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Bipyrimidyl dibenzene/diether/diamine and synthesis method thereof

A bipyrimidine and bipyrimidine-based technology, applied in the field of organic compounds and their preparation, can solve the problems of unfavorable production safety and environmental protection, low reaction yield, etc., to achieve safety production and environmental protection, improve reaction yield, The effect of performance improvement

Inactive Publication Date: 2014-12-24
JIANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, it has been found in practice that the synthetic process of this compound has defects such as the use of highly toxic NaCN decomplexation and other post-treatments, and the reaction yield is low, which is not conducive to production safety and environmental protection, and the performance of the PI obtained after polymerization also needs to be determined. Further improve

Method used

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  • Bipyrimidyl dibenzene/diether/diamine and synthesis method thereof
  • Bipyrimidyl dibenzene/diether/diamine and synthesis method thereof
  • Bipyrimidyl dibenzene/diether/diamine and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] 850ml of dehydrated N,N-dimethylformamide was deoxygenated with argon for 5 hours, 45.80g (0.18mol) of triphenylphosphine, NiCl 2 .H 2 O10.40 g (0.044 mol) and activated zinc powder 5.70 g (0.086 mo) were deoxygenated under vacuum for 20 minutes, added to DMF under the protection of argon, and stirred at room temperature under the protection of argon. After one hour, add 20.00 g (0.18 mol) of 2-chloropyrimidine, react at room temperature for one hour, then react at 50°C for 30 hours, filter with suction, wash the solid with chloroform, evaporate the filtrate to dryness, add 75 g of ETDA and NH to the solid 3 .H 2 O (200mL, 7%) was stirred in a solution, extracted with ethyl acetate (3×200mL), and the remaining solution was extracted with chloroform (8×150mL), washed with Na 2 SO 4 Dry and evaporate chloroform to dryness to obtain a light yellow solid, which is recrystallized from ethyl acetate:methanol=19:1 to obtain 23.87 g of white product bipyrimidine with a yield...

Embodiment 2

[0047] 850ml of dehydrated N,N-dimethylformamide was deoxygenated with argon for 5 hours, 45.80g (0.18mol) of triphenylphosphine, NiCl 2 .H 2 O10.40 g (0.044 mol) and activated zinc powder 5.70 g (0.086 mo) were deoxygenated under vacuum for 20 minutes, added to DMF under the protection of argon, and stirred at room temperature under the protection of argon. After one hour, add 20.00 g (0.18 mol) of 2-chloropyrimidine, react at room temperature for one hour, then react at 50°C for 30 hours, filter with suction, wash the solid with chloroform, evaporate the filtrate to dryness, add 75 g of ETDA and NH to the solid 3 .H 2 O (200mL, 7%) was stirred in a solution, extracted with ethyl acetate (3×200mL), and the remaining solution was extracted with chloroform (8×150mL), washed with Na 2 SO 4 Dry and evaporate chloroform to dryness to obtain a light yellow solid, which is recrystallized from ethyl acetate:methanol=19:1 to obtain 23.87 g of white product bipyrimidine with a yield...

Embodiment 3

[0054] 850ml of dehydrated N,N-methylformamide was deoxygenated with argon for 5 hours, 45.80g (0.18mol) of triphenylphosphine, NiCl 2 .H 2 O10.40 g (0.044 mol) and activated zinc powder 5.70 g (0.086 mo) were deoxygenated under vacuum for 20 minutes, added to DMF under the protection of argon, and stirred at room temperature under the protection of argon. After one hour, add 20.00 g (0.18 mol) of 2-chloropyrimidine, react at room temperature for one hour, then react at 50°C for 30 hours, filter with suction, wash the solid with chloroform, evaporate the filtrate to dryness, add 75 g of ETDA and NH to the solid 3 .H 2 O (200mL, 7%) was stirred in a solution, extracted with ethyl acetate (3×200mL), and the remaining solution was extracted with chloroform (8×150mL), washed with Na 2 SO 4 Dry and evaporate chloroform to dryness to obtain a light yellow solid, which is recrystallized from ethyl acetate:methanol=19:1 to obtain 23.87 g of white product bipyrimidine with a yield o...

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Abstract

The invention provides an aromatic diamine containing a bipyrimidyl structure. The chemical structural formula is shown as Formula (1). The diamine can be used as a raw material for the preparation of multiple polyimides and polyamides containing pyrimidyl, can enrich the polymer variety, can enhance the heat resistance and dielectric property of the polymer, and is beneficial to improve the application processing performance of polyimides and polyamides and widen the application area thereof. The invention also provides a preparation method of the aromatic diamine containing a bipyrimidyl structure.

Description

technical field [0001] The invention belongs to the technical field of organic compounds and preparation methods thereof, and in particular relates to a class of aromatic diamine monomers containing a bipyrimidine structure and a synthesis method thereof. Background technique [0002] Polyimide (PI) is a kind of polymer material containing imide rings in the main chain, which has excellent heat resistance and chemical stability, and has excellent mechanical and electrical properties. It is widely used in aviation and aerospace. , electrical, microelectronics and automobiles and other high-tech fields. The pyrimidine ring has higher thermal stability and polarity than the benzene ring, and the bipyrimidine structure has a chelating function. Introducing a bipyrimidine structure into the molecular structure of PI will help to improve the thermal stability and dielectric constant of PI materials, as well as endow them with chelating functions, forming PI / metal chelating cross-...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D239/34C08G73/10C08G69/00
Inventor 侯豪情彭信文吴琼陈水亮
Owner JIANGXI NORMAL UNIV
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