Technical method for synthesizing medical biodegradable polylactic acid by catalyzing condensation polymerization of lactic acid through chlorinated bicyclic guanidine

A technology of bicyclic guanidine catalyzing lactic acid and biodegradability is applied in the field of drug degradation materials, which can solve the problems of long catalytic reaction time and hidden danger of product biosafety, and achieve the effects of easy industrialization, low cost of raw materials, and simple reaction process.

Inactive Publication Date: 2014-03-19
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The purpose of the present invention is to solve the problem of hidden dangers of product biological safety and the long catalytic reaction time of organic guanidine catalysts (creatinine and creatinine hydrochloride) which are widely used in the synthesis of polylactic acid by existing polycondensation methods.

Method used

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  • Technical method for synthesizing medical biodegradable polylactic acid by catalyzing condensation polymerization of lactic acid through chlorinated bicyclic guanidine
  • Technical method for synthesizing medical biodegradable polylactic acid by catalyzing condensation polymerization of lactic acid through chlorinated bicyclic guanidine
  • Technical method for synthesizing medical biodegradable polylactic acid by catalyzing condensation polymerization of lactic acid through chlorinated bicyclic guanidine

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Experimental program
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Effect test

Embodiment 1

[0025] Add 20mL of deionized water into the Schleck reaction kettle, then add 2g (14.4mmol) of bicyclic guanidine, heat and stir under the protection of high-purity argon, after the rune reaches the pre-selected temperature of 25°C, add the concentration to the kettle dropwise from the constant pressure dropping funnel 2% hydrochloric acid aqueous solution, control the molar ratio of bicyclic guanidine and hydrochloric acid to 1:1.1, and stir for 5h. The obtained product was rotary evaporated to remove the contained water, and the solid product was moved into a vacuum drying oven to dry for 48 hours to obtain 2.41 g of a white solid product, namely bicyclic guanidine chloride, with a yield of 95.6%.

Embodiment 2

[0027] Add 30mL of deionized water into the Schleck reactor, then add 2g (14.4mmol) of bicyclic guanidine, heat and stir under the protection of high-purity argon, and after the rune reaches the preselected temperature of 55°C, add the concentration to the kettle dropwise from the constant pressure dropping funnel. 4% hydrochloric acid aqueous solution, control the molar ratio of bicyclic guanidine and hydrochloric acid to 1:1.2, and stir for 3 hours. The obtained product was rotary evaporated to remove the contained water, and the solid product was moved into a vacuum drying oven to dry for 48 hours to obtain 2.47 g of a white solid product, namely bicyclic guanidine chloride, with a yield of 98.0%.

Embodiment 3

[0029] Add 20mL of deionized water into the Schleck reaction kettle, then add 2g (14.4mmol) of bicyclic guanidine, heat and stir under the protection of high-purity argon, after the rune reaches the pre-selected temperature of 100°C, add the concentration to the kettle dropwise from the constant pressure dropping funnel 2% hydrochloric acid aqueous solution, control the molar ratio of bicyclic guanidine and hydrochloric acid to 1:1, and stir for 0.5h. The obtained product was rotary evaporated to remove the contained moisture, and the solid product was moved into a vacuum drying oven to dry for 48 hours to obtain 2.34 g of a white solid product, namely bicyclic guanidine chloride, with a yield of 93.2%.

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Abstract

The invention provides a technical method for synthesizing medical biodegradable polylactic acid by catalyzing the condensation polymerization of lactic acid through chlorinated bicyclic guanidine. In the technical method, chlorinated bicyclic guanidine (TBDC1) is taken as a catalyst, industrial grade 90% lactic acid water solution is taken as a monomer, and high-biosecurity polylactic acid is synthesized by solvent-free (body) high-speed condensation polymerization reaction (the reaction time is less than or equal to 12 hours). According to the technical method, the tin catalysts with cytotoxicity can not be used, the used catalyst has biocompatibility and biosecurity, and a synthetic product is suitable for bioengineering materials such as controlled release carriers and target medicament carriers; in a synthetic process, the green catalyst and the green technology (any reagents can not be used, and the toxic products can not be generated) are adopted, so that the green biodegradable material can be synthesized; a polymerization reaction is convenient and easy, low in raw material cost, and short in reaction time, thus the technical reaction is suitable for the industrial production; and the molecular weight of the synthesized product can be adjusted and controlled within the range of 1.0*10<4> to 3.5*10<4>, wherein the molecular weight is narrow in distribution.

Description

Technical field: [0001] The invention belongs to the technical field of drug-degradable materials, and relates to a process for synthesizing medical biodegradable polylactic acid from L-lactic acid catalyzed by a non-toxic organic guanidine compound, bicycloguanidine chloride. Background technique [0002] With the in-depth research and application of controlled release and targeted drug carriers, hard tissue repair materials, and biological tissue engineering materials in medicine and biomedicine, the demand for biodegradable materials with biosafety has increased dramatically. Biodegradable polylactic acid has good biosafety and biocompatibility. As a drug carrier, it can improve the efficacy of the drug and reduce the dosage and side effects of the drug, so it has a good application prospect in the field of biomedicine. At present, the production of commercialized polylactic acid mainly adopts the ring-opening polycondensation method of stannous octoate and the method of ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G63/06C08G63/87
Inventor 李弘张全兴江伟齐运彪黄伟成娜宗绪鹏潘丙才
Owner NANJING UNIV
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