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Silicon-containing benzocyclobutene monomers and preparation method thereof

A technology of bromobenzocyclobutene and dimethylbenzocyclobutene is applied in the field of silicon-containing benzocyclobutene monomer and its preparation, and can solve problems such as poor film-forming performance, and achieve faster reaction speed, The effect of reducing side reactions and excellent overall performance

Inactive Publication Date: 2011-10-05
SOUTHWEAT UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Common silicone polymers have excellent properties such as high and low temperature resistance, weather resistance, electrical insulation, radiation resistance, flame retardancy, good air tightness, and corrosion resistance, and are widely used in many important fields such as aerospace, but general Silicone materials have poor film-forming properties, and polymer materials with better film-forming properties need to be modified by specific functional groups

Method used

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  • Silicon-containing benzocyclobutene monomers and preparation method thereof
  • Silicon-containing benzocyclobutene monomers and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0033] The preparation method of 1-dimethylvinylsilyl benzocyclobutene:

[0034] Vacuumize the vial containing the magnetic stirrer and fill it with nitrogen three times, then in nitrogen (N 2 ) under the protection of magnesium (Mg) (264mg, 11mmol), anhydrous lithium chloride (LiCl) (467.5mg, 11mmol), lithium aluminum hydride (LiAlH 4 ) (76mg, 2mmol) was added to the vial and stirred by magnetic force for a period of time. A solution of 1-BrBCB (1-bromobenzocyclobutene) (1.3 mL, 11 mmol) in tetrahydrofuran (26 mL) was added under nitrogen. Stir rapidly at room temperature for 2 hours. After the magnesium strips are almost completely reacted, add a solution of dimethylvinylchlorosilane (1.4 mL, 10 mmol) in tetrahydrofuran (5 mL) dropwise, and stir rapidly at room temperature for 1 hour. Add a certain amount of water to stop the reaction, extract with ether, combine the organic phases, and use anhydrous MgSO 4 Dry it, let it stand overnight, filter it with suction, and separ...

Embodiment 2

[0036] The preparation method of 1-dimethylvinylsilyl benzocyclobutene:

[0037] Vacuumize the vial containing the magnetic stirrer and fill it with nitrogen three times, then in nitrogen (N 2 ) under the protection of magnesium strips (2.64g, 110mmol), anhydrous lithium chloride (LiCl) (467.5mg, 110mmol) and lithium aluminum hydride (LiAlH 4 ) (760mg, 20mmol) was added to the vial, and magnetically stirred for a period of time. A solution of 1-BrBCB (1-bromobenzocyclobutene) (13 mL, 110 mmol) in tetrahydrofuran (260 mL) was added under nitrogen. Stir rapidly at 30°C for 5 hours, after the magnesium strips are almost completely reacted, add dropwise a solution of dimethylvinylchlorosilane (14mL, 100mmol) in tetrahydrofuran (50mL), and stir rapidly at 30°C for 3 hours. Add a certain amount of water to stop the reaction, extract with ether, combine the organic phases, and use anhydrous MgSO 4 Dry it, let it stand overnight, filter it with suction, and separate and purify it b...

Embodiment 3

[0039] The preparation method of 1-dimethylvinylsilyl benzocyclobutene:

[0040] Vacuumize the vial containing the magnetic stirrer and fill it with nitrogen three times, then in nitrogen (N 2 ) under the protection of magnesium strips (26.4mg, 1.1mmol), anhydrous lithium chloride (LiCl) (46.7mg, 0.126 mmol) and lithium aluminum hydride (LiAlH 4 ) (7.6mg, 0.2mmol) was added to the vial and stirred by magnetic force for a period of time. A solution of 1-BrBCB (1-bromobenzocyclobutene) (0.13 mL, 1.1 mmol) in tetrahydrofuran (0.4 mL) was added under nitrogen. Stir rapidly at room temperature for 2 hours. After the magnesium strips are almost completely reacted, add a solution of dimethylvinylchlorosilane (0.14 mL, 1 mmol) in tetrahydrofuran (1 mL) dropwise, and stir rapidly at room temperature for 1 hour. Add a certain amount of water to stop the reaction, extract with ether, combine the organic phases, and use anhydrous MgSO 4 Dry it, let it stand overnight, filter it with su...

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Abstract

The invention discloses silicon-containing benzocyclobutene monomers, such as dimethyl vinyl benzocyclobuten-1-ylsiloxane, and a preparation method thereof. The preparation method of the compound comprises: adding magnesium, anhydrous lithium chloride and lithium aluminum hydride into a reactor under water-free, anaerobic and nitrogen-protection conditions; dripping the tetrahydrofuran solution of 1-bromobenzocyclobutene with stirring, dripping the tetrahydrofuran solution of methylvinyldichlorosilane after the magnesium is reacted completely, and reacting at -20 to 40 DEG C for 3 to 24 hours; and adding water to terminate reaction, extracting with an organic solvent, drying an organic phase by using an organic salt drying agent, concentrating, and subjecting the concentrated material to reduced-pressure distillation or silica column chromatography to obtain a product. The compound contains reactive vinylsilyl and hydrosilyl reaction groups, and the high polymer material formed by reaction has high comprehensive performance and has great development potential and application prospect in fields of microelectronics, aerospace and national defense.

Description

technical field [0001] The invention belongs to a silicon-containing carbocyclic compound and a preparation method thereof, and relates to a silicon-containing benzocyclobutene monomer (dimethylvinylbenzocyclobutene-1-ylsilane or dimethylbenzocyclobutene Cyclobuten-4-ylhydrosilane) and its preparation method. The prepared silicon-containing benzocyclobutene monomer is suitable for fields such as microelectronics industry, aerospace and national defense. Background technique [0002] Benzocyclobutene (BCB) materials have been widely used abroad due to their excellent high and low temperature resistance, weather resistance, good air tightness, radiation resistance, especially excellent film-forming properties and moisture resistance. To the military and civilian fields. Common silicone polymers have excellent properties such as high and low temperature resistance, weather resistance, electrical insulation, radiation resistance, flame retardancy, good air tightness, and corro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/08
Inventor 杨军校黄亚文张成元张林李波朱方华
Owner SOUTHWEAT UNIV OF SCI & TECH
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