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US4607124A
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Processes for the preparation of mixed squaraine compositions
Assignee: Xerox Corp
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Filing: 1985-10-30
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Granted: 1986-08-19
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Expires: 2005-10-30
Abstract
Abstract An improved process for the preparation of mixed squaraine compositions which comprises reacting squaric acid, an aromatic amine, and a fluoroaniline, in the presence of an aliphatic alcohol, and an optional azeotropic substance. Also disclosed are mixed squaraine composition products of the following formulas: ##STR1##
Inventors
- 👤 Peter M. Kazmaier
- 👤 Giuseppa Baranyi
- 👤 Cheng-Kuo Hsiao
- 👤 Richard A. Burt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 20:20
CPC Classifications
C; C09; C09B; C09B67/00; C09B67/0033; C09B67/0034; G; G03; G03G; G03G5/00; G03G5/02; G03G5/04; G03G5/06; G03G5/0601; G03G5/0609; G03G5/0611; G03G5/0698
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
32 words
An improved process for the preparation of squaraine compositions which comprises reacting squaric acid, an aromatic amine, and a fluoroaniline, in the presence of an aliphatic alcohol, and an optional azeotropic substance.
Claim 2
Dependent Claim
32 words
An improved process for the preparation of squaraine compositions which comprises reacting squaric acid, an aromatic amine, and a fluoroaniline, in the presence of an aliphatic alcohol, and an optional azeotropic substance.
Claim 3
Dependent Claim
27 words
An improved process in accordance with claim 1 wherein the reaction is effected at a temperature of from about 50 degrees Centigrade to about 130 degrees Centigrade.
Claim 4
Dependent Claim
12 words
A process in accordance with claim 1 wherein the amine is N,N-dialkyl-m-toluidine.
Claim 5
Dependent Claim
12 words
A process in accordance with claim 1 wherein the amine is N,N-dimethyl-m-toluidine.
Claim 6
Dependent Claim
12 words
A process in accordance with claim 1 wherein the amine is N,N-dibutyl-m-toluidine.
Claim 7
Dependent Claim
12 words
A process in accordance with claim 1 wherein the fluoroaniline is N,N-dimethyl-3-fluoroaniline.
Claim 8
Dependent Claim
13 words
A process in accordance with claim 1 wherein the fluoroaniline is N,N-diethyl-3 -fluoroaniline.
Claim 9
Dependent Claim
22 words
A process in accordance with claim 1 wherein the aliphatic alcohol contains from about 1 carbon atom to about 8 carbon atoms.
Claim 10
Dependent Claim
14 words
A process in accordance with claim 1 wherein the alcohol is butanol or heptanol.
Claim 11
Dependent Claim
42 words
An improved process for the preparation of squaraine compositions which comprises reacting squaric acid, an aromatic amine, and a fluoroaniline, of the following formulas, in the presence of an aliphatic alcohol ##STR7## wherein n is a number of from zero to 2.
Claim 12
Dependent Claim
42 words
An improved process for the preparation of squaraine compositions which comprises reacting squaric acid, an aromatic amine, and a fluoroaniline, of the following formulas, in the presence of an aliphatic alcohol ##STR7## wherein n is a number of from zero to 2.
Claim 13
Dependent Claim
17 words
A process in accordance with claim 10 wherein the fluoroaniline is N,N-dimethyl-3-fluoroaniline and the amine is N,N-dimethyl-m-toluidine.
Claim 14
Dependent Claim
18 words
A process in accordance with claim 10 wherein there results as the product bis(4-N,N-dimethyl-2-methylphenyl)squaraine doped with N,N-dimethyl-3-fluoroaniline squaraines.
Claim 15
Dependent Claim
12 words
A mixed squaraine composition comprised of components I, II, and III, ##STR8##
Claim 16
Dependent Claim
12 words
A mixed squaraine composition comprised of components I, II, and III, ##STR8##
Claim 17
Dependent Claim
32 words
A composition in accordance with claim 13 wherein the components are present in the proportions I 98.50, to II 1.43, to III 0.07; to about I 41.36, II 52.20, and III 6.44.
Claim 18
Dependent Claim
23 words
A composition in accordance with claim 13 wherein the components are present in the proportion I 74.67 to II 22.71, to III 2.62.
Claim 19
Dependent Claim
20 words
The composition in accordance with claim 14 wherein the resulting mixture has increased spectral response in the blue wavelength region.
Claim 20
Dependent Claim
23 words
The composition in accordance with claim 14 wherein the resulting mixed composition, when incorporated into a photoresponsive imaging member, possesses superior cycling characteristics.
Claim 21
Dependent Claim
46 words
An improved process for the preparation of squaraine compositions which comprises reacting squaric acid, an aromatic amine, and a fluoroaniline, of the following formulas, in the presence of an aliphatic alcohol ##STR9## wherein the ratio of x to y is from about 10 to about 0.333.
Claim 22
Dependent Claim
46 words
An improved process for the preparation of squaraine compositions which comprises reacting squaric acid, an aromatic amine, and a fluoroaniline, of the following formulas, in the presence of an aliphatic alcohol ##STR9## wherein the ratio of x to y is from about 10 to about 0.333.
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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) | 1989-08-18 | 1990-02-17 | 1990-08-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-08-18 | 1994-02-17 | 1994-08-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-08-18 | 1998-02-17 | 1998-08-19 | $7700.00 | Window Closed / Lapsed |