US5095076A
Expired / Lapsed
US
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Preparation of highly soluble conductive polymer materials
Assignee: Lockheed Martin Corp
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Filing: 1990-11-05
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Granted: 1992-03-10
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Expires: 2010-11-05
Abstract
Abstract Preparation of conductive polymers, particularly polyanilines having good solubility in organic solvents and high electrical conductivity, by providing a mixture of aniline, dianiline and a flexible diamine such as 1,3-bis (3-aminophenoxy)benzene or triethylene tetramine. The mixture is reacted in the presence of an oxidant such as ammonium persulfate and a protonic (Bronsted) acid, e.g. tosic acid, to polymerize the mixture and form a conductive polyaniline in which the conjugation is interrupted by an intermediate diamine group, and which renders the resulting polymer more flexible than polyaniline per se. The conductive polymer so produced also has terminal primary amino groups which aid solubility and which are further reactive. The conductive polyaniline product of the invention can be blended with non-conductive resins such as polyimides to provide cured conductive resin blends having good mechanical properties.
Inventors
- 👤 Sandra K. Clement
- 👤 Deanne P. Yamato
- 👤 Randy E. Cameron
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 05:25
CPC Classifications
H; H01; H01B; H01B1/00; H01B1/06; H01B1/12; H01B1/124; H01B1/128; C; C08; C08L; C08L77/00; C08L77/02; Y; Y10; Y10S; Y10S525/00; Y10S525/928
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
53 words
A soluble conductive polyaniline having the formula ##STR3## where R is an organic group in the form of a flexible segment derived from an organic diamine and that is more flexible than polyaniline itself, and which interrupts the conjugation of the adjacent polyaniline groups. and x ranges from about 8 to about 200.
Claim 2
Dependent Claim
53 words
A soluble conductive polyaniline having the formula ##STR3## where R is an organic group in the form of a flexible segment derived from an organic diamine and that is more flexible than polyaniline itself, and which interrupts the conjugation of the adjacent polyaniline groups. and x ranges from about 8 to about 200.
Claim 3
Dependent Claim
15 words
The polymer of claim 1, wherein R is an aromatic group or an aliphatic group.
Claim 4
Dependent Claim
22 words
The polymer of claim 2, wherein R is selected from the class consisting of bis(phenoxy)benzene, methylene diphenyl, dodecane, ethyleneimine and oxydiphenyl groups.
Claim 5
Dependent Claim
12 words
The polymer of claim 3, wherein R is a bis(phenoxy) benzene group.
Claim 6
Dependent Claim
12 words
The polymer of claim 3, wherein R is a triethylene tetramine group.
Claim 7
Dependent Claim
22 words
A blend of (a) a conductive polyaniline as defined in claim 1 and (b) a suitable non-conductive resin, in a suitable solvent.
Claim 8
Dependent Claim
30 words
A blend of (a) a conductive polymer as defined in claim 2, and (b) a non-conductive resin selected from the group consisting of epoxies, maleimides, polyimides, polyamides, polyethers and polythioethers.
Claim 9
Dependent Claim
20 words
A blend of (a) a conductive polymer as defined in claim 3, and (b) a polyimide, in a suitable solvent.
Claim 10
Dependent Claim
20 words
A blend of (a) a conductive polymer as defined in claim 5, and (b) a polyimide, in a suitable solvent.
Claim 11
Dependent Claim
19 words
A cured blend of (a) a conductive polyaniline as defined in claim 1 and (b) a suitable non-conductive resin.
Claim 12
Dependent Claim
31 words
A cured blend of (a) a conductive polymer as defined in claim 2, and (b) a non-conductive resin selected from the group consisting of epoxies, maleimides, polyimides, polyamides, polyethers and polythioethers.
Claim 13
Dependent Claim
17 words
A cured blend of (a) a conductive polymer as defined in claim 3, and (b) a polyimide.
Claim 14
Dependent Claim
57 words
A process for producing a conductive polyaniline having good solubility and conductivity which comprises providing a mixture of aniline, dianiline and a flexible diamine, reacting said mixture in the presence of an oxidant and a protonic acid to polymerize said mixture, and forming a conductive polyaniline in which the conjugation is interrupted by an intermediate diamine group.
Claim 15
Dependent Claim
57 words
A process for producing a conductive polyaniline having good solubility and conductivity which comprises providing a mixture of aniline, dianiline and a flexible diamine, reacting said mixture in the presence of an oxidant and a protonic acid to polymerize said mixture, and forming a conductive polyaniline in which the conjugation is interrupted by an intermediate diamine group.
Claim 16
Dependent Claim
43 words
The process of claim 13, said reaction taking place in aqueous medium and employing the following molar proportions of the reactants about 8 to about 9.5 mols aniline about 0.5 to about 2.0 mols dianiline about 0.01 to about 0.03 mol flexible diamine
Claim 17
Dependent Claim
33 words
The process of claim 13, said flexible diamine being selected from the group consisting of 1,3-bis (3-aminophenoxy)benzene, oxydianiline, methylene dianiline, 2,2'-bis [(4-aminophenoxy)-4 phenyl] hexafluoro propane 1,12 diamino dodecane, diethylene triamine and triethylene tetramine.
Claim 18
Dependent Claim
10 words
The process of claim 13, said flexible diamine being 1,3-bis(3-aminophenoxy)benzene.
Claim 19
Dependent Claim
11 words
The process of claim 13, said flexible diamine being triethylene tetramine.
Claim 20
Dependent Claim
11 words
The process of claim 15, wherein said oxidant is ammonium persulfate.
Claim 21
Dependent Claim
21 words
The process of claim 15, wherein said oxidant is selected from the group consisting of benzoperoxide, o-chloranil, p-chloranil and cupric chloride.
Claim 22
Dependent Claim
28 words
The process of claim 12, wherein said protonic acid is selected from the group consisting of hydrochloric acid, sulfuric acid, formic acid, tosic acid and benzene disulfonic acid.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1995-03-10 | 1995-09-09 | 1996-03-10 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-03-10 | 1999-09-09 | 2000-03-10 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-03-10 | 2003-09-09 | 2004-03-10 | $7700.00 | Window Closed / Lapsed |