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Stimulation sensitive multifunctional polyisocyanate with active groups

A polyisocyanate and active group technology, applied in the field of polyisocyanate, can solve the problem of no multi-functional polyisocyanate, etc., and achieve the effect of wide application

Active Publication Date: 2016-05-25
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But so far there is no report on the stimulus-sensitive multifunctional polyisocyanate

Method used

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  • Stimulation sensitive multifunctional polyisocyanate with active groups
  • Stimulation sensitive multifunctional polyisocyanate with active groups
  • Stimulation sensitive multifunctional polyisocyanate with active groups

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] In this example, the stimulus-sensitive multifunctional polyisocyanate I with active groups was synthesized.

[0026] Dissolve 14.5 g of cystine dimethyl ester in 400 ml of ethyl acetate, and add 10.7 g of triphosgene under nitrogen protection, react at room temperature for 1 hour, and then heat to reflux for 4 hours. After the reaction solution was cooled, it was washed twice with dilute hydrochloric acid, and once with saturated sodium chloride solution and distilled water. The organic phase was dried over anhydrous magnesium sulfate for 4 hours, filtered with suction and concentrated under reduced pressure. The structural formula of the product obtained is:

[0027]

[0028] The infrared spectrum data are as follows:

[0029] FTIR (KBr, cm -1 ): 2957 (s, νCH), 1441 (m, δCH), 2272 (s, vN=C=O), 1746 (s, vC=O).

[0030] The H NMR spectrum data are as follows:

[0031] 1 HNMR (400MHz, CDCl 3 ): δ4.40(q, J=4.2, NCO-CH-, 2H), 3.86(s, CH 3 O-,6H),3.20(dd,J=4.2,9....

Embodiment 2

[0035] In this example, the stimulus-sensitive multifunctional polyisocyanate II with active groups was synthesized.

[0036] Dissolve 8.41 g of dibenzyl homocystine in a mixed solvent of 200 ml of dichloromethane and 200 ml of saturated aqueous sodium bicarbonate solution, cool to 0°C and vigorously stir for 10 minutes. Then the stirring was stopped, and 41 milliliters of phosgene in toluene (1.93 moles per liter) was injected into the organic phase, and stirred for 10 minutes under ice-bath cooling. The reaction solution was layered, the organic phase was washed twice with 0.5 mol per liter of brine, once with distilled water, and the aqueous phase was backwashed once with dichloromethane. After the organic phases were combined, they were dried with anhydrous sodium sulfate for 10 hours, and decompressed after suction filtration. concentrate. The structural formula of the product obtained is:

[0037]

[0038] The infrared spectrum data are as follows:

[0039] FTIR (K...

Embodiment 3

[0043] In this example, the stimulus-sensitive multifunctional polyisocyanate III with active groups was synthesized.

[0044] Take 4.4 g of N,N'-di-tert-butoxycarbonyl-L-cystine and dissolve it in 50 ml of dichloromethane, add 4.33 g of N,N'-dicyclohexylcarbodiimide and 4.05 g of 1 -Hydroxybenzotriazole, then add 1.38 g of propargylamine, naturally return to room temperature and react for 24 hours. After the reaction was complete, the precipitate was removed by filtration, the product was evaporated to dryness and dissolved in ethyl acetate, washed three times with saturated sodium bicarbonate solution, once each with saturated sodium chloride solution and distilled water, and dried overnight with anhydrous magnesium sulfate. After suction filtration, the filtrate was concentrated under reduced pressure and recrystallized from ethyl acetate. The dried crystals were dissolved in 20 ml of dichloromethane, 20 ml of trifluoroacetic acid was added under ice-cooling, stirred at ro...

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Abstract

The invention discloses stimulation sensitive multifunctional polyisocyanate with active groups. The stimulation sensitive multifunctional polyisocyanate is characterized in that the structural general formula of the polyisocyanate is shown as the accompanying drawing, wherein in the formula, A is a stimulation sensitive group; R1 and R2 are compound groups which have 1 to 20 carbon atoms and contain or do not contain active groups; the R1 and the R2 can be identical or can be different; the R1 and the R2 at least comprise one active group. The polyisocyanate provided by the invention comprises pH, oxidization, reduction, enzyme or photosensitive groups; a lateral chain contains active groups such as ester groups, azide groups, alkynyls, thiazolinyls, halohydrocarbon groups, sulfurous groups, tertiary amino groups or isocyanate groups, so that the polyisocyanate can meet the use requirements of different occasions; the intelligent polymer materials capable of making response or being degradated in various stimulation environments can be obtained; various active sites can be introduced at polymer side chains; the further functional modification potential is given to the materials; therefore wide application prospects are realized in the fields of functional polymer materials and biomedical materials.

Description

technical field [0001] The invention belongs to the technical field of polyisocyanates, in particular to a stimulus-sensitive multifunctional polyisocyanate with active groups. Background technique [0002] Stimulus-sensitive polymer materials are a new type of smart materials, which can sense and respond to changes in the surrounding environment. Compared with ordinary functional materials, they have unique functions such as feedback, bionics and information transmission. When the environment such as external temperature, pressure, pH, electromagnetic field, light and redox potential changes, the molecular structure, phase behavior, assembly behavior, mechanical properties and other properties of such polymers will change accordingly. Therefore, in biosensors, Tissue engineering, artificial muscles, drugs and gene delivery have broad application prospects. Especially in the field of sustained and controlled drug release, because the microenvironment of the lesion site is s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/57C07C323/60C07C265/04C07C391/00C07C323/41C07D317/34C08G18/77C08G18/81
CPCC07C265/04C07C323/41C07C323/57C07C323/60C07C391/00C07D317/34C08G18/775C08G18/8133
Inventor 丁明明汪锐傅强谭鸿张琴李洁华
Owner SICHUAN UNIV
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