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Fluorine-containing organosilicone monomer and preparation method thereof

A technology of organosilicon and monomers, which is applied in the direction of organic chemistry, chemical instruments and methods, compounds of group 4/14 elements of the periodic table, etc., can solve the problem that short fluoroalkyl groups do not have crystallinity and cannot be arranged in liquid crystal structure, short fluorine Problems such as application limitation of alkylation materials, reduction of water and oil repellency performance, etc., to achieve the effect of environmentally friendly surface activity, high fluorine content, and low surface tension

Active Publication Date: 2015-08-12
JIANGSU HUAJIA SILK
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

When analyzing the surface tension of fluoroalkyl polymers, it was found that as the length of the carbon chain of the perfluoroalkyl side group decreases, the surface tension of the polymer gradually increases, and the water and oil repellency decreases. This is because the number of carbon chain atoms The perfluoroalkyl chain of ≤6 has the following two disadvantages: (1) the short fluoroalkyl group does not have crystallinity, cannot form a stable liquid crystal structure arrangement, and it is difficult to make -CF 3 High density and stable arrangement on the outermost surface; (2) The fluorine content of polymers synthesized from short fluoroalkyl monomers is often low, and it is difficult to achieve the effect of fluorine atoms completely shielding the polymer main chain and polymer film
Because of this, the application of short fluoroalkylated materials is limited

Method used

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  • Fluorine-containing organosilicone monomer and preparation method thereof
  • Fluorine-containing organosilicone monomer and preparation method thereof
  • Fluorine-containing organosilicone monomer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] In a four-necked flask equipped with a reflux condenser, mechanical stirring and heating device, put 400 grams of 3-tridecafluorohexylpropene and 500 grams of tridecafluoro-1-iodohexane, and heat the mixture to 88 ° C, under nitrogen protection Add 10 grams of initiator azobisisobutyronitrile, and stir the reaction mixture at 88°C for 48 hours. During this period, add azobisisobutyronitrile three times every 12 hours, and add 2 grams of azobisisobutyronitrile each time. Nitrile. After the reaction is over, stop the reaction, and rectify (the temperature is 150°C, the vacuum degree is 2mmHg) to obtain a fraction at 106-107°C, which is the product 1,3-bis(tridecafluorohexyl)-2-iodopropane, with a yield of 97.0 %.

[0036]In a three-necked flask equipped with a reflux condenser, a thermometer, and a constant pressure dropping funnel, add 2.9 grams of magnesium chips and 50 grams of anhydrous tetrahydrofuran, introduce nitrogen, start stirring with a magnetic stirrer, and ...

Embodiment 2

[0048] 1,3-bis(tridecafluorohexyl)-2-iodopropane was prepared according to Example 1.

[0049] In a three-necked flask equipped with a reflux condenser, a thermometer and a constant pressure dropping funnel, add 3.1 grams of magnesium chips and 55 grams of anhydrous ether, introduce nitrogen, start stirring with a magnetic stirrer, and heat the system to 30 ° C with a water bath, 69.2 g of 1,3-bis(tridecafluorohexyl)-2-iodopropane was added dropwise through a constant pressure dropping funnel for a total of 1 hour and 15 minutes. After the addition, the reaction was continued for 6 hours to obtain a suspension of 1,3-bis(tridecafluorohexyl)-2-propylmagnesium iodide.

[0050] The above 1,3-bis(tridecafluorohexyl)-2-propylmagnesium iodide suspension was cooled to -3°C and set aside.

[0051] In a three-necked flask equipped with a reflux condenser, a thermometer and a constant pressure dropping funnel, add 12.9 grams of tetrachlorosilane and 55 grams of anhydrous ether, introdu...

Embodiment 3

[0060] 1,3-bis(tridecafluorohexyl)-2-iodopropane was prepared according to Example 1.

[0061] In a three-necked flask equipped with a reflux condenser, a thermometer and a constant pressure dropping funnel, add 3.5 grams of magnesium chips and 60 grams of anhydrous ether, introduce nitrogen, start stirring with a magnetic stirrer, and heat the system to 30 ° C with a water bath, 69.5 g of 1,3-bis(tridecafluorohexyl)-2-iodopropane was added dropwise through a constant-pressure dropping funnel for a total of 1 hour. After the addition, the reaction was continued for 6 hours to obtain a suspension of 1,3-bis(tridecafluorohexyl)-2-propylmagnesium iodide.

[0062] The above 1,3-bis(tridecafluorohexyl)-2-propylmagnesium iodide suspension was cooled to -5°C and set aside.

[0063] In a three-necked flask equipped with a reflux condenser, a thermometer and a constant pressure dropping funnel, add 7.2 grams of tetrachlorosilane and 48 grams of anhydrous ether, introduce nitrogen, and...

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Abstract

The invention discloses a fluorine-containing organosilicone monomer and a preparation method thereof. The method is characterized in that the method comprises the steps that 3-tridecafluorohexyl propylene and tridecafluoro-1-iodohexane are taken as starting materials, and undergo a single electron transfer addition reaction to synthesize 1,3-bi-(tridecafluorohexyl)-2-iodopropane; 1,3-bi-(tridecafluorohexyl)-2-iodopropane reacts with magnesium metal to prepare 1,3-bi-(tridecafluorohexyl)-2-propyl magnesium iodide which further reacts with silicon tetrachloride to form fluorine-containing alkyl-substituted chlorosilane; and a bi-[1,3-bi-(tridecafluorohexyl) isopropyl] dichloro-silicohydride product is obtained by recification. In a molecular structure of the product, perfluoroalkyl is short-chain perfluoroalkyl; the length of a carbon chain is equal to 6; the product is not degraded difficultly, has no cumulative toxicity, and is an environment-friendly monomer for synthesizing fluorine-containing polysiloxane. The preparation and reaction conditions of the fluorine-containing organosilicone monomer are mild; a technique is simple and convenient; the raw materials are easy to obtain; and industrialized production, and popularization and application are facilitated.

Description

technical field [0001] The invention relates to the preparation of organic compounds, in particular to a fluorine-containing organosilicon monomer and a preparation method thereof, belonging to the field of fluorine materials and fine chemicals. Background technique [0002] Fluorine atoms have small radius, high electronegativity, and low C-F bond polarizability, so the cohesion between polymer molecules containing carbon-fluorine bonds is small, and the surface energy of the polymer is very low, which endows its surface with water, oil, etc. Liquids are difficult to wet and adhere. The surface tension of the existing hydrophobic and oil-resistant polymers containing carbon-fluorine bonds is generally 20mN / m. It is generally considered that liquids with surface tensions lower than 20mN / m are high-surface active liquids. At present, the most widely used fluoropolymers are fluorine-containing polyacrylate and fluorine-containing polysiloxane. Most of these two fluoropolymers ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/14C08G77/24
Inventor 傅筠
Owner JIANGSU HUAJIA SILK
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