Silicon-containing diphenol and preparation method thereof

A technology of dihydric phenol and silane, which is applied in the field of silicon-containing dihydric phenol as a monomer of organosilicon materials and its preparation, can solve and/or solve the problems of cumbersome synthesis methods, difficulty in large-scale production, and poor performance, and achieve the goal of preparing Derivatives are convenient, high in industrial production value, and low in cost

Inactive Publication Date: 2015-08-05
QUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Therefore, the existing silicon-containing dihydric phenols have poor performance, and / or the synthesis method is cumbersome, harsh conditions, high cost, serious waste, etc., and it is difficult to achieve large-scale production

Method used

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  • Silicon-containing diphenol and preparation method thereof
  • Silicon-containing diphenol and preparation method thereof
  • Silicon-containing diphenol and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] The synthesis of embodiment 1 methylphenyl bis (4-hydroxy styryl) silane

[0033] Under the protection of nitrogen, the 80mL methylene chloride solution of 17.4g (0.10mol) of methylphenyldivinylsilane and 30.0g (0.25mol) of 4-vinylphenol was heated to 40°C for 15min, and 3.2g of ruthenium catalyst Cat- 1. Continue the heat preservation reaction for 8 hours, evaporate the solvent, and recrystallize the residue with ethyl acetate to obtain 33.1 g of off-white solid product methylphenylbis(4-hydroxystyryl)silane, with a yield of 92.5% and a content of 97.7% . MS (m / z): 359 [M+H] + .

Embodiment 2

[0034] Example 2 Synthesis of dimethylbis (3-hydroxyl-4-methoxystyryl) silane

[0035] Under nitrogen protection, heat a solution of 11.2g (0.10mol) of dimethyldivinylsilane and 34.5g (0.23mol) of 2-methoxy-5-vinylphenol in 80mL of dichloromethane to 30°C for 10min, and add 2.8 g ruthenium catalyst Cat-2, stirred at room temperature for 12 hours, evaporated the solvent, and recrystallized the residue from butyl acetate to obtain off-white solid product dimethylbis(3-hydroxy-4-methoxystyryl)silane 32.7 g, yield 91.8%, content 98.2%. MS (m / z): 357 [M+H] + .

Embodiment 3

[0036] Example 3 Synthesis of diphenylbis(3-methyl-4-hydroxystyryl)silane

[0037] Under nitrogen protection, heat a solution of 23.6g (0.10mol) of diphenyldivinylsilane and 34.8g (0.26mol) of 2-methyl-4-vinylphenol in 80mL of dichloromethane to 40°C for 10min, and add 2.5g Ruthenium catalyst Cat-3, continued insulation reaction for 14h, evaporated the solvent, and the residue was recrystallized with ethyl lactate to obtain 42.0 g of off-white solid product diphenylbis(3-methyl-4-hydroxystyryl)silane, Yield 93.7%, content 98.4%. MS (m / z): 449 [M+H] + .

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Abstract

The invention provides a silicon-containing diphenol and a preparation method thereof, wherein a structure of the silicon-containing diphenol is represented as the formula (I). The preparation method includes following steps: (A) with di-substituted divinyl silane as a raw material, performing a catalytic olefin double-decomposition reaction with vinylphenol to obtain an intermediate, di-substituted bis(hydroxylstyryl)silane; (B) performing catalytic hydrogenation and catalytic transfer hydrogenation to obtain di-substituted bis(hydroxylphenethyl)silane, which is the silicon-containing diphenol in the invention. The silicon-containing diphenol represented in the formula (I) is excellent in toughness, flame resistance and heat resistance. The preparation method is simple in operation, is mild in conditions, is high in product yield, is low in cost, is green and environment-friendly, and is high in industrialization value.

Description

technical field [0001] The invention relates to a silicon-containing dihydric phenol as an organosilicon material monomer and a preparation method thereof. Background technique [0002] Due to the excellent heat resistance, flexibility and flame retardancy of silicon-containing materials, silicon-containing monomers such as silicon-containing dihydric phenols, dibasic acids, and diamines can be used in polyamides, polyimides, and polyesters. The introduction of silicon into materials such as polycarbonate and epoxy resin to obtain chemically modified new polymer materials has always been an important development direction of the organic silicon industry and the polymer material industry. [0003] Dihydric phenols such as hydroquinone, 4,4’-diphenol, bisphenol A, bisphenol F, etc., are widely used in the preparation of aromatic polyesters, polycarbonates, epoxy resins and other materials. However, most of these dihydric phenols have defects such as insufficient toughness and...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/08C08G59/30
Inventor 郑土才许青青潘向军
Owner QUZHOU UNIV
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