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4,5-diazafluorene-containing aromatic diamine as well as preparation method and application thereof

A technology of aromatic diamine and diazofluorene, which is applied in the field of aromatic diamine containing 4,5-diazofluorene and its preparation, can solve the problems of high melting temperature or softening temperature and poor solubility of polyimide, and achieve excellent Heat resistance and moist heat oxidation resistance, excellent film-forming performance, and high light transmission performance

Inactive Publication Date: 2014-09-17
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although aromatic polyimides have excellent properties, due to their rigid skeleton and strong interaction between chains, most polyimides have a high melting temperature or softening temperature, and in The solubility in most organic solvents is quite poor, which limits their application in related fields

Method used

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  • 4,5-diazafluorene-containing aromatic diamine as well as preparation method and application thereof
  • 4,5-diazafluorene-containing aromatic diamine as well as preparation method and application thereof
  • 4,5-diazafluorene-containing aromatic diamine as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment 1, the preparation method of 9,9-bis(4-aminophenyl)-4,5-diazofluorene of the present invention:

[0033] ① Add 100-150 parts (parts by weight) of aniline to a three-neck round bottom flask, add 30-50 parts of methanesulfonic acid or trifluoromethanesulfonic acid under stirring, and then add 30-50 parts of 4,5- Diazofen-9-one, stir well. In pass N 2 Under certain conditions, heat up to 50-170°C and react for 5-20 hours. When cooled below 80°C, neutralize with NaOH solution, filter, wash with water, and purify by recrystallization to obtain 9,9-bis(4-aminophenyl)-4,5-diazofluorene. Melting point: >300°C. FT-IR(KBr):3454-3331cm -1 (N–H stretch),3066~3004cm -1 (C–H stretch),1510cm -1 (C=N stretch). 1 H NMR (400MHz, DMSO-d 6 ,δ,ppm):5.03(s,4H,-NH 2 ), 6.42(d, J=8.4Hz, 2H), 6.75(d, J=8.4Hz, 2H), 7.35(dd, J=4.8, 4.8Hz, 2H,), 7.84(dd, J=1.6, 1.6 Hz,2H),8.62(dd,J=1.6,1.6Hz,2H). 13 C NMR (100MHz, DMSO-d 6 ,δ,ppm):59.8,114.1,123.9,128.5,131.0,134.2,147.5,148...

Embodiment 2

[0034] Embodiment 2, the preparation method of 9,9-bis(3-methyl-4-aminophenyl)-4,5-diazofluorene of the present invention:

[0035] ①Add 100-150 parts (by weight) of o-methylaniline to a three-necked round bottom flask, add 30-50 parts of methanesulfonic acid or trifluoromethanesulfonic acid under stirring, and then add 30-50 parts of 4 , 5-diazofluoren-9-one, stir well. In pass N 2 Under certain conditions, heat up to 50-170°C and react for 5-20 hours. When cooled to below 80°C, pour it into NaOH solution, stir overnight, filter, wash with water, and purify by recrystallization to obtain 9,9-bis(3-methyl-4-aminophenyl)-4, 5-diazofluorene. Melting point: 312-314°C. 1 H NMR (400MHz, Acetone-d 6 ,δ,ppm):2.0(m,6H),4.29(s,4H,-NH 2 ),6.54(dd,J=1.6,1.6Hz,2H),6.76(t,J=8.4,18Hz,4H),7.28(m,2H,),7.82(m,2H),8.61(m,2H) . 13 C NMR (100MHz, Acetone-d 6 ,δ,ppm):17.7,61.0,115.2,122.4,123.9,127.2,130.4,133.6,134.5,146.1,148.5,150.2,158.7.(EI-m / z):[M+H] + calcd for C 25 h 22 N 4 ,378...

Embodiment 3

[0036] Example 3, the preparation method of 9,9-bis(4-amino-3,5-difluorophenyl)-4,5-diazofluorene of the present invention:

[0037] ①Add 100-150 parts (parts by weight) of 2,6-difluoroaniline into a three-neck round bottom flask, add 30-50 parts of methanesulfonic acid or trifluoromethanesulfonic acid under stirring, and then add 30- 50 parts of 4,5-diazofluoren-9-one, fully stirred. In pass N 2 Under certain conditions, heat up to 50-170°C and react for 5-20 hours. When cooled to below 80°C, pour it into NaOH solution, stir overnight, filter, wash with water, and purify by recrystallization to obtain 9,9-bis(4-amino-3,5-difluorophenyl)- 4,5-diazofluorene. Melting point: 290-292°C. 1 H NMR (400MHz, Acetone-d 6 ,δ,ppm):4.79(s,4H,-NH 2 ),6.70(dd,J=2.4,2.0Hz,4H),7.41(dd,J=4.8,4.8Hz,2H),8.03(dd,J=1.6,1.2Hz,2H,),8.71(d,J =3.6Hz,2H). 13 C NMR (100MHz, Acetone-d 6 ,δ,ppm):60.3,111.4(J C-F =6.2,8.2Hz),124.5,125.5(J C-F =165Hz), 131.9(J C-F =78Hz), 134.5, 146.2, 148.0, 151...

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Abstract

The invention provides 4,5-diazafluorene-containing aromatic diamine and a preparation method thereof, and also provides an application of the 4,5-diazafluorene-containing aromatic diamine to preparing a polyimide material with excellent comprehensive performance. The prepared 4,5-diazafluorene-containing aromatic diamine is high in purity; the polyimide prepared from 4,5-diazafluorene-containing aromatic diamine has excellent comprehensive performances. namely excellent dissolving performance, thus can be dissolved in protonic solvents such as N, N-dimethyl acetamide (DMAc) and N, N-dimethyl formamide (DMF), and also can be dissolved in m-cresol and low-boiling point solvents, for example trichloromethane and dichloromethane; the polyimide has excellent film-forming performance so as to obtain a film which is uniform and good in toughness; the polyimide has excellent mechanical performance and electric performance, has excellent heat resistance and hot-humid oxidization resistance, and has a glass-transition temperature of 420-490 DEG C.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to an aromatic diamine containing 4,5-diazofluorene and its preparation method and application. Background technique [0002] Aromatic polyimide material has outstanding high temperature resistance, low temperature resistance, corrosion resistance, radiation resistance, high insulation, low dielectric loss, high light transmission performance, excellent mechanical properties, small water absorption and moisture absorption, etc. As a heat-resistant material and electronic packaging material, it is widely used in aviation, aerospace, electronic communication, electromechanical and microelectronics industries. Although aromatic polyimides have excellent properties, due to their rigid skeleton and strong interaction between chains, most polyimides have a high melting temperature or softening temperature, and in The solubility in most organic solvents is quite poor, which lim...

Claims

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Application Information

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IPC IPC(8): C07D471/04C08G73/10
CPCC07D471/04C08G73/1007C08G73/1053
Inventor 张树江李辉宫琛亮李彦锋
Owner LANZHOU UNIVERSITY
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