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Organic liquid crystal friction modifiers with alkyl end chains and preparation method thereof

A friction modifier and organic technology, applied in the field of lubricants, can solve the problems of great influence of anti-wear and anti-friction effects, differences in tribological properties, etc., and achieve the effects of strong low temperature solubility, good lubricating performance, and easy biodegradation

Active Publication Date: 2020-07-28
SHANGHAI ADVANCED RES INST CHINESE ACADEMY OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Through research, they also found that the liquid crystal phase range of liquid crystal additives has a great influence on its anti-wear and anti-friction effects, and there are great differences in the tribological properties of liquid crystal phases in different temperature ranges.

Method used

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  • Organic liquid crystal friction modifiers with alkyl end chains and preparation method thereof
  • Organic liquid crystal friction modifiers with alkyl end chains and preparation method thereof
  • Organic liquid crystal friction modifiers with alkyl end chains and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] The compound preparation of n=6 in the embodiment 1 formula (I)

[0035] Put 34.5g of p-hydroxybenzoic acid and 13.8g of hydroquinone into a 500mL three-necked bottle, and pour 0.5g of p-toluenesulfonic acid and 300mL of solvent toluene into the bottle. Install an oil-water separator above the three-necked bottle, raise the temperature to 70°C, keep the temperature constant for 30 minutes, then gradually raise the temperature to reflux, and react for 30 hours. After the reaction was completed, the crude product was obtained by filtration. The crude product was recrystallized from absolute ethanol to obtain intermediate product A with a yield of 82% and a measured melting point of 340°C.

[0036] Put 2.97g of n-heptanoic acid and 7g of dicyclohexylcarbodiimide (DCC) in 100mL of dioxane, magnetically stir until completely dissolved, and cool to -20°C in an ice-salt bath. Dissolve 2g of intermediate product A and 0.37g of 4-dimethylaminopyridine (DMAP) in 50mL of dioxane...

Embodiment 2

[0038] The compound preparation of n=8 in the embodiment 2 formula (I)

[0039] Put 3.61g of nonanoic acid and 7.1g of dicyclohexylcarbodiimide (DCC) in 100mL of dimethylformamide, magnetically stir until completely dissolved, and cool to -20°C in an ice-salt bath. Dissolve 2g of intermediate product A and 0.37g of 4-dimethylaminopyridine (DMAP) in 50mL of dimethylformamide, and slowly add it dropwise to the reaction system, and carry out the reaction at 0-10°C for 24 hours, and then naturally rise to room temperature React for 10 hours. After the reaction was complete, 3 mL of deionized water was added to the flask to quench the reaction. The reaction solution was extracted and washed with 1M hydrochloric acid solution, saturated sodium bicarbonate solution and saturated sodium chloride solution respectively, and the collected organic layer was rotary evaporated to remove the solvent to obtain a crude product. The crude product was recrystallized with absolute ethanol at 50...

Embodiment 3

[0041] Preparation of the compound of n=9 in the formula (I) of embodiment 3

[0042] Put 3.93g of n-decanoic acid and 6.1g of dicyclohexylcarbodiimide (DCC) in 100mL of dimethylformamide, magnetically stir until completely dissolved, and cool to -20°C in an ice-salt bath. Dissolve 2g of intermediate product A and 0.37g of 4-dimethylaminopyridine (DMAP) in 50mL of dimethylformamide, and slowly add it dropwise to the reaction system, and carry out the reaction at 0-10°C for 24 hours, and then naturally rise to room temperature React for 10 hours. After the reaction was complete, 3 mL of deionized water was added to the flask to quench the reaction. The reaction solution was extracted and washed with 1M hydrochloric acid solution, saturated sodium bicarbonate solution and saturated sodium chloride solution respectively, and the collected organic layer was rotary evaporated to remove the solvent to obtain a crude product. The crude product was recrystallized with absolute ethan...

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Abstract

The invention discloses organic liquid crystal friction modifiers with alkyl end chains and a preparation method of the organic liquid crystal friction modifiers. According to the preparation method,p-hydroxybenzoic acid and hydroquinone are subjected to an esterification reaction to obtain an intermediate product A, and the intermediate product A is subjected to an esterification reaction with straight-chain carboxylic acids having different carbon chain lengths (wherein a carbon number is in a range of 5 to 21) to obtain compounds as shown in the formula (I). The series of phenyl terephthalate compounds with the alkyl end chains having different lengths are synthesized from three benzene rings connected via ester groups and long-chain n-carboxylic acid; and through the synergistic effect of the polarity of the ester groups, the oil solubility of long-chain alkyl groups, the rigidity influence of the three benzene rings of the compounds and the specific lubricating properties of liquid crystal materials of the compounds, the series of compounds have the performance suitable for being used as lubricating grease additives.

Description

technical field [0001] The invention belongs to the technical field of lubricants, and in particular relates to an organic liquid crystal friction modifier with different lengths of alkyl end chains and a preparation method thereof. Background technique [0002] Lubricating grease is widely used in various fields of industry. Improving the performance of lubricating grease is of great significance to saving energy, raw materials and prolonging the service life of machinery. Lubricating grease is generally composed of base oil and additives, and the additives are divided into several types, such as detergents, dispersants, antioxidants, anti-corrosion agents, extreme pressure and anti-wear agents, friction modifiers, etc. Among them, the friction modifier has been applied and upgraded for many years. It was originally limited to industrial application fields such as gear oil, automatic transmission fluid, and guide rail oil, and gradually developed into civilian fields such a...

Claims

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Application Information

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IPC IPC(8): C10M129/95C07C67/30C07C69/90C10N30/06
CPCC10M129/95C07C67/30C10M2207/30C07C69/90
Inventor 姜滢李久盛廖廷君赵永清朱德林倪杰
Owner SHANGHAI ADVANCED RES INST CHINESE ACADEMY OF SCI
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