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PH-sensitive biodegradable polyurethane-urea material and preparation method thereof

A polyurethane urea and biodegradation technology, applied in the field of polymer chemistry, can solve the problems of long time consumption and complicated preparation process, and achieve the effects of improving mechanical properties, simple process and avoiding acid inflammation

Active Publication Date: 2018-09-21
烟台研创聚氨酯科技有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the preparation process is cumbersome and time-consuming

Method used

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  • PH-sensitive biodegradable polyurethane-urea material and preparation method thereof
  • PH-sensitive biodegradable polyurethane-urea material and preparation method thereof
  • PH-sensitive biodegradable polyurethane-urea material and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0057] Under the protection of dry nitrogen, 10.0g (5mmol) PLA-PEG-PLA (M n =2000, the mass content of PEG is 22.0%) mixed with 6.30g (30mmol) N,N-di(2-hydroxyethyl)isonicotinamide, added N,N-dimethylformamide (DMF) to dissolve (0.5 g / mL), the temperature of the reaction system was raised to 80°C, and the DMF solution (1.0g / mL) of LBL (35.7mmol) was added dropwise. About 10% solution, 8 times the volume of glacial ether is settled, and the obtained solid is vacuum-dried at 35°C to obtain pH-sensitive biodegradable polyurethane urea;

[0058] Dissolve the solid in the organic solvent chloroform to make a solution with a concentration of 6.0% (g / mL), volatilize it with a polytetrafluoroethylene film at 25°C under normal pressure for 80 hours, remove the film from the film, and then warm it at ordinary times. Vacuum-dried to obtain pH-sensitive biodegradable polyurethane urea film material I, and the drug-loaded film material was prepared in the same way.

Embodiment 2

[0060] Under dry nitrogen protection, 20.0g (10mmol) PCL-PEG-PCL (M n =2000, the mass content of PEG is 26.4%) mixed with 14.70g (70mmol) N,N-bis(2-hydroxyethyl)isonicotinamide, added N,N-dimethylformamide (DMF) to dissolve (0.5 g / mL), the temperature of the reaction system was raised to 85°C, and a DMF solution (1.0 g / mL) of LBL (82.1 mmol) was added dropwise. About 10% solution, 8 times the volume of glacial ether is settled, and the obtained solid is vacuum-dried at 35°C to obtain pH-sensitive biodegradable polyurethane urea;

[0061] Dissolve the solid in the organic solvent chloroform to make a concentration of 5.0% (g / mL), use a polytetrafluoroethylene film to volatilize at 28°C under normal pressure for 90 hours, remove the film from the film, and dry it in vacuum at room temperature , to obtain the pH-sensitive biodegradable polyurethane urea membrane material II, and prepare the drug-loaded membrane material by the same method.

Embodiment 3

[0063] Under the protection of dry nitrogen, 15.0g (5mmol) PLA-PEG-PLA (M n =3000, the mass content of PEG is 43.3%) mixed with 8.40g (40mmol) N,N-di(2-hydroxyethyl)isonicotinamide, adding N,N-dimethylformamide (DMF) to dissolve (0.6 g / mL), the temperature of the reaction system was raised to 90°C, and a DMF solution (1.0 g / mL) of LBL (45.7 mmol) was added dropwise. About 10% solution, 8 times the volume of glacial ether is settled, and the obtained solid is vacuum-dried at 35°C to obtain pH-sensitive biodegradable polyurethane urea;

[0064] Dissolve the solid in the organic solvent chloroform to make a concentration of 6.0% (g / mL), use a polytetrafluoroethylene film to volatilize at 22°C under normal pressure for 75 hours, remove the film from the film, and dry it in vacuum at normal temperature , to obtain the pH-sensitive biodegradable polyurethane urea membrane material III, and prepare the drug-loaded membrane material by the same method.

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Abstract

The invention discloses a pH-sensitive biodegradable polyurethane-urea material and a preparation method thereof. The polyurethane-urea is pH-sensitive biodegradable polyurethane-urea prepared by mixing dihydroxy-terminal polyether ester with N,N-bis(2-ethoxy) 4-pyridinccarbox amide, carrying out chain expansion by using carbamido-containing diisocyanate and purifying; the polyether ester is usedas a main soft segment, a chain segment containing carbamido and urethane group is used as a hard segment and a pyridine ring is positioned on a side chain. The polyurethane-urea has the characteristics of biodegradability, absorbability of a degradation product, pH sensitivity, high expanding and degrading rate in acidic mediums, as well as basically no expansion and low degrading rate in neutraland alkaline mediums; in addition, the pH sensitivity is not basically affected by temperature and can be applied to the field of controlled release as a drug carrier, and further the drug release rate is controlled according to pH values of different parts of an organism. The hard segment formed by carbamido-containing structure diisocyanate contains dense hydrogen bonds, so that the mechanicalproperty of the material is improved.

Description

technical field [0001] The invention belongs to the field of macromolecule chemistry, and in particular relates to a pH-sensitive biodegradable polyurethane urea material and a preparation method thereof. Background technique [0002] Polymer material is a material that can respond to the stimuli of the surrounding environment, and at the same time, it is accompanied by some changes in its own properties. In the 21st century, the application of smart polyurethane has received extensive attention, and this smart polyurethane material has been widely used in the fields of bioseparation, actuators, drug controlled release, and regenerative medicine. The uniqueness of smart polyurethane is not only that subtle stimuli can change its own structure, but also that these changes are reversible, such as the shape of the polymer, surface properties, reaction speed and recognition performance. Stimuli from the external environment can cause these changes, such as: temperature, pH valu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G18/66C08G18/42C08G18/32A61K9/70A61K47/34
CPCA61K9/7007A61K47/34C08G18/3844C08G18/4252C08G18/4277C08G18/6651
Inventor 侯昭升高园园张娜刘小龙
Owner 烟台研创聚氨酯科技有限责任公司
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