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Perfluoroalkyltetrafluorosulfurmethylene styrene copolymer and its application

A technology of perfluoroalkyl tetrafluorothiomethyl and perfluoroalkyl thiohalobenzene is applied in the field of textile finishing auxiliaries and the preparation of fluorine-containing materials to achieve the effects of strong activity, improved liquid repellency and mild reaction conditions

Active Publication Date: 2021-07-09
SUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The present invention aims at the problem of environmental accumulation toxicity brought about by long carbon chain perfluoroalkyl groups which are not easy to degrade. Tetrafluorosulfurmethylene is used to directly bond perfluoroalkyl groups to phenyl groups as side groups of copolymers; Fluoroalkyl can provide excellent liquid repellency

Method used

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  • Perfluoroalkyltetrafluorosulfurmethylene styrene copolymer and its application
  • Perfluoroalkyltetrafluorosulfurmethylene styrene copolymer and its application
  • Perfluoroalkyltetrafluorosulfurmethylene styrene copolymer and its application

Examples

Experimental program
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Effect test

Embodiment 1

[0057] In this embodiment, nonafluorobutyl tetrafluoromethylene styrene copolymer type finishing agent is synthesized, and the specific steps are as follows:

[0058] (1) Synthesis of 4-(nonafluorobutyltetrafluorosulfurmethylene)bromobenzene

[0059] In a 250 ml three-neck flask equipped with a magnetic stirrer, a thermometer, a constant pressure dropping funnel, and a reflux condenser, add 5.1 g of p-bromothiophenol, 10.4 g of nonafluoro-1-iodobutane, 0.5 g of copper acetate and 40 g of 1,4-dioxane, stirred and heated to 70°C, the reaction solution turned yellow. Dissolve 7.2 g of benzoyl peroxide in 45 g of 1,4-dioxane, slowly add it dropwise through a constant pressure dropping funnel, and keep it warm for 4 h after the drop is complete. After the reaction was completed, 1,4-dioxane was removed by rotary evaporation under reduced pressure, the resulting precipitate was filtered off, washed with water, dried over anhydrous magnesium sulfate for 8 h, and then rotary evaporat...

Embodiment 2

[0076] In this example, a 4-(tridecafluorohexyltetrafluoromethylene) styrene copolymer type finishing agent was synthesized, and the specific steps were as follows:

[0077] (1) Synthesis of 4-(tridecafluorohexyltetrafluorosulfurmethylene) bromobenzene

[0078] Referring to the synthesis steps of 4-(nonafluorobutylthio)bromobenzene in Example 1, first synthesize 4-(tridecafluorohexylthio)bromobenzene. Add 13.4 g of perfluoroiodohexane when feeding, and use the same amount of other materials to obtain 8.5 g of the product 4-(tridecafluorohexylthio)bromobenzene, yield: 62.0%. product 1 H NMR (400 MHz, CDCl 3 ): δ 7.41 (d, J = 8.4 Hz, 2H, o -H), 7.32 (d, J = 8.4 Hz, 2H, m -H). 19 F NMR (564 MHz, CDCl 3 ): δ -80.78 (3F, CF 3 CF 2 CF 2 CF 2 CF 2 CF 2 S), -86.88 (2F, CF 3 CF 2 CF 2 CF 2 CF 2 CF 2 S), -119.30 (2F, CF 3 CF 2 CF 2 CF 2 CF 2 CF 2 S), -121.54 (2F, CF 3 CF 2 CF 2 CF 2 CF 2 CF 2 S), -122.86 (2F, CF 3 CF 2 CF 2 CF 2 CF 2 CF ...

Embodiment 3

[0094] In this example, a 4-(tridecafluorohexyltetrafluoromethylene) styrene copolymer type finishing agent was synthesized, and the specific steps were as follows:

[0095] (1) Synthesis of 4-(tridecafluorohexyltetrafluorosulfurmethylene) chlorobenzene

[0096] The synthesis steps of 4-(tridecafluorohexyltetrafluoromethylene) chlorobenzene refer to the synthesis steps of 4-(nonafluorobutyltetrafluoromethylene) bromobenzene in Example 1, and the reactants and dosage are: 4 -3.0 g of (tridecafluorohexylthio)chlorobenzene, 5.8 g of potassium fluoride, and 1.0 g of chlorine gas gave 2.8 g of the product, yield: 78.2%.

[0097] (2) Synthesis of 4-(tridecafluorohexyltetrafluorosulfurmethylene)styrene

[0098] The synthesis of 4-(tridecafluorohexyltetrafluoromethylene)styrene refers to the synthesis steps of 4-(nonafluorobutyltetrafluoromethylene)styrene in Example 1. The reactants and dosage are intermediate 4 -(Tridecafluorohexyltetrafluorosulfurmethylene)chlorobenzene 1.3 g, Pd...

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Abstract

The invention discloses a perfluoroalkyl tetrafluoromethylene styrene copolymer and its application. Using perfluoroalkyltetrafluorosulfurmethylene styrene as a water-repellent functional monomer, the fluorine-containing fabric finishing agent is prepared by emulsion copolymerization. The product can provide excellent liquid repellency and durability when used in fabric finishing. The perfluoroalkyl tetrafluoromethylene halobenzene used in the synthesis of finishing agents is based on perfluoroalkyl thiohalobenzene as a precursor compound, which is fluorinated with a fluorinating reagent to generate an intermediate perfluoroalkyl tetrafluoromethylene halobenzene; The intermediate is then reacted with vinylmagnesium bromide to obtain perfluoroalkyltetrafluorosulfurmethylene styrene. In the preparation process of the present invention, the reaction conditions are mild and the process is simple; the raw materials are cheap and the cost is low; and it is easy to be popularized and applied industrially. In the structure of fluorine-containing functional monomers, sulfur tetrafluoromethylene is directly connected to the phenyl group as a linking group. Since the large π bond of the benzene ring has a charge dispersion and stabilization effect on sulfur tetrafluoride, it provides good heat resistance for the fluorine-containing monomers. stability. At the same time, the sulfur-carbon bond is easy to degrade under ultraviolet light irradiation, and the obtained fluorine-containing finishing agent has good degradability, and is an environment-friendly fluorine-containing finishing auxiliary agent.

Description

technical field [0001] The invention relates to an easily degradable fluorine-containing finishing agent and a preparation method thereof, in particular to a perfluoroalkyltetrafluorosulfurmethylene styrene copolymer fabric finishing agent and a preparation method thereof, belonging to textile post-finishing auxiliary agents and containing The technical field of fluorine material preparation. Background technique [0002] Fluorine-containing acrylate polymers have the advantages of good film-forming properties, low surface free energy, good thermal stability and corrosion resistance, so they have been widely used in textiles, leather and other fields. During application, fluoropolymers impart specific wetting properties to the substrate by forming a film on the surface of the substrate, such as a fiber, to provide a protective layer with very low surface free energy. Many studies have shown that the excellent hydrophobic and oleophobic properties of fluoropolymers are deter...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F212/14C08F220/18C08F220/14C08F220/20D06M15/356D06M101/06
CPCC08F212/14D06M15/263D06M15/3566D06M2101/06D06M2200/12C08F220/18C08F220/14C08F220/20
Inventor 李战雄吴优陈蕾
Owner SUZHOU UNIV
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