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Biodegradable water-soluble polycarbonate and method for preparing same

A polycarbonate, water-soluble technology, applied in the field of synthetic chemistry, can solve problems such as unfavorable large-scale production and practical application, cumbersome and other problems, and achieve the effects of high biocompatibility, high material safety, and simple preparation method.

Inactive Publication Date: 2009-09-30
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Relatively speaking, the synthesis of these methods requires protection-deprotection of functional groups, which is cumbersome and unfavorable for large-scale production and practical application.

Method used

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  • Biodegradable water-soluble polycarbonate and method for preparing same

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] Get 0.5mol N-methyldiethanolamine, 0.6mol diethyl carbonate and 0.003mol K 2 CO 3 , added to a 150ml single-necked flask, and refluxed at 100°C for 2 hours. After fractional distillation at 130°C for 5 hours to remove by-products, a dark brown viscous liquid was obtained. The dark brown viscous liquid was washed with 50ml CH 2 Cl 2 Extraction, wash with 30ml saturated brine each time, wash twice, collect the organic phase, then anhydrous Na 2 SO 4 Dry well. Filter the dried product, remove the solvent, and crack under vacuum at 230°C to obtain a yellow solid-liquid mixture, which is then recrystallized in ethyl acetate to obtain white needle-like crystals with a yield of 20-30%. Through mass spectrometry (MS), infrared (IR), and nuclear magnetic (NMR) characterization analysis, it was confirmed that the white crystal was 6,14-dimethyl-1,3,9,11-tetraoxo-6,14-diazo-cyclo Hexadexane-2,10-dione (ie (ADMC) 2 ). MS: M + =291.IR:v=1746cm -1 (C=O). 1 HNMR (CDCl 3 )...

Embodiment 2

[0016] Get 0.5mol N-methyldiethanolamine, 0.55mol diethyl carbonate and 0.002mol K 2 CO 3 Add it to a 150ml single-necked flask, and reflux at 80°C for 4 hours. After fractional distillation at 120°C for 10 hours to remove by-products, a dark brown viscous liquid was obtained. The dark brown viscous liquid was extracted with 50ml of chloroform, washed with 30ml of saturated brine each time, washed twice, the organic phase was collected, and then anhydrous Na 2 SO 4 Dry well. The dried product was filtered, the solvent was removed, and it was cracked in vacuum at 250°C to obtain a yellow solid-liquid mixture, which was then recrystallized in tetrahydrofuran to obtain white needle-like crystals. Carry out characterization analysis by the method identical with embodiment 1, confirm that this white needle-shaped crystal is (ADMC) 2 .

[0017] Take 50mg of dry monomer (ADMC) 2 , 2.5mg Novozym435 and 0.01ml toluene were placed in a 5ml small test tube, sealed with paraffin, a...

Embodiment 3

[0020] Get dry monomer (ADMC) in 50mg embodiment 1 2 , 10 mg Novozym435 and 0.3 ml toluene were placed in a 5 ml small test tube, sealed with paraffin, and reacted at 60° C. for 24 hours. After the reaction, the product was washed with 3ml CH 2 Cl 2 Dissolve, remove most of the solvent by filtration, and then use ether to make it completely precipitate, collect the precipitate, and dry to obtain the final product. The product was proved to be P(ADMC) by infrared and nuclear magnetic analysis.

[0021] The number average molecular weight of the obtained polymer was Mn=1958 g / mol. Polymer Dp = 13.5.

[0022] Embodiment of the invention (ADMC) 2 The preparation method is to use saturated brine to wash the extract, and other washing liquids can also be used, as long as the extract can be washed clean and does not react with the extract; after collecting the organic phase, use anhydrous Na 2 SO 4 For drying, other desiccants can also be used, as long as they can remove the w...

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Abstract

The invention discloses a biodegradable water-soluble polycarbonate and a method for preparing the same. The polycarbonate is poly (dihydroxyl ethyl methylamine carbonate) which is a homopolymer having the number-average molecular weight of between 1,000 and 12,000 and a structural formula being the molecular formula. The method comprises the following steps: using 6,14-dimethyl-1,3,9,11-tetraoxy-6,14-diaza-cyclo-16-oxane-2,10-dione as a monomer and Novozym435 as a catalyst which are added to a reaction container according to a ratio of 1:0.01-0.20:0.1-10 g / g / ml to toluene, sealing the reaction container to react at a temperature of between 60 and 90 DEG C for 12 to 48 hours; and after the reaction, dissolving the reaction product by using a small amount of CH2Cl2 or chloroform or toluene, filtering the product, fully precipitating the product with large amount of poor solvent, collecting and drying the precipitation to obtain the biodegradable water-soluble polycarbonate. The polycarbonate is soluble in water, has small biological toxicity in HeLa and HepG2 cell lines, and has high biocompatibility, simple preparation method and high material security.

Description

technical field [0001] The invention relates to a biodegradable water-soluble polycarbonate and a preparation method thereof, in particular to a poly(dimethylolmethylamine carbonate) and a preparation method thereof, belonging to the field of synthetic chemistry. Background technique [0002] Aliphatic carbonate (APC) materials have good biocompatibility, biodegradability and excellent mechanical properties, and have attracted extensive attention in the fields of environmental protection materials and medical materials. However, because most of them lack active functional groups, their hydrophilicity is poor, and their degradation speed is not fast, which limits their applications. For example, the affinity of these materials on cells or organs in the body is not strong. Therefore, the modification of APC materials has always been a research hotspot. The introduction of suitable functional groups can effectively improve its surface hydrophilicity, drug compounding ability a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G64/02C08G64/30
Inventor 冯俊王华芬卓仁禧
Owner WUHAN UNIV
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