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Benzocyclobutene functional groups-contained benzoxazine monomer and synthetic method and use thereof

A technology of benzocyclobutene and benzoxazine, which is applied in the field of benzoxazine monomer and its synthesis, can solve the problems of insufficient thermal stability and high curing temperature, and achieve excellent thermal stability and low hygroscopicity Effect

Inactive Publication Date: 2012-03-28
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Benzoxazine has the disadvantages of brittleness, high curing temperature and insufficient thermal stability, so it is necessary to modify it or design a multifunctional benzoxazine through molecular engineering

Method used

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  • Benzocyclobutene functional groups-contained benzoxazine monomer and synthetic method and use thereof
  • Benzocyclobutene functional groups-contained benzoxazine monomer and synthetic method and use thereof
  • Benzocyclobutene functional groups-contained benzoxazine monomer and synthetic method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1 Synthesis of 3-(4'-benzocyclobutenyl)-3,4-dihydro-[1,3]benzoxazine (molecular formula 1)

[0030]

[0031] Formula 1

[0032] Under the condition of ice bath (temperature below 10 degrees), add 1.623g 37% formaldehyde solution, adjust pH=9 with sodium hydroxide solution, then add 1.19g 4-aminobenzocyclobutene and 20ml dioxane, After reacting at room temperature for 1 hour, add 0.941 g of phenol, heat to 50-85 degrees Celsius, and react at constant temperature for 2-24 hours. After removing dioxane by rotary evaporation under reduced pressure, the reaction solution was dissolved in dichloromethane, washed with sodium hydroxide solution and deionized water until neutral, and separated. The dichloromethane was removed by rotary evaporation, and 2.01 g of the target product (molecular formula 1) was obtained with a yield of 85%. 1 H-NMR (500 MHz, CDCl 3 , δ): 3.07 (s, 4H), 4.57 (s, 2H), 5.30 (s, 2H), 6.78-7.10 (m, 7H).

Embodiment 2

[0033] Example 2 Synthesis of 3-(4'-benzocyclobutenyl)-3,4-dihydro-[1,3]benzoxazine (molecular formula 1)

[0034] In the single-necked bottle, add 1.19g of 4-aminobenzocyclobutene, 0.94g of phenol, and 0.60g of paraformaldehyde, toluene, and heat at 110 degrees to reflux the toluene. After 5 hours the reaction was complete. The toluene was removed by rotary evaporation, and then the crude product was dissolved in dichloromethane, washed with sodium hydroxide solution until the upper aqueous solution was colorless, and then washed with deionized water until neutral. The dichloromethane was removed by rotary evaporation to obtain 1.90 g of the target product with a yield of 80%.

Embodiment 3

[0035] Example 3 Synthesis of 3-(4'-benzocyclobutenyl)-8-allyl-3,4-dihydro-[1,3]benzoxazine (molecular formula 2)

[0036]

[0037] Formula 2

[0038] In a single-necked bottle, add 1.1916g 4-aminobenzocyclobutene, 1.3418g 2-allylphenol, and 0.60g paraformaldehyde, 20mL toluene, and heat at 110 degrees to reflux the toluene. After 5 hours the reaction was complete. The toluene was removed by rotary evaporation, and then the crude product was dissolved in dichloromethane, washed three times with sodium hydroxide solution until the upper aqueous solution was colorless, and then washed with deionized water until neutral. The dichloromethane was removed by rotary evaporation to obtain 2.22 g of the target product with a yield of 80%. 1 H-NMR (500 MHz, CDCl 3 ,δ): 3.07 (s, 4H), 3.33 (d, 2H), 4.55 (s, 2H), 5.03 (m, 2H), 5.30 (s, 2H), 5.97 (m, 1H), 6.79-6.96 ( m, 6H).

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Abstract

The invention belongs to the technical field of macromolecular materials and particularly relates to a benzocyclobutene functional groups-contained benzoxazine monomer and a synthetic method and a use thereof. According to the synthetic method, amino-contained benzocyclobutene, phenolic compounds and formaldehydes (or paraformaldehydes) are adopted as raw materials, and the target monomer is obtained through synthesizing by adopting a solvent method or a solvent-free method. The benzoxazine monomer has lower viscosity at a certain temperature and can be cured through a method of heating or catalyzing by a catalyst. The obtained resin after curing has excellent thermal stability, mechanical properties, and extremely-low hygroscopicity, and thus, the resin can be used as an electronic packaging material, a high-temperature resisting and flame-retarding material, a high-performance composite material, an aerospace material and the like.

Description

technical field [0001] The invention belongs to the technical field of polymer materials, and in particular relates to a benzoxazine monomer containing a benzocyclobutene functional group and a synthesis method and application thereof. Background technique [0002] High-performance polymer materials, especially those with high heat resistance, low water absorption, and low dielectric constant, can be used as interlayer dielectrics (isolation layers), passivation layers, bottom filling materials, etc. in microelectronic packaging The industry has a wide range of applications, and can also be used to prepare high-performance composite materials for aerospace and other fields. [0003] Benzoxazine is a new type of resin monomer containing oxygen and nitrogen six-membered heterocyclic rings. It is prepared by dehydration condensation reaction of primary amine compounds, phenolic compounds and aldehyde compounds under certain conditions. It can undergo a ring-opening reaction un...

Claims

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Application Information

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IPC IPC(8): C07D265/16C08G73/00
Inventor 程元荣肖斐
Owner FUDAN UNIV
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