Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Fat ester carbonate polymer with side carboxy, its synthesis and use thereof

A technology of aliphatic carbonate and benzyloxycarbonyl trimethylene carbonate, which is applied in the field of synthesis of aliphatic carbonate monomers and their polymers, which can solve the difficulties of bonding drugs, limited applications, and unsatisfactory biodegradability, etc. question

Inactive Publication Date: 2006-03-15
CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
View PDF3 Cites 19 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This series of patents is limited to the homopolymer of this monomer. It is a well-known fact that the biodegradability of homopolymerized aliphatic carbonate in the human body is not ideal, so its application in biomedicine will be limited.
In this patent, methyl or ethyl groups are used to protect the carboxyl group, and it is limited to converting the ester group into an amide group through aminolysis, so it is difficult to further bond drugs, antibodies or other bioactive molecules to the polymer

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Fat ester carbonate polymer with side carboxy, its synthesis and use thereof
  • Fat ester carbonate polymer with side carboxy, its synthesis and use thereof
  • Fat ester carbonate polymer with side carboxy, its synthesis and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0028] 9.00 g of 2,2-dimethylolpropionic acid and 4.30 g of potassium hydroxide were dissolved in 50 ml of N,N-dimethylformamide. Stir vigorously for 1 h at 100°C to form potassium salt of 2,2-dimethylolpropionate. Then 13.80 g of benzyl bromide was added to the above solution, and stirred vigorously for another 15 h at 100°C. The solvent was distilled off, the residue was dissolved in 200 ml of ether, washed three times with 50 ml of distilled water, and finally recrystallized with toluene to obtain 8.95 g of 2-methyl-2-benzyloxycarbonyl-1,3-propanediol with a yield of 60%. Its structure was confirmed by proton NMR spectroscopy, see attached figure 1 .

Embodiment 2

[0029] Embodiment 2: the synthesis of 2-methyl-2-benzyloxycarbonyl trimethylene carbonate

[0030] Dissolve 10 g of 2-methyl-2-benzyloxycarbonyl-1,3-propanediol and 28.5 g of ethyl chloroformate in 600 ml of tetrahydrofuran, and cool in an ice-water bath. Then 28 g of triethylamine was slowly added to the above solution, and the system was kept at 0° C. during the addition. Then react at room temperature for 10h. The precipitate was filtered off, the filtrate was concentrated under reduced pressure, and the residue was recrystallized from tetrahydrofuran and diethyl ether to obtain 9.0 g of white crystals with a yield of 82%. Its structure was confirmed by proton NMR spectroscopy, see attached figure 2 .

Embodiment 3

[0031] Embodiment 3: Synthesis of copolymers of 2-methyl-2-benzyloxycarbonyl trimethylene carbonate and lactic acid in different proportions

[0032] Under anhydrous and oxygen-free conditions, take different proportions of 2-methyl-2-benzyloxycarbonyl trimethylene carbonate and lactide monomer, and add ethyl zinc of 1 / 200 of the total mass of the monomer as a trigger reagent, stirred and reacted at 100°C for 20h, the product was dissolved in dichloromethane, settled with methanol, filtered, washed, dried in vacuo at 35°C for 24h, weighed to calculate the yield, and different proportions of 2-methyl-2-benzyloxy Copolymer of carbonyl trimethylene carbonate and lactic acid. The obtained polymerization results are shown in Table 1.

[0033] Table 1. Copolymers of 2-methyl-2-benzyloxycarbonyl trimethylene carbonate and lactic acid in different proportions

[0034]

[0035] 2

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

A fatty carbonate ester polymer with side carboxy, its synthesis and use are disclosed. The process is carried out by taking 2,2-dimethylolpropionic acid as raw material, synthesizing 2-methyl-2-carbobenzoxy trimethylene-carbonic ether, ring-opening polymerizing or having copolymerization with fatty cyclic ester monomer, catalyzing, hydrogenating, and removing protection to obtain fatty polycarbonate with side chain or copolymer of fatty cyclic ester and carbonic ester. It has biological degradation and non-toxic products, better biological compatibility and activity. It can be used for medicine release, high polymer medicine and tissue engineering.

Description

technical field [0001] The invention relates to the synthesis and application of aliphatic carbonate monomers with side carboxyl groups and polymers thereof. 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 have been widely used in the fields of surgical sutures, artificial skin, artificial blood vessels, bone fixation and repair, and controlled release of drugs because they do not require secondary surgery to remove after implantation. Biodegradable synthetic polymers mainly include aliphatic polyesters, polyamino acids, polyphosphates, polyanhydrides, polyorthoesters, polycarbonates, and the like. Aliphatic polyesters, such as polylactide (PLA), polyglycolide (PGA), polyε-caprolactone (PCL), have low immunogenicity and good biodegradability and bi...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
IPC IPC(8): C08G64/02C08G64/20C07C69/96A61K47/34
Inventor 景遐斌谢志刚关会立陈学思吕常海
Owner CHANGCHUN INST OF APPLIED CHEMISTRY - CHINESE ACAD OF SCI
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com