CN109762332A - A kind of preparation method of the fusible conductive polyaniline of poly ion liquid doping - Google Patents
A kind of preparation method of the fusible conductive polyaniline of poly ion liquid doping Download PDFInfo
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- CN109762332A CN109762332A CN201910090912.5A CN201910090912A CN109762332A CN 109762332 A CN109762332 A CN 109762332A CN 201910090912 A CN201910090912 A CN 201910090912A CN 109762332 A CN109762332 A CN 109762332A
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- ion liquid
- poly ion
- conductive polyaniline
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Abstract
The present invention relates to a kind of fusible conductive polyanilines of poly ion liquid doping; it is characterized in that; preparation method includes: under nitrogen or inert gas shielding; the mixed liquor of poly ion liquid and aniline is added in ammonium persulfate solution; it is reacted; it is used as dopant it is not necessary that acid is added, obtains the fusible conductive polyaniline of poly ion liquid doping.The present invention introduces poly ion liquid in the polymerization process of polyaniline, so that polyaniline can dissolve in DMSO equal solvent, and is adulterated to polyaniline, has expanded the application field of aniline.
Description
Technical field
The present invention relates to a kind of fusible conductive polyanilines of poly ion liquid doping, specifically, what is involved is one kind
It can uniformly be dissolved in multi-solvents such as water, DMSO, DMF, the preparation method of 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.
It must be added to acid in the polymerization of electrically conductive polyaniline at present, such as hydrochloric acid, benzene sulfonic acid could obtain good as dopant
The polyaniline of good electric conductivity, non-acid adding class dopant does not have electric conductivity；And it has not seen at present and poly ion liquid is substituted into acid
The report of conductive soluble polyaniline is prepared as Polyaniline Doped agent.
Summary of the invention
Technical problem to be solved by the invention is to provide a kind of soluble electrically conductive polyanilines and its system of no acid doping
Preparation Method, for the present invention by the way that poly ion liquid is added in the course of the polymerization process as dopant, obtaining one kind can be in DMSO equal solvent
In there is preferable deliquescent polyaniline；Production method process of the present invention is compared with the traditional method, and is obtained in the condition of no acid doping
To conductive and soluble polyaniline, the polymerization and application field of polyaniline have been expanded.
A kind of fusible conductive polyaniline of poly ion liquid doping of the invention, which is characterized in that preparation method packet
It includes: under nitrogen or inert gas shielding, the mixed liquor of poly ion liquid and aniline being added in ammonium persulfate solution, carry out
Reaction obtains the fusible conductive polyaniline of poly ion liquid doping.
Preferably, the reaction is added without acid or acid solution as dopant.
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 fusible conductive polyaniline of above-mentioned poly ion liquid doping, 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: 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 d: the ammonium persulfate solution that step b is obtained is added in the resulting mixed liquor of step d under nitrogen protection, is being stirred
It is reacted under mixing；
Step e: by reaction product adding into acetone obtained in step d, 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 molar ratio of the aniline in the step c and the ammonium persulfate in step b is 8:1-12:1.
Preferably, the mass ratio of the aniline in the step c 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 c.
Preferably, it is reacted under the stirring in the step d, temperature is 20-30 DEG C, reaction time 1.5-
3 hours.
Preferably, the volume ratio of the acetone in the step e and reaction product obtained in step d is 3-5:1.
It is that dopant makes aniline that polymerization occur instead that the principle of the present invention, which is using ammonium persulfate as oxidant, poly ion liquid,
It answers, poly ion liquid PIL-Cl is added in the course of the polymerization process, soluble electrically conductive polyaniline is prepared.The knot of gained polyaniline
Structure composition, compound ratio, processability, resistivity can pass through nuclear magnetic resoance spectrum, fourier transform infrared spectroscopy, thermal weight loss point
The tests such as analysis, dissolubility test, transmission electron microscope, four probe method are characterized.The present invention not acid adding during the preparation process
Into ammonium persulfate solution, the soluble electrically conductive polyaniline of no acid doping is obtained, the polymerization of polyaniline has been expanded and has answered
Use field.
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 the transmitted electron of embodiment 1, fusible conductive polyaniline prepared by example 2 and comparative example 1
Microscope photo.
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
A kind of fusible conductive polyaniline of poly ion liquid doping, the matter of raw material aniline and poly ion liquid PIL-Cl
Amount is than being 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.
The fusible conductive polyaniline of above-mentioned poly ion liquid doping 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: 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 constant pressure funnel after obtaining the mixed liquor of poly ion liquid and aniline；
Step d: step is added dropwise using constant pressure funnel in the mixed liquor of step d in whipping process under nitrogen protection
In the ammonium persulfate solution that b is obtained, reaction 1.5 hours is carried out under stirring at 25 DEG C with 200rpm；
Step e: by reaction product adding into acetone (volume ratio 1:4) obtained in step d, stirring is separated by solid-liquid separation
It to precipitating, is dried in vacuo after being precipitated, obtains soluble electrically conductive polyaniline.
Step f: product will be obtained in step e and is added in DMSO, DMF, DMAC equal solvent to test its dissolubility.
Step g: 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: 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 constant pressure funnel after obtaining the mixed liquor of poly ion liquid and aniline；
Step d: the mixed liquor of step c is added dropwise in whipping process respectively using constant pressure funnel under nitrogen protection
In the ammonium persulfate solution that step b is obtained, reaction 1.5 hours is carried out under stirring at 25 DEG C with 200rpm；
Step e: by reaction product adding into acetone (volume ratio 1:4) obtained in step d, stirring is separated by solid-liquid separation
It to precipitating, is dried in vacuo after being precipitated, obtains soluble electrically conductive polyaniline.
Step f: product will be obtained in step e and is added in DMSO, DMF, DMAC equal solvent to test its dissolubility.
Step g: the electric conductivity of product is obtained in four probe method testing procedure f.
Comparative example 1
A kind of traditional chemical oxidization method is added without the polyaniline of dopant preparation, and polyion is not added in polymerization process
Liquid PIL-Cl.
Above-mentioned 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: 3.72 grams of aniline, which are added, in 80 milliliters of water makes it pour into constant pressure funnel after evenly mixing；
Step d: the mixed liquor of step c is added dropwise in whipping process respectively using constant pressure funnel under nitrogen protection
In the ammonium persulfate solution that step b is obtained, reaction 1.5 hours is carried out under stirring at 25 DEG C with 200rpm；
Step e: by reaction product adding into acetone (volume ratio 1:4) obtained in step d, stirring is separated by solid-liquid separation
It to precipitating, is dried in vacuo after being precipitated, obtains undoped polyaniline.
Step f: product will be obtained in step e 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 50nm or so.
The conductivity of Fig. 6 corresponding embodiment 1, soluble conductive polyphenyl prepared by example 2 and comparative example 1 illustrates poly- in addition
After ionic liquid is as dopant, sample non-conductive becomes conductive from original.
The one-dimensional nucleus magnetic hydrogen spectrum map of the poly ion liquid PIL-Cl of Fig. 7 corresponding embodiment 1, wherein the peak of 2.5ppm is deuterium
For the chemical shift of 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 (10)
1. a kind of fusible conductive polyaniline of poly ion liquid doping, which is characterized in that preparation method include: in nitrogen or
Under inert gas shielding, the mixed liquor of poly ion liquid and aniline is added in ammonium persulfate solution, is reacted, is gathered
The fusible conductive polyaniline of ionic liquid doping.
2. the fusible conductive polyaniline of poly ion liquid doping as described in claim 1, which is characterized in that the reaction
Acid or acid solution are added without as dopant.
3. the fusible conductive polyaniline of poly ion liquid doping as described in claim 1, which is characterized in that the aniline
Mass ratio with poly ion liquid is 1:1-4:1.
4. the fusible conductive polyaniline of poly ion liquid as described in claim 1 doping, which is characterized in that it is described gather from
The structural formula of sub- liquid are as follows:
Wherein n is 10-50.
5. the preparation method of the fusible conductive polyaniline of poly ion liquid doping of any of claims 1-4,
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: 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 d: the ammonium persulfate solution that step b is obtained is added in the resulting mixed liquor of step c under nitrogen protection, under stiring
It is reacted；
Step e: by reaction product adding into acetone obtained in step d, stirring, separation of solid and liquid is precipitated, after obtaining precipitating
Vacuum drying obtains soluble electrically conductive polyaniline.
6. the preparation method of the fusible conductive polyaniline of poly ion liquid doping as claimed in claim 5, which is characterized in that
The concentration of ammonium persulfate solution is 2-3 grams per liter in the step b.
7. the preparation method of the fusible conductive polyaniline of poly ion liquid doping as claimed in claim 5, which is characterized in that
The molar ratio of the ammonium persulfate in aniline and step b in the step c is 8:1-12:1.
8. the preparation method of the fusible conductive polyaniline of poly ion liquid doping as claimed in claim 5, which is characterized in that
The mass ratio of aniline and poly ion liquid in the step c is 1-1.4:1；The polyion of mixed liquor in the step c
The concentration of liquid is 0.01-0.05 grams per milliliter.
9. the preparation method of the fusible conductive polyaniline of poly ion liquid doping as claimed in claim 5, which is characterized in that
It is reacted under stirring in the step d, temperature is 20-30 DEG C, and the reaction time is 1.5-3 hours.
10. the preparation method of the fusible conductive polyaniline of poly ion liquid doping as claimed in claim 5, feature exist
In the volume ratio of reaction product obtained in the acetone and step e in the step e is 3-5:1.
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