CN106751814A - A kind of polyaniline silicon based composite material and preparation method and application - Google Patents
A kind of polyaniline silicon based composite material and preparation method and application Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L79/00—Compositions 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 C08L61/00 - C08L77/00
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- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/26—Synthetic macromolecular compounds
- B01J20/264—Synthetic macromolecular compounds derived from different types of monomers, e.g. linear or branched copolymers, block copolymers, graft copolymers
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- 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
- C02F1/28—Treatment of water, waste water, or sewage by sorption
- C02F1/285—Treatment of water, waste water, or sewage by sorption using synthetic organic sorbents
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Abstract
The invention belongs to pollution control field, more particularly to a kind of polyaniline silicon based composite material and preparation method and application.The invention provides a kind of polyaniline silicon based composite material, including：Polyaniline and cage-type silsesquioxane；It is polyaniline grafted on cage-type silsesquioxane.Present invention also offers a kind of preparation method of above-mentioned polyaniline silicon based composite material, it is：Living polymer preparation, halogenation and polymerization.A kind of application of the product obtained present invention also offers above-mentioned polyaniline silicon based composite material or above-mentioned preparation method in heavy metal adsorption field.By product obtained in the technical scheme that the present invention is provided, the mechanical strength and processing characteristics of polyaniline material are effectively improved, the adsorption capacity for heavy metal is good, solves in the prior art, the polyaniline technological deficiency poor for the adsorption capacity of heavy metal.The technical scheme that the present invention is provided, also has the advantages that preparation process is simple and easily operated, the large-scale promotion of suitable industrial circle.
Description
Technical field
The invention belongs to pollution control field, more particularly to a kind of polyaniline-silicon based composite material and preparation method thereof with
Using.
Background technology
It is heavy metal-polluted to have a finger in every pie the environmental pollution caused by heavy metal or its compound, mainly by mining, waste gas discharge, sewage
Caused by the human factor such as irrigation and use heavy metals exceeding standard product.The metal that heavy metal refers to proportion more than 5, including gold, silver,
Copper, iron, lead etc..Heavy metal pollution is different from the pollution of other organic compounds, and many organic compounds can be by nature
The purification of physics itself, chemistry or biology, makes harmfulness reduction or releases；And heavy metal has enriching, it is difficult in ring
Degraded in border.At present, China due in the exploitation of heavy metal, smelting, process, cause many heavy metals for example lead, mercury,
Cadmium, cobalt etc. cause serious environmental pollution into big gas and water, soil.With the heavy metal that waste water is discharged, even if concentration is small, also may be used
Accumulated in algae and bed mud, adsorbed by fish and shellfish body surface, food chain concentration is produced, so as to cause public hazards.Therefore, in water body
The pollution control of heavy metal, has become a severe problem for attracting attention extensively.
In the prior art, the heavy metal for coming in adsorption treatment water body usually using the method for absorption.Polyaniline material
(PANI) have substantial amounts of amino and imido grpup function in molecule, heavy metal ion has good complexing, can also with
There is redox reaction absorption in some oxidizing potentials heavy metal ion higher, PANI classes adsorbent can be widely applicable to respectively
Plant complicated absorption environment.Simultaneously as polyaniline be also easy to get with raw material monomer, it is cheap, be readily synthesized and have
The advantage of good environmental stability so that the heavy metal adsorption performance study of polyaniline turns into one of focus gradually.However, by
General organic solvent is not dissolved in polyaniline material, machinability and mechanical performance are poor, limit polyaniline for a huge sum of money
The adsorption capacity of category.
Therefore, a kind of polyaniline-silicon based composite material and preparation method and application is developed, for solving prior art
In, the polyaniline technological deficiency poor for the adsorption capacity of heavy metal becomes those skilled in the art's problem demanding prompt solution.
The content of the invention
In view of this, the invention provides a kind of polyaniline-silicon based composite material and preparation method and application, for solving
Certainly in the prior art, the polyaniline technological deficiency poor for the adsorption capacity of heavy metal.
The invention provides a kind of polyaniline-silicon based composite material, the composite includes：Polyaniline and cage model sesquialter
Siloxanes；
It is described polyaniline grafted on the cage-type silsesquioxane.
Present invention also offers a kind of preparation method of above-mentioned polyaniline-silicon based composite material, the preparation method is：
It is prepared by step one, living polymer：Methacrylic acid diaminourea ethyl ester, 4- cyanopentanoic acids dithiobenzoic acid and idol
Nitrogen bis-isobutyronitrile is dissolved in solvent, is purified after reaction, dried, and obtains the first product；
Step 2, chloride：First product and halogenation sulfone mix, by the chain end group-COOH in first product
It is changed into-COCl, obtains the second product；
Step 3, grafting：There is graft reaction in second product and eight aminophenyl cage-type silsesquioxanes, after purification
Dry, obtain third product；
Step 4, polymerization：The third product, aniline and ammonium persulfate are dissolved in solvent, and product is obtained after stirring.
Preferably, in terms of molar part, the methacrylic acid diaminourea ethyl ester, 4- cyanopentanoic acids dithiobenzoic acid and idol
The rate of charge of nitrogen bis-isobutyronitrile is (10~40):1:(0.05~0.2).
Preferably, in terms of molar part, the methacrylic acid diaminourea ethyl ester, 4- cyanopentanoic acids dithiobenzoic acid and idol
The rate of charge of nitrogen bis-isobutyronitrile is 20:1:0.1.
Preferably, the reaction described in step one is carried out under conditions of nitrogen protection；
The temperature reacted described in step one is 60-70 DEG C, and the time reacted described in step one is 3-6h.
Preferably, the temperature reacted described in step one is 65 DEG C, and the time reacted described in step one is 4h.
Preferably, the halogenation sulfone described in step 2 is thionyl chloride.
Preferably, in terms of molar part, the rate of charge of second product and eight aminophenyl cage-type silsesquioxanes is (6
~1):1.
Preferably, in terms of molar part, the rate of charge of second product and eight aminophenyl cage-type silsesquioxanes is 4:
1。
Preferably, the time of graft reaction described in step 3 is 6~12h.
Preferably, the time of graft reaction described in step 3 is 8h.
Preferably, in terms of molar part, the rate of charge of third product and aniline is 1:(10~80).
Preferably, in terms of molar part, the rate of charge of third product and aniline is 1:40；
The temperature stirred described in step 4 is 0~5 DEG C, and the time stirred described in step 4 is 8~12h.
Preferably, the temperature for being stirred described in step 4 is 0 DEG C, and the time stirred described in step 4 is 10h.
Preferably, the solvent described in step one is selected from：In dioxane, tetrahydrofuran, dichloromethane and methyl alcohol one
Plant or various, the solvent described in step 4 is HCl/water solution；
The dry method is vacuum drying.
Present invention also offers the preparation method described in a kind of above-mentioned polyaniline-silicon based composite material or more any one
Application of the product for obtaining in heavy metal adsorption field.
In sum, the invention provides a kind of polyaniline-silicon based composite material, the composite includes：Polyaniline
And cage-type silsesquioxane；It is described polyaniline grafted on the cage-type silsesquioxane.It is above-mentioned present invention also offers one kind
The preparation method of polyaniline-silicon based composite material, the preparation method is：It is prepared by step one, living polymer；Step 2, halogen
Change；Step 3, grafting；Step 4, polymerization.Present invention also offers a kind of above-mentioned polyaniline-silicon based composite material or above-mentioned system
Application of the product that Preparation Method is obtained in heavy metal adsorption field.By product obtained in the technical scheme that the present invention is provided, have
Effect improves the mechanical strength and processing characteristics of polyaniline material, and through experimental tests can be obtained, and the adsorption capacity for heavy metal is good
It is good, solve in the prior art, the polyaniline technological deficiency poor for the adsorption capacity of heavy metal.The technical side that the present invention is provided
Case, also has the advantages that preparation process is simple and easily operated, the large-scale promotion of suitable industrial circle.
Brief description of the drawings
In order to illustrate more clearly about the embodiment of the present invention or technical scheme of the prior art, below will be to embodiment or existing
The accompanying drawing to be used needed for having technology description is briefly described, it should be apparent that, drawings in the following description are only this
Inventive embodiment, for those of ordinary skill in the art, on the premise of not paying creative work, can also basis
The accompanying drawing of offer obtains other accompanying drawings.
A kind of preparation flow schematic diagram of the preparation method of polyaniline-silicon based composite material that Fig. 1 is provided for the present invention；
Fig. 2 is a kind of infrared spectrum schematic diagram of polyaniline-silicon based composite material obtained in the present invention；
Fig. 3 is a kind of close-up schematic view of the infrared spectrum of polyaniline-silicon based composite material obtained in the present invention；
Fig. 4 is a kind of thermogravimetric analysis figure of polyaniline-silicon based composite material obtained in the present invention.
Specific embodiment
The invention provides a kind of polyaniline-silicon based composite material and preparation method and application, for solving existing skill
In art, the polyaniline technological deficiency poor for the adsorption capacity of heavy metal.
The technical scheme in the embodiment of the present invention will be clearly and completely described below, it is clear that described implementation
Example is only a part of embodiment of the invention, rather than whole embodiments.Based on the embodiment in the present invention, this area is common
The every other embodiment that technical staff is obtained under the premise of creative work is not made, belongs to the model of present invention protection
Enclose.
In order to the present invention is described in more detail, a kind of polyaniline-silicon substrate that the present invention is provided is combined with reference to embodiment
Material and preparation method and application, is specifically described.
Embodiment 1
It is prepared by step one, living polymer
16mmol methacrylic acid diaminourea ethyl ester, 0.4mmol4- cyanopentanoic acids dithiobenzoic acid and 2mmol azos two
Isobutyronitrile is dissolved in 10mL dioxane, nitrogen charging gas shielded after reaction system freezing degassing, under the conditions of 60 DEG C, is stopped after reaction 4h
Only react.Precipitation in excessive oil ether is instilled, is vacuum dried 12 hours at 50 DEG C, obtain the first product 1.
Step 2, chloride
The first products of 0.2mmol 1 and 10mL chlorinations sulfone mix, in the first product 1 chain end group-COOH is changed into-
COCl, obtains the second product 1.
Step 3, grafting
To there is grafting in the second products of 0.2mmol 1 anti-at room temperature with the aminophenyl cage-type silsesquioxanes of 0.2mmol eight
Should, the 8h of graft reaction.After stopping reaction, precipitation in excessive oil ether is instilled, be vacuum dried 12 hours at 50 DEG C, obtain the 3rd
Product 1.
Step 4, polymerization
0.2mmol third products 1,2mmol aniline and 0.5wt% ammonium persulfates are dissolved in the HCl that concentration is 1M, at 0 DEG C
Under the conditions of, 10h is reacted, bottle green product is collected by filtration, obtain product 1.
Embodiment 2
It is prepared by step one, living polymer
8mmol methacrylic acid diaminourea ethyl ester, 0.4mmol4- cyanopentanoic acids dithiobenzoic acid and 0.1m mol azos
Bis-isobutyronitrile is dissolved in 10mL dioxane, nitrogen charging gas shielded after reaction system freezing degassing, under the conditions of 60 DEG C, after reaction 4h
Stop reaction.Precipitation in excessive oil ether is instilled, is vacuum dried 12 hours at 50 DEG C, obtain the first product 2.
Step 2, chloride
The first products of 0.2mmol 2 and 10mL chlorinations sulfone mix, in the first product 2 chain end group-COOH is changed into-
COCl, obtains the second product 2.
Step 3, grafting
To there is grafting in the second products of 0.2mmol 2 anti-at room temperature with the aminophenyl cage-type silsesquioxanes of 0.1mmol eight
Should, the 8h of graft reaction.After stopping reaction, precipitation in excessive oil ether is instilled, be vacuum dried 12 hours at 50 DEG C, obtain tertiary industry
Thing 2.
Step 4, polymerization
0.2mmol third products 2,4mmol aniline and 0.5wt% ammonium persulfates are dissolved in the HCl that concentration is 1M, at 0 DEG C
Under the conditions of, 10h is reacted, bottle green product is collected by filtration, obtain product 2.
Embodiment 3
It is prepared by step one, living polymer
4mmol methacrylic acid diaminourea ethyl ester, 0.4mmol4- cyanopentanoic acids dithiobenzoic acid and 0.05mmol azos
Bis-isobutyronitrile is dissolved in 10mL dioxane, nitrogen charging gas shielded after reaction system freezing degassing, under the conditions of 60 DEG C, after reaction 4h
Stop reaction.Precipitation in excessive oil ether is instilled, is vacuum dried 12 hours at 50 DEG C, obtain the first product 3.
Step 2, chloride
The first products of 0.2mmol 3 and 10mL chlorinations sulfone mix, in the first product 3 chain end group-COOH is changed into-
COCl, obtains the second product 3.
Step 3, grafting
To there is grafting in the second products of 0.6mmol 1 anti-at room temperature with the aminophenyl cage-type silsesquioxanes of 0.1mmol eight
Should, the 8h of graft reaction.After stopping reaction, precipitation in excessive oil ether is instilled, be vacuum dried 12 hours at 50 DEG C, obtain tertiary industry
Thing 3.
Step 4, polymerization
0.2mmol third products 2,8mmol aniline and 0.5wt% ammonium persulfates are dissolved in the HCl that concentration is 1M, at 0 DEG C
Under the conditions of, 10h is reacted, bottle green product is collected by filtration, obtain product 3.
Embodiment 4
The present embodiment is the specific embodiment of the structure verification of product 1~3 and performance detection obtained in embodiment 1~3.
Infrared spectrum detection is carried out to 1~product of product 3, gained testing result refers to Fig. 2 and Fig. 3.From infrared spectrum
In can draw, 1567cm-1And 1487cm-1It is the characteristic peak of phenyl ring, wherein 1567cm-1Place peak is quinoid structure N=Q=N
Absorb vibration, 1487cm-1It is the characteristic absorption vibration of benzene formula structure N-B-N；1112cm-1It is the in-plane bending vibration of phenyl ring；And
And, 1140cm-1Place's peak type broadens, relative intensity enhancing, and this is the effect due to Si-O-Si.Therefore, can sentence from Fig. 2 and Fig. 3
Fixed, product 1~3 obtained in 1~embodiment of embodiment 3 is goal-selling product.
Please in the experimentation of supplemental heat weight analysis herein.Thermogravimetric analysis, intensification heating rate are carried out in nitrogen atmosphere
10 DEG C/min, 50~800 DEG C of Range of measuring temp.Experimental result according to obtained by thermogravimetric analysis see Fig. 4, can be with from Fig. 4
Draw, product 1~3 obtained in 1~embodiment of embodiment 3 has good heat-resistant stability.
The structure of product 1~3 obtained in 1~embodiment of electric Microscopic observation embodiment 3, it can be seen that product 1~3 is formed
Obvious level loose structure polyaniline composite material.The scattered electron microscope in ethanol of product 1~3, can be visually seen
The dispersive property of the prepared porous polyaniline composite material of new level has larger improvement.
The present embodiment is the specific implementation determined for heavy metal adsorption of product 1~3 obtained in embodiment 1~3
Example.
Heavy metal ion adsorbed experiment is carried out to 1~product of product 3.Experiment condition:Adsorbent amount:0.02g,Pb(II)
Concentration:10mg L–1,pH:6.0.Investigate the influence to adsorption rate in the range of duration of oscillation 10min -210min.Result shows, produces
1~product of product 3 has the rate of adsorption fast (reaching saturated extent of adsorption in 30 minutes), and adsorbance is big, and (adsorbance is respectively 135.0mg
g-1、138.0mg g-1And 142.0mg g-1) the characteristics of, and with magnetic response characteristic.The technical scheme provided by the present invention
Obtained product, the adsorption capacity for heavy metal is good.
In sum, the invention provides a kind of polyaniline-silicon based composite material, the composite includes：Polyaniline
And cage-type silsesquioxane；It is described polyaniline grafted on the cage-type silsesquioxane.It is above-mentioned present invention also offers one kind
The preparation method of polyaniline-silicon based composite material, the preparation method is：It is prepared by step one, living polymer；Step 2, acyl
Chlorination；Step 3, grafting；Step 4, polymerization.Present invention also offers a kind of above-mentioned polyaniline-silicon based composite material or above-mentioned
Application of the product that preparation method is obtained in heavy metal adsorption field.By product obtained in the technical scheme that the present invention is provided,
The mechanical strength and processing characteristics of polyaniline material are effectively improved, through experimental tests can be obtained, for the adsorption capacity of heavy metal
Well, solve in the prior art, the polyaniline technological deficiency poor for the adsorption capacity of heavy metal.The technology that the present invention is provided
Scheme, also has the advantages that preparation process is simple and easily operated, the large-scale promotion of suitable industrial circle.
The above is only the preferred embodiment of the present invention, it is noted that for the ordinary skill people of the art
For member, under the premise without departing from the principles of the invention, some improvements and modifications can also be made, these improvements and modifications also should
It is considered as protection scope of the present invention.
Claims (10)
1. a kind of polyaniline-silicon based composite material, it is characterised in that the composite includes：Polyaniline and cage model sesquialter silicon
Oxygen alkane；
It is described polyaniline grafted on the cage-type silsesquioxane.
2. a kind of preparation method including polyaniline-silicon based composite material described in claim 1, it is characterised in that the preparation
Method is：
It is prepared by step one, living polymer：Methacrylic acid diaminourea ethyl ester, 4- cyanopentanoic acids dithiobenzoic acid and azo two
Isobutyronitrile is dissolved in solvent, is purified after reaction, dried, and obtains the first product；
Step 2, chloride：First product and halogenation sulfone mix, and the chain end group in first product-COOH is become
It is-COCl, obtains the second product；
Step 3, grafting：There is graft reaction in second product and eight aminophenyl cage-type silsesquioxanes, done after purification
It is dry, obtain third product；
Step 4, polymerization：The third product, aniline and ammonium persulfate are dissolved in solvent, and product is obtained after stirring.
3. preparation method according to claim 2, it is characterised in that in terms of molar part, the methacrylic acid diaminourea
The rate of charge of ethyl ester, 4- cyanopentanoic acids dithiobenzoic acid and azodiisobutyronitrile is (10~40):1:(0.05~0.2).
4. preparation method according to claim 2, it is characterised in that the condition that the reaction described in step one is protected in nitrogen
Under carry out；
The temperature reacted described in step one is 60~70 DEG C, and the time reacted described in step one is 3~6h.
5. preparation method according to claim 2, it is characterised in that the halogenation sulfone described in step 2 is thionyl chloride.
6. preparation method according to claim 2, it is characterised in that in terms of molar part, second product and eight amino
The rate of charge of phenyl cage-type silsesquioxane is (6~1):1.
7. preparation method according to claim 2, it is characterised in that the time of graft reaction described in step 3 is 3-6h
(being not required to mechanical agitation).
8. preparation method according to claim 2, it is characterised in that in terms of molar part, third product, aniline and persulfuric acid
The rate of charge of ammonium is 1:(10~80), ammonium persulfate is the 0.5% of monomer mass；
The temperature stirred described in step 4 is 0~5 DEG C, and the time stirred described in step 4 is 8~12h.
9. preparation method according to claim 2, it is characterised in that the solvent described in step one is selected from：Dioxane, four
One or more in hydrogen furans, dichloromethane and methyl alcohol, the solvent described in step 4 is HCl/water solution；
The dry method is vacuum drying.
10. described in a kind of polyaniline-silicon based composite material or claim 2 to 9 any one including described in claim 1
Application of the product that preparation method is obtained in heavy metal adsorption field.
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| CN107583629A (en) * | 2017-09-08 | 2018-01-16 | 中山大学 | Solid phase micro extraction probe prepared using octaphenyl cage-type silsesquioxane as material and its preparation method and application |
| CN112657469A (en) * | 2020-12-03 | 2021-04-16 | 山东大学 | Preparation method of amino-functionalized silsesquioxane-based heavy metal ion adsorbent |
| CN113559828A (en) * | 2021-07-30 | 2021-10-29 | 中国农业科学院农业质量标准与检测技术研究所 | Polyacrylic acid magnetic nano composite material, preparation method and application |
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| CN112657469A (en) * | 2020-12-03 | 2021-04-16 | 山东大学 | Preparation method of amino-functionalized silsesquioxane-based heavy metal ion adsorbent |
| CN113559828A (en) * | 2021-07-30 | 2021-10-29 | 中国农业科学院农业质量标准与检测技术研究所 | Polyacrylic acid magnetic nano composite material, preparation method and application |
| CN113559828B (en) * | 2021-07-30 | 2023-05-26 | 中国农业科学院农业质量标准与检测技术研究所 | Polyacrylic acid magnetic nanocomposite, preparation method and application |
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