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A β-cyclodextrin polyrotaxane with accurate intercalation amount, preparation method and application thereof

A technology of cyclodextrin and polyrotaxane, which is applied in the field of supramolecular polymers, can solve the problems of long reaction routes, differences in cavity adaptability, and lack of widespread attention, and achieve a wide range of options, easy degradation, and abundant The effect of structure type

Active Publication Date: 2022-05-17
BEIJING INSTITUTE OF TECHNOLOGYGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the long reaction route, the final α-CD[3]PR yield is low, so far this route has not attracted widespread attention
The inclusion of β-CD with ferrocene and other substances is mostly limited to the field of small molecules or polymer side group modification, and β-CD has been proved to be difficult to form stable with polymers such as PEG due to the difference in cavity adaptability. PR structure

Method used

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  • A β-cyclodextrin polyrotaxane with accurate intercalation amount, preparation method and application thereof
  • A β-cyclodextrin polyrotaxane with accurate intercalation amount, preparation method and application thereof
  • A β-cyclodextrin polyrotaxane with accurate intercalation amount, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] A preparation method of β-CD[3]PR, the method steps are as follows:

[0083] (1) In the reaction vessel, add 1 part of PEG1000, 8.0 parts of CDI and dry THF equivalent to 8 times the mass of PEG1000, mix well under nitrogen protection, and react at 25°C for 24h. Add 40 parts of ethylenediamine, continue to react at 25°C for 24h under nitrogen protection, concentrate the obtained solution by rotary evaporation, add dichloromethane equivalent to 15 times PEG1000 parts by mass, mix well, pour into the liquid separator, and then add equivalent to 1000 parts by mass of PEG. 0.2 times the volume of dichloromethane saturated brine was fully shaken for washing, and after standing for 5 min, the organic phase was separated, and the washing was repeated 4 times. Add 20 parts of anhydrous sodium sulfate and shake well, filter the retained liquid phase after 5 minutes, evaporate and concentrate, then precipitate in 50 parts of glacial ether, collect the precipitate and vacuum dry t...

Embodiment 2

[0098] A preparation method of β-CD[3]PR, the method steps are as follows:

[0099] (1) In the reaction vessel, add 1 part of PEG2000, 10.0 parts of CDI and dry THF equivalent to 6 times the mass of PEG2000, mix uniformly under nitrogen protection, and react at 30°C for 24h. Add 50 parts of ethylenediamine, continue to react at 30°C for 24h under nitrogen protection, concentrate the obtained solution by rotary evaporation, add dichloromethane equivalent to 17 times the mass of PEG 2000, mix evenly, pour into the liquid separator, and then add an amount equivalent to 2000 parts by mass 0.2 times the volume of dichloromethane saturated brine was fully shaken for washing, and after standing for 5 min, the organic phase was separated, and the washing was repeated 4 times. Add 20 parts of anhydrous sodium sulfate to fully shake, filter and retain the liquid phase after 5 minutes, evaporate and concentrate, and then precipitate in 50 parts of glacial ether, collect the precipitate a...

Embodiment 3

[0111] A preparation method of β-CD[3]PR, the method steps are as follows:

[0112] (1) with step (1) of embodiment 1.

[0113] (2) with step (2) of embodiment 1.

[0114] (3) 0.1 part of the shaft polymer and 0.8 part of β-CD were mixed and stirred in deionized water equivalent to 80 times the mass fraction of β-CD at 35°C for 5 days, and dried by blasting at 80°C for 24h, β-CD-PPR was obtained.

[0115] (4) In the reaction vessel, add 0.1 part of the β-CD-PPR, 0.8 part of tritylglycine, 0.85 part of BOP, 0.85 part of N,N-diisopropylethylamine, equivalent to β-CD- PPR 15 mass parts of THF and CH in a volume ratio of 1:1 3 The mixed solvent of CN was stirred at 25 °C for 24 h, and the obtained suspension was subjected to solid-liquid separation. The solid was washed 3 times with 1.5 parts of THF, 2 times with 1.5 parts of acetone, and once with 1.5 parts of methanol. In 1 part of DMSO, 2000D cellulose dialysis bag was used for dialysis against deionized water for 6 days, a...

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Abstract

The invention relates to a β-cyclodextrin polyrotaxane with accurate intercalation amount, a preparation method and an application thereof, and belongs to the technical field of supramolecular polymers. The β-cyclodextrin polyrotaxane uses a water-soluble polymer diamine containing a guest small molecule inclusion site structure in the middle of the molecular chain as the axis polymer, and β-CD as the host molecule embedded in the axis polymer , the two ends of the shaft polymer are terminated with a substance whose molecular volume is larger than the cavity size of β-CD to form a mechanical interlocking structure. The method uses the inclusion guest small molecule of β-CD as a preset inclusion site, introduces a water-soluble polymer diamine chain segment on both sides through a chemical reaction, and then performs self-assembly inclusion with β-CD, and finally Utilizing the inclusion stability between β‑CD and the preset inclusion site, a bulky capping group or molecule is introduced to both ends of the included polymer chain in a suitable solvent. β‑cyclodextrin polyrotaxanes can be used as polyhydroxyl crosslinkers for damping and toughening polymer materials.

Description

technical field [0001] The invention relates to a β-cyclodextrin polyrotaxane with accurate intercalation amount, a preparation method and application thereof, and belongs to the technical field of supramolecular polymers. Background technique [0002] Cyclodextrin (CD) is a polysaccharide macrocyclic molecule, usually composed of 6, 7 and 8 glucopyranose units linked end-to-end by α-1,4-glycosidic bonds to form α-CD, β-CD and γ-CD. The unique internal hydrophobic and external hydrophilic cavity structure endows CD not only capable of forming host-guest inclusion complexes through supramolecular interactions with small molecules that match the size of its cavity, but also self-assembled with polymers to form aggregates. Pseudorotaxane (CD-PPR). The structural parameters of CD and the common guest small molecules and polymers that can self-assemble with CD are shown in Table 1. [0003] Table 1 [0004] [0005] Cyclodextrin polyrotaxane (CD-PR) is formed by intercalat...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B37/16C08G83/00C08G18/64
CPCC08B37/0015C08G83/007C08G18/6484
Inventor 冯增国宋荣昊
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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