CN110078914A - A kind of preparation method for the fusible conductive polyaniline that poly ion liquid is modified - Google Patents
A kind of preparation method for the fusible conductive polyaniline that poly ion liquid is modified Download PDFInfo
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- CN110078914A CN110078914A CN201910091159.1A CN201910091159A CN110078914A CN 110078914 A CN110078914 A CN 110078914A CN 201910091159 A CN201910091159 A CN 201910091159A CN 110078914 A CN110078914 A CN 110078914A
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- ion liquid
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/026—Wholly aromatic polyamines
- C08G73/0266—Polyanilines or derivatives thereof
Abstract
The present invention relates to a kind of modified fusible conductive polyanilines of poly ion liquid; it is characterized in that; preparation method includes: under nitrogen or inert gas shielding; the mixed liquor of hydrochloric acid solution and poly ion liquid and aniline is added in ammonium persulfate solution; it is reacted, obtains the modified fusible conductive polyaniline of poly ion liquid.The present invention introduces poly ion liquid in the polymerization process of polyaniline, so that polyaniline can dissolve in DMSO equal solvent, has expanded the application field of aniline.
Description
Technical field
The present invention relates to a kind of modified fusible conductive polyanilines of poly ion liquid, specifically, what is involved is one kind
It can uniformly be dissolved in multi-solvents such as the preparation method of water, DMSO, DMF, DMAC and conductive polyaniline.
Background technique
Polyaniline than more typical structural conductive high polymer, contains pi-electron cloud structure energy as a kind of in strand
Enough by doping and the secondary doping of organic and inorganic acid various in preparation process, mixed acid or other compounds, make its molecule knot
Structure, that is, degree of oxidation and protonation change, and delocalization are formed, so that becoming this common insulating polymer can
Conductive high molecular material.And because it can be obtained relatively by continuously improving doping way or compound condition
Good electric conductivity；The molecular structure of itself causes it to have a very excellent physical property, and stable structure, to environment compared with
For close friend；Synthesis material aniline easily obtains, and can be synthesized by a variety of methods, and numerous excellent properties such as easy to operate, are mesh
It is preceding to attract the conduction high polymer at most paid close attention to.
But since there are conjugatedπbonds in the strand of polyaniline, generating strong conjugation causes its rigidity and interchain
It interacts stronger, it is insoluble under normal circumstances not melt.Therefore, the synthesis better polyaniline of processability is their ability to industrialization
The main points of production and investment actual use.
Poly ion liquid is a kind of material for having both ionic liquid and polymer property, has special performance, can apply
In various fields.With science and technology, the development of research, poly ion liquid similarly constantly innovation and development, in polymer chemistry, energy
Source and materials science field have attracted huge concern.Not only due to it combines the only of the ionic liquid with macromolecular structure
Characteristic energy, more because it creates new characteristic and function.In recent years, imidazole type poly ion liquid is synthesized for dispersing agent,
For example it can stablize the nanometer materials such as the carbon nanotube in water phase and in organic phase, such as multi wall, single-walled carbon nanotube
(MWCNTs, SWCNTs) and graphene sheet layer.
Dong etc. is in " Journal of Polymer Science " the 20th the 2036-2046 pages of phase hair of volume 47 in 2010
Table " Enhancement in solubility and conductivity of polyaniline with
Lignosulfonate modified carbon nanotube " (enhances polyphenyl with lignin sulfonate modified carbon nanotube
The dissolubility and electric conductivity of amine), enhance polyaniline using calcium lignosulfonate modified carbon nano-tube, then as dopant
Dissolubility.Harlev E etc. has delivered " A the 994-997 pages of the phase of " Advanced Materials " 1996 volume 8 the 12nd
new method for the preparation of conductive polyaniline solutions:
Application to liquid crystal devices " (a method of new prepares conductive polyaniline solution: application
In liquid crystal apparatus), it is prepared for a kind of polyaniline that can be dissolved in pyruvic acid.Due to poly ion liquid as dispersing agent
The stage still in continuous development is studied, therefore the correlative study of the processability of polyaniline is increased so far by poly ion liquid
The present simultaneously has not been reported.
Summary of the invention
Technical problem to be solved by the invention is to provide a kind of electrically conductive polyaniline and preparation method thereof of solubility, this hairs
It is bright to obtain one kind by the way that poly ion liquid is added in the course of the polymerization process and have preferable deliquescent polyphenyl in DMSO equal solvent
Amine；Production method of the present invention is easy, has expanded the application field of polyaniline, has developed to bigizationner the application value of polyaniline.
A kind of modified fusible conductive polyaniline of poly ion liquid of the invention, which is characterized in that preparation method packet
It includes: under nitrogen or inert gas shielding, the mixed liquor of hydrochloric acid solution and poly ion liquid and aniline being added to persulfuric acid
It in ammonium salt solution, is reacted, obtains the modified fusible conductive polyaniline of poly ion liquid.
Preferably, the mass ratio of the aniline and poly ion liquid is 1:1-4:1.
Preferably, the poly ion liquid is PIL-Cl, structural formula are as follows:
Wherein n is 10-50.
The present invention also provides the preparation method of the modified fusible conductive polyaniline of above-mentioned poly ion liquid, features
It is, comprising:
Step a: water removal deoxygenation processing is carried out to reaction vessel；
Step b: ammonium persulfate and water being added into reaction vessel, and stirring forms ammonium persulfate solution；
Step c: concentrated hydrochloric acid dilution is instilled in water, obtains hydrochloric acid solution；
Step d: being dissolved in water poly ion liquid PIL-Cl, and aniline, which is then added, mixes it uniformly, obtain gathering from
The mixed liquor of sub- liquid and aniline；
Step e: step b is added with the resulting mixed liquor of step d in the resulting hydrochloric acid solution of step c under nitrogen protection and is obtained
The ammonium persulfate solution arrived, is reacted under stiring；
Step f: by reaction product adding into acetone obtained in step e, stirring, separation of solid and liquid is precipitated, and is sunk
It is dried in vacuo behind shallow lake, obtains soluble electrically conductive polyaniline.
Preferably, the concentration of ammonium persulfate solution is 2-3 grams per liter in the step b.
Preferably, the concentration of hydrochloric acid solution is 3-4 mol/L in the step c.
Preferably, the molar ratio of the aniline in the step d and the ammonium persulfate in step b is 8:1-12:1.
Preferably, the mass ratio of the aniline in the step d and poly ion liquid is 1-4:1.
Preferably, the concentration of the poly ion liquid of mixed liquor is 0.01-0.05. grams per milliliter in the step d.
Preferably, it is reacted under the stirring in the step e, temperature is 20-30 DEG C, reaction time 1.5-
3 hours.
Preferably, the volume ratio of the acetone in the step f and reaction product obtained in step e is 3-5:1.
It is that dopant makes aniline that polymerization reaction occur that the principle of the present invention, which is using ammonium persulfate as oxidant, hydrochloric acid, poly-
Poly ion liquid PIL-Cl is added during closing, soluble electrically conductive polyaniline is prepared.The structure composition of gained polyaniline,
Compound ratio, processability, resistivity can pass through nuclear magnetic resoance spectrum, fourier transform infrared spectroscopy, thermogravimetic analysis (TGA), dissolution
The tests such as property test, transmission electron microscope, four probe method are characterized.
Fusible conductive polyaniline prepared in accordance with the present invention, low in raw material price is convieniently synthesized, reacts controllability
It is good.It, can uniform dissolution by the addition poly ion liquid in the polymerization process of aniline to improve its processing performance
In DMSO, DMF, DMAC equal solvent, this develops the application value of polyaniline to application field, bigizationner for widening polyaniline
Etc. be of great significance.
Detailed description of the invention
Fig. 1 is the nuclear magnetic spectrogram of fusible conductive polyaniline prepared by the present invention；
Wherein: figure a, b, c respectively correspond the one-dimensional of embodiment 1, fusible conductive polyaniline prepared by example 2 and comparative example 1
Nucleus magnetic hydrogen spectrum map.
Fig. 2 is the infrared spectrogram of fusible conductive polyaniline prepared by the present invention；
Wherein: figure a, b, c respectively correspond the infrared of embodiment 1, fusible conductive polyaniline prepared by example 2 and comparative example 1
Spectrogram.
Fig. 3 is the thermogravimetric curve of fusible conductive polyaniline prepared by the present invention；
Wherein: a, b, c respectively correspond the thermal weight loss of embodiment 1, fusible conductive polyaniline prepared by example 2 and comparative example 1
Curve.
Fig. 4 is the photo that fusible conductive polyaniline prepared by the present invention dissolves in DMSO, DMF, DMAC；
Wherein: the fusible conductive polyaniline that a, b, c respectively correspond comparative example 1 and embodiment 1, prepared by example 2 DMSO,
Dissolution situation in DMF, DMAC equal solvent.
Fig. 5 is the transmission electron microscope photo of fusible conductive polyaniline prepared by the present invention；
Wherein: a, b respectively correspond embodiment 1, the transmission electron microscope of fusible conductive polyaniline prepared by example 2 shines
Piece.
Fig. 6 is the conductivity of fusible conductive polyaniline prepared by the present invention；
Wherein: a, b, c respectively correspond the conductivity of embodiment 1, fusible conductive polyaniline prepared by example 2 and comparative example 1.
Fig. 7 is the nuclear magnetic spectrogram of poly ion liquid PIL-Cl.
Specific embodiment
Present invention will be further explained below with reference to specific examples.It should be understood that these embodiments are merely to illustrate the present invention
Rather than it limits the scope of the invention.In addition, it should also be understood that, after reading the content taught by the present invention, those skilled in the art
Member can make various changes or modifications the present invention, and such equivalent forms equally fall within the application the appended claims and limited
Range.
Commercial product can be used shown in structural formula such as formula (I) in poly ion liquid PIL-Cl involved in embodiment,
Can also synthesize according to known methods, such as according to Publication No. CN105199090B, it is entitled " suitable for nonpolar solvent gather from
Sub- liquid-type acid indicator and its preparation " Chinese patent in record method synthesis.
Embodiment 1
The mass ratio of a kind of fusible conductive polyaniline, raw material aniline and poly ion liquid PIL-Cl are 1:1.
Above-mentioned poly ion liquid PIL-Cl, shown in structural formula such as formula (I), wherein n 22.According to Publication No.
CN105199090B, the China of entitled " suitable for the poly ion liquid type acid indicator of nonpolar solvent and its preparation " is specially
The method recorded in sharp embodiment 1 synthesizes, and gained precipitating is poly ion liquid PIL-Cl in step f.
Above-mentioned fusible conductive polyaniline the preparation method comprises the following steps:
Step a: water removal deoxygenation processing, the water removal deoxygenation processing are as follows: by cleaning are carried out to 250 milliliters of three-necked flasks
250 milliliters of three-necked flasks are sufficiently dried 3 hours under 90 degrees Celsius, and taking-up is cooled to room temperature, and is passed through nitrogen；
Step b: under nitrogen protection, 0.937 gram of ammonium persulfate and 40 ml deionized waters are added into three-necked flask
Stirring forms uniform ammonium persulfate solution；
Step c: it is molten to obtain 3.5mol/L hydrochloric acid after mixing for 16.4 milliliters of concentrated hydrochloric acids dilutions of instillation in 40 milliliters of water
It is poured into constant pressure funnel after liquid
Step d: 3.72 grams of poly ion liquid PIL-Cl stirrings are added in 80 milliliters of water dissolves it sufficiently, is then added
3.72 grams of aniline mix it uniformly, pour into another constant pressure funnel after obtaining the mixed liquor of poly ion liquid and aniline；
Step e: the mixed liquor of the resulting hydrochloric acid solution of step c and step d are utilized into constant pressure funnel point under nitrogen protection
It is not added dropwise in whipping process in the ammonium persulfate solution that step b is obtained, is reacted under being stirred at 25 DEG C with 200rpm
1.5 hour；
Step f: by reaction product adding into acetone (volume ratio 1:4) obtained in step e, stirring is separated by solid-liquid separation
It to precipitating, is dried in vacuo after being precipitated, obtains soluble electrically conductive polyaniline.
Step g: product will be obtained in step f and is added in DMSO, DMF, DMAC equal solvent to test its dissolubility.
Step h: the electric conductivity of product is obtained in four probe method testing procedure f.
Embodiment 2
The mass ratio of a kind of fusible conductive polyaniline, raw material aniline and poly ion liquid PIL-Cl are 3:1.
Above-mentioned poly ion liquid PIL-Cl, shown in structural formula such as formula (I), wherein n 17.According to Publication No.
CN105199090B, the China of entitled " suitable for the poly ion liquid type acid indicator of nonpolar solvent and its preparation " is specially
The method recorded in sharp embodiment 2 synthesizes, and gained precipitating is poly ion liquid PIL-Cl in step f.
Above-mentioned fusible conductive polyaniline the preparation method comprises the following steps:
Step a: water removal deoxygenation processing, the water removal deoxygenation processing are as follows: by cleaning are carried out to 250 milliliters of three-necked flasks
250 milliliters of three-necked flasks are sufficiently dried 3 hours under 90 degrees Celsius, and taking-up is cooled to room temperature, and is passed through nitrogen；
Step b: under nitrogen protection, 0.937 gram of ammonium persulfate and 40 ml deionized waters are added into three-necked flask
Stirring forms uniform ammonium persulfate solution；
Step c: 16.4 milliliters of concentrated hydrochloric acids dilutions of instillation, which are uniformly mixed, in 40 milliliters of water obtains 3.5mol/L hydrochloric acid solution
After pour into constant pressure funnel
Step d: 1.24 grams of poly ion liquid PIL-Cl stirrings are added in 80 milliliters of water dissolves it sufficiently, is then added
3.72 grams of aniline mix it uniformly, pour into another constant pressure funnel after obtaining the mixed liquor of poly ion liquid and aniline；
Step e: the mixed liquor of the resulting hydrochloric acid solution of step c and step d are utilized into constant pressure funnel point under nitrogen protection
It is not added dropwise in whipping process in the ammonium persulfate solution that step b is obtained, is reacted under being stirred at 25 DEG C with 200rpm
1.5 hour；
Step f: by reaction product adding into acetone (volume ratio 1:4) obtained in step e, stirring is separated by solid-liquid separation
It to precipitating, is dried in vacuo after being precipitated, obtains soluble electrically conductive polyaniline.
Step g: product will be obtained in step f and is added in DMSO, DMF, DMAC equal solvent to test its dissolubility.
Step h: the electric conductivity of product is obtained in four probe method testing procedure f.
Comparative example 1
Poly ion liquid PIL- is not added in polymerization process for a kind of electrically conductive polyaniline of traditional chemical oxidization method preparation
Cl。
Above-mentioned electrically conductive polyaniline the preparation method comprises the following steps:
Step a: water removal deoxygenation processing, the water removal deoxygenation processing are as follows: by cleaning are carried out to 250 milliliters of three-necked flasks
250 milliliters of three-necked flasks are sufficiently dried 3 hours under 90 degrees Celsius, and taking-up is cooled to room temperature, and is passed through nitrogen；
Step b: under nitrogen protection, 0.937 gram of ammonium persulfate and 40 ml deionized waters are added into three-necked flask
Stirring forms uniform ammonium persulfate solution；
Step c: 16.4 milliliters of concentrated hydrochloric acids dilutions of instillation, which are uniformly mixed, in 40 milliliters of water obtains 3.5mol/L hydrochloric acid solution
After pour into constant pressure funnel；
Step d: 3.72 grams of aniline, which are added, in 80 milliliters of water makes it pour into another constant pressure funnel after evenly mixing；
Step e: the mixed liquor of the resulting hydrochloric acid solution of step c and step d are utilized into constant pressure funnel point under nitrogen protection
It is not added dropwise in whipping process in the ammonium persulfate solution that step b is obtained, is reacted under being stirred at 25 DEG C with 200rpm
1.5 hour；
Step f: by reaction product adding into acetone (volume ratio 1:4) obtained in step e, stirring is separated by solid-liquid separation
It to precipitating, is dried in vacuo after being precipitated, obtained electrically conductive polyaniline.
Step g: product will be obtained in step f and is added in DMSO, DMF, DMAC equal solvent to test its dissolubility.
Embodiment result is shown in attached drawing:
Fig. 1 a, 1b, 1c respectively correspond the one-dimensional core of embodiment 1, fusible conductive polyaniline prepared by example 2 and comparative example 1
Magnetic hydrogen spectrogram spectrum, wherein the peak at 4.29-4.89ppm is the chemical shift for the secondary carbon proton being connected with ester group；5.74ppm place
Peak is the chemical shift for the tertiary carbon proton that ester group is connected；Multiplet at 7ppm-8ppm is the change of proton on phenyl ring and imidazole ring
Displacement study；Peak within the scope of 9.18-9.70ppm is the chemical shift for the secondary carbon proton being respectively connected on imidazole ring with two nitrogen.
Fig. 2 a, 2b, 2c respectively correspond the Fourier of embodiment 1, fusible conductive polyaniline prepared by example 2 and comparative example 1
Transform infrared spectroscopy, wherein 3387cm-1Place is the characteristic peak of N-H stretching vibration；1566cm-1Place is that quinone ring skeletal vibration absorbs
Peak；1472cm-1Place is phenyl ring skeletal vibration absorption peak；820cm-1Place is 1,4 substituted benzene ring C-H out-of plane bending absorption of vibrations
Peak；668cm-1Place is the bending vibration absorption peak of N-H.
Fig. 3 a, 3b, 3c respectively correspond the thermal weight loss of embodiment 1, fusible conductive polyaniline prepared by example 2 and comparative example 1
Curve.
The soluble conductive polyphenyl that Fig. 4 a, 4b, 4c respectively correspond the pure polyaniline of comparative example 1 and prepared by embodiment 1, example 2
Dissolubility of the amine in DMSO, DMF, DMAC tests photo.This it appears that poly ion liquid is deliquescent for polyaniline
Improvement result.
Fig. 5 a, 5b respectively correspond the transmission electron microscope photo of the fusible conductive polyaniline of embodiment 12 preparation, can see
The club shaped structure stacked form formed out is more close, and club shaped structure diameter is in 100nm or so.
Fig. 6 a, 6b, 6c corresponding embodiment 1, the conductivity of soluble conductive polyphenyl prepared by example 2 and comparative example 1, illustrate
After introducing poly ion liquid, sample is still conductive.
Fig. 7 is the one-dimensional nucleus magnetic hydrogen spectrum map that poly ion liquid PIL-Cl is corresponded in embodiment 1, and wherein the peak of 2.5ppm is
The chemical shift of deuterated DMSO；3.83ppm is the chemical shift of hydrogen on the carbon being connected on imidazole group with nitrogen；4.40ppm-
Multiplet within the scope of 4.75ppm is the chemical shift of hydrogen in the secondary carbon being connected with ester group；It is unimodal for ester group phase at 5.73ppm
The chemical shift of hydrogen on tertiary carbon even；Multiplet within the scope of 7ppm-8ppm is the chemical potential of hydrogen on carbon on phenyl ring and imidazole ring
It moves；Peak within the scope of 9.0ppm-9.6ppm is the chemical shift of hydrogen in the secondary carbon being respectively connected on imidazole ring with two nitrogen.
Claims (11)
1. a kind of modified fusible conductive polyaniline of poly ion liquid, which is characterized in that preparation method include: in nitrogen or
Under inert gas shielding, the mixed liquor of hydrochloric acid solution and poly ion liquid and aniline is added in ammonium persulfate solution, into
Row reaction obtains the modified fusible conductive polyaniline of poly ion liquid.
2. the modified fusible conductive polyaniline of poly ion liquid as described in claim 1, which is characterized in that the aniline
Mass ratio with poly ion liquid is 1:1-4:1.
3. the modified fusible conductive polyaniline of poly ion liquid as described in claim 1, which is characterized in that it is described gather from
The structural formula of sub- liquid are as follows:
Wherein n is 10-50.
4. the preparation method of the modified fusible conductive polyaniline of poly ion liquid of any of claims 1-3,
It is characterized in that, comprising:
Step a: water removal deoxygenation processing is carried out to reaction vessel；
Step b: ammonium persulfate and water being added into reaction vessel, and stirring forms ammonium persulfate solution；
Step c: concentrated hydrochloric acid dilution is instilled in water, obtains hydrochloric acid solution；
Step d: being dissolved in water poly ion liquid PIL-Cl, and aniline, which is then added, mixes it uniformly, obtains polyion liquid
The mixed liquor of body and aniline；
Step e: the resulting hydrochloric acid solution of step c and the resulting mixed liquor of step d are added what step b was obtained under nitrogen protection
Ammonium persulfate solution is reacted under stiring；
Step f: by reaction product adding into acetone obtained in step e, stirring, separation of solid and liquid is precipitated, after obtaining precipitating
Vacuum drying obtains soluble electrically conductive polyaniline.
5. the preparation method of the modified fusible conductive polyaniline of poly ion liquid as claimed in claim 4, which is characterized in that
The concentration of ammonium persulfate solution is 2-3 grams per liter in the step b.
6. the preparation method of the modified fusible conductive polyaniline of poly ion liquid as claimed in claim 4, which is characterized in that
The concentration of hydrochloric acid solution is 3-4 mol/L in the step c.
7. the preparation method of the modified fusible conductive polyaniline of poly ion liquid as claimed in claim 4, which is characterized in that
The molar ratio of the ammonium persulfate in aniline and step b in the step d is 8:1-12:1.
8. the preparation method of the modified fusible conductive polyaniline of poly ion liquid as claimed in claim 4, which is characterized in that
The mass ratio of aniline and poly ion liquid in the step d is 1-1.4:1.
9. the preparation method of the modified fusible conductive polyaniline of poly ion liquid as claimed in claim 4, which is characterized in that
The concentration of the poly ion liquid of mixed liquor is 0.01-0.05. grams per milliliter in the step d.
10. the preparation method of the modified fusible conductive polyaniline of poly ion liquid as claimed in claim 4, feature exist
In, reacted under the stirring in the step e, temperature be 20-30 DEG C, the reaction time be 1.5-3 hours.
11. the preparation method of the modified fusible conductive polyaniline of poly ion liquid as claimed in claim 4, feature exist
In the volume ratio of reaction product obtained in the acetone and step e in the step f is 3-5:1.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101798386A (en) * | 2010-03-17 | 2010-08-11 | 上海大学 | Method for preparing water-soluble conductive polyaniline |
| CN105199090A (en) * | 2015-08-12 | 2015-12-30 | 东华大学 | Polyion liquid acidic indicator suitable for non-polar solvent and preparation method thereof |
| CN105418930A (en) * | 2014-09-23 | 2016-03-23 | 中国石油化工股份有限公司 | Preparation method of water-soluble polyaniline |
| CN108530621A (en) * | 2018-03-19 | 2018-09-14 | 厦门理工学院 | A kind of conducting polymer and preparation method thereof of solubility |
-
2019
- 2019-01-30 CN CN201910091159.1A patent/CN110078914A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101798386A (en) * | 2010-03-17 | 2010-08-11 | 上海大学 | Method for preparing water-soluble conductive polyaniline |
| CN105418930A (en) * | 2014-09-23 | 2016-03-23 | 中国石油化工股份有限公司 | Preparation method of water-soluble polyaniline |
| CN105199090A (en) * | 2015-08-12 | 2015-12-30 | 东华大学 | Polyion liquid acidic indicator suitable for non-polar solvent and preparation method thereof |
| CN108530621A (en) * | 2018-03-19 | 2018-09-14 | 厦门理工学院 | A kind of conducting polymer and preparation method thereof of solubility |
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