Aromatic diamine monomer and preparation method thereof

A technology of diamine monomer and aromatic type, which is applied in the field of aromatic diamine monomer and its preparation, can solve the problems of process controllability, poor repeatability, large specific surface area of ​​nanoparticles, and volatilization loss, etc., and achieve excellent resistance Ultraviolet radiation, high process controllability, and the effect of delaying damage

Active Publication Date: 2020-02-28
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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Problems solved by technology

[0005] However, the above-mentioned methods all use components with anti-ultraviolet radiation as guests to dope polyimide materials to obtain anti-ultraviolet radiation polyimide materials; wherein, adding anti-ultraviolet radiation nanoparticles to prepare anti- The method of ultraviolet irradiating polyimide materials has the problem of poor dispersion of nanoparticles in the polyimide main material, mainly due to the large specific surface area of ​​nanoparticles, which are easy to agglomerate, and it is necessary to ensure that the preparation and processing of polyimide materials The uniform dispersion of nanoparticles in the process will result in poor controllability and repeatability of the processing technology; and the anti-ultraviolet radiation polyimide material prepared by adding an anti-ultraviolet agent has the problem that the ultraviolet absorber is an organic small molecule, which is resistant to The thermal performance is poor, and it will be volatilized and lost when used in a high temperature environment, which will reduce or even lose the anti-ultraviolet radiation performance of polyimide materials
And the method for preparing intrinsic anti-ultraviolet radiation polyimide has not been reported yet.

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

[0048] The present invention also provides a method for preparing the aromatic diamine monomer described in the above technical solution, comprising the following steps:

[0049] a) carry out etherification reaction with the compound of structure shown in formula (I) with methoxyphenol in the presence of basic catalyst, obtain the compound with structure shown in formula (II); Described methoxyphenol is 3-methyl oxyphenol, 4-methoxyphenol or 3,5-dimethoxyphenol;

[0050] X-R 1 Formula (I);

[0051] In formula (I), X is fluorine, chlorine, bromine, iodine, methanesulfonyloxy, trifluoromethanesulfonyloxy or p-toluenesulfonyloxy;

[0052]

[0053] In formula (II), R 5 and R 6 independently selected from hydrogen or and R 5 with R 6 different;

[0054] b) performing a Friedel-Crafts acylation reaction on a compound having a structure shown in formula (II) and a dinitrobenzoyl halide in the presence of a catalyst to obtain a compound having a structure shown in formula...

Embodiment 1

[0130] (1) 37.24g (0.30 mole) 3-methoxyphenol, 54.47g (0.33 mole) n-hexane bromide, 49.76g (0.36 mole) potassium carbonate, 2.49g (0.015 mole) potassium iodide and 275g acetonitrile were added to In the reaction flask, the reaction system was then heated to 80°C for 6 hours. After being cooled to room temperature, it was added to 1500 milliliters of water, the product was extracted with dichloromethane, dried over anhydrous magnesium sulfate, the solvent was concentrated, and purified to obtain 53.74g of the representative compound 1-hexyloxy-3-methoxy with the structure shown in formula (II) The refined product of phenylbenzene, the yield is 86.0%.

[0131] 1H NMR (400MHz, DMSO) δ = 7.152 (t, J = 8.0Hz, 1H), 6.445-6.510 (m, 3H), 3.920 (t, J = 6.4Hz, 2H), 3.718 (s, 3H), 1.735 -1.625 (m, 2H), 1.460–1.355 (m, 2H), 1.345–1.205 (m, 4H), 0.875 (t, J=6.8Hz, 3H).

[0132] (2) 27.67g (0.12 moles) of 3,5-dinitrobenzoyl chloride, 17.33g (0.13 moles) of aluminum trichloride, 350g of 1...

Embodiment 2

[0139] (1) 62.07g (0.50 mole) 3-methoxyphenol, 78.75g (0.45 mole) p-bromofluorobenzene, 4.76g (0.025 mole) cuprous iodide, 82.93g (0.60 mole) potassium carbonate and 420gN, N-dimethylformamide was sequentially added into the reaction flask, and the reaction system was heated to 150° C. for 8 hours under the protection of nitrogen. After being cooled to room temperature, it was added to 2500 ml of water, the product was extracted with dichloromethane, washed with dilute hydrochloric acid, dried over anhydrous magnesium sulfate, the solvent was concentrated, and 77.58 g of the representative compound 1-(4-fluoro The refined product of phenoxy)-3-methoxybenzene, the yield is 79.0%.

[0140] 1 H NMR (400MHz, DMSO) δ=7.295–7.175(m,3H),7.105–7.025(m,2H),6.703(dd,J=8.4Hz,2.2Hz,1H),6.557(t,J=2.2Hz , 1H), 6.504 (dd, J = 8.2Hz, 2.2Hz, 1H), 3.728 (s, 3H).

[0141] (2) 27.67g (0.12 mol) 3,5-dinitrobenzoyl chloride, 17.33g (0.13 mol) aluminum trichloride, 360g1,2-dichloroethane and 21.8...

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Abstract

The invention provides an aromatic diamine monomer. The aromatic diamine monomer has a structure shown as formula (V), in the formula (V), R1 is selected from alkyl, substituted alkyl, phenyl or substituted phenyl; R2 and R3 are independently selected from hydroxyl or a group disclosed in the invention, and are different from each other; and R4 is selected from hydrogen or a group disclosed in theinvention. Compared with the prior art, the aromatic diamine monomer provided by the invention contains an o-hydroxyl benzophenone structural unit; the o-hydroxyl benzophenone structural unit can beintroduced into a polyimide macromolecular chain through copolymerization; when the material is exposed to an ultraviolet radiation environment, the o-hydroxyl benzophenone structure can absorb ultraviolet light and release the ultraviolet light in the form of heat to prevent or delay the damage of ultraviolet radiation to the polyimide material, so that the obtained polyimide material has excellent intrinsic ultraviolet radiation resistance.

Description

technical field [0001] 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 [0002] Polyimide is a kind of special polymer material with excellent comprehensive performance. The molecular chain contains imide rings. It not only has the advantages of high temperature resistance, high strength, high modulus, chemical corrosion resistance, and low temperature resistance, but also has low The dielectric constant and thermal expansion coefficient have been widely used in high-tech fields such as aerospace, national defense construction, high-speed transportation, and microelectronics. [0003] The performance of polyimide materials will be affected by the environment during use. After being irradiated by ultraviolet rays, photochemical reactions will occur on the surface of the material, which will change the chemical composition of the material and l...

Claims

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Application Information

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IPC IPC(8): C07C221/00C07C225/22C08G73/10C08G69/40
CPCC07C225/22C08G69/40C08G73/1007C08G73/1071
Inventor 姚海波董志鑫杜志军矫龙蔡艳春邱雪鹏
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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