Ring aliphatic carbonate monomer, polymer and preparation method thereof

A technology of family carbonates and cyclic fats, applied in the field of cyclic aliphatic carbonate monomers, their polymers and their preparation, can solve the problems of many reaction steps, complex synthetic routes, and low yields

Inactive Publication Date: 2008-06-18
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

However, the biggest shortcoming of this method is that the yield is too low, causing the molar content of amino groups introduced on the polymer to hardly exceed 10% (Barrera D.A., Zylstra E., Lansbury P.T., Langer R.Synthesis and RGD peptide modification of a new biodegradable copolymer : poly(lactic acid-co-lysine) J.Am.Chem.Soc.1993; 115:11010)
Japan's Endo etc. have reported three structurally similar six-membered cyclic aminocarbonates (Matsuo J., Aoki K., Sanda F., Endo T.Substituent Effect on the Anionic Equilibrium Polymerization of Six-Membered Cyclic Carbonates.Macromolecules 1998; 31: 4432-4438), but their synthetic routes are more complicated and there are more reaction steps

Method used

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  • Ring aliphatic carbonate monomer, polymer and preparation method thereof
  • Ring aliphatic carbonate monomer, polymer and preparation method thereof
  • Ring aliphatic carbonate monomer, polymer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1: the synthesis of 2-benzyloxyamido-1,3-propanediol

[0028]Take 10g (0.11mol) of 2-amino-1,3-propanediol and dissolve it in 250ml of 10% sodium carbonate aqueous solution, then add 125ml of 1,4-dioxane, stir and mix well, place in an ice-water bath Under certain conditions, slowly add 15.7ml (0.11mol) of benzyl chloroformate with a constant pressure dropping funnel, react at room temperature for 8 hours, add 50ml of distilled water to dilute, then extract three times with ethyl acetate, and dry the organic layer with anhydrous magnesium sulfate , concentrated by rotary evaporation, and recrystallized from ethyl acetate to obtain 20 g of 2-benzyloxyamido-1,3-propanediol with a yield of 80%.

Embodiment 2

[0029] Embodiment 2: the synthesis of 2-benzyloxyamido-1,3-propanediol

[0030] Take 10g (0.11mol) of 2-amino-1,3-propanediol and dissolve it in 250ml of 10% sodium carbonate aqueous solution, then add 250ml of 1,4-dioxane, stir and mix well, and place in an ice-water bath Under certain conditions, slowly add 31.4ml (0.22mol) of benzyl chloroformate with a constant pressure dropping funnel, react at room temperature for 8 hours, add 50ml of distilled water to dilute, then extract three times with ethyl acetate, and dry the organic layer with anhydrous magnesium sulfate , concentrated by rotary evaporation, and recrystallized from ethyl acetate to obtain 20.8 g of 2-benzyloxyamido-1,3-propanediol with a yield of 84%.

Embodiment 3

[0031] Example 3: Synthesis of 2-methyl-2-benzyloxyamido-1,3-propanediol

[0032] Take 10g (0.095mol) of 2-methyl-2-amino-1,3-propanediol and dissolve it in 250ml of 10% sodium carbonate aqueous solution, then add 200ml of 1,4-dioxane, stir and mix well , under the condition of an ice-water bath, slowly add 21ml (0.14mol) benzyl chloroformate with a constant pressure dropping funnel, after reacting at room temperature for 8 hours, add 50ml of distilled water to dilute, then extract three times with ethyl acetate, and the organic layer is washed with anhydrous After drying over magnesium sulfate and concentrating by rotary evaporation, recrystallized from ethyl acetate to obtain 17.7 g of 2-methyl-2-benzyloxyamido-1,3-propanediol with a yield of 78%.

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Abstract

The invention provides a cyclic aliphatic carbonate monomer including 2'-benzyloxygenamide trimethylene carbonate and 2-methyl-2-benzyloxygenamide trimethylene carbonate and the polymer and the preparation method thereof. The raw material for the preparation of the two monomers is 2-amino-1,3-propanediol and 2-methyl-2-amino-1,3-propanediol, the amino group is protected, and the hydroxyl group at two ends and ethyl cacodylic acid chloroformate react to produce the monomer. The polymer with the amino at the protective side is obtained by the homopolymerization of the monomer or the copolymerization of the monomer and the aliphatic cyclic ester, and then the polymer with the side amino is obtained after escaping the protection of the polymer. The functional side amino of the polymer can be loaded with the drug molecules and the bioactive peptide by the covalent bond and the ionic bond. Thereby the invention can be applied in the fields of the drug controlled release, the gene therapy and the tissue engineering.

Description

technical field [0001] The invention relates to a cycloaliphatic carbonate monomer, its polymer and a preparation method, and belongs to the field of biomedical 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 can be gradually degraded into small molecular products through hydrolysis or enzymolysis in the body, and finally excreted from the body through normal physiological metabolic processes. Research hotspots and key points in the field of medical polymers. It has been widely used in the fields of surgical sutures, artificial skin, artificial blood vessels, bone fixation and repair, and drug controlled release. At present, the biodegradable synthetic polymers that are mainly researched and applied mainly include aliphatic polyesters, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D319/06C08G64/02C08G64/30C08G63/64
Inventor 景遐斌胡秀丽陈学思谢志刚黄宇彬郑勇辉
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
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