Synthesizing process and use of unsaturation cyclic aliphatic carbonate monomer and its polymer

A technology of cyclic aliphatic and aliphatic carbonates, which is applied in organic chemistry and other fields, and can solve the problems of complex synthesis process and high cost

Inactive Publication Date: 2007-07-18
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Therefore, the synthesis process i

Method used

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  • Synthesizing process and use of unsaturation cyclic aliphatic carbonate monomer and its polymer
  • Synthesizing process and use of unsaturation cyclic aliphatic carbonate monomer and its polymer
  • Synthesizing process and use of unsaturation cyclic aliphatic carbonate monomer and its polymer

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Experimental program
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Embodiment 1

[0058] Example 1: Synthesis of 2-methyl-2-allyloxycarbonyl-1,3-propanediol

[0059] 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

[0060] Example 2: Synthesis of 2-methyl-2-propargyloxycarbonyl-1,3-propanediol

[0061] 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 3

[0062] Embodiment 3: the synthesis of 2-methyl-2-allyloxycarbonyl trimethylene carbonate (monomer A)

[0063] 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%. Its structure is confirmed by proton nuclear magnetic resonance spectrum, see accompanying drawing 1.

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Abstract

This invention involves unsaturated cyclic aliphatic carbonate monomer and polymer synthesis and uses, and is biomedical polymer materials. From 2,2 - dimethylolpropionic acid departing, to synthesize 2-methyl-2-allyl-oxygen carbonyl trimethylene carbonate and 2-methyl-2-propargyl oxygen carbonyl trimethylene carbonate, and then through ring-opening polymerization or aliphatic monomers cycloate monomer opening loop and copolymerization, gain copolymer of aliphatic polycarbonate or aliphatic polyester-carbonate that side group contains double and Triple bond. Such polymer has advantage of both aliphatic polyester and carbonate, is biodegradable, degradation products is non-toxic. Use the functional side group of Double and Triple bond can connect drugs, active peptides or other bioactive elements with the polymer, improving the biocompatibility and biological activity of polymer, which may has real application in controlled-release drug, polymer pro-drug and tissue engineering fields.

Description

[0001] The invention relates to a synthesis method and application of an unsaturated cycloaliphatic carbonate monomer and a polymer thereof. It specifically relates to a cyclic aliphatic carbonate monomer having a double bond and / or triple bond in a side group, a polymer thereof, a preparation method and an application thereof, and belongs 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, poly...

Claims

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Application Information

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IPC IPC(8): C07D319/04C08G64/02C08G64/20C08G64/18
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
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