Oxazine compound, composition and cured product
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Embodiment 1
[0265] [Example 1] Synthesis of benzoxazine compound (A-1)
[0266] 198.3 g (1.0 mol) of 4,4'-diaminodiphenylmethane, 4-ene 300.4 g (2.0 mol) of propoxyphenol was dissolved in 1270 g of toluene, 127.8 g (4.0 mol) of 94% paraformaldehyde was added, the temperature was raised to 80°C while stirring, and the reaction was carried out at 80°C for 7 hours. After the reaction, transfer to a separatory funnel and remove the aqueous layer. Thereafter, the solvent was removed from the organic layer under reduced pressure under heating to obtain 437 g of a benzoxazine compound (A-1).
[0267] 1 H-NMR shows 7.03ppm (4H), 6.99ppm (4H), 6.71ppm-6.66ppm (4H), 6.54ppm (2H), 6.01ppm (2H), 5.37ppm (2H), 5.26ppm-5.23ppm ( 6H), 4.53ppm (4H), 4.43ppm (4H), 4.53ppm (4H), 3.78ppm (2H) peaks, 13 C-NMR showed 152.3ppm, 148.2ppm, 146.4ppm, 134.2ppm, 133.3ppm, 129.3ppm, 121.1ppm, 118.3ppm, 118.3ppm, 117.2ppm, 114.5ppm, 112.2ppm, 79.5ppm, 69.2ppm, 50.4ppm, 40.0ppm peak, mass spectrum showed M + =54...
Embodiment 2
[0269] [Example 2] Synthesis of benzoxazine compound (A-2)
[0270] 198.3 g (1.0 mol) of 4,4'-diaminodiphenylmethane, 4-( N, N-diallylamino) phenol 378.5g (2.0 moles), after dissolving in 1460g toluene, add 94% paraformaldehyde 127.8g (4.0 moles), heat up to 80°C while stirring, and react at 80°C 7 hours. After the reaction, transfer to a separatory funnel and remove the aqueous layer. Thereafter, the solvent was removed from the organic layer under reduced pressure under heating to obtain 281 g of a benzoxazine compound (A-2).
[0271] 1 H-NMR shows 7.08ppm-6.98ppm (8H), 6.54ppm-6.40 (6H), 5.84ppm-5.74ppm (4H), 5.24ppm (4H), 5.10ppm (8H), 4.48ppm (4H), 3.78 ppm(8H), 3.69ppm(2H) peaks, 13 C-NMR showed 146.2ppm, 145.2ppm, 142.7ppm, 134.8ppm, 133.6ppm, 129.1ppm, 128.9ppm, 121.3ppm, 117.5ppm, 116.4ppm, 116.0ppm, 112.8ppm, 110.9ppm, 78.5ppm, 52.8ppm, 49.5ppm peak, mass spectrum showed M + =624, it was confirmed that the target benzoxazine compound (A-2) represented by the f...
Embodiment 3
[0273] [Example 3] Synthesis of benzoxazine compound (A-3)
[0274] 158.2 g (1.0 moles) of 1,5-diaminonaphthalene, 4-allyloxyphenol 300.4 g (2.0 mol) was dissolved in 1008 g of toluene, 127.8 g (4.0 mol) of 94% paraformaldehyde was added, the temperature was raised to 80° C. while stirring, and the reaction was carried out at 80° C. for 7 hours. After the reaction, transfer to a separatory funnel and remove the aqueous layer. Thereafter, the solvent was removed from the organic layer under reduced pressure under heating to obtain 329 g of a benzoxazine compound (A-3).
[0275] 1 H-NMR shows 7.93ppm (2H), 7.53ppm-7.25ppm (5H), 6.75ppm-6.67ppm (5H), 6.02ppm-5.95ppm (2H), 5.36ppm-5.19ppm (8H), 4.61ppm ( 4H), 4.43ppm (4H) peak, 13 C-NMR showed 152.1ppm, 147.4ppm, 146.2ppm, 134.0ppm, 129.3ppm, 128.2ppm, 125.6ppm, 121.4ppm, 119.5ppm, 117.2ppm, 116.9ppm, 114.6ppm, 112.3ppm, 81.0ppm, 68.5ppm, 51.6ppm peak, mass spectrometry showed M + =506 peak, it was confirmed that the target ...
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