Aromatic diamine with phthalonitrile pendant group, preparation method thereof and polyimides or polyamide prepared therefrom
A technology of phthalonitrile and aromatic diamine, applied in the dehydration preparation of carboxylic acid amide, organic chemistry and other directions
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Embodiment 1
[0088] This embodiment is the synthesis of monomer 1 in the first type of monomer and the embodiment of using it to prepare polyimide and polyamide respectively.
[0089] Dissolve 1 mol of 3,5-dinitrophenol and 1 mol of 4(3)-nitrophthalonitrile in 1L of DMF, then add 2 mol of anhydrous potassium carbonate, stir at room temperature for 24 hours, and pump under reduced pressure Dry the solvent, wash with water, separate and dry to obtain intermediate I-1; add 1g of I-1 intermediate and 20ml of absolute ethanol to the reaction kettle, and then add 5 % Pd / C (concentration 5%), react at room temperature for 48h, filter, and drain the solvent to obtain monomer 1.
[0090] The FTIR of obtained monomer 1 (cm -1 ): 3446, 3363 (N-H), 3036 (C=C-H), 2233 (CN), 1487-1607 (C=C), 1251 (C-O-C). 1 H NMR (DMSO-d 6 ppm): 8.05-8.08 (d, 1H, Ar-H), 7.71-7.72 (d, 1H, Ar-H), 7.32-7.36 (dd, 1H, Ar-H), 6.30-6.35 (dd, 2H, Ar-H), 6.22-6.25(m, 1H, Ar-H), 4.3(s, 4H, NH 2 ). Elemental analysis calcula...
Embodiment 2
[0094] This embodiment is the synthesis of monomer 2 in the first type of monomer and the embodiment of using it to prepare polyimide and polyamide respectively.
[0095] First dissolve 0.3mol 4,4'-dinitro-2,2'-dihydroxybiphenyl and 1mol 4(3)-nitrophthalonitrile in 800ml NMP, then add 3mol anhydrous sodium carbonate , and stirred at 80°C for 12 hours, then vacuum-dried the solvent, washed with water, separated and dried to obtain intermediate I-1; put 1g of I-1 intermediate and 20ml THF into the reaction kettle, and then added The mass of intermediate I-1 was 0.5% Pd / C (concentration: 10%), reacted at 40°C for 24 hours, filtered, and the solvent was drained to obtain monomer 2.
[0096] The FTIR of obtained monomer 2 (cm -1 ): 3455, 3371(N-H), 3045(C=C-H), 2233(CN), 1473-1628(C=C), 1088(C-O-C), 1248(C-O-C). 1 H NMR (DMSO-d 6 ppm): 8.05-8.08 (d, 2H, Ar-H), 7.71-7.72 (d, 2H, Ar-H), 7.32-7.50 (m, 4H, Ar-H), 6.25-6.28 (m, 2H, Ar-H), 6.18-6.20(d, 2H, Ar-H), 5.01(s, 4H, NH 2 )....
Embodiment 3
[0100] This example is an example of the synthesis of monomer 3 in the type II monomer and its use to prepare polyimide and polyamide respectively.
[0101] First, 3,5-dinitrobenzoyl chloride and anisole were completely dissolved in 2000ml of dichloromethane in a molar ratio of 0.9:1, and then anhydrous aluminum trichloride with an anisole molar ratio of 4 was added, And react at 10°C for 6 hours, then pour into 20% dilute hydrochloric acid solution, separate liquid and drain the solvent to obtain the product 3,5-dinitro-4'-hydroxybenzophenone.
[0102] or
[0103] First 3,5-dinitrobenzoyl chloride and phenetole are dissolved completely in 3000ml of carbon disulfide in a molar ratio of 1:1, then add anhydrous zinc trichloride that is 1:1.1 with the phenetole molar ratio, and in React at 30°C for 3 hours, then pour into 5% dilute sulfuric acid solution, separate liquid and drain the solvent to obtain the product 3,5-dinitro-4'-hydroxybenzophenone.
[0104] or
[0105] Firs...
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