Polyurethane, single-component light-sensitive reversible hydrogel as well as preparation method and application of single-component light-sensitive reversible hydrogel

A technology of polyurethane and hydrogel, which is applied in the direction of non-active components of polymer compounds, aerosol delivery, emulsion delivery, etc. It can solve the problems of insufficient sensitivity of medium light sensitivity, insufficient sensitivity of light-sensitive groups, and difficult control of mutation range, etc. , to achieve excellent photoresponse speed, easy to control the content of functional groups, and simple preparation method

Active Publication Date: 2022-04-29
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] CN 201210440340 discloses a biocompatible natural polymer chitosan as a starting material, which is chemically modified to obtain a water-soluble photoresponse reversible Chitosan, the transformation of chitosan gel-sol can be realized by irradiation of ultraviolet light of different wavelengths, which improves the biocompatibility of chitosan hydrogel, but the hydrogel must be irradiated by specific wavelength ultraviolet light Achieving solution-gel transformation limits its application; CN2020115529831 discloses a solution of multi-arm polyethylene glycol azobenzene and multi-arm polyethylene glycol-β-cyclodextrin aqueous solution under ultraviolet-visible light irradiation - Gel transition, although the gel strength is high and biocompatibility is good, but the preparation method of the raw material is cumbersome; in addition, a light-sensitive hydrogel is also disclosed in the prior art, and the nitrogen-containing heterocycle is used as the pH Sensitivity section, azobenzene is a light-sensitive section, so it has both pH and light sensitivity and good compatibility, but due to the nitrogen-containing heterocycle, the hydrogel is not light-sensitive enough under acidic or alkaline conditions sensitive
It can be seen that the existing light-sensitive hydrogels have the disadvantages of cumbersome preparation process, insufficient sensitivity to medium light sensitivity, uncontrollable mutation range and low gel strength. It is necessary to put forward new ideas for the exploration of light-sensitive hydrogels.

Method used

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  • Polyurethane, single-component light-sensitive reversible hydrogel as well as preparation method and application of single-component light-sensitive reversible hydrogel
  • Polyurethane, single-component light-sensitive reversible hydrogel as well as preparation method and application of single-component light-sensitive reversible hydrogel
  • Polyurethane, single-component light-sensitive reversible hydrogel as well as preparation method and application of single-component light-sensitive reversible hydrogel

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Preparation of PU-CD-AB:

[0054] Dissolve 50g of polyethylene glycol, 4.5g of 2,3-dihydroxypropionaldehyde and 0.2g of dibutyltin dilaurate in 72mL of DMF, stir well, add 10.3g of hexamethylene diisocyanate, and mechanically stir , reacted at 80°C for 3.0h until the infrared characteristic absorption peak of -NCO disappeared. 5 times the volume of glacial ether was settled, and vacuum-dried to obtain polyurethane PU-AG-I containing aldehyde groups in the side chain (the weight-average molecular weight was 5.6×10 4 g / mol);

[0055] Dissolve 10g of PU-AG-I in 20mL of DMF, cool down to 15°C, and add monoamino-β-cyclodextrin (β-CD-NH 2 ) DMF solution (4.37g is dissolved in 4.5mLDMF), maintain the temperature reaction for 1.5, continue to dropwise add the DMF solution of 4-amino-azobenzene (0.76g is dissolved in 3mL DMF), continue to maintain the temperature reaction for 2h, and then use 5 times the volume of diethyl ether was settled, filtered, and vacuum-dried to const...

Embodiment 2

[0059] Preparation of PU-CD-AB:

[0060] Dissolve 50g of polyethylene glycol, 6.75g of 2,3-dihydroxypropionaldehyde and 0.22g of dibutyltin dilaurate in 95mL of DMF, stir evenly, add 14.6g of hexamethylene diisocyanate, and mechanically stir , react at 80°C for 3.2h until the infrared characteristic absorption peak of -NCO disappears. 5 times the volume of glacial ether was settled, and vacuum-dried to obtain polyurethane PU-AG-II containing aldehyde groups in the side chain (the weight-average molecular weight was 4.8×10 4 g / mol);

[0061] Dissolve 10g of PU-AG-II in 20mL of DMF, cool down to 17°C, and add monoamino-β-cyclodextrin (β-CD-NH 2 ) DMF solution (5.96g dissolved in 5mL DMF), maintain the temperature reaction for 2h, continue to dropwise add the DMF solution of 4-amino-azobenzene (1.04g dissolve in 3mL DMF), continue to maintain the temperature reaction for 1.5h, and then use 5 times the volume of diethyl ether was settled, filtered, and vacuum-dried to constant ...

Embodiment 3

[0065] Preparation of PU-CD-AB:

[0066] Dissolve 50g of polyethylene glycol, 9.0g of 2,3-dihydroxypropionaldehyde and 0.25g of dibutyltin dilaurate in 100mL of DMF, stir evenly, add 18.85g of hexamethylene diisocyanate, and mechanically stir , React at 80°C for 3.5h until the characteristic infrared absorption peak of -NCO disappears. 5 times the volume of glacial ether was settled, and vacuum-dried to obtain polyurethane PU-AG-III containing aldehyde groups in the side chain (the weight-average molecular weight was 6.4×10 4 g / mol);

[0067] Dissolve 10g of PU-AG-II in 15mL of DMF, cool down to 18°C, and add monoamino-β-cyclodextrin (β-CD-NH 2 ) DMF solution (7.28g dissolved in 7mL DMF), maintain the temperature reaction for 2h, continue to dropwise add the DMF solution of 4-amino-azobenzene (1.26g dissolve in 3mL DMF), continue to maintain the temperature reaction for 1.5h, and then use 5 times the volume of diethyl ether was settled, filtered, and vacuum-dried to constan...

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Abstract

The invention belongs to the technical field of high polymer material preparation, and particularly relates to polyurethane, single-component light-sensitive reversible hydrogel and a preparation method and application of the single-component light-sensitive reversible hydrogel, a side chain of the polyurethane contains a beta-cyclodextrin (beta-CD) group and an azobenzene group, a main chain is based on polyethylene glycol, the preparation method is simple, and the content of functional groups is easy to control; the hydrogel prepared on the basis of the polyurethane has high photosensitivity and high response speed to white light and ultraviolet light media, can realize solution-gel-solution circulation along with irradiation of ultraviolet light-white light-ultraviolet light, and can be repeatedly used for multiple times; the hydrogel is extremely sensitive to light rays, the time T (liquid-gel) for converting a solution into a gel state is 0.5-1.5 min, the time T (gel-liquid) for converting the gel into a liquid state is 5-10 min, and the hydrogel shows excellent light response speed; the hydrogel has relatively high anti-cracking strength, and the anti-cracking strength can reach 5 to 20 kPa.

Description

technical field [0001] The invention belongs to the technical field of polymer material preparation, and specifically relates to polyurethane, a single-component light-sensitive reversible hydrogel and a preparation method and application thereof. Background technique [0002] The information disclosed in this background section is only intended to increase the understanding of the general background of the present invention, and is not necessarily taken as an acknowledgment or any form of suggestion that the information constitutes the prior art already known to those skilled in the art. [0003] Hydrogel is a three-dimensional network polymer that can contain water but is insoluble in water and does not react with water, but can deform in aqueous solution. Light-sensitive hydrogels usually contain light-sensitive groups. It is a non-contact exogenous stimulus whose wavelength and intensity can be controlled remotely, and is often used in the design of drug carriers. [00...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G81/00C08J3/075C08J3/28C08L87/00A61K9/06A61K47/40
CPCC08G81/00C08J3/075C08J3/28A61K9/06A61K47/40C08J2387/00
Inventor 侯昭升秦子昊纪晨旭张振华朱连连
Owner SHANDONG NORMAL UNIV
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