Method for preparing benzoxazine intermediate containing propargyl ether and resin thereof

A technology of propargyl ether and benzoxazine, which is applied in the field of thermosetting resin and its preparation, to achieve the effects of low toxicity, high heat resistance and good thermal performance

Inactive Publication Date: 2008-08-06
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there has been no report so far using compounds such as phenolphthalein, dinaphthol, binaphthol, p-(...

Method used

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  • Method for preparing benzoxazine intermediate containing propargyl ether and resin thereof
  • Method for preparing benzoxazine intermediate containing propargyl ether and resin thereof

Examples

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Embodiment 1

[0038] 3,3'-bis(3-(4-propargyl ether)phenyl-3,4-dihydro-2H-1,3-benzoxazine)-1(3H)-isobenzofuranone The synthesis of p-aminophenyl propargyl ether, phenolphthalein and formaldehyde is the preparation process of raw material synthesis benzoxazine resin:

[0039] Add 100ml of dioxane, 0.7g of triethylamine and 19ml of 37% formaldehyde solution in sequence into a 250ml three-neck flask equipped with a stirrer and a condenser, and stir to mix. Slowly add 14.7g p-aminophenyl propargyl ether, control the reaction temperature not to exceed 30°C, and adjust the pH value to 7 with triethylamine to generate N-dimethylol compound and keep it stable in the solution; react for 15 minutes Then add 16g of phenolphthalein, raise the temperature to reflux, and stop the reaction after reacting the mixed solution at the reflux temperature for 5 hours, so that the N-dimethylol compound and the phenolic hydroxyl group and its ortho-position on the benzene ring will undergo condensation reaction, de...

Embodiment 2

[0043] 3,3'-bis(3-(2-propargyl ether)phenyl-3,4-dihydro-2H-1,3-benzoxazine)-1(3H)-isobenzofuranone The synthesis of o-aminophenyl propargyl ether, phenolphthalein and formaldehyde is the preparation process of raw material synthesis benzoxazine resin:

[0044] Add 90ml of dioxane, 0.84g of triethylamine and 21ml of 36% formaldehyde solution in sequence into a 250ml three-neck flask equipped with a stirrer and a condenser, and stir to mix. Slowly add 16.5g o-aminophenyl propargyl ether, control the reaction temperature not to exceed 30°C, and adjust the pH value to 7 with triethylamine to generate N-dimethylol compound and keep it stable in the solution; react for 15 minutes Then add 18g of phenolphthalein, raise the temperature to reflux, and stop the reaction after reacting the mixed solution at the reflux temperature for 5 hours, so that the N-dimethylol compound and the phenolic hydroxyl group and its ortho position on the benzene ring will undergo condensation reaction, an...

Embodiment 3

[0048] 3,3'-bis(3-(3-propargyl ether)phenyl-3,4-dihydro-2H-1,3-benzoxazine)-1(3H)-isobenzofuranone The synthesis of, take m-aminophenyl propargyl ether, phenolphthalein and formaldehyde as the preparation technology of raw material synthetic benzoxazine resin:

[0049] Add 110ml of dioxane, 0.7g of triethylamine and 16ml of 35% formaldehyde solution in sequence into a 250ml three-neck flask equipped with a stirrer and a condenser, and stir to mix. Slowly add 14.7g m-aminophenyl propargyl ether, control the reaction temperature not to exceed 30°C, and adjust the pH value to 7 with triethylamine to generate N-dimethylol compound and keep it stable in the solution; react for 15 minutes Then add 14g of phenolphthalein, raise the temperature to reflux, and stop the reaction after reacting the mixed solution at the reflux temperature for 5 hours, so that the N-dimethylol compound and the phenolic hydroxyl group and its ortho position on the benzene ring will undergo condensation rea...

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Abstract

The invention discloses a new benzoxazine intermediate containing propargyl ether and a preparation method of relative polymer. The synthesis route comprises using monoamine containing propargyl ether group, dihydric phenol (or polyhydric phenol) containing rigid structure and formaldehyde as reaction materials to synthesize benzoxazine intermediate containing propargyl ether, solidifying and crosslinking to obtain thermosetting high-performance benzoxazine resin containing propargyl ether which has excellent heat resistance and glass transition point reaches 300DEG C. The inventive benzoxazine intermediate containing propargyl ether can be independently used or mixed with other benzoxazine intermediates, benzoxazine intermediate containing propargyl ether a or epoxy resin, while the solidified product has excellent heat resistance and the application for producing structural material, electric insulated material, electronic packaging material, fireproof material, glowing resistant material and brake material applied above 250DEG C.

Description

technical field [0001] The invention belongs to the technical field of thermosetting resin and its preparation, and in particular relates to a novel benzoxazine intermediate containing propargyl ether and a method for preparing the resin. Background technique [0002] Benzoxazines are a class of six-membered heterocyclic compounds synthesized by polycondensation reactions of phenolic compounds, amine compounds and formaldehyde. They were initially discovered in the Mannich reaction, and undergo ring-opening polymerization under the action of heating or catalysts to form nitrogen-containing and similar Network structure of phenolic resin. As a new type of phenolic resin, benzoxazine resin not only has the thermal properties, mechanical properties, and electrical properties of traditional phenolic resins, but also has excellent processing properties: no small molecules are released during the forming and curing process, and the volume is close to zero shrinkage , which has ar...

Claims

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Application Information

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IPC IPC(8): C08G61/12C07D413/14C07D413/04C07D498/04C07D498/14
Inventor 鲁在君门薇薇张洪春孔令泉
Owner SHANDONG UNIV
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