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Synthesizing process and use of unsaturation cyclic aliphatic carbonate monomer

A technology of cyclic aliphatic and aliphatic carbonates, applied in the direction of organic chemistry, can solve the problems of high cost and complex synthesis process, and achieve the effects of high polymerization activity, high polymerization conversion rate and high reactivity

Inactive Publication Date: 2011-06-22
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 is complicated and the cost is high

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

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 was confirmed by proton NMR spectroscopy, see attached figure 1 .

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Abstract

The invention relates to a cyclic aliphatic carbonate monomer with a triple bond side group, a preparation method and use thereof. 2-methyl-2-propargyl oxygen carbonyl trimethylene carbonate is synthesized from 2,2-dimethylolpropionic acid. The monomer can be used for ring-opening polymerization or ring-opening copolymerization with aliphatic cyclic ester monomer to obtain the aliphatic polycarbonate with triple bond side group or the copolymers of aliphatic polyester-carbonic ester. The polymers have advantages of the aliphatic polyester and carbonic ester, can be biodegradated. The degradation product is non-toxic. The polymers can be used for biomedical material.

Description

[0001] Synthesis method and application of unsaturated cyclic aliphatic carbonate monomer The present invention relates to a synthesis method and application of unsaturated cyclic aliphatic carbonate monomer and its polymer. 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. Biodegr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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