A01N43/16A01N43/40A01N43/60A01P1/00C08G73/10C08J5/18C08L79/08
CPCA01N43/16A01N43/40A01N43/60C07D311/86C07D405/14C07D409/14C08G73/1085C08J5/18C08J2379/08
Inventor 谭井华刘亦武张祥周栋
Owner HUNAN UNIV OF TECH
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