US4525592A
Expired / Lapsed
US
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Process for squaraine compositions
Assignee: Xerox Corp
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Filing: 1983-12-05
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Granted: 1985-06-25
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Expires: 2003-12-05
Abstract
Abstract This invention relates to an improved process for the preparation of squaraine compositions which comprises reacting a dialkyl squarate, with an aniline, in the presence of an acid and an aliphatic alcohol, at a temperature of from about 60 degrees Centigrade to 160 degrees Centigrade.
Inventors
- 👤 Kock-Yee Law
- 👤 Frank C. Bailey
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 12:41
CPC Classifications
G; G03; G03G; G03G5/00; G03G5/02; G03G5/04; G03G5/06; G03G5/0601; G03G5/0605; G03G5/0607; C; C09; C09B; C09B57/00; C09B57/007; G03G5/0618
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
43 words
An improved process for the preparation of squaraine compositions which comprises reacting a dialkyl squarate, with an aniline, in the presence of an acid catalyst and an aliphatic alcohol, at a temperature of from about 60 degrees Centigrade to about 160 degrees Centigrade.
Claim 2
Dependent Claim
43 words
An improved process for the preparation of squaraine compositions which comprises reacting a dialkyl squarate, with an aniline, in the presence of an acid catalyst and an aliphatic alcohol, at a temperature of from about 60 degrees Centigrade to about 160 degrees Centigrade.
Claim 3
Dependent Claim
25 words
A process in accordance with claim 1 wherein the dialkyl squarate is dimethyl squarate, diethyl squarate, dipropyl squarate, dibutyl squarate, dipentyl squarate, or diheptyl squarate.
Claim 4
Dependent Claim
17 words
A process in accordance with claim 1 wherein the aniline is N,N-dimethyaniline, N,N-diethylaniline, N,N-dipropylaniline, N,N-dibutylaniline, or N,N-dipentylaniline.
Claim 5
Dependent Claim
16 words
A process in accordance with claim 1 wherein the aniline is 3-fluoro-N,N-dimethylaniline, 3-hydroxy-N,N-dimethylaniline, or 3-methyl-N,N-dimethylaniline, 3-hydroxy-N,N-diethylaniline.
Claim 6
Dependent Claim
19 words
A process in accordance with claim 1 wherein the acid catalyst is sulfuric acid, trichloroacetic acid or oxalic acid.
Claim 7
Dependent Claim
17 words
A process in accordance with claim 1 wherein the aliphatic alcohol is 1-butanol, 1-propanol, or amyl alcohol.
Claim 8
Dependent Claim
54 words
A process in accordance with claim 1 wherein there is selected from about 5 millimoles to about 50 millimoles of dialkyl squarate, from about 0.1 milliliters to about 1 milliliters of acid, from about 10 millimoles to about 100 millimoles of aniline, and from about 5 milliliters to about 50 milliliters of aliphatic alcohol.
Claim 9
Dependent Claim
22 words
A process in accordance with claim 1 wherein the reaction temperature is from about 98 degrees Centigrade to about 140 degrees Centigrade.
Claim 10
Dependent Claim
14 words
A process in accordance with claim 1 wherein the resulting squaraine product is bis(2-fluoro-4-dimethylaminophenyl)squaraine.
Claim 11
Dependent Claim
14 words
A process in accordance with claim 1 wherein the resulting squaraine product is bis(4-dimethylaminophenyl)squaraine.
Claim 12
Dependent Claim
14 words
A process in accordance with claim 1 wherein the resulting squaraine product is bis(2-hydroxy-4-dimethylaminophenyl)squaraine.
Claim 13
Dependent Claim
16 words
A process in accordance with claim 1 wherein the resulting squaraine product is bis(2-methyl-4-dimethylaminophenyl)squaraine, or bis(2-hydroxy-4-diethylaminophenyl)squaraine.
Claim 14
Dependent Claim
14 words
A process in accordance with claim 1 wherein the dialkyl squarate is di-n-butyl squarate.
Claim 15
Dependent Claim
90 words
A process for the preparation of squaraine compositions which comprises reacting at a temperature of from about 60 degrees Centigrade to about 160 degrees Centigrade in the presence of an acid catalyst and an aliphatic alcohol a dialkyl squarate of the following formula with an aniline of the following formula: ##STR2## wherein R, R 1 , R 2 , are independently selected from alkyl groups, and R 3 is an alkyl group, a hydroxy group, or fluorine, Ar is an aromatic group, and n is the number zero or one.
Claim 16
Dependent Claim
90 words
A process for the preparation of squaraine compositions which comprises reacting at a temperature of from about 60 degrees Centigrade to about 160 degrees Centigrade in the presence of an acid catalyst and an aliphatic alcohol a dialkyl squarate of the following formula with an aniline of the following formula: ##STR2## wherein R, R 1 , R 2 , are independently selected from alkyl groups, and R 3 is an alkyl group, a hydroxy group, or fluorine, Ar is an aromatic group, and n is the number zero or one.
Claim 17
Dependent Claim
33 words
A process in accordance with claim 14, wherein R, R 1 , R 2 , and R 3 , are alkyl groups containing from about one carbon atom to about ten carbon atoms.
Claim 18
Dependent Claim
26 words
A process in accordance with claim 14, wherein R is butyl, Ar is phenyl, R 1 is methyl, R 2 is methyl, and n is zero.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-06-24 | 1988-12-24 | 1989-06-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-06-24 | 1992-12-24 | 1993-06-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-06-24 | 1996-12-24 | 1997-06-25 | $7700.00 | Window Closed / Lapsed |