CN109810250A - A kind of preparation method of soluble conductive polypyrrole - Google Patents
A kind of preparation method of soluble conductive polypyrrole Download PDFInfo
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Abstract
The present invention relates to a kind of soluble conductive polypyrroles and preparation method thereof; the preparation method of the soluble conductive polypyrrole includes: that liquor ferri trichloridi is added in the mixed solution of pyrrole monomer and poly ion liquid under high speed shear effect under nitrogen protection; it is reacted, obtains soluble conductive polypyrrole.The present invention introduces the effect of poly ion liquid and high speed shear in the polymerization process of polypyrrole, so that polypyrrole can dissolve in DMSO equal solvent, has expanded the application field of polypyrrole.
Description
Technical field
The present invention relates to a kind of electric polypyrroles of solubility, specifically, what is involved is one kind uniformly to dissolve
In multi-solvents in such as water, DMSO, DMF and DMAC, and the preparation method of conductive polypyrrole.
Background technique
Polypyrrole than more typical structural conductive high polymer, contains pi-electron cloud structure energy as a kind of in strand
It is enough so that its molecular structure i.e. degree of oxidation and protonation is changed by chemical doping during the preparation process, formed from
Domain, so that this common insulating polymer be made to become the high molecular material for capableing of conduction.And because it can be by continuous
Doping way or compound condition are improved, relatively good electric conductivity can be obtained；The molecular structure of itself causes it with non-
The physical property of Chang Youyi, and stable structure, it is more friendly to environment；Synthesis material easily obtains, and can pass through a variety of methods
Synthesis, numerous excellent properties such as easy to operate have attracted a large amount of concern.
But since there are conjugatedπbonds in the strand of polypyrrole, generating strong conjugation causes its rigidity and interchain
It interacts stronger, it is insoluble under normal circumstances not melt.Therefore, the synthesis better polypyrrole 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.
Wang etc. is delivered in " Synthetic Metals " the 717-721 pages of the 17-18 phase of volume 158 in 2008
“Synthesis and characterization of a new polypyrrole based on N-vinyl
Pyrrole " (synthesis and characterization of a kind of novel polypyrrole based on N- vinyl pyrrole), introduces on the N atom of pyrrole ring
Vinyl, has synthesized N- vinyl pyrrole monomer, then with FeCl3Cause monomer polymerization for oxidant, which can be dissolved in
Common organic solvents.Li et al. is in " European Polymer Journal " the 6th the 2532-2539 pages of phase hair of volume 43 in 2007
Table " Electrochemical synthesis and characterization of poly (pyrrole-co-
Tetrahydrofuran) conducting copolymer " (pyrroles-tetraphydro furan conductive copolymer electrochemistry formated and table
Sign), using electrochemical method one-step synthesis pyrroles-tetra oxygen furyl copolymer, experiments have shown that the presence of polytetrahydrofuran chain
Hydrophily is provided for copolymer.Due to poly ion liquid as dispersing agent research still in continuous development stage, because
The correlative study of this processability for increasing polypyrrole by poly ion liquid so far and has not been reported.
Summary of the invention
Technical problem to be solved by the invention is to provide a kind of electric polypyrrole 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 poly- pyrrole in DMSO equal solvent
It coughs up；Production method of the present invention is easy, has expanded the application field of polypyrrole, has developed to bigizationner the application value of polypyrrole.
In order to achieve the above object, the present invention provides a kind of preparation method of soluble conductive polypyrrole, feature exists
In, comprising the following steps:
Step a: water removal deoxygenation processing is carried out to reaction vessel；
Step b: pyrrole monomer and water being added into reaction vessel, and stirring forms chromium solution；
Step c: being added Iron(III) chloride hexahydrate in water, and stirring obtains liquor ferri trichloridi；
Step d: concentrated hydrochloric acid dilution is instilled in water, obtains hydrochloric acid solution；
Step e: make poly ion liquid be dissolved in water then be added step b reaction vessel in, obtain pyrrole monomer and
The mixed solution of poly ion liquid；
Step f: step b is added under high speed shear effect in the resulting liquor ferri trichloridi of step c under nitrogen protection
In the mixed solution of resulting pyrrole monomer and poly ion liquid, reacted；
Step g: 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 electric polypyrrole.
Preferably, high speed shear effect is realized that the revolving speed of high-speed shearing machine is 10000rpm- by high-speed shearing machine
40000rpm。
Preferably, the poly ion liquid is PIL-Cl, structural formula are as follows:
Wherein, n 10-50.
Preferably, the concentration of chromium solution is 5-10 grams per liter in the step b.
Preferably, the concentration of liquor ferri trichloridi is 1-5 mol/L in the step c.
Preferably, the concentration of hydrochloric acid solution is 2-4 mol/L in the step d.
Preferably, the poly ion liquid in the step e and the mass ratio of pyrroles in step b are 1-1.4:1.
Preferably, the concentration of poly ion liquid is 20-150 grams per liter in the mixed solution in the step f.
Preferably, the high speed shear effect in the step g is realized that the revolving speed of high-speed shearing machine is by high-speed shearing machine
10000rpm-40000rpm, reaction temperature are 0-10 DEG C, and the reaction time is 3-5 hours.
Preferably, the volume ratio of the acetone in the step g and reaction product obtained in step e is 3-5:1.
Preferably, the adding manner in the step f is to be added dropwise using constant pressure funnel.
The principle of the present invention is to make pyrroles that polymerization reaction occur by oxidant of ferric trichloride, is added in the course of the polymerization process poly-
Simultaneously soluble electric polypyrrole is prepared in ionic liquid PIL-Cl under the action of high speed shear.The structure of gained polypyrrole
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.
Soluble conductive polypyrrole 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 pyrroles to improve its processing performance
In DMSO, DMF, DMAC equal solvent, this develops the application value of polypyrrole to application field, bigizationner for widening polypyrrole
Etc. be of great significance.
The present invention cooperates high speed shear, obtains solubility more by introducing poly ion liquid on traditional polymerization
Good, the smaller polymer of partial size, obtains better electric conductivity.
Detailed description of the invention
Fig. 1 is the nuclear magnetic spectrogram of soluble conductive polypyrrole prepared by the present invention；
Wherein: figure a, b, c respectively correspond the one-dimensional of embodiment 1, soluble conductive polypyrrole prepared by example 2 and comparative example 1
Nucleus magnetic hydrogen spectrum map.
Fig. 2 is the infrared spectrogram of soluble conductive polypyrrole prepared by the present invention；
Wherein: figure a, b, c respectively correspond the infrared of embodiment 1, soluble conductive polypyrrole prepared by example 2 and comparative example 1
Spectrogram.
Fig. 3 is the thermogravimetric curve of soluble conductive polypyrrole prepared by the present invention；
Wherein: a, b, c respectively correspond the thermal weight loss of embodiment 1, soluble conductive polypyrrole prepared by example 2 and comparative example 1
Curve.
Fig. 4 is the photo that soluble conductive polypyrrole prepared by the present invention dissolves in DMSO, DMF, DMAC；
Wherein: the soluble conductive polypyrrole 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 soluble conductive polypyrrole prepared by the present invention；
Wherein: a, b, c respectively correspond the transmission electricity of embodiment 1, soluble conductive polypyrrole prepared by example 2 and comparative example 1
Sub- microscope photo.
Fig. 6 is the conductivity of soluble conductive polypyrrole prepared by the present invention；
Wherein: a, b, c respectively correspond the conductivity of embodiment 1, soluble conductive polypyrrole prepared by example 2 and comparative example 1.
Fig. 7 is the nuclear magnetic spectrogram of poly ion liquid PIL-Cl.
Fig. 8 is embodiment 1, example 2, the saturated concentration of polypyrrole prepared by comparative example 1 in each solvent.
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 soluble conductive polypyrrole, the mass ratio of pyrroles and poly ion liquid PIL-Cl are 1:2 in raw material.
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 soluble conductive polypyrrole 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, 1.01 grams of pyrroles and the stirring of 130 ml deionized waters are added into three-necked flask
Form uniform chromium solution；
Step c: be added in 10 milliliters of water 9.46 grams of Iron(III) chloride hexahydrates be uniformly mixed to obtain ferric trichloride it is molten
It is poured into constant pressure funnel after liquid；
Step d: it is instilled in 20 milliliters of water after the dilution of 6.4 milliliters of concentrated hydrochloric acids is uniformly mixed and obtains 2.7mol/L hydrochloric acid solution
It pours into constant pressure funnel；
Step e: 2.02 grams of poly ion liquid PIL-Cl stirrings are added in 50 milliliters of water dissolves it sufficiently, is then added
In the reaction vessel of step b, the mixed solution of pyrrole monomer and poly ion liquid is obtained；
Step f: under nitrogen protection by the resulting liquor ferri trichloridi of step c and the resulting hydrochloric acid solution of step d in height
The high speed shear effect of fast cutter is lower to be added dropwise the resulting pyrrole monomer of step b and poly ion liquid using constant pressure funnel
In mixed solution, the revolving speed of high-speed shearing machine is 12000rpm, and 4 hours of reaction are carried out under 5 DEG C of stirrings, and speed of agitator is
200rpm；
Step g: by reaction product adding into acetone (volume ratio 1:4) obtained in step f, stirring is separated by solid-liquid separation
It to precipitating, is dried in vacuo after being precipitated, obtains soluble electric polypyrrole.
Step h: product will be obtained in step g and is added in DMSO, DMF, DMAC to test its dissolubility.
Step i: the electric conductivity of product is obtained in four probe method testing procedure g.
Embodiment 2
A kind of soluble conductive polypyrrole, the mass ratio of pyrroles and poly ion liquid PIL-Cl are 1:4 in raw material.
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 soluble conductive polypyrrole 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, 1.01 grams of pyrroles and the stirring of 130 ml deionized waters are added into three-necked flask
Form uniform chromium solution；
Step c: be added in 10 milliliters of water 9.46 grams of Iron(III) chloride hexahydrates be uniformly mixed to obtain ferric trichloride it is molten
It is poured into constant pressure funnel after liquid；
Step d: it is instilled in 20 milliliters of water after the dilution of 6.4 milliliters of concentrated hydrochloric acids is uniformly mixed and obtains 2.7mol/L hydrochloric acid solution
It pours into constant pressure funnel；
Step e: 4.04 grams of poly ion liquid PIL-Cl stirrings are added in 50 milliliters of water dissolves it sufficiently, is then added
In the reaction vessel of step b, the mixed solution of pyrrole monomer and poly ion liquid is obtained；
Step f: under nitrogen protection by the resulting liquor ferri trichloridi of step c and the resulting hydrochloric acid solution of step d in height
The high speed shear effect of fast cutter is lower to be added dropwise the resulting pyrrole monomer of step b and poly ion liquid using constant pressure funnel
In mixed solution, the revolving speed of high-speed shearing machine is 20000rpm, and 4 hours of reaction are carried out under 5 DEG C of stirrings, and speed of agitator is
200rpm；
Step g: 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 electric polypyrrole.
Step h: product will be obtained in step g and is added in DMSO, DMF, DMAC to test its dissolubility.
Step i: the electric conductivity of product is obtained in four probe method testing procedure g.
Comparative example 1
A kind of modified soluble conductive polypyrrole of poly ion liquid, pyrroles and poly ion liquid PIL-Cl in raw material
Mass ratio is 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 modified soluble conductive polypyrrole of above-mentioned poly ion liquid 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, 1.01 grams of pyrroles and the stirring of 130 ml deionized waters are added into three-necked flask
Form uniform chromium solution；
Step c: be added in 10 milliliters of water 9.46 grams of Iron(III) chloride hexahydrates be uniformly mixed to obtain ferric trichloride it is molten
Liquid pours into constant pressure funnel；
Step d: it is instilled in 20 milliliters of water after the dilution of 6.4 milliliters of concentrated hydrochloric acids is uniformly mixed and obtains 2.7mol/L hydrochloric acid solution
It pours into constant pressure funnel；
Step e: 1.01 grams of poly ion liquid PIL-Cl stirrings are added in 50 milliliters of water dissolves it sufficiently, is then added
In the reaction vessel of step b, the mixed solution of pyrrole monomer and poly ion liquid is obtained；
Step f: the hydrochloric acid solution under nitrogen protection obtaining the resulting liquor ferri trichloridi of step c and step d utilizes
Constant pressure funnel is added dropwise in the mixed solution of the resulting pyrrole monomer of step b and poly ion liquid in whipping process, 5
It DEG C is stirred down with 200rpm and to carry out 4 hours of reaction；
Step g: by reaction product adding into acetone (volume ratio 1:4) obtained in step f, stirring is separated by solid-liquid separation
It to precipitating, is dried in vacuo after being precipitated, obtains the modified soluble conductive polypyrrole of poly ion liquid.
Step h: product will be obtained in step g and is added in DMSO, DMF, DMAC to test its dissolubility.
Step i: the electric conductivity of product is obtained in four probe method testing procedure g.
Embodiment result is shown in attached drawing:
Fig. 1 a, 1b, 1c respectively correspond the one-dimensional core of embodiment 1, soluble conductive polypyrrole 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 solubility of embodiment 1, soluble conductive polypyrrole prepared by example 2 and comparative example 1
The fourier transform infrared spectroscopy of electric polypyrrole, wherein 3423cm-1Place is the characteristic peak of N-H stretching vibration；1554cm-1Place
For pyrroles's ring skeleton C=C stretching vibration absworption peak；1313cm-1Place is antisymmetric stretching vibration absorption peak；1174cm-1Place is pair
Claim stretching vibration absworption peak；1043cm-1Place is C-N vibration absorption peak.
Fig. 3 a, 3b, 3c respectively correspond the thermal weight loss of embodiment 1, soluble conductive polypyrrole prepared by example 2 and comparative example 1
Curve.
The soluble conductive polypyrrole that a, b, c respectively correspond comparative example 1 and embodiment 1 in Fig. 4, prepared by example 2 DMSO,
Dissolubility in DMF, DMAC tests photo.It can be seen that high speed shear acts on improvement result deliquescent for polypyrrole.
Fig. 5 a, 5b, 5c respectively correspond the soluble conductive polypyrrole of embodiment 12 preparation and the transmission electron microscope of comparative example 1
Photo, it can be seen that the chondritic stacked form of formation is more loose, and chondritic diameter is in 30nm or so, and comparative example 1
Spherical particle diameter in 50nm or so, illustrate that high speed shear can obtain the particle of smaller diameter in the course of the polymerization process.
Fig. 6 a, 6b, 6c corresponding embodiment 1, the conductivity of soluble conductive polypyrrole prepared by example 2 and comparative example 1, explanation
Under the action of high speed shear, sample has better electric conductivity.
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.
The saturation in different solvents of soluble conductive polypyrrole prepared by Fig. 8 corresponding embodiment 1, example 2 and comparative example 1
Concentration value.It can be seen from the figure that the saturated concentration value of the Soluble Polypyrrole prepared by embodiment 1, example 2 is higher than comparative example 1
Saturated concentration value.
Claims (10)
1. a kind of preparation method of soluble conductive polypyrrole, which comprises the following steps:
Step a: water removal deoxygenation processing is carried out to reaction vessel；
Step b: pyrrole monomer and water being added into reaction vessel, and stirring forms chromium solution；
Step c: being added Iron(III) chloride hexahydrate in water, and stirring obtains liquor ferri trichloridi；
Step d: concentrated hydrochloric acid dilution is instilled in water, obtains hydrochloric acid solution；
Step e: make poly ion liquid be dissolved in water then be added step b reaction vessel in, obtain pyrrole monomer and gather from
The mixed solution of sub- liquid；
Step f: step b is added in the resulting liquor ferri trichloridi of step c and the resulting hydrochloric acid solution of step d under nitrogen protection
In the mixed solution of resulting pyrrole monomer and poly ion liquid, reacted；
Step g: by reaction product adding into acetone obtained in step f, stirring, separation of solid and liquid is precipitated, after obtaining precipitating
Vacuum drying obtains the modified soluble conductive polypyrrole of poly ion liquid.
2. the preparation method of soluble conductive polypyrrole as described in claim 1, which is characterized in that the high speed shear is made
It is realized with by high-speed shearing machine, the revolving speed of high-speed shearing machine is 10000rpm-40000rpm.
3. the preparation method of soluble conductive polypyrrole as described in claim 1, which is characterized in that the poly ion liquid
For PIL-Cl, structural formula are as follows:
Wherein, n 10-50.
4. the preparation method of soluble conductive polypyrrole as described in claim 1, which is characterized in that pyrrole in the step b
The concentration for coughing up solution is 5-10 grams per liter.
5. the preparation method of soluble conductive polypyrrole as described in claim 1, which is characterized in that three in the step c
The concentration of ferric chloride solution is 1-5 mol/L；The concentration of hydrochloric acid solution is 2-4 mol/L in the step c.
6. the preparation method of soluble conductive polypyrrole as described in claim 1, which is characterized in that in the step d
Poly ion liquid and the mass ratio of pyrroles in step b are 1-1.4:1.
7. the preparation method of soluble conductive polypyrrole as described in claim 1, which is characterized in that in the step d
The concentration of poly ion liquid is 20-150 grams per liter in mixed solution.
8. the preparation method of soluble conductive polypyrrole as described in claim 1, which is characterized in that in the step e
High speed shear effect is realized that the revolving speed of high-speed shearing machine is 10000rpm-40000rpm, reaction temperature 0- by high-speed shearing machine
10 DEG C, the reaction time is 3-5 hours.
9. the preparation method of soluble conductive polypyrrole as described in claim 1, which is characterized in that in the step f
The volume ratio of acetone and reaction product obtained in step e is 3-5:1.
10. the preparation method of soluble conductive polypyrrole as described in claim 1, which is characterized in that in the step e
Adding manner is to be added dropwise using constant pressure funnel.
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Application publication date: 20190528 |