Perfluoroalkyl styrene and application thereof

A technology of perfluoroalkyl styrene and perfluoroalkyl thiohalobenzene is applied in the field of polymer monomers and easily degradable fluorine-containing chemicals, and can solve the problem that long-carbon chain perfluoroalkyl groups are not easy to degrade and accumulate in the environment. Toxicity and other issues, to achieve the effects of excellent liquid repellency, good thermal stability, and excellent liquid repellency

Active Publication Date: 2019-10-01
东莞市德伦新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Aiming at the problems existing in the current fluorine-containing finishing agent, the present invention discloses a new perfluoroalkyl styrene, which utilizes tetrafluorosulfurmethylene to extend the carbon chain perfluoroalkyl chain length, and the obtained perfluoroalkyl material can be Obtain better liquid repellency than carbon chain perfluoroalkyl materials; at the same time, the present invention solves the environmental accumulation toxicity problem caused by long carbon chain perfluoroalkyl that is not easy to degrade, and the carbon chain perfluorinated by tetrafluoromethylene The alkyl group is bridged with the benzene ring, using the large π bond of the benzene ring to -SF 4 The electronic stabilization effect of - endows the fluorine-containing alkyl group with good heat resistance stability, and at the same time, the perfluoroalkyl group with an extended chain is formed by tetrafluorosulfurmethylene and carbon chain perfluoroalkyl group, so as to improve the stability of fluoride materials Liquid repellent function

Method used

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  • Perfluoroalkyl styrene and application thereof
  • Perfluoroalkyl styrene and application thereof
  • Perfluoroalkyl styrene and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] In this example, 4-(nonafluorobutyltetrafluorosulfurmethylene)styrene is synthesized, and the specific steps are as follows:

[0066] (1) Synthesis of 4-(nonafluorobutylthio)bromobenzene by addition of fluoroalkyl radicals

[0067] 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 evaporated under red...

Embodiment 2

[0073] In this embodiment, 4-(tridecafluorohexyltetrafluorosulfurmethylene)styrene is synthesized, and the specific steps are as follows:

[0074] (1) Synthesis of 4-(tridecafluorohexylthio)bromobenzene by addition of fluoroalkyl radicals

[0075] The synthesis steps and feed ratio of 4-(tridecafluorohexylthio)bromobenzene refer to the synthesis steps of 4-(nonafluorobutylthio)bromobenzene in Example 1, and 13.4 g of perfluoroiodohexane is added when feeding, The same amount of other materials was used to obtain 8.5 g of the product 4-(tridecafluorohexylthio)bromobenzene, yield: 62.0%. image 3 and Figure 4 Respectively the 4-tridecafluorohexylthiobromobenzene prepared above 1 HNMR and 19 F NMR spectrum: 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 ...

Embodiment 3

[0081] In this example, 4-(nonafluorobutyltetrafluorosulfurmethylene)styrene is synthesized, and the specific steps are as follows:

[0082] (1) Synthesis of 4-(nonafluorobutylthio)chlorobenzene by addition of fluoroalkyl radicals

[0083] In a 250 ml three-necked flask equipped with a magnetic stirrer, a thermometer, a constant pressure dropping funnel, and a reflux condenser, add 4.7 g of p-chlorothiophenol, 10.5 g of nonafluoro-1-iodobutane, 0.5 g of copper acetate and 45 g of 1,4-dioxane, stirred and heated to 72°C, the reaction solution turned yellow. Dissolve 7.3 g of benzoyl peroxide in 50 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 evaporated under...

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Abstract

The invention discloses a perfluoroalkyl styrene monomer and application thereof. The perfluoroalkyl styrene monomer is prepared by the following steps of using monohalogenated thiophenol and perfluoro-iodoalkane as the raw materials, so as to obtain an intermediate, namely perfluoroalkyl thiohalobenzene; further fluorinating, so as to obtain perfluoroalkyl tetrafluorothio methylene halobenzene; finally, reacting with vinyl magnesium bromide, so as to obtain perfluoroalkyl tetrafluorothio methylene styrene. The prepared tetrafluorothio methylene-containing perfluoroalkyl styrene has the advantages that the reaction property is realized, and the tetrafluorothio methylene-containing perfluoroalkyl styrene can be used for preparing fluorine-containing surface treatment materials and liquid-repelling surfaces; because the perfluoroalkyl is bonded with rigid benzene rings, the whole structure of the fluorine-compound has larger crystallizing property, and the excellent liquid-repelling property is obtained; the tetrafluorothio methylene is used as a bridge group, and is directly bonded with the benzene ring, and the good heat-resistant stability is provided by the electron stable reaction of large phi bond of the benzene ring corresponding to the sulfur tetrafluoride; the tetrafluorothio methylene-containing perfluoroalkyl styrene is easy to degrade under the radiation by ultraviolet light, and the obtained fluorine-containing material is environment-friendly.

Description

technical field [0001] The invention relates to a fluorine-containing styrene monomer and a preparation method thereof, in particular to a tetrafluorosulfurmethylene-containing perfluoroalkylstyrene and its application, and belongs to the preparation technology of polymer monomers and easily degradable fluorine-containing chemicals field. Background technique [0002] Among fluorine-containing materials, phenyl-substituted sulfur pentafluoride is C 2v Axisymmetric, the S-F bond where one fluorine atom is located is perpendicular to the plane formed by the other four fluorine atoms and sulfur atoms, and the plane where the benzene ring is located is distributed in the place where the steric hindrance of the four fluorine atoms is the least, and the four equatorial S-F bonds offset its local dipole moment, the dipole moment of the whole group is mainly contributed by the fluorine substituent (-F) perpendicular to this plane, if the axial fluorine substituent is replaced by th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C381/00C08F112/14C09D125/18
CPCC07C381/00C08F112/14C09D125/18
Inventor 李战雄王雪婷陈蕾
Owner 东莞市德伦新材料有限公司
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