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Fluorocarbon surface active agent and preparation method thereof

A technology of fluorocarbon surfactants and active agents, which is applied in the field of fluorocarbon surfactants and its preparation, and can solve the problems of low surface activity and application limitations of branched products

Active Publication Date: 2014-06-04
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The production process of this type of branched fluorocarbon surfactant is simple and the cost is relatively cheap, but because the surface activity of the branched chain product is not high, its application is greatly restricted

Method used

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  • Fluorocarbon surface active agent and preparation method thereof
  • Fluorocarbon surface active agent and preparation method thereof
  • Fluorocarbon surface active agent and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] Embodiment 1: the synthesis of fluorine-containing intermediate organic acid compound 3

[0071]

[0072] 2.14g of p-bromomethylbenzoic acid, 0.61g of DMAP and 4.12g of DCC were sequentially added into a 100mL jacketed reaction tube. After three times of ventilation, 50mL of anhydrous dichloromethane was added in an ice-water bath, and stirred for a while. Excess methanol was added to the system, and the system was moved to room temperature for reaction after the drop was completed, and the reaction was monitored by TLC. After 5 hours the reaction was complete. System filtration, filtrate successively with KHSO 4 solution, deionized water and saturated brine. The organic phase was dried over anhydrous sodium sulfate, filtered, and the solvent was removed. Finally, the mixture was passed through a silica gel column with an eluent of EA:PE=1:20 to obtain 1.942g of compound 1.

[0073] 1 H NMR (CDCl 3 ,300MHz): δ(ppm)3.92(s,CH 3 ,3H),4.50(s,CH 2 ,2H),7.44-7.48(d...

Embodiment 2

[0079]Example 2: Synthesis of anionic fluorocarbon surfactants containing branched fluorocarbon chains

[0080]

[0081] 3.6 g of compound 3 was dissolved in 20 mL of tetrahydrofuran, and lithium hydroxide aqueous solution was slowly added dropwise until the system pH=7-8. After dropping, the mixed system was spin-dried to obtain a viscous solid. The solid was washed and filtered with acetone, the filter cake was dissolved with methanol, and the solvent was removed to obtain 3.1 g of white powdery anionic fluorocarbon surfactant.

[0082] 1 H NMR (CD 3 OD,300MHz):δ(ppm)3.71(s,CH 2 ,2H),7.30-7.37(d,J=8.4Hz,Ar-H,2H),7.86-7.93(d,J=8.4Hz,Ar-H,2H); 19 F NMR (CD 3 OD,282MHz,):δ(ppm)-63.68~-63.90(m,6F),-81.98~-82.14(t,3F),-106.90~-107.20(m,2F),-124.05~-124.40(m ,2F). 13 C NMR (CD 3 OD,100MHz,):δ(ppm)33.32,110~127,130.12,132.18,134.28,139.15,174.80;LRMS(EI):454,437.Anal.Calcd for C 14 h 6 f 13 LiO 2 :Li,1.51.Found:Li,1.48.

Embodiment 3

[0083] Example 3: Synthesis of quaternary ammonium salt cationic fluorocarbon surfactants containing branched fluorocarbon chains

[0084]

[0085] Add 5g of compound 3, 0.675g of DMAP and 4.2g of EDCI in sequence in a 100mL jacketed reaction tube,

[0086] After pumping and exchanging air three times, add 50 mL of dichloromethane under an ice-water bath, and stir for a while. Add excess N,N-dimethylethylenediamine to the system, and after the drop is complete, the system is moved to room temperature for reaction. The reaction was monitored by TLC, and the reaction was completed after 5 hours.

[0087] The system was washed successively with deionized water and saturated brine. The organic phase was dried over anhydrous sodium sulfate, filtered, and the solvent was removed. Finally, the mixture was passed through a silica gel column with dichloromethane:methanol:triethylamine=20:1:a small amount of eluent to obtain 5.126g of compound 7.

[0088] 1 H NMR (DMSO-d 6 ,300...

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Abstract

The invention relates to a fluorocarbon surface active agent containing CF3CF2CF2C(CF3)2 groups and a preparation method thereof. The preparation method comprises the following steps: carrying out nucleophilic substitution on perfluor-2-methyl-2-amylene as an initial raw material and benzyl bromine to prepare a fluorine-containing middle body carboxylic acid, and neutralizing the carboxylic acid and an alkaline solution to obtain an anionic fluorocarbon surface active agent; blending the carboxylic acid and amine to prepare a fluorine-containing middle body amide, and reacting the amide with alkyl halide, sodium chloroacetate or biphenyl benzylidene chloride to obtain a quaternary ammonium salt cation fluorocarbon surface active agent, a glycine betaine amphoteric fluorocarbon surface active agent or a double fluorocarbon surface active agent correspondingly. The method provided by the invention has the advantages that the raw materials are easily available, the technology is simple, the price is low, the repeatability is good, and the surface tension property of the product is good.

Description

technical field [0001] The invention belongs to a fluorocarbon surfactant and a preparation method thereof, in particular to a preparation technology of an environment-friendly high surface tension active fluorocarbon surfactant containing branched fluorocarbon chains. Background technique [0002] Fluorocarbon surfactants are the most important varieties of special surfactants. In many fields with special requirements, there are many irreplaceable important uses of hydrocarbon surfactants. [0003] The unique properties of fluorocarbon surfactants are often summarized as "three highs" and "two phobias", that is, high surface activity, high heat resistance stability and high chemical stability; its fluorine-containing hydrocarbon group is both water-repellent and oil-repellent. [0004] Fluorocarbon surfactants have high heat resistance and high chemical stability. They can resist the effects of strong oxidants, strong acids and strong alkalis, and can still maintain good su...

Claims

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Application Information

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IPC IPC(8): B01F17/00B01F17/22B01F17/18C07C63/70C07C51/41C07C233/78C07C231/12C09K23/00C09K23/18C09K23/22
Inventor 姜标沙敏潘仁明
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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