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Preparation method of multi-sulfydryl hyperbranched polythioether based on alpha lipoic acid

A technology of lipoic acid and polysulfide, applied in the field of hyperbranched polymer preparation, achieving the effects of low cost, easy availability of raw materials, and good thermal stability

Active Publication Date: 2016-12-07
GUILIN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, the use of lipoic acid as a raw material to synthesize various biocompatible polymers has been reported, but the use of lipoic acid as a raw material to prepare multimercapto hyperbranched polythioethers is still rarely reported.

Method used

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  • Preparation method of multi-sulfydryl hyperbranched polythioether based on alpha lipoic acid
  • Preparation method of multi-sulfydryl hyperbranched polythioether based on alpha lipoic acid
  • Preparation method of multi-sulfydryl hyperbranched polythioether based on alpha lipoic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] (1) Add 1 part by weight of lipoic acid and 0.2 part by weight of propynyl alcohol to 20 parts by weight of tetrahydrofuran, stir for 5 minutes, then add 1.2 parts by weight of N,N'-dicyclohexylcarbodiimide React with 0.5 parts by weight of 4-dimethylaminopyridine at 25° C. for 12 hours to obtain a product containing both disulfide bonds and triple bonds.

[0019] (2) 1 weight part of the product containing disulfide bonds and triple bonds prepared in step (1) is dissolved in 100 parts by weight of tetrahydrofuran, and then 3.6 parts by weight of dithiothreitol and 100 parts by weight of water are added After reacting at 20°C for 8 hours, a product containing both sulfhydryl and triple bonds was obtained.

[0020] (3) Dissolve 1 part by weight of the product containing both mercapto groups and triple bonds prepared in step (2) in 3 parts by weight of N,N-dimethylformamide, and then add 0.02 parts by weight of 2-hydroxy- After 4'-(2-hydroxyethoxy)-2-methylpropiophenone,...

Embodiment 2

[0022] (1) Add 1 part by weight of lipoic acid and 0.1 part by weight of propynyl alcohol to 5 parts by weight of tetrahydrofuran, stir for 5 minutes, then add 1 part by weight of N,N'-dicyclohexylcarbodiimide After reacting with 0.2 parts by weight of 4-dimethylaminopyridine at 20° C. for 3 hours, a product containing both disulfide bonds and triple bonds was obtained.

[0023] (2) The product containing disulfide bond and triple bond that 1 weight part of step (1) is prepared is dissolved in 5 weight parts of tetrahydrofuran, then add 2 weight parts of dithiothreitol and 5 weight parts of water After reacting at 25°C for 24 hours, a product containing both sulfhydryl and triple bonds was obtained.

[0024] (3) Dissolve 1 part by weight of the product containing both mercapto groups and triple bonds prepared in step (2) in 0.5 parts by weight of N,N-dimethylformamide, and then add 0.03 parts by weight of 2-hydroxy- After 2-methyl-1-phenylacetone, it was irradiated under a 50...

Embodiment 3

[0026] (1) Add 1 part by weight of lipoic acid and 0.3 parts by weight of 3-butyn-1-ol to 100 parts by weight of tetrahydrofuran, stir for 5 minutes, then add 1.3 parts by weight of N,N'-bicyclo Hexylcarbodiimide and 0.45 parts by weight of 4-dimethylaminopyridine were reacted at 10° C. for 24 hours to obtain a product containing both disulfide bonds and triple bonds.

[0027] (2) 1 weight part of the product containing disulfide bonds and triple bonds prepared in step (1) is dissolved in 20 weight parts of tetrahydrofuran, and then 5 weight parts of cysteine ​​and 40 weight parts of water are added After reacting at 10°C for 12 hours, a product containing both mercapto and triple bonds was obtained.

[0028] (3) Dissolve 1 part by weight of the product containing both mercapto groups and triple bonds prepared in step (2) in 1.5 parts by weight of N,N-dimethylformamide, and then add 0.02 parts by weight of 2-dimethylformamide After amino-2-benzyl-1-[4-(4-morpholinyl) phenyl]-...

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Abstract

The invention discloses a preparation method of multi-sulfydryl hyperbranched polythioether based on alpha lipoic acid. The preparation method comprises the steps of adding the alpha lipoic acid and a reagent containing triple bond and hydroxyl into tetrahydrofuran, stirring 5 minutes, then adding N,N'-dicyclohexyl carbodiimide and 4-dimethyl amino pyridine, reacting for 3-24 hours in a temperature of 10-25 DEG C to obtain a product containing disulfide bond and triple bond, then dissolving into tetrahydrofuran, adding a reducing agent and water, reacting for 5-24 hours in a temperature of 10-25 DEG C to obtain a product containing sulfydryl and triple bond, dissolving the prepared product containing the sulfydryl and the triple bond into N,N'-dimethyl formamide, then adding a photoinitiator and exposing in an ultraviolet lamp of 500-2000W for 5-60 minutes to carry out thiol-yne click chemical reaction to obtain the multi-sulfydryl hyperbranched polythioether based on the alpha lipoic acid. As a preparation process is simple and the raw materials are easy to obtain, the preparation method is low in cost and suitable for large-scale popularization.

Description

technical field [0001] The invention belongs to the technical field of hyperbranched polymer preparation, in particular to a preparation method of lipoic acid-based polymercapto hyperbranched polysulfide. Background technique [0002] Hyperbranched polymers can not only be synthesized by a simple one-step reaction, but also have dendrimer-like properties such as containing a large number of end groups, no entanglement between molecules, not easy to crystallize, low viscosity, good solubility and reactivity etc., and thus have been widely used in many fields. At present, there have been many reports on the synthesis and application of hyperbranched polymers, but there are few research reports on hyperbranched polysulfides with polymercapto groups. As an important antioxidant in the human body, lipoic acid has good biocompatibility and pharmaceutical activity. So far, the use of lipoic acid as a raw material to synthesize various biocompatible polymers has been reported, but...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G83/00
CPCC08G83/005
Inventor 周立黄博吴佳
Owner GUILIN UNIVERSITY OF TECHNOLOGY
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