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Preparation method of polymer of lipoic acid compound

A technology for lipoic acids and compounds, which is applied in the field of polymer preparation, can solve the problems of difficult control of configuration and molecular weight, complicated reaction conditions, etc., and achieves the effects of rapid and efficient ring-opening polymerization, simple preparation method and easy preparation.

Active Publication Date: 2021-08-06
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Direct thermal polymerization and photopolymerization mainly use the disulfide bond breakage under the action of heat or light to generate sulfur free radicals, and the sulfur free radicals between different molecules are connected to each other to form bonds again, so as to realize ring-opening polymerization, thermal polymerization and photopolymerization conditions Mild, simple process, fast preparation, high atom utilization, but there are also disadvantages such as difficulty in controlling the configuration and molecular weight, and the need for additional cross-linking agents to quench excess free radicals; the thiol induction method is passed in alkaline solution Sulfide anion triggers disulfide bond ring-opening polymerization chain reaction, the reaction can be completed at room temperature, high conversion rate can be achieved in a short time, and the structure of the polymer can be precisely controlled under specific conditions, but this The method needs to be carried out in a strictly anhydrous and oxygen-free organic solvent, which is not suitable for monomers containing carboxyl groups, and requires the participation of organic bases, mercaptans, and quenchers at the same time, and the reaction conditions are relatively complicated (Architecture-controlled ring-openingpolymerization for dynamic covalentpoly(disulfide)s[J].J.Am.Chem.Soc.,2019,141(43):17075-17080.)

Method used

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  • Preparation method of polymer of lipoic acid compound
  • Preparation method of polymer of lipoic acid compound
  • Preparation method of polymer of lipoic acid compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Solvent-free direct hot melt catalytic polymerization:

[0035]Weigh lipoic acid powder (3g, 0.0145mol) into a clean small flask, heat in an oil bath at 70°C for about 10 minutes until the powder melts, start stirring, then add 20uL 0.725mol / L N-butylbenzyl with a pipette Add the acetone solution of amine hexafluorophosphate to the flask and continue to heat and stir for 5 minutes. The molar ratio of the lipoic acid compound to the catalyst is 4000:4, the heating is stopped, and the liquid is cooled to room temperature, that is, the hot-melt catalytic polymerization process is completed, and the xerogel of the lipoic acid polymer is obtained.

[0036] figure 1 It is a schematic diagram of the lipoic acid polymer image obtained by solvent-free direct hot-melt catalytic polymerization in Example 1, as can be seen from the figure, it is yellow transparent elastic xerogel; figure 2 It is the proton nuclear magnetic resonance spectrum of the lipoic acid polymer xerogel ob...

Embodiment 2~4

[0038] Except changing the mol ratio of lipoic acid added, catalyzer, all the other steps and conditions are identical with embodiment 1, specifically as shown in table 1:

[0039] Table 1

[0040]

Embodiment 5

[0042] Solution-catalyzed polymerization at room temperature: take lipoic acid powder (3g, 0.0145mol) and place it in a clean small flask, add 4.2ml of methylene chloride, the concentration of lipoic acid dissolved in methylene chloride is 3.5mol / L, stir and dissolve, Then use a pipette to add 20uL 0.725mol / L N-butylbenzylamine hexafluorophosphate acetone solution into the flask, continue to stir for 1 minute, the solution viscosity gradually increases, and then take it out and place it in an open polytetrafluoroethylene mold On the condition of room temperature, the solvent was volatilized for 1 hour to obtain xerogel of lipoic acid polymer.

[0043] Figure 4 It is a schematic diagram of the gel image of the lipoic acid polymer obtained by catalytic polymerization at room temperature in Example 5; it can be seen from the figure that it is in the form of a yellow transparent elastic xerogel.

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Abstract

The invention discloses a preparation method of a polymer of a lipoic acid compound. The preparation method is selected from a solvent-free direct hot-melting catalytic polymerization method or a room-temperature solution catalytic polymerization method. The catalyst used in the method is wide in source, easy to prepare and low in price, catalysis methods are diversified, the process is simple, metal ions are not contained, efficient catalysis can be achieved only through a trace amount of catalyst, and practical industrial feasibility is achieved; catalytic polymerization can be carried out under the condition that no solvent is directly heated and melted, and catalytic polymerization can also be carried out in a solution under the room temperature condition; the direct hot melting catalysis method does not need any organic solvent, has the advantages of rapid catalysis process, mild conditions, simple and safe operation, high atom utilization rate and no three wastes, and meets the green chemical requirements; according to the room-temperature solution catalysis method, heating and complex conditions are not needed, and efficient catalytic polymerization under the room-temperature condition can be achieved by adding a trace amount of catalyst into a monomer solution.

Description

technical field [0001] The invention belongs to the technical field of polymer material chemistry, and in particular relates to a preparation method of a polymer of lipoic acid compounds. Background technique [0002] Disulfide bond is a dynamic covalent bond that widely exists in living organisms. It is an important part of the secondary and tertiary structure of proteins and plays an important role in the stability of peptide chain structures and the formation of three-dimensional structures of protein molecules. Due to its relatively low bond energy (251kJ / mol), disulfide bonds have dynamic reversibility similar to supramolecular interactions, enabling the breaking and reconnecting of S-S bonds under external conditions. For cyclic compounds containing disulfide bonds, under certain conditions, the highly dynamic and reversible properties of disulfide bonds make the disulfide bonds break first in the molecule and then reconnect intermolecularly. Ring polymerization has s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G75/06
CPCC08G75/06
Inventor 曲大辉王邦森张琦施晨宇何丹丹
Owner EAST CHINA UNIV OF SCI & TECH
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