Atom transfer radical polymerization ligand with initiating activity, preparation and application thereof
An atom transfer and free radical technology, applied in the field of polymer chemistry, can solve the problems of complex reaction system, oxygen sensitivity, and metal impurities such as copper in the polymer, so as to achieve broad application prospects and simplify the reaction system
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Embodiment 1
[0034] Example 1 Preparation of three (2-bromo-isobutyryloxyethyl)amine (Ia)
[0035] The target compound was prepared from triethanolamine, 2-bromoisobutyryl bromide and triethylamine.
[0036] 2-Bromoisobutyryl bromide (5.75 g, 25 mmol) and dry CH 2 Cl 2 (20 mL) was added to the reaction flask. Under cold water cooling, drop triethanolamine (0.75g, 5mmol), CH 2 Cl 2 (5mL), triethylamine (8mL) mixed solution. After the dropwise addition was completed, the reaction was carried out overnight at room temperature. Filter, discard the solid, wash the filtrate twice with saturated sodium carbonate, extract the aqueous phase once with dichloromethane, combine the dichloromethane phases, wash with saturated brine, and dry over anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by a silica gel column with petroleum ether / ethyl acetate (V / V=6:1) as the eluent to obtain a pale yellow oily liquid (2.56 g, 86%).
[0037] IR: v(cm -1 )3342, 2977, 174...
Embodiment 2
[0041] Example 2 Preparation of three (2-chloromethylbenzoyloxyethyl) amine (IIa)
[0042] Weigh p-chloromethylbenzoic acid (5.40g, 30mmol) into a 100ml flask, add 40mL of thionyl chloride, add 1-2 drops of N,N-dimethylformamide, and heat to reflux for 3 hours. After the reaction, the excess thionyl chloride was evaporated, the residue was cooled with cold water, and triethanolamine (0.75g, 5mmol), CH 2 Cl 2 (5mL), triethylamine (8mL) mixed solution. After the dropwise addition was completed, the reaction was carried out overnight at room temperature. The solid part was removed by filtration, and the filtrate was washed twice with saturated sodium carbonate and saturated brine respectively, and dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was purified by a silica gel column with petroleum ether / ethyl acetate (V / V=4:1) as the eluent to obtain a pale yellow oily liquid (2.46 g, 81%).
[0043] IR: v(cm -1 )3040, 2961, 1740, 1613, 1482, 141...
Embodiment 3
[0047] Example 3 Utilize the tris (2-bromo-isobutyryloxyethyl) amine (Ia) prepared in Example 1 to carry out the ATRP emulsion polymerization of methyl methacrylate (MMA)
[0048] Add CuBr to a 25 mL round bottom flask (previously treated with glacial acetic acid to remove possible CuBr 2 Impurities) (0.0022g, 0.015mmol), compound (Ia) (0.019g, 0.034mmol), MMA (0.10g, 1.0mmol), stirred until dissolved. Add Span-80 emulsifier (0.10 g, 0.23 mmol) into the round bottom flask and stir evenly, then add 10 mL of distilled water, stir for 30 min, vacuumize under freezing conditions, and blow nitrogen, repeat 3 times. The system was placed in an oil bath at 60°C and reacted for 10 minutes, and MMA (1.0 g, 10 mmol) was added to continue the reaction for 9 hours. During the reaction, samples were taken at regular intervals to track the progress of the reaction.
[0049] After the reaction, use lower alcohol to break the emulsion, and the mixture passes through neutral Al 2 o 3 The c...
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