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Sulfonate-type fluorosilicone anionic surfactant and preparation method thereof

A surfactant and sulfonate-type technology, which is applied in the field of sulfonate-type fluorosilicon anionic surfactant and its preparation, can solve environmental and human health hazards, perfluorooctane sulfonic acid difficult hydrolysis, photolysis or Microbial degradation and other problems, to achieve the effect of expanding the application range, good water solubility and biodegradability

Active Publication Date: 2019-01-11
JIUJIANG UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The purpose of the present invention is to provide a sulfonate type fluorosilicon anionic surfactant and a preparation method thereof, which solves the problem that existing perfluorooctanesulfonic acid (PFOS) and perfluorooctanoic acid (PFOA) exist in the environment and are difficult to be hydrolyzed, Photolysis or microbial degradation, and enter human and animal tissues through the food chain and accumulate in organisms, causing great harm to the environment and human health

Method used

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  • Sulfonate-type fluorosilicone anionic surfactant and preparation method thereof
  • Sulfonate-type fluorosilicone anionic surfactant and preparation method thereof
  • Sulfonate-type fluorosilicone anionic surfactant and preparation method thereof

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preparation example Construction

[0029] A kind of preparation method of sulfonate type fluorosilicon anionic surfactant, such as Figure 1-4 Shown, this preparation method comprises the following steps:

[0030] (1) Add 20mL of ethyl acetate and 1.78g of N-methallylamine to a 50mL four-necked flask equipped with a stirrer, thermometer, dropping funnel and reflux condenser, which is equipped with anhydrous CaCl 2 Drying tube, the concentration of the 1.78g N-methylallylamine is 0.025mol, gradually drop 4.02g perfluorohexylsulfonyl fluoride at room temperature, the concentration of the 4.02g perfluorohexylsulfonyl fluoride is 0.01mol, control After 30 minutes of dropwise addition, continue to stir and react at 40°C for 2 hours; after stopping the reaction, pour the reaction solution into 100mL water, remove the lower layer of light yellow liquid after layering, and successively wash with 50mL 5% HCl aqueous solution, 30mL saturated NaCO 3 Wash with aqueous solution and 2×30mL water, and dry over anhydrous sodi...

Embodiment 1

[0036] A kind of preparation method based on sulfonate type fluorosilicon anionic surfactant of the present embodiment comprises the following steps:

[0037] (1) Synthesis of NSF6

[0038] Equipped with a stirrer, thermometer, dropping funnel and reflux condenser (anhydrous CaCl 2 Add 20mL of ethyl acetate and 1.78g (0.025mol) of N-methallylamine into a 50mL four-necked flask, and gradually add 4.02g (0.01mol) of perfluorohexylsulfonyl fluoride dropwise at room temperature for about 30min. After the addition was complete, the stirring reaction was continued at 40°C for 2h. After stopping the reaction, pour the reaction solution into 100mL water, remove the light yellow liquid in the lower layer after layering, and wash with 50mL 5% HCl aqueous solution, 30mL saturated NaCO 3 Wash with aqueous solution and 2×30mL water, and dry over anhydrous sodium sulfate to obtain a light yellow transparent liquid with a yield of 91.8% (calculated as perfluorohexylsulfonyl fluoride).

[...

Embodiment 2

[0062] This embodiment is the same as Embodiment 1, the difference is:

[0063] (2) Synthesis of PSF6A

[0064] Add high hydrogen silicone oil PMHS[2.5g, n(Si-H)=40.85mmol], NSF6[1.08g, n(C=C)=2.45mmol] and toluene 20mL into a 100mL three-neck round bottom flask, and then add The Karstedt catalyst with a concentration of 16.123 g / L was connected to a condensing device and a thermometer, magnetically stirred, and the oil bath was heated to 90°C. When the conversion rate of hydrosilylation reached 6%, AGE [4.40 g, n(C=C)=38.40 mmol] was added, and the reaction was continued until the conversion rate of hydrosilylation reaction was basically constant. It can be seen from Table 1 that when n(PMHS): n(NSF6): n(AGE)=10:0.6:9.4, the cmc and γ of PSF6AS cmc They are 0.12g / L and 32.8mN / m respectively.

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Abstract

The invention discloses a sulfonate-type fluorosilicone anionic surfactant and a preparation method thereof. The preparation method adopts an easily degradable and low-toxic fluorine-containing compound C6F13SO2F as a starting point, and is subjected to bimolecular nucleophilic substitution (SN2) reaction with N-methylallylamine to prepare NSF6, then NSF6 is subjected to a hydrosilylation reactionwith poly(methylhydrosiloxane) (PMHS) and allyl glycidyl ether (AGE) in order, finally, a sulfonation reaction is carried out with NaHSO3 to synthesize the sulfonate-type fluorosilicone anionic surfactant PSF6AS, and the surface tension and critical micelle concentration are determined. Compared with traditional fluorocarbon surfactants, the surfactant has good water solubility and biodegradability, and the surfactant provides a new research method and ideas for development and application of the sulfonate-type fluorosilicone anionic surfactants in China.

Description

technical field [0001] The invention relates to a sulfonate type fluorosilicon anionic surfactant and a preparation method thereof. Background technique [0002] Fluorosilicone anionic surfactant is a new type of surfactant with Si-O-Si as the main chain, grafted with fluorine-containing hydrophobic groups and hydrophilic groups such as sulfonic acid groups or carboxyl groups on the side chain or both ends, according to Depending on the structure of the hydrophilic group, it can be divided into four types: sulfonic acid type, carboxylic acid type, sulfate ester type and phosphate ester type, which have good decontamination, foaming, wetting, emulsifying and dispersing properties. Fluorosilicone anionic surfactants have the advantages of both fluorocarbon surfactants and silicone surfactants. Compared with traditional surfactants, they have unique properties. They have become a research hotspot in the field of materials and are widely used in textiles and oil fields. , build...

Claims

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Application Information

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IPC IPC(8): B01F17/54C07F7/08C08G77/392C08G77/388C08G77/385C09K23/54
CPCC07F7/0889C08G77/385C08G77/388C08G77/392C09K23/00
Inventor 叶志刚占昌朝曹小华
Owner JIUJIANG UNIVERSITY
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