Amphiphilic block copolymer and preparation method thereof

An amphiphilic block and polymer technology, which is used in pharmaceutical formulations, medical preparations with inactive ingredients, and emulsion delivery, etc. Dissolving in supercritical carbon dioxide and other problems, achieving the effects of complete morphology, good drug encapsulation efficiency, and no organic solvent residues

Active Publication Date: 2015-06-24
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But on the one hand, this method cannot completely remove the organic solvent in the micelles, which may cause additional side effects in the clinical use of the prepared drug-loaded micelles; on the other hand, this method will produce volatile organic compounds during the preparation process Pollution
In order to overcome this shortcoming, patent 200810235050.2 proposes a method for preparing amphiphilic block polymer drug-loaded micelles using water-supercritical carbon dioxide system induction method, but due to the existing amphiphilic block polymer (one end hydrophilic , hydrophobic at one end) are difficult to dissolve in supercritical carbon dioxide. Therefore, it is difficult for the existing amphiphilic block polymers to obtain a complete morphology, high drug loading, and drug encapsulation efficiency by using the water-supercritical carbon dioxide induction method. Good drug-loaded micelles, so the development of an amphiphilic block polymer with both a hydrophilic end and a supercritical carbon dioxide end is necessary

Method used

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  • Amphiphilic block copolymer and preparation method thereof
  • Amphiphilic block copolymer and preparation method thereof
  • Amphiphilic block copolymer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: Preparation of an amphiphilic block polymer with one end hydrophilic and one end hydrophilic to supercritical carbon dioxide:

[0026] Step 1, the preparation of vinyl acetate monomer polymerization segment:

[0027] Dissolve 25g vinyl acetate, 2.3g chain transfer agent O-ethyl xanthate propionate and 0.7g azobisisobutyronitrile in 100ml ethanol solution, stir and react at 50 ° C for 10 hours, after the reaction the ethanol solution obtains A vinyl acetate polymer segment with a double bond at the end;

[0028] Step 2, preparation of amphiphilic block polymer:

[0029] Add 25 g of n-butyl methacrylate and 0.7 g of azobisisobutyronitrile to the ethanol solution containing the vinyl acetate polymerized segment in step 1, and stir the reaction at 70 ° C for 16 hours. After the reaction, the organic solvent ethanol is removed by rotary evaporation. Obtain the polymer crude product with amphiphilic properties, dissolve the polymer crude product in 50 ml of dichl...

Embodiment 2

[0030] Example 2: Preparation of an amphiphilic block polymer with one end hydrophilic and one end hydrophilic to supercritical carbon dioxide:

[0031] Step 1, the preparation of vinyl acetate monomer polymerization segment:

[0032] Dissolve 12.5g vinyl acetate, 0.6g O-ethylxanthate ethyl propionate and 0.2g azobisisobutyronitrile in 100ml acetonitrile solution, stir and react at 70°C for 5 hours, after the reaction, the end band is obtained in the acetonitrile solution. Double bond vinyl acetate polymer segment;

[0033] Step 2, preparation of amphiphilic block polymer:

[0034] 37.5 g of hydroxyethyl methacrylate and 0.2 g of azobisisobutyronitrile were added to the acetonitrile solution containing vinyl acetate polymerized segments in step 1, and the reaction was stirred at 90° C. for 10 hours, and the organic solvent acetonitrile was removed by rotary evaporation to obtain The crude polymer product with amphiphilic properties was dissolved in 50 ml of dichloromethane, ...

Embodiment 3

[0035] Example 3: Preparation of an amphiphilic block polymer with one end hydrophilic and one end hydrophilic to supercritical carbon dioxide:

[0036] Step 1, the preparation of vinyl acetate monomer polymerization segment:

[0037] Dissolve 37.5g of vinyl acetate, 0.1g of O-ethylxanthate ethyl propionate and 0.05g of azobisisobutyronitrile in 100ml of 1,4-dioxane solution, stir and react at 90 ° C for 6 hours, the reaction The latter 1,4-dioxane solution obtains a vinyl acetate polymerized segment with double bonds at the end;

[0038] Step 2, preparation of amphiphilic block polymer:

[0039] To the 1,4-dioxane solution containing vinyl acetate polymerized segments in step 1, add 12.5 g polyethylene glycol dimethacrylate (wherein the number of polyethylene glycol monomer segments is 3) and 0.05 g Azobisisobutyronitrile was stirred at 90°C for 12 hours, and the organic solvent 1,4-dioxane was removed by rotary evaporation to obtain a crude polymer product with amphiphilic...

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PUM

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Abstract

The invention discloses an amphiphilic block copolymer, which is copolymerized by a hydrophilic alpha-methyl unsaturated olefinic bond monomer polymer chain segment and a vinyl acetate monomer polymer chain segment of hydrophilic supercritical carbon dioxide, so as to obtain the amphiphilic block copolymer with the number-average molecular weight of 3,000-50,000, wherein the alpha-methyl unsaturated olefinic bond monomer polymer chain segment accounts for 20%-80% of weight of the amphiphilic block copolymer; and the alpha-methyl unsaturated olefinic bond monomer is any one of a methyl methacrylate monomer, an ethyl methacrylate monomer, a methacrylic acid normal propyl acetate monomer, a methacrylic isopropyl ester monomer, an n-butyl methacrylate monomer, an isobutyl methacrylate monomer, a tert-butyl methacrylate monomer, a glycidyl methacrylate monomer, a hydroxyethyl methylacrylate monomer or polyethylene glycol dimethacrylate. The invention further discloses a preparation method of the amphiphilic block copolymer.

Description

technical field [0001] The present invention relates to a block polymer with amphiphilic properties, and also relates to a preparation method of the above-mentioned amphiphilic block polymer. Background technique [0002] The amphiphilic block polymer is composed of a hydrophilic segment and a hydrophobic segment, and the drug-loaded micelle formed by it has a "core-shell" structure. Among them, the hydrophobic core of the micelle can effectively encapsulate the hydrophobic drug, and the hydrophilic shell makes the micelle dissolve in water, so that the micelle can obtain the effect of solubilizing the hydrophobic drug. The use of amphiphilic block polymer micelles as drug delivery carriers not only solubilizes drugs, but also has the advantages of prolonging drug half-life, controlling the particle size of drug-loaded micelles, and enhancing targeting to tumor cells. One of the most promising methods for hydrophobic antitumor drug delivery systems. [0003] Amphiphilic bl...

Claims

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Application Information

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IPC IPC(8): C08F293/00A61K9/107A61K47/34A61K47/32
CPCY02P20/54
Inventor 焦真樊文景王梓屹王秀东
Owner SOUTHEAST UNIV
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