CN112870153A - Preparation method of temperature-sensitive gel containing carbon nano tube - Google Patents
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Abstract
The invention provides a preparation method of a temperature-sensitive gel containing carbon nano tubes. The preparation steps are as follows: modified cyclodextrin; adding thionyl chloride and N, N-dimethylformamide into a carboxylated multi-walled carbon nanotube to perform reflux; washing; dispersing into N, N-dimethylformamide, adding into N, N-dimethylformamide solution dissolved with modified cyclodextrin, and magnetically stirring; adding triethylamine, and stirring for reaction; dialyzing the reaction product with distilled water, and freeze-drying to obtain a carbon nano tube compound; adding hydrochloric acid into chitosan, and magnetically stirring; adding the carbon nano tube compound, and uniformly dispersing by ultrasonic to obtain a mixed solution; dissolving beta-sodium glycerophosphate in deionized water, and dropwise adding the solution into the mixed solution for magnetic stirring; adjusting pH to form gel, and freeze drying; pulverizing, and sieving. The temperature-sensitive gel containing the carbon nano tube prepared by the invention has quick gelation and good temperature sensitivity, and can be used as a good double-slow-release carrier.
Description
Technical Field
The invention relates to the field of materials, in particular to a preparation method of a temperature-sensitive gel containing carbon nano tubes.
Background
Carbon nanotubes are a seamless, hollow tube material formed of carbon with a layered structure similar to graphite found by Iijima in 1991. The carbon nanotube is composed of carbon atoms passing through sp2Hybridization to form hexagonal ring net-shaped space topological structure. The diameter of the carbon nano tube is in nanometer level, the length can reach micron level to millimeter level, the length-diameter ratio is large, and the carbon nano tube is a quasi-one-dimensional quantum wire. The carbon nano tube has the advantages of small density, large specific surface area, good thermochemical stability and mechanical propertyExcellent electromagnetic performance and field emission performance, which has become one of the most promising low-dimensional nanostructure materials, and has received extensive attention and research in many fields. However, due to the defects of the carbon nanotube material in the preparation process and the characteristics of easy agglomeration in water, the application of the carbon nanotube material as an adsorption material is limited. The beta-cyclodextrin is a natural organic material consisting of 7 glucose molecules, hydroxyl is fully attached to the outside, the internal structure of the molecule is hollow cavity hydrophobic, and the beta-cyclodextrin not only can form a host-guest inclusion complex with other materials, but also has certain binding capacity on heat absorbing and releasing elements. The carbon nano tube after acyl chlorination and hydroxypropyl beta-cyclodextrin are further grafted to form a new material under the conditions of catalysis and the like, so that the dispersity of the carbon nano tube is optimized, and the temperature-sensitive performance of the material can be improved.
Disclosure of Invention
The technical problem to be solved is as follows: the invention aims to provide a preparation method of a temperature-sensitive gel containing carbon nanotubes, and the prepared temperature-sensitive gel containing carbon nanotubes has quick gelation and good temperature sensitivity and can be used as a good double-slow-release carrier.
The technical scheme is as follows: a preparation method of temperature-sensitive gel containing carbon nano tubes comprises the following steps:
(1) dissolving 5g of hydroxypropyl-beta-cyclodextrin in 50mL of 25% NaOH solution, adding 10mL of epoxy chloropropane, and magnetically stirring at the temperature of 60 ℃ for 8-10 h;
(2) then adding 5mL of epoxy chloropropane, stirring and standing overnight;
(3) heating and concentrating the obtained solution to 20mL, adding acetone until no precipitate is generated, filtering, and placing the obtained product in a forced air drier for treatment to obtain modified cyclodextrin;
(4) taking 100mg of carboxylated multi-walled carbon nano-tube, adding 20-30mL of thionyl chloride and 1-2mLN, N-dimethylformamide, and refluxing for 24-30h at 40-45 ℃;
(5) carrying out suction filtration on the acyl chloride product, and washing the acyl chloride product for 3-5 times by using N, N-dimethylformamide;
(6) dispersing into 8-10mLN, N-dimethylformamide, adding into 5mL of N, N-dimethylformamide solution dissolved with 90-95mg of modified cyclodextrin, and magnetically stirring for 1-3 h;
(7) adding 200 mu L of triethylamine, magnetically stirring at 50-55 ℃, and reacting for 48-50 h;
(8) dialyzing the reaction product with distilled water for 3d, removing impurities, and freeze-drying for 48-50h to obtain a carbon nanotube compound;
(9) adding 5mL0.1mol/L hydrochloric acid into 100mg of chitosan, and magnetically stirring to fully dissolve the chitosan;
(10) adding the carbon nano tube compound, and uniformly dispersing by ultrasonic for 2-2.5h to obtain a mixed solution;
(11) dissolving beta-sodium glycerophosphate in deionized water, dropwise adding the solution into the mixed solution, and magnetically stirring for 30-40 min;
(12) adjusting pH to 6.9-7.2 with saturated disodium hydrogen phosphate solution, forming gel at 30-40 deg.C, and freeze drying for 48-50 hr;
(13) crushing, and sieving with a 60-mesh sieve to obtain the temperature-sensitive gel containing the carbon nano tube.
Further, the diameter of the carboxylated multi-wall carbon nano-tube in the step (4) is 20-40nm, and the length is less than 5 μm.
Further, in the step (9), the deacetylation degree of the chitosan is greater than 90.0%, and the viscosity is less than 100 cp.
Further, the addition amount of the carbon nanotube composite in the step (10) is 2 to 7 wt%.
Further, the concentration of the sodium beta-glycerophosphate in the step (11) is 400-900 mg/mL.
Has the advantages that:
1. according to the invention, free amine groups on chitosan chains are increased, so that electrostatic repulsion among chitosan chains is reduced, and inter-chain hydrogen bond effects are enhanced, and finally the temperature-sensitive gel has shorter gelation time at 37 ℃.
2. The beta-cyclodextrin modified carbon nano tube is adopted, the beta-cyclodextrin is a natural organic material consisting of 7 glucose molecules, hydroxyl is fully attached to the outside, the internal structure of the molecule is a cavity and is hydrophobic, and the beta-cyclodextrin modified carbon nano tube not only can form a host-guest inclusion complex with other materials, but also has certain binding capacity on heat absorbing and releasing elements, so that the dispersity of the carbon nano tube can be improved, and the temperature-sensitive performance of a temperature-sensitive material can be improved.
3. The temperature-sensitive gel containing the carbon nano tube prepared by the invention has quick gelation and good temperature sensitivity, and can be used as a good double-slow-release carrier.
Detailed Description
Example 1
A preparation method of temperature-sensitive gel containing carbon nano tubes comprises the following steps:
(1) dissolving 5g of hydroxypropyl-beta-cyclodextrin in 50mL of 25% NaOH solution, adding 10mL of epoxy chloropropane, and magnetically stirring at the temperature of 60 ℃ for 8 hours;
(2) then adding 5mL of epoxy chloropropane, stirring and standing overnight;
(3) heating and concentrating the obtained solution to 20mL, adding acetone until no precipitate is generated, filtering, and placing the obtained product in a forced air drier for treatment to obtain modified cyclodextrin;
(4) taking 100mg of carboxylated multi-wall carbon nano-tube, adding 20mL of thionyl chloride and 1mL of N, N-dimethylformamide, and refluxing for 24h at 40 ℃, wherein the diameter of the carboxylated multi-wall carbon nano-tube is 20-40nm, and the length of the carboxylated multi-wall carbon nano-tube is less than 5 microns;
(5) carrying out suction filtration on the acyl chloride product, and washing the acyl chloride product for 3 times by using N, N-dimethylformamide;
(6) dispersing into 8mLN, N-dimethylformamide, adding into 5mL of N, N-dimethylformamide solution dissolved with 90mg of modified cyclodextrin, and magnetically stirring for 1 h;
(7) adding 200 mu L of triethylamine, magnetically stirring at 50 ℃, and reacting for 48 h;
(8) dialyzing the reaction product with distilled water for 3d, removing impurities, and freeze-drying for 48h to obtain a carbon nanotube compound;
(9) adding 5mL0.1mol/L hydrochloric acid into 100mg of chitosan, and magnetically stirring to fully dissolve the chitosan, wherein the deacetylation degree of the chitosan is more than 90.0%, and the viscosity is less than 100 cp;
(10) adding 2 wt% of carbon nanotube compound, and performing ultrasonic dispersion for 2h to obtain a mixed solution;
(11) dissolving beta-sodium glycerophosphate into deionized water to prepare a beta-sodium glycerophosphate solution with the concentration of 400mg/mL, dropwise adding the solution into the mixed solution, and magnetically stirring for 30 min;
(12) adjusting pH to 6.9 with saturated disodium hydrogen phosphate solution, forming gel at 30 deg.C, and freeze drying for 48 hr;
(13) crushing, and sieving with a 60-mesh sieve to obtain the temperature-sensitive gel containing the carbon nano tube.
Example 2
A preparation method of temperature-sensitive gel containing carbon nano tubes comprises the following steps:
(1) dissolving 5g of hydroxypropyl-beta-cyclodextrin in 50mL of 25% NaOH solution, adding 10mL of epoxy chloropropane, and magnetically stirring at the temperature of 60 ℃ for 8.5 h;
(2) then adding 5mL of epoxy chloropropane, stirring and standing overnight;
(3) heating and concentrating the obtained solution to 20mL, adding acetone until no precipitate is generated, filtering, and placing the obtained product in a forced air drier for treatment to obtain modified cyclodextrin;
(4) taking 100mg of carboxylated multi-wall carbon nano-tube, adding 25mL of thionyl chloride and 1.3mL of N, N-dimethylformamide, and refluxing for 26h at 42 ℃, wherein the diameter of the carboxylated multi-wall carbon nano-tube is 20-40nm, and the length of the carboxylated multi-wall carbon nano-tube is less than 5 microns;
(5) carrying out suction filtration on the acyl chloride product, and washing the acyl chloride product for 4 times by using N, N-dimethylformamide;
(6) dispersing into 9mLN, N-dimethylformamide, adding into 5mL of N, N-dimethylformamide solution dissolved with 92mg of modified cyclodextrin, and magnetically stirring for 1.5 h;
(7) adding 200 mu L of triethylamine, magnetically stirring at 52 ℃ and reacting for 49 h;
(8) dialyzing the reaction product with distilled water for 3d, removing impurities, and freeze-drying for 49h to obtain a carbon nanotube compound;
(9) adding 5mL0.1mol/L hydrochloric acid into 100mg of chitosan, and magnetically stirring to fully dissolve the chitosan, wherein the deacetylation degree of the chitosan is more than 90.0%, and the viscosity is less than 100 cp;
(10) adding 3 wt% of carbon nanotube compound, and performing ultrasonic dispersion for 2h to obtain a mixed solution;
(11) dissolving beta-sodium glycerophosphate into deionized water to prepare a 600mg/mL beta-sodium glycerophosphate solution, dropwise adding the solution into the mixed solution, and magnetically stirring for 35 min;
(12) adjusting pH to 7.0 with saturated disodium hydrogen phosphate solution, forming gel at 35 deg.C, and freeze drying for 49 hr;
(13) crushing, and sieving with a 60-mesh sieve to obtain the temperature-sensitive gel containing the carbon nano tube.
Example 3
A preparation method of temperature-sensitive gel containing carbon nano tubes comprises the following steps:
(1) dissolving 5g of hydroxypropyl-beta-cyclodextrin in 50mL of 25% NaOH solution, adding 10mL of epoxy chloropropane, and magnetically stirring at the temperature of 60 ℃ for 9 hours;
(2) then adding 5mL of epoxy chloropropane, stirring and standing overnight;
(3) heating and concentrating the obtained solution to 20mL, adding acetone until no precipitate is generated, filtering, and placing the obtained product in a forced air drier for treatment to obtain modified cyclodextrin;
(4) taking 100mg of carboxylated multi-wall carbon nano-tube, adding 25mL of thionyl chloride and 1.5mL of LN, N-dimethylformamide, and refluxing for 27h at 43 ℃, wherein the diameter of the carboxylated multi-wall carbon nano-tube is 20-40nm, and the length of the carboxylated multi-wall carbon nano-tube is less than 5 microns;
(5) carrying out suction filtration on the acyl chloride product, and washing the acyl chloride product for 4 times by using N, N-dimethylformamide;
(6) dispersing into 9mLN, N-dimethylformamide, adding into 5mL of N, N-dimethylformamide solution dissolved with 93mg of modified cyclodextrin, and magnetically stirring for 2 h;
(7) adding 200 mu L of triethylamine, magnetically stirring at 53 ℃, and reacting for 49 h;
(8) dialyzing the reaction product with distilled water for 3d, removing impurities, and freeze-drying for 49h to obtain a carbon nanotube compound;
(9) adding 5mL0.1mol/L hydrochloric acid into 100mg of chitosan, and magnetically stirring to fully dissolve the chitosan, wherein the deacetylation degree of the chitosan is more than 90.0%, and the viscosity is less than 100 cp;
(10) adding 5 wt% of carbon nanotube compound, and performing ultrasonic treatment for 2.5h to uniformly disperse the carbon nanotube compound to obtain a mixed solution;
(11) dissolving beta-sodium glycerophosphate into deionized water to prepare a solution of the beta-sodium glycerophosphate with the concentration of 700mg/mL, dropwise adding the solution into the mixed solution, and magnetically stirring for 35 min;
(12) adjusting pH to 7.1 with saturated disodium hydrogen phosphate solution, forming gel at 35 deg.C, and freeze drying for 49 hr;
(13) crushing, and sieving with a 60-mesh sieve to obtain the temperature-sensitive gel containing the carbon nano tube.
Example 4
A preparation method of temperature-sensitive gel containing carbon nano tubes comprises the following steps:
(1) dissolving 5g of hydroxypropyl-beta-cyclodextrin in 50mL of 25% NaOH solution, adding 10mL of epoxy chloropropane, and magnetically stirring for 10 hours at the temperature of 60 ℃;
(2) then adding 5mL of epoxy chloropropane, stirring and standing overnight;
(3) heating and concentrating the obtained solution to 20mL, adding acetone until no precipitate is generated, filtering, and placing the obtained product in a forced air drier for treatment to obtain modified cyclodextrin;
(4) taking 100mg of carboxylated multi-wall carbon nano-tube, adding 30mL of thionyl chloride and 2mLN, N-dimethylformamide, and refluxing for 30h at 45 ℃, wherein the diameter of the carboxylated multi-wall carbon nano-tube is 20-40nm, and the length of the carboxylated multi-wall carbon nano-tube is less than 5 mu m;
(5) carrying out suction filtration on the acyl chloride product, and washing the acyl chloride product for 5 times by using N, N-dimethylformamide;
(6) dispersing into 10mLN, N-dimethylformamide, adding into 5mL of N, N-dimethylformamide solution dissolved with 95mg of modified cyclodextrin, and magnetically stirring for 3 h;
(7) adding 200 mu L of triethylamine, magnetically stirring at 55 ℃, and reacting for 50 h;
(8) dialyzing the reaction product with distilled water for 3d, removing impurities, and freeze-drying for 50h to obtain a carbon nanotube compound;
(9) adding 5mL0.1mol/L hydrochloric acid into 100mg of chitosan, and magnetically stirring to fully dissolve the chitosan, wherein the deacetylation degree of the chitosan is more than 90.0%, and the viscosity is less than 100 cp;
(10) adding 7 wt% of carbon nanotube compound, and performing ultrasonic treatment for 2.5h to uniformly disperse the carbon nanotube compound to obtain a mixed solution;
(11) dissolving beta-sodium glycerophosphate into deionized water to prepare a beta-sodium glycerophosphate solution with the concentration of 900mg/mL, dropwise adding the solution into the mixed solution, and magnetically stirring for 40 min;
(12) adjusting pH to 7.2 with saturated disodium hydrogen phosphate solution, forming gel at 40 deg.C, and freeze drying for 50 hr;
(13) crushing, and sieving with a 60-mesh sieve to obtain the temperature-sensitive gel containing the carbon nano tube.
The test method comprises the following steps:
the gel time was determined by inversion: the gel time is defined as the time required to transition from a sol to a gel, as a sol state (So1) when the system is in a flowing liquid state, and as a gel state (Ge1) when the system is in a non-flowing semi-solid state. And (3) taking 2mL of sol, injecting the sol into an ampoule bottle, then placing the ampoule bottle into a water bath at 37 ℃, inverting the sol every 1min to observe the fluidity of the sol, and recording the time when the sol does not flow after being inverted for 30s as the gelation time.
Measuring the swelling rate of the temperature-sensitive gel by adopting a weighing method, taking 50mg (Wo) of gel powder, putting the gel powder into a PBS solution, then respectively putting the gel powder into a temperature of 25 ℃ and a temperature of 37 ℃, sampling for 1 time every 2 hours, sucking the solution on the surface of the gel by using filter paper, weighing the mass of the solution as W, and calculating the swelling rate.
TABLE 1
Claims (5)
1. A preparation method of temperature-sensitive gel containing carbon nano tubes is characterized by comprising the following steps:
(1) dissolving 5g of hydroxypropyl-beta-cyclodextrin in 50mL of 25% NaOH solution, adding 10mL of epoxy chloropropane, and magnetically stirring at the temperature of 60 ℃ for 8-10 h;
(2) then adding 5mL of epoxy chloropropane, stirring and standing overnight;
(3) heating and concentrating the obtained solution to 20mL, adding acetone until no precipitate is generated, filtering, and placing the obtained product in a forced air drier for treatment to obtain modified cyclodextrin;
(4) taking 100mg of carboxylated multi-walled carbon nano-tube, adding 20-30mL of thionyl chloride and 1-2mLN, N-dimethylformamide, and refluxing for 24-30h at 40-45 ℃;
(5) carrying out suction filtration on the acyl chloride product, and washing the acyl chloride product for 3-5 times by using N, N-dimethylformamide;
(6) dispersing into 8-10mLN, N-dimethylformamide, adding into 5mL of N, N-dimethylformamide solution dissolved with 90-95mg of modified cyclodextrin, and magnetically stirring for 1-3 h;
(7) adding 200 mu L of triethylamine, magnetically stirring at 50-55 ℃, and reacting for 48-50 h;
(8) dialyzing the reaction product with distilled water for 3d, removing impurities, and freeze-drying for 48-50h to obtain a carbon nanotube compound;
(9) adding 5mL0.1mol/L hydrochloric acid into 100mg of chitosan, and magnetically stirring to fully dissolve the chitosan;
(10) adding the carbon nano tube compound, and uniformly dispersing by ultrasonic for 2-2.5h to obtain a mixed solution;
(11) dissolving beta-sodium glycerophosphate in deionized water, dropwise adding the solution into the mixed solution, and magnetically stirring for 30-40 min;
(12) adjusting pH to 6.9-7.2 with saturated disodium hydrogen phosphate solution, forming gel at 30-40 deg.C, and freeze drying for 48-50 hr;
(13) crushing, and sieving with a 60-mesh sieve to obtain the temperature-sensitive gel containing the carbon nano tube.
2. The method for preparing temperature-sensitive gel containing carbon nanotubes in claim 1, wherein the diameter of the carboxylated multi-walled carbon nanotubes in the step (4) is 20-40nm, and the length is less than 5 μm.
3. The method for preparing the temperature-sensitive gel containing the carbon nano tube according to claim 1, which is characterized in that: in the step (9), the deacetylation degree of the chitosan is more than 90.0%, and the viscosity is less than 100 cp.
4. The method for preparing temperature-sensitive gel containing carbon nanotubes in claim 1, wherein the carbon nanotube composite is added in an amount of 2-7 wt% in the step (10).
5. The method for preparing temperature-sensitive gel containing carbon nanotubes as claimed in claim 1, wherein the concentration of β -sodium glycerophosphate in step (11) is 400-900 mg/mL.
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Cited By (3)
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| CN115124987A (en) * | 2022-06-13 | 2022-09-30 | 陕西延长石油（集团）有限责任公司 | Long-acting hypersalinity-resistant low-temperature-resistant solid foam scrubbing agent for natural gas ground gathering and transportation pipeline and preparation method thereof |
| CN115245795A (en) * | 2022-02-23 | 2022-10-28 | 华东理工大学 | Preparation method of super-hydrophobic chitosan-based aerogel |
| CN118490538A (en) * | 2024-05-24 | 2024-08-16 | 湖南省青耕生物产业创新研究院有限公司 | Gel composition for beautifying and protecting skin and preparation method thereof |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115245795A (en) * | 2022-02-23 | 2022-10-28 | 华东理工大学 | Preparation method of super-hydrophobic chitosan-based aerogel |
| CN115245795B (en) * | 2022-02-23 | 2024-02-02 | 华东理工大学 | Preparation method of super-hydrophobic chitosan-based aerogel |
| CN115124987A (en) * | 2022-06-13 | 2022-09-30 | 陕西延长石油（集团）有限责任公司 | Long-acting hypersalinity-resistant low-temperature-resistant solid foam scrubbing agent for natural gas ground gathering and transportation pipeline and preparation method thereof |
| CN118490538A (en) * | 2024-05-24 | 2024-08-16 | 湖南省青耕生物产业创新研究院有限公司 | Gel composition for beautifying and protecting skin and preparation method thereof |
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