Polyethylene glycol dendritic polymers and preparation method thereof

A technology based on polyethylene glycol and polyethylene glycol, which is applied in the chemical industry, can solve the problems of limited combined use, waste of package load function, and non-utilization of hydrophobic space, and achieves the effect of mild reaction conditions and low cost

Inactive Publication Date: 2012-07-25
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0009] Most of the existing dendritic polymers exhibit hydrophobic properties, which limits their combined use with a large number of hydrophilic and strongly polar drugs. Although the surface modification of polyethylene glycol can solve the problem of grafting, its internal hydrophobicity The space is not utilized, and the unique package loading function of dendrimers is wasted

Method used

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  • Polyethylene glycol dendritic polymers and preparation method thereof

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Effect test

Embodiment 1

[0038] Using PEG200, ethyl acrylate (abbreviation: EA) and ethylenediamine as raw materials, methanol as the catalyst and solvent for the addition reaction to prepare PEG dendrimers, the preparation method is as follows:

[0039] (1) Preparation of branch unit: Dissolve 2.00g of PEG200 in 20mL of tetrahydrofuran (abbreviation: THF), add 6.00g of EA, after stirring evenly, add 100mg of Novozyme 435, and react for 48h under stirring at 50°C. After the reaction, filter The enzyme was removed, the filtrate was distilled under reduced pressure to remove the solvent, excess EA and by-product ethanol, the remaining liquid was separated by column chromatography, and the eluent of petroleum ether / ethyl acetate was eluted to obtain the product as PEG200 diacrylate, pale yellow and transparent Liquid, the average molecular weight is 308g / mol;

[0040](2) Preparation of the first generation polyethylene glycol dendrimer (G1): Dissolve 3.08 g of PEG200 diacrylate in 10 mL of methanol, diss...

Embodiment 2

[0050] Using PEG400, methyl acrylate (referred to as: MA) and 1,3-propanediamine (hereinafter referred to as: propylene diamine) as raw materials, potassium tert-butoxide as the catalyst for the addition reaction to prepare PEG dendrimers, the preparation method is as follows :

[0051] (1) Preparation of branch unit: Dissolve 4.00g PEG400 in 25mL THF, add 5.16g MA, stir evenly, add 250mg Novozyme 435, and react at 50°C for 48h under stirring conditions. After the reaction, the enzyme is removed by filtration, and the filtrate is reduced The solvent, excess MA and by-product methanol were removed by pressure distillation, the remaining liquid was separated by column chromatography, and the eluent of petroleum ether / ethyl acetate was eluted to obtain the product PEG400 diacrylate, pale yellow transparent liquid, and the average molecular weight was 508g / mol;

[0052] (2) Preparation of the first generation polyethylene glycol dendrimer (G1): Dissolve 5.08g PEG400 diacrylate in...

Embodiment 3

[0062] Using PEG600, vinyl acrylate (abbreviation: VA) and 1,4-butanediamine (hereinafter referred to as: butanediamine) as raw materials, triethylamine as the catalyst for the addition reaction to prepare PEG dendrimers, the preparation method is as follows:

[0063](1) Preparation of branch unit: Dissolve 6.00g PEG600 in 25mL THF, add 5.88g VA, stir evenly, add 250mg Novozyme 435, and react at 50°C for 48h. The solvent, excess VA and by-product acetaldehyde were distilled off, the remaining liquid was separated by column chromatography, and the eluent of petroleum ether / ethyl acetate was eluted to obtain the product PEG600 diacrylate, pale yellow transparent liquid with an average molecular weight is 708g / mol;

[0064] (2) Preparation of the first generation polyethylene glycol dendrimer (G1): Dissolve 7.08g PEG600 diacrylate in 10mL THF, take 0.088g butanediamine and 0.404g triethylamine and dissolve in 1mL THF, stirring conditions The THF solution of butanediamine was slo...

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Abstract

The invention discloses polyethylene glycol dendritic polymers and a preparation method thereof. The polyethylene glycol dendritic polymers are prepared with organic diamine as an initiation core, polyethylene glycol and acrylate as repeated branching units, and double bond or primary amine as a surface functional group. The invention also prepares different algebraic polyethylene glycol dendritic polymers by an enzyme-catalyzed transesterification and then a Michael addition reaction with polyethylene glycol, acrylate and primary amine as starting monomers. The prepared polyethylene glycol dendritic polymers have large cavity inside the molecules which can imbed other small molecules such as drug molecules and the like, and a large number of functional groups on the molecular surface canreact with other molecules. The reaction raw materials are safe and non-toxic, and can be excluded from the human bodies quickly. The preparation method adopting the enzyme-catalyzed transesterification and the Michael addition reaction is mild in reaction conditions, green and environment-friendly, low in cost and easy to realize industrialization.

Description

technical field [0001] The invention belongs to the technical field of chemical industry, relates to a polymer and its preparation technology, in particular to a polyethylene glycol dendritic polymer and a method for preparing the polymer by using enzyme-catalyzed reaction and Michael addition reaction. Background technique [0002] Dendrimer is a kind of nonlinear polymer with highly branched structure. Its structure has excellent geometric symmetry, and the volume and shape of molecules can be precisely controlled. Due to the unique structure of dendritic polymers, it has a series of unique physical and chemical properties such as low viscosity, high rheology, good solubility and a large number of terminal functional groups that traditional linear polymers do not have. It is used in biomedicine and advanced materials. Design and other fields have broad application prospects. [0003] And the dendrimers that have been successfully prepared at present still have certain def...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G83/00A61K47/34
Inventor 文秀芳谢倩红皮丕辉蔡智奇徐守萍程江杨卓如
Owner SOUTH CHINA UNIV OF TECH
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