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Benzo oxaxine intermediate containing aldehyde group and its preparation method

An intermediate, aldehyde benzene technology, applied in the field of thermosetting resin and its preparation, can solve the problems of high price and difficult polymer preparation process

Inactive Publication Date: 2009-10-14
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But because raw materials such as m-aminophenylacetylene and p-aminobenzonitrile are expensive, and the exothermic peak of the ring-opening curing reaction of the oxazine ring and the addition reaction exothermic peak of the ethynyl group in the ethynyl benzoxazine intermediate The temperature range of 200-250°C overlaps, so that a large amount of exothermic heat during curing is concentrated in a smaller temperature range, which makes it difficult for the preparation process of the polymer

Method used

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  • Benzo oxaxine intermediate containing aldehyde group and its preparation method
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  • Benzo oxaxine intermediate containing aldehyde group and its preparation method

Examples

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Effect test

Embodiment 1

[0034] Example 1 Synthesis of 3-phenyl-6-formyl-3,4-dihydro-2H-1,3-benzoxazine (AS-BOZ)

[0035] Under ice bath conditions (below 10°C), add 93.5 grams of formaldehyde solution and 30 grams of toluene to the three-necked flask, adjust the pH to 9 with sodium hydroxide solution, and add 53.4 grams of aniline dissolved in 30 grams of toluene. After stirring at low temperature for 30 minutes, 70 grams of p-hydroxybenzaldehyde was added, heated to rapidly raise the temperature of the reaction system to 80° C., and reacted at constant temperature for 5 hours. Wash with sodium hydroxide solution and water until the pH of the final washing aqueous phase is 7. The solvent toluene was removed by a vacuum rotary evaporator, and then recrystallized in toluene to finally obtain 3-phenyl-6-aldehyde-3,4-dihydro-1,3-benzoxazine as yellow needle crystals. Yield 90%; Infrared spectrum: oxazine ring (943cm -1 ), aldehyde group (1681cm -1 ); gelation time: t gel160℃ = 27 minutes and 27 secon...

Embodiment 2

[0036] Example 2 Synthesis of (3-phenyl-6-formyl-3,4-dihydro-2H-1,3-benzoxazine)methane (AB-BOZ)

[0037] At room temperature (lower than 20°C), add 64.8 grams of 35-40% formaldehyde solution into a three-necked bottle with a stirrer and a condenser, adjust the pH to 9 with sodium hydroxide solution, add 100 grams of toluene, ethanol 40 grams, 39.6 grams of diphenylmethanediamine, stirred for 15 minutes, then added 48.8 grams of p-hydroxybenzaldehyde, rapidly increased the temperature to 80 ° C, and stopped the reaction after 5 hours of reaction to obtain a golden yellow oil phase in the lower layer and a transparent water phase in the upper layer The phase separation system was washed with sodium hydroxide solution and water, and then the toluene was removed with a rotary evaporator to obtain a golden yellow liquid, namely bis(3-phenyl-6-aldehyde-3,4-dihydro-2H-1, 3-Benzoxazine) methane. Yield 80%, gelation time t gel160℃ = 31 minutes and 58 seconds.

Embodiment 3

[0038] Example 3 Bis(3-phenyl-6-formyl-3,4-dihydro-2H-1,3-benzoxazine)methane and bis(3-phenyl-3,4-dihydro-2H -1,3-benzoxazine) methane mixture synthesis

[0039]At room temperature (lower than 20°C), add 110 grams of 35-40% formaldehyde solution into a three-necked flask with a stirrer and a condenser, adjust the pH to 9 with sodium hydroxide solution, add 31.8 grams of phenol with stirring, and heat up to 40°C, quickly add 65 grams of diphenylmethanediamine, 105 grams of dioxane, and 35.6 grams of ethanol, the temperature of the system will automatically rise to 60°C, and continue stirring for 30 minutes. 40 grams of formaldehyde, heated up to 80 ° C, stopped the reaction after 5 hours at a constant temperature, cooled to obtain a golden yellow oil phase in the lower layer and a transparent water phase in the upper layer, washed with clear water, and then removed the solvent with a rotary evaporator to obtain a golden yellow liquid that is bis(3 -Phenyl-6-aldehyde-3,4-dihyd...

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Abstract

An aldehyde-containing benzoxazine intermediate and a preparation method thereof, which are characterized in that (1) 50-180 parts by weight of a solvent is added at a temperature of 4-20°C to 280-30 parts by weight of R-NH and 20-110 parts by weight of formaldehyde The reaction generates the N-dimethylol compound, and the pH value is adjusted between 8-10 with lye, so that the N-dimethylol compound is stable in the solution; (2) adding 20-70 weight of aldehyde-containing phenol derivative The N-dimethylol compound is condensed with the phenolic hydroxyl group and its ortho-position on the benzene ring, and dehydration and ring-closure are performed to form an aldehyde-containing benzoxazine intermediate solution. The solvent was distilled off from this solution under reduced pressure to obtain a yellow aldehyde group-containing benzoxazine intermediate solid.

Description

technical field [0001] The invention relates to an aldehyde group-containing benzoxazine intermediate and a preparation method, and belongs to the field of thermosetting resin and its preparation. Background technique [0002] Benzoxazine is a kind of benzo six-membered heterocyclic ring system composed of oxygen atom and nitrogen atom. It has the characteristics of ring-opening polymerization, no small molecules are released during polymerization, and a network structure similar to phenolic resin is formed after polymerization. Small curing shrinkage, low porosity, excellent mechanical properties, electrical properties and flame retardant properties. In the 1940s, foreign countries conducted systematic research on the reaction of phenolic intermediates, amine intermediates and formaldehyde, and synthesized intermediates containing benzoxazine ring structures: [0003] [0004] Since the 1970s, foreign countries have carried out preliminary research on the ring-opening p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D265/16
Inventor 顾宜冉起超田巧朱蓉琪凌鸿刘向阳
Owner SICHUAN UNIV
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