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Main chain type biodegradable liquid crystal polymer and preparation method thereof

A liquid crystal polymer, biodegradable technology, applied in the direction of liquid crystal materials, chemical instruments and methods, etc., to achieve the effect of improving biocompatibility, broadening the scope of application, and good liquid crystal performance

Active Publication Date: 2020-02-28
杨立群
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Introducing components with liquid crystal properties and biological activity into the chain structure of biodegradable polymers makes the material have the dual excellent properties of both biodegradable polymers and liquid crystal compounds, which not only improves its biocompatibility , and can also improve its ability to respond to the outside world, and at the same time further improve the degradation performance and mechanical properties of the material; at present, there are few research reports on biodegradable liquid crystals at home and abroad

Method used

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  • Main chain type biodegradable liquid crystal polymer and preparation method thereof
  • Main chain type biodegradable liquid crystal polymer and preparation method thereof
  • Main chain type biodegradable liquid crystal polymer and preparation method thereof

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preparation example Construction

[0069] 1. Preparation of end group protected alkanoic acid

[0070] 1.1. Dissolve hydroxy-terminated alkanoic acid or terminal amino acid in a reactor filled with dichloromethane and triethylamine solution, wherein the molar ratio of hydroxy-terminated alkanoic acid or terminal amino acid to triethylamine is 1: (1~10) ;

[0071] 1.2. Under the cooling condition of ice-water bath, slowly add the dichloromethane solution of triphenylchloromethane dropwise under stirring, the amount of triphenylchloromethane added is the molar ratio of terminal hydroxy alkanoic acid or terminal amino acid 1: (1~10 ) times;

[0072] 1.3. After dropping, react at room temperature for 6-12 hours;

[0073] 1.4, sequentially water, 1mol L -1 Wash with hydrochloric acid, saturated sodium bicarbonate solution, and saturated brine, dry over anhydrous sodium sulfate, concentrate to dryness, and recrystallize with petroleum ether to obtain terminal-protected alkanoic acid.

[0074] 2. Preparation of te...

Embodiment 1

[0112] In this embodiment, the main chain type biodegradable liquid crystal polymer and its preparation method are as follows:

[0113] (1) Add 18g (200mmol) of 3-hydroxypropionic acid in dichloromethane (300mL) and 83mL (600mmol) of triethylamine into the reaction flask, cool in an ice-water bath, and slowly add 55.8g of triphenylchloromethane dropwise under stirring (200 mmol) in dichloromethane (200 mL). After dropping, react at room temperature for 8h. Sequentially water, 1mol L -1 Wash with hydrochloric acid, saturated sodium bicarbonate solution, and saturated brine, dry over anhydrous sodium sulfate, concentrate to dryness, and recrystallize with petroleum ether to obtain white end-group-protected propionic acid. Yield: 73%, melting point: 163-165°C.

[0114] (2) Add a solution of 16.6g (50mmol) of end-protected propionic acid in dichloromethane (300mL) and 80mL of dimethylformamide (DMF), cool in an ice-water bath, and slowly add 16.9mL of oxalyl chloride dropwise u...

Embodiment 2

[0130] In this embodiment, the main chain type biodegradable liquid crystal polymer and its preparation method are as follows:

[0131] (1) Add 13.2g (100mmol) of 6-hydroxycaproic acid in dichloromethane (300mL) and 55mL (400mmol) of triethylamine into the reaction flask, cool in an ice-water bath, slowly add 55.8% triphenylchloromethane dropwise under stirring g (200 mmol) in dichloromethane (200 mL). After dropping, react at room temperature for 8h. Sequentially water, 1mol L -1 Wash with hydrochloric acid, saturated sodium bicarbonate solution, and saturated brine, dry over anhydrous sodium sulfate, concentrate to dryness, and recrystallize with petroleum ether to obtain white end-group-protected caproic acid. Yield: 62%, melting point: 117-119°C.

[0132] (2) Add a solution of 18.7g (50mmol) of end-protected hexanoic acid in dichloromethane (300mL) and 80mL of methylformamide (DMF), cool in an ice-water bath, slowly add 16.9mL of oxalyl chloride dropwise under stirring ...

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Abstract

The invention belongs to the technical field of biodegradable medical polymer materials, and particularly relates to a main chain type biodegradable liquid crystal polymer and a preparation method thereof. Natural products such as cholesterin, diosgenin, menthol, isosorbide and the like are used as liquid crystal nucleuses; a hydroxyl-terminated alkanoic acid or an amino-terminated acid is used asa flexible spacer to prepare a liquid crystal intermediate; ring opening polymerization reaction on one or a mixture of two or more than two of following monomers or derivatives from trimethylene carbonate, caprolactone, lactide, glycolide, p-dioxanone, propiolactone, butyrolactone, octolactone, caprolactam, morpholine-2, 3-diketone, and a dianhydride are initiated by taking the liquid crystal intermediate as an initiator, so as to obtain the main chain type biodegradable liquid crystal polymer. The main chain type biodegradable liquid crystal polymer provided by the invention has good liquidcrystal performance, is easy to orientate to form an ordered structure, not only generates response to the outside factors of temperature, pH, stress, electric field, magnetic field and the like, butalso has good biocompatibility and degradation performance.

Description

technical field [0001] The invention belongs to the technical field of biodegradable medical polymer materials, in particular to a main chain type biodegradable liquid crystal polymer and a preparation method thereof. Background technique [0002] Biodegradable polymer materials have a wide range of application values ​​in many biomedical fields such as drug carriers, tissue engineering, and surgery, and their research has attracted more and more attention. By modifying their structures, such as introducing functional Groups, etc., can further improve the degradation performance, biocompatibility and surface properties of such polymers, so as to better adapt to the adhesion and growth of cells or tissues and organs, and make the polymers have controllable molecular structures, Mechanical properties and degradation properties. [0003] Liquid crystal materials can self-assemble into a variety of ordered structures, and can respond to changes in external conditions such as te...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G64/30C08G63/64C09K19/38
CPCC08G63/64C08G64/30C08G64/305C09K19/3804C09K19/3809
Inventor 杨立群胡建设陈超先陈思文
Owner 杨立群
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