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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 effect of simple and easy method, easy control and good pH sensitivity

Active Publication Date: 2013-01-16
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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Effect test

preparation example Construction

[0062] Correspondingly, the present invention provides a method for preparing a polyurethane block copolymer, including the following steps:

[0063] Under the action of a catalyst, the diol containing 1,2-disulfide heterocycle, the diol containing tertiary amine, and the diisocyanate are pre-reacted in an organic solvent, and then reacted with polyethylene glycol monomethyl ether to obtain polyurethane intercalation. A segment 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, diols containing 1,2-disulfide heterocycles, tertiary amine-containing diols and diisocyanates as raw materials. 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-disulfide heterocycle is trans-4,5-dihydroxy-1,2-dit...

Embodiment 1~12

[0086] Add a certain amount of PEG with a molecular weight of 2000 to a dry reaction flask, add anhydrous toluene, and azeotropically remove water at 130°C for 6 hours, drain the remaining toluene under reduced pressure, and cool to room temperature under nitrogen protection ;

[0087] Then add DHDT, HEP, catalyst dibutyl tin dilaurate and appropriate amount of 1,2-dichloroethane into the reaction flask containing PEG, and stir at 75°C until the solid is dissolved;

[0088] Then add HDI into the reaction flask, stir and react for 5 hours at 75°C under nitrogen protection;

[0089] The reaction product was settled with ether, and then the obtained solid was dissolved in CHCl 3 After sedimentation with ether, suction filtration, and drying, a polyurethane block copolymer is obtained.

[0090] The specific raw material monomer formula is shown in Table 1, and the molecular weight characteristics of the polyurethane obtained in Examples 1 to 4 are shown in Table 2.

[0091] Perform nuclear...

Embodiment 13

[0094] Add a certain amount of PEG with a molecular weight of 500 to a dry reaction flask, add anhydrous toluene, and azeotropically remove water at 130°C for 8 hours, 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 is dissolved;

[0096] Then add TCDI to the reaction flask, stir and react 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, and then settled with ether, filtered with suction, and dried to obtain a polyurethane block copolymer. The specific raw material monomer formula 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, a preparation method thereof, and a preparation method of nano hydrogel. Background technique [0002] Nanocarriers (10~200nm) have "EPR effect". Compared with other types of carriers, they have a longer circulation time in the blood and can preferentially locate in pathological areas with leaks in the blood vessel wall (such as embolism and tumor tissue). Middle) Aggregate and retain for a long time to form passive accumulation, which has many potential advantages for cancer treatment. Because nanocarriers need to withstand multiple environmental stimuli, such as pH, redox environment, etc., during the process of entering tumor cells through blood circulation, a smart drug controlled release system that is sensitive and responsive to the physiological environment is designed to achieve drug interaction The targeted release of tumors is of great significanc...

Claims

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Application Information

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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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