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Method for preparing annular aliphatic carbonic ester containing cinnamoyloxy group and polymers thereof

A technology of cinnamoyloxymethyltrimethylene carbonate and cinnamoyloxy, which is applied in the field of preparation of cycloaliphatic carbonate and its polymers, can solve the problems of polylactic acid and its copolymers that have not been seen yet, Achieve good biocompatibility and low toxicity

Inactive Publication Date: 2010-05-26
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

So far, there have been no literature and patent reports on polylactic acid and its copolymers with photosensitive groups

Method used

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  • Method for preparing annular aliphatic carbonic ester containing cinnamoyloxy group and polymers thereof
  • Method for preparing annular aliphatic carbonic ester containing cinnamoyloxy group and polymers thereof
  • Method for preparing annular aliphatic carbonic ester containing cinnamoyloxy group and polymers thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Preparation of 2-methyl-2-cinnamoyloxymethyltrimethylene carbonate

[0051] Dissolve 200g of 2,2-dimethylolpropanol in 2L of acetone, then add 0.2g of p-toluenesulfonic acid, stir the above mixture at room temperature for 2d, then add 5g of anhydrous potassium carbonate, stir for 1h and filter, the filtrate is concentrated, evaporated Remove acetone to obtain 256g 2,2-dimethyl-5-methyl-5-hydroxymethyl-1,3-dioxane; take 20g 2,2-dimethyl-5-methyl-5- Dissolve hydroxymethyl-1,3-dioxane and cinnamoyl chloride in 250ml of tetrahydrofuran, slowly add 30ml of triethylamine dropwise under ice-water bath conditions, react at 0°C for 2 hours, then stir at room temperature for 12 hours, filter out the formed The precipitate, the filtrate was concentrated to no solvent, then added 100ml of methanol and 15ml of concentrated hydrochloric acid, stirred at room temperature for 5h, added 150ml of saturated aqueous sodium carbonate solution, extracted three times with ethyl acetate, each ...

Embodiment 2

[0053] Preparation of 2-ethyl-2-cinnamoyloxymethyltrimethylene carbonate

[0054] Dissolve 67g of 2,2-dimethylol butanol in 400ml of acetone, then add 0.5g of p-toluenesulfonic acid, stir the above mixture at room temperature for 20h, then add 1g of anhydrous potassium carbonate, stir for 1h and filter, the filtrate is concentrated, Acetone was evaporated to obtain 68g 2,2-dimethyl-5-ethyl-5-hydroxymethyl-1,3-dioxane; 21g 2,2-dimethyl-5-ethyl-5 -Hydroxymethyl-1,3-dioxane and 15g of cinnamoyl chloride were dissolved in 300ml of tetrahydrofuran, and 30ml of triethylamine was slowly added dropwise in an ice-water bath, reacted at 0°C for 2 hours, then stirred at room temperature for 12 hours, and filtered The generated precipitate was removed, the filtrate was concentrated to no solvent, then 100ml of methanol and 12ml of concentrated hydrochloric acid were added, and after stirring at room temperature for 5h, 150ml of saturated aqueous sodium carbonate solution was added, and ex...

Embodiment 3

[0056] Preparation of carbonate homopolymer

[0057] Under anhydrous and oxygen-free conditions, 1mol 2-methyl-2-cinnamoyloxymethyl trimethylene carbonate was added to the polymerization reaction bottle, and then ethyl zinc of 1 / 200 of the total amount of monomers was added as The initiator was reacted at 110°C for 15 hours, the product was dissolved in chloroform, settled in methanol, filtered, washed, and vacuum-dried at 35°C to constant weight to obtain a carbonate homopolymer.

[0058] Using 2-ethyl-2-cinnamoyloxymethyl trimethylene carbonate as a monomer, the reaction process and conditions are the same as above to obtain a homopolymer of the monomer.

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Abstract

The invention relates to a preparing method of cyclic aliphatic carbonic acid esters containing cinnamoxyl, and polymers thereof, belongs to the biomedicine high-molecular material field. Aliphatic cyclic carbonic acid ester 2-methyl-2-cinnamoxymethyl cyclictrimethy carbonic acid ester and 2-ethyl-2-cinnamoxymethyl cyclictrimethy carbonic acid ester are synthesized from 2, 2-dimethylol optal and 2, 2-dimethylol butanol, further homopolymers of the same, copolymers with aliphatic cyclic ester, block copolymers with carbowax, and block copolymers of random copolymers with aliphatic cyclic esterand carbowax are synthesized. The copolymers contains cinnamoxyl pleurocoxal capable of generating reversible cross bonding reaction. With the biodegradability of the bioavailability, the copolymers can be used as biomedicine materials useful in fields, such as surgicals, medicine controlled releasing, tissue engineering, etc.

Description

technical field [0001] The invention belongs to the field of biomedical macromolecule materials, and relates to a preparation method of cycloaliphatic carbonate containing cinnamoyloxy groups and a polymer thereof. Background technique [0002] Aliphatic polycarbonates are an important class of biodegradable / absorbable polymers. It has good biocompatibility and physical and mechanical properties, which can meet different needs. On the other hand, polycarbonate degrades to generate carbon dioxide and neutral diols, which can avoid the adverse effects caused by polylactic acid, polyglycolic acid and other carboxylic acids produced during the degradation process. Therefore, biodegradable polycarbonate has been more and more widely used in drug controlled release, in vivo implant materials, tissue engineering and so on. Ring-opening polymerization is one of the important polymer synthesis methods. Common synthetic biodegradable polymers, such as polyesters, polyamino acids, p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D319/06C08G64/02C08G64/18C08G64/30C08J5/18C08J7/12
Inventor 景遐斌胡秀丽陈学思谢志刚莫国军黄宇彬庄秀丽
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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