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Polyurethane segmented copolymer containing disulfide bonds and tertiary amine groups as well as preparation method of polyurethane segmented copolymer

A technology of block copolymer and polyurethane, applied in the field of polyurethane, can solve problems such as unreported, and achieve the effect of simple and easy method, good medical application prospect and easy control.

Active Publication Date: 2014-02-26
CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, polyurethane drug carrier materials that can respond rapidly to physiologically relevant pH and redox environment changes have not been reported so far.

Method used

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  • Polyurethane segmented copolymer containing disulfide bonds and tertiary amine groups as well as preparation method of polyurethane segmented copolymer
  • Polyurethane segmented copolymer containing disulfide bonds and tertiary amine groups as well as preparation method of polyurethane segmented copolymer
  • Polyurethane segmented copolymer containing disulfide bonds and tertiary amine groups as well as preparation method of polyurethane segmented copolymer

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0070] Correspondingly, the present invention provides a kind of preparation method of the polyurethane block copolymer described in above-mentioned technical scheme, comprises the following steps:

[0071] Under the action of a catalyst, react diols containing disulfide bonds, diols containing tertiary amines, and diisocyanates in 1,2-dichloroethane for 10 to 60 minutes, and then add polyethylene glycol monomethyl ether to continue the reaction 2~10h, obtain ABA type polyurethane block copolymer,

[0072] The number average molecular weight of the polyethylene glycol monomethyl ether is 500-10000, preferably 1500-8000, more preferably 2000-5000; the diol containing disulfide bonds, diol containing tertiary amine and diol The ratio of the total mass of isocyanate to the mass of polyethylene glycol monomethyl ether is (1~9): (1~9), preferably (3~7): (3~7), more preferably (4~6 ): (4~6); The mass ratio of the diol containing disulfide bond and the diol containing tertiary amine...

Embodiment 1～12

[0088] Add a certain amount of PEG into a dry reaction flask, add anhydrous toluene, and azeotropically remove water at 130°C for 6 hours, then drain the remaining toluene under reduced pressure, and cool to room temperature under nitrogen protection;

[0089] Then add DHDS, HEP, the catalyst dibutyltin dilaurate and an appropriate amount of 1,2-dichloroethane into the reaction flask containing PEG, and stir at 75°C until the solid dissolves;

[0090] Then HDI was added into the reaction flask, and stirred and reacted for 5 hours at 75°C under nitrogen protection;

[0091] The reaction product was settled with ether, and then the obtained solid was dissolved in chloroform, then settled with ether, filtered with suction, and dried to obtain the product.

[0092] The formula of specific raw material monomers is shown in Table 1, and the molecular weight characterization of the polyurethane obtained in Examples 2 to 6 is shown in Table 2.

[0093] To measure the performance of t...

Embodiment 13～21

[0095] Add a certain amount of PEG with a number average molecular weight of 2000 into a dry reaction flask, add anhydrous toluene, and azeotropically remove water at 130°C for 8 hours, then drain the remaining toluene under reduced pressure, and cool under nitrogen protection conditions to room temperature;

[0096] Then add DHDS, TCI-EP, catalyst stannous octoate and appropriate amount of 1,2-dichloroethane into the reaction flask containing PEG, and stir at 75°C until the solid dissolves;

[0097] Then HDI was added into the reaction flask, and stirred and reacted for 5 hours at 75°C under nitrogen protection;

[0098] The reaction product was settled with ether, and then the obtained solid was dissolved in chloroform, then settled with ether, filtered with suction, and dried to obtain the product. (the formula of concrete raw material monomer sees Table 1)

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Abstract

The invention discloses a polyurethane segmented copolymer simultaneously containing disulfide bonds and tertiary amine groups. Active sites can be easily introduced at a main chain and a chain end for molecular modification, the structure and function diversification is realized, and in addition, the multiplex regulation control is easily carried out on the polymer structure. The polyurethane segmented copolymer has good pH sensibility, reduction sensibility and unique amphipathic characteristics, the pH sensitive range is between 5.5 and 7.0, the polyurethane segmented copolymer can simultaneously make fast response to relative physiological pH and oxidation reduction environment change, in addition, materials can form a stable nanometer micellar structure in water, the self-assembly form of the nanometer micellar structure can be changed along with the pH and oxidation reduction environment change, and good medical application prospects are realized. Correspondingly, the invention also provides a preparation method of the polyurethane segmented copolymer, the method is simple and is easy to implement, the control is easy, and the polyurethane segmented copolymer simultaneously containing disulfide bonds and tertiary amine groups is prepared.

Description

technical field [0001] The invention relates to the technical field of polyurethane, more specifically, to a polyurethane block copolymer containing disulfide bonds and tertiary amine groups and a preparation method thereof. Background technique [0002] With the development of nanotechnology, material science, pathology, and cell and molecular biology, the research on anti-tumor drug carriers has also made great progress. Compared with other types of carriers, nanocarriers have a longer circulation time in blood due to their larger hydrodynamic radius, and can preferentially accumulate in pathological areas with leaky vessel walls such as embolism and tumor tissue And keep it for a long time to form passive accumulation (EPR effect), which has some potential advantages for the treatment of cancer. In recent decades, although scholars at home and abroad have done a lot of research on nanocarriers and designed many drug delivery systems, there are still few products that are...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G18/66C08G18/48C08G18/32A61K47/34A61K48/00
Inventor 贺超良于双江成一龙肖春生丁建勋庄秀丽陈学思
Owner CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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