US4585895A
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Processes for the preparation of mixed squaraine compositions
Assignee: Xerox Corp
•
Filing: 1985-02-20
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Granted: 1986-04-29
•
Expires: 2005-02-20
Abstract
Abstract Disclosed is an improved process for the preparation of mixed squaraine compositions which comprises reacting a dialkyl squarate, a dialkyl aniline, and a dialkylhaloaniline in the presence of an aliphatic alcohol and an acid catalyst.
Inventors
- 👤 Kock-Yee Law
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 16:53
CPC Classifications
G; G03; G03G; G03G5/00; G03G5/02; G03G5/04; G03G5/06; G03G5/0601; G03G5/0609; G03G5/0611
Claims Analysis
Total Claims: 32
Claim 1
Independent Claim
33 words
An improved process for the preparation of mixed squaraine compositions which comprises reacting a dialkyl squarate, a dialkyl aniline, and a dialkylhaloaniline in the presence of an aliphatic alcohol and an acid catalyst.
Claim 2
Dependent Claim
33 words
An improved process for the preparation of mixed squaraine compositions which comprises reacting a dialkyl squarate, a dialkyl aniline, and a dialkylhaloaniline in the presence of an aliphatic alcohol and an acid catalyst.
Claim 3
Dependent Claim
26 words
A process in accordance with claim 1 wherein the reaction is accomplished at a temperature of from about 60 degrees Centigrade to about 160 degrees Centigrade.
Claim 4
Dependent Claim
34 words
A process in accordance with claim 1 wherein the dialkyl squarate is selected from the group consisting of a dimethyl squarate, diethyl squarate, dipropyl squarate, dibutyl squarate, dipentyl squarate, dihexyl squarate and diheptyl squarate.
Claim 5
Dependent Claim
14 words
A process in accordance with claim 1 wherein the dialkyl squarate is dimethyl squarate.
Claim 6
Dependent Claim
21 words
A process in accordance with claim 1 wherein the dialkylhaloaniline is selected from the group consisting of 3-fluoro-N,N-dimethylaniline, 2-fluoro-N,N-dimethylaniline, and 3-chloro-N,N-dimethylaniline.
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
26 words
A process in accordance with claim 1 wherein the resulting mixed squaraine composition is comprised of I, bis(4-dimethylaminophenyl) squaraine, II, 2-fluoro-4-dimethylaminophenyl-4'-dimethylaminophenyl squaraine, and III, bis(2-fluoro-4-dimethylaminophenyl) squaraine.
Claim 9
Dependent Claim
34 words
A process in accordance with claim 7 wherein the mixture contains about 84 mole percent of I, about 15 to 16 mole percent of II, and about 1 to 2 mole percent of III.
Claim 10
Dependent Claim
30 words
A process in accordance with claim 7 wherein the mixture contains about 59 mole percent of I, about 35 mole percent of II, and about 6 mole percent of III.
Claim 11
Dependent Claim
30 words
A process in accordance with claim 7 wherein the mixture contains about 14 mole percent of I, about 42 mole percent of II, and about 44 mole percent of III.
Claim 12
Dependent Claim
23 words
A process in accordance with claim 1 wherein the resulting mixed squaraine composition is comprised of IV, bis(4-dimethylaminophenyl) squaraine, and V, 3-fluoro-4-dimethylaminophenyl-4'-dimethylaminophenyl squaraine.
Claim 13
Dependent Claim
28 words
A process in accordance with claim 11 wherein the mixture contains about 95 to 99 mole percent of IV, and about 1 to 5 mole percent of V.
Claim 14
Dependent Claim
23 words
A process in accordance with claim 1 wherein the resulting mixed squaraine product is comprised of VI, bis(4-dimethylaminophenyl) squaraine, and VII, 2-chloro-4-dimethylaminophenyl-4'-dimethylaminophenyl squaraine.
Claim 15
Dependent Claim
24 words
A process in accordance with claim 13, wherein the mixture contains about 81 mole percent of VI, and about 19 mole percent of VII.
Claim 16
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 17
Dependent Claim
80 words
A process for the preparation of the mixed squaraine compositions ##STR2## which comprises reacting in the presence of an optional acid catalyst and an aliphatic alcohol an alkyl squarate of the following formula with a dialkylaniline, and dialkylhaloaniline of the following formulas: ##STR3## wherein R, R 1 , R 3 , are independently selected from the group consisting of alkyl, and R 2 is independently selected from the group consisting of alkyl, alkoxy, and hydroxy, and x is a halogen.
Claim 18
Dependent Claim
80 words
A process for the preparation of the mixed squaraine compositions ##STR2## which comprises reacting in the presence of an optional acid catalyst and an aliphatic alcohol an alkyl squarate of the following formula with a dialkylaniline, and dialkylhaloaniline of the following formulas: ##STR3## wherein R, R 1 , R 3 , are independently selected from the group consisting of alkyl, and R 2 is independently selected from the group consisting of alkyl, alkoxy, and hydroxy, and x is a halogen.
Claim 19
Dependent Claim
30 words
A process in accordance with claim 16 wherein R, R 1 , and R 3 , are alkyl groups of from about 1 carbon atom to about 10 carbon atoms.
Claim 20
Dependent Claim
12 words
A process in accordance with claim 16 the alkyl substituents are methyl.
Claim 21
Dependent Claim
22 words
A process in accordance with claim 16 wherein R 2 is an alkyl group of from 1 to about 10 carbon atoms.
Claim 22
Dependent Claim
22 words
A process in accordance with claim 16 wherein R 2 is an alkoxy group of from 1 to about 10 carbon atoms.
Claim 23
Dependent Claim
11 words
A process in accordance with claim 16 wherein X is fluorine.
Claim 24
Dependent Claim
11 words
A process in accordance with claim 16 wherein X is chlorine.
Claim 25
Dependent Claim
29 words
A process in accordance with claim 1 wherein the dialkylaniline is selected from the group consisting of a N,N-dimethylaniline, N,N-diethylaniline, N,N-dipropylaniline, N,N-dibutylaniline, N,N-dipentylaniline, 3-fluoro-N,N-dimethylaniline, 3-hydroxy-N,N-dimethylaniline, 3-methyl-N,N-dimethylaniline, 3-hydroxy-N,N-diethylaniline, and 3-methoxy-N,N-dimethylaniline.
Claim 26
Dependent Claim
25 words
A process in accordance with claim 1 wherein the acid catalyst is selected from the group consisting of sulfuric acid, trichloroacetic acid, and oxalic acid.
Claim 27
Dependent Claim
56 words
An improved process for the preparation of a mixture of squaraine compositions consisting essentially of the reaction of a dialkyl squarate, a dialkyl aniline, and a dialkylhaloaniline in the presence of an aliphatic alcohol and an acid catalyst, which reaction is accomplished at a temperature of from about 60 degrees Centigrade to about 160 degrees Centigrade.
Claim 28
Dependent Claim
56 words
An improved process for the preparation of a mixture of squaraine compositions consisting essentially of the reaction of a dialkyl squarate, a dialkyl aniline, and a dialkylhaloaniline in the presence of an aliphatic alcohol and an acid catalyst, which reaction is accomplished at a temperature of from about 60 degrees Centigrade to about 160 degrees Centigrade.
Claim 29
Dependent Claim
33 words
A process in accordance with claim 25 wherein the dialkyl squarate is selected from the group consisting of dimethyl squarate, diethyl squarate, dipropyl squarate, dibutyl squarate, dipentyl squarate, dihexyl squarate and diheptyl squarate.
Claim 30
Dependent Claim
26 words
A process in accordance with claim 25 wherein the resulting mixed squaraine composition is comprised of I, bis(4-dimethylaminophenyl) squaraine; II, 2-fluoro-4-dimethylaminophenyl-4'-dimethylaminophenyl squaraine; and III, bis(2-fluoro-4-dimethylaminophenyl) squaraine.
Claim 31
Dependent Claim
21 words
A process in accordance with claim 25 wherein the dialkylhaloaniline is selected from the group consisting of 3-fluoro-N,N-dimethylaniline, 2-fluoro-N,N-dimethylaniline, and 3-chloro-N,N-dimethylaniline.
Claim 32
Dependent Claim
29 words
A process in accordance with claim 25 wherein the dialkylaniline is selected from the group consisting of a N,N-dimethylaniline, N,N-diethylaniline, N,N-dipropylaniline, N,N-dibutylaniline, N,N-dipentylaniline, 3-fluoro-N,N-dimethylaniline, 3-hydroxy-N,N-dimethylaniline, 3-methyl-N,N-dimethylaniline, 3-hydroxy-N,N-diethylaniline, and 3-methoxy-N,N-dimethylaniline.
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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) | 1989-04-28 | 1989-10-28 | 1990-04-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-04-28 | 1993-10-28 | 1994-04-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-04-28 | 1997-10-28 | 1998-04-29 | $7700.00 | Window Closed / Lapsed |