CN116693930A - Preparation method and application of polypyrrole-modified carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel photo-thermal material - Google Patents
Preparation method and application of polypyrrole-modified carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel photo-thermal material Download PDFInfo
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- 235000010948 carboxy methyl cellulose Nutrition 0.000 title claims abstract description 151
- 239000001768 carboxy methyl cellulose Substances 0.000 title claims abstract description 146
- 239000008112 carboxymethyl-cellulose Substances 0.000 title claims abstract description 146
- 239000013317 conjugated microporous polymer Substances 0.000 title claims abstract description 84
- 239000004964 aerogel Substances 0.000 title claims abstract description 47
- 239000002131 composite material Substances 0.000 title claims abstract description 45
- 239000000463 material Substances 0.000 title claims abstract description 45
- 125000002057 carboxymethyl group Polymers [H]OC(=O)C([H])([H])[*] 0.000 title claims abstract description 35
- 238000002360 preparation method Methods 0.000 title claims abstract description 26
- 229920002134 Carboxymethyl cellulose Polymers 0.000 claims abstract description 148
- 229920000128 polypyrrole Polymers 0.000 claims abstract description 91
- 239000013535 sea water Substances 0.000 claims abstract description 23
- 150000002500 ions Chemical class 0.000 claims abstract description 19
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- 239000002351 wastewater Substances 0.000 claims abstract description 11
- 238000000746 purification Methods 0.000 claims abstract description 10
- 238000010612 desalination reaction Methods 0.000 claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 45
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 239000008367 deionised water Substances 0.000 claims description 6
- 229910021641 deionized water Inorganic materials 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- 239000007921 spray Substances 0.000 claims description 6
- YWDUZLFWHVQCHY-UHFFFAOYSA-N 1,3,5-tribromobenzene Chemical compound BrC1=CC(Br)=CC(Br)=C1 YWDUZLFWHVQCHY-UHFFFAOYSA-N 0.000 claims description 5
- ZDRMMTYSQSIGRY-UHFFFAOYSA-N 1,3,5-triethynylbenzene Chemical compound C#CC1=CC(C#C)=CC(C#C)=C1 ZDRMMTYSQSIGRY-UHFFFAOYSA-N 0.000 claims description 5
- IMQLKJBTEOYOSI-GPIVLXJGSA-N Inositol-hexakisphosphate Chemical compound OP(O)(=O)O[C@H]1[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@@H]1OP(O)(O)=O IMQLKJBTEOYOSI-GPIVLXJGSA-N 0.000 claims description 5
- IMQLKJBTEOYOSI-UHFFFAOYSA-N Phytic acid Natural products OP(O)(=O)OC1C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C1OP(O)(O)=O IMQLKJBTEOYOSI-UHFFFAOYSA-N 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 239000000467 phytic acid Substances 0.000 claims description 5
- 229940068041 phytic acid Drugs 0.000 claims description 5
- 235000002949 phytic acid Nutrition 0.000 claims description 5
- 238000000967 suction filtration Methods 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 4
- 238000004140 cleaning Methods 0.000 claims description 4
- 239000011248 coating agent Substances 0.000 claims description 4
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- 238000005507 spraying Methods 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 abstract description 6
- 230000003373 anti-fouling effect Effects 0.000 abstract description 2
- 238000001704 evaporation Methods 0.000 description 42
- 230000008020 evaporation Effects 0.000 description 42
- 239000000243 solution Substances 0.000 description 16
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
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- 238000010586 diagram Methods 0.000 description 5
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- 230000015784 hyperosmotic salinity response Effects 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
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- 238000002354 inductively-coupled plasma atomic emission spectroscopy Methods 0.000 description 2
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- 238000010521 absorption reaction Methods 0.000 description 1
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- 239000003054 catalyst Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000001186 cumulative effect Effects 0.000 description 1
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- 230000008034 disappearance Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000002384 drinking water standard Substances 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
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- 230000008014 freezing Effects 0.000 description 1
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- 235000003642 hunger Nutrition 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000009616 inductively coupled plasma Methods 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 238000003808 methanol extraction Methods 0.000 description 1
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- 238000004321 preservation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000001350 scanning transmission electron microscopy Methods 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 230000037351 starvation Effects 0.000 description 1
- 239000008400 supply water Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000002207 thermal evaporation Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F1/00—Treatment of water, waste water, or sewage
- C02F1/02—Treatment of water, waste water, or sewage by heating
- C02F1/04—Treatment of water, waste water, or sewage by heating by distillation or evaporation
- C02F1/14—Treatment of water, waste water, or sewage by heating by distillation or evaporation using solar energy
-
- 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
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/0061—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof characterized by the use of several polymeric components
-
- 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
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/28—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof by elimination of a liquid phase from a macromolecular composition or article, e.g. drying of coagulum
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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
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/36—After-treatment
- C08J9/365—Coating
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2101/00—Nature of the contaminant
- C02F2101/10—Inorganic compounds
- C02F2101/20—Heavy metals or heavy metal compounds
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2101/00—Nature of the contaminant
- C02F2101/30—Organic compounds
- C02F2101/308—Dyes; Colorants; Fluorescent agents
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- C—CHEMISTRY; METALLURGY
- C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
- C02F2103/00—Nature of the water, waste water, sewage or sludge to be treated
- C02F2103/08—Seawater, e.g. for desalination
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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
- C08J2201/00—Foams characterised by the foaming process
- C08J2201/04—Foams characterised by the foaming process characterised by the elimination of a liquid or solid component, e.g. precipitation, leaching out, evaporation
- C08J2201/048—Elimination of a frozen liquid phase
- C08J2201/0484—Elimination of a frozen liquid phase the liquid phase being aqueous
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- C08J2301/00—Characterised by the use of cellulose, modified cellulose or cellulose derivatives
- C08J2301/08—Cellulose derivatives
- C08J2301/26—Cellulose ethers
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- C08J2465/00—Characterised by the use of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Derivatives of such polymers
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- C08J2479/00—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 C08J2461/00 - C08J2477/00
- C08J2479/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
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Abstract
The invention relates to the technical field of photo-thermal material preparation, in particular to a preparation method of polypyrrole modified carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel photo-thermal material, which comprises the following steps: step one, preparing a conjugated microporous polymer; step two, preparing a sulfonated conjugated microporous polymer; step three, preparing carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel; and step four, preparing the polypyrrole modified carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel photo-thermal material. The polypyrrole modified carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel photo-thermal material capable of efficiently generating solar steam has higher solar energy conversion efficiency, excellent salt resistance and anti-fouling performance, and has a certain practical application value in the aspects of future sea water desalination and (containing heavy metal ions or dyes) wastewater purification treatment.
Description
Technical Field
The invention relates to the technical field of photo-thermal material preparation, in particular to a preparation method and application of a polypyrrole modified carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel photo-thermal material.
Background
With the rapid development of industry and population growth, shortage and pollution of drinking water has become a great challenge and serious threat to future sustainable development. Water resources are contaminated with inorganic, organic and other toxic contaminants. Therefore, the shortage of fresh water has also become a serious threat to economic development and human survival. By 2050, global water demand is expected to increase by 55%, which will lead to water starvation in 40% of the world population. Thus, the use of clean and renewable energy sources to produce fresh water and purified water resources is essential, sunlight being a promising unlimited energy source, and fresh water can be produced by steam generation, purification and distillation.
In solar driven interfacial evaporation (SSG) systems, solar steam generators are used that consist of a photo-thermal material and a support substrate as top and bottom layers, respectively. The photo-thermal material converts sunlight into heat, and the substrate simultaneously transfers water to the photo-thermal layer to generate steam. The support substrate should have a low thermal conductivity to concentrate heat at the evaporator surface and a good water transport capacity to continuously supply water to the photo-thermal layer, together with an excellent mechanical strength of the base material in order to well retain the top layer photo-thermal material. In addition, when the base material floats on seawater for a long time, salt crystals accumulate on a photo-thermal evaporation interface during evaporation, resulting in blockage of sunlight absorbing parts of the solar evaporator, and reduction of effective evaporation surface area, thereby reducing stability and durability thereof. Therefore, the solar steam generator should also have salt tolerance. Fortunately, materials with heat preservation, heat insulation, good light absorption performance and salt tolerance are greatly researched and developed to solve the problems, and the salt tolerance is further constructed. Therefore, the development of novel high-performance photo-thermal materials will become the main direction of future research.
Disclosure of Invention
In order to solve the problems in the prior art, the invention provides a preparation method of a polypyrrole modified carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel photo-thermal material and application thereof in sea water desalination and (containing heavy metal ions or dyes) wastewater purification treatment.
In order to achieve the above object, the present invention provides the following technical solutions:
the preparation method of the polypyrrole modified carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel photo-thermal material is characterized by comprising the following steps of:
step one, preparing a conjugated microporous polymer, which specifically comprises the following steps:
first, 1,3, 5-Triethynylbenzene, 1,3, 5-Tribromobenzene, cu I, pd (PPh 3 ) 2 C l 2 ，PPh 3 Sequentially added to toluene and Et 3 N in a round bottom flask;
the round bottom flask was then sealed and N was used 2 Protecting, and heating to 90 ℃ in an oil bath for reaction; after the reaction is finished, cooling the round-bottom flask to room temperature, performing suction filtration, and cleaning sequentially by using chloroform, toluene, water and methanol to obtain a solid;
finally, placing the obtained solid in a Soxhlet extractor, using methanol for extraction and cleaning, and vacuum drying at 60 ℃ to obtain a conjugated microporous polymer, which is named as CMP;
step two, preparing a sulfonated conjugated microporous polymer, which specifically comprises the following steps:
firstWill CH 2 C l 2 Adding a round bottom flask and cooling to 0 ℃ in an ice bath, adding the CMP obtained in the step one, stirring, and then adding CH containing chlorosulfonic acid 2 C l 2 Slowly heating to room temperature and continuously stirring;
then adding ice water to terminate the reaction, carrying out suction filtration, and washing with a large amount of water;
finally, vacuum drying at 45 ℃ to obtain a product sulfonated conjugated microporous polymer, which is named SCMP;
step three, preparing carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel, which specifically comprises the following steps:
firstly, preparing a carboxymethyl cellulose solution (CMC) with a certain concentration, then physically doping SCMP and CMC obtained in the second step, strongly stirring, standing, and eliminating bubbles;
then, putting the mixture into a refrigerator to freeze at the temperature of minus 20 ℃, and freeze-drying the mixture at the temperature of minus 50 ℃ to obtain carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel which is named CMC/SCMP;
the preparation of the polypyrrole modified carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel photo-thermal material specifically comprises the following steps:
first, a solution a was prepared: (NH) 4 ) 2 S 2 O 8 And deionized water are added into a spray bottle in sequence; preparing a solution B: pyrrole, isopropyl alcohol and phytic acid are sequentially added into a spray bottle;
then, after cooling the solution a and the solution B to 0 ℃, alternately spraying the solution B and the solution a on the top surface of CMC/SCMP to ensure complete coating by polypyrrole;
finally, after reacting at room temperature, washing with deionized water and drying at 60 ℃, obtaining the polypyrrole modified carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel photo-thermal material named CMC/SCMP-PPy.
Preferably, in the first step, the mass ratio of the 1,3, 5-tri-ethynyl benzene to the 1,3, 5-tribromobenzene is 1:1.
Preferably, in step two, the conjugated microporous polymer and chlorosulfonic acidThe mass (g) to volume (mL) ratio is
Preferably, in the third step, the mass ratio of the carboxymethyl cellulose to the sulfonated conjugated microporous polymer is 1.5:1.
preferably, in step three, the mixture is frozen in liquid nitrogen at a constant rate of 3-5mm/min.
Preferably, in the third step, the time of freeze-drying is 24 hours.
Preferably, in the fourth step, the mass ratio of pyrrole to phytic acid is 2:1.
the invention also provides application of the polypyrrole modified carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel photo-thermal material in sea water desalination and wastewater purification treatment (containing heavy metal ions or dyes).
Preferably, the polypyrrole modified carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel photo-thermal material is placed in seawater and wastewater (containing heavy metal ions or dyes) for sunlight irradiation.
The invention has the following beneficial effects: the invention firstly introduces a preparation method of polypyrrole modified carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel photo-thermal material capable of efficiently generating solar steam by taking sulfonation modification, physical doping, freeze drying and pyrrole in-situ polymerization as main means. And the application of the catalyst in sea water desalination and waste water purification treatment (containing heavy metal ions or dyes) is introduced. Through researches on the application of the polypyrrole modified carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel photo-thermal material, which can efficiently generate solar steam, is primarily considered to have higher solar energy conversion efficiency, excellent salt resistance and anti-fouling performance, and has a certain practical application value in the aspects of future sea water desalination and (containing heavy metal ions or dyes) wastewater purification treatment.
Drawings
In order to more clearly illustrate the technical solutions of the present invention, some drawings of the present invention will be briefly described below.
FIG. 1 is a preparation route diagram of polypyrrole modified carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel photo-thermal material capable of efficiently generating solar steam.
In fig. 2, a and c are scanning electron microscope images of CMP and SCMP. b and d are transmission electron microscopy images of CMP and SCMP. e is the energy spectrometer diagram of SCMP. f and g are scanning electron microscopy images of CMC and CMC/SCMP.
FIG. 3 is a graph of water contact angles for CMP, SCMP and CMC/SCMP in accordance with the present invention.
In fig. 4, a is a mercury/extrusion plot of CMC/SCMP and b is a macroporous diameter profile of CMC/SCMP.
In FIG. 5, a-b are scanning electron microscope images of CMC/SCMP and CMC/SCMP-PPy. c-f is the energy spectrum of CMC/SCMP-PPy.
In FIG. 6, a is the variation of pure water, CMC/SCMP and CMC/SCMP-PPy mass with time under different irradiation conditions. b is the evaporation rate and efficiency of pure water, CMC/SCMP and CMC/SCMP-PPy under different irradiation. c is the surface temperature of CMC/SCMP-PPy under different irradiation. d is an infrared image of CMC/SCMP-PPy under different irradiation.
In FIG. 7, a is at 1kW m -2 Under irradiation, the evaporation efficiency of CMC/SCMP-PPy was tested for 10 cycles. b is a comparison graph of solar evaporation efficiency reported in different relation.
In FIG. 8, a is a water evaporation mass loss profile for CMC/SCMP-PPy at different salinity. b is the evaporation rate and efficiency of CMC/SCMP-PPy at different salinity. c is at 1kW m -2 Under irradiation, CMC/SCMP-PPy surface NaCl quality change. d is the ion concentration in the simulated seawater before and after evaporation. And e is the resistance value of simulated seawater, purified water and drinking water.
In fig. 9, a is the ion concentration change before and after the metal ion evaporation. b-d are UV spectra of MB, MO and RhB solutions before and after evaporation.
Detailed Description
For more clearly illustrating the objects, technical solutions and advantages of the present invention, the functions and advantages of each module are explained in detail below with reference to the accompanying drawings.
The preparation method of the polypyrrole modified carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel photo-thermal material capable of efficiently generating solar steam is shown in figure 1.
FIG. 1 is a preparation route diagram of polypyrrole modified carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel photo-thermal material capable of efficiently generating solar steam.
The specific preparation method of the polypyrrole modified carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel photo-thermal material capable of efficiently generating solar steam comprises the following steps of:
EXAMPLE 1 preparation of carboxymethyl cellulose/sulfonated conjugated microporous Polymer composite aerogel (CMC/SCMP)
(1) Preparation of Conjugated Microporous Polymers (CMP)
First, 1,3, 5-Triethynylbenzene (1.50mmo l,0.2253g), 1,3, 5-tribromobenzene (1.50mmo l,0.4722g), cu I (0.11mmo l,0.0214g), pd (PPh 3 ) 2 Cl 2 (0.11mmo l，0.0790g)，PPh 3 (1.11mmo l,0.2950g) was added sequentially to toluene (35.0 mL) and Et 3 N (45.0 mL) in a round bottom flask. Thereafter, the device is sealed and N is used 2 And (3) protecting, and heating the oil bath to 90 ℃ for reaction for 20h. After the reaction was completed, the round-bottomed flask was cooled to room temperature, suction filtration was performed, and the obtained solid was washed with chloroform, toluene, water and methanol in this order. Finally, the obtained solid was placed in a Soxhlet extractor, washed with methanol extraction for 72 hours, and dried in vacuo at 60℃for 24 hours to obtain a conjugated microporous polymer, designated CMP.
(2) Preparation of Sulfonated Conjugated Microporous Polymer (SCMP)
50.0mL CH 2 C l 2 A round bottom flask was charged and cooled to 0deg.C in an ice bath, CMP (400.0 mg) was added and stirred for 10 min, followed by CH containing chlorosulfonic acid (4.0 mL) 2 C l 2 (10.0 mL) was slowly warmed to room temperature and stirred for 72h. Ice water was then added to terminate the reaction, suction filtered, and washed with a large amount of water. Finally vacuum drying for 12h at 45 ℃ to obtain the sulfonated conjugatedMicroporous polymer, designated SCMP.
(3) Preparation of carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel (CMC/SCMP)
2wt% of carboxymethyl cellulose (CMC) was prepared, 150.0mg of SCMP was added to CMC (500.0 mg), and the mixture was allowed to stand for 12 hours after intensive stirring for 4 hours, to thereby eliminate air bubbles. Freezing in a refrigerator at-20deg.C, and lyophilizing at-50deg.C for 24 hr to obtain carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel named CMC/SCMP.
The CMC/SCMP was prepared as a porous yellow cylinder 0.8cm high and 2.8cm in diameter.
In fig. 2, a and c are scanning electron microscope images of CMP and SCMP. b and d are transmission electron microscopy images of CMP and SCMP. e is the energy spectrometer diagram of SCMP. f and g are scanning electron microscopy images of CMC and CMC/SCMP.
Fig. 2 is a view of the surface morphology of CMP, SCMP and CMC/SCMP by scanning electron microscopy and transmission electron microscopy. Figures 2a-d show that CMP and SCMP are amorphous structures. And the results indicate that the sulfonation reaction has no effect on the overall structure of the CMP. Fig. 2e is a spectrometer diagram of SCMP. It can be seen that C, O, S elements in the SCMP are uniformly distributed, and a basis is provided for successful sulfonation reaction. FIGS. 2f-g show that CMC and CMC/SCMP have a porous structure, and that CMC/SCMP surfaces are covered by SCMP.
Fig. 3 is water contact angles for CMP, SCMP and CMC/SCMP.
Figure 3 the wettability of CMP, SCMP and CMC/SCMP was investigated using a water contact angle meter. The water contact angle of CMP after sulfonation modification was 139.5 °, and the water contact angle of SCMP was 0 °. The results indicate that CMP becomes hydrophilic after sulfonation. And the CMC/SCMP has a water contact angle of 0 degrees, and has super-hydrophilic property and is beneficial to water transmission.
In fig. 4, a is a mercury/extrusion plot of CMC/SCMP and b is a macroporous diameter profile of CMC/SCMP.
As shown in FIGS. 4a-b, the porosity properties of CMC/SCMP were studied by mercury porosimetry. The CMC/SCMP has a cumulative pore size of 0-30 μm, a porosity of 91.02%, an average pore size of 4.28 μm and a total pore area of 10.52m 2 g -1 . Results demonstrate that CMC/SCMP has a richRich macroporous structure.
EXAMPLE 2 preparation of polypyrrole-modified carboxymethyl cellulose/sulfonated conjugated microporous Polymer composite aerogel photo-thermal Material (CMC/SCMP-PPy)
(1) Preparation of carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel (CMC/SCMP): as in example 1.
(2) First, preparing a solution A:1.37g (NH) 4 ) 2 S 2 O 8 And 25.0mL deionized water were added sequentially to a 10.0mL spray bottle; preparing a solution B:0.42mL pyrrole, 25.0mL isopropanol, and 0.92mL phytic acid were added sequentially to a 10.0mL spray bottle. Next, after cooling to 0 ℃, solutions B and a were sprayed alternately on top of CMC/SCMP, ensuring complete coating by polypyrrole. And (3) reacting for 1h at room temperature, washing with deionized water for several times, and drying at 60 ℃ to obtain the polypyrrole modified carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel named CMC/SCMP-PPy.
In FIG. 5, a-b are scanning electron microscope images of CMC/SCMP and CMC/SCMP-PPy. c-f is the energy spectrum of CMC/SCMP-PPy.
Fig. 5a-b show scanning electron microscope images of CMC/SCMP and CMC/SCMP-PPy, which can be seen that both have obvious pore structures, and the pore channels are not blocked after polypyrrole is sprayed on the CMC/SCMP surface, thus laying a foundation for the subsequent interfacial evaporation performance. Fig. 5c-f confirm PPy coating on CMC/SCMP-PPy by energy spectrometer analysis, showing PPy deposition on CMC/SCMP, while the original structure is significantly preserved by the presence of C, O and S (basic structural units of CMC/SCMP).
Example 3 application of the polypyrrole-modified carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel photo-thermal material capable of efficiently generating solar steam in simulating sea water desalination and wastewater purification treatment (containing heavy metal ions or dyes)
(1) CMC/SCMP prepared in example 1 and CMC/SCMP-PPy prepared in example 2 were placed in different pure water environments, respectively, in 1 sun (1 kW/m 2 ) Irradiating for 60 minutes. The evaporation performance of the solar heat collector is tested by using a laboratory simulated solar test device system. Wherein the day is analyzed by electronThe quality change of water in the system is monitored in real time, and the temperature change of the top of the material is monitored by utilizing an infrared photography technology. The evaporation rate and evaporation efficiency of CMC/SCMP and CMC/SCMP-PPy can be obtained according to the slope of the curve of the mass change with time. The CMC/SCMP-PPy was tested for 10 evaporation efficiencies at 1 sun and compared to the evaporation efficiencies of the materials in other literature.
In FIG. 6, a is the variation of pure water, CMC/SCMP and CMC/SCMP-PPy mass with time under different irradiation conditions. b is the evaporation rate and efficiency of pure water, CMC/SCMP and CMC/SCMP-PPy under different irradiation. c is the surface temperature of CMC/SCMP-PPy under different irradiation. d is an infrared image of CMC/SCMP-PPy under different irradiation.
As shown in FIG. 6a, at 1kW m -2 Under irradiation, the evaporation rates of CMC/SCMP and CMC/SCMP-PPy respectively reach 0.52kg m according to the pure water obtained by calculating the slope of the mass change curve -2 h -1 、0.88kg m -2 h -1 、1.44kg m -2 h -1 . In contrast, CMC/SCMP-PPy has a high evaporation rate, since the photo-thermal conversion efficiency of CMC/SCMP-PPy is enhanced after spraying polypyrrole. Thereafter, at 2kW m -2 And 3kW m -2 Under irradiation, CMC/SCMP-PPy evaporation rates were 2.24kg m respectively -2 h -1 、3.01kg m -2 h -1 . Calculated by an energy conversion efficiency equation, FIG. 6b shows the energy conversion efficiency at 1kW m -2 Under irradiation, the evaporation efficiencies of pure water, CMC/SCMP and CMC/SCMP-PPy are respectively 20.82%, 45.14% and 85.57%, and CMC/SCMP-PPy is better than CMC/SCMP. At 2kW m -2 And 3kW m -2 Under irradiation, CMC/SCMP-PPy evaporation efficiencies were 70.30% and 65.28%, respectively. In addition, in order to intensively study the photo-thermal conversion performance of CMC/SCMP-PPy, the change of the surface temperature of CMC/SCMP-PPy with time was recorded by a thermal infrared camera (fig. 6c and 6 d), and as a result, it was revealed that the surface temperature of CMC/SCMP-PPy was rapidly increased first and then gradually smoothed with time. CMC/SCMP-PPy at 1kW m -2 The surface temperature of 10 min and 30 min reaches 40.4 ℃,41.8 ℃ and 2kW m respectively under irradiation -2 The surface temperature of 10 min and 30 min reaches 45.2 ℃,48.2 ℃ and 3kW m respectively under irradiation -2 The surface temperatures of 10 min and 30 min reach 50.8 ℃ and 54.0 ℃ respectively under irradiation.
In FIG. 7, a is at 1kW m -2 Under irradiation, the evaporation efficiency of CMC/SCMP-PPy was tested for 10 cycles. b is a comparison graph of solar evaporation efficiency reported in different relation.
FIG. 7a shows the reaction at 1kW m -2 The pure water interface evaporation experiment is carried out for 10 times under irradiation, so that the evaporation efficiency can be kept stable, and the method is suitable for practical application. FIG. 7b shows that CMC/SCMP-PPy has a strong photo-thermal effect with evaporation efficiency comparable to that of the previously reported 1kW m -2 The other solar evaporators under irradiation are equivalent.
(2) CMC/SCMP-PPy was placed in simulated seawater and 5% salinity, 10% NaCl brine at 1 sun (1 kW/m 2 ) The evaporation rate and evaporation efficiency of CMC/SCMP-PPy can be obtained according to the slope of the curve of the mass change with time after irradiation for 60 minutes. The disappearance time of NaCl particles was observed by placing 0.5g of NaCl particles on the CMC/SCMP-PPy surface. CMC/SCMP-PPy was placed in simulated seawater for interfacial evaporation and the evaporated condensate was collected for ion concentration testing. Simulating Na existing in sea water + 、Mg 2+ 、Ca 2+ And K + Ion concentrations are 10473mg L respectively -1 、6825mg L -1 、397mg L -1 And 380mg L -1 . And the resistance values of the simulated seawater, the purified water and the drinking water are tested and compared.
In FIG. 8, a is a water evaporation mass loss profile for CMC/SCMP-PPy at different salinity. b is the evaporation rate and efficiency of CMC/SCMP-PPy at different salinity. c is at 1kW m -2 Under irradiation, CMC/SCMP-PPy surface NaCl quality change. d is the ion concentration in the simulated seawater before and after evaporation. And e is the resistance value of simulated seawater, purified water and drinking water.
As shown in FIGS. 8a-b, the evaporation rates of CMC/SCMP-PPy in simulated seawater, 5% and 10% NaCl solutions, respectively, were up to 1.43kg m -2 h -1 、1.39kg m -2 h -1 And 1.33kg m -2 h -1 The evaporation efficiency reaches 83.13%, 81.25% and 77.20%, respectively. As shown in FIG. 8c, in CMC/SCMP-PPy evaporatorAfter 1h, no salt particles were deposited on the evaporator surface, indicating that CMC/SCMP-PPy had a salt self-cleaning effect. As shown in FIG. 8d, na was analyzed using inductively coupled plasma optical emission spectroscopy (ICP-OES) + 、Mg 2+ 、Ca 2+ And K + Concentration of ions. Na in simulated seawater + 、Mg 2 + 、Ca 2+ And K + Ion concentrations are 10473mg L respectively -1 、6825mg L -1 、397mg L -1 And 380mg L -1 In the collected purified water, the concentrations of the four cations were all drastically reduced, 5.53mg L each -1 、1.27mg L -1 、1.40mg L -1 And 3.46mg L -1 The cation concentration is far lower than the drinking water standard established by the world health organization, which shows that CMC/SCMP-PPy is excellent in sea water desalination. Fig. 8e shows the resistance values of simulated seawater, purified water and potable water. After CMC/SCMP-PPy solar interfacial evaporation, the resistance value was changed from 46.4kΩ to 1.3mΩ, which is close to the resistance value of potable water (1.2 mΩ), due to the reduced concentration of dissolved salts in the simulated seawater.
(3) CMC/SCMP-PPy was placed in heavy metal ion (Cu 2+ 、Cr 3+ 、Pb 2+ And Zn 2+ ) Or performing interfacial evaporation in aqueous solution of dye (MB, MO and RhB), collecting evaporated condensate, and detecting heavy metal ion (Cu) with inductively coupled plasma emission spectrum and ultraviolet-visible spectrophotometer 2+ 、Cr 3+ 、Pb 2+ And Zn 2+ ) Or the concentration of the dyes (MB, MO and RhB).
In fig. 9, a is the ion concentration change before and after the metal ion evaporation. b-d are UV spectra of MB, MO and RhB solutions before and after evaporation.
As shown in fig. 9a, a sharp drop in concentration of all heavy metal ions was observed by comparing the concentration of metal ions before and after evaporation of the sun, further demonstrating the effectiveness of CMC/SCMP-PPy aerogel for purification of wastewater containing heavy metal ions. Fig. 9b-d clearly show that no characteristic absorption peak of dye appears in distilled water after interfacial evaporation, indicating that CMC/SCMP-PPy aerogel has excellent purification ability for dye wastewater.
The foregoing has outlined the basic principles, features, and advantages of the present invention. It will be appreciated by those skilled in the relevant art that the invention is not limited by the foregoing examples, which are presented in the foregoing examples and description merely to illustrate the principles of the invention. The invention can be applied to any other field with optimized properties. The invention is subject to various changes and modifications which fall within the scope of the invention as claimed. The scope of the invention is defined by the appended claims and equivalents thereof.
Claims (10)
1. The preparation method of the polypyrrole modified carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel photo-thermal material is characterized by comprising the following steps of:
step one, preparing a conjugated microporous polymer;
step two, preparing a sulfonated conjugated microporous polymer;
step three, preparing carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel;
and step four, preparing the polypyrrole modified carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel photo-thermal material.
2. The method for preparing the polypyrrole modified carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel photo-thermal material according to claim 1, wherein in the first step, the preparation of the conjugated microporous polymer comprises the following steps:
first, 1,3, 5-Triethynylbenzene, 1,3, 5-Tribromobenzene, cuI, pd (PPh 3 ) 2 Cl 2 ，PPh 3 Sequentially added to toluene and Et 3 N in a round bottom flask;
the round bottom flask was then sealed and N was used 2 Protecting, and heating to 90 ℃ in an oil bath for reaction; after the reaction is finished, cooling the round-bottom flask to room temperature, performing suction filtration, and cleaning sequentially by using chloroform, toluene, water and methanol to obtain a solid;
finally, the obtained solid is placed in a Soxhlet extractor, extracted and cleaned by methanol, and dried in vacuum at 60 ℃ to obtain a conjugated microporous polymer, which is named as CMP.
3. The method for preparing the polypyrrole modified carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel photo-thermal material according to claim 2, wherein in the second step, the preparation of the sulfonated conjugated microporous polymer specifically comprises the following steps:
first, CH is to 2 Cl 2 Adding a round bottom flask and cooling to 0 ℃ in an ice bath, adding CMP stirring, followed by adding CH containing chlorosulfonic acid 2 Cl 2 Slowly heating to room temperature and continuously stirring;
then adding ice water to terminate the reaction, carrying out suction filtration, and washing with a large amount of water;
finally, the product sulfonated conjugated microporous polymer is obtained by vacuum drying at 45 ℃, and is named as SCMP.
4. The method for preparing the polypyrrole modified carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel photo-thermal material according to claim 3, wherein in the third step, the preparation of the carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel specifically comprises the following steps:
firstly, preparing a carboxymethyl cellulose solution (CMC) with a certain concentration, physically doping SCMP and CMC, strongly stirring, standing, and eliminating bubbles;
then, putting the mixture into a refrigerator to freeze at the temperature of minus 20 ℃, and freeze-drying the mixture for 24 hours at the temperature of minus 50 ℃ to obtain the carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel which is named CMC/SCMP.
5. The method for preparing the polypyrrole modified carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel photo-thermal material according to claim 4, wherein in the fourth step, the preparation of the polypyrrole modified carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel photo-thermal material specifically comprises the following steps:
first, a solution a was prepared: (NH) 4 ) 2 S 2 O 8 And deionized water are added into a spray bottle in sequence; preparing a solution B: pyrrole, isopropyl alcohol and phytic acid are sequentially added into a spray bottle, and the mass ratio of the pyrrole to the phytic acid is 2:1, a step of;
then, after cooling the solution a and the solution B to 0 ℃, alternately spraying the solution B and the solution a on the top surface of CMC/SCMP to ensure complete coating by polypyrrole;
finally, after reacting at room temperature, washing with deionized water and drying at 60 ℃, obtaining the polypyrrole modified carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel photo-thermal material named CMC/SCMP-PPy.
6. The preparation method of the polypyrrole modified carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel photo-thermal material according to claim 2, wherein the mass ratio of the 1,3, 5-tri-ethynyl benzene to the 1,3, 5-tribromobenzene is 1:1.
7. The method for preparing the polypyrrole modified carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel photo-thermal material according to claim 3, wherein the mass (g) and volume (mL) ratio of the conjugated microporous polymer to chlorosulfonic acid is 1:10.
8. the method for preparing the polypyrrole modified carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel photo-thermal material according to claim 4, wherein the mass ratio of the carboxymethyl cellulose to the sulfonated conjugated microporous polymer is 1.5:1.
9. the method for preparing the polypyrrole modified carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel photo-thermal material according to claim 4, wherein the speed is 3-5mm/min when the mixture is frozen in liquid nitrogen at a constant speed.
10. The application of the polypyrrole modified carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel photo-thermal material obtained in the claims 1-9 in sea water desalination and waste water purification treatment of heavy metal ions or dyes, specifically, the polypyrrole modified carboxymethyl cellulose/sulfonated conjugated microporous polymer composite aerogel photo-thermal material is placed in sea water and waste water containing heavy metal ions or dyes for sunlight irradiation.
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