CN113234238B - Light-responsive self-repairing polymer gel and preparation method thereof - Google Patents
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- 229920000642 polymer Polymers 0.000 title claims abstract description 102
- 238000002360 preparation method Methods 0.000 title abstract description 18
- 238000001879 gelation Methods 0.000 title description 2
- 230000004298 light response Effects 0.000 claims abstract description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 60
- 229920002873 Polyethylenimine Polymers 0.000 claims description 18
- 239000000243 solution Substances 0.000 claims description 17
- YBMDPYAEZDJWNY-UHFFFAOYSA-N 1,2,3,3,4,4,5,5-octafluorocyclopentene Chemical compound FC1=C(F)C(F)(F)C(F)(F)C1(F)F YBMDPYAEZDJWNY-UHFFFAOYSA-N 0.000 claims description 10
- -1 5-formyl-2-methylthiophene-3-yl Chemical group 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 10
- 238000001704 evaporation Methods 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 8
- 239000011259 mixed solution Substances 0.000 claims description 8
- 238000010992 reflux Methods 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- 229920006299 self-healing polymer Polymers 0.000 claims 4
- 238000000034 method Methods 0.000 claims 1
- 230000009977 dual effect Effects 0.000 abstract description 9
- 239000000499 gel Substances 0.000 description 94
- 238000005303 weighing Methods 0.000 description 8
- 238000005316 response function Methods 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- 238000010586 diagram Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000000017 hydrogel Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/09—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids
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- C—CHEMISTRY; METALLURGY
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/09—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids
- C08J3/091—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in organic liquids characterised by the chemical constitution of the organic liquid
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/02—Use of particular materials as binders, particle coatings or suspension media therefor
- C09K11/025—Use of particular materials as binders, particle coatings or suspension media therefor non-luminescent particle coatings or suspension media
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
- C08J2379/02—Polyamines
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/45—Heterocyclic compounds having sulfur in the ring
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Abstract
The invention discloses a light response type self-repairing polymer gel and a preparation method thereof. According to the invention, the self-repairing polymer gel has self-repairing capability, and the photochromic group is grafted on the photo-responsive polymer, so that the photo-responsive self-repairing polymer gel has dual characteristics of fluorescence and photochromism, the application field of the photo-responsive self-repairing polymer gel is favorably expanded, and the prepared photo-responsive self-repairing polymer gel has excellent self-repairing property.
Description
Technical Field
The invention belongs to the field of intelligent high polymer materials, and particularly relates to a light-responsive self-repairing high polymer gel and a preparation method thereof.
Background
Biological tissues can restore their original functions and structures by self-repair of cells or tissues when they are damaged by the outside. As a soft texture and high water-bearing material, the hydrogel is widely applied to the fields of sensing and detection, drug release, drivers, tissue engineering and the like, has self-repairing performance, can prolong the service life of the hydrogel, and can greatly improve the use safety.
Since the beginning of the 21 st century, numerous scientists around the world have been devoted to developing multifunctional gel materials to deal with the complex problems. The gel with the light response characteristic and the self-repairing characteristic is prepared, and has very wide application prospect in the fields of functional devices, biomedicine, information storage and the like. At present, the photo-responsive self-repairing polymer gel only has single photo-responsive characteristic, has single function, cannot meet the increasing application requirements of various fields, and therefore, an attempt is necessary to prepare the photo-responsive self-repairing polymer gel.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide the photo-responsive self-repairing polymer gel which has the self-repairing capability and is grafted with the photochromic groups, so that the photo-responsive self-repairing polymer gel has the dual characteristics of fluorescence and photochromism, the application field of the photo-responsive self-repairing polymer gel is favorably expanded, and the prepared photo-responsive self-repairing polymer gel has excellent self-repairing capability and has wide application prospect in the fields of biomedicine, functional devices, sensing and the like.
The structure of the light-responsive self-repairing polymer gel for solving the technical problems is as follows:
wherein,,
n is an integer greater than 1.
Optionally, the light-responsive self-repairing polymer gel contains a photochromic unit, and the photochromic unit is perfluoro-cyclodiarylethene.
Optionally, the light-responsive self-repairing polymer gel contains a photoinduced fluorescence unit, and the photoinduced fluorescence unit is hyperbranched polyethyleneimine.
Optionally, R is one of the following groups:
accordingly, another technical problem to be solved by the invention is to provide a preparation method of the light-responsive self-repairing polymer gel.
The preparation method of the light response type self-repairing polymer gel for solving the technical problems comprises the following steps of:
step S1, dissolving 1, 2-bis (5-formyl-2-methylthiophene-3-yl) perfluorocyclopentene in methanol, wherein the mass ratio of the 1, 2-bis (5-formyl-2-methylthiophene-3-yl) perfluorocyclopentene to the methanol is 0.5-10%;
s2, dissolving hyperbranched polyethyleneimine in methanol, wherein the mass ratio of the hyperbranched polyethyleneimine to the methanol is 5-30%;
step S3, mixing and stirring the two solutions prepared in the steps S1 and S2 in a mixing container for 0.1-1h;
step S4, heating and refluxing the mixed solution prepared in the step S3 at 40-70 ℃ for 0.5-3h;
and S5, decompressing and evaporating the solution prepared in the step S4 for 1-5 hours at the same temperature to obtain the light-responsive self-repairing polymer gel.
One of the above technical solutions has the following advantages or beneficial effects: on the basis of not increasing the synthesis difficulty and the synthesis cost, the invention expands the light response function of the light response type self-repairing polymer gel, so that the light response type self-repairing polymer gel has the dual functions of photochromism and fluorescence, and greatly expands the application field of the light response type self-repairing polymer gel.
Drawings
For a clearer description of an embodiment of the invention, reference will be made to the accompanying drawings of embodiments, which are given for clarity, wherein:
FIG. 1 is a FT-IR characterization diagram of a photo-responsive self-repairing polymer gel prepared in example 1.
FIG. 2 is an ultraviolet absorption diagram of the photo-responsive self-repairing polymer gel prepared in example 1.
FIG. 3 is a fluorescence emission diagram of the photo-responsive self-repairing polymer gel prepared in example 1.
FIG. 4 is a nuclear magnetic resonance hydrogen spectrum of the photo-responsive self-repairing polymer gel prepared in example 1.
FIG. 5 is a nuclear magnetic resonance hydrogen spectrum of the photo-responsive self-repairing polymer gel prepared in example 2.
FIG. 6 is a nuclear magnetic resonance hydrogen spectrum of the photo-responsive self-repairing polymer gel prepared in example 3.
FIG. 7 is a nuclear magnetic resonance hydrogen spectrum of the photo-responsive self-repairing polymer gel prepared in example 4.
FIG. 8 is a nuclear magnetic resonance hydrogen spectrum of the photo-responsive self-repairing polymer gel prepared in example 5.
FIG. 9 is a nuclear magnetic resonance hydrogen spectrum of the photo-responsive self-repairing polymer gel prepared in example 6.
Detailed Description
The invention will be further illustrated with reference to specific examples. It is to be understood that these examples are illustrative of the present invention and are not intended to limit the scope of the present invention. Further, it is understood that various changes and modifications may be made by those skilled in the art after reading the teachings of the present invention, and such equivalents are intended to fall within the scope of the claims appended hereto.
Example 1
The example provides a light response type self-repairing polymer gel, which has the structure as follows:
wherein,,
n is an integer greater than 1.
Further, the light-responsive self-repairing polymer gel contains a photochromic unit, wherein the photochromic unit is perfluoro-cyclodiarylethene.
Further, the light-responsive self-repairing polymer gel contains a photoinduced fluorescence unit, wherein the photoinduced fluorescence unit is hyperbranched polyethyleneimine.
Further, R is a group-CHO.
Correspondingly, the invention also provides a preparation method of the light-responsive self-repairing polymer gel, which comprises the following steps:
step S1, weighing 0.025 g of 1, 2-bis (5-formyl-2-methylthiophene-3-yl) perfluorocyclopentene to be dissolved in 5 g of methanol;
step S2, weighing 0.5 g of hyperbranched polyethyleneimine to be dissolved in 5 g of methanol;
step S3, transferring the two solutions prepared in the steps S1 and S2 into a round-bottom flask with 20ml capacity, and mixing and stirring for 0.1h;
step S4, heating and refluxing the mixed solution prepared in the step S3 at 40 ℃ for 3 hours;
and S5, decompressing and evaporating the solution prepared in the step S4 for 5 hours at the temperature of 40 ℃ to obtain the light-responsive self-repairing polymer gel.
Referring to fig. 1 to 4, it can be found that the light-responsive self-repairing polymer gel prepared by the above-mentioned preparation method changes from yellowish to reddish brown under irradiation of 254nm ultraviolet lamp and returns to original yellowish under irradiation of visible light, and the light-responsive self-repairing polymer gel shows yellow fluorescence under 390nm ultraviolet lamp. Therefore, the photo-response type self-repairing polymer gel has the advantages that the photo-response function of the photo-response type self-repairing polymer gel is expanded, the photo-response type self-repairing polymer gel has the dual functions of photochromism and fluorescence, and the application field of the photo-response type self-repairing polymer gel is greatly expanded.
Example 2
The example provides a light response type self-repairing polymer gel, which has the structure as follows:
wherein,,
n is an integer greater than 1.
Further, the light-responsive self-repairing polymer gel contains a photochromic unit, wherein the photochromic unit is perfluoro-cyclodiarylethene.
Further, the light-responsive self-repairing polymer gel contains a photoinduced fluorescence unit, wherein the photoinduced fluorescence unit is hyperbranched polyethyleneimine.
Further, the R is a group-CH 2 -CHO。
Correspondingly, the invention also provides a preparation method of the light-responsive self-repairing polymer gel, which comprises the following steps:
step S1, weighing 0.05 g of 1, 2-bis (5-formyl-2-methylthiophene-3-yl) perfluorocyclopentene to dissolve in 5 g of methanol;
step S2, 1 gram of hyperbranched polyethyleneimine is weighed and dissolved in 5 grams of methanol;
step S3, transferring the two solutions prepared in the steps S1 and S2 into a round-bottom flask with 20ml capacity, and mixing and stirring for 0.3h;
step S4, heating and refluxing the mixed solution prepared in the step S3 at 50 ℃ for 2 hours;
and S5, decompressing and evaporating the solution prepared in the step S4 for 4 hours at 50 ℃ to obtain the light-responsive self-repairing polymer gel.
Referring to fig. 1,2, 3 and 5, it can be seen that the light-responsive self-repairing polymer gel prepared by the above preparation method changes from yellowish to reddish brown under irradiation of 254nm ultraviolet lamp, and changes back to original yellowish under irradiation of visible light, and the light-responsive self-repairing polymer gel shows yellow fluorescence under 390nm ultraviolet lamp. Therefore, the photo-response type self-repairing polymer gel has the advantages that the photo-response function of the photo-response type self-repairing polymer gel is expanded, the photo-response type self-repairing polymer gel has the dual functions of photochromism and fluorescence, and the application field of the photo-response type self-repairing polymer gel is greatly expanded.
Example 3
The example provides a light response type self-repairing polymer gel, which has the structure as follows:
wherein,,
n is an integer greater than 1.
Further, the light-responsive self-repairing polymer gel contains a photochromic unit, wherein the photochromic unit is perfluoro-cyclodiarylethene.
Further, the light-responsive self-repairing polymer gel contains a photoinduced fluorescence unit, wherein the photoinduced fluorescence unit is hyperbranched polyethyleneimine.
Further, the R is a group
Correspondingly, the invention also provides a preparation method of the light-responsive self-repairing polymer gel, which comprises the following steps:
step S1, weighing 0.1 g of 1, 2-bis (5-formyl-2-methylthiophene-3-yl) perfluorocyclopentene to be dissolved in 5 g of methanol;
step S2, 1 gram of hyperbranched polyethyleneimine is weighed and dissolved in 5 grams of methanol;
step S3, transferring the two solutions prepared in the steps S1 and S2 into a round-bottom flask with 20ml capacity, and mixing and stirring for 0.5h;
step S4, heating and refluxing the mixed solution prepared in the step S3 at 60 ℃ for 1h;
and S5, decompressing and evaporating the solution prepared in the step S4 for 1h at the temperature of 60 ℃ to obtain the light-responsive self-repairing polymer gel.
Referring to fig. 1,2, 3 and 6, it can be seen that the light-responsive self-repairing polymer gel prepared by the above preparation method changes from yellowish to reddish brown under irradiation of 254nm ultraviolet lamp, and changes back to original yellowish under irradiation of visible light, and the light-responsive self-repairing polymer gel shows yellow fluorescence under 390nm ultraviolet lamp. Therefore, the photo-response type self-repairing polymer gel has the advantages that the photo-response function of the photo-response type self-repairing polymer gel is expanded, the photo-response type self-repairing polymer gel has the dual functions of photochromism and fluorescence, and the application field of the photo-response type self-repairing polymer gel is greatly expanded.
Example 4
The example provides a light response type self-repairing polymer gel, which has the structure as follows:
wherein,,
n is an integer greater than 1.
Further, the light-responsive self-repairing polymer gel contains a photochromic unit, wherein the photochromic unit is perfluoro-cyclodiarylethene.
Further, the light-responsive self-repairing polymer gel contains a photoinduced fluorescence unit, wherein the photoinduced fluorescence unit is hyperbranched polyethyleneimine.
Further, the R is a group
Correspondingly, the invention also provides a preparation method of the light-responsive self-repairing polymer gel, which comprises the following steps:
step S1, weighing 0.5 g of 1, 2-bis (5-formyl-2-methylthiophene-3-yl) perfluorocyclopentene to be dissolved in 5 g of methanol;
step S2, 1.5 g of hyperbranched polyethyleneimine is weighed and dissolved in 5 g of methanol;
step S3, transferring the two solutions prepared in the steps S1 and S2 into a round-bottom flask with 20ml capacity, and mixing and stirring for 2 hours;
step S4, heating and refluxing the mixed solution prepared in the step S3 at 70 ℃ for 1h;
and S5, decompressing and evaporating the solution prepared in the step S4 for 1h at 70 ℃ to obtain the light-responsive self-repairing polymer gel.
Referring to fig. 1,2, 3 and 7, it can be seen that the light-responsive self-repairing polymer gel prepared by the preparation method is changed from yellowish to reddish brown under the irradiation of a 490nm ultraviolet lamp, and is changed back to original yellowish under the irradiation of 690nm visible light, and the light-responsive self-repairing polymer gel shows yellow fluorescence under the 390nm ultraviolet lamp. Therefore, the photo-response type self-repairing polymer gel has the advantages that the photo-response function of the photo-response type self-repairing polymer gel is expanded, the photo-response type self-repairing polymer gel has the dual functions of photochromism and fluorescence, and the application field of the photo-response type self-repairing polymer gel is greatly expanded.
Example 5
The example provides a light response type self-repairing polymer gel, which has the structure as follows:
wherein,,
n is an integer greater than 1.
Further, the light-responsive self-repairing polymer gel contains a photochromic unit, wherein the photochromic unit is perfluoro-cyclodiarylethene.
Further, the light-responsive self-repairing polymer gel contains a photoinduced fluorescence unit, wherein the photoinduced fluorescence unit is hyperbranched polyethyleneimine.
Further, the R is a group
Correspondingly, the invention also provides a preparation method of the light-responsive self-repairing polymer gel, which comprises the following steps:
step S1, weighing 0.5 g of 1, 2-bis (5-formyl-2-methylthiophene-3-yl) perfluorocyclopentene to be dissolved in 5 g of methanol;
step S2, 1.5 g of hyperbranched polyethyleneimine is weighed and dissolved in 5 g of methanol;
step S3, transferring the two solutions prepared in the steps S1 and S2 into a round-bottom flask with 20ml capacity, and mixing and stirring for 1h;
step S4, heating and refluxing the mixed solution prepared in the step S3 at 50 ℃ for 1h;
and S5, decompressing and evaporating the solution prepared in the step S4 for 5 hours at 50 ℃ to obtain the light-responsive self-repairing polymer gel.
Referring to fig. 1,2, 3 and 8, it can be seen that the light-responsive self-repairing polymer gel prepared by the above preparation method changes from yellowish to reddish brown under irradiation of 254nm ultraviolet lamp, and changes back to original yellowish under irradiation of visible light, and the light-responsive self-repairing polymer gel shows yellow fluorescence under 390nm ultraviolet lamp. Therefore, the photo-response type self-repairing polymer gel has the advantages that the photo-response function of the photo-response type self-repairing polymer gel is expanded, the photo-response type self-repairing polymer gel has the dual functions of photochromism and fluorescence, and the application field of the photo-response type self-repairing polymer gel is greatly expanded.
Example 6
The example provides a light response type self-repairing polymer gel, which has the structure as follows:
wherein,,
n is an integer greater than 1.
Further, the light-responsive self-repairing polymer gel contains a photochromic unit, wherein the photochromic unit is perfluoro-cyclodiarylethene.
Further, the light-responsive self-repairing polymer gel contains a photoinduced fluorescence unit, wherein the photoinduced fluorescence unit is hyperbranched polyethyleneimine.
Further, the R is a group
Correspondingly, the invention also provides a preparation method of the light-responsive self-repairing polymer gel, which comprises the following steps:
step S1, weighing 0.1 g of 1, 2-bis (5-formyl-2-methylthiophene-3-yl) perfluorocyclopentene to be dissolved in 5 g of methanol;
step S2, weighing 0.8 g of hyperbranched polyethyleneimine to be dissolved in 5 g of methanol;
step S3, transferring the two solutions prepared in the steps S1 and S2 into a round-bottom flask with 20ml capacity, and mixing and stirring for 0.5h;
step S4, heating and refluxing the mixed solution prepared in the step S3 at 60 ℃ for 1h;
and S5, decompressing and evaporating the solution prepared in the step S4 for 3 hours at the temperature of 60 ℃ to obtain the light-responsive self-repairing polymer gel.
It can be found that the light-responsive self-repairing polymer gel prepared by the preparation method changes from yellowish to reddish brown under the irradiation of a 490nm ultraviolet lamp, and changes back to the original yellowish under the irradiation of 690 visible light, and the light-responsive self-repairing polymer gel shows yellow fluorescence under the 390nm ultraviolet lamp. Therefore, the photo-response type self-repairing polymer gel has the advantages that the photo-response function of the photo-response type self-repairing polymer gel is expanded, the photo-response type self-repairing polymer gel has the dual functions of photochromism and fluorescence, and the application field of the photo-response type self-repairing polymer gel is greatly expanded.
Although embodiments of the present invention have been disclosed above, it is not limited to the use as set forth in the specification and embodiments, it is well suited to various fields of use for the invention, and further modifications will be readily apparent to those skilled in the art, and accordingly, the invention is not limited to the particular details without departing from the general concepts defined in the claims and the equivalents thereof.
Claims (4)
1. The light response type self-repairing polymer gel is characterized by comprising the following structural components:
wherein,,
n is an integer greater than 1;
the R is one of the following groups:
2. the light-responsive self-healing polymer gel according to claim 1, wherein the light-responsive self-healing polymer gel contains a photochromic unit, and the photochromic unit is a perfluorocyclodiarylethene.
3. The light-responsive self-healing polymer gel according to claim 1, wherein the light-responsive self-healing polymer gel contains a photo-fluorescing unit that is hyperbranched polyethyleneimine.
4. A method for preparing the light-responsive self-repairing polymer gel according to any one of claims 1 to 3, comprising the steps of:
step S1, dissolving 1, 2-bis (5-formyl-2-methylthiophene-3-yl) perfluorocyclopentene in methanol, wherein the mass ratio of the 1, 2-bis (5-formyl-2-methylthiophene-3-yl) perfluorocyclopentene to the methanol is 0.5-10%;
s2, dissolving hyperbranched polyethyleneimine in methanol, wherein the mass ratio of the hyperbranched polyethyleneimine to the methanol is 5-30%;
step S3, mixing and stirring the two solutions prepared in the steps S1 and S2 in a mixing container for 0.1-1h;
step S4, heating and refluxing the mixed solution prepared in the step S3 at 40-70 ℃ for 0.5-3h;
and S5, decompressing and evaporating the solution prepared in the step S4 for 1-5 hours at the same temperature to obtain the light-responsive self-repairing polymer gel.
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