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US4013633A Expired / Lapsed US ⏱️ 0.0 years remaining

Yellow azopyrazoline dye releasing redox compounds for photographic color transfer

Assignee: Eastman Kodak Co
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Filing: 1975-06-27
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Granted: 1977-03-22
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Expires: 1995-06-27
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Abstract

Abstract A photosensitive element comprising a support having thereon at least one photosensitive silver halide emulsion layer and one of said layers having associated therewith a yellow image dye-releasing compound having a formula as follows ##STR1## wherein Car represents a sulfonamidophenol or sulfonamidonaphthol carrier moiety which, as a function of oxidation under alkaline conditions, releases a diffusible dye from said compound. X represents a bivalent linking group of the formula --R 1 --L n --R 1 p -- where each R 1 can be the same or different and each represents alkylene phenylene; or substituted phenylene; L represents a bivalent radical selected from oxy, carbonyl, carboxamido, carbamoyl, sulfonamido, sulfamoyl, sulfinyl or sulfonyl; n is an integer having a value of 0 or 1; p is 1 when n equals 1 and p is 1 or 0 when n equals 0, provided that when p is 1 the carbon content of the sum of both R radicals does not exceed 14 carbon atoms; R represents hydrogen or alkyl; J represents a bivalent radical selected from sulfonyl or carbonyl; m and q each represent an integer having a value of 0 or 1; E represents hydrogen, halogen, alkyl or alkoxy; Z represents hydrogen or an electron withdrawing group selected from cyano, trifluoromethyl, alkylsulfonyl, substituted alkylsulfonyl, phenylsulfonyl, or substituted phenylsulfonyl; a carboxylic acid ester having the formula --COOR 2 wherein R 2 is alkyl, phenyl or substituted phenyl; sulfo, a sulfamoyl radical having the formula --SO 2 NR 3 R 4 wherein R 3 represents hydrogen or alkyl, and R 4 represents hydrogen, alkyl, substituted alkyl; benzyl, phenyl, substituted phenyl; alkylcarbonyl, or phenylcarbonyl, with the proviso that the carbon content of the sum of R 3 and R 4 not exceed 14 carbon atoms; a carbamoyl radical having the formula --CON(R 3 ) 2 wherein each R 3 can be the same or different and is as described previously; and M represents hydrogen, a solubilizing group or precursor thereof selected from carboxy, sulfo, a sulfamoyl radical as described for Z or a carboxylic acid ester as described for Z.

Inventors

  • 👤 Jan R. Haase
  • 👤 Carl H. Eldredge
  • 👤 Richard A. Landholm

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-01 07:24
CPC Classifications
G; G03; G03C; G03C8/00; G03C8/02; G03C8/08; G03C8/10; C; C09; C09B; C09B29/00; C09B29/34; C09B29/36; C09B29/3604; C09B29/3647; C09B29/3652; C09B29/366; C09B43/00

Claims Analysis

Total Claims: 24
Claim 1
Independent Claim 452 words
A yellow image dye-releasing compound having a formula as follows ##STR36## wherein CAR represents a ballasted o- or p-sulfonamidophenol or o- or p-sulfonamidonaphthol carrier moiety which, as a function of oxidation under alkaline conditons, releases a diffusible dye from said compound; X represents a bivalent linking group of the formula --R 1 --L n --R 1 p --where each R 1 can be the same or different and each represents alkylene having 1 to about 8 carbon atoms; phenylene; or phenylene substituted with carboxy, chloro, methyl or methoxy; L represents a bivalent radical selected from oxy, carbonyl, carboxamido, carbamoyl, sulfonamido, sulfamoyl, sulfinyl or sulfonyl; n is an integer having a value of 0 or 1; p is 1 when n equals 1 and p is 1 or 0 when n equals 0, provided that when p is 1 the carbon content of the sum of both R radicals does not exceed 14 carbon atoms; R represents hydrogen or alkyl having 1 to about 6 carbon atoms; J represents a bivalent radical selected from sulfonyl or carbonyl; m and q each represent an integer having a value of 0 or 1; E represents hydrogen, chloro, bromo, fluoro, alkyl having 1 to about 4 carbon atoms or alkoxy having 1 to about 4 carbon atoms; Z represents hydrogen or an electron withdrawing group selected from cyano, trifluoromethyl, alkylsulfonyl having 1 to about 8 carbon atoms, alkylsulfonyl having 1 to about 8 carbon atoms substituted with hydroxy, phenyl, cyano, sulfamoyl, carboxy, fluorosulfonyl or sulfo; phenylsulfonyl or phenylsulfonyl substituted with carboxy, hydroxy, sulfamoyl, fluorosulfonyl, carboxy or sulfo; a carboxylic acid ester having the formula --COOR 2 wherein R 2 is alkyl having 1 to about 18 carbon atoms, phenyl or phenyl substituted with chloro or nitro; sulfo, a sulfamoyl radical having the formula --SO 2 NR 3 R 4 wherein R 3 represents hydrogen or alkyl having 1 to about 6 carbon atoms and R 4 represents hydrogen, alkyl having 1 to about 6 carbon atoms, alkyl having 1 to about 6 carbon atoms substituted with hydroxy, cyano, fluorosulfonyl, carboxy or sulfo; benzyl, phenyl, phenyl substituted with hydroxy, sulfonyl, sulfamoyl, carboxy or sulfo; alkylcarbonyl having 1 to about 8 carbon atoms, or phenylcarbonyl having 6 to about 9 carbon atoms, with the proviso that the carbon content of the sum of R 3 and R 4 not exceed 14 carbon atoms; a carbamoyl radical having the formula --CON(R 3 ) 2 wherein each R 3 can be the same or different and is as described previously; and M represents hydrogen, a solubilizing group or precursor thereof selected from carboxy, sulfo, a sulfamoyl radical as described for Z or a carboxylic acid ester as described for Z.
Claim 2
Dependent Claim 452 words
A yellow image dye-releasing compound having a formula as follows ##STR36## wherein CAR represents a ballasted o- or p-sulfonamidophenol or o- or p-sulfonamidonaphthol carrier moiety which, as a function of oxidation under alkaline conditons, releases a diffusible dye from said compound; X represents a bivalent linking group of the formula --R 1 --L n --R 1 p --where each R 1 can be the same or different and each represents alkylene having 1 to about 8 carbon atoms; phenylene; or phenylene substituted with carboxy, chloro, methyl or methoxy; L represents a bivalent radical selected from oxy, carbonyl, carboxamido, carbamoyl, sulfonamido, sulfamoyl, sulfinyl or sulfonyl; n is an integer having a value of 0 or 1; p is 1 when n equals 1 and p is 1 or 0 when n equals 0, provided that when p is 1 the carbon content of the sum of both R radicals does not exceed 14 carbon atoms; R represents hydrogen or alkyl having 1 to about 6 carbon atoms; J represents a bivalent radical selected from sulfonyl or carbonyl; m and q each represent an integer having a value of 0 or 1; E represents hydrogen, chloro, bromo, fluoro, alkyl having 1 to about 4 carbon atoms or alkoxy having 1 to about 4 carbon atoms; Z represents hydrogen or an electron withdrawing group selected from cyano, trifluoromethyl, alkylsulfonyl having 1 to about 8 carbon atoms, alkylsulfonyl having 1 to about 8 carbon atoms substituted with hydroxy, phenyl, cyano, sulfamoyl, carboxy, fluorosulfonyl or sulfo; phenylsulfonyl or phenylsulfonyl substituted with carboxy, hydroxy, sulfamoyl, fluorosulfonyl, carboxy or sulfo; a carboxylic acid ester having the formula --COOR 2 wherein R 2 is alkyl having 1 to about 18 carbon atoms, phenyl or phenyl substituted with chloro or nitro; sulfo, a sulfamoyl radical having the formula --SO 2 NR 3 R 4 wherein R 3 represents hydrogen or alkyl having 1 to about 6 carbon atoms and R 4 represents hydrogen, alkyl having 1 to about 6 carbon atoms, alkyl having 1 to about 6 carbon atoms substituted with hydroxy, cyano, fluorosulfonyl, carboxy or sulfo; benzyl, phenyl, phenyl substituted with hydroxy, sulfonyl, sulfamoyl, carboxy or sulfo; alkylcarbonyl having 1 to about 8 carbon atoms, or phenylcarbonyl having 6 to about 9 carbon atoms, with the proviso that the carbon content of the sum of R 3 and R 4 not exceed 14 carbon atoms; a carbamoyl radical having the formula --CON(R 3 ) 2 wherein each R 3 can be the same or different and is as described previously; and M represents hydrogen, a solubilizing group or precursor thereof selected from carboxy, sulfo, a sulfamoyl radical as described for Z or a carboxylic acid ester as described for Z.
Claim 3
Dependent Claim 136 words
A compound as described in claim 1 wherein Car represents a carrier moiety which, as a function of oxidation under alkaline conditions, releases a diffusible dye from said compound and having the formula ##STR37## wherein Ball represents an organic ballasting group containing at least 8 carbon atoms which renders said compound nondiffusible in said photographic element during development in an alkaline processing composition; Y represents the carbon atoms necessary to complete a benzene or naphthalene nucleus; R 1 represents alkylene having 1 to about 4 carbon atoms, phenylene or phenylene substituted with carboxy, chloro, methyl or methoxy; L represents sulfamoyl, sulfonamido, carbamoyl or carboxamido; R represents hydrogen; q is an integer having a value of 1; m is an integer having a value of 1 or 0; E represents hydrogen, chloro, methoxy, ethoxy, propoxy or isopropoxy;
Claim 4
Dependent Claim 133 words
Z represents cyano, alkylsulfonyl having 1 to about 6 carbon atoms, alkylsulfonyl having 1 to about 6 carbon atoms substituted with hydroxy, phenyl, cyano, sulfamoyl, carboxy, fluorosulfonyl or sulfo; phenylsulfonyl; phenylsulfonyl substituted with hydroxy, sulfamoyl, fluorosulfonyl, carboxy or sulfo; a sulfamoyl radical having the formula --SO 2 NHR 4 wherein R 6 is hydrogen, alkyl having 1 to about 4 carbon atoms, phenyl; or a carbamoyl radical having the formula --CON(R 3 ) 2 wherein R 3 is hydrogen or methyl; and M represents hydrogen, a carboxylic acid ester having the formula --COOR 2 wherein R 2 is alkyl having 1 to about 4 carbon atoms, phenyl; or a sulfamoyl radical having the formula --SO 2 NHR 4 wherein R 4 is hydrogen, alkyl having 1 to about 4 carbon atoms or phenyl.
Claim 5
Dependent Claim 133 words
Z represents cyano, alkylsulfonyl having 1 to about 6 carbon atoms, alkylsulfonyl having 1 to about 6 carbon atoms substituted with hydroxy, phenyl, cyano, sulfamoyl, carboxy, fluorosulfonyl or sulfo; phenylsulfonyl; phenylsulfonyl substituted with hydroxy, sulfamoyl, fluorosulfonyl, carboxy or sulfo; a sulfamoyl radical having the formula --SO 2 NHR 4 wherein R 6 is hydrogen, alkyl having 1 to about 4 carbon atoms, phenyl; or a carbamoyl radical having the formula --CON(R 3 ) 2 wherein R 3 is hydrogen or methyl; and M represents hydrogen, a carboxylic acid ester having the formula --COOR 2 wherein R 2 is alkyl having 1 to about 4 carbon atoms, phenyl; or a sulfamoyl radical having the formula --SO 2 NHR 4 wherein R 4 is hydrogen, alkyl having 1 to about 4 carbon atoms or phenyl.
Claim 6
Dependent Claim 37 words
A compound according to claim 2 wherein Car[X-(NR-J) q ] m is in the meta position relative to the azo linkage in Formula I, and in the para position relative to the pyrazolone nitrogen in Formula II.
Claim 7
Dependent Claim 10 words
A compound according to claim 3 wherein m is 0.
Claim 8
Dependent Claim 55 words
A compound according to claim 4 wherein Y represents the atoms necessary to complete a naphthalene nucleus; Z represents alkylsulfonyl having 1 to about 8 carbon atoms, cyano, or a sulfamoyl radical having the formula --SO 2 NHR 4 wherein R 4 is alkyl having 1 to about 4 carbon atoms; and M is hydrogen.
Claim 9
Dependent Claim 22 words
A compound according to claim 5 wherein --Ball is linked to the sulfonamidonaphthol nucleus through a bivalent --CONH-- or --SO.sub.2 NH-- moiety.
Claim 10
Dependent Claim 20 words
A compound according to claim 5 wherein --Ball represents ##STR38## and is in the 2-position relative to the hydroxy group.
Claim 11
Dependent Claim 21 words
A compound according to claim 7 wherein E represents hydrogen, chloro or methoxy; and Z represents --SO 2 CH 3 .
Claim 12
Dependent Claim 9 words
A yellow image dye-releasing compound having the formula ##STR39##
Claim 13
Dependent Claim 9 words
A yellow image dye-releasing compound having the formula ##STR39##
Claim 14
Dependent Claim 9 words
A yellow image dye-releasing compound having the formula ##STR40##
Claim 15
Dependent Claim 9 words
A yellow image dye-releasing compound having the formula ##STR40##
Claim 16
Dependent Claim 17 words
A compound according to claim 3 wherein ##STR41## J is --SO 2 --; and q is 1.
Claim 17
Dependent Claim 56 words
A photosensitive element according to claim 11 wherein Y represents the atoms necessary to complete a naphthalene nucleus; Z represents alkylsulfonyl having 1 to about 6 carbon atoms, cyano or a sulfamoyl radical having the formula --SO 2 NHR 4 wherein R 4 is alkyl having 1 to about 4 carbon atoms; and M is hydrogen.
Claim 18
Dependent Claim 22 words
A compound according to claim 12 wherein --Ball is linked to the sulfonamidonaphthol nucleus through a bivalent --CONH-- or --SO.sub.2 NH-- moiety.
Claim 19
Dependent Claim 20 words
A compound according to claim 12 wherein --Ball represents ##STR42## and is in the 2-position relative to the hydroxy group.
Claim 20
Dependent Claim 30 words
A compound according to claim 14 wherein E represents hydrogen, chloro or methoxy; and Z represents --SO 2 CH 3 , cyano or --SO 2 N(CH 3 ) 2 .
Claim 21
Dependent Claim 9 words
A yellow image dye-releasing compound having the formula ##STR43##
Claim 22
Dependent Claim 9 words
A yellow image dye-releasing compound having the formula ##STR43##
Claim 23
Dependent Claim 9 words
A yellow image dye-releasing compound having the formula ##STR44##
Claim 24
Dependent Claim 9 words
A yellow image dye-releasing compound having the formula ##STR44##

References Cited (Backward Citations)

US3148062A Cited
US3288778A Cited
US3751406A Cited
US3923779A Cited
US3928312A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1980-03-21 1980-09-20 1981-03-22 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1984-03-21 1984-09-20 1985-03-22 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1988-03-21 1988-09-20 1989-03-22 $7700.00 Window Closed / Lapsed

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