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Method for preparing dendritic macromolecule of polyester

A dendritic and macromolecular technology, applied in the field of polymer material preparation, can solve the problems of loss of dendritic macromolecules, cumbersome purification steps, low yield, etc., and achieve faster synthesis speed, better biocompatibility, improved quality and The effect of using security

Inactive Publication Date: 2009-12-02
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Defective molecules can be removed by preparative HPLC, but a large amount of dendrimers will be lost, resulting in low yields
Although, some synthetic methods with simple steps have been reported (Malkoch M, Malmstroem E, Hult A. Rapid and Efficient Synthesis of Aliphatic Ester Dendrons and Dendrimers. Macromolecules, 2002, 35: 8307-8314; Goodwin AP, Lam SS, Fréchet JMJ .Rapid, Efficient Synthesis of Heterobifunctional BiodegradableDendrimers.J.Am.Chem.Soc.2007,129:994-6995), but it still involves protection / deprotection process and cumbersome purification steps

Method used

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  • Method for preparing dendritic macromolecule of polyester
  • Method for preparing dendritic macromolecule of polyester
  • Method for preparing dendritic macromolecule of polyester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1 Preparation of polyester dendrimers using chemical reaction kinetics asymmetry monomer pair MAEA and cysteamine

[0028] (1) Synthesis of monomer methacryloxy ethyl acrylate (MAEA)

[0029] Dissolve 78g (0.60mol) of hydroxyethyl methacrylate and 100ml (0.72mol) of triethylamine in 400ml of CH at 0°C 2 Cl 2 52.4ml (0.66mol) of acryloyl chloride was added dropwise, stirred overnight, and the precipitate was filtered off. The filtrate was washed 3 times with 150ml of water each time, and the organic phase was dried with sodium sulfate and spin-dried to obtain 104.2g of MAEA with a yield of 94.3 %.

[0030] (2) Synthesis of the first generation polyester dendrimers (A-G 1 )

[0031] Add 0.95g (10.8mmol) of 1,4-butanediamine (A) and 10g (53.9mmol) of MAEA into the flask, stir at room temperature overnight, then react at 70°C for 48h, and wash the reaction solution with n-hexane three times, each time 10ml of n-hexane was dried under vacuum to obtain the produc...

Embodiment 2

[0042] Except adopting ethylenediamine (B) to replace 1,4-butanediamine (A) to react with MAEA in step (2), other operations are the same as in Example 1, and the fourth generation polyester dendrimer B-G is prepared 4 .

Embodiment 3

[0044] Except adopting 1,6-hexamethylenediamine (C) to replace 1,4-butanediamine (A) to react with MAEA in step (2), other operations are the same as in Example 1, and the fourth-generation polyester dendrimer is prepared Shaped macromolecule C-G 4 .

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Abstract

The invention discloses a method for synthesizing a dendritic macromolecule of polyester. The method comprises the following steps: reacting polyamine or polyalcohol and an ABx type asymmetrical monomer, repeatedly and alternately adding a CDy type asymmetrical monomer and the ABx type asymmetrical monomer, and preparing the dendritic macromolecule of polyester by the selective chemical reaction of the CDy type asymmetrical monomers and the ABx type asymmetrical monomers; selecting methacryloxypropyl ethyl acrylate or methacryloxypropyl propyl acrylate as the ABx type asymmetrical monomer, and cysteamine as the CDy type asymmetrical monomer; or selecting methacrylic acid isocyano ethyl ester as the ABx type asymmetrical monomer, and amino glycerol as the CDy type asymmetrical monomer. The method has the advantages of easy synthesis, simple product purification and the like; and the synthesized dendritic macromolecule of polyester can be biologically degraded and has good biocompatibility, and can be used as a biomedical material.

Description

technical field [0001] The invention belongs to the technical field of polymer material preparation, and in particular relates to a preparation method of biomedical degradable polyester dendrimers. Background technique [0002] Due to its precise three-dimensional nano-molecular structure, dendrimers can be used in the field of medicine as a nanotechnology platform, and can be used as drug and gene delivery carriers (such as: Tekade RK, KumarPV, Jain NK.Dendrimers in Oncology: An Expanding Horizon.Chem .Rev.2009, 109:49-87; N. Malik et al. disclosed an anti-tumor dendrimer drug delivery system in Chinese patent application No. 01823749.5). On the one hand, the cavity inside the dendritic macromolecule can be used for drug encapsulation (Hecht S, Fréchet, JMJ. Dendritic Encapsulation of Function: Applying Nature's Site Isolation Principle from Biomimetics to Materials Science. Angew. Chem. Int. Ed. Eng .2001,40:74-91); on the other hand, a large number of functional groups o...

Claims

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Application Information

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IPC IPC(8): C08G63/688C08G63/685C08G63/78C08G73/00C08G75/00
Inventor 申有青唐建斌孙晓明
Owner ZHEJIANG UNIV
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