US4599194A
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Simultaneous polymerization, doping and solubilization of heterocyclic polymers, solutions and cast articles
Assignee: Honeywell International Inc
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Filing: 1984-06-18
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Granted: 1986-07-08
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Expires: 2004-06-18
Abstract
Abstract Polymer solutions are formed by reacting an aromatic heterocyclic such as thiophene, substituted thiophenes or oligomers of either with an acceptor doping agent (Lewis Acid) such as arsenic pentafluoride in the presence of certain solvents such as arsenic trifluoride. Articles such as air-stable conductive poly(3-methylthiophene) are cast from such solutions.
Inventors
- 👤 Jane E. Frommer
- 👤 Ronald L. Elsenbaumer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-25 17:33
CPC Classifications
H; H01; H01B; H01B1/00; H01B1/06; H01B1/12; H01B1/124; H01B1/127; C; C08; C08G; C08G61/00; C08G61/12; C08G61/122; C08G61/123; H01B1/128
Claims Analysis
Total Claims: 35
Claim 1
Independent Claim
128 words
A method of forming a solution which comprises reacting at least one monomer selected from the group consisting of heterocyclic aromatics having at least one chalcogenide, nitrogen or phosphorus heteroatom, or oligomers of such heterocyclic aromatics with an electron acceptor doping agent in the presence of a solvent selected from the group consisting of arsenic trifluoride, arsenic trichloride, arsenic tribromide, phosphorus trifluoride, phosphorus pentafluoride, phosphorus trichloride, phosphorus oxytrichloride, titanium tetrachloride, boron trifluoride, boron trichloride, boron tribromide, antimony trichloride, antimony pentachloride, and volatile chloroalkanes, the solvent being present in an amount sufficient to form a solution having a viscosity less than about 1000 centipoise, the resulting solution containing a polymer with repeat units derived from the monomer at least partially doped by a dopant derived from the doping agent.
Claim 2
Independent Claim
128 words
A method of forming a solution which comprises reacting at least one monomer selected from the group consisting of heterocyclic aromatics having at least one chalcogenide, nitrogen or phosphorus heteroatom, or oligomers of such heterocyclic aromatics with an electron acceptor doping agent in the presence of a solvent selected from the group consisting of arsenic trifluoride, arsenic trichloride, arsenic tribromide, phosphorus trifluoride, phosphorus pentafluoride, phosphorus trichloride, phosphorus oxytrichloride, titanium tetrachloride, boron trifluoride, boron trichloride, boron tribromide, antimony trichloride, antimony pentachloride, and volatile chloroalkanes, the solvent being present in an amount sufficient to form a solution having a viscosity less than about 1000 centipoise, the resulting solution containing a polymer with repeat units derived from the monomer at least partially doped by a dopant derived from the doping agent.
Claim 3
Dependent Claim
57 words
The method of claim 1 wherein the monomer is a five-member monoheterocyclic aromatic of the formula: ##STR3## wherein X is S, O, Se, NH, NR', PH or PR'; R 1 is H alkyl, --OR, --SR or aryl; R 2 is H, alkyl --OR, --SR or aryl, R is alkyl or aryl; and R' is alkyl or aryl.
Claim 4
Dependent Claim
9 words
The method of claim 2 wherein X is S.
Claim 5
Dependent Claim
27 words
The method of claim 3 wherein R 1 and R 2 are each H, alkyl of 1-6 carbons, oxyalkyl of 1-6 carbons or thioalkyl of 1-6 carbons.
Claim 6
Dependent Claim
10 words
The method of claim 4 wherein the monomer is thiophene.
Claim 7
Dependent Claim
10 words
The method of claim 4 wherein the monomer is 3-methylthiophene.
Claim 8
Dependent Claim
10 words
The method of claim 4 wherein the monomer is 3,4-dimethylthiophene.
Claim 9
Dependent Claim
11 words
The method of claim 4 wherein the solvent is arsenic trifluoride.
Claim 10
Dependent Claim
11 words
The method of claim 3 wherein the solvent is arsenic trifluoride.
Claim 11
Dependent Claim
9 words
The method of claim 2 wherein X is NR'.
Claim 12
Dependent Claim
14 words
The method of claim 2 wherein R' is alkyl of 1-6 carbons or phenyl.
Claim 13
Dependent Claim
11 words
The method of claim 11 wherein the solvent is arsenic trifluoride.
Claim 14
Dependent Claim
34 words
The method of claim 11 wherein one of R 1 and R 2 is alkyl of 1-6 carbons, and the other of R 1 and R 2 is H or alkyl of 1-6 carbons.
Claim 15
Dependent Claim
58 words
The method of claim 1 comprising reacting an oligomer of a five-membered monoheterocyclic aromatic of the formula: ##STR4## wherein X is S, O, Se, NH, NR', PH or PR'; R 1 is H alkyl, --OR; --SR or aryl; R 2 is H. alkyl --OR, --SR or aryl; R is alkyl or aryl; and R' is alkyl or aryl.
Claim 16
Dependent Claim
15 words
The method of claim 1 wherein the doping agent is a group V metal pentahalide.
Claim 17
Dependent Claim
14 words
The method of claim 15 wherein the group V metal pentahalide is arsenic pentafluoride.
Claim 18
Dependent Claim
78 words
A solution comprising a solvent selected from the group consisting of arsenic trifluoride, arsenic trichloride, arsenic tribromide, phosphorus trichloride, phosphorus pentafluoride, phosphorus trifluoride, phosphorus oxytrichloride, titanium tetrachloride, boron trifluoride, boron trichloride, boron tribromide, antimony trichloride, antimony pentachloride, and volatile chloroaklanes, a polymer solute consisting essentially of heterocyclic aromatic repeating units with heteroatoms being chalcogenide, nitrogen or phosphorus lined by carbon-carbon or heteroatom-carbon bonds between atoms of adjacent rings, and a dopant solute derived from an acceptor doping agent.
Claim 19
Dependent Claim
78 words
A solution comprising a solvent selected from the group consisting of arsenic trifluoride, arsenic trichloride, arsenic tribromide, phosphorus trichloride, phosphorus pentafluoride, phosphorus trifluoride, phosphorus oxytrichloride, titanium tetrachloride, boron trifluoride, boron trichloride, boron tribromide, antimony trichloride, antimony pentachloride, and volatile chloroaklanes, a polymer solute consisting essentially of heterocyclic aromatic repeating units with heteroatoms being chalcogenide, nitrogen or phosphorus lined by carbon-carbon or heteroatom-carbon bonds between atoms of adjacent rings, and a dopant solute derived from an acceptor doping agent.
Claim 20
Dependent Claim
54 words
The solution of claim 17 wherein the repeating units are of the formula: ##STR5## wherein X is S, O, Se, NH, NR', PH or PR'; R 1 is H alkyl, --OR, --SR or aryl; R 2 is H, alkyl --OR, --SR or aryl; R is alkyl or aryl; and R' is alkyl or aryl.
Claim 21
Dependent Claim
9 words
The solution of claim 18 wherein X is S.
Claim 22
Dependent Claim
27 words
The solution of claim 19 wherein R 1 and R 2 are each H, alkyl of 1-6 carbons, oxyalkyl of 1-6 carbons or thioalkyl of 1-6 carbons.
Claim 23
Dependent Claim
14 words
The solution of claim 20 wherein R 1 and R 2 are each H.
Claim 24
Dependent Claim
30 words
The solution of claim 20 wherein, for each repeating unit, one of R 1 and R 2 is H and the other of R 1 and R 2 is methyl.
Claim 25
Dependent Claim
17 words
The solution of claim 10 wherein R 1 and R 2 are each alkyl of 1-6 carbons.
Claim 26
Dependent Claim
11 words
The solution of claim 20 wherein the solvent is arsenic trifluoride.
Claim 27
Dependent Claim
11 words
The solution of claim 19 wherein the solvent is arsenic trifluoride.
Claim 28
Dependent Claim
9 words
The solution of claim 18 wherein X is NR'.
Claim 29
Dependent Claim
14 words
The solution of claim 26 wherein R' is alkyl of 1-6 carbons or phenyl.
Claim 30
Dependent Claim
11 words
The solution of claim 27 wherein the solvent is arsenic trifluoride.
Claim 31
Dependent Claim
34 words
The solution of claim 27 wherein one of R 1 and R 2 is alkyl of 1-6 carbons and the other of R 1 and R 2 is H or alkyl of 1-6 carbons.
Claim 32
Dependent Claim
17 words
The solution of claim 17 wherein the dopant solute is derived from a group V metal pentahalide.
Claim 33
Dependent Claim
14 words
The solution of claim 30 wherein the group V metal pentahalide is arsenic pentafluoride.
Claim 34
Dependent Claim
13 words
An article prepared by evaporating the solvent from the solution of claim 17.
Claim 35
Dependent Claim
16 words
An article prepared by evaporating solvent from a solution prepared by the method of claim 1.
References Cited (Backward Citations)
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