Preparation method for polyester with side chain containing dimethyl pyridylamine

A lutidine and side chain technology is applied in the field of preparation of polyesters containing lutidine in side chains, and can solve the problem that hydrophobic drugs and hydrophilic genes cannot be co-transported, and aliphatic polyesters are hydrophilic Insufficient sex and other problems to achieve good gene compounding ability and broaden the effect of biological applications

Active Publication Date: 2020-03-31
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to solve the problem that aliphatic polyesters have insufficient hydrophilicity and cannot jointly transport hydrophobic drugs and hydrophilic genes. A method for preparing polyesters containing DPA in the side chain is disclosed. The preparation process of the method is simple and the reactants Inexpensive and non-polluting, the prepared aliphatic polyester contains post-modification functional groups, which can be used to connect hydrophilic fragments that can be combined to improve its hydrophilicity and gene loading capacity

Method used

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  • Preparation method for polyester with side chain containing dimethyl pyridylamine
  • Preparation method for polyester with side chain containing dimethyl pyridylamine
  • Preparation method for polyester with side chain containing dimethyl pyridylamine

Examples

Experimental program
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Effect test

Embodiment 1

[0022] Taking the monomer B as 1,6-hexanediol as an example to calculate: use a precision balance to accurately weigh 3.588g (0.02mol, 1eq) dimethyl 1,3-acetonedicarboxylate, put it in a 20mL reaction bottle, and then accurately weigh Take 2.363g (0.02mol, 1eq) 1,6-hexanediol, and finally weigh 102mg (3*10 -4 mol, 0.015eq) TBT, and add magnetons, place in a 100°C round table, raise the temperature by 10°C every 20min, until the temperature rises to 150°C, and keep at 150°C for 4h. Stop the reaction, cool to room temperature, add 4-5ml of chloroform to heat and sonicate until dissolved. Add 15mL of methanol in a 20mL centrifuge tube, add 2mL of product each time, centrifuge at 6000r / min for 5min to remove remaining raw materials and oligomers, and the product obtained by centrifugation is dried in a vacuum oven for 24h. NMR characterization as figure 1 shown. Similar polymers can be obtained by expanding diol monomers into a series of aliphatic diols of different lengths, an...

Embodiment 2

[0028] Taking monomer B as 1,6-hexanediol as an example, calculate: use a precision balance to accurately weigh 54mg of polymer (0.008mmol, carbonyl content is 1eq) in a 20mL reaction bottle, and then accurately weigh 36.6mg (0.184mmol, 1eq ) DPA was added to the reaction bottle, and finally 0.076mg (0.09mmol, 0.05eq) PTSA was weighed, and 2mL DMSO was added as the reaction solvent, and a magnet was added, stirred and heated to 100°C, and reacted for 24h. Stop the reaction, settle in ether for 5 times, remove the reaction raw materials and solvent, and the product obtained by the precipitation is dried in a vacuum oven for 24h, and the nuclear magnetic characterization of the polymer containing DPA in the gained side chain is as follows: figure 2 shown.

Embodiment 3

[0030] Taking the monomer B as 1,6 hexanediol as an example to calculate: use a precision balance to accurately weigh 54mg of a polymer containing DPA in the side chain, put it in a 20ml reaction bottle, and then accurately weigh 17mg (0.184mmol) of zinc nitrate, add 1ml of DMSO As the reaction solvent, the reaction was stirred at room temperature for 24h. Stop the reaction, settle in ether for 5 times, remove the reaction raw materials and solvent, and the product obtained by the precipitation is dried in a vacuum oven for 24h, and the nuclear magnetic characterization of the polymer containing DPA-Zn in the gained side chain is as follows: image 3 shown.

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Abstract

The invention belongs to the technical field of polymer science, and provides a preparation method for polyester with a side chain containing dimethyl pyridylamine. The preparation method comprises the following steps: subjecting a 1,3-acetone dicarboxylic acid monomer and a dihydric alcohol monomer to one-step bulk polymerization under the action of a catalyst, namely tetrabutyl titanate so as toobtain a polyester material; after completion of polymerization, subjecting the polyester material to a grafting reaction with DPA under the catalysis of p-toluenesulfonic acid; and carrying out coordination with zinc nitrate so as to obtain the polyester material with the side chain containing DPA-Zn. The preparation method provided by the invention provides a technical reference for synthesizing a novel polyester material and widens the biological application of the polyester material. According to the invention, dimethyl dicarboxylate containing post-modifiable sites is used as a raw material for polymerization with various types of diols to form polyester; and the formed polyester has good gene recombination capability after coordination between DPA and zinc ions, is expected to be applied to entrapment of hydrophobic drugs and co-delivery of genes, and overcomes the defect that traditional polyester can only deliver hydrophobic drugs but not co-deliver genes.

Description

technical field [0001] The invention belongs to the field of polymer science and technology, and relates to a method for preparing a side chain-containing lutidine amine polyester. Background technique [0002] At present, there are many kinds of polymer materials with different properties, so they can be widely used in the repair and replacement of various human tissues, such as ligaments, tendons, skin, blood vessels and other soft and hard tissues of the human body, while biodegradable polymer materials The most widespread medical applications are as carrier materials for drug control systems and short-term implants in vivo. When the long-acting drug with biodegradable polymer material as the carrier is implanted in the body, the carrier does not need to be removed after the drug is released, which increases the curative effect of the drug and greatly reduces the pain of the drug user. and trouble. Under the action of the biological environment, these carrier materials ...

Claims

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Application Information

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IPC IPC(8): C08G63/91C08G63/16C08G63/672A61K47/59
CPCA61K47/593C08G63/16C08G63/672C08G63/916
Inventor 郑玉斌赵雪梅郑楠
Owner DALIAN UNIV OF TECH
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