Method for synthesizing poly(N-vinylcaprolactam)/polycaprolactone segmented copolymer

A vinyl caprolactam and block copolymer technology, applied in the field of chemical synthesis, can solve problems such as poor solubility, and achieve the effect of improving properties and good application prospects

Active Publication Date: 2012-10-17
LIAONING UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is in order to overcome the shortcoming that PCL is poor in solubility in water, PCL and PNVCL w

Method used

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  • Method for synthesizing poly(N-vinylcaprolactam)/polycaprolactone segmented copolymer
  • Method for synthesizing poly(N-vinylcaprolactam)/polycaprolactone segmented copolymer
  • Method for synthesizing poly(N-vinylcaprolactam)/polycaprolactone segmented copolymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1 Poly N-vinyl caprolactam / polycaprolactone (PNVCL- b -PCL1) Synthesis of block copolymers

[0030] (1) Alkyne-terminated poly-N-vinyl caprolactam (PNVCL-C≡CH)

[0031] 1. Synthesis of carboxyl-terminated poly-N-vinylcaprolactam (PNVCL-COOH)

[0032] Weigh 22.78g (0.16mol) of N-vinylcaprolactam (NVCL), 0.36g (2.20mmol) of azobisisobutyronitrile (AIBN) and dissolve in 80mL of dioxane, and stir for 30min at room temperature under nitrogen. The temperature was raised to 68°C, and the nitrogen gas flow was continued for 30 minutes. Weigh 0.60g (6.52mmol) of thioglycolic acid (TGA), dissolve it in 20mL of dioxane, then add it into the above reaction flask, and react with nitrogen gas for 12h. After the reaction was finished, dioxane was removed by rotary evaporation to obtain a crude product. The crude product was dissolved in 100 mL of dichloromethane and poured into 700 mL of n-hexane for precipitation. The above operation was repeated 4 times, and the obtai...

Embodiment 2

[0054] Example 2 Poly N-vinyl caprolactam / polycaprolactone (PNVCL- b -PCL2) Synthesis of block copolymers

[0055] (1) Synthesis of alkyne-terminated poly-N-vinyl caprolactam (PNVCL-C≡CH): same as Example 1.

[0056] (2) Synthesis of azido-terminated polycaprolactone (N 3 -PCL 2 )

[0057] Weigh 5.13g (45mmol) ε-caprolactone (ε-CL), 0.13g (1.49mmol) azide ethanol (N 3 -CH 2 CH 2 OH), 0.15g (0.37mmol) stannous octoate (Sn(Oct) 2 ) was dissolved in 15mL of toluene, vacuumed and blown with nitrogen for 6 times, and stirred at 80°C for 12h. The toluene was removed by rotary evaporation to obtain a colorless viscous liquid. The viscous liquid was dissolved with 10mL of dichloromethane and poured into 80mL of n-hexane for precipitation. Repeat the above operation 3 times, and the precipitate is vacuum-dried to obtain a white powder end azido polycaprolactone (N 3 -PCL 2 ) 5.10g, yield 94%.

[0058] (3) Synthesis of PNVCL- b -PCL2

[0059] Weigh 1.10g (0.27mmol) PNVCL...

Embodiment 3

[0060] Example 3 Poly N-vinyl caprolactam / polycaprolactone (PNVCL- b -PCL3) Synthesis of block copolymers

[0061] (1) Synthesis of alkyne-terminated poly-N-vinyl caprolactam (PNVCL-C≡CH): same as Example 1.

[0062] (2) Synthesis of azido-terminated polycaprolactone (N 3 -PCL 3 )

[0063] Weigh 3.77g (33.07mmol) ε-caprolactone (ε-CL), 0.055g (6.32mmol) azidoethanol (N 3 -CH 2 CH 2 OH), 0.050g (0.12mmol) stannous octoate (Sn(Oct) 2 ) was dissolved in 15mL of toluene, vacuumed and blown with nitrogen for 6 times, and stirred at 80°C for 12h. The toluene was removed by rotary evaporation to obtain a colorless viscous liquid. The viscous liquid was dissolved with 10mL of dichloromethane and poured into 80mL of n-hexane for precipitation. Repeat the above operation 3 times, and the precipitate is vacuum-dried to obtain 1.43 g of white powder, which is PNVCL- b -PCL3 Yield 88%. The product was confirmed by infrared spectroscopy, nuclear magnetic resonance and gel per...

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Abstract

The invention relates to a method for synthesizing a poly(N-vinylcaprolactam)/polycaprolactone segmented copolymer. The employed technical scheme comprises that: moderate alkyne-terminated poly(N-vinylcaprolactam) and azido-terminated polycaprolactone, under the catalysis of sodium ascorbate and blue vitriod, in the mixed solvent of tetrahydrofuran and water, are stirred and reacted for 40-60 h at the temperature of 25 DEG C; rotary evaporation is carried out on the reaction mixture to remove the solvent; anhydrous dichloromethane is used to dissolve the reaction mixture; the dissolved reaction mixture is slowly added dropwise to normal hexane for precipitation; the precipitant is filtered out; and vacuum drying at 30 DEG C is carried out on the precipitant to produce a target product. With the method of the invention, the copolymerization of PNVCL and PCL is realized, and the amphipathic PNVCL-b-PCL segmented copolymer is obtained. The amphipathic PNVCL-b-PCL segmented copolymer can form micelles with kernals and shell structures through self-assembly in water, and has a good application prospect in the fields of controlled drug release, targeted drug delivery, etc.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, in particular to a synthetic poly-N-vinyl caprolactam / polycaprolactone (PNVCL- b -PCL) block copolymer method. Background technique [0002] Poly-N-vinylcaprolactam (PNVCL) is a temperature-sensitive polymer with a low critical phase transition temperature (LCST). Its solubility in solution will slowly decrease with the increase of temperature, but once the temperature rises to a small range near LCST, its solubility will suddenly decrease, and heat sinking will occur, and this change is reversible. The LCST of PNVCL is just in the physiological temperature range (30~40°C), which makes it have extremely wide application prospects in biology, medical materials and daily chemicals. [0003] Polycaprolactone (PCL) is a partially crystalline polymer with a melting point and glass transition temperature of 50°C and 60°C, respectively. It is rubbery at room temperature, has good thermal stability, ...

Claims

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Application Information

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IPC IPC(8): C08G81/02C08F126/04C08F8/14C08G63/685C08G63/08
Inventor 张国林矣杰吴秋华宋溪明
Owner LIAONING UNIVERSITY
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