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Biphenyl-containing compound liquid crystal epoxy resin and preparation method thereof

An epoxy resin, composite technology, applied in liquid crystal materials, chemical instruments and methods, organic chemistry and other directions, can solve the problems of uneconomical synthesis methods and low yields, improve appearance quality, high reaction conversion rate, prevent The effect of oxidation

Inactive Publication Date: 2011-02-02
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Cai Zhiqi, Sun Jianzhong and others (Journal of Chemical Engineering of Chinese Universities, 23(3), 2009, 510; Journal of Polymer Science, Part A: Polymer Science: 2007, 45, 727) reported that 4,4'-bis (4-Hydroxybenzyloxy)-3,3',5,5'-tetramethylbiphenyl diglycidyl ether, the cured product has high heat resistance and retains its liquid crystallinity in the cured network , but the yield of this method is very low, and the synthesis method is uneconomical

Method used

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  • Biphenyl-containing compound liquid crystal epoxy resin and preparation method thereof
  • Biphenyl-containing compound liquid crystal epoxy resin and preparation method thereof
  • Biphenyl-containing compound liquid crystal epoxy resin and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Step 1: Synthesis of 2-p-hydroxybenzoic acid-3,3′,5,5′-tetramethoxybiphenyl-4,4′-diester

[0030] Under nitrogen protection, p-hydroxybenzoic acid (0.2mol, 27.6g), 3,3',5,5'-tetramethoxybiphenyl-4,4'-diphenol (0.05mol, 15.3g), p- Toluenesulfonic acid (3mmol, 0.54g) and sulfolane (80ml) were added to a three-necked flask equipped with a stirring bar, water trap and thermometer and stirred at 220°C for 6h. The water formed during the reaction was continuously removed. After the reaction mixture was cooled to room temperature, it was poured into 500 ml of water, and the filter cake obtained after filtration was repeatedly washed with water and ethanol. Dip-hydroxybenzoic acid-3,3',5,5'-tetramethoxybiphenyl-4,4'-diester (23.3 g) was finally obtained as a white powder. Yield: 85.4%.

[0031] Step 2: Synthesis of bis(4-(2,3-epoxypropoxy)benzoic acid)-3,3',5,5'-tetramethoxybiphenyl-4,4'-diester

[0032] Under nitrogen protection, di-p-hydroxybenzoic acid-3,3',5,5'-tetramet...

Embodiment 2

[0037] The synthetic method of the present embodiment is:

[0038]

[0039] Step 1: Synthesis of 2-p-hydroxybenzoic acid-3,3′,5,5′-tetramethylbiphenyl-4,4′-diester

[0040] Under nitrogen protection, p-hydroxybenzoic acid (0.2mol, 27.6g), 3,3', 5,5'-tetramethylbiphenyldiphenol (0.05mol, 12.1g), p-toluenesulfonic acid (5mmol , 0.9g) and sulfolane (50ml) were added to a three-necked flask with a stirring bar, a water trap and a thermometer and stirred at 180°C for 4h. The water formed during the reaction was continuously removed. After the reaction mixture was cooled to room temperature, it was poured into 500 ml of water, and the filter cake obtained after filtration was repeatedly washed with water and ethanol. Dip-hydroxybenzoic acid-3,3',5,5'-tetramethylbiphenyl-4,4'-diester (19.3 g) was finally obtained as a white powder. Yield: 80.1%.

[0041] Step 2: Synthesis of bis(4-(2,3-epoxypropoxy)benzoic acid)-3,3',5,5'-tetramethylbiphenyl-4,4'-diester

[0042] Under nitrog...

Embodiment 3

[0045] The synthetic method of the present embodiment is:

[0046]

[0047] image 3

[0048] Step 1: N,N'-bis(4-hydroxyphenylmethylene)-2,2',3,3',5,5',6,6'-octafluorobiphenyl-4,4'- Synthesis of diamines

[0049] Under nitrogen protection, p-hydroxybenzaldehyde (0.2mol, 24.4g), 2,2',3,3',5,5',6,6'-octafluorobiphenyl-4,4'-diamine ( 0.05mol, 16.4g) and dimethylsulfoxide (40ml) were added to a three-necked flask with a stirring bar and a thermometer and stirred at 100°C for 3h. After the reaction mixture was cooled to room temperature, it was poured into 500 ml of water, and the filter cake obtained after filtration was repeatedly washed with water and ethanol. Finally, N,N'-bis(4-hydroxyphenylmethylene)-2,2',3,3',5,5',6,6'-octafluorobiphenyl-4 was obtained as pink powder , 4'-diamine (25.5 g). Yield: 95.2%.

[0050] Step 2: N,N'-bis(4-(2,3-epoxypropoxy)-phenylmethylene)-2,2',3,3',5,5',6,6' -Synthesis of octafluorobiphenyl-4,4'-diamine

[0051] Under nitrogen protection...

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Abstract

The invention provides a biphenyl-containing compound liquid crystal epoxy resin and a preparation method thereof. The biphenyl-containing compound liquid crystal epoxy resin has a structure represented by a formula (1), wherein the -X-Y-, which represents a bridge bond for connecting an aromatic group to a rigid rod mesomorphic structure, may be -C(=O)-O- or-CH=N-; and R1, R2, R3 and R4 and R'1, R'2, R'3 and R'4 has a substituent group which may be -H, -F, -Cl, -Br, -CH3, -C2H5, -OCH3 or -OC2H5. The resin makes full use of the liquid crystal epoxy resin (LCER) thermal performance, and has high comprehensive mechanical performance. The preparation method comprises performing a reaction for generating bisphenol which a liquid crystal epoxy resin intermediate and reacting the bisphenol intermediate with epoxy chloropropane to form the liquid crystal epoxy resin.

Description

technical field [0001] The invention relates to a liquid crystal epoxy resin (LCER), in particular to a biphenyl composite type liquid crystal epoxy resin containing a substituent and a preparation method thereof. Background technique [0002] Epoxy resin is an important thermosetting polymer. Because of its good bonding performance, high mechanical strength, good electrical insulation, and small curing shrinkage, it is widely used in machinery, electronics, aviation, aerospace, chemical industry, transportation, etc. Transportation, construction and other fields. However, because the cured product is a three-dimensional network structure with high crosslink density, the material has poor crack growth resistance and toughness, which limits its use in some special fields. In recent years, the synthesis of epoxy compounds containing rigid rod mesogens, that is, liquid crystal epoxy resin (LCER), during the curing process, the mesogens are prone to orientation and form a self-...

Claims

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Application Information

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IPC IPC(8): C09K19/34C07D301/28C07D303/23
Inventor 蔡智奇刘银玲皮丕辉文秀芳程江杨卓如
Owner SOUTH CHINA UNIV OF TECH
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