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Triamine monomer containing benzothiazole structure and preparation method and application thereof

A technology of benzothiazole and triamine monomers, applied in the direction of organic chemistry, etc., can solve the problems of inability to have both thermal properties and solubility of hyperbranched polyimide, few types of triamine monomers, and unstable thermal properties. , to achieve the effects of improving stability and synthesis rate, low solution and melt viscosity, and mild reaction conditions in the synthesis process

Inactive Publication Date: 2018-11-23
HUNAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The technical problem to be solved by the present invention is that in the prior art, there are few types of triamine monomers, unstable thermal properties, low synthesis rate, and the inability to have both thermal properties and solubility of hyperbranched polyimides prepared from existing triamines etc. insufficient to provide a counter-

Method used

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  • Triamine monomer containing benzothiazole structure and preparation method and application thereof
  • Triamine monomer containing benzothiazole structure and preparation method and application thereof
  • Triamine monomer containing benzothiazole structure and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] N 1 -(4-aminophenyl)-N 1 -Synthesis of (6-(4-aminophenyl)benzo[d]thiazol-2-yl)benzene-1,4-diamine:

[0056]

[0057] S1. Synthesis of intermediate 6-bromo-N, N-bis(4-nitrophenyl)benzo[d]thiazol-2-amine:

[0058] Add 2.291g (0.01mol) of 2-amino-6-bromobenzothiazole and 7.055mL (0.05mol) of p-fluoronitrobenzene into a 250mL three-necked flask, use DMSO as the solvent, magnetically stir and argon, and heat in an oil bath After reaching 150°C, 3.038g (0.02mol) cesium fluoride (CsF) was added, and the reaction was refluxed for 24h. The reaction solution was poured into ice water, extracted with dichloromethane, decompressed to -101.325kPa to evaporate the solvent, and the product used dichloromethane:n-hexane=1:1 (volume ratio) as the mobile phase and silica gel as the stationary phase. After chromatographic purification, the product was collected and spin-dried, and dried in vacuum at 80° C. for 24 hours to obtain 3.912 g of the product with a yield of 83%. The inter...

Embodiment 2

[0069] N 2 -(5-(4-aminophenyl)benzo[d]thiazol-2-yl)-N 2 -Synthesis of (5-aminothiophen-2-yl)thiophene-2,5-diamine:

[0070]

[0071] S1. Synthesis of intermediate 5-bromo-N, N-bis(5-nitrothiophen-2-yl)benzo[d]thiazol-2-amine:

[0072] Add 2.291g (0.01mol) of 2-amino-5-bromobenzothiazole and 12.752mg (0.05mol) of 2-iodo-5-nitrothiophene into a 250mL three-necked flask with DMSO as the solvent, magnetically stir and argon , heated the oil bath to 150°C, then added 3.038g (0.02mol) cesium fluoride (CsF), and refluxed for 24h. The reaction solution was poured into ice water, extracted with dichloromethane, decompressed to -101.325kPa to evaporate the solvent, and the product used ethyl acetate:petroleum ether=1:10 (volume ratio) as the mobile phase and silica gel as the stationary phase. After chromatographic purification, the product was collected and spin-dried, and dried in vacuum at 80° C. for 24 hours to obtain 3.142 g of the product with a yield of 65%. The intermedia...

Embodiment 3

[0083] N 2 -(6-aminonaphthalen-2-yl)-N 2 -Synthesis of (7-(4-aminophenyl)benzo[d]thiazol-2-yl)naphthalene-2,6-diamine:

[0084]

[0085] S1. Synthesis of intermediate 7-bromo-N, N-bis(6-nitronaphthalen-2-yl)benzo[d]thiazol-2-amine:

[0086] Add 2.291g (0.01mol) of 2-amino-7-bromobenzothiazole and 14.953mg (0.05mol) of 2-iodo-6-nitronaphthalene into a 250mL three-necked flask with DMSO as the solvent, magnetically stir and argon , heated the oil bath to 150°C, then added 3.038g (0.02mol) cesium fluoride (CsF), and refluxed for 24h. The reaction solution was poured into ice water, extracted with dichloromethane, decompressed to -101.325kPa to evaporate the solvent, and the product used dichloromethane:n-hexane=1:1 (volume ratio) as the mobile phase and silica gel as the stationary phase. After chromatographic purification, the product was collected and spin-dried, and dried in vacuum at 80° C. for 24 hours to obtain 3.486 g of the product with a yield of 61%. The intermed...

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Abstract

The invention discloses a triamine monomer containing a benzothiazole structure, and a preparation method and application thereof. The preparation method comprises the following steps of using a benzothiazole monomer which contains one halogen atom and has one substituted amino group; performing a series of chemical reaction, such as Ullmann coupling reaction, Suzuki reaction and reduction reaction, so as to prepare the triamine monomer containing the benzothiazole structure. The triamine monomer containing the benzothiazole structure has the advantages that the heat-resistant property and heat stability are high; the preparation method and technology are simple, the purification is easy, and the triamine monomer is suitable for industrialized production; by introducing the benzothiazole into the triamine monomer, the heat stability of the monomer is obviously improved, the heat stability and mechanical property of the prepared polymer are improved, and the processing property is obviously improved; the triamine monomer containing the benzothiazole structure is suitable for synthesizing hyperbranched and functionalized polyimides, polyamides, polyamides, polyesterimides and other polymers.

Description

technical field [0001] The invention relates to the technical field of organic small molecule materials and polymer materials, and more specifically, relates to a triamine monomer containing a benzothiazole structure and its preparation method and application. Background technique [0002] Polyimide due to its outstanding performance characteristics, such as excellent high and low temperature resistance, excellent resistance to organic solvents, excellent mechanical properties, low thermal expansion coefficient, hydrolysis resistance, light radiation resistance, excellent electrical properties, flame retardant , non-toxic and low volatility, etc., so that it has received more and more attention and application. However, the excellent thermal stability and solvent resistance of polyimide make it difficult to process and shape. [0003] Hyperbranched polymers have a highly branched structure and exhibit many special properties different from linear polymers. The molecular st...

Claims

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Application Information

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IPC IPC(8): C07D277/82C07D417/14C07D417/04C08G73/10
CPCC07D277/82C07D417/04C07D417/14C08G73/1003C08G73/1039C08G73/1064
Inventor 谭井华彭思梅刘亦武佘志鸿
Owner HUNAN UNIV OF TECH
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