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Triple-bond pendant-group aliphatic poly (ester-carbonic ester) and preparation method thereof

An aliphatic and carbonate technology, which is applied in the preparation method of peptides, chemical instruments and methods, and pharmaceutical formulations, can solve the problems of complex synthesis process and high cost, and achieve the effect of high reactivity

Inactive Publication Date: 2011-11-23
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, the synthesis process is complicated and the cost is high

Method used

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  • Triple-bond pendant-group aliphatic poly (ester-carbonic ester) and preparation method thereof
  • Triple-bond pendant-group aliphatic poly (ester-carbonic ester) and preparation method thereof
  • Triple-bond pendant-group aliphatic poly (ester-carbonic ester) and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1: Synthesis of 2-methyl-2-propargyloxycarbonyl-1,3-propanediol

[0027] 9.00 g of 2,2-dimethylolpropionic acid and 4.30 g of potassium hydroxide were dissolved in 50 ml of N,N-dimethylformamide. Stir vigorously for 1 h at 100°C to form potassium salt of 2,2-dimethylolpropionate. Then propargyl bromide was added to the above solution, and stirred vigorously at 100°C for 15h. The solvent was distilled off, the residue was dissolved in 200 ml of ether, washed three times with 50 ml of distilled water, and finally recrystallized with toluene to obtain 8 g of 2-methyl-2-propargyloxycarbonyl-1,3-propanediol with a yield of 70%. Its structure was confirmed by proton NMR spectroscopy.

Embodiment 2

[0028] Embodiment 2: the synthesis of 2-methyl-2-propargyloxycarbonyl trimethylene carbonate (monomer A)

[0029] Dissolve 10 g of 2-methyl-2-propargyloxycarbonyl-1,3-propanediol and 28.5 g of ethyl chloroformate in 600 ml of tetrahydrofuran, and cool in an ice-water bath. Then slowly add 28g of triethylamine into the above solution, and keep the system at about 0°C during the addition. Then react at room temperature for 10h. The precipitate was filtered off, the filtrate was concentrated under reduced pressure, and the residue was recrystallized from tetrahydrofuran and diethyl ether to obtain 9.4 g of white crystals with a yield of 82%. Its structure was confirmed by proton NMR spectroscopy.

Embodiment 3

[0030] Embodiment 3: the synthesis of the copolymer of monomer A and lactic acid

[0031] Under anhydrous and oxygen-free conditions, add 0.2 mole of monomer A and 0.8 mole of lactide monomer into the polymerization reaction bottle, and then add ethyl zinc of 1 / 200 of the total mass of the monomer as an initiator, at 60 The reaction was stirred at ℃ for 2 hours, the product was dissolved in chloroform, precipitated in methanol, filtered, washed, dried in vacuum at 35 ℃ for 24 hours, and the yield was calculated by weighing to obtain a copolymer of monomer A and lactic acid. The weight yield is 89%, and the weight average molecular weight is 1.56×10 4 , molecular weight distribution index 1.15.

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Abstract

The invention relates to triple-bond pendant-group aliphatic poly (ester-carbonic ester) and a preparation method thereof, which belong to the field of biomedical polymer materials. 2-methyl-2-propargyl carbobenzoxygroup trimethylene carbonic ester is used as a triple-bond pendant-group monomer and is copolymerized with cyclic ester monomers, such as lactide, glycolide or epsilon-caprolactone copolymer to obtain the triple-bond pendant-group aliphatic poly (ester-carbonic ester). The polymer has the advantages of aliphatic polyester and carbonic ester and can be biodegraded, and degradation products are nontoxic. Medicines, active small peptides or other bioactive molecules can be connected with the polymer by using the reactivity of the triple-bond pendant group in order to improve the biocompatibility and the biological activity of the polymer, and therefore, the triple-bond pendant-group aliphatic poly (ester-carbonic ester) can be practically applied to the fields of controlled drug release, macromolecule prodrugs, organizational projects, and the like.

Description

technical field [0001] The invention relates to aliphatic poly(ester-carbonate) with triple bond side groups and a preparation method thereof, belonging to the field of biomedical polymer materials. 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 immuno...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G63/64C08G63/664C08G65/48A61K47/34C07K1/14A61L27/18A61L31/06
Inventor 景遐斌胡秀丽陈学思谢志刚吕常海石全庄秀丽
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI