Atom transfer free radical polymerization initiator with gemini surface activity and synthetic method thereof
A Gemini surface active and polymerization initiator technology, applied in the chemical field, can solve the problems of inconvenient operation, affecting the optical, electrical and surface properties of products, and poor water resistance of polymers, etc., achieving easy operation, wide range of applicable monomers, The effect of simple synthesis method
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Embodiment 1
[0024] Example 1 N 1 ,N 6 -Bis(2-(2-bromoisobutyryloxy)ethyl)- N 1 ,N 1 ,N 6 ,N 6 -Tetramethylhexane-1,6-diammonium bromide (compound I-a )Synthesis
[0025] Add 20 mL (0.3 mmol) dichloromethane (DCM), 4.45 g (50 mmol) N,N - Dimethylethanolamine, 9 mL (63 mmol) triethylamine (TEA). Magnetic stirring, fully stirring to dissolve and mix well. At room temperature, 7.5 mL (60 mmol) of 2-bromoisobutyryl bromide was slowly added dropwise to the reaction solution. After dripping, react for 2 h. Filter to remove solids. After the filtrate was concentrated, ethyl acetate was added to dissolve it, washed with water, and saturated with Na 2 CO 3 Wash, anhydrous Na 2 SO 4 Dry and distill under reduced pressure to obtain the product II-a (9.05 g, 86.1%). 1 H NMR (400 MHz, CDCl 3 ): δ 4.29 (2H, d, J= 4 Hz), 2.64 (2H, d, J = 4 Hz), 2.32 (6H, s), 1.94 (6H, s); 13 C NMR (100 MHz, CDCl 3 ): δ 171.5, 64.1, 57.2, 55.7, 45.7, 30.7;
[0026] Under nitrogen protection,...
Embodiment 2
[0031] Example 2 N 1 ,N 4 - Bis[(4-chloromethylbenzoyloxy)ethyl]- N 1 ,N 1 ,N 4 ,N 4 -Tetramethylhexane-1,4-diammonium bromide (compound I-b ) Synthesis
[0032] 4-Chloromethylbenzoic acid (10.53 g, 60 mmol) was dissolved in thionyl chloride (40 mL), and a catalytic amount of N,N -Dimethylformamide (DMF), refluxed for 5 h, concentrated. The residue was dissolved in anhydrous tetrahydrofuran (20 mL), and added dropwise to N,N -Dimethylethanolamine (4.45 g, 50 mmol) and pyridine (4.98 g, 63 mmol) in THF. After dropping, react at room temperature for 3 h. Then proceed in a similar manner to Example 1 to obtain an intermediate II-b (9.21 g, 76.2%). 1 H NMR (400 MHz, CDCl 3 ): δ 8.04 (d, 2H), 7.46 (d, 2H), 4.62 (s, 2H), 4.28 (d, 2H), 2.64 (d, 2H), 2.32 (s, 6H); 13 C NMR (100 MHz, CDCl 3 ): δ 166.1, 142.3, 130.3, 130.0, 128.4, 64.2, 57.2, 55.7, 46.3, 45.7;
[0033] Under nitrogen protection, the intermediate II-b (3.38 g, 14 mmol), 10 mL of acetone...
Embodiment 3
[0038] Example 3 N- {4-[((2-bromoisobutyryloxy)ethyl)dimethylaminomethyl]benzoylbenzyl}-2-(2-bromoisobutyryloxy)- N,N -Dimethylethaneammonium bromide (compound I-c ) Synthesis
[0039] First prepare the intermediate according to the same method as in Example 1 II-a ,
[0040] 4,4'-Bis(bromomethyl)benzophenone was then prepared. Dissolve 4,4'-dimethylbenzophenone (1.5 g, 7.1 mmol) and carbamide peroxide (1.47 g, 15.7 mmol) in dichloromethane (20 mL), reflux, and illuminate with a 100 W incandescent lamp , then hydrobromic acid (2.9 mL, 14.3 mmol) was added dropwise, and the reaction was continued for 30 min after the drop was completed. Cool, add deionized water to the reaction solution, separate the liquids, dry the organic phase with anhydrous sodium sulfate, filter, and spin dry the solvent to obtain a white solid, then recrystallize with absolute ethanol to obtain the product 4,4'-bis(bromo Methyl)benzophenone (1.20 g, 46%). M.p. 120-122 o C.IR: ν (cm -1 ) 305...
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