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Propylene acyloxy methacryloxy silane and preparation method of its derivative

A technology of acryloyloxymethacryloyloxysilane and methacrylic acid, which is applied in the field of synthesis of organosilicon compounds, can solve the problems of expensive catalyst reaction conditions, low catalytic efficiency, and easy polymerization of double bonds, and achieve easy industrialization The effect of high production, high yield and simple post-processing

Inactive Publication Date: 2015-09-09
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The hydrosilylation method is mainly the addition of organosilicon compounds containing silicon-hydrogen bonds and diene carboxylate under the condition of a platinum compound catalyst. This method has expensive catalysts, strict reaction conditions, and complicated operations.
The nucleophilic substitution method is mainly a substitution reaction between unsaturated carboxylate and haloalkylsilane under the condition of a phase transfer catalyst. This method generally requires strict reaction conditions, low catalytic efficiency, and the double bond is easy to polymerize during the reaction process.
[0004] The above methods can only synthesize silanes containing one unsaturated acryloyloxy group, and there is currently no silane with simple operation, high reaction efficiency, and low cost that can simultaneously synthesize two silanes with unsaturated acryloyloxyalkyl groups and acryloyloxy groups. Unsaturated acyloxy silane method

Method used

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  • Propylene acyloxy methacryloxy silane and preparation method of its derivative
  • Propylene acyloxy methacryloxy silane and preparation method of its derivative
  • Propylene acyloxy methacryloxy silane and preparation method of its derivative

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Effect test

Embodiment 1

[0038] Embodiment 1, the preparation of acryloyloxymethacryloyloxydimethylsilane

[0039] The structural formula of acryloxymethacryloxydimethylsilane is as formula (IV):

[0040]

[0041] Including the following steps:

[0042] Put 14.79g of acrylic acid, 0.24g of p-tert-butyl catechol, 0.37g of tetrabutyl chlorinated Ammonium and 50.02g of anhydrous xylene, slowly add 14.17g of chloromethyl dimethyl chlorosilane dropwise into the reaction flask, the rate of dropping is 2ml / min, stir slowly, after the dropwise addition is completed, keep the reaction at 90°C After 8 hours, after the completion of the reaction, cool to room temperature naturally, filter under reduced pressure, remove toluene from the filtrate, and distill under reduced pressure at a pressure of 2 to 3 mmHg to obtain a colorless and transparent liquid product with a yield of 79.86%.

[0043] The infrared of the product obtained in this embodiment, the proton nuclear magnetic spectrum and the carbon spectru...

Embodiment 2

[0044] Embodiment 2, the preparation of acryloyloxymethacryloyloxydimethylsilane

[0045] The structural formula of acryloyloxymethacryloyloxydimethylsilane is as formula (IV),

[0046] Including the following steps:

[0047] Put 18.81g of sodium acrylate, 0.20g of p-tert-butylcatechol, 0.58g of tetrabutyl bromide into a four-necked round-bottomed flask equipped with a spherical condenser, a thermometer, a constant pressure dropping funnel, and a T-shaped three-way piston. Add phosphine and 50.28g of anhydrous toluene, and slowly add 14.21g of chloromethyl dimethyl chlorosilane into the reaction flask dropwise, the rate of addition is 2ml / min, stir slowly, after the addition is completed, keep the temperature at 85°C for reaction After 8 hours, after the completion of the reaction, cool to room temperature naturally, filter under reduced pressure, remove toluene from the filtrate, and distill under reduced pressure at a pressure of 2 to 3 mmHg to obtain a colorless and transp...

Embodiment 3

[0048] Embodiment 3, the preparation of acryloyloxymethacryloyloxymethylethylsilane

[0049] The structural formula of acryloyloxymethacryloyloxymethylethylsilane is as formula (Ⅴ):

[0050]

[0051] Including the following steps:

[0052] Put 22.03g of potassium acrylate, 0.36g of 4-4-methylenebis(2,6- Di-tert-butylphenol), 0.71g tetrabutylphosphine bromide and 52.36g anhydrous toluene, 15.70g chloromethylmethyl ethyl chlorosilane is slowly added dropwise in the reaction flask, and the rate of addition is 1.5ml / min, stir slowly, after the dropwise addition is completed, keep the temperature at 100°C for 12 hours, after the reaction is completed, naturally cool to room temperature, filter under reduced pressure, remove toluene from the filtrate, distill under reduced pressure, the pressure is 2 ~ 3mmHg, and the colorless and transparent Liquid product, yield 78.17%.

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Abstract

The invention relates to propylene acyloxy methacryloxy silane and a preparation method of its derivative. The method comprises the following steps: 1)adding acrylic acid or acrylate or methacrylic acid or methacrylate, a polymerization inhibitor and a phase-transfer catalyst in an organic solvent, uniformly mixing to obtain a mixing material; 2)dropping chloromethyl chlorosilane in the mixing material, under inert gas protection, stirring and reacting for 8-15 hours at temperature of 70-100 DEG C; and 3)after reaction is complete, naturally cooling to room temperature, performing pressure reduction and filtering, removing an organic solvent of a filtrate, performing underpressure distillation to obtain the product; wherein the product is the colorless transparent liquid. The method has the advantage of easily available raw materials, no harsh reaction condition, simple operation, and simple post-treatment; usage of a platinum catalyst with high cost as a raw material can be avoided, double bond polymerization can be effectively controlled by the reaction, side reaction is less, and industrial production is easy.

Description

technical field [0001] The invention relates to a preparation method of acryloyloxymethacryloyloxysilane and derivatives thereof, and belongs to the technical field of synthesis of organosilicon compounds. Background technique [0002] Organosilicon compounds with unsaturated carbon-carbon double bonds and ester bonds (acyloxy bonds) are an important class of monomers. Acryloyloxymethacryloyloxysilane and its derivatives have a wider range of uses. As a reactant, many functional organosilicon compounds and polymers can be synthesized. The unsaturated double bond endows this type of silane with high reactivity, so that this type of silane can be widely used as a crosslinking agent in the fields of silicone resin, silicone rubber, and silicone coatings. The acyloxy bond makes this kind of silane have higher polarity, and the active reactivity of silicon-acyloxy bond makes this kind of silane have a more efficient and convenient application in organosilicon modification. In a...

Claims

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Application Information

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IPC IPC(8): C07F7/18
Inventor 张洁张玉晗冯圣玉
Owner SHANDONG UNIV
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