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A sulfur-containing long heterochain perfluoroalkyl enoate and its preparation method

A technology of perfluoroalkyl acrylate and perfluoroalkyl acrylate, which is applied in the field of polymer monomer and fine chemical synthesis, can solve the problem of not being able to provide anti-repellent function, short carbon chain perfluoroalkyl is not rigid and crystallinity, to achieve excellent liquid repellency, easy to degrade, and overcome the effect of not easy to degrade

Active Publication Date: 2018-01-19
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Scientists of fluorine-containing materials have found that short carbon chain perfluoroalkyl groups are not rigid and crystalline, and cannot provide ideal anti-repellent functions due to surface reconstruction when in contact with liquids

Method used

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  • A sulfur-containing long heterochain perfluoroalkyl enoate and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] In this example, 1H, 1H, 2H, 2H-7-thia-perfluoroundecyl methacrylate is synthesized, and the specific steps are as follows:

[0042] 1. Telomerization reaction

[0043] Add 46.9g of nonafluorobutyltetrafluorosulfur bromide, 0.40g of di-tert-butyl peroxide, 0.4g of calcium carbonate and 48g of 1,3-bis(trifluoromethyl)benzene into the reaction kettle, seal it, and pump After vacuuming, fill in nitrogen to replace the air in the reactor, and then vacuumize and replace. A total of 4 replacements were performed.

[0044]After raising the temperature to 45°C, feed tetrafluoroethylene into the reactor to keep warm and stir for reaction. The stirring rate is controlled to be 55 rpm, the feeding speed of tetrafluoroethylene is 12g / hour, and the pressure is 0.48MPa. Stop after 2 hours. Tetrafluoroethylene was introduced, and the reaction was continued for 2 hours. After cooling, the reaction mixture was distilled off under reduced pressure to remove 1,3-bis(trifluoromethyl)ben...

Embodiment 2

[0054] In this example, 1H, 1H, 2H, 2H-7-thia-perfluoroundecyl acrylate is synthesized, and the specific steps are as follows:

[0055] 1. Telomerization reaction

[0056] Add 40g of nonafluorobutyl tetrafluorosulfur chloride, 0.1g of dibenzoyl peroxide, 0.15g of calcium carbonate and 15g of trifluorotoluene solvent into the reaction kettle in turn, seal it, and after vacuuming, fill the reaction kettle with nitrogen replacement The air in the chamber is then vacuumed and replaced. A total of 5 replacements were performed.

[0057] After raising the temperature to 50°C, feed tetrafluoroethylene into the reactor to keep warm and stir for reaction. The stirring rate is controlled to be 55 rpm, the feeding speed of tetrafluoroethylene is 10g / hour, and the pressure is 0.45MPa. Stop after 2 hours. Tetrafluoroethylene was introduced, and the reaction was continued for 3 hours. After cooling, the reaction mixture was distilled off under reduced pressure to remove benzotrifluoride....

Embodiment 3

[0065] In this example, 1H, 1H, 2H, 2H-7-thia-perfluoroundecyl acrylate is synthesized, and the specific steps are as follows:

[0066] 1. Telomerization reaction

[0067] Add 36.3g of nonafluorobutyl tetrafluorosulfur chloride, 0.36g of di-tert-butyl peroxide, 0.4g of calcium carbonate and 45g of trifluorotoluene solvent into the reaction kettle in turn, seal it, vacuumize it, and fill it with nitrogen for replacement reaction The air in the kettle was evacuated and replaced. A total of 5 replacements were performed.

[0068] After raising the temperature to 50°C, feed tetrafluoroethylene into the reactor to keep warm and stir for reaction. The stirring rate is controlled to be 55 rpm, the feeding speed of tetrafluoroethylene is 11g / hour, and the pressure is 0.45MPa. Stop after 2 hours. Tetrafluoroethylene was introduced, and the reaction was continued for 2 hours. After cooling, the reaction mixture was distilled off under reduced pressure to remove benzotrifluoride. The ...

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Abstract

The invention discloses a sulfur-containing long heterochain perfluoroalkyl enoate and a preparation method thereof. Using nonafluorobutyltetrafluorosulfur halide as the end-capping agent, after tetrafluoroethylene undergoes telomerization reaction, the obtained 5-thiaperfluorononyl-1-halogen and ethylene gas are reacted by one-electron addition to obtain 1H,1H,2H,2H‑7‑Thiaperfluoroundecyl‑1‑halogen; esterification with silver enoate to give 1H,1H,2H,2H‑thiaperfluoroundecyl acrylate. The sulfur-containing long heterochain perfluoroalkyl enoate prepared by the invention contains carbon-carbon double bonds that are easy to free radical polymerization, and can be used for preparing fluorine-containing polymers and copolymers. Due to the crystallinity of the long heterochain perfluoroalkyl group, the prepared fluoropolymer has no surface reconstruction phenomenon when in contact with liquid, and can provide excellent liquid repellency. At the same time, the perfluoroalkyl long heterochain contains carbon-sulfur heterobonds, is easy to degrade, has no cumulative toxicity, and is not within the scope of banned fluorine-containing chemicals.

Description

technical field [0001] The invention relates to a sulfur-containing long heterochain perfluoroalkyl acrylate and a preparation method thereof, in particular to a sulfur-containing long heterochain perfluoroalkyl acrylate, a sulfur-containing long heterochain perfluoroalkyl methacrylic acid The ester and the preparation method thereof belong to the technical field of polymer monomer and fine chemical synthesis. Background technique [0002] Fluoroalkyl side chains of fluoropolymers are functional groups that provide low surface energy and water and oil repellency. These functional groups are densely arranged on the surface of the polymer to form a surface that is difficult for liquids to wet. The surface energy of fluoropolymers is determined by the pendant fluoroalkyl groups and has nothing to do with the main chain of the polymer molecule. Therefore, which fluorine-containing side group is used determines the surface properties of the fluorine-containing material. [0003...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C381/00C07C319/20C07C323/12
CPCC07C319/20C07C323/12C07C381/00
Inventor 李战雄刘安琪
Owner SUZHOU UNIV
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