Benzoxazine resin containing Schiff base structure benzoxazine monomer and preparation thereof

A technology of benzoxazine and monomer, which is applied in the field of thermosetting liquid crystal resin materials to achieve the effect of excellent heat resistance and thermal conductivity

Inactive Publication Date: 2013-04-24
GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, it has emerged to improve its heat resistance and electrical properties by introducing the ordered structure of liquid crystals into benzoxazine resins. Japan (Polymer 52 (2011) 2150-2156) and the United States (Journal of Polymer Science: Part A: Polymer Chemistry, Vol.47, 5871-5881 (2009)) has done relevant substantive work in this area, but our domestic work in this area is still in a blank stage

Method used

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  • Benzoxazine resin containing Schiff base structure benzoxazine monomer and preparation thereof
  • Benzoxazine resin containing Schiff base structure benzoxazine monomer and preparation thereof
  • Benzoxazine resin containing Schiff base structure benzoxazine monomer and preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] (1) Synthesis of bisphenols containing Schiff base

[0054] in stock N 2 In the reaction flask of gas feeding device, stirring device, thermometer, condensate pipe, add 20g terephthalaldehyde, 30g p-aminophenol, and be dissolved in dimethyl sulfoxide / ethanol mixed solvent A (dimethyl sulfoxide: ethanol =1:2, V / V), add 0.6g ZnCl 2 as a catalyst. Access to N 2 , heated to 80 ° C, stirred and refluxed for 3 hours, and cooled to room temperature, a large number of yellow crystals precipitated. Suction filtration, washed with deionized water 3 times, placed in a vacuum oven, dried at 75°C for 24 hours, and the obtained product was then mixed with dimethyl sulfoxide / ethanol solvent B (dimethyl sulfoxide:ethanol=1:8 , V / V) and recrystallized to obtain 46g of dihydric phenol containing Schiff base, referred to as DP-1.

[0055] DP-1: mass spectrum (MS), m / z=316[M+]; C 20 h 16 N 2 o 2 : Elemental analysis (Elemental analysis, EA): found% (Calc.%): C: 75.77 (75.93), H: 5...

Embodiment 2

[0063] (1) Synthesis of bisamines containing Schiff bases

[0064] in stock N 2 Add 88g of 1,4-butanediamine and dissolve it in 150mL dimethyl sulfoxide / ethanol mixed solvent A (dimethyl sulfoxide:ethanol=1: 2, V / V), add 0.6g ZnCl 2 as a catalyst. Dissolve 13.4 g of terephthalaldehyde in 100 mL of DMSO, and then add the solution dropwise into the reaction flask (3 hours to complete the dropwise addition). Access to N 2 , heated to 90°C, stirred and refluxed for 3h, and cooled to room temperature, a large number of yellow crystals precipitated. Suction filtration, washed with deionized water 3 times, placed in a vacuum oven, dried at 55°C for 24 hours, and the obtained product was then mixed with methyl sulfoxide / ethanol solvent B (dimethyl sulfoxide:ethanol=1:8, V / V) recrystallized to obtain 19.7g of diamine containing Schiff base, which is called PD-1 for short.

[0065] PD-1: MS, m / z=274[M+]; C 32 h 38 N 4 o 2 : Elemental analysis (EA): found% (Calc.%): C: 69.83 (7...

Embodiment 3

[0073] (1) The dihydric phenol DP-1 containing Schiff base in Case 1 was used as the raw material.

[0074] (2) Synthesis of benzoxazine monomers with Schiff base structure

[0075] In a reaction vessel with a stirrer and a thermometer, 150mL of dimethyl sulfoxide / ethanol mixed solvent A (dimethyl sulfoxide:ethanol=1:2, V / V), 12.12g of paraformaldehyde and 20.2g of 1 -Hexylamine was reacted at 40°C for 1 hour. Then, 31.6 g of DP-1 was added to the reaction mixture, and the temperature was raised to 105° C. for 4 h under stirring. After cooling to room temperature after completion of the reaction, a large number of light yellow crystals precipitated. Filter with suction, wash with 0.5M NaOH solution three times, then wash with deionized water until neutral, place in a vacuum oven, and dry at 75°C for 24h. The obtained product was recrystallized with dimethyl sulfoxide / ethanol mixed solvent B (dimethyl sulfoxide:ethanol=1:8, V / V) to obtain 51.8g of benzoxazine monomer contain...

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Abstract

The invention discloses a benzoxazine resin containing Schiff base structure benzoxazine monomer and a preparation thereof, belonging to the filed of thermosetting liquid crystal resin. Diamine or bisphenol containing Schiff base structure is obtained by using aliphatic diamine and terephthalaldehyde or terephthalaldehyde and parahydroxyaniline as raw materials; and a benzoxazine monomer containing Schiff base structure is obtained by reacting the diamine or bisphenol containing Schiff base structure, paraformal-dehyde with straight chain fatty primary amines or monophenol and derivates thereof. The benzoxazine monomer containing Schiff base structure reacts with a curing reaction accelerating agent at the temperature of 150-165 DEG C so that the benzoxazine resin containing Schiff base structure is obtained. The benzoxazine resin containing Schiff base structure prepared in the invention is excellent is resistance to heat and heat conductivility, and is suitable for wide application in the fields of electronics industry and space flight and aviation.

Description

technical field [0001] The invention belongs to the field of thermosetting liquid crystal resin materials, and in particular relates to a benzoxazine monomer containing a Schiff base structure, a benzoxazine resin and a preparation method thereof. Background technique [0002] After some substances are heated or dissolved by flux, although they lose the rigidity of solid substances and obtain the fluidity of liquid substances, they still partially retain the orderly arrangement of crystalline substances, thus presenting anisotropy in physical properties , forming a transition state with both crystal and liquid properties, this intermediate state is called liquid crystal state, and the substance in this state is called liquid crystal. [0003] Thermosetting liquid crystal resin is a new type of liquid crystal resin developed on the basis of thermotropic liquid crystal polymers. It is generally composed of mesogens, flexible spacer chains and reactive groups, so it has the dua...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D265/16C08G73/06C09K19/38C09K19/34
Inventor 许凯苏江勋付子恩陈鸣才
Owner GUANGZHOU CHEM CO LTD CHINESE ACADEMY OF SCI
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