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Process method for synthesizing medical biodegradable polylactic acid by performing polycondensation on lactic acid through catalysis of 1,5,7-triazabicyclo[4.4.0]decane-5-ene (TBD)

A technology for catalyzing lactic acid and biodegradation, applied in the field of drug degradation materials, can solve problems such as potential safety hazards, and achieve the effects of short time, easy industrialization and low cost of raw materials

Inactive Publication Date: 2013-01-16
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The purpose of the present invention is to solve the problem of potential safety hazards of polylactic acid synthesized by tin-based catalysts when used as human drug carriers, and to provide a non-toxic, metal-free bicyclic guanidine compound as a catalyst to directly catalyze the polymerization of lactic acid to form a highly biological Process method of safety medical biodegradation polylactic acid

Method used

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  • Process method for synthesizing medical biodegradable polylactic acid by performing polycondensation on lactic acid through catalysis of 1,5,7-triazabicyclo[4.4.0]decane-5-ene (TBD)
  • Process method for synthesizing medical biodegradable polylactic acid by performing polycondensation on lactic acid through catalysis of 1,5,7-triazabicyclo[4.4.0]decane-5-ene (TBD)
  • Process method for synthesizing medical biodegradable polylactic acid by performing polycondensation on lactic acid through catalysis of 1,5,7-triazabicyclo[4.4.0]decane-5-ene (TBD)

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] 80g of L-lactic acid (mass content 90%) was charged into the reactor, and the vacuuming-argon filling operation was repeated three times. Heating to 100°C under 200 Torr, dehydration reaction for 1h. Then the reactor was depressurized to 100 Torr, and the reaction was continued at 130° C. for 1 h. Then the reactor was depressurized to 30 Torr and the reaction was continued at 160° C. for 1 h to obtain oligomeric lactic acid OLLA.

[0025] Add 240 mg of catalyst bicyclic guanidine to the reactor, depressurize the reactor to 10 Torr, and raise the temperature to 180° C. for 10 h. After stopping the reaction, cool the reactor to room temperature, dissolve the polymer with acetone, then pour it into ethanol at 0°C, filter under reduced pressure, and dry the solid at 50°C under vacuum for 36 hours to obtain a white solid, which is highly biosafety Pharmaceutical polylactic acid, yield 75.6%, polymer molecular weight 1.5×10 4 , PDI 1.87.

Embodiment 2

[0027] 80 g of L-lactic acid (mass content 90%) was charged into the reaction kettle, and the vacuum pumping and argon filling operations were repeated three times. Heated to 110°C under 200 Torr, dehydration reaction for 1h. Then the reactor was depressurized to 100 Torr and the reaction was continued at 130° C. for 1 h. Then the reactor was depressurized to 30 Torr and the reaction was continued at 150° C. for 1 h to obtain oligomeric lactic acid OLLA.

[0028] Add 240 mg of catalyst bicyclic guanidine to the reactor, depressurize the reactor to 10 Torr, and raise the temperature to 190° C. for 16 hours. After stopping the reaction, cool the reactor to room temperature, dissolve the polymer with acetone, then pour it into ethanol at 0°C, filter under reduced pressure, and dry the solid at 50°C under vacuum for 36 hours to obtain a white solid, which is highly biosafety Pharmaceutical polylactic acid, yield 73.1%, polymer molecular weight 2.3×10 4 , PDI 1.70.

Embodiment 3

[0030] 80g of L-lactic acid (mass content 90%) was charged into the reactor, and the vacuuming-argon filling operation was repeated three times. Heating to 120°C under 200 Torr, dehydration reaction for 1h. Then the reactor was depressurized to 100 Torr and the reaction was continued at 130° C. for 1 h. Then the reactor was depressurized to 30 Torr and the reaction was continued at 150° C. for 1 h to obtain oligomeric lactic acid OLLA.

[0031] Add 120 mg of catalyst bicyclic guanidine to the reactor, depressurize the reactor to 10 Torr, and raise the temperature to 200° C. for 20 h. After stopping the reaction, cool the reactor to room temperature, dissolve the polymer with acetone, then pour it into ethanol at 0°C, filter under reduced pressure, and dry the solid at 50°C under vacuum for 36 hours to obtain a white solid, which is highly biosafety Pharmaceutical polylactic acid, yield 70.1%, polymer molecular weight 3.6×10 4 , PDI 1.90.

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Abstract

The invention discloses a method for synthesizing medical biodegradable polylactic acid by directly performing polycondensation on lactic acid through catalysis of 1,5,7-triazabicyclo[4.4.0]decane-5-ene (TBD). According to the method, the polylactic acid product which is high in biosecurity is obtained by taking the TBD as a catalyst, and an industrial grade lactic acid aqueous solution of which the mass content is 90 percent as monomers, and by solvent-free (body) and two-stage condensation polymerization. According to the method, a tin catalyst which has cytotoxicity is eliminated, and the used catalyst has biocompatibility and biosecurity; the synthesized polylactic acid does not contain any metal and other toxic component and is suitable for medical and medicinal fields; the environment-friendly biodegradable polylactic acid is synthesized by an environment-friendly process (in which any reagent is not used and any toxic product is not generated) by using the environment-friendly catalyst; the polymerization reaction is convenient to realize and practicable; raw materials are low in cost, and the industrial production is easy to realize; and the synthesized product is narrow in molecular weight distribution, and the molecular weight can be regulated from 1.0*10<4> to 4.0*10<4>.

Description

Technical field: [0001] The invention belongs to the technical field of drug degradable materials, and relates to a process method for synthesizing polylactic acid with high biological safety by using bicyclic guanidine to catalyze lactic acid. Background technique: [0002] In recent years, with the rapid development of medicine and biomedicine, the demand for degradable materials that can be applied to controlled release and targeted drug carriers, hard tissue repair materials, and bioactive scaffold materials in biological tissue engineering has increased dramatically. Biodegradable polylactic acid has good biocompatibility. As a drug carrier, it can improve drug efficacy, reduce dosage and drug side effects, etc., making it have many important applications in pharmaceutical science and biomedicine. At present, the production of commercialized polylactic acid is mainly synthesized by the ring-opening polycondensation method of stannous octoate and the direct polycondensat...

Claims

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Application Information

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IPC IPC(8): C08G63/06C08G63/87
Inventor 李弘张全兴齐运彪江伟黄伟成娜宗绪鹏潘丙才
Owner NANJING UNIV
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