Photosensitive hydrogel containing cyclodextrin and azobenzene and preparation method of photosensitive hydrogel

A cyclodextrin and hydrogel technology, applied in the field of new materials, can solve the problems of insufficient biocompatibility and insufficient performance of mutual conversion effect, and achieve low biotoxicity, easy control and good biocompatibility. Effect

Inactive Publication Date: 2014-06-18
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this kind of hydrogel system is a hydrogel of a binary system that responds to light stimuli, and the mutual conversion effect between sol-gel is not obvious enough macroscopically, and the biocompatibility of the system is not good enough.

Method used

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  • Photosensitive hydrogel containing cyclodextrin and azobenzene and preparation method of photosensitive hydrogel
  • Photosensitive hydrogel containing cyclodextrin and azobenzene and preparation method of photosensitive hydrogel
  • Photosensitive hydrogel containing cyclodextrin and azobenzene and preparation method of photosensitive hydrogel

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preparation example Construction

[0033] The invention provides a method for preparing a photosensitive hydrogel containing cyclodextrin and azobenzene, comprising the following steps:

[0034] (1) Preparation of azobenzene-modified second-generation dendrimers with methyl groups at the end

[0035] Using triethylene glycol monomethyl ether as a starting material to prepare a first-generation dendritic molecule with a methyl end group; then using triethylene glycol as a raw material, adding pyridine p-toluenesulfonate after reacting with p-toluenesulfonyl chloride Acid acid makes one end capped and the other end activated. The reaction product of the two is modified and reacted with methyl gallate to prepare an ester-modified second-generation dendritic molecule (Me-G2-COOMe) with a methyl-terminated end, and the product is reduced to obtain a hydroxyl-modified second-generation dendritic molecule Then react with tetrabromine to obtain bromine-modified dendritic molecule (Me-G2-Br) at the end of the methyl gr...

Embodiment 1

[0043] Example 1 Preparation of azobenzene-modified end-methyl second-generation dendrimer Me-G 2 -Azo

[0044] The preparation process of this embodiment is as shown in the following formula (2):

[0045]

[0046] The first-generation dendrimers (Me-G 1 -OH), the yield was 92%. Then, according to the molar ratio of triethylene glycol and p-toluenesulfonyl chloride as 8:1, react in tetrahydrofuran solution at 0° C. for 2 hours, and react to obtain a triethylene glycol compound activated at one end with a yield of 63%. . Afterwards, pyridine p-toluenesulfonate was added to cap one end and protect the other end for activation. The reaction products of the two (first-generation dendrimers and triethylene glycol compounds) were modified and then reacted with methyl gallate to prepare ester-modified second-generation dendrimers (Me-G 2 -COOMe), the product undergoes a reduction reaction to obtain a hydroxyl-modified second-generation dendritic molecule (Me-G 2 -OH) reacts ...

Embodiment 2

[0048] Example 2 Preparation of photosensitive hydrogel containing cyclodextrin and azobenzene

[0049] Mix polyethylene glycol (PEG10K) and α-cyclodextrin to prepare polyrotaxane hydrogel, and ensure that the concentration of polyethylene glycol (PEG10K) and α-cyclodextrin is at least 0.1 mg / ml during the process; About 5 hours to form a polyrotaxane hydrogel, as figure 2 shown. Add water-soluble dendrimers (Me-G 2 -Azo) (i.e. the molar ratio of cyclodextrin groups to azophenyl groups is 1:1), the hydrogel is transformed into a sol, such as image 3 shown.

[0050] After irradiating it with ultraviolet light with a wavelength of 365nm for 30 minutes, and placing it in the dark for 10 hours, the sol-gel conversion will return to the gel state, such as Figure 4 shown. Then adopt visible light with a wavelength of 450nm to irradiate the formed hydrogel for 40min, and after standing for 8 hours, the sol appears again, as Figure 5 As shown, the photosensitive hydrogel con...

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Abstract

The invention discloses a preparation method of a photosensitive hydrogel containing a cyclodextrin and an azobenzene. The method comprises the following steps: mixing polyethylene glycol PEG10K with an Alpha-cyclodextrin so as to prepare a polyrotaxane hydrogel; then, adding water-soluble dendrimers Me-G2-Azo into the polyrotaxane hydrogel so as to convert the hydrogel into sol; and reassembling and decomposing the sol under the alternate irradiation of ultraviolet light and visible light so as to prepare the photosensitive hydrogel containing the cyclodextrin and the azobenzene. The photosensitive hydrogel disclosed by the invention is a ternary system hydrogel which contains the Alpha-cyclodextrin, the polyethylene glycol (PEG10K) and the second generation of dendrimers (Me-G2-Azo) modified by the azobenzene. The photosensitive hydrogel disclosed by the invention is good in biocompatibility and easy to prepared, and can be applied to the fields of preparation of photoswitches, optically-controlled motors, release of optically-controlled medicines and the like.

Description

technical field [0001] The invention belongs to the technical field of new materials, and specifically relates to an intelligent polymer material technology, more specifically to a photosensitive hydrogel containing cyclodextrin and azobenzene and a preparation method thereof. Background technique [0002] Smart hydrogels are hydrophilic polymers with a three-dimensional network structure that can respond significantly to small changes or stimuli in the external environment (such as temperature, pH value, electricity, light, magnetic field, specific biomolecules, etc.). , chemical separation, chemical sensors and catalysts have broad application prospects. Molecules with photoreversible properties will undergo conformational changes under light, such as azobenzene and its derivatives will undergo reversible cis-trans isomerization reactions under ultraviolet light, and it can be used as a photosensitive group to prepare photosensitive Sexual hydrogel. At present, the prepa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08J3/28C08J3/075C08L87/00C08G83/00C08G65/48C08B37/16
Inventor 贺小华张莉莉刘之龙
Owner EAST CHINA NORMAL UNIV
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