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Polyethyleneglycol-aliphatic poly (ester-carbonic ester) with allyl lateral group, preparation method thereof and application thereof

A technology of allyloxycarbonyl trimethylene carbonate and polyethylene glycol, which is applied in the field of biomedical polymer materials and can solve problems such as high cost and complicated synthesis process

Inactive Publication Date: 2009-12-02
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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  • Polyethyleneglycol-aliphatic poly (ester-carbonic ester) with allyl lateral group, preparation method thereof and application thereof
  • Polyethyleneglycol-aliphatic poly (ester-carbonic ester) with allyl lateral group, preparation method thereof and application thereof
  • Polyethyleneglycol-aliphatic poly (ester-carbonic ester) with allyl lateral group, preparation method thereof and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0035] Example 1: Synthesis of 2-methyl-2-allyloxycarbonyl-1,3-propanediol

[0036] 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. Propylene bromide was then added to the above solution, and stirred vigorously for 15 h at 100°C. The solvent was evaporated, the residue was dissolved in 200ml of ether, washed three times with 50ml of distilled water, and finally recrystallized with toluene to obtain 7.9g of 2-methyl-2-allyloxycarbonyl-1,3-propanediol with a yield of 68%. Its structure was confirmed by proton NMR spectroscopy.

Embodiment 2

[0037] Embodiment 2: the synthesis of 2-methyl-2-allyloxycarbonyl trimethylene carbonate (monomer A)

[0038] Dissolve 10 g of 2-methyl-2-allyloxycarbonyl-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 9.2 g of white crystals with a yield of 80%.

Embodiment 3

[0039] Example 3: Copolymerization of monomer A with lactic acid in the presence of polyethylene glycol

[0040] Under anhydrous and oxygen-free conditions, use methoxypolyethylene glycol (PEG) with a molecular weight of 5000 as a macromolecular initiator, take monomer A and lactide monomer, and add 1 / 200 of the total mass of the monomer Ethyl zinc was used as an initiator, stirred and reacted at 60°C for 2h, the product was dissolved in chloroform, precipitated with methanol, filtered, washed, and vacuum-dried at 35°C for 24h, to obtain polyethylene glycol, monomer A and lactic acid copolymer. Typical aggregation results are shown in Table 1.

[0041] Table 1. Copolymerization of monomer A with lactic acid in the presence of polyethylene glycol

[0042] serial number

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Abstract

The invention relates to polyethyleneglycol-aliphatic poly (ester-carbonic ester) with allyl lateral group, a preparation method thereof and application thereof, and belongs to the field of biomedical high molecular materials. In the presence of hydroxy terminated polyethyleneglycol, aliphatic cyclic carbonic ester with allyl and cyclic ester monomer are subjected to ring-opening copolymerization to form the polyethyleneglycol-aliphatic poly (ester-carbonic ester) with the allyl lateral group. The polymer is a biparental segmented copolymer, has the advantages of aliphatic polyester and carbonic ester, and is biodegradable; and the degraded product has no toxicity. By using functional lateral group-double bonds and functionalization thereof, medicaments, active short peptides or other molecules with bioactivity can be connected to the polymer to improve the biocompatibility and bioactivity of the polymer; therefore, the polymer can obtain practical application in the fields of medicament controlled release, high molecular prodrug, tissue engineering, and the like.

Description

[0001] technical scope [0002] The invention relates to polyethylene glycol-aliphatic poly(ester-carbonate) with allyl side groups, a preparation method and application thereof, and belongs to the field of biomedical polymer materials. Background technique [0003] 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...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/48C08G63/64C08G63/79A61K47/48A61K47/60
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