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Acrylic ester containing perfluoropolyether chain and synthetic method thereof

A technology of perfluoropolyether and acrylate, which is applied in chemical instruments and methods, preparation of sulfonamide, preparation of carboxylic acid amide, etc., can solve problems such as adverse effects

Inactive Publication Date: 2017-06-30
JIANGSU LEE & MAN CHEM +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Current research has proved that long-chain perfluoroalkyl compounds have adverse effects on the environment, humans and animals, and acrylates containing monofluorine chains have certain limitations on the adjustment of polymer properties

Method used

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  • Acrylic ester containing perfluoropolyether chain and synthetic method thereof
  • Acrylic ester containing perfluoropolyether chain and synthetic method thereof
  • Acrylic ester containing perfluoropolyether chain and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] The structure of the acrylate containing perfluoropolyether chain synthesized in this embodiment is as follows:

[0061]

[0062] where Rf- is:

[0063]

[0064] 1) Synthesis of N-hydroxyethyl perfluoropolyether sulfonamide

[0065] Add 10.4g (0.1mol) of N-hydroxyethylethylenediamine, 50ml of anhydrous ether, and 50ml of methyl acetate into a 500ml reaction bottle, slowly add 142.4g (0.2mol) of all After the addition of methyl fluoropolyether sulfonate was completed, the ice-water bath was removed, and the reaction was continued for 10 hours. Then, the low-boiling components were removed by distillation with a rotary evaporator, and the intermediate N-hydroxyethyl perfluoropolyether sulfonamide was obtained after vacuum drying.

[0066] ) Synthesis of acrylates containing perfluoropolyether chains

[0067] Add 100ml of dichloromethane and 10.8g (0.105mol) of triethylamine to the above-mentioned reaction flask equipped with N-hydroxyethyl perfluoropolyether sulfo...

Embodiment 2

[0075] The structure of the acrylate containing perfluoroether chain synthesized in this embodiment is as follows:

[0076]

[0077] where Rf- is:

[0078]

[0079] 1) Synthesis of N-hydroxyethyl perfluoropolyetheramide

[0080] Add 14.7g (0.1mol) of N-hydroxyethyldiethylenetriamine and 100ml of dichloromethane into a 500ml reaction bottle, and slowly add 153.2g (0.3mol) of perfluoropolyether formic acid methyl in an ice-water bath while stirring After the addition of the ester, the ice-water bath was removed, and the reaction was continued for 10 hours, and then the low-boiling components were removed by distillation with a rotary evaporator, and the intermediate N-hydroxyethyl perfluoropolyetheramide was obtained after vacuum drying. The structure of ethyldiethylenetriamine is as follows:

[0081]

[0082] 2) Synthesis of acrylates containing perfluoropolyether chains

[0083] Add 100ml of anhydrous ether and 10.8g (0.105mol) of triethylamine to the above-mention...

Embodiment 3

[0092] The structure of the acrylate containing perfluoroether chain synthesized in this embodiment is as follows:

[0093]

[0094] where Rf- is:

[0095]

[0096] 1) Synthesis of N-(2-hydroxypropyl) perfluoropolyetheramide

[0097] Add 11.82g (0.1mol) N-(2-hydroxypropyl)-ethylenediamine and 100ml tetrahydrofuran into a 500ml reaction bottle, slowly add 138.03g (0.2mol) perfluoropolyether dropwise under ice-water bath while stirring Ethyl formate, the dropwise addition is completed, remove the ice-water bath, continue the reaction for 10h, then use the rotary evaporator to distill off the low boiling point components, and obtain the intermediate N-(2-hydroxypropyl) perfluoropolyetheramide after vacuum drying, wherein The N-(2-hydroxypropyl)-ethylenediamine structure used is as follows:

[0098]

[0099] 2) Synthesis of acrylates containing perfluoropolyether chains

[0100] Add 100ml of chloroform and 13.57g (0.105mol) of N,N-diisopropylethylamine to the reaction ...

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Abstract

The invention discloses an acrylic ester containing a perfluoropolyether structure. The structure general formula of the acrylic ester is as shown in the Figure I, wherein Rf is a perfluoropolyether group; R' is a bivalent CO or SO2 group; R1 and R3 are the same or different C2-C6 bivalent alkyl groups; R2 and R4 are H or C1-C3 monovalent alkyl groups; n is the integer greater than or equal to 0. The Figure I is as shown in the specification. The synthetic method for the acrylic ester containing the perfluoropolyether comprises the following steps: 1) enabling N-hydroxyalkylamine compound to react with a derivative of perfluoropolyether substituted formic acid or a derivative of perfluoropolyether substituted sulfonic acid to obtain N-hydroxyalkyl perfluoropolyether amide or N-hydroxyalkyl perfluoropolyether sulfamide; and 2) under the production of nitrogen, slowly adding propylene acyl halide or 2-alkyl propylene acyl halide to the N-hydroxyalkyl perfluoropolyether amide or the N-hydroxyalkyl perfluoropolyether sulfamide dropwise, reacting for 1-5 hours, to obtain an acrylic ester compound containing the perfluoropolyether chain. The acrylic ester containing the perfluoropolyether chain synthesized by using the method has the characteristics of simple technology, and high product yield and purity, and can be applied for the synthesis of a fluorine-containing acrylic resin or other fluorine-containing materials.

Description

technical field [0001] The invention belongs to the field of acrylate monomers, in particular to a fluorine-containing acrylate monomer and a synthesis method thereof. Background technique [0002] Fluorine-containing acrylate monomer is an important monomer in the synthesis of water and oil repellent materials, and has been widely used due to its excellent surface properties and repellent function. The Chinese patent CN1946668A of Daikin Corporation of Japan discloses a method for synthesizing fluorine-containing acrylate, which uses fluoroalkyl alcohol as a raw material to perform esterification reaction with acrylic acid compound at high temperature to synthesize fluorine-containing acrylate. U.S. Patent No. 3,719,698 uses acrylic acid or methacrylic acid to react with trifluoroacetic anhydride, and then adds fluorine-containing alkyl alcohol to the resulting compound to generate fluorine-containing acrylate. Chinese patent CN1871207A1 discloses a method for the synthesi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C303/38C07C311/24C07C231/02C07C235/10
CPCC07C231/02C07C303/38C07C311/24C07C235/10
Inventor 王江兵梁海波陈亿新谢文建陈新滋
Owner JIANGSU LEE & MAN CHEM
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