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US4524218A
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Processes for the preparation of squaraine compositions
Assignee: Xerox Corp
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Filing: 1984-01-11
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Granted: 1985-06-18
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Expires: 2004-01-11
Abstract
Abstract Disclosed is an improved process for the preparation of squaraine compositions which comprises reacting squaric acid, an aromatic amine, and a composition selected from the group consisting of phenols and phenol squaraines, in the presence of an aliphatic alcohol, and an optional azeotropic substance.
Inventors
- 👤 Giuseppa Baranyi
- 👤 Peter M. Kazmaier
- 👤 Cheng-Kuo Hsiao
- 👤 Richard A. Burt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 06:40
CPC Classifications
C; C09; C09B; C09B57/00; C09B57/007; C07; C07C; C07C213/00; C07C213/08; G; G03; G03G; G03G5/00; G03G5/02; G03G5/04; G03G5/06; G03G5/0601; G03G5/0609; G03G5/0611
Claims Analysis
Total Claims: 28
Claim 1
Independent Claim
42 words
An improved process for the preparation of squaraine compositions which comprises reacting squaric acid, an aromatic amine, and a composition selected from the group consisting of phenols and phenol squaraines, in the presence of an aliphatic alcohol, and an optional azeotropic substance.
Claim 2
Dependent Claim
42 words
An improved process for the preparation of squaraine compositions which comprises reacting squaric acid, an aromatic amine, and a composition selected from the group consisting of phenols and phenol squaraines, in the presence of an aliphatic alcohol, and an optional azeotropic substance.
Claim 3
Dependent Claim
25 words
An improved process in accordance with claim 1 wherein the reaction is accomplished at a temperature of from about 65° C. to about 130° C.
Claim 4
Dependent Claim
12 words
A process in accordance with claim 1 wherein the phenol is orcinol.
Claim 5
Dependent Claim
12 words
A process in accordance with claim 1 wherein the phenol is resorcinol.
Claim 6
Dependent Claim
12 words
A process in accordance with claim 1 wherein the phenol is phloroglucinol.
Claim 7
Dependent Claim
13 words
A process in accordance with claim 1 wherein the phenol squaraine is bis(2,6-dihydroxy-4-methylphenyl)squaraine.
Claim 8
Dependent Claim
22 words
A process in accordance with claim 1 wherein the aliphatic alcohol contains from about 1 carbon atom to about 6 carbon atoms.
Claim 9
Dependent Claim
12 words
A process in accordance with claim 1 wherein the alcohol is butanol.
Claim 10
Dependent Claim
12 words
A process in accordance in claim 1 wherein the alcohol is heptanol.
Claim 11
Dependent Claim
13 words
A process in accordance with claim 1 wherein the amine reactant is 3-dimethylamino-5-methylphenyl.
Claim 12
Dependent Claim
13 words
A process in accordance with claim 1 wherein the amine reactant is N,N-dimethyl-m-toluidine.
Claim 13
Dependent Claim
13 words
A process in accordance with claim 1 wherein there results the product bis(4-dimethylaminophenyl)squaraine.
Claim 14
Dependent Claim
11 words
A process in accordance with claim 1 wherein there results bis(2-fluoro-4-dimethylaminophenyl)squaraine.
Claim 15
Dependent Claim
91 words
A process for the preparation of squaraine compositions which comprises reacting at a temperature of from about 65° C. to about 130° C. squaric acid, an aromatic amine composition I, a phenol II, or a phenol squaraine III, which reaction is effected in the presence of an aliphatic alcohol, and an azeotropic substance, wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are independently selected from aromatic groups, alkyl groups, and halogens, and X is hydrogen, halogen, hydroxy, or carboxy. ##STR2##
Claim 16
Dependent Claim
91 words
A process for the preparation of squaraine compositions which comprises reacting at a temperature of from about 65° C. to about 130° C. squaric acid, an aromatic amine composition I, a phenol II, or a phenol squaraine III, which reaction is effected in the presence of an aliphatic alcohol, and an azeotropic substance, wherein R 1 , R 2 , R 3 , R 4 , R 5 , and R 6 are independently selected from aromatic groups, alkyl groups, and halogens, and X is hydrogen, halogen, hydroxy, or carboxy. ##STR2##
Claim 17
Dependent Claim
12 words
A process in accordance with claim 14 wherein x is a hydroxy.
Claim 18
Dependent Claim
11 words
A process in accordance with claim 14 wherein x is fluorine.
Claim 19
Dependent Claim
13 words
A process in accordance with claim 14 wherein the aliphatic alcohol is 1-butanol.
Claim 20
Dependent Claim
15 words
A process in accordance with claim 14 wherein the azeotropic substance is toluene or benzene.
Claim 21
Dependent Claim
22 words
A process in accordance with claim 14 wherein the alkyl groups contain from about 1 carbon atom to about 6 carbon atoms.
Claim 22
Dependent Claim
13 words
A process in accordance with claim 14 wherein the aromatic group is phenyl.
Claim 23
Dependent Claim
12 words
A process in accordance with claim 14 wherein the phenol is orcinol.
Claim 24
Dependent Claim
12 words
A process in accordance with claim 14 wherein the phenol is resorcinol.
Claim 25
Dependent Claim
12 words
A process in accordance with claim 14 wherein the phenol is phlorglucinol.
Claim 26
Dependent Claim
13 words
A process in accordance with claim 14 wherein the phenol squaraine is bis(2,6-dihydroxy-4-methylphenyl)squaraine.
Claim 27
Dependent Claim
13 words
A process in accordance with claim 14 wherein the squaraine resulting is bis(4-dimethylaminophenyl)squaraine.
Claim 28
Dependent Claim
13 words
A process in accordance with claim 14 wherein the squaraine resulting is bis(2-fluoro-4-dimethylaminophenyl)squaraine.
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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) | 1988-06-17 | 1988-12-17 | 1989-06-18 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-06-17 | 1992-12-17 | 1993-06-18 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-06-17 | 1996-12-17 | 1997-06-18 | $7700.00 | Window Closed / Lapsed |