Preparation method of benzoxazine intermediate containing active function groups

A technology of active functional group and benzoxazine, applied in the field of thermosetting resin and its preparation, can solve the problems of low thermal performance, invisible, poor toughness, etc., and achieve the effect of lowering curing temperature, reducing dosage, and high heat resistance

Inactive Publication Date: 2007-09-26
SHANDONG UNIV
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  • Abstract
  • Description
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  • Application Information

AI Technical Summary

Problems solved by technology

[0005] For the dihydric phenol and diamine system benzoxazine with similar structures, the diamine system benzoxazine has higher thermal performance, but the toughness is relatively poor; while the dihydric phenol system has higher Tough, but relatively low thermal performance
However, after searching, there is no information about using diamine, dihydric phenol and formaldehyde as reaction raw materials, introducing diamine and dihydric phenol units into benzoxazine intermediates to synthesize benzoxazine intermediates containing active functional groups. Body research and reports

Method used

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  • Preparation method of benzoxazine intermediate containing active function groups
  • Preparation method of benzoxazine intermediate containing active function groups
  • Preparation method of benzoxazine intermediate containing active function groups

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034]Example 1 Synthesis of 3-hexylamino-6-p-hydroxycumene-3,4-dihydro-2H-1,3-benzoxazine

[0035] Add 75ml of chloroform, 0.7g of triethylamine and 5.15g of paraformaldehyde in sequence into a 250ml three-necked flask equipped with a stirrer and a condenser, and stir to mix. Slowly add 9.3g of hexamethylenediamine, control the reaction temperature not to exceed 30°C, add 18.3g of bisphenol A after 15 minutes of reaction, raise the temperature to reflux, and stop the reaction after the mixed solution reacts at reflux temperature for 5 hours to obtain a light yellow oil in the lower layer phase, a phase-separation system of the upper transparent aqueous phase. The reaction product was poured into excess methanol for precipitation, and filtered with 1N NaHCO 3 The aqueous solution was washed three times, distilled under reduced pressure and dried in vacuo to obtain a white powder namely 3-hexylamino-6-p-hydroxycumene-3,4-dihydro-2H-1,3-benzoxazine, the yield 85%.

Embodiment 2

[0036] Example 2 Synthesis of 3-ethylamino-6-p-hydroxybenzophenone-3,4-dihydro-2H-1,3-benzoxazine

[0037] Add 75ml of chloroform, 0.7g of triethylamine and 24ml of formaldehyde solution in sequence to a 250ml three-neck flask equipped with a stirrer and a condenser, and stir to mix. Slowly add 4.5g of ethylenediamine, control the reaction temperature not to exceed 30°C, add 16.1g of 4,4'-p-hydroxybenzophenone after 15 minutes of reaction, raise the temperature to reflux, react the mixed solution at the reflux temperature for 5 hours, and then stop the reaction . The reaction mixture was filtered and washed with 1N NaHCO 3 The aqueous solution was washed three times, distilled under reduced pressure and dried under vacuum to obtain a white powder, namely 3-ethylamino-6-p-hydroxybenzophenone-3,4-dihydro-2H-1,3-benzoxazine, with a yield of 80 %.

Embodiment 3

[0038] Example 3 Synthesis of 3-p-aminodiphenylmethane-6-p-hydroxycumene-3,4-dihydro-2H-1,3-benzoxazine

[0039] Add 75ml of chloroform, 0.7g of triethylamine and 24ml of formaldehyde solution in sequence to a 250ml three-neck flask equipped with a stirrer and a condenser, and stir to mix. Slowly add 14.9g of diphenylmethanediamine, control the reaction temperature not to exceed 30°C, add 17.1g of bisphenol A after 15 minutes of reaction, raise the temperature to reflux, react the mixed solution at reflux temperature for 5 hours, stop the reaction, and obtain a light yellow lower layer A phase-separation system with an oil phase and an upper transparent water phase. The reaction product was poured into methanol for precipitation, and filtered with 1N NaHCO 3 After washing with aqueous solution, distilling under reduced pressure and drying in vacuo, a white powder was obtained, namely 3-p-aminodiphenylmethane-6-p-hydroxyisopropylbenzene-3,4-dihydro-2H-1,3-benzoxazine, Yield 8...

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Abstract

The invention discloses a making method of benzoxazine intermediate with active functional group, which is characterized by the following: adopting diamine, dihydric phenol and formaldehyde as raw material; introducing the unit of diamine and dihydric phenol into the intermediate of benzoxazine; polymerizing under heating condition; reducing the ring-opening polymerizing temperature of benzoxazine; fitting for making high-property structural material, electric insulating material, electronic packing material, flame-proof material or braking material with temperature over 155 deg.c.

Description

technical field [0001] The invention belongs to the technical field of thermosetting resins and their preparation, and in particular relates to a novel benzoxazine intermediate containing active functional groups and a preparation method thereof. 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 excellent thermal properties, mechanical properties, electrical properties and flame retardancy, but also overcomes the shortcomings of traditional phenolic resins in releasing small molecules during the forming and curing process. Low, near zero shrinkage. [0003] Si...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D265/16C08G73/06C08G12/40
Inventor 鲁在君门薇薇张洪春
Owner SHANDONG UNIV
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