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Synthesis of medicinal biodegradable poly(epsilon-caprolactone) and application method thereof

A synthesis method and technology of caprolactone, applied in the field of polymer chemistry, can solve the problems of cumbersome process, harsh storage conditions, heavy metal residue, etc., and achieve the effect of simple process, improved reaction efficiency, and mild and controllable process

Inactive Publication Date: 2010-09-15
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] After searching the prior art documents, it is found that Chinese Patent Document No. CN 1341674A discloses a method for preparing poly(ε-caprolactone) by bulk ring-opening polymerization in the presence of initiator butyl titanate Ti(OBu), The disadvantage is that the product needs to be separated and purified in multiple steps, the process is cumbersome, and the butyl titanate used is very easy to absorb moisture, the storage conditions are harsh, and there will be heavy metal residues in the reaction system.
[0005] Further retrieval found that Chinese Patent Document No. CN105554306C discloses a method for synthesizing poly(ε-caprolactone) using hyperthermophilic esterase as a catalyst. -caprolactone) has a number average molecular weight of only 1200-2300g / mol, cannot be directly precipitated and needs to be separated by low-temperature centrifugation, and the molecular weight is too low to be widely used as a drug carrier

Method used

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  • Synthesis of medicinal biodegradable poly(epsilon-caprolactone) and application method thereof
  • Synthesis of medicinal biodegradable poly(epsilon-caprolactone) and application method thereof
  • Synthesis of medicinal biodegradable poly(epsilon-caprolactone) and application method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Bulk Polymerization of ε-Caprolactone

[0025] Mix 5g of ε-caprolactone with 0.05g of Novozym 435 (the mass ratio of ε-caprolactone is 1%), put it into a clean and dry reaction bottle, exchange it with nitrogen three times, and then depressurize to 2mm Hg pressure , shaking reaction at 60°C for 2h, adding 10ml of dichloromethane to the reactant to terminate the reaction, filtering to remove the enzyme, the filtrate was concentrated in vacuo, and the concentrated solution was subjected to proton nuclear magnetic resonance ( 1 H NMR) determined that the monomer conversion rate was 90.2%. The residual concentrate was poured into 5 times the volume of petroleum ether to precipitate, and the precipitate was collected after filtration and dried in vacuo for 48 hours. The product was determined by gel permeation chromatography (GPC) to have a number average molecular weight of 7000 g / mol and a polydispersity of 1.3.

Embodiment 2

[0027] Solution Polymerization of ε-Caprolactone

[0028] Mix 5g ε-caprolactone with 0.5g Novozym 435 (the mass ratio of ε-caprolactone is 10%), put it into a clean and dry reaction bottle, ventilate it with nitrogen three times, and add it with a syringe after sealing. -The volume ratio of caprolactone is 2.0:1 toluene, stirred and reacted at 80°C for 7h, added 10ml of dichloromethane to terminate the reaction, filtered to remove the enzyme, the filtrate was concentrated in vacuo, and the concentrated filtrate was subjected to nuclear magnetic resonance spectroscopy ( 1 H NMR) determined that the monomer conversion rate was 95.4%. The residual concentrate was poured into 5 times the volume of petroleum ether to precipitate, and the precipitate was collected after filtration and dried in vacuo for 48 hours. The product was determined by gel permeation chromatography (GPC), with a number average molecular weight of 42000 g / mol and a polydispersity of 1.2.

[0029] Such as fi...

Embodiment 3

[0032] Solution Polymerization of ε-Caprolactone

[0033] Mix 5g of ε-caprolactone with 1g of Novozym 435 (the mass ratio of ε-caprolactone is 20%), put it into a clean and dry reaction bottle, ventilate it with nitrogen three times, and add ε-caprolactone with a syringe after sealing. The volume ratio of the lactone is 5.0:1 toluene, stirred and reacted at 80°C for 10h, added 20ml of dichloromethane to terminate the reaction, filtered to remove the enzyme, the filtrate was concentrated in vacuo, and the concentrated filtrate was subjected to hydrogen nuclear magnetic resonance spectroscopy ( 1 H NMR) determined that the monomer conversion rate was 98.3%. The residual concentrate was poured into 5 times the volume of ethanol to precipitate, and the precipitate was collected after filtration and dried in vacuum for 48 hours. The product was determined by gel permeation chromatography (GPC) to have a number average molecular weight of 57000 g / mol and a polydispersity of 1.4.

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Abstract

The invention relates to synthesis of medicinal biodegradable poly(epsilon-caprolactone) and an application method thereof in the field of high polymer chemistry technique. The medicinal biodegradable poly (epsilon-caprolactone) can be obtained by separating and purifying the reactant after epsilon-caprolactone and immobilized lipase Novozym 435 are mixed and reacted at the temperature of between 60 and 80 DEG C for 2 to 48 hours by using a mass polymerization method or a solution polymerization method in a closed reaction system. Due to the adoption of the immobilized lipase Novozym 435 which serves as a catalyst, the biodegradable poly (epsilon-caprolactone) can be prepared by the method which has the advantages of no catalyst residue and easy control of conditions.

Description

technical field [0001] The invention relates to a preparation and application method in the technical field of polymer chemistry, in particular to a synthesis and application method of medicinal biodegradable poly(ε-caprolactone). Background technique [0002] Poly(ε-caprolactone) is a semi-crystalline aliphatic polyester, which has been widely used in the fields of biomedicine and drug controlled release due to its good biodegradability, biocompatibility and drug permeability. research and application. The current synthesis method of poly(ε-caprolactone) is obtained by organometallic catalyzed ring-opening polymerization of ε-caprolactone monomer, but harsh reaction conditions and residual toxicity of heavy metal catalysts limit the synthesis of poly(ε-caprolactone) ) in many fields, such as biomedicine and drug delivery. [0003] Enzymatic polymerization is a new enzyme-catalyzed polymerization method developed in recent years. Compared with other catalytic methods, enz...

Claims

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Application Information

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IPC IPC(8): C12P17/08A61L27/18A61L31/06A61K47/34
Inventor 郭圣荣侯静文雷磊
Owner SHANGHAI JIAO TONG UNIV
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