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US4228070A
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Purification of photographic image-forming sulfonamido compounds employing immiscible solvents
Assignee: Eastman Kodak Co
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Filing: 1979-02-28
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Granted: 1980-10-14
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Expires: 1999-02-28
Abstract
Abstract A process for purifying a photographic image-forming sulfonamido compound comprises the steps of: a. preparing a first solution by dissolving an unpurified image-forming sulfonamido compound in an aprotic solvent; b. removing impurities from said first solution by, at least once: i. mixing said first solution with an immiscible nonpolar, low-boiling organic solvent to form a mixture of said first solution and a second solution comprising said immiscible nonpolar, low-boiling organic solvent and at least a portion of said impurities; and ii. separating said first solution from said second solution; and c. recovering purified image-forming sulfonamido compound from said first solution. The process is useful in the purification of a nondiffusible sulfonamido compound which is alkali-cleavable upon oxidation to release a diffusible sulfonamido color-providing moiety.
Inventors
- 👤 Nigel E. Milner
- 👤 Christine C. Payne
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 19:08
CPC Classifications
G; G03; G03C; G03C8/00; G03C8/02; G03C8/08; G03C8/10; C; C09; C09B; C09B29/00; C09B29/24; C09B29/28
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
102 words
A process for purifying a photographic image-forming sulfonamido compound, said process comprising the steps of: a. preparing a first solution by dissolving an unpurified image-forming sulfonamido compound in an aprotic solvent; b. removing impurities from said first solution by, at least once: i. mixing said first solution with an immiscible nonpolar, low-boiling organic solvent to form a mixture of said first solution and a second solution comprising said immiscible nonpolar, low-boiling organic solvent and at least a portion of said impurities; and ii. separating said first solution from said second solution; and c. recovering purified image-forming sulfonamido compound from said first solution.
Claim 2
Dependent Claim
102 words
A process for purifying a photographic image-forming sulfonamido compound, said process comprising the steps of: a. preparing a first solution by dissolving an unpurified image-forming sulfonamido compound in an aprotic solvent; b. removing impurities from said first solution by, at least once: i. mixing said first solution with an immiscible nonpolar, low-boiling organic solvent to form a mixture of said first solution and a second solution comprising said immiscible nonpolar, low-boiling organic solvent and at least a portion of said impurities; and ii. separating said first solution from said second solution; and c. recovering purified image-forming sulfonamido compound from said first solution.
Claim 3
Dependent Claim
37 words
The process of claim 1 wherein recovery of said purified image-forming sulfonamido compound is effected by: a. evaporating said first solution to remove nonpolar, low-boiling solvent contamination; and b. precipitating said image-forming sulfonamido compound in a nonsolvent.
Claim 4
Dependent Claim
117 words
The process of claim 1 wherein recovery of said purified image-forming sulfonamido compound is effected by: a. preparing a third solution by adding to (b)(i) a water-immiscible low-boiling solvent of intermediate polarity to said first solution; b. removing said aprotic solvent from said third solution by at least once: i. mixing said third solution with water to form a mixture of said third solution and a fourth solution comprising water and at least a portion of said aprotic solvent; and ii. separating said third solution from said fourth solution; and c. evaporating at least a portion of said water-immiscible low-boiling solvent of intermediate polarity from said third solution to effect crystallization of said purified image-forming sulfonamido compound.
Claim 5
Dependent Claim
29 words
The process of claim 1 wherein said aprotic organic solvent is N,N,-dimethylformamide and said immiscible nonpolar, low-boiling solvent is a petroleum hydrocarbon having a boiling range of 60°-80° C.
Claim 6
Dependent Claim
18 words
The process of claim 4 wherein said petroleum hydrocarbon is ligroin having a boiling range of 60°-80° C.
Claim 7
Dependent Claim
21 words
The process of claim 2 wherein said nonsolvent comprises water, an aqueous dilute acid solution, or an alcoholic dilute acid solution.
Claim 8
Dependent Claim
16 words
The process of claim 6 wherein said alcoholic dilute acid solution comprises methanol or isopropyl alcohol.
Claim 9
Dependent Claim
17 words
The process of claim 6 wherein said aqueous dilute acid solution comprises hydrochloric acid or acetic acid.
Claim 10
Dependent Claim
16 words
The process of claim 3 wherein said water-immiscible, low-boiling solvent of intermediate polarity is ethyl acetate.
Claim 11
Dependent Claim
108 words
The process of claim 1 wherein said image-forming sulfonamido compound is a nondiffusible sulfonamido compound which is alkali-cleavable upon oxidation to release a diffusible sulfonamido color-providing moiety, said sulfonamido compound having the formula: ##STR10## wherein: Col is a dye or dye precursor moiety; Ball is an organic ballasting group which renders said compound nondiffusible in a photographic element during development in an alkaline processing composition; Y represents the atoms necessary to complete a benzene, naphthalene or heterocyclic nucleus; and G is OR or NHR 1 wherein R is hydrogen or a hydrolyzable moiety and R 1 is hydrogen or an alkyl group of 1 to 22 carbon atoms.
Claim 12
Dependent Claim
12 words
The process of claim 10 wherein said sulfonamido compound is a sulfonamidonaphthol.
Claim 13
Dependent Claim
36 words
The process of claim 10 wherein recovery of said nondiffusible sulfonamido compound is effected by: a. evaporating said first solution to remove nonpolar, low-boiling solvent contamination; and b. precipitating said image-forming sulfonamido compound in a nonsolvent.
Claim 14
Dependent Claim
114 words
The process of claim 10 wherein recovery of said nondiffusible sulfonamido compound is effected by: a. preparing a third solution by adding a water-immiscible low-boiling solvent of intermediate polarity to said first solution; b. removing said aprotic solvent from said third solution by at least once: i. mixing said third solution with water to form a mixture of said third solution and a fourth solution comprising water and at least a portion of said aprotic solvent; and ii. separating said third solution from said fourth solution; and c. evaporating at least a portion of said water-immiscible low-boiling solvent of intermediate polarity from said third solution to effect crystallization of said purified image-forming sulfonamido compound.
Claim 15
Dependent Claim
22 words
The process of claim 10 wherein said aprotic organic solvent is N,N-dimethylformamide and said immiscible nonpolar, low-boiling solvent is a petroleum hydrocarbon.
Claim 16
Dependent Claim
117 words
A process for purifying a photographic image-forming sulfonamido compound, said process comprising the steps of: a. preparing a first solution by dissolving an unpurified image-forming sulfonamido compound in N,N-dimethylformamide; b. removing impurities from said first solution by at least once: i. mixing said first solution with ligroin having a boiling range of 60°-80° C. to form a mixture of said first solution and a second solution comprising said ligroin and at least a portion of said impurities; ii. separating said first solution from said second solution; and c. recovering purified imageforming sulfonamido compound from said first solution by: i. evaporating said first solution to remove ligroin contamination; and ii. precipitating said image-forming sulfonamido compound in a nonsolvent.
Claim 17
Dependent Claim
117 words
A process for purifying a photographic image-forming sulfonamido compound, said process comprising the steps of: a. preparing a first solution by dissolving an unpurified image-forming sulfonamido compound in N,N-dimethylformamide; b. removing impurities from said first solution by at least once: i. mixing said first solution with ligroin having a boiling range of 60°-80° C. to form a mixture of said first solution and a second solution comprising said ligroin and at least a portion of said impurities; ii. separating said first solution from said second solution; and c. recovering purified imageforming sulfonamido compound from said first solution by: i. evaporating said first solution to remove ligroin contamination; and ii. precipitating said image-forming sulfonamido compound in a nonsolvent.
Claim 18
Dependent Claim
27 words
The process of claim 15 wherein said non-solvent is a dilute solution of hydrochloric acid in methanol or a dilute solution or acetic acid in isopropyl alcohol.
Claim 19
Dependent Claim
108 words
The process of claim 15 wherein said image-forming sulfonamido compound is a nondiffusible sulfonamido compound which is alkali-cleavable upon oxidation to release a diffusible sulfonamido color-providing moiety, said sulfonamido compound having the formula: ##STR11## wherein: Col is a dye or dye precursor moiety; Ball is an organic ballasting group which renders said compound nondiffusible in a photographic element during development in an alkaline processing composition; Y represents the atoms necessary to complete a benzene, naphthalene or heterocyclic nucleus; and G is OR or NHR 1 wherein R is hydrogen or a hydrolyzable moiety and R 1 is hydrogen or an alkyl group of 1 to 22 carbon atoms.
Claim 20
Dependent Claim
11 words
The process of claim 15 wherein said sulfonamido compound is sulfonamidonaphthol.
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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) | 1983-10-14 | 1984-04-14 | 1984-10-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-10-14 | 1988-04-14 | 1988-10-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-10-14 | 1992-04-14 | 1992-10-14 | $7700.00 | Window Closed / Lapsed |