CN103570944B - Polyaniline containing sulfydryl and preparation method thereof - Google Patents
Polyaniline containing sulfydryl and preparation method thereof Download PDFInfo
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Abstract
The invention provides a kind of polyaniline containing sulfydryl and preparation method thereof, belong to method for preparing polyaniline field.Solve in preparation method's process of the existing polyaniline containing sulfydryl, the problem of oxidized dose of sulfydryl oxidation.Aniline monomer containing sulfydryl first dissolves in organic solvent by the method, obtains the first mixing solutions; Oxygenant is dissolved in inorganic acid aqueous solution, obtains the second mixing solutions; By the first mixing solutions and the mixing of the second mixing solutions, the aniline monomer containing sulfydryl is polymerized at water-organic solvent interface, obtains reaction product; Reaction product is obtained after washing, alcohol wash, drying the polyaniline containing sulfydryl.By the polyaniline that aforesaid method obtains, make the sulfydryl in preparation process can not dioxygen oxidation in oxidized dose and air, experimental result shows: the polyaniline number-average molecular weight containing sulfydryl of the present invention is 13671-18306 dalton, and weight-average molecular weight is 17112-20303 dalton.
Description
Technical field
The invention belongs to method for preparing polyaniline field, be specifically related to a kind of polyaniline containing sulfydryl and preparation method thereof.
Background technology
Polyaniline containing sulfydryl is the very promising conducting polymer composite of one, first polyaniline is the conducting polymer of a class excellence, there is excellent environmental stability, can be used for preparing the fields such as sensor, battery, electrical condenser, antistatic material, impregnating material, have broad application prospects; Such sulfydryl polyaniline material is except the characteristic with polyaniline, sulfydryl is a kind of active group with special propertys such as self-assemblies, this material is made to carry out self-assembly, in addition, can as a kind of important lithium-sulfur cell electrode materials, secondly, " Click " can be there is and react in the mercapto groups on its main chain with unsaturated double-bond, thus, and can as a kind of important material in ultraviolet-curing paint, reduce ultraviolet light polymerization energy, strengthen the cross-linking density of film.But, polyaniline is normally by acidic medium, by peroxide agents such as ammonium persulphates, aniline is oxidized, is prepared from by radical cation polymerization, thus contain in preparation in the polyaniline process of sulfydryl, if use traditional polyaniline synthetic method, there is the sulfydryl of strong reducing property, then can oxidized dose of oxidation, then oxygenant can be oxidized the monomer of the aniline containing sulfydryl, thus, be difficult to obtain the polyaniline containing sulfydryl.Publication number is that CN1667022 reports a kind of polyaniline containing sulfydryl, its core technology is first at 50 ~ 80 DEG C of temperature, sodium lauryl sulphate is dissolved in hydrochloric acid soln, drips 2-aminothiophenol, then, again by the hydrochloric acid soln of ammonium persulphate instillation reaction system, after dropwising, continue stirring reaction 8 ~ 12h, then, in 5 ~ 8 DEG C of environment, by static for reaction solution placement 16 ~ 24h, obtain the polyaniline containing sulfydryl.The 2-aminothiophenol monomer containing sulfydryl in this patent, is exposed in the environment of ammonium persulfate oxidizing agent completely, and sulfydryl can be oxidized by oxidized dose of ammonium persulphate, thus, is difficult to obtain the real polyaniline containing sulfydryl.The people such as He Xiaoping (Wuhan University Journal, 2002,48(4): 445-448) report the poly-adjacent mercaptoaniline of solution polymerization process synthesis containing sulfydryl, find that the sulfydryl in product is partly oxidized to sulfone or sulfoxide group.
Summary of the invention
The object of the invention is in the preparation method's process in order to solve the existing polyaniline containing sulfydryl, the problem of oxidized dose of sulfydryl oxidation, and a kind of polyaniline containing sulfydryl and preparation method thereof is provided.
First the present invention provides a kind of preparation method of the polyaniline containing sulfydryl, comprises as follows:
Step one: the aniline monomer containing sulfydryl is dissolved in organic solvent, obtains the first mixing solutions, the concentration of the aniline monomer containing sulfydryl in described first mixed solution is 1 ~ 3mol/L;
Step 2: be dissolved in by oxygenant in inorganic acid aqueous solution, obtains the second mixing solutions;
Step 3: the second mixing solutions mixing that the first mixing solutions step one obtained and step 2 obtain, the aniline monomer containing sulfydryl is polymerized at water-organic solvent interface, obtains reaction product;
Step 4: the reaction product described in step 3 is obtained after washing, alcohol wash, drying the polyaniline containing sulfydryl.
Preferably, containing the one that the aniline monomer of sulfydryl is in 2-aminothiophenol or 3-aminothiophenol in described step one.
Preferably, the organic solvent of described step one is selected from one or more in methylene dichloride, chloroform and tetracol phenixin.
Preferably, the oxygenant of described step 2 is selected from one or more in ammonium persulphate, Sodium Persulfate and Potassium Persulphate.
Preferably, the mineral acid of described step 2 is selected from one or more in hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid and perchloric acid.
Preferably, in described second mixing solutions, the concentration of oxygenant is 1 ~ 3mol/L.
Preferably, in described second mixing solutions, inorganic acid concentration is 0.5 ~ 3mol/L.
Preferably, described aniline monomer containing sulfydryl and oxygenant mol ratio are 1:(1 ~ 3);
Preferably, the polymerization temperature of described step 3 is-10 ~ 10 DEG C, and the time is 12 ~ 36 hours.
The present invention also provides the preparation method of above-mentioned a kind of polyaniline containing sulfydryl the polyaniline containing sulfydryl obtained.
Beneficial effect of the present invention
First the present invention provides a kind of preparation method of the polyaniline containing sulfydryl, compare with prior art, the present invention uses " interfacial polymerization " method, radical cation polymerization is carried out at the interface formed at water-organic solvent, aniline monomer containing sulfydryl in organic solvent, only contacts at " interface " with the oxygenant be present in aqueous phase, thus reduces sulfydryl by the oxidizing chance of heavy dose, thus, sulfydryl is protected not oxidized; In addition; the present invention is the use of the large organic solvent of density ratio water; thus; the organic phase at the aniline monomer place containing sulfydryl is in lower floor, and upper strata is aqueous phase, is equivalent to the effect of " fluid-tight "; thus; lower floor containing sulfydryl aniline also can not be oxidized by the oxygen in air, so, protect sulfydryl further not oxidized.
The present invention also provides a kind of polyaniline containing sulfydryl, by the polyaniline that aforesaid method obtains, make the sulfydryl in preparation process can not dioxygen oxidation in oxidized dose and air, experimental result shows: the polyaniline number-average molecular weight containing sulfydryl of the present invention is 13671-18306 dalton, and weight-average molecular weight is 17112-20303 dalton.
Accompanying drawing explanation
Fig. 1 is the GPC graphic representation that the embodiment of the present invention 1 prepares the polyaniline containing sulfydryl;
Fig. 2 is the scanning electron microscope (SEM) photograph that the embodiment of the present invention 1 prepares the polyaniline containing sulfydryl;
Fig. 3 is the infrared spectrum containing the polyaniline of sulfydryl prepared according to embodiment 1;
Fig. 4 is the GPC graphic representation that the embodiment of the present invention 2 prepares the polyaniline containing sulfydryl;
Fig. 5 is the scanning electron microscope (SEM) photograph that the embodiment of the present invention 2 prepares the polyaniline containing sulfydryl;
Fig. 6 is the infrared spectrum containing the polyaniline of sulfydryl prepared according to embodiment 2.
Embodiment
In order to understand the present invention further, below in conjunction with embodiment, the preferred embodiments of the invention are described, but should be appreciated that these describe just as further illustrating the features and advantages of the present invention instead of the restriction to patent requirements of the present invention.
First the present invention provides a kind of preparation method of the polyaniline containing sulfydryl, comprises as follows:
Step one: the aniline monomer containing sulfydryl is dissolved in organic solvent, obtains the first mixing solutions, the concentration of the aniline monomer containing sulfydryl in described first mixed solution is 1 ~ 3mol/L;
Step 2: be dissolved in by oxygenant in inorganic acid aqueous solution, obtains the second mixing solutions;
Step 3: the second mixing solutions mixing that the first mixing solutions step one obtained and step 2 obtain, the aniline monomer containing sulfydryl is polymerized at water-organic solvent interface, obtains reaction product;
Step 4: the reaction product described in step 3 is obtained after washing, alcohol wash, drying the polyaniline containing sulfydryl.
According to the present invention, " interfacial polymerization " method of use, radical cation polymerization is carried out at the interface formed at water-organic solvent, aniline monomer containing sulfydryl in organic solvent, only contact at " interface " with the oxygenant be present in aqueous phase, thus reduce sulfydryl by the oxidizing chance of heavy dose, thus, protect sulfydryl not oxidized; In addition; the present invention is the use of the large organic solvent of density ratio water; thus; the organic phase at the aniline monomer place containing sulfydryl is in lower floor, and upper strata is aqueous phase, is equivalent to the effect of " fluid-tight "; thus; lower floor containing sulfydryl aniline also can not be oxidized by the oxygen in air, so, protect sulfydryl further not oxidized.
Aniline monomer containing sulfydryl in step one of the present invention is not particularly limited, and is preferably selected from the one in 2-aminothiophenol or 3-aminothiophenol.Described organic solvent is selected from and does not dissolve each other with water and the large organic solvent of density ratio water, the organic phase at the aniline monomer place like this containing sulfydryl is in lower floor, upper strata is aqueous phase, serve lower floor the aniline containing sulfydryl can not the effect that is oxidized by the oxygen in air, be preferably selected from one or more in methylene dichloride, chloroform and tetracol phenixin, be more preferably one or both in chloroform and tetracol phenixin.The concentration of the aniline monomer containing sulfydryl in described first mixed solution is 1 ~ 3mol/L, is preferably 1.2 ~ 2.5mol/L, is more preferably 1.5 ~ 2mol/L.
The oxygenant of step 2 of the present invention is preferably selected from one or more in ammonium persulphate, Sodium Persulfate and Potassium Persulphate; Mineral acid is preferably selected from one or more in hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid and perchloric acid, is more preferably one or more in hydrochloric acid, sulfuric acid, nitric acid and perchloric acid.In described second mixing solutions, the concentration of oxygenant is preferably 1 ~ 3mol/L, is more preferably 1.2 ~ 2.5mol/L, most preferably is 1.5 ~ 2mol/L; In described second mixing solutions, inorganic acid concentration is preferably 0.5 ~ 3mol/L, is more preferably 0.7 ~ 2.2mol/L, most preferably is 1 ~ 1.5mol/L.
Of the present invention by the first mixing solutions and the mixing of the second mixing solutions, preferably static placement at-10 ~ 10 DEG C, the aniline monomer containing sulfydryl is made to carry out radical cation polymerization at water-organic solvent interface, the preferred reaction time is 12 ~ 36 hours, obtain reaction product, the described aniline monomer aniline monomer containing sulfydryl and oxygenant mol ratio are preferably 1:(1 ~ 3), be more preferably 1:(1.3 ~ 2.5), most preferably be 1:(1.5 ~ 2).
Described in step 4 of the present invention by reaction product through washing, alcohol wash and drying, preferably by colourless to filtrate to reaction product water, methyl alcohol and deionized water wash, and then carry out drying, described drying temperature is preferably 40 ~ 50 DEG C, the vacuum-drying time is preferably 24 ~ 36h, and vacuum drying vacuum tightness is preferably 0.6MPa-0.9MPa.
With specific embodiment, technical scheme of the present invention is described below, but protection scope of the present invention being not limited by the following examples.
Embodiment 1
Be dissolved in chloroform by 2-aminothiophenol, obtain the first mixing solutions, in described first mixing solutions, aniline monomer concentration is 1mol/L;
Be dissolved in by ammonium persulphate in the hydrochloric acid of 1mol/L, obtain the second mixing solutions, in the second described mixing solutions, the concentration of ammonium persulphate is 1mol/L;
Be 2-aminothiophenol in molar ratio: ammonium persulphate=1:1, by the first mixing solutions and the mixing of the second mixing solutions, at-10 DEG C, static placement 12h, obtains reaction product;
By colourless to filtrate to reaction product water obtained above, methyl alcohol and deionized water wash; Then be 0.6MPa by product in vacuum tightness, drying temperature is vacuum-drying 24h at 40 DEG C, obtains the polyaniline containing sulfydryl.
The polyaniline containing sulfydryl prepared by the present embodiment 1 detects, Fig. 1 is the GPC graphic representation of the polyaniline of embodiment 1 containing sulfydryl, as can be seen from Figure 1, the polyaniline number-average molecular weight Mn containing sulfydryl that embodiment 1 obtains is 15662 dalton, and weight-average molecular weight Mw is 17764 dalton; Fig. 2 is the scanning electron microscope (SEM) photograph of the polyaniline of embodiment 1 containing sulfydryl, and as can be seen from Figure 2, the particle diameter of the polyaniline containing sulfydryl that embodiment 1 obtains is 1.5-2.2 μm; Fig. 3 is the infrared spectrum containing the polyaniline of sulfydryl prepared according to embodiment 1, as can be seen from Figure 3, at 2548cm
-1find sulfydryl spectrum peak (all sulfydryl spectrum peaks are all more weak), at 1384cm
-1and 1020cm
-1place does not find to compose peak, indicates and does not have sulfuryl (1384cm
-1) and sulfoxide group (1020cm
-1) formation of group.
Embodiment 2
Be dissolved in tetracol phenixin by 3-aminothiophenol, obtain the first mixing solutions, in described first mixing solutions, aniline monomer concentration is 3mol/L;
Be dissolved in by Sodium Persulfate in the hydrochloric acid of 1mol/L, obtain the second mixing solutions, in the second described mixing solutions, the concentration of Sodium Persulfate is 3mol/L;
Be 3-aminothiophenol in molar ratio: Sodium Persulfate=1:3, by the first mixing solutions and the mixing of the second mixing solutions, at 10 DEG C, static placement 36h, obtains reaction product;
By colourless to filtrate to reaction product water obtained above, methyl alcohol and deionized water wash, be then 0.9MPa by product in vacuum tightness, drying temperature is vacuum-drying 36h at 50 DEG C, obtains the polyaniline containing sulfydryl.
The polyaniline containing sulfydryl prepared by the present embodiment 2 detects, Fig. 4 is the GPC graphic representation of the polyaniline of embodiment 2 containing sulfydryl, as can be seen from Figure 3, the polyaniline number-average molecular weight Mn containing sulfydryl that embodiment 2 obtains is 14694 dalton, and weight-average molecular weight Mw is 20303 dalton; Fig. 5 is the scanning electron microscope (SEM) photograph of the polyaniline of embodiment 2 containing sulfydryl, and as can be seen from Figure 4, the particle diameter of the polyaniline containing sulfydryl that embodiment 2 obtains is 0.85-1.1 μm; Fig. 6 is the infrared spectrum containing the polyaniline of sulfydryl prepared according to embodiment 2; As can be seen from Figure 6, at 2554cm
-1find sulfydryl spectrum peak, at 1384cm-1 and 1020cm
-1place does not find to compose peak, indicates and does not have sulfuryl (1384cm
-1) and sulfoxide group (1020cm
-1) formation of group.
Embodiment 3
Be dissolved in methylene dichloride by 2-aminothiophenol, obtain the first mixing solutions, in described first mixing solutions, 2-aminothiophenol monomer concentration is 1.5mol/L;
Be dissolved in by Potassium Persulphate in the sulfuric acid of 3mol/L, obtain the second mixing solutions, in the second described mixing solutions, the concentration of Potassium Persulphate is 1.5mol/L;
Be 2-aminothiophenol in molar ratio: Potassium Persulphate=1:2, by the first mixing solutions and the mixing of the second mixing solutions, at 5 DEG C, static placement 24h, obtains reaction product;
By colourless to filtrate to reaction product water obtained above, methyl alcohol and deionized water wash, be then 0.8MPa by product in vacuum tightness, drying temperature is vacuum-drying 24h at 45 DEG C, obtains the polyaniline containing sulfydryl.
The polyaniline containing sulfydryl prepared by the present embodiment 3 detects, and result shows, the particle diameter of the polyaniline containing sulfydryl that embodiment 3 obtains is 0.7-0.9 μm, number-average molecular weight Mn is 13671 dalton, and weight-average molecular weight Mw is 17112 dalton.
Embodiment 4
Be dissolved in chloroform by 2-aminothiophenol, obtain the first mixing solutions, in described first mixing solutions, 2-aminothiophenol monomer concentration is 3mol/L;
Be dissolved in by ammonium persulphate in the nitric acid of 2mol/L, obtain the second mixing solutions, in the second described mixing solutions, the concentration of ammonium persulphate is 2mol/L;
Be 2-aminothiophenol in molar ratio: ammonium persulphate=1:3, by the first mixing solutions and the mixing of the second mixing solutions, at 0 DEG C, static placement 20h, obtains reaction product;
By colourless to filtrate to reaction product water obtained above, methyl alcohol and deionized water wash, be then 0.8MPa by product in vacuum tightness, drying temperature is vacuum-drying 22h at 48 DEG C, obtains the polyaniline containing sulfydryl.
The polyaniline containing sulfydryl prepared by the present embodiment 4 detects, and result shows, the particle diameter of the polyaniline containing sulfydryl that embodiment 4 obtains is 1.2-1.4 μm, number-average molecular weight Mn is 17189 dalton, and weight-average molecular weight Mw is 19482 dalton.
Embodiment 5
Be dissolved in chloroform by 3-aminothiophenol, obtain the first mixed solution, in described first mixed solution, 3-aminothiophenol monomer concentration is 1.5mol/L;
Be dissolved in by Potassium Persulphate in the hydrochloric acid of 1mol/L, obtain the second mixing solutions, in the second described mixing solutions, the concentration of Potassium Persulphate is 2.5mol/L;
Be 3-aminothiophenol in molar ratio: Potassium Persulphate=1:1, by the first mixing solutions and the mixing of the second mixing solutions, at-5 DEG C, static placement 20h, obtains reaction product;
By colourless to filtrate to above-mentioned reaction product water, methyl alcohol and deionized water wash, be then 0.8MPa by the product obtained in vacuum tightness, drying temperature is vacuum-drying 21h at 42 DEG C, obtains the polyaniline containing sulfydryl.
The polyaniline containing sulfydryl prepared by the present embodiment 5 detects, and result shows, the particle diameter of the polyaniline containing sulfydryl that embodiment 5 obtains is 0.5-0.8 μm, number-average molecular weight Mn is 16573 dalton, and weight-average molecular weight Mw is 18652 dalton.
Embodiment 6
Be dissolved in tetracol phenixin by 2-aminothiophenol, obtain the first mixing solutions, in described first mixing solutions, 2-aminothiophenol concentration is 3mol/L;
Be dissolved in by ammonium persulphate in the sulfuric acid of 3mol/L, obtain the second mixing solutions, in the second described mixing solutions, the concentration of ammonium persulphate is 1mol/L;
Be 2-aminothiophenol in molar ratio: ammonium persulphate=1:2.5, by the first mixing solutions and the mixing of the second mixing solutions, at 5 DEG C, static placement 26h, obtains reaction product;
By colourless to filtrate to reaction product water obtained above, methyl alcohol and deionized water wash, be then 0.6MPa by product in vacuum tightness, drying temperature is vacuum-drying 30h at 50 DEG C, obtains the polyaniline containing sulfydryl.
The polyaniline containing sulfydryl prepared by the present embodiment 6 detects, and result shows, the particle diameter of the polyaniline containing sulfydryl that embodiment 6 obtains is 1.6-2.4 μm, number-average molecular weight Mn is 18306 dalton, and weight-average molecular weight Mw is 20137 dalton.
Claims (6)
1. a preparation method for the polyaniline containing sulfydryl, is characterized in that, comprise as follows:
Step one: the aniline monomer containing sulfydryl is dissolved in organic solvent, obtains the first mixing solutions, the concentration of the aniline monomer containing sulfydryl in described first mixed solution is 1 ~ 3mol/L; Described organic solvent is selected from one or more in methylene dichloride, chloroform and tetracol phenixin;
Step 2: be dissolved in by oxygenant in inorganic acid aqueous solution, obtains the second mixing solutions; In described second mixing solutions, the concentration of oxygenant is 1 ~ 3mol/L; Inorganic acid concentration is 0.5 ~ 3mol/L;
Step 3: the second mixing solutions mixing that the first mixing solutions step one obtained and step 2 obtain, the aniline monomer containing sulfydryl is polymerized at water-organic solvent interface, obtains reaction product; The polymerization temperature of described step 3 is-10 ~ 10 DEG C, and the time is 12 ~ 36 hours;
Step 4: the reaction product described in step 3 is obtained after washing, alcohol wash, drying the polyaniline containing sulfydryl.
2. the preparation method of a kind of polyaniline containing sulfydryl according to claim 1, is characterized in that, the aniline monomer containing sulfydryl in described step one is the one in 2-aminothiophenol or 3-aminothiophenol.
3. the preparation method of a kind of polyaniline containing sulfydryl according to claim 1, is characterized in that, the oxygenant of described step 2 is selected from one or more in ammonium persulphate, Sodium Persulfate and Potassium Persulphate.
4. the preparation method of a kind of polyaniline containing sulfydryl according to claim 1, is characterized in that, the mineral acid of described step 2 is selected from one or more in hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid and perchloric acid.
5. the preparation method of a kind of polyaniline containing sulfydryl according to claim 1, is characterized in that, described aniline monomer containing sulfydryl and oxygenant mol ratio are 1:(1 ~ 3).
6. the polyaniline containing sulfydryl that obtains of the preparation method of a kind of polyaniline containing sulfydryl of claim 1-5 described in any one.
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| CN105418930B (en) * | 2014-09-23 | 2018-02-02 | 中国石油化工股份有限公司 | A kind of preparation method of water-soluble polyaniline |
| CN105482450A (en) * | 2014-10-11 | 2016-04-13 | 中国石油化工股份有限公司 | Preparation method and application of polyaniline-nano gold composite material |
| CN104497308B (en) * | 2014-12-11 | 2017-07-04 | 扬州工业职业技术学院 | A kind of preparation method of poly- adjacent mercaptoaniline nanofiber |
| CN104497307B (en) * | 2014-12-11 | 2017-07-14 | 扬州工业职业技术学院 | A kind of aniline and the preparation method of the synthesis of adjacent mercaptoaniline copolymer |
| CN109502706B (en) * | 2018-12-30 | 2021-08-10 | 太原理工大学 | Method for recovering metal ions in wastewater by using electronic control ion exchange material |
| CN112980019B (en) * | 2021-03-25 | 2023-02-14 | 西安文理学院 | Method for preparing polyaniline-nanogold film through self-assembly regulation and control on liquid-liquid two-phase interface |
| CN113600828B (en) * | 2021-08-19 | 2022-10-11 | 南京工业大学 | Protection method of silver nanoparticles |
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Effective date of registration: 20220816 Address after: No. 5218, Longhu Road, Changchun City, Jilin Province, 130000 Patentee after: Zhongke Yinghua (Changchun) Technology Co.,Ltd. Address before: 130022 5625 people's street, Chaoyang District, Changchun, Jilin. Patentee before: CHANGCHUN INSTITUTE OF APPLIED CHEMISTRY CHINESE ACADEMY OF SCIENCES |
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