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US4697001A
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Chemical synthesis of conducting polypyrrole
Assignee: Boeing North American Inc
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Filing: 1986-10-09
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Granted: 1987-09-29
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Expires: 2006-10-09
Abstract
Abstract Production of electrically conductive polypyrrole of enhanced stability by treating a liquid pyrrole with a solution of a strong oxidant, capable of oxidizing pyrrole to a pyrrole polymer, and oxidizing the pyrrole by such strong oxidant in the presence of a relatively large organic dopant anion, and precipitating a conductive polypyrrole. The strong oxidant, e.g., Fe 3+ ion, and dopant anion, which can be an alkyl or aryl sulfonate, e.g., methylbenzenesulfonate, or a perfluorinated carboxylate, e.g., trifluoroacetate, anion, can be derived from a single compound, e.g., ##STR1## the anion serving as dopant for the polypyrrole.
Inventors
- 👤 John A. Walker
- 👤 Edward F. Witucki
- 👤 Leslie F. Warren
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 12:57
CPC Classifications
H; H01; H01B; H01B1/00; H01B1/14; C; C08; C08G; C08G61/00; C08G61/12; C08G61/122; C08G61/123; C08G61/124; H01B1/06; H01B1/12; H01B1/124; H01B1/127; H05; H05K; H05K3/00; H05K3/10; H05K3/18; H05K3/188; H05K1/00; H05K1/02; H05K1/09; Y; Y10; Y10T; Y10T442/00; Y10T442/20; Y10T442/2418; Y10T442/2459
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
94 words
A process for producing electrically conductive polypyrrole which comprises: treating a liquid pyrrole with a solution of a strong oxidant capable of oxidizing pyrrole to a pyrrole polymer, said strong oxidant being a cation selected from the group consisting of Fe 3+ , Cu 2+ , Ce 4+ , and (C 6 H 5 ) 3 C + cations, oxidizing said pyrrole by said strong oxidant in the presence of a dopant anion selected from the group consisting of (1) alkyl and aryl sulfonates and (2) fluorinated carboxylates, and precipitating a conductive polypyrrole solid.
Claim 2
Dependent Claim
94 words
A process for producing electrically conductive polypyrrole which comprises: treating a liquid pyrrole with a solution of a strong oxidant capable of oxidizing pyrrole to a pyrrole polymer, said strong oxidant being a cation selected from the group consisting of Fe 3+ , Cu 2+ , Ce 4+ , and (C 6 H 5 ) 3 C + cations, oxidizing said pyrrole by said strong oxidant in the presence of a dopant anion selected from the group consisting of (1) alkyl and aryl sulfonates and (2) fluorinated carboxylates, and precipitating a conductive polypyrrole solid.
Claim 3
Dependent Claim
28 words
The process of claim 1, said pyrrole monomer selected from the group consisting of pyrrole, a 3- and 3,4-alkyl and aryl C-substituted pyrrole, an N-alkylpyrrole and an N-arylpyrrole.
Claim 4
Dependent Claim
41 words
The process of claim 1, said oxidant being present in a concentration in the range of about 0.001 to about 2 molar, and said dopant anion being present in a concentration in the range from about 0.001 to about 2 molar.
Claim 5
Dependent Claim
19 words
The process of claim 1, said dopant anion being selected from the class consisting of alkyl or aryl sulfonates.
Claim 6
Dependent Claim
23 words
The process of claim 4, said dopant anion being an alkyl sulfonate, the alkyl group having from 1 to about 18 carbon atoms.
Claim 7
Dependent Claim
14 words
The process of claim 4, said dopant anion being a benzenesulfonate or a naphthalenesulfonate.
Claim 8
Dependent Claim
32 words
The process of claim 1, said oxidant and said dopant anion being provided by a compound selected from the group consisting of the ferric salts of methylbenzenesulfonate, ethylbenzenesulfonate, dodecylbenzenesulfonate, perfluorooctylsulfonate, and naphthalenesulfonate.
Claim 9
Dependent Claim
20 words
The process of claim 1, said dopant anion being selected from the group consisting of the trifluoroacetate and perfluorobutyrate ions.
Claim 10
Dependent Claim
29 words
The process of claim 1, said oxidant and said dopant anion being provided by a compound selected from the group consisting of the ferric salts of trifluoroacetate and perfluorobutyrate.
Claim 11
Dependent Claim
34 words
The process of claim 1, the reaction being carried out in aqueous or organic solvent medium in which said pyrrole and said oxidant are soluble and which does not interfere with the oxidation reaction.
Claim 12
Dependent Claim
128 words
A process for producing electrically conductive polypyrrole which comprises: contacting a pyrrole and a strong oxidant capable of oxidizing pyrrole to a pyrrole polymer, at substantially room temperature, in an aqueous or organic solvent medium in which said pyrrole and said oxidant are soluble and which does not interfere with the oxidation reaction, said strong oxidant being a cation selected from the group consisting of Fe 3+ , Cu 2+ , Ce 4+ , and (C 6 H 5 ) 3 C + cations, oxidizing said pyrrole by said strong oxidant in the presence of a dopant anion selected from the group consisting of (1) alkyl and aryl sulfonates and (2) fluorinated carboxylates, and precipitating a conductive polypyrrole solid comprising a pyrrole polymer cation and said dopant anion.
Claim 13
Dependent Claim
128 words
A process for producing electrically conductive polypyrrole which comprises: contacting a pyrrole and a strong oxidant capable of oxidizing pyrrole to a pyrrole polymer, at substantially room temperature, in an aqueous or organic solvent medium in which said pyrrole and said oxidant are soluble and which does not interfere with the oxidation reaction, said strong oxidant being a cation selected from the group consisting of Fe 3+ , Cu 2+ , Ce 4+ , and (C 6 H 5 ) 3 C + cations, oxidizing said pyrrole by said strong oxidant in the presence of a dopant anion selected from the group consisting of (1) alkyl and aryl sulfonates and (2) fluorinated carboxylates, and precipitating a conductive polypyrrole solid comprising a pyrrole polymer cation and said dopant anion.
Claim 14
Dependent Claim
39 words
The process of claim 11, said pyrrole being liquid pyrrole and said strong oxidant and said dopant anion being provided by a compound selected from the group consisting of the ferric salts of methylbenzenesulfonate, ethylbenzenesulfonate, dodecylbenzenesulfonate, perfluorooctylsulfonate, and naphthalenesulfonate.
Claim 15
Dependent Claim
78 words
A process for producing electrically conductive polypyrrole material which comprises: contacting a porous substrate with liquid pyrrole, contacting said substrate containing said liquid pyrrole with a solution of a strong oxidant capable of oxidizing pyrrole to a pyrrole polymer, and oxidizing said pyrrole polymer in the presence of a dopant anion selected from the group consisting of (1) alkyl and aryl sulfonates and (2) fluorinated carboxylates, and precipitating a conductive pyrrole polymer in the pores of said substrate.
Claim 16
Dependent Claim
78 words
A process for producing electrically conductive polypyrrole material which comprises: contacting a porous substrate with liquid pyrrole, contacting said substrate containing said liquid pyrrole with a solution of a strong oxidant capable of oxidizing pyrrole to a pyrrole polymer, and oxidizing said pyrrole polymer in the presence of a dopant anion selected from the group consisting of (1) alkyl and aryl sulfonates and (2) fluorinated carboxylates, and precipitating a conductive pyrrole polymer in the pores of said substrate.
Claim 17
Dependent Claim
32 words
The process of claim 13, said oxidant and said dopant anion being provided by a compound selected from the group consisting of the ferric salts of methylbenzenesulfonate, ethylbenzenesulfonate, dodecylbenzenesulfonate, perfluorooctylsulfonate, and naphthalenesulfonate.
Claim 18
Dependent Claim
11 words
An electrically conductive polypyrrole produced by the process of claim 1.
Claim 19
Dependent Claim
11 words
An electrically conductive polypyrrole produced by the process of claim 7.
Claim 20
Dependent Claim
11 words
An electrically conductive polypyrrole produced by the process of claim 9.
Claim 21
Dependent Claim
11 words
An electrically conductive polypyrrole produced by the process of claim 12.
Claim 22
Dependent Claim
11 words
An electrically conductive polypyrrole produced by the process of claim 14.
Claim 23
Dependent Claim
36 words
An electrically conductive polypyrrole having a dopant anion selected from the group consisting of methylbenzenesulfonate, ethylbenzenesulfonate, dodecylbenzenesulfonate, perfluorooctylsulfonate, and naphthalenesulfonate, said polypyrrole having an average dopant concentration of about one anion for each four pyrrole units.
Claim 24
Dependent Claim
36 words
An electrically conductive polypyrrole having a dopant anion selected from the group consisting of methylbenzenesulfonate, ethylbenzenesulfonate, dodecylbenzenesulfonate, perfluorooctylsulfonate, and naphthalenesulfonate, said polypyrrole having an average dopant concentration of about one anion for each four pyrrole units.
Claim 25
Dependent Claim
35 words
An electrically conductive polypyrrole having a dopant anion selected from the group consisting of the trifluoroacetate and perfluorobutyrate ions, said polypyrrole having an average dopant concentration of about one anion for each four pyrrole units.
Claim 26
Dependent Claim
35 words
An electrically conductive polypyrrole having a dopant anion selected from the group consisting of the trifluoroacetate and perfluorobutyrate ions, said polypyrrole having an average dopant concentration of about one anion for each four pyrrole units.
References Cited (Backward Citations)
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1990-09-28 | 1991-03-30 | 1991-09-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-09-28 | 1995-03-30 | 1995-09-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-09-28 | 1999-03-30 | 1999-09-29 | $7700.00 | Window Closed / Lapsed |