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Polycaprolactone with reactive group on side chain and preparation method of polycaprolactone

A technology of polycaprolactone and reactivity, applied in the chemical field, can solve the problems of low hydrophilicity, limited application, lack of active functional groups, etc., and achieve the effect of improving hydrophilicity, simple method, and expanding application

Inactive Publication Date: 2015-05-20
CHONGQING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, some inherent properties of PCL limit its application in the biomedical field
On the one hand, the PCL molecule is a long carbon chain containing an ester group. The molecular structure determines that PCL is a hydrophobic material with very low hydrophilicity, which limits its application in the controlled release of hydrophilic drugs such as proteins.
On the other hand, PCL lacks active functional groups and has no reactive sites for grafting bioactive molecules, making it difficult to form bioactive materials.

Method used

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  • Polycaprolactone with reactive group on side chain and preparation method of polycaprolactone
  • Polycaprolactone with reactive group on side chain and preparation method of polycaprolactone
  • Polycaprolactone with reactive group on side chain and preparation method of polycaprolactone

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1, azide caprolactone (CL-N 3 )Synthesis

[0031]Dissolve 20 g of α-chlorocaprolactone in 100 mL of dimethylformamide (DMF), stir and dissolve at room temperature, add sodium azide in a molar ratio of 1:1 according to the molar content of chlorine, and stir overnight at 15°C , add diethyl ether to precipitate the product, and wash with diethyl ether to remove DMF, dissolve the obtained product in toluene, centrifuge at 4000r / min for 15min to desalt, take the supernatant after centrifugation, remove toluene under reduced pressure, and obtain 18.2g hexyl azide Esters, denoted as CL-N 3 . CL-N 3 Infrared spectrum detection was carried out, and CL-Cl and ε-CL were used as controls at the same time, the results were as follows figure 1 shown. The results show that at 2106cm -1 appears N 3 The characteristic absorption peaks indicated that the azidation was successful.

Embodiment 2

[0032] Embodiment 2, azide caprolactone (CL-N 3 )Synthesis

[0033] Dissolve 20 g of α-chlorocaprolactone in 100 mL of dimethyl sulfoxide (DMSO), stir and dissolve at room temperature, add sodium azide in a molar ratio of 1:1 according to the molar content of chlorine, and stir overnight at 40°C. Add diethyl ether to precipitate the product, wash with diethyl ether to remove DMSO, dissolve the obtained product in toluene, centrifuge at 4000r / min for 15min to remove salt, take the supernatant after centrifugation, and then distill toluene under reduced pressure to obtain 17.8g hexyl azide Lactone, denoted as CL-N 3 . CL-N 3 Infrared spectrum detection, while using CL-Cl and ε-CL as controls. The obtained infrared spectrum and figure 1 Similar, at 2107cm -1 appears N 3 The characteristic absorption peak indicates that the azidation is successful.

Embodiment 3

[0034] Embodiment 3, the synthesis of caprolactone (CL-COOH) with-COOH

[0035] Get the CL-N that embodiment 1 makes 3 Dissolve 4.5g in 40mL methanol solvent, add equimolar 4-pentynoic acid, stir to fully dissolve and mix evenly; then add 4mL of 10mg / mL copper sulfate pentahydrate solution; nitrogen exhaust the air in the reaction bottle, and then in Add 6 mL of newly prepared 100 mg / mL sodium ascorbate solution under the protection of nitrogen, stir and react overnight at 25 °C under the protection of nitrogen, distill the methanol off under reduced pressure, dissolve the product in tetrahydrofuran, centrifuge at 4000 r / min for 15 min to remove salt, and take the supernatant after centrifugation Liquid, tetrahydrofuran was distilled off under reduced pressure to obtain 3.5 g of caprolactone with -COOH, denoted as CL-COOH. CL-COOH was detected by infrared spectroscopy, the results are as follows figure 1 shown. The results show that 2106cm -1 Office N 3 The characteristic...

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Abstract

The invention discloses polycaprolactone with a reactive group on a side chain and a preparation method of the polycaprolactone. The side chain of the reactive polycaprolactone contains -COOH, the hydrophilic-hydrophobic property of the reactive polycaprolactone can be adjusted by adjusting the content of the -COOH, the -COOH on the side chain has a reaction property and can be used for chemically fixing bioactive molecules, the bioactivity of the polycaprolactone is achieved, and the application range of the polycaprolactone can be enlarged.

Description

technical field [0001] The invention belongs to the field of chemistry, and in particular relates to a polycaprolactone with a reactive group in a side chain and a preparation method thereof. Background technique [0002] Bioactive materials are biological materials with specific biological activities, such as inducing cell-specific adhesion or promoting proliferation. It is a research and development focus in the field of biomaterials, usually by covalently introducing bioactive molecules to the host material. Achieved. Polycaprolactone (poly(ε-caprolactone, PCL) is an aliphatic linear polyester, which is a semi-crystalline polymer, and can be obtained by ring-opening polymerization or coordination polymerization of ε-caprolactone. PCL is An aliphatic polyester approved by the U.S. Food and Drug Administration (FDA), widely used in controlled drug release, surgical sutures, and tissue engineering due to its biocompatibility, biodegradability, and processability The repeat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G63/685C08G63/08
Inventor 罗彦凤刘娟但傲欢张立倩王锦峰
Owner CHONGQING UNIV
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