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Temperature response type chiral polymer hydrosol with branched chain structure

A technology of chiral polymer and branched chain structure, applied in the field of intelligent polymer materials, can solve the problems of slow response speed, influence of gel application, slow response speed of macro gel, etc., and achieve the effect of easy control and convenient use

Inactive Publication Date: 2012-08-08
TIANJIN POLYTECHNIC UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few reports on the use of smart gels as solid-phase extraction agents for chiral separations
[0005] However, traditional macroscopic gels have the disadvantage of slow response speed, because the swelling and shrinkage of traditional gels are determined by the degree of solution diffusion in their own networks.
Too slow response speed has a great impact on gel application

Method used

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  • Temperature response type chiral polymer hydrosol with branched chain structure
  • Temperature response type chiral polymer hydrosol with branched chain structure
  • Temperature response type chiral polymer hydrosol with branched chain structure

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] 1. Preparation of chiral monomer containing L-phenylalanine group: add glacial acetic acid to a 100ml three-necked flask (with exhaust absorption device installed), add 2g L-Phe at 100℃, stir to make it completely dissolved , Add 1.96ml ethanolamine and 0.0222g p-toluenesulfonic acid, stop the reaction after 5h of reaction, cool to room temperature, collect the precipitated solid after adding ethyl acetate. Dissolve this intermediate in 20ml DMF, add 0.36g DCC and 0.35ml acrylic acid under ice bath to react for 1h, then remove the ice bath, raise the temperature to room temperature and react for 8h, white solid appears, the solid is suction filtered and distilled water is added to the solution , A light yellow solid precipitates, slowly add distilled water until the solid no longer precipitates, collect the chiral monomer.

[0023] 2. Preparation of chiral gel: Dissolve the prepared chiral monomer 0.05g and 0.95g NIPAam in 10mL absolute ethanol, add crosslinking agent 0.14...

Embodiment 2

[0026] 1. Same as step 1 of Example 1.

[0027] 2. Preparation of chiral gel: Dissolve the prepared chiral monomer 0.10g and 0.90g NIPAam in 10mL absolute ethanol, add crosslinking agent 0.14g MBA, stir well and pass N 2 Add 0.05g AIBN as initiator after 20min, dissolve and charge with N 2 After 20 minutes, sealed and reacted at 60°C for 6 hours, a chiral gel P (NIPAam-co-AAc-L-EAPhe) (R=0.10) is obtained, and then cut into small pieces with a φ12mm mold, soaked in distilled water, one Change the water every day during the week to remove unreacted small molecules and allow them to fully swell in deionized water at room temperature.

[0028] The gel LCST is 29.4°C. When the temperature is lower than 29.4°C, the gel swells; when the temperature is higher than 29.4°C, the gel shrinks, indicating that the gel has good temperature sensitivity.

Embodiment 3

[0030] 1. Same as step 1 of Example 1.

[0031] 2. Preparation of chiral gel: dissolve the prepared chiral monomer 0.15g and 0.85g NIPAam in 10mL absolute ethanol, add crosslinking agent 0.14g MBA, stir well and pass N 2 Add 0.05g AIBN as initiator after 20min, dissolve and charge with N 2 After 20 minutes, sealed and reacted at 60°C for 6 hours, a chiral gel P (NIPAam-co-AAc-L-EAPhe) (R=0.15) was obtained, and then cut into small pieces with a φ12mm mold, and soaked in distilled water, one Change the water every day during the week to remove unreacted small molecules and allow them to fully swell in deionized water at room temperature.

[0032] The gel LCST is 28.9°C, when the temperature is lower than 28.9°C, the gel swells; when the temperature is higher than 28.9°C, the gel shrinks, indicating that the gel has good temperature sensitivity.

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Abstract

The invention discloses a temperature response type chiral polymer hydrosol with a branched chain structure and a preparation method thereof. The hydrosol consists of chiral monomer M1 containing an L-amino acid group and a flexible branched chain with two to six carbon atoms and alkyl acrylamide M2 with temperature sensitive characteristic, wherein the mass percent M1:M2 of using amounts of the M1 and M2 is equal to 5-25:95-75. The preparation method comprises the following steps of: esterifying by taking the L-amino acid as a raw material; condensing with acrylic acid to prepare the chiral monomer M1; and dissolving M1 and M2 in absolute ethanol under an oxygen-free condition to perform free radical copolymerization reaction to obtain the temperature response type chiral polymer hydrosol. The temperature response type chiral polymer hydrosol has the advantages of simple process, low cost, convenience for industrial promotion and application and the like; the temperature sensitivity and the chiral separation efficiency of the hydrosol can be adjusted by changing the temperature, the rate of charge, the using amount of a cross-linking agent and raw materials and can be used for separation research of a chiral compound.

Description

Technical field [0001] The invention relates to an intelligent polymer material, in particular to a temperature-responsive chiral polymer hydrogel with a branched chain containing L-amino acid groups. The gel shrinks when the temperature rises above a certain critical temperature, and expands and recovers when the temperature recovers. At the same time, because the gel contains the L-amino acid chiral group, it has the function of recognizing and adsorbing chiral molecules. Potential chiral separation of materials. Background technique [0002] With the deepening of research on chiral drugs, the development of new chiral preparation technologies has received extensive attention. At present, there are three main ways to prepare chiral drugs: extraction from natural products, asymmetric synthesis, and racemate resolution. Among them, the extraction method is often limited by natural resources, and it is difficult to obtain a large amount of low-priced drugs; the products obtained...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F220/54C08F220/60C07B57/00B01J20/26B01J20/28
Inventor 陈娇娇傅新蕾马利霞侯蔺桐蒋奕任绒绒张丹丹
Owner TIANJIN POLYTECHNIC UNIV
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