Patent US4501876A successfully refreshed from Google Patents.
US4501876A
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Film-forming poly(conjugated polymethine-type)dye
Assignee: EIDP Inc
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Filing: 1984-03-01
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Granted: 1985-02-26
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Expires: 2004-03-01
Abstract
Abstract A poly(conjugated polymethine-type)dye which is the polycondensation reaction product in the presence of strong protic acid of an aromatic polyamine and a dicarbonyl compound. These polymers are useful in the fabrication of optical recording elements and in other electronic applications.
Inventors
- 👤 George E. Zahr
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 22:46
CPC Classifications
G; G11; G11B; G11B7/00; G11B7/24; G11B7/241; G11B7/242; G11B7/244; G11B7/245; C; C09; C09B; C09B69/00; C09B69/10; C09B69/105; G11B7/246; G11B7/247
Claims Analysis
Total Claims: 26
Claim 1
Independent Claim
116 words
A film-forming poly (conjugated polymethine-type) dye which is the polycondensation reaction product in the presence of a strong protic acid of an aromatic polyamine and a dicarbonyl compound corresponding to the formula: ##STR10## in which R 1 and R 5 are independently selected from the group consisting of --H, C 1-4 alkyl, phenyl, C 7-12 aralkyl, C 7-12 alkaryl and C 5-8 cycloalkyl and, when R 1 and R 5 are combined, C 2-5 alkylene, thus forming a C 5-8 member ring, R 2 , R 3 and R 4 are independently selected from the group consisting of --H, C 1-3 alkyl and halogen, and χ is either 0 or an integer of 1 to 3.
Claim 2
Dependent Claim
116 words
A film-forming poly (conjugated polymethine-type) dye which is the polycondensation reaction product in the presence of a strong protic acid of an aromatic polyamine and a dicarbonyl compound corresponding to the formula: ##STR10## in which R 1 and R 5 are independently selected from the group consisting of --H, C 1-4 alkyl, phenyl, C 7-12 aralkyl, C 7-12 alkaryl and C 5-8 cycloalkyl and, when R 1 and R 5 are combined, C 2-5 alkylene, thus forming a C 5-8 member ring, R 2 , R 3 and R 4 are independently selected from the group consisting of --H, C 1-3 alkyl and halogen, and χ is either 0 or an integer of 1 to 3.
Claim 3
Dependent Claim
13 words
The polymeric dye of claim 1 in which the aromatic polymamine is chromophoric.
Claim 4
Dependent Claim
16 words
The polymeric dye of claim 1 which has been formed in a highly polar aprotic solvent.
Claim 5
Dependent Claim
13 words
The polymeric dye of claim 1 in which the aromatic polyamine is thionin.
Claim 6
Dependent Claim
13 words
The polymeric dye of claim 1 in which the aromatic polyamine is N,N,N',N'-tetrakis-(p-aminophenyl)-p-phenylenediamine.
Claim 7
Dependent Claim
12 words
The polymer of claim 1 in which χ is 0 or 1.
Claim 8
Dependent Claim
12 words
The polymer of claim 1 which has been treated with an oxidant.
Claim 9
Dependent Claim
13 words
The polymer of claim 1 in which the oxidant is AgAsF 6 .
Claim 10
Dependent Claim
17 words
The polymer of claim 1 in which χ is 0 and R 1 -R 5 are --H.
Claim 11
Dependent Claim
28 words
A film of the polymer of claim 1 having a conductivity of at least about 10 -3 ohm -1 cm -1 at 23° C. and 0% relative humidity.
Claim 12
Dependent Claim
14 words
A solution of the polymer of claim 1 in a highly polar aprotic solvent.
Claim 13
Dependent Claim
25 words
The solution of claim 11 in which the aprotic solvent is selected from the group of dimethylformamide, dimethylacetamide, dimethyl sulfoxide and N-methylpyrrolidone and mixtures thereof.
Claim 14
Dependent Claim
50 words
A process for preparing the polymer of claim 1 comprising dissolving the aromatic polyamine or a salt thereof and at least a molar equivalent of the dicarbonyl compound in a highly polar aprotic solvent and adding thereto at least one mole of strong acid for each mole of aromatic polyamine.
Claim 15
Dependent Claim
13 words
The process of claim 13 wherein a film is cast from the solution.
Claim 16
Dependent Claim
24 words
The process of claim 13 wherein the strong acid is selected from the group consisting of perchloric, fluorosulfonic, trifluoromethanesulfonic and p-toluenesulfonic and hydroiodic acids.
Claim 17
Dependent Claim
22 words
The process of claim 13 wherein the solvent is selected from the group of dimethylformamide, dimethylacetamide, dimethylsulfoxide and N-methylpyrrolidone and mixtures thereof.
Claim 18
Dependent Claim
16 words
A polyazomethine salt having the formula ##STR11## wherein HX is an acid or mixture of acids.
Claim 19
Dependent Claim
16 words
A polyazomethine salt having the formula ##STR11## wherein HX is an acid or mixture of acids.
Claim 20
Dependent Claim
31 words
A film of the polyazomethine salt of claim 17 said film having a conductivity of at least about 10 -3 ohm -1 cm -1 at 23° C. and 0% relative humidity.
Claim 21
Dependent Claim
26 words
A solution of the polyazomethine salt of claim 17 in a solvent selected from the group of dimethylformamide, dimethylacetamide, dimethyl sulfoxide and N-methylpyrrolidone and mixtures thereof.
Claim 22
Dependent Claim
59 words
A process for preparing a novel polyazomethine salt solution, comprising dissolving 4,4'-diaminodiphenylamine or a salt thereof and malonaldehyde bis(dimethylacetal) in a common solvent, in proportions ranging from substantially equimolar amounts up to 1.5 mole of the malonaldehyde bis(dimethylacetal) for each mole of 4,4'-diaminodiphenylamine, and adding at least about 1 mole of a strong acid for each mole of 4,4'-diaminodiphenylamine.
Claim 23
Dependent Claim
59 words
A process for preparing a novel polyazomethine salt solution, comprising dissolving 4,4'-diaminodiphenylamine or a salt thereof and malonaldehyde bis(dimethylacetal) in a common solvent, in proportions ranging from substantially equimolar amounts up to 1.5 mole of the malonaldehyde bis(dimethylacetal) for each mole of 4,4'-diaminodiphenylamine, and adding at least about 1 mole of a strong acid for each mole of 4,4'-diaminodiphenylamine.
Claim 24
Dependent Claim
13 words
The process of claim 20 wherein a film is cast from the solution.
Claim 25
Dependent Claim
22 words
The process of claim 20 wherein the strong acid is selected from the group consisting of perchloric, fluorosulfonic, trifluoromethanesulfonic and p-toluenesulfonic acids.
Claim 26
Dependent Claim
22 words
The process of claim 20 wherein the solvent is selected from the group of dimethylformamide, dimethylacetamide, dimethylsulfoxide and N-methylpyrrolidone and mixtures thereof.
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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) | 1988-02-26 | 1988-08-27 | 1989-02-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-02-26 | 1992-08-27 | 1993-02-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-02-26 | 1996-08-27 | 1997-02-26 | $7700.00 | Window Closed / Lapsed |