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US4283472A
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Silver halide elements containing blocked pyrazolone magenta dye-forming couplers
Assignee: Eastman Kodak Co
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Filing: 1980-02-26
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Granted: 1981-08-11
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Expires: 2000-02-26
Abstract
Abstract Novel 5-pyrazolone magenta dye-forming couplers are blocked with a coupler moiety which yields an alkali-soluble or colorless reaction product. The coupler moiety is joined via its coupling position to the enol oxygen of the 5-pyrazolone and is displaced therefrom during processing as a result of reaction by means of oxidized color developing agent to thereby activate the 5-pyrazolone coupler. These couplers have good reactivity and good resistance to aerial contaminants, such a formaldehyde, and can be incorporated in photographic emulsions and elements.
Inventors
- 👤 Thomas E. Gompf
- 👤 Howell A. Hammond
- 👤 Jared B. Mooberry
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 15:21
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/02; C07D231/10; C07D231/14; C07D231/44; C07D231/52; G; G03; G03C; G03C7/00; G03C7/30; G03C7/32; G03C7/36; G03C7/38; G03C7/384
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
108 words
A photographic element comprising a support and a photosensitive silver halide emulsion having associated therewith a nondiffusible magenta dye-forming coupler having the structure: ##STR22## wherein: Q represents the atoms to complete a 5-pyrazolone magenta dye-forming coupler moiety; n is 1 or 2; R is a ballast group when n is 1 or a divalent organic group when n is 2; R 1 is hydrogen or a coupling-off group; and Cp is a coupler moiety which upon reaction by means of oxidized color developing agent yields a colorless or alkali soluble reaction product and is attached at its coupling position to the enol oxygen of the pyrazolone coupler moiety.
Claim 2
Dependent Claim
108 words
A photographic element comprising a support and a photosensitive silver halide emulsion having associated therewith a nondiffusible magenta dye-forming coupler having the structure: ##STR22## wherein: Q represents the atoms to complete a 5-pyrazolone magenta dye-forming coupler moiety; n is 1 or 2; R is a ballast group when n is 1 or a divalent organic group when n is 2; R 1 is hydrogen or a coupling-off group; and Cp is a coupler moiety which upon reaction by means of oxidized color developing agent yields a colorless or alkali soluble reaction product and is attached at its coupling position to the enol oxygen of the pyrazolone coupler moiety.
Claim 3
Dependent Claim
77 words
A photographic element of claim 1 wherein the magneta dye-forming coupler has the structure: ##STR23## wherein: Q represents the atoms to complete a 5-pyrazolone magenta dye-forming coupler moiety; n is 1 or 2; R is a ballast group when n is 1 or a divalent organic group when n is 2; R 1 is hydrogen or a coupling-off group and R 2 and R 3 represent the atoms to complete an alkali soluble yellow dye-forming coupler moiety.
Claim 4
Dependent Claim
63 words
A photographic element of claim 1 wherein the magenta dye-forming coupler has the structure: ##STR24## wherein: n is 1 or 2; R 4 is hydrogen or a coupling-off group; R 5 is a monovalent or divalent amino or amido ballast group or an alkylene or arylene group; R 6 is aryl; and R 7 is one or more acid or ester solubilizing groups.
Claim 5
Dependent Claim
35 words
A photographic element of claim 3 wherein: n is 1; R 4 is hydrogen, aryloxy or arylthio; R 5 is a monovalent amino or amido ballast group; and R 6 is phenyl, alkoxyphenyl or halophenyl.
Claim 6
Dependent Claim
18 words
A photographic element of claim 1 wherein the magenta dye-forming coupler has one of the following structures: ##STR25##
Claim 7
Dependent Claim
99 words
A photographic silver halide emulsion containing a nondiffusible magenta dye-forming coupler having the structure: ##STR26## wherein: Q represents the atoms to complete a 5-pyrazolone magenta dye-forming coupler moiety; n is 1 or 2; R is a ballast group when n is 1 or a divalent organic group when n is 2; R 1 is hydrogen or a coupling-off group; and Cp is a coupler moiety which upon reaction by means of oxidized color developing agent yields a colorless or alkali soluble reaction product and is attached at its coupling position to the enol oxygen of the pyrazolone coupler moiety.
Claim 8
Dependent Claim
99 words
A photographic silver halide emulsion containing a nondiffusible magenta dye-forming coupler having the structure: ##STR26## wherein: Q represents the atoms to complete a 5-pyrazolone magenta dye-forming coupler moiety; n is 1 or 2; R is a ballast group when n is 1 or a divalent organic group when n is 2; R 1 is hydrogen or a coupling-off group; and Cp is a coupler moiety which upon reaction by means of oxidized color developing agent yields a colorless or alkali soluble reaction product and is attached at its coupling position to the enol oxygen of the pyrazolone coupler moiety.
Claim 9
Dependent Claim
77 words
A photographic emulsion of claim 5 wherein the magenta dye-forming coupler has the structure: ##STR27## wherein: Q represents the atoms to complete a 5-pyrazolone magenta dye-forming coupler moiety; n is 1 or 2; R is a ballast group when n is 1 or a divalent organic group when n is 2; R 1 is hydrogen or a coupling-off group and R 2 and R 3 represent the atoms to complete an alkali soluble yellow dye-forming coupler moiety.
Claim 10
Dependent Claim
63 words
A photographic emulsion of claim 5 wherein the magenta dye-forming coupler has the structure: ##STR28## wherein: n is 1 or 2; R 4 is hydrogen or a coupling-off group; R 5 is a monovalent or divalent amino or amido ballast group or an alkylene or arylene group; R 6 is aryl; and R 7 is one or more acid or ester solubilizing groups.
Claim 11
Dependent Claim
35 words
A photographic emulsion of claim 7 wherein n is 1; R 4 is hydrogen, aryloxy or arylthio; R 5 is a monovalent amino or amido ballast group and R 6 is phenyl, alkoxyphenyl or halophenyl.
Claim 12
Dependent Claim
131 words
A process of forming a magenta dye image in a photographic element comprising a support and a silver halide emulsion, comprising the step of developing the element with a silver halide color developing agent in the presence of a nondiffusible magenta dye-forming coupler having the structure: ##STR29## wherein: Q represents the atoms to complete a 5-pyrazolone magenta dye-forming coupler moiety; n is 1 or 2; R is a ballast group when n is 1 or a divalent organic group when n is 2; R 1 is hydrogen or a coupling-off group; and Cp is a coupler moiety which upon reaction by means of oxidized color developing agent yields a colorless or alkali soluble reaction product and is attached at its coupling position to the enol oxygen of the pyrazolone coupler moiety.
Claim 13
Dependent Claim
131 words
A process of forming a magenta dye image in a photographic element comprising a support and a silver halide emulsion, comprising the step of developing the element with a silver halide color developing agent in the presence of a nondiffusible magenta dye-forming coupler having the structure: ##STR29## wherein: Q represents the atoms to complete a 5-pyrazolone magenta dye-forming coupler moiety; n is 1 or 2; R is a ballast group when n is 1 or a divalent organic group when n is 2; R 1 is hydrogen or a coupling-off group; and Cp is a coupler moiety which upon reaction by means of oxidized color developing agent yields a colorless or alkali soluble reaction product and is attached at its coupling position to the enol oxygen of the pyrazolone coupler moiety.
Claim 14
Dependent Claim
13 words
A process of claim 10 wherein the color developing agent is a p-phenylenediamine.
Claim 15
Dependent Claim
135 words
A processed photographic element containing a magenta dye image comprised of a magenta dye obtained by coupling of oxidized silver halide color developing agent and a nondiffusible magenta dye-forming coupler having the structure: ##STR30## wherein: Q represents the atoms to complete a 5-pyrazolone magenta dye-forming coupler moiety; n is 1 or 2; R is a ballast group when n is 1 or a divalent organic group when n is 2; R 1 is hydrogen or a coupling-off group; and Cp is a coupler moiety which upon reaction by means of oxidized color developing agent yields a colorless or alkali soluble reaction product and is attached at its coupling position to the enol oxygen of the pyrazolone coupler moiety; there remaining in areas where magenta dye has not been formed, the blocked magenta dye forming coupler.
Claim 16
Dependent Claim
135 words
A processed photographic element containing a magenta dye image comprised of a magenta dye obtained by coupling of oxidized silver halide color developing agent and a nondiffusible magenta dye-forming coupler having the structure: ##STR30## wherein: Q represents the atoms to complete a 5-pyrazolone magenta dye-forming coupler moiety; n is 1 or 2; R is a ballast group when n is 1 or a divalent organic group when n is 2; R 1 is hydrogen or a coupling-off group; and Cp is a coupler moiety which upon reaction by means of oxidized color developing agent yields a colorless or alkali soluble reaction product and is attached at its coupling position to the enol oxygen of the pyrazolone coupler moiety; there remaining in areas where magenta dye has not been formed, the blocked magenta dye forming coupler.
Claim 17
Dependent Claim
78 words
A processed photographic element of claim 12 wherein the magenta dye-forming coupler has the structure: ##STR31## wherein: Q represents the atoms to complete a 5-pyrazolone magenta dye-forming coupler moiety; n is 1 or 2; R is a ballast group when n is 1 or a divalent organic group when n is 2; R 1 is hydrogen or a coupling-off group and R 2 and R 3 represent the atoms to complete an alkali soluble yellow dye-forming coupler moiety.
Claim 18
Dependent Claim
64 words
A processed photographic element of claim 13 wherein the magenta dye-forming coupler has the structure: ##STR32## wherein: n is 1 or 2; R 4 is hydrogen or a coupling-off group; R 5 is a monovalent or divalent amino or amido ballast group or an alkylene or arylene group; R 6 is aryl; and R 7 is one or more acid or ester solubilizing groups.
Claim 19
Dependent Claim
36 words
A processed photographic element of claim 14 wherein: n is 1; R 4 is hydrogen, aryloxy or arylthio; R 5 is a monovalent amino or amido ballast group; and R 6 is phenyl, alkoxyphenyl or halophenyl.
Claim 20
Dependent Claim
19 words
A processed photographic element of claim 13 wherein the magenta dye-forming coupler has one of the following structures: ##STR33##
Claim 21
Dependent Claim
23 words
A processed photographic element of any one of claims 12, 13, 14, 15 or 16 wherein the color developing agent is a p-phenylenediamine.
Claim 22
Dependent Claim
15 words
A processed photographic element of claim 17 wherein the color developing agent is 4-amino-3-methyl-N-ethyl-N-β-hydroxyethylaniline sulfate.
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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) | 1984-08-10 | 1985-02-09 | 1985-08-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-08-10 | 1989-02-09 | 1989-08-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-08-10 | 1993-02-09 | 1993-08-11 | $7700.00 | Window Closed / Lapsed |