Monoamine-monophenol type quinoxalinyl benzoxazine and preparation method thereof
A technology of quinoxalinylbenzene and hydroxyquinoxaline, which is applied in the field of organic polymer materials and can solve the problems of restricting the designability of benzoxazine monomers and the limitation of performance control of benzoxazine resins.
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Embodiment 1
[0023] (1) Add 4-nitrobenzil (25.5g, 0.1mol) and 4-hydroxy-o-phenylenediamine (15.3g, 0.1mol) and 250mL of glacial acetic acid to the three-necked flask respectively, and the mixture is refluxed for 6h, then cooled After reaching room temperature, the formed precipitate was collected by filtration and dried, and the resulting crude product was recrystallized three times with glacial acetic acid to obtain 2-(4-nitrophenyl)-3-phenyl-6-hydroxyl and 2-phenyl- 3-(4-nitrophenyl)-6-hydroxyquinoxaline mixture (M1, 25.2g), yield 73.9%;
[0024] (2) M1 (17.2g, 0.05mol) and palladium-carbon catalyst (0.7g) were added to 300mL ethanol, then 80% hydrazine hydrate (5.6g, 0.09mol) was added dropwise, and reacted at reflux temperature for 12h. Remove the palladium-carbon catalyst by hot filtration, cool the filtrate to room temperature, precipitate crystals, filter, wash with distilled water for 3 to 4 times, and finally dry in vacuum to obtain 2-(4-aminophenyl)-3-phenyl-6-hydroxyl Quinoxali...
Embodiment 2
[0030] In addition to changing the raw material 2-hydroxybenzaldehyde into 4-methyl-2-hydroxybenzaldehyde (2.7g, 0.02mol) in step (3), M3 in step (4) is changed into 2-(2-hydroxyl-5- Methyl-benzylamino)-3-phenyl-6-hydroxyquinoxaline mixture (4.3g, 0.01mol), except that aniline is changed into n-butylamine (0.74g, 0.01mol), other conditions are the same as in Example 1, Finally, a methyl-containing butylamine-monoamine-monophenol type quinoxalinyl benzoxazine monomer was obtained with a yield of 76.2%.
[0031] Proton NMR spectrum test result (500M, CDCl 3 , ppm): 8.34~6.60 (m, 14H, Ar-H), 5.03 (s, 2H, O-CH 2 -N), 4.99(s, 2H, O-CH 2 -N), 4.23(s, 2H, Ar-CH 2 -N), 4.07(s, 2H, Ar-CH 2 -N), 2.76(t, 2H, N-CH 2 -CH 2 ), 1.31~1.57 (m, 4H, CH 2 -CH 2 -CH 2 ), 0.86(t, 6H, -CH 3 ); infrared spectrum test results (KBr, cm -1 ): 1373, 1323, 1230, 1072, 1173, 951 and 932.
[0032] Curing and test condition are with embodiment 1, the T of polybenzoxazine resin g , T 5 , T 10 a...
Embodiment 3
[0034] In addition to changing the raw material 2-hydroxybenzaldehyde into 5-fluoro-2-hydroxybenzaldehyde (2.8g, 0.02mol) in step (3), M3 in step (4) is changed into 2-(2-hydroxyl-5-fluoro -benzylamino)-3-phenyl-6-hydroxyquinoxaline and 2-phenyl-3-(2-hydroxy-5-fluoro-benzylamino)-6-hydroxyquinoxaline (4.4g, 0.01 mol), aniline is changed into except n-octylamine (1.29g, 0.01mol), other conditions are with embodiment 1, finally obtain fluorine-containing octylamine-monoamine-monophenol type quinoxalinyl benzoxazine monomer, Yield 72.1%.
[0035] Proton NMR test results (500M, DMSO, ppm): 8.34~6.59(m, 14H, Ar-H), 4.98(s, 2H, O-CH 2 -N), 4.97(s, 2H, O-CH 2 -N), 4.15(s, 2H, Ar-CH 2 -N), 4.13(s, 2H, Ar-CH 2 -N), 2.72(t, 2H, N-CH 2 -CH 2 ), 1.28~1.57 (m, 12H, CH 2 -CH 2 -CH 2 ), 0.89(t,3H,-CH 3 ); infrared spectrum test results (KBr, cm -1 ): 1323, 1230, 1073, 1173, 947 and 935.
[0036] Curing and test condition are with embodiment 1, the T of polybenzoxazine resin g , ...
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