Aniline oligomer, its aliphatic polyester copolymer and their prepn

A technology of aliphatic polyesters and oligomers, applied in condensation/addition reactions to prepare amino compounds, organic chemistry, etc., can solve non-degradable problems, achieve convenient processing and utilization, good biocompatibility, and good bioavailability degradability effect

Inactive Publication Date: 2007-01-03
CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

If polyaniline and other electroactive polymers are used in the body for a long time, they can induce adverse reactions of joint inflammation. Since they are...

Method used

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  • Aniline oligomer, its aliphatic polyester copolymer and their prepn
  • Aniline oligomer, its aliphatic polyester copolymer and their prepn
  • Aniline oligomer, its aliphatic polyester copolymer and their prepn

Examples

Experimental program
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Effect test

Embodiment 1

[0059] Embodiment 1: the synthesis of the aniline dimer of terminal amino protection

[0060] In a 500mL three-necked flask equipped with mechanical stirring, nitrogen inlet, and nitrogen outlet, add N-phenyl-1,4-p-phenylenediamine 9.21g (0.05mol), succinic anhydride 5.00g (0.05mol), Dichloromethane 300mL, while stirring. As the reaction proceeded, a gray precipitate was produced. After the reaction was completed, it was filtered, and the obtained precipitate was washed with ether until the filtrate was colorless. The sample was dried in a vacuum oven for 12 hours to obtain the amino-terminated aniline dimer with a yield of 84.5%.

Embodiment 2

[0061] Example 2: Synthesis of aniline tetramers with one carboxyl group and one amino group at the end

[0062] 2.85g (0.01mol) of aniline dimer and 3.5g (0.01mol) of amino-terminated dimer are dissolved in the mixed solution (comprising 100mlDMF, 15ml distilled water, 15ml concentrated hydrochloric acid), cooled to below zero, and then The hydrochloric acid solution of ammonium persulfate (2.28g dissolved in 50ml 1M hydrochloric acid) was slowly added to the above solution through the dropping funnel, while stirring rapidly, the ice salt kept the reaction below zero, after the dropwise addition was completed, the reaction was continued for 2h, and then the The solution was poured into 700ml of distilled water and filtered. Dissolve the obtained precipitate in 300ml of 1M ammonia water, add a hydration trap and stir for reduction overnight, then add an appropriate amount of 1M hydrochloric acid to adjust the pH to 2-3, filter, and vacuum dry the precipitate at 35°C for 48 hou...

Embodiment 3

[0063] Embodiment 3: the synthesis of dicarboxy-terminated aniline pentamer

[0064] Dissolve 2.85 g (0.01 mol) of amino-terminated aniline dimer and 0.54 g (0.005 mol) of p-phenylenediamine in 15 mL of DMF. Add 60 mL of pre-cooled mixed solution (including 30 mL of DMF, 25 mL of distilled water, and 5 mL of concentrated hydrochloric acid), then slowly add a hydrochloric acid solution of ammonium persulfate (2.28 g in 50 mL of 1 mol / L hydrochloric acid) into the above solution through a dropping funnel, Stir rapidly at the same time, after the dropwise addition is completed, continue to react for 1 h, then pour the solution into 300 mL of distilled water and filter. Dissolve the obtained precipitate in 300mL of 1mol / L ammonia water, add hydrazine hydrate and stir for reduction overnight, then add an appropriate amount of 1mol / L hydrochloric acid to adjust the pH to 2-3, filter, and vacuum-dry the precipitate at 45°C for 48h . The obtained 3.0g sample was dissolved in 15mL DM...

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Abstract

The present invention provides aniline oligomers, their aliphatic polyester copolymer and their preparation. Two kinds of aniline oligomers are first synthesized with N-phenyl-1, 4-p-phenylene diamine as material, and then copolymerized with aliphatic polyester to obtain electrically active biodegradable polymers. During the preparation, N-phenyl-1, 4-p-phenylene diamine has its end amido group protected with butanedioic anhydride and is then reacted with end amido aniline dimer and phenylene diamine to obtain aniline tetramer with one end carboxyl group and one end amino group and aniline pentamer with two end carboxyl groups; and the aniline oligomers are finally polycondensated with double hydroxyl group terminated aliphatic polyester to obtain the copolymers containing electrically active aniline oligomer block. The copolymers possess the advantages of both aniline oligomer and aliphatic polyester, and is used as biomedicine material mainly.

Description

technical field [0001] The invention belongs to the field of biomedical polymer materials, and relates to an aniline oligomer, its copolymer with aliphatic polyester and a preparation method. Background technique [0002] In recent decades, with the rapid development of polymer science and the rapid development of modern pharmacy, biology and engineering, the research on biomedical polymer materials has developed rapidly. Among them, biodegradable polymer materials have been widely used in the fields of surgical sutures, artificial skin, artificial blood vessels, bone fixation and repair, and controlled release of drugs because they do not require secondary surgery to remove after implantation. Biodegradable synthetic polymers mainly include aliphatic polyesters, polyamino acids, polyphosphates, polyanhydrides, polyorthoesters, polycarbonates, and the like. Aliphatic polyesters, such as polylactide (PLA), polyglycolide (PGA), polyε-caprolactone (PCL), have low immunogenicit...

Claims

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Application Information

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IPC IPC(8): C07C211/54C07C209/60C08G73/02C08G63/685C08G63/78
Inventor 陈学思黄利红胡军郎乐王献红危岩景遐斌
Owner CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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