Method for preparing fluorine-containing acrylate

A technology of acrylates and polyfluoroalcohols, which is applied in the preparation of carboxylic acid halides, organic chemistry, textiles and papermaking, etc. It can solve the problems of decreased waterproof and oil-proof performance of copolymers, increased surface energy, and decreased receding dynamic contact angles. , to achieve excellent water and oil repellency, non-bioaccumulation effect

Active Publication Date: 2011-04-13
江苏梅兰化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the corresponding receding dynamic contact angle decreases, the surface energy increases, and the water and oil repellency of the obtained copolymer decreases.

Method used

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  • Method for preparing fluorine-containing acrylate
  • Method for preparing fluorine-containing acrylate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Preparation of 2,2,3,3,4,4,4-heptafluorobutyl acrylate

[0030] Slowly dissolve 7.57g (0.200mol) of sodium borohydride into 71.34g of anhydrous ether at 5-10°C, then slowly add 21.41g (0.100mol) of perfluorobutyric acid dropwise. The reaction was stirred at ~-5°C for 10 h. Then stir while slowly adding 10.0g of water to remove excess sodium borohydride (the amount of water is greater than the amount of reducing agent used, less than 1 / 5 of the total organic phase), this time the liquid into a colloidal substance, then dropwise added 20.0g 10% sodium hydroxide aqueous solution, the colloidal substance slowly forms a granular solid, and the whole process emits a large amount of heat. Keep the system temperature at 5-10 ° C, stir for 30 min and then filter. The filtrate is concentrated in a room temperature bath with a rotary evaporator , to get the crude product, then rectification to obtain 16.59g 2,2,3,3,4,4,4-heptafluoro-1-butanol CF 3 CF 2 CF 2 CH 2 OH, yield 82....

Embodiment 2

[0033] Preparation of 1H,1H-perfluorohexyl methacrylate

[0034] Slowly dissolve 5.68g (0.150mol) of lithium aluminum hydride into 106.72g of anhydrous tetrahydrofuran at 0-5°C, and slowly add 29.28g (0.088mol) of perfluorohexanoyl chloride dropwise. The reaction was stirred at ℃ for 8h. Then slowly add 10.0 g of water under stirring, then add 20.0 g of 10% sodium hydroxide aqueous solution, keep the system temperature at 5-10° C. and stir for 20 min, then filter, and the filtrate is concentrated in a room temperature bath with a rotary evaporator to obtain a crude product. Then rectification gives 22.93g 1H, 1H-perfluoro-1-hexanol CF 3 (CF 2 ) 4 CH 2 OH, yield 86.8%.

[0035] 21.14g (0.070mol) 1H, 1H-perfluoro-1-hexanol, 10.11g triethylamine, 49.95g ether and 0.011g phenothiazine were added in the flask with condenser. Cool and keep the temperature in the flask as At 0°C, 9.70 g (0.093 mol) of methacryloyl chloride was added dropwise. After the dropwise addition, stir ...

Embodiment 3

[0037] Preparation of 1H,1H-2-trifluoromethyl-3-oxaperfluorohexyl acrylate

[0038] Slowly dissolve 3.63g (0.096mol) of lithium aluminum hydride into 92.94g of dioxane at -5 to 0°C, and slowly add 19.58g (0.059mol) of 2-trifluoromethyl-3-oxa Fluorocaproyl fluoride, after the dropwise addition, stir and react at 0-5°C for 6h, then slowly add 10.0g of water under stirring, then add 20.0g of 10% sodium hydroxide aqueous solution, keep the system temperature at 5-10°C, and stir for 15min After filtration, the filtrate was concentrated with a rotary evaporator in a room temperature bath to obtain a crude product, which was then rectified to obtain 16.82 g of 1H, 1H-2-trifluoromethyl-3-oxaperfluoro-1-hexanol CF 3 CF 2 CF 2 OCF (CF 3 )CH 2 OH, yield 89.3%.

[0039] Dissolve 16.09g (0.050mol) of 1H, 1H-2-trifluoromethyl-3-oxaperfluoro-1-hexanol, 7.574g (0.062mol) of N,N-dichloromethane in 79.62g of dichloromethane Add methylaniline and 0.008g of phenothiazine into a flask with a...

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Abstract

The invention belongs to the technical field of textile fabric finishing agents, and relates to a method for preparing an intermediate fluorine-containing acrylate monomer of a water-proof and oil-proof organic fluorine fabric finishing agent. The method is characterized by comprising the following steps of: (1) in the presence of a reducing agent, preparing polyfluoroalcohol by using a perfluoroalkylacyl compound as a raw material; and (2) slowly dripping (methyl) acryloyl chloride to prepare fluorine-containing acrylate in the presence of a catalyst by using the polyfluoroalcohol prepared in the step (1) and using phenothiazine as a polymerization inhibitor. The number of long-chain perfluoroalkyl carbon atoms in the prepared fluorine-containing acrylate is less than 8, and the fluorine-containing acrylate can be degraded and has no biological accumulation. The fluorine-containing acrylate has no hidden dangers of long-chain perfluoroalkyl to destroy the environment and harm human health. Fluorine-containing acrylate copolymer emulsion prepared by using the prepared fluorine-containing acrylate monomer is used as a water-proof and oil-proof finishing agent for textiles, and the finished textiles have excellent water-proof and oil-proof performance.

Description

technical field [0001] The invention belongs to the technical field of fabric finishing agents, and relates to a preparation method of a fluorine-containing comonomer, a fluorine-containing acrylate, of a fluorine-containing acrylate waterproof and oil-repellent organic fluorine fabric finish agent. Background technique [0002] At present, with the development of textiles at home and abroad and the needs of people's lives, people are increasingly calling for the development of new and efficient fabric finishing agents. Organic fluorine fabric finishing agent has excellent ability to impart excellent hydrophobic and oleophobic properties to fabrics. At the same time, due to the large electronegativity and small diameter of its F atom, it can shield the C-F bond. It shows high stability in various environments, and also because of its low concentration and high effect, it keeps the treated fabrics with good hand feeling, excellent air permeability and moisture permeability. ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/653C07C67/14C08F220/18C08F220/22D06M15/277D06M101/06
Inventor 钱厚琴徐荣归刘红阳
Owner 江苏梅兰化工有限公司
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