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Temperature sensitive type microgel modified by L-amino acid

A microgel and amino acid technology, applied in the field of temperature-sensitive polymer materials, can solve the problems of slow reaction, high substrate requirements, and high product cost, and achieve the effects of stable molecular structure, simple operation, and controllable reaction

Inactive Publication Date: 2012-09-12
TIANJIN POLYTECHNIC UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are roughly three ways to obtain a single chiral substance: ① Extract from natural products. This extraction method has many synthetic steps in the later stage and the cost of the product is high.
Not only that, natural product sources are limited, and low-cost drugs are not available in large quantities
②Asymmetric synthesis, the optical purity of the product obtained by asymmetric chemical synthesis is still not high enough for most applications; biological asymmetric synthesis has high selectivity, mild reaction conditions, but high requirements for substrates, slow reaction, and separation of products Difficult, so it is also subject to certain restrictions in application
[0006] However, there is still little research on smart microgels for chiral resolution.

Method used

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  • Temperature sensitive type microgel modified by L-amino acid
  • Temperature sensitive type microgel modified by L-amino acid
  • Temperature sensitive type microgel modified by L-amino acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023]Dissolve 1.00g of N-isopropylacrylamide (NIPAM) and 0.10g of MBA in 150mL of deionized water and stir until the solution is transparent, then transfer it into a 250mL four-neck flask equipped with a condenser, a constant pressure dropping funnel, a thermometer and a nitrogen inlet . Under low-speed stirring, pass nitrogen gas to remove oxygen for 30 minutes, raise the temperature to 70°C, keep the temperature for 30 minutes, add 5 mL of APS aqueous solution with a mass concentration of 0.5%, and drop it within 5 minutes. After 5 minutes, the system slowly turns milky white. Nitrogen was continuously passed during the reaction. After the reaction, it was naturally cooled to room temperature. Centrifuge the obtained microgel emulsion, redisperse the microgel in deionized water with ultrasonic oscillation, and centrifuge again, and repeat this three times to remove residual monomers and cross-linking agents, etc., and then put it in a freeze dryer Dry in medium temperatur...

Embodiment 2

[0026] Dissolve the chiral monomer AAc-L-Phe 0.05g, 0.95g NIPAM and 0.10gMBA in 150mL of deionized water and stir until the solution is transparent, then transfer it into a 250mL four-phase tank equipped with a condenser, a constant pressure dropping funnel, a thermometer and a nitrogen inlet. mouth flask. Under low-speed stirring, pass nitrogen gas to remove oxygen for 30 minutes, raise the temperature to 70 ° C, keep the temperature for 30 minutes, add 5 mL of APS aqueous solution with a mass concentration of 0.5%, and drop it within 5 minutes. Nitrogen was continuously passed through during the process. After the reaction, it was naturally cooled to room temperature. Centrifuge the obtained microgel emulsion, redisperse the microgel in deionized water with ultrasonic oscillation, and centrifuge again, and repeat this three times to remove residual monomers and cross-linking agents, etc., and then put it in a freeze dryer Dry in medium temperature, take out after 24 hours ...

Embodiment 3

[0029] Dissolve the chiral monomer AAc-L-Phe 0.10g, 0.90g NIPAM and 0.10gMBA in 150mL of deionized water and stir until the solution is transparent, then transfer it into a 250mL four-phase tank equipped with a condenser, a constant pressure dropping funnel, a thermometer and a nitrogen inlet. mouth flask. Under low-speed stirring, pass nitrogen gas to remove oxygen for 30 minutes, raise the temperature to 70 ° C, keep the temperature for 30 minutes, add 5 mL of APS aqueous solution with a mass concentration of 0.5%, and drop it within 5 minutes. Nitrogen was continuously passed through during the process. After the reaction, it was naturally cooled to room temperature. Centrifuge the obtained microgel emulsion, redisperse the microgel in deionized water with ultrasonic oscillation, and centrifuge again, and repeat this three times to remove residual monomers and cross-linking agents, etc., and then put it in a freeze dryer Dry in medium temperature, take out after 24 hours ...

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Abstract

The invention discloses temperature response type chiral high-molecular microgel modified by L-amino acid and a preparation method thereof. The microgel comprises a chiral monomer M1 containing the base group of L-amino acid, alkyl acrylamide M2 with the characteristic of temperature sensitivity and a chemical cross-linking agent of N,N'-methylene-bisacrylamide M3 (MBA), wherein the mass percent of the M1 and the M2 is 0 to 15:100 to 85, and the quantity of the M3 is 10 percent of the total mass of the monomer. According to the preparation method, the L-amino acid is firstly used as a raw material for esterification, then the L-amino acid is condensed with acryloyl chloride so as to prepare the chiral monomer M1, and afterwards the M1, the M2 and the cross-linking agent M3 are copolymerized in different solvents under the condition of no oxygen so as to obtain chiral temperature sensitive type microgel. The method has the advantages that the operation is simple, the reaction is controllable, the cost is low and the like; the method is suitable for large-scale production and application; and the temperature sensibility and the chiral identification characteristic of the microgel can be regulated by changing the component ratio of reactants and the quantity of the cross-linking agent, and the microgel can be used for the separation research of a chiral compound.

Description

technical field [0001] The invention relates to a temperature-sensitive polymer material, in particular to a temperature-sensitive microgel modified by L-amino acid. The size of the microgel is in the range of 200-950nm, and it is temperature sensitive. At the same time, because the microgel contains L-amino acid chiral groups, it has the function of recognizing and adsorbing chiral molecules, and can be used for the resolution of chiral compounds. point. Background technique [0002] Chirality and chiral resolution technology have become the hotspots of current research. With the development of science and technology, the research and development of chiral drugs will become a new direction of new drug research and development. Therefore, with the continuous deepening of the understanding of chiral molecules, the demand for single chiral substances is increasing, and the requirements for their purity are also increasing. There are roughly three methods for obtaining a sing...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F220/54C08F220/58C08F220/60C08F222/38C07B57/00B01J20/29B01J20/30B01D15/38
Inventor 陈娇娇时东新赵云燕丛光明侯蔺桐杜显丽王乐乐
Owner TIANJIN POLYTECHNIC UNIV
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