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Perfluoropolyether carboxylic acid compound and preparation method thereof

A technology of perfluoropolyether carboxylic acid and perfluoropolyether, which is applied in the field of polymer compound synthesis, can solve the problems of cumbersome perfluoropolyether carboxylic acid route, discomfort for experimenters, and difficulty in removing potassium salt, and saves the cost of reagents. , the effect of high reaction yield and low price

Pending Publication Date: 2021-10-19
东莞泰岳先进材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Chinese patent CN109071793A discloses a synthetic method of an anti-fingerprint agent. The anti-fingerprint agent is prepared by using perfluoropolyether alcohol through substitution esterification, high-temperature hydrolysis and amidation reaction. The resistance to steel wool and rubber friction of the product reaches 20,000 times respectively And 8000 times, the product performance is better, but the route of preparing perfluoropolyether carboxylic acid is more loaded down with trivial details, and concrete manifestation is that reaction needs to use strong base many times, such as: sodium hydroxide and potassium hydroxide, and the potassium salt formed is post-treated It is difficult to completely remove during the process, and the temperature of the hydrolysis process is high (above 100°C), which has certain dangers
During the synthesis process, tetrahydrofuran and ethylene glycol dimethyl ether with a strong pungent smell are used, which will cause discomfort to the experimenters

Method used

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  • Perfluoropolyether carboxylic acid compound and preparation method thereof
  • Perfluoropolyether carboxylic acid compound and preparation method thereof
  • Perfluoropolyether carboxylic acid compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Add 10g (2.86mmol) to the 100mL three-neck flask equipped with stirring and the average composition is 3 (OCF 2 CF 2 ) p (OCF 2 ) q OCF 2 CH 2 OH perfluoropolyether alcohol (the sum of p and q is 36, the number average molecular weight is 3500, produced by SOLVAY company), 15mL m-ditrifluorotoluene, 0.43g (4.29mmol, 1.5equ) of succinic anhydride, 0.05g ( 0.5wt% dimethylaminopyridine in perfluoropolyether alcohol), heated up to 40°C and stirred for 5 hours, then extracted with water and distilled under reduced pressure to obtain 10.08g of a colorless and transparent product with a yield of 98%. Ether carboxylic acid compound (A 1 ) CF 3 (OCF 2 CF 2 ) p (OCF 2 ) q OCF 2 CH 2 OCOCH 2 CH 2 COOH, the reaction formula is as follows.

[0049]

[0050] where Rf is CF 3 (OCF 2 CF 2 ) p (OCF 2 ) q OCF 2 -.

Embodiment 2

[0052] Add 10g (2.03mmol) average composition to CF in a 100mL three-neck flask equipped with stirring 3 (OCF 2 CF 2 ) p (OCF 2 ) q OCF 2 CH 2 OH perfluoropolyether alcohol (the sum of p and q is 49, the number average molecular weight is 4930, produced by SOLVAY company), 15mL m-ditrifluorotoluene, 0.69g (6.09mmol, 3equ) of glutaric anhydride, 0.2g (2wt % N,N-diisopropylethylamine in perfluoropolyether alcohol), heated to 60°C under reflux and stirred for 4h, and obtained 10.03g of a colorless and transparent product through water extraction and vacuum distillation, with a yield of 98%. That is perfluoropolyether carboxylic acid compound (A 2 ) CF 3 (OCF 2 CF 2 ) p (OCF 2 ) q OCF 2 CH 2 OCOCH 2 CH 2 CH 2 COOH, the reaction formula is as follows.

[0053]

[0054] where Rf is CF 3 (OCF 2 CF 2 ) p (OCF 2 ) q OCF 2 -.

Embodiment 3

[0056] Add 10g (2.86mmol) average composition to CF in a 100mL three-necked flask equipped with stirring 3 (OCF 2 CF 2 ) p (OCF 2 ) q OCF 2 CH 2 OH perfluoropolyether alcohol (the sum of p and q is 36, the number average molecular weight is 3500, produced by SOLVAY company), 25mL m-ditrifluorotoluene, 2.12g (14.29mmol, 5equ) of phthalic anhydride, 0.5g (5wt% in perfluoropolyether alcohol) of dimethylaminopyridine, heated to 80 ° C and stirred for 3 hours, obtained 10.18 g of a colorless and transparent product through water extraction and vacuum distillation, with a yield of 99%, which is perfluoropolyether alcohol. Ether carboxylic acid compound (A 3 ), CF 3 (OCF 2 CF 2 ) p (OCF 2 ) q OCF 2 CH 2 OCOC 6 h 4 COOH, the reaction formula is as follows.

[0057]

[0058] where Rf is CF 3 (OCF 2 CF 2 ) p (OCF 2 ) q OCF 2 -

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Abstract

The invention relates to the technical field of high-molecular compound synthesis, in particular to a perfluoropolyether carboxylic acid compound and a preparation method thereof. The preparation method of the perfluoropolyether carboxylic acid compound comprises the following steps: (1) completely dissolving perfluoropolyether alcohol in a solvent; (2) adding cyclic anhydride and a catalyst, conducting heating to 40-80 DEG C, carrying out a reflux reaction for 2-5 hours, and performing washing with water; and (3) performing reduced-pressure distillation to obtain the perfluoropolyether carboxylic acid compound, wherein the solvent is a fluorine-containing solvent capable of dissolving perfluoropolyether. The preparation method of the perfluoropolyether carboxylic acid compound disclosed by the invention is short in synthetic route, and no strong irritant solvent or metal salt is generated. The perfluoropolyether carboxylic acid compound provided by the invention has high purity, can be subjected to alcoholysis and ammonolysis to generate corresponding ester, amide and other derivatives, can be further used for preparing perfluoropolyether siloxane and other compounds, and is an intermediate with wide application prospects.

Description

technical field [0001] The invention relates to the technical field of polymer compound synthesis, in particular to a perfluoropolyether carboxylic acid compound and a preparation method thereof. Background technique [0002] Perfluoropolyether is a colorless and transparent oily substance whose main chain is composed of -CF 2 -O-CF 2 - Such an ether chain structure has excellent flexibility, heat resistance, chemical stability and non-flammability, and this type of material is very safe. The perfluoropolyether anti-fingerprint technology is mainly to introduce siloxane active groups at the end of the perfluoropolyether chain, and dehydrate and condense with the silicon hydroxyl groups on the surface of the substrate after hydrolysis of siloxane to form a firm -Si-O-Si - bond, thereby introducing a layer of perfluoropolyether coating on the surface of the substrate, endowing the substrate with excellent waterproof, oil-proof, anti-fouling, wear-resistant and scratch-resist...

Claims

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Application Information

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IPC IPC(8): C08G65/332
CPCC08G65/3322
Inventor 曾永昌宫秀明
Owner 东莞泰岳先进材料有限公司
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