Cholesterol ester-containing amphiphilic polymer sensitive to temperature and pH value and its prepn process

A technology of cholesteryl ester and pH, which is applied in the field of amphiphilic polymers and its preparation, can solve the problems of poor biocompatibility and achieve the effects of low synthesis cost, high yield, and good double sensitivity

Inactive Publication Date: 2006-11-08
TSINGHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] However, the hydrophobic units of all reported amphiphilic polymers are long-chain fatty alcohol esters, and their biocompatibility is poorer than that of cholesterol.

Method used

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  • Cholesterol ester-containing amphiphilic polymer sensitive to temperature and pH value and its prepn process
  • Cholesterol ester-containing amphiphilic polymer sensitive to temperature and pH value and its prepn process
  • Cholesterol ester-containing amphiphilic polymer sensitive to temperature and pH value and its prepn process

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Embodiment 1

[0020] Embodiment one: the synthesis of N-isopropylacrylamide / acrylic acid / cholesteryl acrylate copolymer: wherein R 1 with R 2 Same as cholesteryl acrylate, R 3 , R 4 , R 5 and R 6 Same, for acrylic.

[0021] 1. Synthesis of cholesteryl acrylate: the molar ratio of raw materials is cholesterol:acryloyl chloride=1:3.5. Dissolve 12.12g (0.0314mol) of cholesterol and 0.11mol of acryloyl chloride in 50ml of anhydrous benzene, add 0.15g of hydroquinone as a polymerization inhibitor, and heat to reflux for 7 hours. The reaction solution was dissolved in 70ml ether, followed by saturated Na 2 CO 3 solution, 10% HCl solution, washed with saturated NaCl solution; separated to collect the organic phase, anhydrous MgSO 4 Let dry overnight. Most of the solvent was evaporated by rotary evaporation, and the concentrated solution was redissolved in 30 ml of anhydrous ether, and then 300 ml of absolute ethanol was added for precipitation to obtain a white powdery solid with a yield ...

Embodiment 2

[0023] Embodiment two: the synthesis of N-isopropylacrylamide / acrylic acid 2-(N,N dimethylamino)ethyl ester / cholesteryl acrylate copolymer: R 1 with R 2 Same as cholesteryl acrylate, R 3 , R 4 , R 5 and R 6 Same, 2-(N,N dimethylamino)ethyl acrylate.

[0024] 1. Synthesis of cholesteryl acrylate: the molar ratio of raw materials is cholesterol:acryloyl chloride=1:5. Dissolve 12.12g (0.0314mol) of cholesterol and 0.157mol of acryloyl chloride in 50ml of anhydrous benzene, add 0.15g of hydroquinone as a polymerization inhibitor, and heat to reflux for 10 hours. The reaction solution was dissolved in 70ml ether, followed by saturated Na 2 CO 3 solution, 10% HCl solution, washed with saturated NaCl solution; separated to collect the organic phase, anhydrous MgSO 4 Let dry overnight. Most of the solvent was evaporated by rotary evaporation, and the concentrated solution was redissolved in a certain amount of 30ml of ether, and then 300ml of absolute ethanol was added for pr...

Embodiment 3

[0027] Embodiment three: the synthesis of N-isopropylacrylamide / 2-(N,N diethylamino)ethyl methacrylate / cholesteryl methacrylate copolymer: R 1 with R 2 Same as cholesteryl methacrylate, R 3 , R 4 , R 5 and R 6 Same, 2-(N,N diethylamino)ethyl methacrylate.

[0028] 1. Synthesis of cholesteryl methacrylate: The molar ratio of raw materials is cholesterol:methacryloyl chloride=1:4. Dissolve 12.12g (0.0314mol) of cholesterol and 0.126mol of methacryloyl chloride in 60ml of anhydrous benzene, add 0.2g of hydroquinone as a polymerization inhibitor, and heat to reflux for 8 hours. The reaction solution was dissolved in 60ml ether, followed by saturated Na 2 CO 3 solution, 10% HCl solution, washed with saturated NaCl solution; separated to collect the organic phase, anhydrous MgSO 4 Let dry overnight. Most of the solvent was evaporated by rotary evaporation, and the concentrated solution was redissolved in a certain amount of 30ml of ether, and then 300ml of absolute ethanol ...

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Abstract

The invention relates to a cholesteryl ester-containing amphiphilic polymer sensitive to temperature and pH, belonging to the technical field of polymer materials. Its preparation method is: using cholesteryl ester, unsaturated amine monomer, N-isopropylacrylamide and unsaturated carboxylic acid monomer as raw materials, using benzene, tetrahydrofuran or 1,4-dioxane as solvent, And add the initiator, wherein the molar ratio of various raw materials is N-isopropylacrylamide: cholesteryl ester: unsaturated carboxylic acid: unsaturated amine=100: 1~50: 0~50: 0~50, the initiator The dosage is 0.1-1% of the total amount of the above-mentioned monomers, the reaction temperature is 30-70° C., and the reaction time is 10-40 hours. The method of the present invention has the advantages of simple synthesis process, low product synthesis cost and high yield, and the synthesized amphiphilic polymer can be directly or modified by other ways and used for drug and gene carriers, phase transfer catalysis, Various applications such as nanoscale catalysis and reactors.

Description

technical field [0001] The invention relates to a temperature- and pH-sensitive amphiphilic polymer containing cholesteryl ester and a preparation method thereof, belonging to the technical field of polymer materials. Background technique [0002] Amphiphilic compounds include both a hydrophilic group and an lipophilic group in one molecule, so that they have an "amphiphilic function" that is both hydrophilic and lipophilic. In nature and daily life, a large number of so-called "amphiphilic" molecules that are both hydrophilic and lipophilic exist and are used. For example, many biological tissues are composed of amphiphilic molecules, and this amphiphilic structure plays a very important role in life processes such as biological evolution and metabolism. Amphiphilic polymers are macromolecules that are amphiphilic. Amphiphilic polymers can generally be divided into the following categories: AB or ABA block copolymers, random amphiphilic polymers, graft polymers, star poly...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F220/56C08F4/34
Inventor 曾宏波李耀邦张昊宇王晓工
Owner TSINGHUA UNIV
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