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A kind of methacrylate fluorine-containing monomer and its synthesis method and application

A technology of methacrylic acid and methacryloxy, applied in the field of methacrylate fluorine-containing monomers and their synthesis

Active Publication Date: 2016-08-24
南京拓际生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, there are no literature reports on the synthesis and application of fluorine-containing monomers derived from hexafluoropropylene trimer and having structural fragments of methacrylates and benzoates

Method used

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  • A kind of methacrylate fluorine-containing monomer and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Add 10 mmol of hexafluoropropylene trimer (4.5 g), 11 mmol of (2-hydroxy-3-(methacryloyloxy)) propyl benzoate and 0.045 g of tetrabutyl Ammonium bromide was heated to 40° C. with stirring, and 11 mmol of triethylamine was added dropwise. After the drop was completed, the reaction was continued at an insulated temperature for a total of 10 hours. Transfer the reaction solution to a separatory funnel, add dichloromethane, shake fully and then separate the layers, separate the layers, wash the lower dichloromethane layer with water three times, dry over anhydrous sodium sulfate, filter, evaporate the solvent under reduced pressure, and Silica gel column, with ethyl acetate / petroleum ether volume ratio 1:50 mixture as eluent, methacrylate fluorine-containing monomer benzoic acid (2-perfluorononenyloxy-3-(methacrylic acid) The isolated yield of acyloxy)) propyl ester was 81%.

[0025] 1 H NMR, MS and IR data are described below:

[0026] 1 H NMR (CDCl 3 ) δ ppm; 1.94 (s...

Embodiment 2

[0030] The amount of (2-hydroxy-3-(methacryloyloxy))propyl benzoate was 10 mmol, the catalyst was changed to 0.09 g of benzyltriethylammonium chloride, and other operations were the same as in Example 1. The isolated yield of (2-perfluorononenyloxy-3-(methacryloyloxy))propyl benzoate was 78%.

Embodiment 3

[0032] The organic base was changed to 11 mmol of diisopropylethylamine, the reaction temperature was 70° C., and other operations were the same as in Example 1. The isolated yield of (2-perfluorononenyloxy-3-(methacryloyloxy))propyl benzoate was 78%.

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Abstract

The invention discloses a synthesis method of a methacrylate fluorine-containing monomer propyl (2-perfluorononenyloxy-3-(methylacryloyloxy))benzoate. The method comprises the following steps: mixing a hexafluoropropylene tripolymer, propyl (2-hydroxy-3-(methylacryloyloxy)) benzoate and a catalyst, heating while stirring, dropwisely adding organic alkali, sufficiently reacting, and carrying out separation and purification after-treatment on the reaction solution to obtain the methacrylate fluorine-containing monomer propyl (2-perfluorononenyloxy-3-(methylacryloyloxy))benzoate. The methacrylate fluorine-containing monomer propyl (2-perfluorononenyloxy-3-(methylacryloyloxy))benzoate can be used in a fabric finishing agent.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and in particular relates to a methacrylate fluorine-containing monomer, its synthesis method and application. Background technique [0002] Fabric finishing agent can reduce the surface of the fabric so that the fabric has special properties, such as water and oil repellency, flame retardant and so on. Fluorine-containing fabric finishing agent is an internationally recognized excellent fabric finishing agent with excellent performance and unique uses. Treating the fabric with fluorine-containing fabric finishing agent can form a thin film on the surface of the fabric, thereby showing water and oil repellency; and it is beneficial for the fabric to maintain its original color, good feel and air permeability. Chinese patent CN200580009651.6 discloses a class of fluorine-containing monomers. The fluorine-containing structural units in the fluorine-containing monomers are mainly fluorine-containin...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C67/28C07C69/78D06M15/277
CPCC07C67/28C07C69/78D06M15/277D06M2200/11D06M2200/12
Inventor 沈振陆熊杰石如祥莫卫民胡宝祥
Owner 南京拓际生物科技有限公司