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Aromatic diamine monomer and preparation method thereof

A diamine monomer and aromatic technology, applied in the field of aromatic diamine monomer and its preparation, can solve the problems of large specific surface area of ​​nanoparticles, poor dispersion of nanoparticles, poor heat resistance, etc., and achieve process controllability High, simple route, low cost effect

Active Publication Date: 2020-01-10
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] However, the above-mentioned methods all add components with anti-ultraviolet radiation effects as guests to the polyimide host material to obtain an anti-ultraviolet radiation polyimide material, wherein, adding anti-ultraviolet radiation nanoparticles to prepare The method of anti-ultraviolet radiation polyimide material has the problem of poor dispersion of nanoparticles in the polyimide host material, mainly due to the large specific surface area of ​​nanoparticles, which is easy to agglomerate; and the anti-ultraviolet radiation prepared by adding an anti-ultraviolet agent Polyimide material, the problem is that the UV absorber is a small organic molecule, which has poor heat resistance and cannot be used in a high temperature environment

Method used

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  • Aromatic diamine monomer and preparation method thereof
  • Aromatic diamine monomer and preparation method thereof
  • Aromatic diamine monomer and preparation method thereof

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preparation example Construction

[0049] The present invention also provides a method for preparing the aromatic diamine monomer described in the above technical solution, comprising the following steps:

[0050] a) carry out etherification reaction with methoxyphenol and the substituted nitrobenzene of structure shown in formula (I) in the presence of basic catalyst, obtain the compound with structure shown in formula (II); Described methoxyphenol is 3-methoxyphenol or 4-methoxyphenol;

[0051]

[0052] In formula (I), X is fluorine, chlorine, bromine, iodine, methanesulfonyloxy, trifluoromethanesulfonyloxy or p-toluenesulfonyloxy, R 7 and R 8 are independently selected from hydrogen or nitro, and R 7 with R 8 different;

[0053]

[0054] In formula (II), R 9 and R 10 are independently selected from hydrogen or methoxy, and R 9 with R 10 different;

[0055] b) Carrying out a Friedel-Crafts acylation reaction between a compound having a structure shown in formula (II) and a nitrobenzoyl halide i...

Embodiment 1

[0135] (1) Add 69.52g (0.56mol) of 3-methoxyphenol, 88.23g (0.56mol) of p-nitrochlorobenzene, 85.14g (0.616mol) of potassium carbonate and 200g of dimethyl sulfoxide into the reactor in sequence , heated to 160°C and reacted for 6h; cooled to 60°C, added to 2000mL water, precipitated crude product, filtered out, dissolved in dichloromethane after washing, dried over anhydrous magnesium sulfate, concentrated solvent, obtained crude product again, and re- Crystallization obtained 114.23 g of the refined product of compound (II-1) represented by formula (II); the yield was 83.2%.

[0136] Utilize nuclear magnetic resonance to characterize the structural compound (II-1) shown in the formula (II) that obtains, the proton nuclear magnetic resonance spectrum result that obtains is: 1 H NMR (400MHz, DMSO) δ = 8.280–8.205 (m, 2H), 7.389 (t, J = 8.2Hz, 1H), 7.170–7.095 (m, 2H), 6.875 (dd, J = 8.3Hz, 2.2Hz , 1H), 6.776(t, J=2.2Hz, 1H), 6.731(dd, J=8.0Hz, 2.0Hz, 1H), 3.765(s, 3H).

[01...

Embodiment 2

[0144] (1) Refer to step (1) of Example 1 to obtain the refined product of compound (II-1) shown in formula (II).

[0145] (2) 18.56g (0.1mol) 3-nitrobenzoyl chloride, 14.67g (0.11mol) aluminum trichloride, 250g 1,2-dichloroethane and 22.07g (0.09mol) formula (II) Compounds (II-1) showing the structure were sequentially added into the reactor, stirred and reacted at 20°C for 30 h; then slowly added to ice-hydrochloric acid for treatment, separated, dried over anhydrous magnesium sulfate, and concentrated solvent to obtain a crude product, which was subjected to Recrystallization obtained 21.02 g of refined product of compound (III-3) represented by formula (III); the yield was 59.2%.

[0146] Utilize nuclear magnetic resonance to characterize the structural compound (III-3) shown in the formula (III) that obtains, the proton nuclear magnetic resonance spectrum result that obtains is: 1 HNMR (400MHz, DMSO) δ=8.490(d, J=8.0Hz, 1H), 8.425(s, 1H), 8.312(d, J=9.1Hz, 2H), 8.129(d, ...

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Abstract

The invention provides an aromatic diamine monomer. The aromatic diamine monomer has a structure shown in the formula (V), in the formula (V), R1 and R2 are independently selected from hydroxyl groupsor / and the R1 is different from the R2, R3, R4, R5, and R6 are independently selected from hydrogen or amino groups, the R3 is different from the R4, and the R5 is different from the R6. Compared with the prior art, the aromatic diamine monomer provided by the invention contains a structural unit of o-hydroxybenzophenone, through copolymerization, the structural unit of the o-hydroxybenzophenonecan be introduced into a main chain of a polyimide polymer material, when the material is exposed to an ultraviolet radiation environment, the structure of the o-hydroxybenzophenone can absorb ultraviolet light and releases the ultraviolet light in the form of heat to prevent or delay the damage of the polyimide material by ultraviolet irradiation, and thus the obtained polyimide material has excellent intrinsic resistance to ultraviolet irradiation.

Description

[0001] This application requires that the Chinese patent application submitted to the China Patent Office on July 08, 2019, with the application number 201910610423.8, and the invention name "A Polyimide-based Traction Belt" and the Chinese patent submitted on July 08, 2019 Bureau, application number is 201910609959.8, and the title of the invention is "a polyimide composite foam precursor powder and polyimide composite foam", the entire content of which is incorporated in this application by reference. technical field [0002] The invention relates to the technical field of polymer materials, and more specifically relates to an aromatic diamine monomer and a preparation method thereof. Background technique [0003] Polyimide is a kind of special polymer material with excellent comprehensive performance. It not only has excellent high and low temperature resistance, mechanical properties and chemical stability, but also has low dielectric constant and thermal expansion coeffi...

Claims

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Application Information

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IPC IPC(8): C08L79/08C08K7/06C08K7/14C08G73/10
CPCC08G73/1042C08G73/1071C08K7/06C08K7/14C08L79/08C08L2205/025C08L2205/16
Inventor 姚海波董志鑫杜志军矫龙王汉夫邱雪鹏
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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