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Process for preparing cyclic esters comprising unsaturated functional groups and polyesters prepared from same

A technology for cyclic esters and copolymers, applied in the field of preparing cyclic esters containing unsaturated functional groups and polyesters prepared therefrom, can solve problems such as suboptimal, large solvent yield and the like

Inactive Publication Date: 2013-03-27
EVONIK DEGUSSA GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this method is limited because the reaction of α-hydroxy acids to form cyclic esters requires large amounts of solvent and the yields are low, so it is not optimal for use in cost-effective or industrial-scale processes

Method used

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  • Process for preparing cyclic esters comprising unsaturated functional groups and polyesters prepared from same
  • Process for preparing cyclic esters comprising unsaturated functional groups and polyesters prepared from same
  • Process for preparing cyclic esters comprising unsaturated functional groups and polyesters prepared from same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0130] Embodiment 1 (hypothetical embodiment)

[0131]Under high vacuum (~0.02 Torr), α-hydroxy acid, 2-hydroxy-4-pentenoic acid (50 g) was polymerized in bulk at 120 °C using 150 μl (0.95 mol%, mol) of sulfuric acid as a polymerization catalyst and last for 2 hours. Zinc oxide, ZnO (1 g) was added as a transesterification catalyst and the desired monomer was distilled off under high vacuum (~0.02 Torr) and high temperature (230°C to 240°C) and collected on a cold trap (on dry ice superior). Optionally, the collected monomer is purified by recrystallization, for example by dissolving into warm diethyl ether followed by cooling on dry ice overnight to recrystallize the monomer).

Embodiment 2

[0133] 0.20 g (1.02 mmol) of diallyl lactide and 1.30 g (9.03 mmol) of lactide were added to the dry flask under a nitrogen atmosphere. The flask was immersed in an oil bath heated at 130°C. After the solid had melted, 15.4 μl (0.20 mmol) of methyl glycolate and 43.8 μl of a 0.247M solution of tin 2-ethylhexanoate in toluene (containing 0.0108 mmol of tin 2-ethylhexanoate) were added. The liquid was stirred at 130°C for 4 hours. After the liquid had cooled to room temperature, the liquid was dissolved in chloroform and precipitated into cold methanol. The resulting precipitate was collected and dried overnight under vacuum at 45°C-50°C. 1.10 g of polymer were obtained, yield: 73.3%. 1 H NMR (in CDCl 3 Medium, 300MHz): 5.7ppm-5.9ppm (b, CH 2 =CH-),5.1ppm-5.3ppm(b,CH 2 =CH-, O=C-CH-O-), 3.75ppm (b, due to the initiator methyl glycolate, CH 3 O-C=O),2.6ppm-2.8ppm(b,CH 2 =CH-CH 2 -), 1.4ppm-1.7ppm (b, CH 3 -).

[0134] The molecular weight by NMR was 13,400 Daltons. Th...

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Abstract

Disclosed herein are processes for preparing cyclic esters comprising unsaturated functional groups. Also disclosed are copolymers prepared from the cyclic esters. The copolymers can be used to form microparticles, polymer micelles, etc., which are useful in drug delivery applications.

Description

[0001] Cross References to Related Applications [0002] This application claims the benefit of priority to U.S. Provisional Application No. 61 / 288,649, filed December 21, 2009, and U.S. Provisional Application No. 61 / 360,148, filed June 30, 2010, each incorporated by reference in its entirety way incorporated into this article. Background of the invention [0003] Polyesters such as poly(glycolide), poly(lactide) and poly(caprolactone) are biocompatible and biodegradable polymers commonly used in biomedical applications such as drug delivery. Homopolymers of glycolide, lactide, or caprolactone may tend to be too hydrophobic in aqueous environments and may also be difficult to covalently functionalize, which limits their use in certain applications. Efforts have been made to prepare synthetic analogs of glycolide, lactide and caprolactone in an attempt to overcome these limitations. Examples include cyclic esters with unsaturated functional groups that can be reacted to prov...

Claims

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Application Information

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IPC IPC(8): C07D319/12C08G63/08
CPCC07D319/12C08G63/00C08G63/08A61K9/1075A61K9/4866
Inventor P·马克兰X·张
Owner EVONIK DEGUSSA GMBH