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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: 2014-07-09
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 into a 100ml three-necked flask (installed with tail gas absorption device), add 2g of L-Phe at 100°C, stir to dissolve it completely , add 1.96ml ethanolamine and 0.0222g p-toluenesulfonic acid, stop the reaction after reacting for 5h, cool to room temperature, add ethyl acetate and collect the precipitated solid. Take the intermediate and dissolve it in 20ml of DMF, add 0.36g of DCC and 0.35ml of acrylic acid under the ice bath to react for 1 hour, remove the ice bath, raise the temperature to room temperature and react for 8 hours, a white solid appears, filter the solid and add distilled water to the solution , a light yellow solid was precipitated, distilled water was added slowly until the solid was no longer precipitated, and the chiral monomer was collected.

[0023] 2. Preparation of chiral gel: Dissolve 0.05g of chiral monomer and 0.95g of NIPAam in 10mL of absolute ethan...

Embodiment 2

[0026] 1. With the step 1 of embodiment 1.

[0027] 2. Preparation of chiral gel: Dissolve 0.10g and 0.90g NIPAam of the prepared chiral monomer in 10mL of absolute ethanol, add crosslinking agent 0.14g MBA, stir well and pass N 2 After 20min, add 0.05g AIBN as initiator, dissolve and fill with N 2 20min, sealed, reacted at 60°C for 6h to obtain chiral gel P(NIPAam-co-AAc-L-EAPhe) (R=0.10), then cut it into small pieces with a φ12mm mold, soaked in distilled water, one The water was changed daily for a week to remove unreacted small molecules and allowed to fully swell in deionized water at room temperature.

[0028] The LCST of the gel 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. With the step 1 of embodiment 1.

[0031] 2. Preparation of chiral gel: Dissolve the prepared chiral monomer 0.15g and 0.85g NIPAam in 10mL absolute ethanol, add cross-linking agent 0.14g MBA, stir well and pass N 2 After 20min, add 0.05g AIBN as initiator, dissolve and fill with N 2 20min, sealed, reacted at 60°C for 6h to obtain chiral gel P(NIPAam-co-AAc-L-EAPhe) (R=0.15), then cut it into small pieces with a φ12mm mold, soaked in distilled water, one The water was changed daily for a week to remove unreacted small molecules and allowed to fully swell in deionized water at room temperature.

[0032] The LCST of the gel 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 branched chains containing L-amino acid groups. The gel shrinks when the temperature rises above a certain critical temperature, and expands when the temperature recovers. At the same time, because the gel contains L-amino acid chiral groups, it has the function of recognizing and adsorbing chiral molecules. It is a kind of Potential chiral resolution materials. Background technique [0002] With the in-depth study of chiral drugs, the development of new chiral preparation technology has received extensive attention. At present, there are three main ways to prepare chiral drugs: extraction from natural products, asymmetric synthesis and resolution of racemates. 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 optical purity of the ...

Claims

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Application Information

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Patent Type & Authority Patents(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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