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Atom transfer free radical polymerization initiator with gemini surface activity and synthetic method thereof

A technology of gemini surface activity and polymerization initiator, applied in the field of chemistry, can solve the problems of poor water resistance of polymers, inconvenient operation, affecting the optical, electrical and surface properties of products, etc. body wide effect

Inactive Publication Date: 2012-06-20
JIANGXI SCI & TECH NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these living free radical emulsion polymerizations generally require the use of corresponding initiators and traditional small molecule emulsifiers at the same time, which brings inconvenience to the operation, and the small molecule emulsifiers will eventually enter the polymer product, bringing the product Adverse effects, for example, small molecule emulsifiers will migrate to the surface, degrade the water resistance of the polymer, and affect the optical, electrical and surface properties of the product, etc.

Method used

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  • Atom transfer free radical polymerization initiator with gemini surface activity and synthetic method thereof
  • Atom transfer free radical polymerization initiator with gemini surface activity and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

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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Abstract

The invention discloses an atom transfer free radical polymerization initiator with gemini surface activity. A synthetic method of the initiator comprises the following steps of: undergoing an esterification reaction on halogenated carboxylic acid, a derivative thereof and N,N-dimethylethanolamine serving as raw materials; and undergoing a substitution reaction on dihalide to obtain a compound. The synthetic method is simple, is easy and convenient to operate, has a wide monomer application range, and has a wide application prospect in soap-free emulsion polymerization.

Description

technical field [0001] The invention relates to the field of chemistry, in particular to an atom transfer radical polymerization (ATRP) initiator with Gemini surface activity and a synthesis method thereof. Background technique [0002] Living / Controlled Radical Polymerization (L / CRP) has many advantages such as wide range of applicable monomers, easy to realize reaction conditions, can be carried out in different systems such as water, and the obtained polymer has controllable molecular weight and distribution. Living / controlled radical polymerization (L / CRP) mainly includes atom transfer radical polymerization (ATRP), reversible addition-fragmentation chain transfer polymerization (RAFT), nitroxide radical mediated polymerization (NMP), etc. (Ouchi, M; Terashima, T; Sawamoto, M. Acc. Chem. Res .2008, 41 , 1120-1132.). In order to realize living / controllable free radical polymerization, in addition to suitable monomers in the reaction system, suitable catalysts, initiato...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C219/06C07C219/14C07C213/08C08F20/14C08F293/00C08F212/08C08F220/40C08F2/28
Inventor 申亮程传杰
Owner JIANGXI SCI & TECH NORMAL UNIV
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