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Epsilon-caprolactone derivative and polymer thereof

A derivative, caprolactone technology, applied in the field of ε-caprolactone derivatives and their polymers, can solve the problems of limited application, lack of reactive groups, not easy to degrade, etc.

Inactive Publication Date: 2014-02-19
EAST CHINA UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0002] Aliphatic polyesters, such as polycaprolactone (PCL), polylactide (PLA), polyglycolic acid (PGA), have been used in nearly two decades due to their good biodegradability, biocompatibility and non-toxicity However, the vast majority of aliphatic polyesters are hydrophobic, not easy to degrade, and lack reactive groups, which greatly limits their applications, so the preparation of biodegradable polymers containing functional side groups is limited. great attention

Method used

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  • Epsilon-caprolactone derivative and polymer thereof
  • Epsilon-caprolactone derivative and polymer thereof
  • Epsilon-caprolactone derivative and polymer thereof

Examples

Experimental program
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Embodiment 1

[0022] Preparation of Benzyl 4-carbamate cyclohexanol:

[0023] Put trans-p-aminocyclohexanol (10.3g, 89.4mmol) and sodium bicarbonate (18.8g, 224mmol) in a 1L round bottom flask, add 300mL of water, stir to dissolve, and form a colorless transparent solution. The solution was placed in a water bath, and then benzyl chloroformate (16.6mL, 116mmol) was added dropwise for 10 minutes to 20 minutes. Extraction with ethyl acetate and n-butanol. The organic layers were combined, washed with hydrochloric acid and sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated until crystals formed. The product was recrystallized in the original solvent to obtain white needle-like crystals. The yield was 80%.

[0024] 1 H NMR (CDCL 3 ): δ=1.12-2.15(-(C H 2 ) 2 -CH(OH)-(C H 2 ) 2 -), 3.43 (1H, -C H -NH-), 3.58(-C H -OH-), 4.62(-N H -), 5.09(-C H 2 -Ph), 7.30-7.37 (5H, -C 6 H 5 ).

[0025] Preparation of benzyl cyclohexanone 4-carbamate:

...

Embodiment 2

[0031] Preparation of polycaprolactone with amino groups in the side chain:

[0032] 4-benzyl carbamate-ε-caprolactone and ε-caprolactone are mixed in different molar ratios (the molar ratios of 4-benzyl carbamate-ε-caprolactone and ε-caprolactone are respectively 1 : 3; 1: 4; 1: 6; 1: 8; 1: 10; 1: 19) are placed in the polymerization tube after being mixed, and the stannous octanoate of 1 / 1000 of the total monomer molar number is used as a catalyst. Polymerize at 120°C to 150°C for 24 hours to 48) hours, then cool, dissolve in chloroform, and precipitate in methanol to obtain a copolymer.

[0033] Take the above-mentioned copolymer (0.5g~1g), dissolve it in 10mL~20mL tetrahydrofuran, add 0.3g~0.6g Pd / C (catalyst), after several times of hydrogen replacement, at 25°C~50°C, under hydrogen atmosphere React for 24 hours to 72 hours. After the reaction, filter off palladium carbon, spin off tetrahydrofuran, dissolve in chloroform, and precipitate in ether to obtain the target cop...

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Abstract

The invention relates to an epsilon-caprolactone derivative and polymer thereof. The epsilon-caprolactone derivatives have a structure represented by formula I; the polymer is obtained by homopolymerization with compound represented by formula I or copolymerized by caprolactone, lactide and glycolide (number average molecular weight 5000-50000). The polymer is de-protected to obtain the target polymer. Advantages of the invention lie in that by chemical modification of aliphatic polyester compounds, with guidance of reactive groups in main chains, use of the invention in targeting carrier, medical release and tissue engineering is greatly extended; the invention uses simple materials; has low cost and mild reaction conditions. In formula I, R is a chained alkyl or a chained alkyl substituted by arylcycle.

Description

technical field [0001] The present invention relates to a kind of ε-caprolactone derivative and its polymer. Background technique [0002] Aliphatic polyesters, such as polycaprolactone (PCL), polylactide (PLA), polyglycolic acid (PGA), have been used in nearly two decades due to their good biodegradability, biocompatibility and non-toxicity However, the vast majority of aliphatic polyesters are hydrophobic, not easy to degrade, and lack reactive groups, which greatly limits their applications, so the preparation of biodegradable polymers containing functional side groups is limited. received great attention. The ring-opening polymerization of lactone or lactide and functionalized monomers has been reported, and groups such as hydroxyl, carbonyl, mercapto, amino, carboxyl, and halogen have been successfully introduced into the polymer backbone, and can be used in targeting carriers, drugs, etc. Controlled release and tissue engineering have been applied. [0003] In order...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D313/04C08G63/685C08G63/83C08G63/84C08G63/85
Inventor 郎美东严金良
Owner EAST CHINA UNIV OF SCI & TECH
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