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Fluorine-containing phosphate surfactant and preparation method thereof

A surfactant, fluorine-containing phosphoric acid ester technology, applied in chemical instruments and methods, dissolution, chemical/physical processes, etc., can solve the problems of low bioaccumulation, difficult to obtain raw materials, and many reaction steps, and achieve the reaction yield. High, cheap raw materials, simple method

Active Publication Date: 2016-08-10
DONGGUAN DONGYANG SOLAR SCI RES & DEV CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The branched fluorocarbon surfactant developed with hexafluoropropylene trimer as raw material is easy to degrade under various physical and chemical conditions, and has low bioaccumulation. It is an ideal substitute for PFOS / PFOA. Reported ethylene, tetrafluoroethylene, perfluoroalkyl iodide telomerization in US8049040 B2, and then through a series of reaction steps to prepare the technological process of ethylene-tetrafluoroethylene phosphate composition fluorocarbon anion surfactant, the surface activity of this patent obtained The surface performance of the agent is excellent, but the telomerization process of ethylene, tetrafluoroethylene, and perfluoroalkyl iodide is complex and the yield is low, resulting in high cost and difficult industrialization. Patent US20110092410A1 reports the preparation of perfluoroalkane with hexafluoropropylene dimer as raw material A new process for phosphate-based fluorocarbon anionic surfactants, but the process has too many reaction steps, complicated process, and expensive reagents such as cesium fluoride and propylene bromide are used, and the production cost is relatively high. Patent WO 9104978 (JP 3123786 A ) reported a preparation method of monophosphate fluorocarbon anion surfactant, but the raw material does not have ω-H fluorinated alkyl alcohol, the raw material is difficult to obtain, and the production cost is high

Method used

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  • Fluorine-containing phosphate surfactant and preparation method thereof
  • Fluorine-containing phosphate surfactant and preparation method thereof
  • Fluorine-containing phosphate surfactant and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0031] Add 30mL of acetonitrile, 6.22g (0.01mol) of 4-perfluorononenyloxybenzenesulfonyl chloride, 0.75g (0.01mol) of 2-methylaminoethanol, 1.06g (0.01mol) of anhydrous carbonic acid in a 100mL four-necked flask Sodium, stir, heat up to 0°C, keep the temperature and stir for 2h, distill the reaction solution under reduced pressure until no solvent comes out, cool to room temperature, wash the viscous oil obtained with water, and recrystallize with acetonitrile to obtain white crystal N-hydroxyethyl -N-methyl-4-perfluoroalkenyloxybenzenesulfonamide, yield 85%, the gained N-hydroxyethyl-N-methyl-4-perfluoroalkenyloxybenzenesulfonamide is equipped with a stirrer , a condenser tube, and a 250mL four-necked flask with a thermometer, start the stirrer and raise the temperature to 30°C, add 3.55g of phosphorus pentoxide in batches, the temperature will gradually increase, and the reaction will start, and the reaction temperature will be maintained at 30°C. After 24 hours, the tempera...

Embodiment 2

[0033]Add 30mL of dichloromethane, 6.22g (0.01mol) of 4-perfluorononenyloxybenzenesulfonyl chloride, 3.75g (0.05mol) of 2-methylaminoethanol, 4.04g (0.04mol) of trichloromethane into a 100mL four-necked flask Ethylamine, stirred, heated up to 80°C, kept at the temperature and stirred for 12 hours, the reaction solution was distilled under reduced pressure until no solvent came out, cooled to room temperature, washed with water, and recrystallized with acetonitrile to obtain white crystal N-glycolic acid Base-N-methyl-4-perfluoroalkenyloxybenzenesulfonamide, yield 98.7%, gained N-hydroxyethyl-N-methyl-4-perfluoroalkenyloxybenzenesulfonamide is equipped with stirring In a 250mL four-neck flask with a condenser, a condenser, and a thermometer, start the stirrer and raise the temperature to 80°C, add 3.55g of phosphorus pentoxide in batches, the temperature will gradually rise, and the reaction will start. Keep the reaction temperature at 90-110°C. ℃, the reaction time is 6h, the ...

Embodiment 3

[0035] In a 100mL four-necked flask, add 30mL N,N-dimethylformamide, 6.22g (0.01mol) 4-perfluorononenyloxybenzenesulfonyl chloride, 1.5g (0.02mol) 2-methylaminoethanol, 6.9 g (0.05mol) of anhydrous potassium carbonate, stirred, heated up to 150°C, kept at the temperature and stirred for 6 hours, distilled the reaction solution under reduced pressure until no solvent came out, cooled to room temperature, washed the obtained viscous oil, recrystallized with acetonitrile, Obtain white crystal N-hydroxyethyl-N-methyl-4-perfluoroalkenyloxybenzenesulfonamide, yield 93%, the gained N-hydroxyethyl-N-methyl-4-perfluoroalkenyloxy Benzenesulfonamide is in a 250mL four-necked flask equipped with a stirrer, a condenser, and a thermometer, and the temperature of the stirrer is raised to 200°C, and 3.55g of phosphorus pentoxide is added in batches, and the temperature gradually increases, and the reaction starts. The reaction temperature is maintained at 180-200°C, the reaction time is 10h, ...

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Abstract

The invention discloses a fluorine-containing phosphate surfactant and a preparation method thereof. The preparation method comprises that 4-perfluoroalkenoxybenzene sulfonyl chloride and 2-methylaminoethanol as raw materials undergo a reaction in an organic solvent in the presence of an acid binding agent at a temperature of 0-150 DEG C for 2-12h, the product is treated to form N-ethoxy-N-methyl-4-perfluoroalkenoxybenzsulfamide, the N-ethoxy-N-methyl-4-perfluoroalkenoxybenzsulfamide and an inorganic phosphorus compound are mixed and undergo a reaction at a temperature of 30-200 DEG C for 2-24h, an alkali liquid is added into the reaction product and undergoes a reaction, the reaction solution is separated and the precipitates are subjected to dewatering and drying so that the fluorine-containing phosphate surfactant is obtained. The preparation method has simple processes. The fluorine-containing phosphate surfactant has excellent performances, a high reaction yield, low surface tension, high activity, good water and oil resistance, wettability, emulsibility and good environmental friendliness and can be used as an emulsifier and a wetting agent in an actual life.

Description

technical field [0001] The invention relates to the field of surfactants, in particular to a fluorine-containing phosphate surfactant and a preparation method thereof. Background technique [0002] Due to the special properties of "three highs and two phobias", fluorosurfactants have attracted more and more attention from people. They are currently the most active category of all surfactants. They are mainly used in special occasions with high technical requirements or in general In areas where surfactants are difficult to perform and have poor application effects, its fluorine-containing hydrocarbon group is both hydrophobic and oil-repellent [New Chemical Materials, 2004, 32(8): 46]. In the 21st century, fluorine-containing surfactants are gradually developing in the direction of environmental friendliness, high surfactant and low cost. The development of fluorine-containing surfactants abroad and in my country is mainly based on 8-carbon perfluorooctyls as raw materials ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01F17/20B01F17/26B01F17/42C09K23/20C09K23/26C09K23/42
CPCC09K23/14
Inventor 梁任龙冯海兵张少凯肖琪程珍
Owner DONGGUAN DONGYANG SOLAR SCI RES & DEV CO LTD
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