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Cyclic aliphatic acid ester carbonate, its polymer, synthesis method and uses thereof

A technology of cyclic aliphatic and aliphatic carbonates, which is applied in the field of biomedical polymer materials, can solve problems such as unsatisfactory biodegradation performance, difficulty in bonding drugs, and limited applications, and achieve low raw material prices and good hydrophilic/hydrophobic properties , high reactivity

Inactive Publication Date: 2006-07-19
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

This series of patents is limited to the homopolymer of this monomer. It is a well-known fact that the biodegradability of homopolymerized aliphatic carbonate in the human body is not ideal, so its application in biomedicine will be limited.
In this patent, secondary hydroxyl groups are obtained after deprotection, and their activity is not high, so it is difficult to further bond drugs, antibodies or other biologically active molecules to the polymer

Method used

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  • Cyclic aliphatic acid ester carbonate, its polymer, synthesis method and uses thereof
  • Cyclic aliphatic acid ester carbonate, its polymer, synthesis method and uses thereof
  • Cyclic aliphatic acid ester carbonate, its polymer, synthesis method and uses thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0030] Example 1: Synthesis of 2-phenyl-5,5-dimethylol-1,3-dioxane

[0031] Dissolve 68g (0.50mol) of pentaerythritol in 500ml of water, add 53g (0.50mol) of benzaldehyde and 2.5ml of concentrated hydrochloric acid, stir vigorously at room temperature for 5h, let it stand for 24h, wash the crude product with distilled water three times, and then successively wash it with sodium carbonate solution Recrystallized from toluene to obtain 87 g (0.39 mol) of 2-phenyl-5,5-dimethylol-1,3-dioxane as white crystals. Yield 78%.

Embodiment 2

[0032] Example 2: Synthesis of 2,2-dimethyl-5,5-dimethylol-1,3-dioxane

[0033] Dissolve 50g (0.36mol) of pentaerythritol and 0.61g (0.0032mol) of p-toluenesulfonic acid in 500ml of acetone, then add 55.4ml (0.36mol) of 2,2-dimethoxypropane, stir at room temperature for 24h, then add 5ml of ammonia water / ethyl acetate solution (50:50). Concentrate under reduced pressure, add 500ml of dichloromethane, extract with water, collect the organic layer, dry over magnesium sulfate, evaporate the solvent to obtain the product white crystals, namely 2,2-dimethyl-5,5-dimethylol-1 , 3-dioxane. Yield 62%.

Embodiment 3

[0034] Example 3: Synthesis of carbonate monomer 9-phenyl-2,4,8,10-tetraoxaspiro[5,5]undecane-3-one

[0035] Dissolve 9.5g (0.042mol) of 2-phenyl-5,5-dimethylol-1,3-dioxane and 8.1ml (0.082mol) of ethyl chloroformate in 400ml of tetrahydrofuran at 0°C Slowly add 12ml (0.086mol) triethylamine, react at room temperature for 2h, filter off the generated triethylamine hydrochloride, concentrate the filtrate under reduced pressure, and recrystallize with tetrahydrofuran / ether to obtain white crystals, namely 9-phenyl- 2,4,8,10-tetraoxaspiro[5,5]undecan-3-one. That 1 See attached for H NMR spectrum figure 1 .

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Abstract

The provided preparation methdo for cyclic aliphatic carbonate comprises: protecting two hydroxyl groups of the pentaerythritol to let another couple of hydroxyl react with ethyl chloroformate; further, ring-opening polymerizing or copolymerizing with aliphatic cyclic ester, removing the protection, and obtaining the product. This cyclic esters is fit to biodegradation without toxin, can connect the drug and active short peptide to improve the polymer bio- compatibility and bio-compatibility, and has wide application.

Description

technical field [0001] The invention relates to an aliphatic carbonate monomer with a side hydroxyl group, a polymer thereof, a synthesis 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 composite pole molecules mainly include aliphatic polyesters, polyamino acids, polyphosphates, polyanhydrides, polyorthoesters, polycarbonates, and the like. Aliphatic polyesters, such as polylactide (PLA), polyglycolide (PGA), pol...

Claims

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Application Information

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IPC IPC(8): C08G64/02
Inventor 景遐斌谢志刚陈学思胡秀丽吕长海关会立
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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