Preparation method of double-stimulation response type polyurethane micelle

A dual-stimuli-responsive, polyurethane technology, applied in the field of environment-responsive polymer material preparation, to achieve good pH response characteristics and temperature-sensitive characteristics, excellent biocompatibility and biodegradability effects

Active Publication Date: 2019-12-10
QILU UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, the existing modified polyurethane materials cannot have both pH responsiveness and temperature sensitivity on the basis of excellent biocompatibility and biodegradability.

Method used

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  • Preparation method of double-stimulation response type polyurethane micelle
  • Preparation method of double-stimulation response type polyurethane micelle
  • Preparation method of double-stimulation response type polyurethane micelle

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] The preparation of embodiment 1 initiator

[0044] 1) Dissolve 0.3 mol of 1,4-butanediol (BDO) and 5 mL of triethylamine (TEA) in 40 mL of tetrahydrofuran, place in an ethanol bath at -10°C and stir for 10 minutes to obtain solution A.

[0045] 2) Dissolve 0.01 mol of 2-bromoisobutyryl bromide (BIBB) in 10 mL of tetrahydrofuran and place it in an ethanol bath at -10°C for 3 minutes; obtain solution B.

[0046] Then slowly drop the solution B into the solution A, and control the completion time of the dropping at about 30 minutes, and stir for 12 hours to react.

[0047] 3) After the reaction, the precipitate was removed by filtration, and the filtrate was rotary evaporated at 40°C to remove THF to obtain a light yellow liquid.

[0048] 4) Use CH 2 Cl 2 Extract light yellow liquid, wash three times with distilled water, anhydrous MgSO 4 Dry and rotary evaporate at 40°C to obtain the crude product as light yellow liquid.

[0049] 5) The crude product was separated an...

Embodiment 2

[0050] The preparation of embodiment 2 capping agent (HO-PDMA)

[0051] Prepare a capping agent with a molecular weight of 9000:

[0052] 1) Dissolve 0.0008 mol BDO-BiB, 0.05 mol monomer dimethylaminoethyl methacrylate (DMAEMA) and 0.0008 mol ligand methyldiethylenetriamine (PMDETA) in 10 mL N,N-dimethylformamide (DMF) under nitrogen gas and stirred at room temperature for 30 min.

[0053] 2) Add 0.0008 mol cuprous bromide (CuBr) into the reaction solution, continue to flow nitrogen and stir for 15 minutes.

[0054] 3) Stir and react the above stirred reaction solution in an oil bath at 50°C for 8 hours.

[0055] 4) After the reaction was completed, 10 mLTHF and 10 drops of methanol were added to the obtained reaction liquid, and it became clear.

[0056] 5) The reaction solution was separated by column chromatography to remove copper ions in the reaction solution, and the reaction solution was separated with THF and CH 3 The mixed solution of OH with a volume ratio of 20:...

Embodiment 3

[0062] The preparation of embodiment 3 vanillin acetal compound

[0063] 1) Mix 12 mmol vanillin, 15.6 mmol trimethylolethane and 0.12 mmol catalyst p-toluenesulfonic acid hydrate ( p -TsOH) was dissolved in 15 mL tetrahydrofuran (THF), and stirred at 90 °C under reflux for 12 h.

[0064] 2) After the reaction, THF was removed by rotary evaporation at 40°C to obtain a concentrated crude product.

[0065] 3) Cool the concentrated solution to room temperature, and carry out column chromatography separation and purification. The eluent used is a mixture of petroleum ether: ethyl acetate with a volume ratio of 2:1. After rotary evaporation at 40°C, it is vacuum-dried to obtain 2.21 g vanillin acetal compound, namely vanillin acetal; yield 78.1%.

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Abstract

The invention discloses a preparation method of a double-stimulation response type polyurethane micelle. The preparation method comprises the following steps: preparation of an initiator, preparationof an end capping agent, preparation of a vanillin acetal compound, preparation of end-capped polyurethane and preparation of a polyurethane micelle solution. The end-capped pH and temperature double-response type multi-block polyurethane micelle is successfully prepared by combination of technologies of preparing the hydrophilic temperature-sensitive end-capping agent by atom transfer radical polymerization, introducing amphiphilic segments into a polyurethane chain to form micelles and the like. The prepared polyurethane micelle has excellent biocompatibility and biodegradability, and meanwhile has a pH response characteristic and a temperature sensitivity characteristic.

Description

technical field [0001] The invention belongs to the field of preparation of environment-responsive polymer materials, and in particular relates to a preparation method of dual-stimuli-responsive polyurethane micelles. Background technique [0002] Polyurethane (PU) is a general term for a class of high molecular polymers containing carbamate groups (-NH-COO-) in the main chain structure of macromolecules. It generally consists of two parts, a hard segment and a soft segment. The hard segment is composed of The soft segment is composed of polyisocyanate and chain extender, and polyol. Due to its good physical and mechanical properties, polyurethane can be used to manufacture synthetic leather, elastomers, coatings, foam plastics, adhesives, waterproof materials and flame retardants, etc. In addition, polyurethane also has good biocompatibility and biodegradability. [0003] pH responsiveness means that due to changes in environmental pH, the responsive groups introduced on ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G18/73C08G18/28C08G18/32C08J3/03C08L75/04
CPCC08G18/2815C08G18/3218C08G18/73C08J3/03C08J2375/04
Inventor 张海涛赛福涛魏康曲建波王建勇
Owner QILU UNIV OF TECH
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