CN101538365B - Method for preparing organic/inorganic acid composite doped conductive polyaniline - Google Patents
Method for preparing organic/inorganic acid composite doped conductive polyaniline Download PDFInfo
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- CN101538365B CN101538365B CN2009100942079A CN200910094207A CN101538365B CN 101538365 B CN101538365 B CN 101538365B CN 2009100942079 A CN2009100942079 A CN 2009100942079A CN 200910094207 A CN200910094207 A CN 200910094207A CN 101538365 B CN101538365 B CN 101538365B
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- 229920000767 polyaniline Polymers 0.000 title claims abstract description 44
- 239000002131 composite material Substances 0.000 title claims abstract description 27
- 150000007524 organic acids Chemical class 0.000 title claims abstract description 15
- 150000007522 mineralic acids Chemical class 0.000 title claims abstract description 13
- 238000000034 method Methods 0.000 title abstract description 12
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 44
- 239000002019 doping agent Substances 0.000 claims abstract description 37
- 239000000178 monomer Substances 0.000 claims abstract description 17
- 239000000843 powder Substances 0.000 claims abstract description 12
- 238000003756 stirring Methods 0.000 claims abstract description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 19
- YCPXWRQRBFJBPZ-UHFFFAOYSA-N 5-sulfosalicylic acid Chemical group OC(=O)C1=CC(S(O)(=O)=O)=CC=C1O YCPXWRQRBFJBPZ-UHFFFAOYSA-N 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 10
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 9
- 239000004160 Ammonium persulphate Substances 0.000 claims description 5
- 235000019395 ammonium persulphate Nutrition 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000012065 filter cake Substances 0.000 claims description 3
- 238000009775 high-speed stirring Methods 0.000 claims description 3
- 238000000967 suction filtration Methods 0.000 claims description 3
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims description 2
- MMCPOSDMTGQNKG-UHFFFAOYSA-N anilinium chloride Chemical compound Cl.NC1=CC=CC=C1 MMCPOSDMTGQNKG-UHFFFAOYSA-N 0.000 claims description 2
- 239000012153 distilled water Substances 0.000 claims description 2
- 238000005303 weighing Methods 0.000 claims description 2
- 230000003068 static effect Effects 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 20
- 239000000463 material Substances 0.000 abstract description 11
- 239000010405 anode material Substances 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 abstract description 3
- 238000004377 microelectronic Methods 0.000 abstract description 2
- 239000007787 solid Substances 0.000 abstract description 2
- 238000005538 encapsulation Methods 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 238000004806 packaging method and process Methods 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 6
- 239000011707 mineral Substances 0.000 description 6
- 235000010755 mineral Nutrition 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000002322 conducting polymer Substances 0.000 description 3
- 229920001940 conductive polymer Polymers 0.000 description 3
- 239000004020 conductor Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
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- 238000009792 diffusion process Methods 0.000 description 2
- 239000012776 electronic material Substances 0.000 description 2
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- 229920000126 latex Polymers 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- 0 *c(c(*)c1*)c(*)c(*)c1N Chemical compound *c(c(*)c1*)c(*)c(*)c1N 0.000 description 1
- ASKIRBGBLRTUSL-UHFFFAOYSA-N 1,2-di(nonyl)naphthalene;sulfuric acid Chemical compound OS(O)(=O)=O.C1=CC=CC2=C(CCCCCCCCC)C(CCCCCCCCC)=CC=C21 ASKIRBGBLRTUSL-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- JDJYXGZPTAHXGA-UHFFFAOYSA-N OCOCc(cc(cc1)S(O)(=O)=O)c1O Chemical compound OCOCc(cc(cc1)S(O)(=O)=O)c1O JDJYXGZPTAHXGA-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003990 capacitor Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000009878 intermolecular interaction Effects 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 230000005693 optoelectronics Effects 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
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- 229920001197 polyacetylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000004984 smart glass Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- DAJSVUQLFFJUSX-UHFFFAOYSA-M sodium;dodecane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCCCS([O-])(=O)=O DAJSVUQLFFJUSX-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
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- 230000009466 transformation Effects 0.000 description 1
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- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Abstract
The invention relates to a method for preparing organic/inorganic acid composite doped conductive polyaniline. The method is characterized by comprising the following steps: adding aniline monomer, doping agent, oxidant and acid solution in terms of a certain proportion into a reaction container, stirring the mixture at high speed till forming suspension. During the reaction, the reaction conditions are strictly controlled; after the reaction is finished, the reactants are washed, filtered, dried and grinded to form solid powder. By adjusting the doping proportion of the organic/inorganic composite acid, the category of the composite acid, the mixture rate of the doping agent and the aniline monomer, and the like, the electric conductivity of the polyaniline can be effectively controlled. The polyaniline powder synthesized by the method can be applied to the fields of insoluble anode materials, anti-electrostatic materials, electromagnetic shielding materials, sensitive components, intelligent windows, secondary batteries, stealthy materials, anticorrosive materials, microelectronics packaging and electronic component encapsulation materials, and the like.
Description
Technical field
The present invention relates to technical field of electronic materials, specifically a kind of preparation method of organic/inorganic acid composite doped conductive polyaniline.
Background technology
In recent years, along with development of electronic technology, developed the electronic material of many novelties.Particularly, obtained the technological innovation of attracting attention relating to high-performance organic materials field.Even only aspect electro-conductive material, developed by some mineral acids or macromole function protonic acid as doping agent the conducting polymer materials that the mode of mix electron conjugated polymkeric substance such as polyacetylene, Polythiophene, polypyrrole and polyaniline etc. makes.And polyaniline is the conducting polymer that has practicability to wish most.It has excellent chemical property and chemical stability, unique doping and dedoping mechanism, and raw materials for production are easy to get, simple synthetic method, at insoluble anode material, the energy, opto-electronic device, information, transmitter, molecular wire and molecular device, and extensive, tempting application prospect is all arranged on electromagnetic shielding, anti-corrosion of metal and the stealthy technique, caused people's extensive concern.
Polyaniline is because conjugated backbone structure and the indissoluble infusibility has limited its practical application at some special occasions improves the workability of polyaniline, and particularly solubility just seems extremely important.The selection of doping agent and doping way is to influence polyaniline lead and deliquescent important factor, therefore is one of hot fields of polyaniline research.
Chinese patent CNI583830A, a kind of method of utilizing the direct synthesized polyaniline solution of aniline monomer is disclosed, use Witco 1298 Soft Acid, dinonyl naphthalene sulfuric acid, dodecyl sulphate, dodecyl sodium sulfonate, stearic acid, oleic acid or their sodium salt, sylvite, described latex comprises water, doped polyaniline and polymer and disperses auxiliary agent, has obtained a kind of polyaniline latex with highly stable water.
What above patent was all used in actual mechanical process is that single doping agent mixes to aniline monomer, make doping agent and use such as organic acids such as Witco 1298 Soft Acids, all to use the preparation of emulsion splitter p-poly-phenyl amine to make subsequent disposal, make subsequent technique become complicated.
The specific conductivity of polyaniline in eigenstate is very low, is electrical insulating property.After with protonic acid p-poly-phenyl amino-group doping, specific conductivity can reach 5～10S/cm, can realize the transformation from the isolator to the conductor, is the effective way of giving polyaniline conductivity.The fusing point and the boiling point of organic macromolecule sulfonic acid are higher, are better than mineral acid aspect environmental stability, and it had both contained non-polar group, polar functionalities again, and not only specific conductivity is higher to make doped polyaniline, and the solvability in solvent improves.
Chinese patent CNI325382A disclose a kind of with Phenylsulfonic acid and derivative as dopant acid, prepare the method for electrically conductive polyaniline, its dopant acid molecule is described as having following constitutional features:
The doping agent that can be used as electron conjugated polymkeric substance, and, have high conductivity and good thermotolerance with the conducting polymer materials that this compound doped conjugated polymers is made, can be used as the electro-conductive material of the negative electrode in the solid electrolytic capacitor.But this dopant acid complicated process of preparation, and cost is higher.
Chinese patent CN1733820 discloses a kind of composite acids doped preparation electrically conductive polyaniline, and described doping agent is made up of main doping agent and auxiliary dopant, and the main doping agent of this doping agent is selected sulphosalicylic acid for use, and its molecule has following constitutional features:
Sulphosalicylic acid is as the main doping agent of conjugated polymers, but should the acid cost higher, it be unstable to mix.
Summary of the invention
The preparation method who the purpose of this invention is to provide the organic/inorganic acid composite doped conductive polyaniline that a kind of cost is low, technology is simple, quality product is high.
Technical scheme of the present invention is: among the preparation method of organic/inorganic acid composite doped conductive polyaniline, use a kind of novel doping agent, this doping agent is made up of main doping agent and auxiliary dopant, and main doping agent is selected sulfuric acid (H for use
2SO
4), its molecular structural formula is as follows:
Molar content in composite mixed dose is 70～100%; Auxiliary dopant is a sulphosalicylic acid, and the constitutional features of its molecule is:
Molar content in composite mixed dose is 0～30%.
The preparation process of organic/inorganic acid composite doped conductive polyaniline is as follows:
1) takes by weighing a certain amount of doping agent and dissolve in the distilled water, pour reaction unit into and be stirred to dissolving fully;
2) slowly drip aniline monomer, the mol ratio of doping agent and aniline monomer is 1～4, high-speed stirring;
3) stir 30min after, become transparent or semitransparently and slightly yellow up to whole system, indicate that aniline has been dissolved into aniline salt this moment;
4) drip the ammonium persulfate solution that has prepared, wherein the mol ratio of ammonium persulphate and aniline monomer is 0.5～2, and the dropping time is 60min;
5) under 15～35 ℃, reacted 6 hours, solution need not breakdown of emulsion, and directly suction filtration places the polyaniline filter cake in the baking oven, in 50～60 ℃ of bakings 24 hours, grind into powder.
Above-mentioned steps 2) relate to a kind of aniline monomer in and have following molecular formula:
In the formula, R
1, R
2, R
3, R
4, R
5Be respectively-H ,-CH
3,-NO
2,-F ,-Cl ,-OCH
3,-C
2H
5,-Br and/or-I.
The size of polyaniline specific conductivity and doping agent, oxygenant and acidic solution all have relation, but wherein doping agent plays decisive influence for the specific conductivity of polyaniline.The doping agent that the doping of polyaniline is adopted usually has mineral acid and organic acid two big classes.Mineral acid is easy to diffusion because its molecular dimension is less, and the effect of therefore mixing is better, but the stability decreases of the polyaniline after it mixes has restricted its further application in practice.With respect to the small molecules mineral acid, therefore organic protonic acid can make its environmental stability improve because molecular dimension is big, and rate of diffusion is slow, promptly is better than mineral acid aspect environmental stability, and it had both contained non-polar group, contained polar group again.So by the proportioning that changes organic/inorganic acid composite doped dose of kind, organic/inorganic acid composite doped dose of component concentration, doping agent and aniline monomer is the specific conductivity size of may command polyaniline, this is one of characteristics of the present invention.
Polyaniline powder provided by the invention can be applicable to aspects such as insoluble anode material, antistatic material, electromagnetic shielding material, sensitive components, smart window, secondary cell, stealth material and anticorrosion material, microelectronics packing and electronic original part component package material.In composite acids doped system, sulphosalicylic acid and sulfuric acid are collaborative to enter the polyaniline skeleton, and polyaniline molecule is existed with the extended chain conformation, reduces its intermolecular interaction force, help the delocalization of electric charge and the enhancing of charge movement, thereby make sample have higher specific conductivity and doping rate.
Embodiment
Below in conjunction with embodiment the present invention is further described.
Embodiment 1
Get the 4.7ml aniline monomer and join in the 100ml 1mol/L sulphuric acid soln, be stirred to dissolving fully; Solution is poured in the 250mL three-necked bottle, behind the high-speed stirring 30min, dripped the aqueous solution 100ml that contains the 12.8g ammonium persulphate again, the dropping time is 30min.Under 20 ℃, reacted 6 hours, suction filtration places the polyaniline filter cake in the baking oven, and baking is 24 hours in about 50 ℃, grind into powder.Recording this polyaniline powder specific conductivity with four electrode conductance rate instrument is 3.1S/cm.
Embodiment 2
Keep composite mixed dose with the aniline mol ratio constant, changing composite mixed dose of component is sulfuric acid and sulphosalicylic acid codoped, and wherein the mole proportioning is 33: 7, and promptly sulfuric acid molar content in the compound doping agent of organic/inorganic is 82.5%, the molar content of sulphosalicylic acid is 17.5%.Other condition is identical with embodiment 1.Recording this polyaniline powder specific conductivity is 13.4S/cm.
Embodiment 3
Keep composite mixed dose with the aniline mol ratio constant, changing composite mixed dose of component is sulfuric acid and sulphosalicylic acid codoped, wherein the mole proportioning is 7: 3, and promptly sulfuric acid molar content in the compound doping agent of organic/inorganic is 70%, and the molar content of sulphosalicylic acid is 30%.The mol ratio of ammonium persulphate and aniline monomer is 0.5, and temperature of reaction is 15 ℃, and other condition is identical with embodiment 1.Record this polyaniline powder specific conductivity and be respectively 11.4S/cm.
Embodiment 4
Keep composite mixed dose with the aniline mol ratio constant, changing composite mixed dose of component is sulfuric acid and sulphosalicylic acid codoped, wherein the mole proportioning is 19: 1, and promptly sulfuric acid molar content in the compound doping agent of organic/inorganic is 95%, and the molar content of sulphosalicylic acid is 5%.The mol ratio of ammonium persulphate and aniline monomer is 2, and temperature of reaction is 35 ℃, and other condition is identical with embodiment 1.Record this polyaniline powder specific conductivity and be respectively 8.1S/cm.
Embodiment 5
The mol ratio that changes doping agent and aniline monomer is 1, and other condition is identical with embodiment 3.Record this polyaniline powder specific conductivity and be respectively 9.4S/cm.
Embodiment 6
The mol ratio that changes doping agent and aniline monomer is 4, and other condition is identical with embodiment 3.Record this polyaniline powder specific conductivity and be respectively 10.1S/cm.
Specific conductivity in the foregoing description is to adopt the four point probe method to record.
The commodity polyaniline of selling in the market by the production of Changchun applied chemistry institute is tested its specific conductivity with identical method, and compare, the results are shown in Table 1 with the specific conductivity that adopts the prepared sample of the inventive method
Table 1
By above embodiment and table 1 as can be seen, adopt that the preparation method of organic/inorganic acid composite doped conductive polyaniline described in the invention not only is easy to produce, subsequent disposal is simple, and and in the market commodity polyaniline compare, aspect electroconductibility, increase significantly.
Claims (1)
1. the preparation method of an organic/inorganic acid composite doped conductive polyaniline is characterized in that step is as follows:
1) takes by weighing a certain amount of organic/inorganic acid composite doped dose and be dissolved in the distilled water, pour reaction unit into and be stirred to dissolving fully; Organic/inorganic acid composite doped dose is divided into main doping agent and auxiliary, main doping agent is a sulfuric acid, molar content is more than or equal to 70% to less than 100% in composite mixed dose, and auxiliary dopant is a sulphosalicylic acid, and molar content is to smaller or equal to 30% greater than 0 in composite mixed dose;
2) slowly drip aniline monomer, the mol ratio of doping agent and aniline monomer is 1～4, high-speed stirring;
3) stir 30min after, become transparently and slightly yellow up to whole solution system, indicate that aniline has been dissolved into aniline salt this moment;
4) drip the ammonium persulfate solution that has prepared, wherein the mol ratio of ammonium persulphate and aniline monomer is 0.5～2, and the dropping time is 60min;
5) under 15～35 ℃, reacted after 6 hours static 24 hours, washing, suction filtration places the polyaniline filter cake in the baking oven, in 50～60 ℃ of bakings 24 hours, grind into powder.
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