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Sugar-containing amphiphilic segmented copolymer and preparation method thereof

A technology of amphiphilic block and copolymer, which is applied in the field of synthesis and preparation of polymer materials, can solve the problems of cumbersome steps of unsaturated sugar-containing monomers, achieve simple polymer grafting means, eliminate synthesis steps and reaction conditions mild effect

Active Publication Date: 2017-01-18
SOUTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] In view of this, the present invention aims to overcome the disadvantages of cumbersome steps in the preparation of unsaturated sugar-containing monomers in the synthesis of traditional sugar-containing polymers, provide a general synthesis method for sugar-containing block copolymers, and propose a combination of ring-opening polymerization, reversible addition- A new method for the preparation of sugar-containing block copolymers by fragmented chain transfer polymerization and pentafluorobenzene active ester-amino reaction, and the preparation of sugar-containing amphiphilic block copolymers

Method used

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  • Sugar-containing amphiphilic segmented copolymer and preparation method thereof
  • Sugar-containing amphiphilic segmented copolymer and preparation method thereof
  • Sugar-containing amphiphilic segmented copolymer and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0032] The preparation method of PCL1 macromolecular chain transfer agent comprises the following steps:

[0033] 1) Take stannous octoate as a catalyst and 4-cyano-4-[(dodecylsulfanylthiocarbonyl)sulfanyl]pentanol as an initiator, add 200 mg of 4-cyano in a glass flask successively -4-[(dodecylsulfanylthiocarbonyl)sulfanyl]pentanol and 5.6 milliliters of ε-caprolactone, the molar ratio of initiator to monomer is 1:100;

[0034] 2) After vacuuming-nitrogen filling-vacuumizing cycle, add 40.5 mg of stannous octoate (dissolved in 2 ml of toluene) catalyst, seal it under nitrogen atmosphere, place it in an oil bath at 110°C for 12 hours, and cool to room temperature to terminate the polymerization;

[0035] 3) adding 10 ml of tetrahydrofuran for dilution, adding the reaction solution dropwise into 200 ml of cold ether solution, filtering and drying to obtain the PCL1 macromolecular chain transfer agent.

Embodiment 2

[0037] The preparation method of PCL2 macromolecular chain transfer agent comprises the following steps:

[0038] 1) Take stannous octoate as a catalyst and 4-cyano-4-[(dodecylsulfanylthiocarbonyl)sulfanyl]pentanol as an initiator, add 200 mg of 4-cyano in a glass flask successively -4-[(dodecylsulfanylthiocarbonyl)sulfanyl]pentanol and 8.4 milliliters of ε-caprolactone, the molar ratio of initiator to monomer is 1:150;

[0039] 2) After vacuuming-nitrogen filling-vacuumizing cycle, add 40.5 mg of stannous octoate (dissolved in 2 ml of toluene in advance) catalyst, seal under nitrogen atmosphere, place in 110 ℃ oil bath for 12 hours, cool to room temperature to terminate polymerization;

[0040]3) adding 10 milliliters of tetrahydrofuran for dilution, adding the reaction solution dropwise into 200 milliliters of cold ether solution, filtering and drying to obtain the PCL2 macromolecular chain transfer agent.

Embodiment 3

[0042] The preparation method of PCL1-PPFA block copolymer comprises the following steps:

[0043] 1) Dissolve 1.3 grams of PCL1 macromolecular chain transfer agent in 8 milliliters of toluene solvent, then add 6.2 milligrams of azobisisobutyrocyanide and 1.8 grams of pentafluorophenyl acrylate in turn, and perform a vacuum-filling-vacuum cycle, Seal under a nitrogen atmosphere, place in a 70°C oil bath for 12 hours, and cool to room temperature to terminate polymerization;

[0044] 2) adding 10 ml of tetrahydrofuran for dilution, adding the reaction solution dropwise into 200 ml of cold ethanol solution, filtering and drying to obtain a PCL1-PPFA block copolymer.

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Abstract

The invention discloses a sugar-containing amphiphilic segmented copolymer and also discloses a preparation method of the sugar-containing amphiphilic segmented copolymer. The preparation method specifically comprises the following steps: firstly, a macromolecular chain transfer agent is prepared by a ring opening polymerization method; then, by a reversible addition-fragmentation chain transfer polymerization method and under the action of the macromolecular chain transfer agent, active monomer unsaturated pentafluorophenyl ester polymerization is initiated to prepare an amphiphilic segmented copolymer; and finally, by an active pentafluorophenyl ester-amino reaction method, the segmented copolymer and a sugar-containing polymer containing an amino group react to generate the sugar-containing amphiphilic segmented copolymer. According to the method, the defect that traditional sugar-containing polymer synthesis has complicated steps for preparation of an unsaturated sugar-containing monomer is overcome; reaction steps of the method are simplified; reaction conditions are mild; and the type of a sugar-containing polymer containing an amino group can be selected. The sugar-containing amphiphilic segmented copolymer of the invention has potential application in the aspects of controlled release of drugs and targeting therapy of tumor.

Description

technical field [0001] The invention belongs to the technical field of polymer material synthesis and preparation, and relates to an amphiphilic sugar-containing block copolymer and a preparation method thereof. Background technique [0002] Glycopolymers refer to polymer materials formed by introducing sugar components into polymer molecular chains through different chemical methods. The sugar components can be various monosaccharides (glucose, galactose, mannose), disaccharides (lactose, maltose) and oligosaccharides (maltoheptaose) (Chem.Rev.2016,116,1673-1692; Prog.Polym .Sci.2016,57,64-102). Sugars are widely distributed in living organisms and play a very important role in the activities of living organisms such as immune response, cell growth, embryo formation and intercellular information transmission. Glycopolymers inherit some of the properties of sugar molecules, and have the characteristics of hydrophilicity, biocompatibility, signal transmission, and pathogen ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G63/08C08F293/00C08F220/22C08F8/00
CPCC08F8/00C08F220/22C08F293/00C08G63/08
Inventor 李宁宁蔡晓燕刘建华李俊志陈久存徐立群
Owner SOUTHWEST UNIV
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