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Naphthalene-containing liquid crystal epoxy resin compound, its preparation method and composition

A technology for epoxy resins and compounds, applied in chemical instruments and methods, liquid crystal materials, organic chemistry, etc., can solve problems such as side reactions, yield reduction, etc., to improve yield, improve heat resistance, and improve product purity. Effect

Active Publication Date: 2015-12-09
SHENZHEN INST OF ADVANCED TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the instability of olefins, it is easy to have side reactions in subsequent reactions, reducing the yield

Method used

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  • Naphthalene-containing liquid crystal epoxy resin compound, its preparation method and composition
  • Naphthalene-containing liquid crystal epoxy resin compound, its preparation method and composition
  • Naphthalene-containing liquid crystal epoxy resin compound, its preparation method and composition

Examples

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preparation example Construction

[0027] In the preparation method of the present invention, the double bond oxidation method is adopted to form the skeleton structure and then the alkenyl is introduced, and then the alkenyl is epoxidized with a peroxidant, thereby greatly reducing the by-products in the reaction and improving the purity and reaction of the product. yield, and also simplifies the purification operation. The product can be isolated and purified, for example, by simple column chromatography. Moreover, due to the double bond oxidation method, the reaction can be carried out in a wider time range and a larger temperature range, and the reaction control is more convenient.

[0028] Specifically, the catalyst used in step S1 can be 18-crown-6-ether, 15-crown-5-ether, dibenzo-18-crown-6-ether, or any mixture thereof; the catalyst and the The molar ratio of the phenolic compounds can be (0.005-0.5): 1; an appropriate amount of potassium carbonate, sodium carbonate, sodium hydroxide, sodium bicarbonat...

Embodiment 1

[0040] 0.05 mol of p-hydroxybenzoic acid was acylated under the catalysis of 10 parts of acetic anhydride, and reacted at 80° C. for 5 hours to obtain acetoxybenzoic acid.

[0041] 0.03mol of acetoxybenzoic acid and 0.013mol of 2,7-dihydroxynaphthalene were dissolved in 80ml of acetone, with pyridine and thionyl chloride as catalysts, reacted at 0°C for 12 hours, and separated by chromatography to obtain 4,4'-bis( 4-acetoxybenzyloxy)-2,7-naphthalene.

[0042] 0.011mol 4,4'-bis(4-acetoxybenzyloxy)-2,7-naphthalene was dissolved in 60ml acetone, under the catalysis of ammonia water, reacted at room temperature for 12 hours to obtain 4,4'-bis(4-hydroxy Benzyloxy)-2,7-naphthalene.

[0043]Dissolve 0.01mol 4,4′-bis(4-hydroxybenzyloxy)-2,7-naphthalene and 0.011mol propylene bromide in acetone, add appropriate amount of potassium carbonate and 18-crown-6-ether, and react at 65°C for 24 product obtained in hours. After purification by column chromatography, it was dissolved in dichl...

Embodiment 2

[0047] 0.05 mol of p-hydroxybenzoic acid was acylated under the catalysis of 12 parts of acetyl chloride, and reacted at 90° C. for 5 hours to obtain acetoxybenzoic acid.

[0048] 0.03mol of acetoxybenzoic acid and 0.013mol of 2,7-dihydroxynaphthalene were dissolved in 80ml of acetone, with pyridine and thionyl chloride as catalysts, reacted at -3°C for 12 hours, and separated by chromatography column to obtain 4,4'-bis (4-Acetoxybenzyloxy)-2,7-naphthalene.

[0049] 0.011mol 4,4'-bis(4-iminobenzyloxy)-2,7-naphthalene was dissolved in 70ml tetrahydrofuran, under the catalysis of ammonia water, reacted at room temperature for 12 hours to obtain 4,4'-bis(4-hydroxybenzene imino)-2,7-naphthalene.

[0050] Dissolve 0.01mol 4,4′-bis(4-hydroxybenzyloxy)-2,7-naphthalene and 0.011mol chloropropene in tetrahydrofuran, add appropriate amount of potassium bicarbonate and 18-crown-6-ether, and react at 80°C The product obtained in 24 hours. After purification by column chromatography, it...

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Abstract

The invention relates to the field of liquid crystal solidifying agent, in particular to an epoxy resin compound of liquid crystal containing naphthalene with the following formula (I) (which is shown in the specification), wherein the -Y-X- is -C(double bond O)-O-, -CH double bond N-, or -NH-C(double bond O)-. The preparation of the epoxy resin compound of liquid crystal containing naphthalene comprises the following steps: S1, the compound (II) (of which formula is shown in the specification) is caused to react with chloropropene or bromopropene under alkali condition in the presence of catalyst to produce corresponding allyl ether compound; S2, epoxidation: the allyl ether compound is caused to react with a peroxidation agent to produce compound (I); the liquid crystal solidified composition containing epoxy resin compound of liquid crystal containing naphthalene comprises epoxy resin compound (I) and solidifying agent according to the molar ratio of 1:(0.5-1.2). According to the invention, naphthalene nucleus is introduced to the epoxide framework, the heat resistance is improved while the liquid property is kept; the full symmetry structure is adopted for further improving the heat resistance of the compound; the double bond oxidation method is adopted for preparation, so that the productivity and the product purity are increased; the composition can be used as a heat resistance liquid crystal material.

Description

【Technical field】 [0001] The invention relates to the field of liquid crystal curing agents, in particular to a naphthalene-containing liquid crystal epoxy resin compound, a preparation method and a composition thereof. 【Background technique】 [0002] The performance of the epoxy resin curing composition mainly depends on the molecular structure of the epoxy resin and the curing agent. Therefore, there are four main ways to improve the heat resistance of the epoxy resin: changing the heat-resistant skeleton structure of the epoxy resin; synthesizing multiple Functional epoxy resin, increase the cross-linking density of cured epoxy resin; use a curing agent with better heat resistance; use other high-performance resins for blending or copolymerization modification. [0003] From the perspective of synthesis, the synthesis of heat-resistant epoxy resins with new structures is a major approach. Introducing rigid groups such as benzene ring, naphthalene ring, biphenyl, aliphati...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D303/30C07D301/14C09K19/34C08G59/24C08G59/28C08G59/40
Inventor 张国平林尤谊孙蓉郭慧子
Owner SHENZHEN INST OF ADVANCED TECH
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