Polyurethane block copolymer, preparation method thereof and preparation method of polyurethane block copolymer nano hydrogel

A technology of block copolymer and nano-hydrogel, which is applied in the field of polyurethane and achieves the effects of simple and easy method, good stability and good medical application prospect.

Active Publication Date: 2014-07-02
CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, polyurethane nanohydrogel drug carrier materials that can respond rapidly to physiologically relevant pH and redox environment changes have not been reported yet.

Method used

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  • Polyurethane block copolymer, preparation method thereof and preparation method of polyurethane block copolymer nano hydrogel
  • Polyurethane block copolymer, preparation method thereof and preparation method of polyurethane block copolymer nano hydrogel
  • Polyurethane block copolymer, preparation method thereof and preparation method of polyurethane block copolymer nano hydrogel

Examples

Experimental program
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preparation example Construction

[0062] Correspondingly, the invention provides a kind of preparation method of polyurethane block copolymer, comprises the following steps:

[0063] Under the action of a catalyst, the diol containing 1,2-dithioheterocycle, the diol containing tertiary amine, and diisocyanate are pre-reacted in an organic solvent, and then reacted with polyethylene glycol monomethyl ether to obtain polyurethane embedded A block copolymer, the polyurethane block copolymer includes an A block represented by formula (I) and a B block represented by formula (II).

[0064] The present invention uses polyethylene glycol monomethyl ether, diol containing 1,2-dithioheterocycle, diol containing tertiary amine and diisocyanate as raw materials, and the number average molecular weight of the polyethylene glycol monomethyl ether is preferably 500~10000, more preferably 1500~8000, most preferably 2000~5000;

[0065] The diol containing 1,2-dithioheterocycle is trans-4,5-dihydroxyl-1,2-dithiane; the diol c...

Embodiment 1~12

[0086] Add a certain amount of PEG with a molecular weight of 2000 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. ;

[0087] Then add DHDT, HEP, 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;

[0088] Then HDI was added into the reaction flask, and stirred and reacted for 5 hours at 75°C under nitrogen protection;

[0089] The reaction product was settled with ether, and the resulting solid was dissolved in CHCl 3 , then settle with diethyl ether, filter with suction, and dry to obtain a polyurethane block copolymer.

[0090] The formula of specific raw material monomers is shown in Table 1, and the molecular weight characterization of the polyurethane obtained in Examples 1-4 is shown in Table ...

Embodiment 13

[0094] Add a certain amount of PEG with a molecular weight of 500 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 to room temperature under nitrogen protection. ;

[0095] Then add DHDT, HEP, 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;

[0096] Then TCDI was added into the reaction flask, and stirred and reacted for 5 hours at 75° C. under nitrogen protection;

[0097] 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 a polyurethane block copolymer. The formulation of specific raw material monomers is shown in Table 1.

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Abstract

The invention provides a polyurethane block copolymer, which comprises a block A shown as a formula (I) and or a formula (III) and a block B shown as a formula (II). Since the polyurethane block copolymer simultaneously contains a tertiary amine group and a 1, 2-dithioheterocyclic ring, the polyurethane block copolymer has good pH (potential of hydrogen) sensitivity, good reduction sensitivity and unique amphipathic characteristic, the pH sensitive interval is between 5.5 and 7.0, and responses can be quickly made to both physiologically related pH changes and oxidation-reduction environment changes. The invention additionally provides a preparation method of the polyurethane block copolymer, wherein the preparation method of the polyurethane block copolymer is simple, feasible and easy to control. The invention additionally provides a preparation method of polyurethane block copolymer nano hydrogel. Since the molecular chain of the polyurethane block copolymer contains the 1, 2-dithioheterocyclic ring, inter molecular chain linkage can happen to obtain nano hydrogel. The nano hydrogel has the advantages that the self-assembling form can be changed with pH and oxidation-reduction environment, the stability is high and the medical application prospect is good.

Description

technical field [0001] The invention relates to the field of polyurethane, in particular to a polyurethane block copolymer, its preparation method and its nano hydrogel preparation method. Background technique [0002] Nanocarriers (10-200nm) have the "EPR effect", which has a longer circulation time in the blood compared with other types of carriers, and can preferentially treat pathological areas with leaks in the vessel wall (such as: embolism and tumor tissue) Middle) accumulate and retain for a long time, forming passive accumulation, which has many potential advantages for the treatment of cancer. Since nanocarriers need to withstand multiple environmental stimuli during the process of entering tumor cells through the blood circulation, such as pH, redox environment, etc., therefore, it is necessary to design an intelligent drug controlled release system that is sensitive to the physiological environment to realize the drug on the tumor cells. Tumor targeted release i...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G18/66C08G18/48C08G18/32C08J3/075A61K47/34
Inventor 贺超良于双江庄秀丽陈学思
Owner CHANGZHOU INST OF ENERGY STORAGE MATERIALS &DEVICES
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