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Organic silicon coupling agent containing beta-dicarbonyl and preparation method thereof

A silicone coupling agent, dicarbonyl technology, applied in the field of preparation of new high temperature resistant silicone coupling agent, the silicone coupling agent can solve the problems of low-grade processing, limited use range, long production process, etc. , to achieve the effect of unique performance, low cost and convenient operation

Inactive Publication Date: 2012-06-13
NORTHWEST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of these organosilane coupling agents are substituted by long-chain alkoxy groups, the activity is reduced, and it is not easy to bond with fillers
In addition, their production process is long, the pollution is serious, and the purity is low, and the yield is also low, so that the processing and results are at a low level, and the scope of use is limited to a certain extent.

Method used

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  • Organic silicon coupling agent containing beta-dicarbonyl and preparation method thereof
  • Organic silicon coupling agent containing beta-dicarbonyl and preparation method thereof
  • Organic silicon coupling agent containing beta-dicarbonyl and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Embodiment 1, the preparation of diethyl 2-(3-dimethoxy (methyl) silicon) propane) ethyl ester

[0043](1) Preparation of diethyl allylmalonate

[0044] Add anhydrous potassium carbonate (8.58g, 61mmol), diethyl malonate (7.68g, 60mmol), allyl chloride (4.64g, 65mmol) into a 150 mL round-bottomed flask in turn, and then add polar organic Solvent acetonitrile 70mL, control the temperature at 80°C, reflux and stir for 24 hours, take it out and cool to room temperature, add water to remove excess potassium carbonate, extract with ethyl acetate, wash the organic phase with water 3 times, dry over anhydrous sodium sulfate, and vacuum rotary evaporation The solvent was spin-dried to obtain a yellow transparent liquid as the product (directly used in the next reaction without further purification), with a yield of 95%.

[0045] The resulting product allyl malonate diethyl ester structure is:

[0046]

[0047] The NMR data are as follows:

[0048] 1 H NMR (400 MHz, CDCl...

Embodiment 2

[0056] The preparation of embodiment 2,2-(3-dimethoxy (methyl) silicon) propane) acetylacetone

[0057] (1) Preparation of allyl acetylacetone

[0058] Add anhydrous potassium carbonate (8.58g, 61mmol), acetylacetone (6g, 60mmol), allyl chloride (4.64g, 65mmol) into a 150 mL round bottom flask in turn, and then add 70 mL of acetonitrile, a polar organic solvent, into the flask In the medium, control the temperature at 80°C, reflux and stir for 24 hours, take it out and cool to room temperature, add water to remove excess potassium carbonate, extract with ethyl acetate, wash the organic phase with water 3 times, dry over anhydrous sodium sulfate, and vacuum rotary evaporator The solvent was spin-dried to obtain a yellow transparent liquid which is the product allyl acetylacetone (directly used in the next step reaction without further purification), with a yield of 92%. Its structure is:

[0059]

[0060] The NMR data are as follows:

[0061] 1 H NMR (400 MHz, CDCl 3 ): ...

Embodiment 4

[0076] Embodiment 4, the preparation of diethyl 2-(3-dichloro(methyl)silyl)propane) ethyl ester

[0077] (1) Preparation of diethyl allylmalonate: same as Example 1.

[0078] (2) Preparation of diethyl 2-(3-dichloro(methyl)silyl)propane)ethyl ester

[0079] In a 50 mL round bottom flask, the platinum metal catalyst platinum-vinylsilane complex Pt 2 (Me 2 (CH=CH 2 ) 2 Si 2 O) 3 (4.74mg) was diluted in 30mL of desulfurized toluene, then 50mmol of dichloromethylsilane and 10mmol of allyl diethylmalonate were mixed and added dropwise to the flask, the temperature was controlled at 40°C, and stirred for 3~ After 6 hours, distill and collect fractions to obtain the product diethyl 2-(3-dichloro(methyl)silyl)propane)ethyl ester. Yield 56%. Its structure is:

[0080]

[0081] The NMR data are as follows:

[0082] 1 H NMR (400 MHz, CDCl 3): d = 4.12-4.11 (m, 4H), 3.15-3.13 (m, 1H), 2.03-2.02 (m, 2H), 1.38-1.36 (m, 2H), 1.35-1.34 (m, 2H), 1.30 -1.28 (m, 6H), 0.79-0.7...

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Abstract

The invention provides an organic silicon coupling agent containing beta-dicarbonyl, which belongs to the field of organic chemical synthesis. As the organic coupling agent has a beta-dicarbonyl functional group, the dicarbonyl in the structure has a coordination chelating function, is conductive to generation of coplanar acting force and increase of adhesive property, thereby further solving the application problem that fluorubber and fluorosilicone rubber are difficult to adhere; and the organic silicon coupling agent can be used for preparing special silicon oil and silicon resin. The preparation method of the organic silicon coupling agent comprises the following steps of reacting a compound containing the beta-dicarbonyl with allyl chloride under the catalysis of potassium carbonate to synthesize an allyl compound containing the beta-dicarbonyl, and then performing addition with siloxane under the catalysis of a platinum metal complex. The preparation method is simple in process and post-treatment, convenient to operate, high in yield, low in cost and easy for industrialization; and since the allylated beta-dicarbonyl compound is catalyzed by potassium carbonate, the traditional high-temperature reaction of allylic alcohol under catalysis of a high-toxicity precious metal is avoided, energy consumption is reduced, the operation is facilitated and the cost is reduced.

Description

technical field [0001] The invention relates to a novel high-temperature-resistant organosilicon coupling agent, in particular to an organosilicon coupling agent containing a β-dicarbonyl group, and also relates to a preparation method of the organosilicon coupling agent. Background technique [0002] Organosilane coupling agent is made of silicon chloroform (HSiCl 3 ) and unsaturated olefins with reactive groups were added under the catalysis of platinum chloride acid, followed by alcoholysis. It is essentially a class of silanes with organic functional groups, which have reactive groups that can chemically bond with inorganic materials (such as glass, silica sand, metals, etc.) and chemically bond with organic materials (synthetic resins, etc.) reactive group. The application of silane coupling agent can be roughly summarized into three aspects: [0003] (1) Surface treatment of glass fiber: it can improve the bonding performance of glass fiber and resin, and greatly im...

Claims

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Application Information

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IPC IPC(8): C07F7/18C07F7/16
Inventor 高非卢科蓉魏博侯学清雷自强康旭
Owner NORTHWEST NORMAL UNIVERSITY
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