US4847115A
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Chemical synthesis of conducting polypyrrole using uniform oxidant/dopant reagents
Assignee: Boeing North American Inc
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Filing: 1987-08-10
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Granted: 1989-07-11
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Expires: 2007-08-10
Abstract
Abstract A method for producing oxidant/dopant reagent solutions which comprises reacting a basic ferric carboxylate, preferably basic ferric acetate, with an alkyl or aryl sulfonic acid, e.g., benzenesulfonic acid, to produce the corresponding ferric sulfonate in solution. Oxidant/dopant solutions can also be prepared containing cupric or ceric sulfonates. The oxidant/dopant solution is employed in situ for reaction with a pyrrole to produce electrically conductive polypyrrole. A porous substrate, such as fiberglass cloth, can be dipped in the oxidant/dopant solution, dried and then treated with a pyrrole to produce an electrically conductive polypyrrole deposit in the interstices of the substrate.
Inventors
- 👤 Leslie F. Warren
- 👤 Dennis R. Strauss
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 23:06
CPC Classifications
C; C08; C08G; C08G61/00; C08G61/12; C08G61/122; C08G61/123; C08G61/124; H; H01; H01B; H01B1/00; H01B1/06; H01B1/12; H01B1/124; H01B1/127
Claims Analysis
Total Claims: 36
Claim 1
Independent Claim
73 words
In the process for producing conductive polypyrrole by reaction of pyrrole and an oxidant/dopant, the improvement which comprises producing said oxidant/dopant by reaction of a basic metal carboxylate selected from the group consisting of basic ferric, cupric and ceric carboxylates, with an effective amount of a sulfonic acid selected from the group consisting of alkyl and aryl sulfonic acids, and recovering an oxidant/dopant reagent solution containing the corresponding metal sulfonate as the oxidant/dopant.
Claim 2
Dependent Claim
73 words
In the process for producing conductive polypyrrole by reaction of pyrrole and an oxidant/dopant, the improvement which comprises producing said oxidant/dopant by reaction of a basic metal carboxylate selected from the group consisting of basic ferric, cupric and ceric carboxylates, with an effective amount of a sulfonic acid selected from the group consisting of alkyl and aryl sulfonic acids, and recovering an oxidant/dopant reagent solution containing the corresponding metal sulfonate as the oxidant/dopant.
Claim 3
Dependent Claim
21 words
The process of claim 1, employing a stoichiometric amount of said sulfonic acid, said reaction taking place in a suitable solvent.
Claim 4
Dependent Claim
14 words
The process of claim 1, said basic metal carboxylate being a basic ferric carboxylate.
Claim 5
Dependent Claim
23 words
The process of claim 3, said basic ferric carboxylate selected from the group consisting of basic ferric formate, acetate, propionate, butyrate and benzoate.
Claim 6
Dependent Claim
13 words
The process of claim 4, said basic ferric carboxylate being basic ferric acetate.
Claim 7
Dependent Claim
24 words
The process of claim 1, said sulfonic acid being an alkyl sulfonic acid, the alkyl group having from 1 to about 18 carbon atoms.
Claim 8
Dependent Claim
31 words
The process of claim 1, said sulfonic acid selected from the group consisting of benzenesulfonic acid, 4-ethylbenzenesulfonic acid, 4-chlorobenzenesulfonic acid, dodecylbenzenesulfonic acid, methylsulfonic acid, perfluorooctylsulfonic acid, 4-methylbenzenesulfonic acid, and 2-naphthalenesulfonic acid.
Claim 9
Dependent Claim
22 words
The process of claim 7, said sulfonic acid selected from the group consisting of benzenesulfonic acid, 4-ethylbenzenesulfonic, 4-chlorobenzenesulfonic acid, and dodecylbenzenesulfonic acid.
Claim 10
Dependent Claim
23 words
The process of claim 7, said reaction taking place in a solvent selected from the group consisting of methanol, ethanol, acetonitrile and dioxane.
Claim 11
Dependent Claim
43 words
The process of claim 7, said basic metal carboxylate being basic ferric acetate and employing 3 equivalents of said sulfonic acid per iron atom, said reaction taking place at a temperature ranging from ambient temperature to about 40° C. in a methanol solution.
Claim 12
Dependent Claim
75 words
A process for producing electrically conductive polypyrrole which comprises: reacting a basic metal carboxylate selected from the group consisting of basic ferric, cupric and ceric carboxylates with an effective amount of a sulfonic acid selected from the group consisting of alkyl and aryl sulfonic acids, and recovering an oxidant/dopant reagent solution containing the corresponding metal sulfonate as the oxidant/dopant, reacting said oxidant/dopant reagent solution in situ with a pyrrole, and precipitating a conductive polypyrrole solid.
Claim 13
Dependent Claim
75 words
A process for producing electrically conductive polypyrrole which comprises: reacting a basic metal carboxylate selected from the group consisting of basic ferric, cupric and ceric carboxylates with an effective amount of a sulfonic acid selected from the group consisting of alkyl and aryl sulfonic acids, and recovering an oxidant/dopant reagent solution containing the corresponding metal sulfonate as the oxidant/dopant, reacting said oxidant/dopant reagent solution in situ with a pyrrole, and precipitating a conductive polypyrrole solid.
Claim 14
Dependent Claim
23 words
The process of claim 11, said basic ferric carboxylate selected from the group consisting of basic ferric formate, acetate, propionate, butyrate and benzoate.
Claim 15
Dependent Claim
21 words
The process of claim 11, employing a stoichiometric amount of said sulfonic acid, said reaction taking place in a suitable solvent.
Claim 16
Dependent Claim
14 words
The process of claim 13, said basic metal carboxylate being a basic ferric carboxylate.
Claim 17
Dependent Claim
31 words
The process of claim 11, said sulfonic acid selected from the group consisting of benzenesulfonic acid, 4-ethylbenzenesulfonic acid, 4-chlorobenzenesulfonic acid, dodecylbenzenesulfonic acid, methylsulfonic acid, perfluorooctylsulfonic acid, 4-methylbenzenesulfonic acid, and 2-naphthalenesulfonic acid.
Claim 18
Dependent Claim
43 words
the process of claim 15, said basic metal carboxylate being basic ferric acetate and employing 3 equivalents of said sulfonic acid per iron atom, said reaction taking place at a temperature ranging from ambient temperature to about 40° C. in a methanol solution.
Claim 19
Dependent Claim
17 words
The process of claim 11, said pyrrole being a neat pyrrole or a pyrrole in a solvent.
Claim 20
Dependent Claim
27 words
The process of claim 11, said pyrrole 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 21
Dependent Claim
42 words
The process of claim 18, the concentration of the oxidant/dopant in the reaction mixture containing the pyrrole ranging from about 0.01 to about 2 molar, and the concentration of the pyrrole in the reaction mixture ranging from about 0.01 to 2 molar.
Claim 22
Dependent Claim
60 words
The process of claim 19, said sulfonic acid selected from the group consisting of benzenesulfonic acid, 4-ethylbenzenesulfonic, 4-chlorobenzenesulfonic acid, and dodecylbenzenesulfonic acid, said basic metal carboxylate being basic ferric acetate and employing 3 equivalents of said sulfonic acid per iron atom, said reaction taking place at a temperature ranging from ambient temperature to about 40° C. in a methanol solution.
Claim 23
Dependent Claim
87 words
A process for producing electrically conductive polypyrrole material which comprises: reacting a basic metal carboxylate selected from the group consisting of basic ferric, cupric and ceric carboxylates with an effective amount of a sulfonic acid selected from the group consisting of alkyl and aryl sulfonic acids, and recovering an oxidant/dopant reagent solution containing the corresponding metal sulfonate as the oxidant/dopant, contacting a porous substrate with said oxidant/dopant reagent solution, drying said substrate, contacting said substrate with a pyrrole, and oxidizing said pyrrole to polypyrrole on said substrate.
Claim 24
Dependent Claim
87 words
A process for producing electrically conductive polypyrrole material which comprises: reacting a basic metal carboxylate selected from the group consisting of basic ferric, cupric and ceric carboxylates with an effective amount of a sulfonic acid selected from the group consisting of alkyl and aryl sulfonic acids, and recovering an oxidant/dopant reagent solution containing the corresponding metal sulfonate as the oxidant/dopant, contacting a porous substrate with said oxidant/dopant reagent solution, drying said substrate, contacting said substrate with a pyrrole, and oxidizing said pyrrole to polypyrrole on said substrate.
Claim 25
Dependent Claim
21 words
The process of claim 21, employing a stoichiometric amount of said sulfonic acid, said reaction taking place in a suitable solvent.
Claim 26
Dependent Claim
14 words
The process of claim 22, said basic metal carboxylate being a basic ferric carboxylate.
Claim 27
Dependent Claim
31 words
The process of claim 21, said sulfonic acid selected from the group consisting of benzenesulfonic acid, 4-ethylbenzenesulfonic acid, 4-chlorobenzenesulfonic acid, dodecylbenzenesulfonic acid, methylsulfonic acid, perfluorooctylsulfonic acid, 4-methylbenzenesulfonic acid, and 2-naphthalenesulfonic acid.
Claim 28
Dependent Claim
43 words
The process of claim 24, said basic metal carboxylate being basic ferric acetate and employing 3 equivalents of said sulfonic acid per iron atom, said reaction taking place at a temperature ranging from ambient temperature to about 40° C. in a methanol solution.
Claim 29
Dependent Claim
17 words
The process of claim 21, said pyrrole being a liquid pyrrole or a pyrrole in vapor form.
Claim 30
Dependent Claim
28 words
The process of claim 21, 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 31
Dependent Claim
23 words
The process of claim 27, said pyrrole contained in a solvent selected from the group consisting of cyclohexane, alcohols, dioxane, acetonitrile and water.
Claim 32
Dependent Claim
87 words
A process for producing electrically conductive polypyrrole material which comprises: reacting a basic metal carboxylate selected from the group consisting of basic ferric, cupric and ceric carboxylates with an effective amount of a sulfonic acid selected from the group consisting of alkyl and aryl sulfonic acids, and recovering an oxidant/dopant reagent solution containing the corresponding metal sulfonate as the oxidant/dopant, contacting a porous substrate with a pyrrole, drying said substrate, contacting said substrate with said oxidant/dopant reagent solution, and oxidizing said pyrrole to polypyrrole on said substrate.
Claim 33
Dependent Claim
87 words
A process for producing electrically conductive polypyrrole material which comprises: reacting a basic metal carboxylate selected from the group consisting of basic ferric, cupric and ceric carboxylates with an effective amount of a sulfonic acid selected from the group consisting of alkyl and aryl sulfonic acids, and recovering an oxidant/dopant reagent solution containing the corresponding metal sulfonate as the oxidant/dopant, contacting a porous substrate with a pyrrole, drying said substrate, contacting said substrate with said oxidant/dopant reagent solution, and oxidizing said pyrrole to polypyrrole on said substrate.
Claim 34
Dependent Claim
31 words
The process of claim 29, said sulfonic acid selected from the group consisting of benzenesulfonic acid, 4-ethylbenzenesulfonic acid, 4-chlorobenzenesulfonic acid, dodecylbenzenesulfonic acid, methylsulfonic acid, perfluorooctylsulfonic acid, 4-methylbenzenesulfonic acid, and 2-naphthalenesulfonic acid.
Claim 35
Dependent Claim
43 words
The process of claim 30, said basic metal carboxylate being basic ferric acetate and employing 3 equivalents of said sulfonic acid per iron atom, said reaction taking place at a temperature ranging from ambient temperature to about 40° C. in a methanol solution.
Claim 36
Dependent Claim
28 words
The process of claim 31, 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.
References Cited (Backward Citations)
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