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PH sensitive medical polyurethane urea material and preparation method thereof

A polyurethane urea and sensitive technology, applied in the field of biological material preparation, can solve the problems of toxicity, use restriction, complex preparation method, etc., and achieve the effects of low cost, avoiding the generation of thrombus, and simple process

Active Publication Date: 2018-09-14
科莱新材料技术(广州)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method is a temperature- and pH-responsive polyurethane hydrogel prepared by directional polymerization, and the synthetic polyurethane has a short time to reach swelling equilibrium in deionized water, but its preparation method is complicated, and the alkali-sensitive functional groups it carries Dihydric alcohols are aromatic compounds, and their degradation products have certain toxicity to organisms, and their medical use is limited.

Method used

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  • PH sensitive medical polyurethane urea material and preparation method thereof
  • PH sensitive medical polyurethane urea material and preparation method thereof
  • PH sensitive medical polyurethane urea material and preparation method thereof

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preparation example Construction

[0067] The preparation method of LBL is: under the protection of dry nitrogen and mechanical stirring, add 1,4-butanediamine dropwise to L-lysine diisocyanate (-NCO:-NH 2 =8:1, molar ratio), after reacting at room temperature for 2h, add four times the volume of n-hexane to the reaction product, after stirring evenly, obtain a white solid by suction filtration, wash with n-hexane repeatedly until the filtrate IR detects that there is no -NCO absorption Peak (2270cm -1 ), vacuum-dried to constant weight to obtain white powder LBL.

[0068] LBL's 1 H NMR structure characterization results:

[0069] 1 H NMR (DMSO-D6, 400MHz, ppm): 1.27-1.32 (m, 10H, CH 3 CH 2 and C H 2 CH 2 CHNCO), 1.52-1.55(m,8H, CH 2 CH 2 NH),1.75(q,4H, CH 2 CHNCO),3.08-3.16(t,8H, CH 2 NH), 4.08-4.15 (m, 6H, CH-NCO and CH 3 C H 2 ), 5.95-6.04 (br, N H ).

Embodiment 1

[0071] Under the protection of dry nitrogen, 5.370g (30mmol) terminal dihydroxypyridine compound (VP-(OH) 2 ) with 5.0g (5mmol) polyethylene glycol (PEG, M n =1000) were mixed, N,N-dimethylformamide (DMF) was added to dissolve (0.5g / mL), the temperature of the reaction system was raised to 80°C, a DMF solution (1.0g / mL) of LBL (35.7mmol) was added dropwise, After the dropwise addition, keep the temperature and continue the reaction for 4.0 h, lower to room temperature, then add DMF to make a solution with a concentration of about 10%, settle with 8 times the volume of glacial ether, and dry the obtained solid under vacuum at 35°C.

[0072] Dissolve the solid in the organic solvent chloroform to make a concentration of 6.0% (g / mL), use a polytetrafluoroethylene film to volatilize at 25°C under normal pressure for 80 hours, remove the film from the film, and dry it in vacuum at room temperature , to obtain the pH-sensitive medical polyurethane urea film material I, and prepare ...

Embodiment 2

[0074] Under the protection of dry nitrogen, 8.950g (50mmol) terminal dihydroxypyridine compound (VP-(OH) 2 ) with 5.0g (5mmol) polyethylene glycol (PEG, M n =1000) were mixed, N,N-dimethylformamide (DMF) was added to dissolve (0.5g / mL), the temperature of the reaction system was raised to 85°C, a DMF solution (1.0g / mL) of LBL (56.1mmol) was added dropwise, After the dropwise addition, keep the temperature and continue the reaction for 3.5 h, lower to room temperature, then add DMF to make a solution with a concentration of about 10%, settle with 8 times the volume of glacial ether, and dry the obtained solid under vacuum at 35°C.

[0075] Dissolve the solid in the organic solvent chloroform to make a concentration of 5.5% (g / mL), use a polytetrafluoroethylene film to volatilize at 25°C under normal pressure for 80 hours, remove the film from the film, and dry it in vacuum at normal temperature , to obtain pH-sensitive medical polyurethane urea membrane material II, and prepa...

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Abstract

The invention discloses a pH sensitive medical polyurethane urea material and a preparation method thereof. The preparation method comprises the following steps: mixing a terminal dihydroxypyridine compound and a double-end hydroxyl polyethylene glycol to obtain polyurethane urea, and dissolving by adding N,N-dimethylformamide, carrying out chain extension in the presence of urea-containing diisocyanate, and purifying to obtain pH-sensitive polyurethane urea, wherein diisocyanate is L-lysine diisocyanate-1,4-butylenediamine-L-lysine diisocyanate. The pyridine group on a side chain of polyurethane urea is Lewis base, which is able to decompose hydrogen bonds in a polyurethane urea network under acidic conditions, resulting in discontinuous volume expansion of material. According to the invention, H<+> is removed under neutral or alkaline conditions, and N on a pyridine ring and NH on carbamate or ureido form a hydrogen bond, approximating a network structure, so that the polyurethane urea molecular chain shrinks and the swelling degree decreases remarkably. Therefore, by controlling the change of the pH of a medium, the degree of swelling of polyurethane urea can be effectively controlled.

Description

technical field [0001] The invention belongs to the technical field of biological material preparation, in particular to the field of intelligent medical polymer materials, in particular to a preparation method of pH-sensitive medical polyurethane urea. Background technique [0002] Smart polymer material is a material that can respond to the stimuli of the surrounding environment and at the same time, change some of its 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, s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G18/78C08G18/48C08G18/32A61K47/34
CPCA61K47/34C08G18/3868C08G18/4833C08G18/7812
Inventor 侯昭升刘路路原栎潼张鋆肖铭慧
Owner 科莱新材料技术(广州)有限公司
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