Polymerizable photosensitive monomer, photosensitive polymer based on polymerizable photosensitive monomer, and biological material surface modification method
A photosensitive polymer and photosensitive technology, which is applied in the preparation of amino hydroxyl compounds, chemical instruments and methods, and the preparation of organic compounds, can solve the problems of production safety impact and complex process, and achieve controllable structure, simple preparation process, and improved Effects of Photoinitiation Efficiency and Photocuring Efficiency
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preparation example 1
[0091] Preparation Example 1: Synthesis of Polymerizable Photosensitive Monomer
[0092] Weigh 2.54g (10mmol) of 4-(2,3-epoxypropoxy)benzophenone and dissolve it in 50mL of ethanol and place it in a flask. Under stirring conditions, 1.55g (26mmol) of 2-(methyl Amino) ethyl acrylate was added dropwise into the flask, and after the drop was completed, the temperature was raised to 75° C., and the reaction was continued for 4 hours. Add dilute hydrochloric acid into the flask, extract with benzene, collect the aqueous phase and adjust the pH value to 7-8, extract with chloroform, dry the organic phase with anhydrous magnesium sulfate, filter and rotary evaporate to remove the solvent, and distill the solvent with ethyl acetate and n-hexane Alkane was used as eluent, and after purification by column chromatography, 2.12 g of light yellow viscous liquid was obtained with a yield of 56%. H NMR spectrum ( 1 H NMR) δ (ppm): 7.1-7.8 (9H, benzene ring), 6.42 (1H, CH=CH 2 ), 6.13 (1H,...
preparation example 2
[0095] Preparation Example 2: Synthesis of Active Monomer A
[0096] Dissolve 11.6g (0.1mol) of hydroxyethyl acrylate in 100mL of dichloromethane, and add 22.3g (0.11mmol) of p-nitrophenyl chloroformate in dichloromethane dropwise to the flask under ice-cooling conditions , after dripping, it was raised to room temperature, and the reaction was continued for 18 hours. with saturated NaHCO 3 , 1M HCl and deionized water wash the reaction solution, collect the organic phase and dry it with anhydrous magnesium sulfate; use ethyl acetate and n-hexane as eluents, obtain 22.3g light yellow viscous liquid after purification by column chromatography, namely Active monomer A, yield 79%. H NMR spectrum ( 1 H NMR) δ (ppm): 7.6-8.3 (4H, benzene ring), 6.41 (1H, CH=CH 2 ), 6.12 (1H, CH 2 =CH-), 5.84 (1H, -CH=CH 2 ), 4.38-4.39 (4H, -O-CH 2 -CH 2 -O-). The chemical reaction structure is as follows:
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preparation example 3
[0098] Preparation Example 3: Synthesis of Active Monomer B
[0099] Take 11.5g (0.1mol) of N-hydroxysuccinimide and dissolve it in 80mL of dichloromethane, add 15.8g (0.11mmol) of acryloxypropionic acid and 22.67g (0.11mol) of DCC dichloromethane dropwise solution at room temperature for 20 hours. The reaction solution was sequentially washed with saturated NaHCO 3 Wash with deionized water, and the organic phase is dried with anhydrous magnesium sulfate; With ethyl acetate and normal hexane as eluent, obtain 18.6g colorless viscous liquid after column chromatography purification, be active monomer B, produce rate of 77%. H NMR spectrum ( 1 H NMR) δ (ppm): 6.43 (1H, CH=CH 2 ), 6.12 (1H, CH 2 =CH-), 5.83 (1H, -CH=CH 2 ), 4.42 (2H, -O-CH 2 -CH 2 -), 2.64 (4H, -CH 2 -CH 2 -), 2.52 (2H, -O-CH 2 -CH 2 -). The chemical reaction structure is as follows:
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