CN101585907A - The preparation method of conductive polymer poly (3,4 dioxoethyl) thiophene tiny balloon - Google Patents
The preparation method of conductive polymer poly (3,4 dioxoethyl) thiophene tiny balloon Download PDFInfo
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- CN101585907A CN101585907A CNA2008101120787A CN200810112078A CN101585907A CN 101585907 A CN101585907 A CN 101585907A CN A2008101120787 A CNA2008101120787 A CN A2008101120787A CN 200810112078 A CN200810112078 A CN 200810112078A CN 101585907 A CN101585907 A CN 101585907A
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Abstract
The invention belongs to the conducting polymer materials field, relate to the preparation method of polythiophene class conductive polymers tiny balloon, particularly the emulsion single stage method prepares the preparation method of conductive polymer poly (3,4 dioxoethyl) thiophene tiny balloon.By conditions such as water-soluble polymer, 3,4 dioxoethyl thiophene (EDOT) monomers, oxygenant, doping agent in the regulation and control emulsion, can obtain the tiny balloon of conductive polymer poly (3,4 dioxoethyl) thiophene (PEDOT).Method of the present invention is fit to the preparation of other polythiophene class tiny balloon equally.Simple, the easy row of method of the present invention, the resulting emulsion that comprises poly-(3,4 dioxoethyl) thiophene (PEDOT) tiny balloon can have the advantage that is easy to be coated with processing directly as coating fluid.
Description
Technical field
The invention belongs to the conducting polymer materials field, relate to the preparation method of polythiophene class conductive polymers tiny balloon, particularly the emulsion single stage method prepares the method for conductive polymer poly (3,4 dioxoethyl) thiophene tiny balloon.
Background technology
Tiny balloon owing to have light weight, easily disperse and can supported catalyst or the advantages such as slowly-releasing of carrying out medicine have good application prospects to enjoy people's attention in coating, the fields such as ripple, catalysis and biological agent of inhaling.
In the conductive polymer microspheres research field, people use template to coat the shell that forms conductive polymers on polystyrene (PS) ball surface usually, will obtain hollow conductive polymer microspheres after the dissolving of polystyrene (PS) template again.(Chemistry ofMaterials, 2003,15 (1) 233～239) such as Armes etc. (Advanced Materials, 2000,12:671～674) and Cairns use method of modifying to coat polypyrrole on polystyrene (PS) ball surface respectively.(Material Chemistry of Physics such as YANG, 2005,92 (1): 164～171) utilize dispersion copolymerization method to prepare polystyrene (PS) template, polyaniline and polypyrrole have been coated respectively at template surface then, after the dissolving of polystyrene (PS) template, obtain polyaniline and polypyrrole hollow microsphere.Khan and Ames etc. (Chem.Commun.2004,19,2154) coat poly-(3,4 dioxoethyl) thiophene (PEDOT) respectively on polystyrene (PS) and silicon grain.These preparation methods are complicated, and the process of template need be arranged.(Adv.Funct.Mater., 2003,13,815～820) such as Meixiang Wan propose the method that self-assembly method prepares polyaniline open tube and hollow ball, and are simple and convenient than template.(macromol.RapidCommun.2006 such as Mumtaz, 27,1446～1453) reported in the methanol system and be connected on 3 with polyoxyethylene (PEO), on 4 dioxoethyl thiophene (EDOT) monomers, dispersion polymerization is gathered (3,4 dioxoethyl) thiophene (PEDOT) hollow ball, discloses a kind of with nozzle blowing air in reaction solution in the Chinese patent 20071005755, utilize the method for bubble for poly-(3,4 dioxoethyl) thiophene (PEDOT) hollow ball of template preparation.
Summary of the invention
The objective of the invention is to propose the method that a kind of emulsion single stage method prepares conductive polymer poly (3,4 dioxoethyl) thiophene (PEDOT) tiny balloon.
Conductive polymer poly of the present invention (3,4 dioxoethyl) thiophene (PEDOT) tiny balloon obtains by the letex polymerization single stage method, and this preparation method may further comprise the steps:
A) be solvent with water and acetonitrile mixed solution, the preparation mass concentration is 1%～10% water-soluble polymer solution; Wherein: the volume ratio of water and acetonitrile is 1: 2～20: 1, is preferably 2: 1～5: 1;
B) oxygenant is joined in the water-soluble polymer solution of step a) preparation, stirring and dissolving, the volumetric molar concentration of oxygenant in water-soluble polymer solution is 1.0 * 10
-3～1.0mol/L obtains the mixed solution of water-soluble polymer solution and oxygenant;
C) under agitation condition, 3,4 dioxoethyl thiophene (EDOT) are joined in the mixed solution that step b) obtains, wherein: the molar weight of 3,4 dioxoethyl thiophene (EDOT) of adding is 0.2～10 times of the oxygenant molar weight that adds in the step b); At room temperature continue stirring reaction 12 hours～72 hours, and obtained containing the black emulsion of conductive polymer poly (3,4 dioxoethyl) thiophene tiny balloon; Or
Under agitation condition, sour doping agent is joined in the mixed solution that step b) obtains, the concentration of sour doping agent in mixed solution is 0.1～0.5mol/L; Add 3,4 dioxoethyl thiophene (EDOT) then, wherein: the molar weight of 3,4 dioxoethyl thiophene (EDOT) of adding is 4～20 times of the oxygenant molar weight that adds in the step b); At room temperature continue stirring reaction 12 hours～72 hours, and obtained containing the black emulsion of conductive polymer poly (3,4 dioxoethyl) thiophene tiny balloon;
D) the black emulsion that contains conductive polymer poly (3,4 dioxoethyl) thiophene (PEDOT) tiny balloon that step c) is obtained obtains the Dark grey blocks of solid 40～80 ℃ of oven dry down; This solid is ground, cross 120 mesh sieves, obtain dark gray powder; To soak 0.5～2 hour in this dark gray powder immersion water and the ethanol mixed solvent; Suction filtration then, and with an amount of water and alcohol mixed solvent drip washing, colourless substantially up to leacheate, the filter cake that obtains has obtained graphite glossy black powder at 40～90 ℃ of following vacuum dryings; Above-mentioned black powder promptly is conductive polymer poly (3,4 dioxoethyl) thiophene (PEDOT) tiny balloon, its particle diameter between 100nm～10 μ m, 200nm～2 μ m preferably.Its specific conductivity is 1 * 10
-4Between～the 10S/cm.
Described water-soluble polymer comprises polyvinyl alcohol (PVA), polyvinylpyrrolidone (PVP) or polyoxyethylene glycol (PEG) etc.
Described oxygenant is ammonium persulphate or Potassium Persulphate etc.
Described sour doping agent can be beta-naphthalenesulfonic-acid, tosic acid or camphorsulfonic acid etc.
Described water and alcoholic acid volume ratio are 1: 1.
Simple, the easy row of method of the present invention by conditions such as water-soluble polymer, 3,4 dioxoethyl thiophene (EDOT) monomers, oxygenant, doping agent in the regulation and control emulsion, can obtain the tiny balloon of conductive polymer poly (3,4 dioxoethyl) thiophene (PEDOT).And the emulsion of poly-(3,4 dioxoethyl) thiophene (PEDOT) tiny balloon of bag of the present invention's preparation can have the advantage that is easy to be coated with processing directly as coating fluid.Method of the present invention is fit to the preparation of other polythiophene class tiny balloon equally.
Description of drawings
Fig. 1. the stereoscan photograph of the conductive polymer poly of the embodiment of the invention 1 (3,4 dioxoethyl) thiophene tiny balloon.
Fig. 2. the stereoscan photograph of the conductive polymer poly of the embodiment of the invention 4 (3,4 dioxoethyl) thiophene tiny balloon.
Fig. 3. the transmission electron microscope photo of the conductive polymer poly of the embodiment of the invention 4 (3,4 dioxoethyl) thiophene tiny balloon.
Embodiment
Embodiment 1.
A) be that 4: 1 water and acetonitrile mixed solution is solvent with volume ratio, the preparation mass concentration is 3% polyvinylpyrrolidone (PVP) solution.
B) the ammonium persulphate oxygenant is joined in the polyvinylpyrrolidonesolution solution of step a) preparation, stirring and dissolving, the volumetric molar concentration of ammonium persulphate oxygenant in polyvinylpyrrolidonesolution solution is 0.05mol/L, obtains the mixed solution of polyvinylpyrrolidone and ammonium persulphate;
C) under agitation condition, the beta-naphthalenesulfonic-acid doping agent is joined in the mixed solution that step b) obtains, the concentration of beta-naphthalenesulfonic-acid doping agent in mixed solution is 0.3mol/L; Add 3,4 dioxoethyl thiophene (EDOT) then, wherein: the molar weight of 3,4 dioxoethyl thiophene of adding is 4.5 times of the ammonium persulphate molar weight that adds in the step b); At room temperature continue stirring reaction 24 hours, and obtained containing the black emulsion of conductive polymer poly (3,4 dioxoethyl) thiophene tiny balloon;
D) the black emulsion that contains conductive polymer poly (3,4 dioxoethyl) thiophene (PEDOT) tiny balloon that step c) is obtained obtains the Dark grey blocks of solid 40 ℃ of oven dry down; This solid is ground, cross 120 mesh sieves, obtain dark gray powder; To soak 1 hour in this dark gray powder immersion water and the ethanol mixed solvent (volume ratio is 1: 1); Suction filtration then, and with an amount of water and alcohol mixed solvent (volume ratio is 1: 1) drip washing, colourless substantially up to leacheate, the filter cake that obtains has obtained graphite glossy black powder at 90 ℃ of following vacuum dryings; Be conductive polymer poly (3,4 dioxoethyl) thiophene (PEDOT) tiny balloon, electromicroscopic photograph as shown in Figure 1.About 100～the 300nm of tiny balloon diameter, the about 50nm of thickest.Specific conductivity 2.1S/cm.
Embodiment 2.
A) be that 8: 1 water and acetonitrile mixed solution is solvent with volume ratio, the preparation mass concentration is 10% polyvinyl alcohol (PVA) solution.
B) the Potassium Persulphate oxygenant is joined in the polyvinyl alcohol solution of step a) preparation, stirring and dissolving, the volumetric molar concentration of Potassium Persulphate oxygenant in polyvinyl alcohol solution is 0.9mol/L, obtains the mixed solution of polyvinyl alcohol and Potassium Persulphate;
C) under agitation condition, the camphorsulfonic acid doping agent is joined in the mixed solution that step b) obtains, the concentration of camphorsulfonic acid doping agent in mixed solution is 0.1mol/L; Add 3,4 dioxoethyl thiophene (EDOT) then, wherein: the molar weight of 3,4 dioxoethyl thiophene of adding is 8 times of the ammonium persulphate molar weight that adds in the step b); At room temperature continue stirring reaction 72 hours, and obtained containing the black emulsion of conductive polymer poly (3,4 dioxoethyl) thiophene tiny balloon;
D) the black emulsion that contains conductive polymer poly (3,4 dioxoethyl) thiophene (PEDOT) tiny balloon that step c) is obtained obtains the Dark grey blocks of solid 70 ℃ of oven dry down; This solid is ground, cross 120 mesh sieves, obtain dark gray powder; To soak 1 hour in this dark gray powder immersion water and the ethanol mixed solvent (volume ratio is 1: 1); Suction filtration then, and with an amount of water and alcohol mixed solvent (volume ratio is 1: 1) drip washing, colourless substantially up to leacheate, the filter cake that obtains has obtained graphite glossy black powder at 80 ℃ of following vacuum dryings; Be conductive polymer poly (3,4 dioxoethyl) thiophene (PEDOT) tiny balloon, the about 400nm of tiny balloon diameter～1.1 μ m, the about 70nm of thickest.Specific conductivity 6.1 * 10
-2S/cm.
Embodiment 3.
A) be that 2: 1 water and acetonitrile mixed solution is solvent with volume ratio, the preparation mass concentration is 1% polyvinylpyrrolidone (PVP) solution.
B) the ammonium persulphate oxygenant is joined in the polyvinylpyrrolidonesolution solution of step a) preparation, stirring and dissolving, the volumetric molar concentration of ammonium persulphate oxygenant in polyvinylpyrrolidonesolution solution is 5 * 10
-3Mol/L obtains the mixed solution of polyvinylpyrrolidone and ammonium persulphate;
C) under agitation condition, the tosic acid doping agent is joined in the mixed solution that step b) obtains, the concentration of beta-naphthalenesulfonic-acid doping agent in mixed solution is 0.5mol/L; Add 3,4 dioxoethyl thiophene (EDOT) then, wherein: the molar weight of 3,4 dioxoethyl thiophene of adding is 18 times of the ammonium persulphate molar weight that adds in the step b); At room temperature continue stirring reaction 48 hours, and obtained containing the black emulsion of conductive polymer poly (3,4 dioxoethyl) thiophene tiny balloon;
D) the black emulsion that contains conductive polymer poly (3,4 dioxoethyl) thiophene (PEDOT) tiny balloon that step c) is obtained obtains the Dark grey blocks of solid 80 ℃ of oven dry down; This solid is ground, cross 120 mesh sieves, obtain dark gray powder; To soak 1.5 hours in this dark gray powder immersion water and the ethanol mixed solvent (volume ratio is 1: 1); Suction filtration then, and with an amount of water and alcohol mixed solvent (volume ratio is 1: 1) drip washing, colourless substantially up to leacheate, the filter cake that obtains has obtained graphite glossy black powder at 50 ℃ of following vacuum dryings; Be conductive polymer poly (3,4 dioxoethyl) thiophene (PEDOT) tiny balloon, electromicroscopic photograph as shown in Figure 1.About 100～the 600nm of tiny balloon diameter, the about 50nm of thickest.Specific conductivity 3.7 * 10
-1S/cm.
Embodiment 4.
A) be that 10: 1 water and acetonitrile mixed solution is solvent with volume ratio, the preparation mass concentration is 5% polyvinyl alcohol (PVA) solution.
B) the Potassium Persulphate oxygenant is joined in the polyvinyl alcohol solution of step a) preparation, stirring and dissolving, the volumetric molar concentration of Potassium Persulphate oxygenant in polyvinyl alcohol solution is 0.05mol/L, obtains the mixed solution of polyvinyl alcohol and Potassium Persulphate;
C) under agitation condition, 3,4 dioxoethyl thiophene (EDOT) are joined in the mixed solution that step b) obtains, wherein: the molar weight of 3,4 dioxoethyl thiophene (EDOT) of adding is 0.5 times of the oxygenant molar weight that adds in the step b); At room temperature continue stirring reaction 72 hours, and obtained containing the black emulsion of conductive polymer poly (3,4 dioxoethyl) thiophene tiny balloon;
D) the black emulsion that contains conductive polymer poly (3,4 dioxoethyl) thiophene (PEDOT) tiny balloon that step c) is obtained obtains the Dark grey blocks of solid 80 ℃ of oven dry down; This solid is ground, cross 120 mesh sieves, obtain dark gray powder; To soak 2 hours in this dark gray powder immersion water and the ethanol mixed solvent (volume ratio is 1: 1); Suction filtration then, and with an amount of water and alcohol mixed solvent (volume ratio is 1: 1) drip washing, colourless substantially up to leacheate, the filter cake that obtains has obtained graphite glossy black powder at 70 ℃ of following vacuum dryings; Be conductive polymer poly (3,4 dioxoethyl) thiophene (PEDOT) tiny balloon, electromicroscopic photograph is shown in Fig. 2 and 3.About 200～the 800nm of tiny balloon diameter, the about 10～30nm of wall thickness.Specific conductivity is 1.9 * 10
-1S/cm.
Embodiment 5.
A) be that 5: 1 water and acetonitrile mixed solution is solvent with volume ratio, the preparation mass concentration is 1% polyvinylpyrrolidone (PVP) solution.
B) the ammonium persulphate oxygenant is joined in the polyvinylpyrrolidonesolution solution of step a) preparation, stirring and dissolving, the volumetric molar concentration of ammonium persulphate oxygenant in polyvinylpyrrolidonesolution solution is 0.5mol/L, obtains the mixed solution of polyvinylpyrrolidone and ammonium persulphate;
C) under agitation condition, 3,4 dioxoethyl thiophene (EDOT) are joined in the mixed solution that step b) obtains, wherein: the molar weight of 3,4 dioxoethyl thiophene (EDOT) of adding is 8 times of the oxygenant molar weight that adds in the step b); At room temperature continue stirring reaction 12 hours, and obtained containing the black emulsion of conductive polymer poly (3,4 dioxoethyl) thiophene tiny balloon;
D) the black emulsion that contains conductive polymer poly (3,4 dioxoethyl) thiophene (PEDOT) tiny balloon that step c) is obtained obtains the Dark grey blocks of solid 70 ℃ of oven dry down; This solid is ground, cross 120 mesh sieves, obtain dark gray powder; To soak 1 hour in this dark gray powder immersion water and the ethanol mixed solvent (volume ratio is 1: 1); Suction filtration then, and with an amount of water and alcohol mixed solvent (volume ratio is 1: 1) drip washing, colourless substantially up to leacheate, the filter cake that obtains has obtained graphite glossy black powder at 50 ℃ of following vacuum dryings; Be conductive polymer poly (3,4 dioxoethyl) thiophene (PEDOT) tiny balloon, about 400～1.2 μ m of tiny balloon diameter, specific conductivity is 2.6 * 10
-3S/cm.
Claims (10)
1. the preparation method of a conductive polymer poly (3,4 dioxoethyl) thiophene tiny balloon is to be prepared by the letex polymerization single stage method, it is characterized in that this preparation method may further comprise the steps:
A) be solvent with water and acetonitrile mixed solution, the preparation mass concentration is 1%～10% water-soluble polymer solution; Wherein: the volume ratio of water and acetonitrile is 1: 2～20: 1;
B) oxygenant is joined in the water-soluble polymer solution of step a) preparation, stirring and dissolving, the volumetric molar concentration of oxygenant in water-soluble polymer solution is 1.0 * 10
-3～1.0mol/L obtains the mixed solution of water-soluble polymer solution and oxygenant;
C) under agitation condition, 3,4 dioxoethyl thiophene are joined in the mixed solution that step b) obtains, wherein: the molar weight of 3,4 dioxoethyl thiophene of adding is 0.2～10 times of the oxygenant molar weight that adds in the step b); At room temperature continue stirring reaction, obtain containing the emulsion of conductive polymer poly (3,4 dioxoethyl) thiophene tiny balloon; Or
Under agitation condition, sour doping agent is joined in the mixed solution that step b) obtains, the concentration of sour doping agent in mixed solution is 0.1～0.5mol/L; Add 3,4 dioxoethyl thiophene then, wherein: the molar weight of 3,4 dioxoethyl thiophene of adding is 4～20 times of the oxygenant molar weight that adds in the step b); At room temperature continue stirring reaction, obtain containing the emulsion of conductive polymer poly (3,4 dioxoethyl) thiophene tiny balloon;
D) emulsion that contains conductive polymer poly (3,4 dioxoethyl) thiophene tiny balloon that step c) is obtained obtains conductive polymer poly (3,4 dioxoethyl) thiophene tiny balloon 40～80 ℃ of oven dry down through aftertreatment.
2. method according to claim 1 is characterized in that: described aftertreatment is to grind drying the solid that obtains down at 40～80 ℃, crosses 120 mesh sieves, obtains powder; To soak in this powder immersion water and the ethanol mixed solvent; Suction filtration, and water then and alcohol mixed solvent drip washing, the filter cake that obtains obtain conductive polymer poly (3,4 dioxoethyl) thiophene tiny balloon at 40～90 ℃ of following vacuum dryings.
3. method according to claim 1 and 2 is characterized in that: the particle diameter of described conductive polymer poly (3,4 dioxoethyl) thiophene tiny balloon is between 100nm～10 μ m.
4. method according to claim 3 is characterized in that: the particle diameter of described conductive polymer poly (3,4 dioxoethyl) thiophene tiny balloon is between 200nm～2 μ m.
5. according to claim 1,2 or 4 described methods, it is characterized in that: the specific conductivity of described conductive polymer poly (3,4 dioxoethyl) thiophene tiny balloon is 1 * 10
-4Between～the 10S/cm.
6. method according to claim 3 is characterized in that: the specific conductivity of described conductive polymer poly (3,4 dioxoethyl) thiophene tiny balloon is 1 * 10
-4Between～the 10S/cm.
7. method according to claim 1 is characterized in that: described water-soluble polymer is polyvinyl alcohol, polyvinylpyrrolidone or polyoxyethylene glycol.
8. method according to claim 1 is characterized in that: described oxygenant is ammonium persulphate or Potassium Persulphate.
9. method according to claim 1 is characterized in that: described sour doping agent is beta-naphthalenesulfonic-acid, tosic acid or camphorsulfonic acid.
10. method according to claim 2 is characterized in that: described water and alcoholic acid volume ratio are 1: 1.
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| CN117229536B (en) * | 2023-09-22 | 2024-03-15 | 江苏恒辉安防股份有限公司 | Preparation method of polythiophene modified acrylic pulp conductive composite latex coating glove |
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