Amino acid base biodegradable 2-expoxy compound and preparation method thereof

An amino acid-based, diepoxy-based technology, applied in organic chemistry, bulk chemical production, etc., can solve problems such as lack of biocompatibility and degradability, and achieve good biodegradation, biocompatibility, and high storage stability , The preparation method is simple and efficient

Active Publication Date: 2013-12-04
SHANGHAI LANGYI FUNCTIONAL MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although the diepoxides provided by the above patents have certain advantages in many aspects, they are relatively deficient in terms of biocompatibility and degradability.

Method used

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  • Amino acid base biodegradable 2-expoxy compound and preparation method thereof
  • Amino acid base biodegradable 2-expoxy compound and preparation method thereof
  • Amino acid base biodegradable 2-expoxy compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] 1. Take a round-bottomed flask with a magnet and place it in an ice bath, add 1.5g of glycine and 30mL of deionized water in sequence, and then add 30mL of 1mol / L sodium bicarbonate aqueous solution; weigh 7.28g of di-tert-butyl dicarbonate, After dissolving with 35mL of tetrahydrofuran, it was slowly added to a round bottom flask under stirring, and the mixture was reacted at room temperature for 24 hours. After the reaction was completed, it was repeatedly extracted with diethyl ether, and the obtained supernatant was dried with a large amount of anhydrous sodium sulfate, and then filtered with a G4 sand core funnel, and the filtrate was dried to obtain the product tert-butoxycarbonyl-protected amino group glycine.

[0028] 2. Dissolve 1.75g ​​of tert-butoxycarbonyl-protected amino glycine and 1.34g of cinnamyl alcohol in dichloromethane, and then add 9.55g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiethylene After the reaction of amine hydrochloride and 1.22g of 4-dim...

Embodiment 2

[0034] 1. Take a round-bottomed flask with a magnet and place it in an ice bath, add 1.78g of alanine and 30mL of deionized water in sequence, and then add 30mL of 1mol / L sodium bicarbonate aqueous solution; weigh 7.28g of di-tert-butyl dicarbonate After dissolving the ester with 35mL of tetrahydrofuran, it was slowly added to the round bottom flask under stirring, and the mixture was reacted at room temperature for 24 hours. After the reaction was completed, it was repeatedly extracted with diethyl ether, and the obtained supernatant was dried with a large amount of anhydrous sodium sulfate, and then filtered with a G4 sand core funnel, and the filtrate was dried to obtain the product tert-butoxycarbonyl-protected amino-alanine.

[0035] 2. Dissolve 1.89g of alanine and 1.34g of cinnamyl alcohol in dichloromethane, and then add 9.55g of 1-(3-dimethylaminopropyl)-3-ethyl carbon Diimine hydrochloride and 1.22g of 4-dimethylaminopyridine were washed with water and dried several ...

Embodiment 3

[0041] 1. Take a round-bottomed flask with magnets and place it in an ice bath, add 2.34g of valine and 30mL of deionized water in sequence, and then add 30mL of 1mol / L sodium bicarbonate aqueous solution; weigh 7.28g of di-tert-butyl dicarbonate After dissolving the ester with 35mL of tetrahydrofuran, it was slowly added to the round bottom flask under stirring, and the mixture was reacted at room temperature for 24 hours. After the reaction was completed, it was repeatedly extracted with diethyl ether, and the obtained supernatant was dried with a large amount of anhydrous sodium sulfate, and then filtered with a G4 sand core funnel, and the filtrate was dried to obtain the product valine with tert-butoxycarbonyl-protected amino group.

[0042] 2. Dissolve 2.17g of valine and 1.34g of cinnamyl alcohol in dichloromethane, and then add 9.55g of 1-(3-dimethylaminopropyl)-3-ethyl carbon Diimine hydrochloride and 1.22g of 4-dimethylaminopyridine were washed with water and dried sev...

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Abstract

The invention relates to an amino acid base biodegradable 2-expoxy compound and a preparation method of the amino acid base biodegradable 2-expoxy compound. The method includes the following steps that mixed reaction is performed on amino acid monomers and 2-carbonic acid-2-tert-butyl ester, so that amino acid monomers of tert-butoxycarbonyl group protecting amino are obtained, the amino acid monomers of the tert-butoxycarbonyl group protecting amino and cinnamyl alcohol are dissolved in methylene chloride, a certain quantity of catalysts are added, condensation reaction is performed, tert-butoxycarbonyl group protecting groups are gradually removed, then reaction with terephthalic acid is performed, and finally a product is generated with hydrogen peroxide under the action of the catalysts and namely the novel amino acid base biodegradable 2-expoxy compound is generated. The method for preparing the novel amino acid base biodegradable 2-expoxy compound is simple, has good biodegradability and is good in storage stability of the obtained epoxy compound and is a macromolecule epoxy chain extender which has very good application prospects.

Description

technical field [0001] The invention relates to a diepoxide compound and a preparation method thereof, in particular to an amino acid-based biodegradable diepoxide compound. technical background [0002] As a hydroxyl and carboxyl addition type chain extender, the diepoxy compound will not produce other by-products when it reacts with the terminal carboxyl group, and the reaction product can introduce hydroxyl groups into the side chain of the polymer, which can to a certain extent Improve the hydrophilicity of polymers, and diepoxy compounds have higher reactivity, so they are favored by many researchers. However, most diepoxy compounds have poor degradation performance and biocompatibility, and low storage stability. [0003] The Chinese invention with the patent application number 201110107121.2 provides a diepoxide compound with excellent heat resistance and flame retardancy; the Chinese invention patent with the patent application number 200980145591.9 provides a class...

Claims

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Application Information

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IPC IPC(8): C07D303/16C07D301/12
CPCY02P20/55
Inventor 韩锦东唐晓峰董建廷
Owner SHANGHAI LANGYI FUNCTIONAL MATERIALS
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