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Lactone aromatic derivatives containing mesogen and preparation method thereof, side chain type liquid crystal polymer, preparation method and application thereof

A liquid crystal element and derivative technology, applied in liquid crystal materials, chemical instruments and methods, organic chemistry, etc., can solve the problems of expensive metal catalysts, low yield, wide molecular weight distribution, etc., and achieve cheap and easy to obtain catalysts, synthetic The effect of simple steps and narrow molecular weight distribution

Active Publication Date: 2021-06-29
WANHUA CHEM GRP CO LTD
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  • Abstract
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  • Claims
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Problems solved by technology

But at the same time, there are some problems in the above method: 1) the synthesis process of mesogen-containing monomers has many steps, many side reactions, and low yield, such as the polymerization of acrylate monomers due to conditions such as light and heat; 2 ) The polymer produced cannot be precisely controlled according to the design, such as a large deviation between the average molecular weight and the design, a wide molecular weight distribution, and incomplete reactions in the addition of hydrosilylation. The side chain intervals can only be -C-C-, -Si-O-, -C-C-C-O-, and it is impossible to synthesize side chain type liquid crystal polymers with different mesogen density in the main chain; 3) ring-opening polymerization / hydrosilylation The use of noble metal catalysts in the process is expensive
Due to the poor control of the polymerization process of traditional tin salts and the tendency to remain in the polymer, resulting in cytotoxicity and poor performance of the polymer, researchers have developed many new catalytic systems for ring-opening polymerization of lactones (such as the patent CN105348495A, CN105399932A and CN101107288A proposed bifunctional group ionic liquid, organic sulfonic acid, active carbon powder catalyst and Pseudomonas cepacia lipase, organic carboxylic acid, thiourea-amine bifunctional catalyst disclosed in the literature respectively)
[0018] At the same time, the researchers also investigated the structure research of the current lactone derivatives, and found that the lactone derivatives have a wide range of biological activities and good antibacterial, antiviral, tumor cell inhibition and other pharmacological effects, such as anti-inflammatory antibacterial and immune Stimulating andrographolide derivatives, antiarrhythmic biaryl seven-membered lactone and widely used macrolide derivatives, etc. Therefore, the research on the synthesis of lactone derivatives is currently mainly concentrated in the fields of biology and pharmaceuticals. The derivatives involved do not contain mesogens, and there is no precedent for the synthesis of side chain liquid crystal polymers directly

Method used

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  • Lactone aromatic derivatives containing mesogen and preparation method thereof, side chain type liquid crystal polymer, preparation method and application thereof
  • Lactone aromatic derivatives containing mesogen and preparation method thereof, side chain type liquid crystal polymer, preparation method and application thereof
  • Lactone aromatic derivatives containing mesogen and preparation method thereof, side chain type liquid crystal polymer, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0090] (1) Synthesis of 3-(2-chloroethyl)-1,5-dichloropentane

[0091]

[0092] Add 20 g of 3-ethyl-pentane to a three-necked round-bottom flask connected with a stirrer and a condenser, vacuumize and replace with nitrogen 5 times, and add 200 g of chloroform and 120 g of thionyl chloride under the protection of a nitrogen atmosphere. Under the light of 500 lux, the water bath was heated to 70° C. for reflux reaction for 2 h. The flask was transferred to an ice-water bath to terminate the reaction, purged with nitrogen, and the tail gas was absorbed with lye. The solvent chloroform and excess thionyl chloride were recovered by distillation, the product was washed with saturated sodium bicarbonate solution until neutral, the organic phase was dried, filtered, and purified by rectification under reduced pressure to collect 3-(2-chloroethyl)-1 , 13.84 g of 5-dichloropentane.

[0093] (2) Alkylation reaction to prepare 4-(5-chloro-3-(2-chloroethyl)pentyl)-1,1’-biphenyl

[00...

Embodiment 2～7

[0103] The preparation method is the same as in Example 1, the main parameter values ​​of the reaction process are shown in Table 1, and the raw materials and product structure are shown in Table 2:

[0104] Table 1

[0105]

[0106]

[0107] Table 2

[0108]

Embodiment 8

[0110] Using Example 1 to prepare the ring-opening polymerization of lactone derivatives to prepare liquid crystal polymers:

[0111]

[0112] In the reactor connected with nitrogen pipeline, add 28g (0.1mol) of 3-biphenylethyl-valerolactone, toluene 150g, pentafluorophenol 50g, initiator n-butanol 0.106g, catalyst trifluoromethanesulfonic acid 0.0056g (200ppm), replace the air with nitrogen to remove the air in the kettle, fill it with nitrogen until the pressure is 0.1Mpa(G), start stirring and fully dissolve, set the speed at 300rpm, gradually raise the reaction temperature to 100°C, stop the reaction after 4 hours of reaction, Lower the temperature of the system to 60°C, collect the product into a flask, add 100g of ethanol, place the flask in a cold water bath at 10°C to fully precipitate the polymer, filter and wash it, and dry it under vacuum at 60°C to obtain 26.37g of liquid crystal polymer powder. Sample GPC test Mn is 17223 (see image 3 ), the PDI is 1.14, and ...

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Abstract

The invention discloses a mesogen-containing lactone aromatic derivative and a preparation method thereof, as well as a side-chain type liquid crystal polymer prepared from the mesogen-containing lactone aromatic derivative as a polymerization monomer and its preparation Methods and applications. The present invention first adopts the organic synthesis method to prepare mesogen-containing lactone derivatives, and then uses the ring-opening polymerization method to prepare side-chain liquid crystal polymers. The reaction steps are simple, the reaction conditions are mild, and the initiator and polymerization monomer can be controlled. Synthesize the specified molecular weight polymer with the feed ratio. The prepared side chain type liquid crystal polymer meets the processing requirements of conventional methods such as injection molding, molding, extrusion and coating. It can be used in fields such as display, optical recording, chromatographic separation, phase change energy storage, and biological tissue restoration.

Description

technical field [0001] The invention belongs to the technical field of liquid crystal polymers, and relates to a mesogen-containing lactone aromatic derivative and its preparation process, and a side-chain type polymer prepared from the mesogen-containing lactone aromatic derivative as a polymerization monomer. Liquid crystal polymer and its preparation method and application. Background technique [0002] Liquid crystal polymers are polymers that can exist in a liquid crystal state under certain conditions. Compared with polymer compounds, they have molecular orientation and position sequences unique to liquid crystal phases; compared with small molecule liquid crystal compounds, they have high relative Molecular mass and characteristics of polymeric compounds. At present, the flexible main chains of side-chain liquid crystal polymers mainly include polyether, poly(meth)acrylate, and polysiloxane. Its synthesis method is usually the following two ways: [0003] 1) Synthe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D309/30C07D313/04C07D313/18C07D313/00C08G63/08C08G63/87C09K19/38
CPCC07D309/30C07D313/00C07D313/04C07D313/18C08G63/08C08G63/87C09K19/3838
Inventor 孙一峰李旭峰陈海波
Owner WANHUA CHEM GRP CO LTD
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