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Epsilon-caprolactone derivatives and preparation method and application thereof

A derivative, caprolactone technology, applied in the field of lactone monomer and its polymer, can solve the problems of PCL main chain scission, hindering lactone ring-opening polymerization, low polymer molecular weight, etc., and achieve mild synthesis conditions. , the effect of improving hydrophilicity

Inactive Publication Date: 2017-10-27
EAST CHINA UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Such a preparation process is very complicated and cumbersome, and the introduction of the protective group on the functional group has certain side effects on the ring-opening polymerization and deprotection of caprolactone.
For example, a large protecting group has a steric hindrance effect, which hinders the ring-opening polymerization of the lactone, so that the molecular weight of the polymer is not high; in addition, for the protection and deprotection of the active group related to the side group, it is often faced with the removal of the protecting group. Unclean or broken chains in the main chain of PCL, these defects seriously restrict the application of functionalized caprolactone in biomedical materials

Method used

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  • Epsilon-caprolactone derivatives and preparation method and application thereof
  • Epsilon-caprolactone derivatives and preparation method and application thereof
  • Epsilon-caprolactone derivatives and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0040] Embodiment 1: the preparation of 4-formic acid cyclohexanone

[0041]4-Ethyl formate cyclohexanone (20g, 0.11mol) was slowly added to 200ml NaOH (2.75mol / L) aqueous solution, after mixing evenly, the reaction was continued at room temperature for 24h, and the reaction was terminated when the solution turned dark brown. The reaction solution was extracted three times with dichloromethane to remove unreacted raw materials; excess hydrochloric acid was added in batches to the brown aqueous solution in which the product was dissolved, until the reaction solution was light red, then the reaction solution was washed three times with dichloromethane solution, and the solution was combined. A certain amount of anhydrous magnesium sulfate was added to the dichloromethane solution containing the product to dry overnight, and then the reaction solution was concentrated by filtration to obtain 11.83 g of white snowflake-like solid 4-cyclohexanone carboxylate (yield 70.84%).

[0042...

Embodiment 2

[0044] Embodiment 2: the preparation of 4-formic acid isopropanamide cyclohexanone (CYCL)

[0045] Reaction in which cyclohexanone p-formate (11g, 0.0773mol), dicyclohexylcarbodiimide (15.95g, 0.0773mol) and N-hydroxysuccinimide (8.896g, 0.0773mol) were added to 200ml of dichloromethane In the flask, quickly put the flask containing the reaction solution into an ice-water bath and continue to stir for 2 hours, then slowly drop 9.8ml of isopropylamine solution into the reaction solution. After dropwise addition and reaction for 1 hour, withdraw from the water bath and continue the reaction at room temperature for 24 hours. During the reaction, a large amount of white solids will be precipitated. After the reaction is completed, filter and remove the precipitated by-product dicyclohexylurea. Sodium chloride solution was washed three times, dried overnight with anhydrous magnesium sulfate, concentrated and purified by column chromatography (ethyl acetate:petroleum ether=6:1) or r...

Embodiment 3

[0048] Embodiment 3: Preparation of 4-formic acid isopropanamide-ε-caprolactone (NICL)

[0049] 4-Formic acid isopropanamide cyclohexanone (6.6g, 0.0367mol) was slowly added dropwise into a dichloromethane solution dissolved with m-chloroperoxybenzoic acid (8.9g, 0.04404mol), and the reaction was terminated after 36 hours at room temperature. The reaction solution was washed three times successively with saturated sodium thiosulfate, sodium bicarbonate and sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated to remove the solvent. The crude product could be passed through column chromatography (eluent ethyl acetate: petroleum ether = 6:1) or purified by recrystallization from ethyl acetate / n-hexane to obtain 1.68 g of white solid (yield 23.01%) (melting point 159.4° C.).

[0050]

[0051] 1 HNMR (CDCl 3 ): δ=5.84(-C(O)-NH-CH-), 4.17-4.22, 4.46-4.50(-C(O)-O-CH 2 -CH 2 -),4.01-4.08(-NH-CH(CH 3 ) 2 ), 2.60-2.64, 2.85-2.70 (-CH 2 -CH 2 -C(O)...

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Abstract

The invention relates to the field of biomedical materials, and concretely relates to novel water-soluble epsilon-caprolactone derivatives for preparing biomedical polymer materials with biodegradability, wherein the structural formula of the derivatives is shown as a formula (I). The invention also provides epsilon-caprolactone derivative polymers and a preparation method and application thereof. The epsilon-caprolactone derivatives have the advantages of mildness and safety in synthesis conditions, simpleness, cheapness, abundance and easy availability in raw materials and the like; and the epsilon-caprolactone derivative polymers can remarkably improve the polyester hydrophilcity, the polyester crystallinity, the polyester degradation rate and the like, and can be applied to the field of the biomedical materials.

Description

technical field [0001] The invention relates to the field of biomedical materials, in particular to a lactone monomer of a biodegradable medical polymer material, a polymer thereof, a preparation method and an application thereof. Background technique [0002] Polyε-caprolactone (PCL) is a hydrophobic, semi-crystalline, degradable aliphatic polymer, which has good biocompatibility, drug permeability and mechanical properties, and has passed FDA certification. It has received extensive attention in the fields of sustained drug release and tissue engineering. However, due to the shortcomings of PCL, such as strong crystallinity, poor hydrophilicity, slow degradation rate, and lack of reactive functional groups, its application in the biomedical field is limited. For example, the long degradation cycle limits the tissue replacement of PCL in the field of medical scaffolds, and its strong mechanical properties limit its application in soft tissue engineering. Therefore, the fu...

Claims

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Application Information

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IPC IPC(8): C07D313/04C08G63/08
CPCC07D313/04C08G63/08C08G2230/00
Inventor 郎美东张俊肖艳
Owner EAST CHINA UNIV OF SCI & TECH
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