WO2002024989A1 - Fabrication method of conductive polyaniline spinning solution - Google Patents

Fabrication method of conductive polyaniline spinning solution Download PDF

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Publication number
WO2002024989A1
WO2002024989A1 PCT/KR2001/001568 KR0101568W WO0224989A1 WO 2002024989 A1 WO2002024989 A1 WO 2002024989A1 KR 0101568 W KR0101568 W KR 0101568W WO 0224989 A1 WO0224989 A1 WO 0224989A1
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Prior art keywords
polyaniline
spinning solution
salt
solution
sulfuric acid
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PCT/KR2001/001568
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French (fr)
Inventor
Sung Joo Lee
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Smart Materials Technology Inc.
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Priority to AU2001292375A priority Critical patent/AU2001292375A1/en
Publication of WO2002024989A1 publication Critical patent/WO2002024989A1/en

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    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
    • D01F6/76—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from other polycondensation products
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F2/00—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof
    • D01F2/06—Monocomponent artificial filaments or the like of cellulose or cellulose derivatives; Manufacture thereof from viscose
    • D01F2/08—Composition of the spinning solution or the bath
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/88—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polycondensation products as major constituent with other polymers or low-molecular-weight compounds
    • D01F6/90—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polycondensation products as major constituent with other polymers or low-molecular-weight compounds of polyamides
    • D01F6/905—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polycondensation products as major constituent with other polymers or low-molecular-weight compounds of polyamides of aromatic polyamides

Definitions

  • This invention relates to fabricate conductive polyaniline and polyaniline-blend spinning solutions.
  • This invention refers to the fabrication method of conductive polymer polyaniline and polyaniline blend spinning solution, the fabrication method of spinning solution using polyaniline salts in detail.
  • Polyaniline is all the base form of the polymer which has the complicated process of preparation as follows. Polyaniline salt was prepared when oxidant was added to aniline monomer in aqueous acid solution and filtered. This salt was treated in aqueous acid solution and filtered again. Polyaniline salt was converted to base form Emeraldine Base(EB) after neutralizing with weak base and vacuum drying. Then, EB was used for fabrication of spinning solution. It was disclosed that polyaniline or polyaniline blend fibers are processed from solutions in concentrated sulfuric acid in Polymer Co mun. 31.
  • Polyaniline and poly(p-phenylene terephthalamide) (aramid) blend fiber was processed from solution in concentrated sulfuric acid(98 wt %). This blend fiber had the improved mechanical properties whereas kept the conductivity of pure polyaniline. In this method, dissolve polyaniline base in concentrated sulfuric acid.
  • MacDiarmid et. al. disclosed the processing of high molecular weight polymer solution in concentrated sulfuric acid or l-methyl-2-pyrrolidinone(NMP) was drawn into the amorphous pure polyaniline fiber(U. S. PAT. No. 5,177,187). The same method is applied as previously described.
  • Polyaniline and ⁇ oly(p- ⁇ henylene terephthalamide) blend fiber Jen et al. in U. S. Pat. No. 5,069, 820(melt spinning), Smith et al. in U. S. Pat. No. 5, 196, 144(solution spinning from 96% sulfuric acid solutions) and Elsenbaumer in U. S. Pat. No.
  • this invention relates to the fabrication method of polyaniline, polyaniline-blend spinning solution using the product of polyaniline salt in the first step of polyaniline preparation.
  • the present inventor has found a fabrication method of polyaniline spinning solution with dissolving directly polyaniline saltOiydrochloride, sulfate) in concentrated sulfuric acid.
  • the present inventor has also found a method for polyaniline blend spinning solution by mixing polyaniline spinning solution with blend solution in concentrated sulfuric acid.
  • the existing procedure is made up of complicated multi-steps.
  • spinning solution is easily prepared applying EB salt directly in concentrated aqueous acid solution instead of first three steps in the existing process.
  • hydrochloric acid and sulfuric acid are used for the preparation of polyaniline.
  • the first products of the process is polyaniline-hydrochloride salt or polyaniline-H2S0 salt.
  • polyaniline-hydrochloride salt when it reacts with concentrated sulfuric acid, polyaniline-hydrochloride salt changes into polyaniline-H2S0 salt. Additionally, hydrogenchloride gas is generated, whish is easily evaporated on the way of preparation of spinning solution. For polyaniline-H2S0 4 salt, it is easily dissolved in concentrated sulfuric acid and spinning solution is also easily fabricated.
  • Figure 1 illustrates the comparison of the process between the existing and the present invention fabrication method of polyaniline and polyaniline blend spinning solution.
  • Figure 1 illustrates the comparison of the process of the fabrication method of polyaniline, polyaniline blend spinning solution.
  • composition of matter and process of this invention are further illustrated in the following examples.
  • Example 1 Preparation of polyaniline spinning solution from polyaniline hydrochlride salt. 40ml(0.22 mol) of purified aniline was added in IM aqueous hydrochloric acid solution and kept at 0 ° C . 23g of oxidant (NH 2S2O8 was added and kept at 0 ° C in 400ml of IM aqueous hydrocholric acid solution. Then oxidant solution was gradually added into aniline solution for 2 minutes, when two solutions reached at temperature equilibrium. After stirring for 90 minutes at 0 ° C , polyaniline-hydrochloride salt was filtered and dried.
  • oxidant NH 2S2O8
  • polyaniline fiber After dissolving 15g of polyaniline hydrochloride salt in 85g concentrated sulfuric acid(above 98% w/w), hydrogen chloride gas was evaporated in air-free bath. Then, polyaniline fiber was obtained by spinning under nitrogen gas pressure in coagulating bath including distilled water and air dried for 2 days. The fiber prepared exhibited a conductivity of 10 S/cm.
  • Example 3 Preparation of polyaniline blend spinning solution from polyaniline hydrochloride salt.
  • solution B Dissolve 15g of Aramid pulp in 85g of concentrated sulfuric acid(above 98% w/w).
  • solution B Mix solution A and solution B at the ratio of 9:1, 8:2, 7:3, 6:4, 5:5, 4:6, 3:7, 2:8 and 1 :9, respectively.
  • Polyaniline aramid fiber was obtained by spinning under nitrogen gas pressure in coagulating bath including distilled water. The composite fibers were dried in the air for 2 days and had the conductivity as illustrated in Table 1. The conductivity studies indicated that there wasn't any variation among fibers up to 5: 5 ratio, there was a sudden drop above that ratio, according to the increase of aramid.
  • solution B Mix solution A and solution B at the ratio of 9: 1, 8:2, 7:3, 6:4, 5: 5, 4:6, 3:7, 2:8 and 1:9, respectively.
  • Polyaniline aramid fiber was obtained by spinning under nitrogen gas pressure in coagulating bath including distilled water. The composite fibers were dried in the air for 2 days and had the conductivity as illustrated in Table 1. The conductivity studies indicated that there wasn't any variation among fibers up to 5:5 ratio, there was a sudden drop above that ratio, according to the increase of aramid.
  • the present invention relates to the fabrication method of polyaniline, polyaniline blend spinning solution using the product of polyaniline salt. That is, this invention refers to the fabrication method of conductive polymer fibers which is characterized by the simplicity of process and cut down expenses using the first polyaniline salt in the first step of polyaniline preparation. Besides, fibers that have various conductivity can be prepared by the same process.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Artificial Filaments (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

This invention refers to the fabrication method of conductive polymer polyaniline and polynaniline blend spinning solution, the fabrication method of spinning solution using polyaniline salts in detail. This method is characterized by the dissolution of polyaniline salt instead of EB(emeraldine base), in concentrated sulfuric acid for fabrication of polyaniline spinning solution. There are two ways for preparation of spinning solution. There are two ways for preparation of spinning solution, the dissolution of pure polyaniline salt, the dissolution of polyaniline salt and aramidor nylon in concentrated sulfuric acid(polyaniline blend).

Description

FABRICATION METHOD OF CONDUCTIVE POLYANILINE
SPINNING SOLUTION
Technical Field
This invention relates to fabricate conductive polyaniline and polyaniline-blend spinning solutions.
Background Art
This invention refers to the fabrication method of conductive polymer polyaniline and polyaniline blend spinning solution, the fabrication method of spinning solution using polyaniline salts in detail. Generally, the polymer referred to as "Polyaniline" is all the base form of the polymer which has the complicated process of preparation as follows. Polyaniline salt was prepared when oxidant was added to aniline monomer in aqueous acid solution and filtered. This salt was treated in aqueous acid solution and filtered again. Polyaniline salt was converted to base form Emeraldine Base(EB) after neutralizing with weak base and vacuum drying. Then, EB was used for fabrication of spinning solution. It was disclosed that polyaniline or polyaniline blend fibers are processed from solutions in concentrated sulfuric acid in Polymer Co mun. 31. 275(1990). Polyaniline and poly(p-phenylene terephthalamide) (aramid) blend fiber was processed from solution in concentrated sulfuric acid(98 wt %). This blend fiber had the improved mechanical properties whereas kept the conductivity of pure polyaniline. In this method, dissolve polyaniline base in concentrated sulfuric acid.
For example, MacDiarmid et. al. disclosed the processing of high molecular weight polymer solution in concentrated sulfuric acid or l-methyl-2-pyrrolidinone(NMP) was drawn into the amorphous pure polyaniline fiber(U. S. PAT. No. 5,177,187). The same method is applied as previously described. For polyaniline and ρoly(p-ρhenylene terephthalamide) blend fiber, Jen et al. in U. S. Pat. No. 5,069, 820(melt spinning), Smith et al. in U. S. Pat. No. 5, 196, 144(solution spinning from 96% sulfuric acid solutions) and Elsenbaumer in U. S. Pat. No. 5, 160,457(spinning from solutions and doping) also disclosed the same way of fabrication using the polyaniline base form of EB. As earlier explained, the fabrication of the above method has the disadvantages of complicate procedures and high cost of production where the use of base form of polyaniline, EB. Disclosure of Invention
In order to solve the above problems, this invention relates to the fabrication method of polyaniline, polyaniline-blend spinning solution using the product of polyaniline salt in the first step of polyaniline preparation.
The present inventor has found a fabrication method of polyaniline spinning solution with dissolving directly polyaniline saltOiydrochloride, sulfate) in concentrated sulfuric acid. The present inventor has also found a method for polyaniline blend spinning solution by mixing polyaniline spinning solution with blend solution in concentrated sulfuric acid.
Following detailed explanations are based on the attached figure. As described in Figure 1, the existing procedure is made up of complicated multi-steps. However, in the present invention, spinning solution is easily prepared applying EB salt directly in concentrated aqueous acid solution instead of first three steps in the existing process. Generally, hydrochloric acid and sulfuric acid are used for the preparation of polyaniline. The first products of the process is polyaniline-hydrochloride salt or polyaniline-H2S0 salt.
For polyaniline-hydrochloride salt, when it reacts with concentrated sulfuric acid, polyaniline-hydrochloride salt changes into polyaniline-H2S0 salt. Additionally, hydrogenchloride gas is generated, whish is easily evaporated on the way of preparation of spinning solution. For polyaniline-H2S04 salt, it is easily dissolved in concentrated sulfuric acid and spinning solution is also easily fabricated.
Brief Description of Drawings
Figure 1 illustrates the comparison of the process between the existing and the present invention fabrication method of polyaniline and polyaniline blend spinning solution. Figure 1 illustrates the comparison of the process of the fabrication method of polyaniline, polyaniline blend spinning solution.
Best Mode for Carrying Out the Invention
The composition of matter and process of this invention are further illustrated in the following examples.
Example 1. Preparation of polyaniline spinning solution from polyaniline hydrochlride salt. 40ml(0.22 mol) of purified aniline was added in IM aqueous hydrochloric acid solution and kept at 0 °C . 23g of oxidant (NH 2S2O8 was added and kept at 0°C in 400ml of IM aqueous hydrocholric acid solution. Then oxidant solution was gradually added into aniline solution for 2 minutes, when two solutions reached at temperature equilibrium. After stirring for 90 minutes at 0°C , polyaniline-hydrochloride salt was filtered and dried. After dissolving 15g of polyaniline hydrochloride salt in 85g concentrated sulfuric acid(above 98% w/w), hydrogen chloride gas was evaporated in air-free bath. Then, polyaniline fiber was obtained by spinning under nitrogen gas pressure in coagulating bath including distilled water and air dried for 2 days. The fiber prepared exhibited a conductivity of 10 S/cm.
Example 2. Preparation of polyaniline spinning solution from polyanilme-H2S04 salt.
40ml(0.22 mol) of purified aniline was added in IM aqueous sulfuric acid solution and kept at 0 degree C. 23g of oxidant (NH4)2S2θ8 was added and kept at 0°C in 400ml of IM aqueous sulfuric acid solution. Then oxidant solution was gradually added into aniline solution for 2 minutes, when two solutions reached at temperature equilibrium. After stirring for 90 minutes at 0°C , polyaniline-H2S04 salt was filtered and dried. After dissolving 15g of polyaniline-H2S0 salt in 85g concentrated sulfuric acid(above 98% w/w), polyaniline fiber was obtained by spinning under nitrogen gas pressure in coagulating bath including distilled water and air dried for 2 days. The fiber prepared exhibited a conductivity of 10 S/cm.
Example 3. Preparation of polyaniline blend spinning solution from polyaniline hydrochloride salt.
40ml(0.22 mol) of purified aniline was added in IM aqueous hydrochloric acid solution and kept at 0 °C . 23g of oxidant (NH )2S2θs was added and kept at 0°C . in 400ml of IM aqueous hydrocholric acid solution. Then oxidant solution was gradually added into aniline solution for 2 minutes, when two solutions reached at temperature equilibrium. After stirring for 90 minutes at 0°C , polyaniline hydrochloride salt was filtered and dried. After dissolving 15g of polyaniline hydrochloride salt in 85g concentrated sulfuric acid(above 98% w/w), hydrogen chloride gas was evaporated in air-free bath. (solution A)
Dissolve 15g of Aramid pulp in 85g of concentrated sulfuric acid(above 98% w/w). (solution B) Mix solution A and solution B at the ratio of 9:1, 8:2, 7:3, 6:4, 5:5, 4:6, 3:7, 2:8 and 1 :9, respectively. Polyaniline aramid fiber was obtained by spinning under nitrogen gas pressure in coagulating bath including distilled water. The composite fibers were dried in the air for 2 days and had the conductivity as illustrated in Table 1. The conductivity studies indicated that there wasn't any variation among fibers up to 5: 5 ratio, there was a sudden drop above that ratio, according to the increase of aramid.
Example 4. Preparation of polyaniline blend spinning solution from polyaniline-H-2S0 salt.
40ml(0.22 mol) of purified aniline was added in IM aqueous sulfuric acid solution and kept at 0 °C . 23g of oxidant (NH^SaOs was added and kept at 0°C . in 400ml of IM aqueous sulfuric acid solution. Then oxidant solution was gradually added into aniline solution for 2 minutes, when two solutions reached at temperature equilibrium. After stirring for 90 minutes at 0°C , polyaniline sulfate was filtered and dried. After dissolving 15g of polyaniline~H2S0 salt in 85g concentrated sulfuric acid(above 98% w/w). (solution A)
Dissolve 15g of Aramid pulp in 85g of concentrated sulfuric acid(above 98% w/w). (solution B) Mix solution A and solution B at the ratio of 9: 1, 8:2, 7:3, 6:4, 5: 5, 4:6, 3:7, 2:8 and 1:9, respectively. Polyaniline aramid fiber was obtained by spinning under nitrogen gas pressure in coagulating bath including distilled water. The composite fibers were dried in the air for 2 days and had the conductivity as illustrated in Table 1. The conductivity studies indicated that there wasn't any variation among fibers up to 5:5 ratio, there was a sudden drop above that ratio, according to the increase of aramid.
Industrial Applicability
As mentioned before, the present invention relates to the fabrication method of polyaniline, polyaniline blend spinning solution using the product of polyaniline salt. That is, this invention refers to the fabrication method of conductive polymer fibers which is characterized by the simplicity of process and cut down expenses using the first polyaniline salt in the first step of polyaniline preparation. Besides, fibers that have various conductivity can be prepared by the same process.
Table 1. Electrical Conductivities of the various spinning polyaniline and polyaniline-blend Fibers
Figure imgf000012_0001

Claims

What is claimed is:
1. The fabrication method to make electrically conductive polyaniline spinning solution with dissolving directly polyaniline salt(polyaniline hydrochloride salt, polyaniline-H2S04 salt, et. al.) instead of EB(emeraldine base) in concentrated sulfuric acid(above 98% w/w).
2. The fabrication method to make electrically conductive polyaniline -blend(Nylon, aramid) spinning solution with dissolving directly polyaniline salt(polyaniline hydrochloride salt, polyaniline-H2S04 salt, et. al.) instead of EB(erneraldine base) in concentrated sulfuric acid(above 98% w/w).
3. The weight % of polyaniline salt in the spinning solution is from 1 to 99.9 on weight % of blend materiaKNylon, aramid)
PCT/KR2001/001568 2000-09-20 2001-09-19 Fabrication method of conductive polyaniline spinning solution WO2002024989A1 (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100401349B1 (en) * 2000-09-20 2003-10-17 스마트텍 주식회사 Fabrication Method of Conductive Polyaniline Spinning Solution
CN105113050A (en) * 2015-09-06 2015-12-02 天津工业大学 Method for preparing conductive polymer/adhesive hybrid fiber through blending spinning

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101277436B1 (en) 2010-10-15 2013-06-20 한국전기안전공사 Conductive fiber, the method for manufacturing thereof
KR101350422B1 (en) 2012-05-31 2014-01-15 한양대학교 산학협력단 Preparation method of conductive polyaniline microfiber using microfluidics, conductive polyaniline microfiber prepared by the same, and microfluidics for preparing conductive polyaniline microfiber

Citations (5)

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Publication number Priority date Publication date Assignee Title
US5069820A (en) * 1987-08-07 1991-12-03 Allied-Signal Inc. Thermally stable forms of electrically conductive polyaniline
US5160457A (en) * 1987-08-07 1992-11-03 Allied-Signal Inc. Thermally stable forms of electrically conductive polyaniline
US5788897A (en) * 1988-08-03 1998-08-04 E. I. Du Pont De Nemours And Company Electrically conductive fibers
US5911930A (en) * 1997-08-25 1999-06-15 Monsanto Company Solvent spinning of fibers containing an intrinsically conductive polymer
US6001475A (en) * 1998-10-20 1999-12-14 E. I. Du Pont De Nemours And Company Silver-containing poly(p-phenylene terephthalamide)/sulfonated polyaniline composite fibers

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CA2309194A1 (en) * 1997-11-07 1999-05-20 Corning Communications Limited Conductive polymer compositions
KR100401349B1 (en) * 2000-09-20 2003-10-17 스마트텍 주식회사 Fabrication Method of Conductive Polyaniline Spinning Solution

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5069820A (en) * 1987-08-07 1991-12-03 Allied-Signal Inc. Thermally stable forms of electrically conductive polyaniline
US5160457A (en) * 1987-08-07 1992-11-03 Allied-Signal Inc. Thermally stable forms of electrically conductive polyaniline
US5788897A (en) * 1988-08-03 1998-08-04 E. I. Du Pont De Nemours And Company Electrically conductive fibers
US5911930A (en) * 1997-08-25 1999-06-15 Monsanto Company Solvent spinning of fibers containing an intrinsically conductive polymer
US6001475A (en) * 1998-10-20 1999-12-14 E. I. Du Pont De Nemours And Company Silver-containing poly(p-phenylene terephthalamide)/sulfonated polyaniline composite fibers

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100401349B1 (en) * 2000-09-20 2003-10-17 스마트텍 주식회사 Fabrication Method of Conductive Polyaniline Spinning Solution
CN105113050A (en) * 2015-09-06 2015-12-02 天津工业大学 Method for preparing conductive polymer/adhesive hybrid fiber through blending spinning

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AU2001292375A1 (en) 2002-04-02
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