US5166339A
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Processes for the preparation of titanium phthalocyanines
Assignee: Xerox Corp
•
Filing: 1990-06-04
•
Granted: 1992-11-24
•
Expires: 2010-06-04
Abstract
Abstract Disclosed are various titanyl phthalocyanine polymorphs such as Type I, Type II, Type III, Type IV, Type Z-1, Type Z-2, and Type X, which phthalocyanines can be prepared by dissolving a titanyl phthalocyanine in a solution of trifluoroacetic acid and a chlorinated hydrocarbon. There is then added to the resulting solution a solvent that will enable precipitation of the titanyl phthalocyanine. Subsequently, the titanyl phthalocyanine product can be separated from the solution by, for example, filtration and the product titanyl phthalocyanine obtained can be washed to remove any residual solvent.
Inventors
- 👤 James M. Duff
- 👤 James D. Mayo
- 👤 Cheng-Kuo Hsiao
- 👤 Ah-Mee Hor
- 👤 Terry L. Bluhm
- 👤 Gordon K. Hamer
- 👤 Peter M. Kazmaier
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 01:45
CPC Classifications
C; C09; C09B; C09B47/00; C09B47/04; C09B47/06; C09B47/073; C09B67/00; C09B67/0001; C09B67/0014; C09B67/0016; C09B67/0025; C09B67/0026; G; G11; G11B; G11B7/00; G11B7/24; G11B7/241; G11B7/242; G11B7/244; G11B7/246; G11B7/248
Claims Analysis
Total Claims: 62
Claim 1
Independent Claim
68 words
A process for the preparation of titanyl phthalocyanine Type I, Type II, Type III, Type IV, Type X, Type Z-1, and Type Z-2, which consists essentially of dissolving a titanyl phthalocyanine in a solution of trifluoroacetic acid and methylene chloride; adding the resultant solution to a solvent or solvent mixture that will enable precipitation; and separating the product titanyl phthalocyanine from the solution followed by an optional washing.
Claim 2
Dependent Claim
68 words
A process for the preparation of titanyl phthalocyanine Type I, Type II, Type III, Type IV, Type X, Type Z-1, and Type Z-2, which consists essentially of dissolving a titanyl phthalocyanine in a solution of trifluoroacetic acid and methylene chloride; adding the resultant solution to a solvent or solvent mixture that will enable precipitation; and separating the product titanyl phthalocyanine from the solution followed by an optional washing.
Claim 3
Dependent Claim
68 words
A process for the preparation of titanyl phthalocyanine Type I, Type II, Type III, Type IV, Type X, Type Z-1, and Type Z-2, which consists essentially of adding a titanyl phthalocyanine to a solution of trifluoroacetic acid and methylene chloride; adding the resultant solution to a solvent or solvent mixture that will enable precipitation; and separating the product titanyl phthalocyanine from the solution followed by an optional washing.
Claim 4
Dependent Claim
68 words
A process for the preparation of titanyl phthalocyanine Type I, Type II, Type III, Type IV, Type X, Type Z-1, and Type Z-2, which consists essentially of adding a titanyl phthalocyanine to a solution of trifluoroacetic acid and methylene chloride; adding the resultant solution to a solvent or solvent mixture that will enable precipitation; and separating the product titanyl phthalocyanine from the solution followed by an optional washing.
Claim 5
Dependent Claim
17 words
A process in accordance with claim 1 wherein the product titanyl phthalocyanine is a Type IV polymorph.
Claim 6
Dependent Claim
17 words
A process in accordance with claim 2 wherein the product titanyl phthalocyanine is a Type IV polymorph.
Claim 7
Dependent Claim
17 words
A process in accordance with claim 1 wherein the product titanyl phthalocyanine is a Type III polymorph.
Claim 8
Dependent Claim
17 words
A process in accordance with claim 2 wherein the product titanyl phthalocyanine is a Type III polymorph.
Claim 9
Dependent Claim
17 words
A process in accordance with claim 1 wherein the product titanyl phthalocyanine is a Type II polymorph.
Claim 10
Dependent Claim
17 words
A process in accordance with claim 2 wherein the product titanyl phthalocyanine is a Type II polymorph.
Claim 11
Dependent Claim
17 words
A process in accordance with claim 1 wherein the product titanyl phthalocyanine is a Type I polymorph.
Claim 12
Dependent Claim
17 words
A process in accordance with claim 2 wherein the product titanyl phthalocyanine is a Type I polymorph.
Claim 13
Dependent Claim
17 words
A process in accordance with claim 1 wherein the product titanyl phthalocyanine is a Type Z-1 polymorph.
Claim 14
Dependent Claim
17 words
A process in accordance with claim 2 wherein the product titanyl phthalocyanine is a Type Z-1 polymorph.
Claim 15
Dependent Claim
17 words
A process in accordance with claim 1 wherein the product titanyl phthalocyanine is a Type Z-2 polymorph.
Claim 16
Dependent Claim
17 words
A process in accordance with claim 2 wherein the product titanyl phthalocyanine is a Type Z-2 polymorph.
Claim 17
Dependent Claim
17 words
A process in accordance with claim 1 wherein the product titanyl phthalocyanine is a Type X polymorph.
Claim 18
Dependent Claim
17 words
A process in accordance with claim 2 wherein the product titanyl phthalocyanine is a Type X polymorph.
Claim 19
Dependent Claim
60 words
A process for the preparation of titanyl phthalocyanine Type IV which consists essentially of dissolving titanyl phthalocyanine Type I in a solution of trifluoroacetic acid and methylene chloride; adding the solution to a stirred mixture of an alcohol and water whereby a precipitate results; and separating the product titanyl phthalocyanine Type IV from the solution followed by an optional washing.
Claim 20
Dependent Claim
60 words
A process for the preparation of titanyl phthalocyanine Type IV which consists essentially of dissolving titanyl phthalocyanine Type I in a solution of trifluoroacetic acid and methylene chloride; adding the solution to a stirred mixture of an alcohol and water whereby a precipitate results; and separating the product titanyl phthalocyanine Type IV from the solution followed by an optional washing.
Claim 21
Dependent Claim
69 words
A process for the preparation of titanyl phthalocyanine Type I, Type II, Type III, Type IV, Type X, Type Z-1, and Type Z-2, which consists essentially of adding a titanyl phthalocyanine to a solution of trihaloacetic acid and a halogenated hydrocarbon; adding the resultant solution to a solvent or solvent mixture that will enable precipitation; and separating the product titanyl phthalocyanine from the solution followed by an optional washing.
Claim 22
Dependent Claim
69 words
A process for the preparation of titanyl phthalocyanine Type I, Type II, Type III, Type IV, Type X, Type Z-1, and Type Z-2, which consists essentially of adding a titanyl phthalocyanine to a solution of trihaloacetic acid and a halogenated hydrocarbon; adding the resultant solution to a solvent or solvent mixture that will enable precipitation; and separating the product titanyl phthalocyanine from the solution followed by an optional washing.
Claim 23
Dependent Claim
22 words
A process in accordance with claim 17 wherein the titanyl phthalocyanine is dissolved in a mixture of trifluoroacetic acid and methylene chloride.
Claim 24
Dependent Claim
22 words
A process in accordance with claim 18 wherein the titanyl phthalocyanine is dissolved in a mixture of trifluoroacetic acid and methylene chloride.
Claim 25
Dependent Claim
22 words
A process in accordance with claim 17 wherein the titanyl phthalocyanine is dissolved in a mixture of trichloroacetic acid and methylene chloride.
Claim 26
Dependent Claim
22 words
A process in accordance with claim 18 wherein the titanyl phthalocyanine is dissolved in a mixture of trichloroacetic acid and methylene chloride.
Claim 27
Dependent Claim
23 words
A process in accordance with claim 1 wherein the titanyl phthalocyanine is dissolved in a 1:4 mixture of trifluoroacetic acid and methylene chloride.
Claim 28
Dependent Claim
23 words
A process in accordance with claim 2 wherein the titanyl phthalocyanine is dissolved in a 1:4 mixture of trifluoroacetic acid and methylene chloride.
Claim 29
Dependent Claim
17 words
A process in accordance with claim 18 wherein the solvent or solvent mixture is water and methanol.
Claim 30
Dependent Claim
24 words
A process in accordance with claim 18 wherein the solvent or solvent mixture is water and methanol in a ratio of 1:1 by volume.
Claim 31
Dependent Claim
27 words
A process in accordance with claim 18 wherein the solvent or solvent is a mixture of water and methanol containing from 65 percent to 35 percent methanol.
Claim 32
Dependent Claim
12 words
A process in accordance with claim 18 wherein the solvent is water.
Claim 33
Dependent Claim
12 words
A process in accordance with claim 18 wherein the solvent is methanol.
Claim 34
Dependent Claim
17 words
A process in accordance with claim 18 wherein the solvent or solvent mixture is water and ethanol.
Claim 35
Dependent Claim
13 words
A process in accordance with claim 18 wherein the solvent is diethyl ether.
Claim 36
Dependent Claim
13 words
A process in accordance with claim 18 wherein the solvent is isopropyl alcohol.
Claim 37
Dependent Claim
20 words
A process in accordance with claim 18 wherein the solvent or solvent is a mixture of water and ethylene glycol.
Claim 38
Dependent Claim
13 words
A process in accordance with claim 18 wherein separation is accomplished by filtration.
Claim 39
Dependent Claim
35 words
A process in accordance with claim 18 wherein the solvent or solvent mixture is comprised of a mixture of water and a polar aprotic solvent selected from the group dimethyl sulfoxide, dimethyl formamide and N-methylpyrrolidone.
Claim 40
Dependent Claim
19 words
A process in accordance with claim 1 wherein washing is accomplished with a mixture of water and an alcohol.
Claim 41
Dependent Claim
19 words
A process in accordance with claim 2 wherein washing is accomplished with a mixture of water and an alcohol.
Claim 42
Dependent Claim
27 words
A process in accordance with claim 2 wherein washing is accomplished with water and an aromatic solvent selected from the group consisting of benzene, toluene or chlorobenzene.
Claim 43
Dependent Claim
16 words
A process in accordance with claim 2 wherein the product titanyl phthalocyanine is dried by heating.
Claim 44
Dependent Claim
28 words
A process in accordance with claim 2 wherein the product titanyl phthalocyanine is dried by heating at a temperature of from about 70° C. to about 150° C.
Claim 45
Dependent Claim
39 words
A process in accordance with claim 2 wherein the product titanyl phthalocyanine is dried by heating at a temperature of from about 70° C. to about 150° C. for a period of from about 1 to about 15 hours.
Claim 46
Dependent Claim
59 words
A process for the preparation of titanyl phthalocyanine Type IV which consists essentially of dissolving a titanyl phthalocyanine Type I, Type II, Type III, Type IV, or Type X in a solution of trifluoroacetic acid and methylene chloride; adding the solution to a stirred mixture of an alcohol and water whereby a precipitate results; and recovering said titanyl phthalocyanine.
Claim 47
Dependent Claim
59 words
A process for the preparation of titanyl phthalocyanine Type IV which consists essentially of dissolving a titanyl phthalocyanine Type I, Type II, Type III, Type IV, or Type X in a solution of trifluoroacetic acid and methylene chloride; adding the solution to a stirred mixture of an alcohol and water whereby a precipitate results; and recovering said titanyl phthalocyanine.
Claim 48
Dependent Claim
60 words
A process for the preparation of titanyl phthalocyanine Type I, Type II, Type III, Type IV, Type X, Type Z-1, and Type Z-2, which consists essentially of adding a titanyl phthalocyanine to a solution of trifluoroacetic acid and a chlorinated hydrocarbon; adding the resultant solution to a solvent or solvent mixture that will enable precipitation; and recovering said titanyl phthalocyanine.
Claim 49
Dependent Claim
60 words
A process for the preparation of titanyl phthalocyanine Type I, Type II, Type III, Type IV, Type X, Type Z-1, and Type Z-2, which consists essentially of adding a titanyl phthalocyanine to a solution of trifluoroacetic acid and a chlorinated hydrocarbon; adding the resultant solution to a solvent or solvent mixture that will enable precipitation; and recovering said titanyl phthalocyanine.
Claim 50
Dependent Claim
15 words
A process in accordance with claim 42 wherein washing of the titanyl phthalocyanine is accomplished.
Claim 51
Dependent Claim
20 words
A process in accordance with claim 44 wherein washing of the titanyl phthalocyanine is accomplished with water and organic solvents.
Claim 52
Dependent Claim
19 words
A process in accordance with claim 42 wherein there results the titanyl phthalocyanines Type I, II, III, or IV.
Claim 53
Dependent Claim
15 words
A process in accordance with claim 42 wherein there results the titanyl phthalocyanine Type X.
Claim 54
Dependent Claim
15 words
A process in accordance with claim 42 wherein there results the titanyl phthalocyanine Type Z-1.
Claim 55
Dependent Claim
15 words
A process in accordance with claim 42 wherein there results the titanyl phthalocyanine Type Z-2.
Claim 56
Dependent Claim
13 words
A process in accordance with claim 42 wherein recovery is accomplished by filtration.
Claim 57
Dependent Claim
13 words
A process in accordance with claim 43 wherein recovery is accomplished by filtration.
Claim 58
Dependent Claim
63 words
A process for the preparation of titanyl phthalocyanine which consists essentially of dissolving a titanyl phthalocyanine Type I, Type II, Type III, or Type IV in a solution of trifluoroacetic acid and methylene chloride; adding the solution to a stirred solvent or solvent mixture whereby a precipitate of titanyl phthalocyanine of Types I, II, III, or IV results; and recovering said titanyl phthalocyanine.
Claim 59
Dependent Claim
63 words
A process for the preparation of titanyl phthalocyanine which consists essentially of dissolving a titanyl phthalocyanine Type I, Type II, Type III, or Type IV in a solution of trifluoroacetic acid and methylene chloride; adding the solution to a stirred solvent or solvent mixture whereby a precipitate of titanyl phthalocyanine of Types I, II, III, or IV results; and recovering said titanyl phthalocyanine.
Claim 60
Dependent Claim
60 words
A process for the preparation of titanyl phthalocyanine which consists essentially of dissolving a titanyl phthalocyanine Type X, Type Z-1, or Type Z-2 in a solution of trifluoroacetic acid and methylene chloride; adding the solution to a stirred solvent or solvent mixture whereby a precipitate of titanyl phthalocyanine of Types X, Z-1, or Z-2 results; and recovering said titanyl phthalocyanine.
Claim 61
Dependent Claim
60 words
A process for the preparation of titanyl phthalocyanine which consists essentially of dissolving a titanyl phthalocyanine Type X, Type Z-1, or Type Z-2 in a solution of trifluoroacetic acid and methylene chloride; adding the solution to a stirred solvent or solvent mixture whereby a precipitate of titanyl phthalocyanine of Types X, Z-1, or Z-2 results; and recovering said titanyl phthalocyanine.
Claim 62
Dependent Claim
27 words
A process in accordance with claim 45 wherein washing of the titanyl phthalocyanine is accomplished with alcohols, carbonyl compounds, ethers, esters, aromatic compounds and polar aprotic solvents.
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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) | 1995-11-24 | 1996-05-25 | 1996-11-24 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1999-11-24 | 2000-05-25 | 2000-11-24 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2003-11-24 | 2004-05-25 | 2004-11-24 | $7700.00 | Window Closed / Lapsed |