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US3931144A Expired / Lapsed US ⏱️ 0.0 years remaining

Magenta image-providing phenylazonaphthyl dyes

Assignee: Eastman Kodak Co
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Filing: 1974-02-05
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Granted: 1976-01-06
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Expires: 1994-02-05
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Abstract

Abstract A nondiffusible sulfonamide compound which is alkali-cleavable upon oxidation to release a diffusible magenta color-providing moiety from a benzene nucleus thereof, said compound having a formula as follows: ##SPC1## Wherein Ball represents an organic ballasting group. Y represents the carbon atoms necessary to complete a benzene or naphthalene nucleus; X represents a bivalent linking group; R represents hydrogen or alkyl; J represents sulfonyl or carbonyl; M and q each represent an integer having a value of 0 or 1; R 1 represents hydrogen, halogen, alkyl or alkoxy; Q is in the 5- or 8-position relative to the hydroxy radical and represents hydrogen, hydroxy or an acylamino radical; G represents hydroxy, a salt thereof, or a hydrolyzable acyloxy group; E represents hydrogen, sulfo, a sulfamoyl radical; or E can represent a radical of the formula ##SPC2## Wherein Each member is as described previously; R is an integer having a value of 1 or 2; Z represents halogen, carboxy; a carboxylic acid ester; a sulfamoyl radical; as well as hydrogen, alkoxy, an alkyl radical, or a carbamoyl radical; X 1 represents an alkylene, phenylene radical or substituted phenylene as described for R 2 ; X 2 represents an alkylene radical as described for R 2 ; with the proviso that there be only one sulfo or carboxy radical present in said compound and that only one of R 1 and Z be hydrogen.

Inventors

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

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-03 12:04
CPC Classifications
G; G03; G03C; G03C8/00; G03C8/02; G03C8/08; G03C8/10; C; C09; C09B; C09B29/00; Y; Y10; Y10S; Y10S430/00; Y10S430/156

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 542 words
A nondiffusible sulfonamido compound which is alkali-cleavable upon oxidation to release a diffusible colorproviding moiety from a benzene nucleus thereof, said compound having a formula as follows: ##SPC37## wherein Ball represents an organic ballasting group containing at least 8 carbon atoms which renders the compound nondiffusible in a photographic element during development in an alkaline processing composition; Y represents the carbon atoms necessary to complete a benzene or naphthalene nucleus; X represents -R 2 -L n -R 2 p - where each R 2 can be the same or different and each represents alkylene having 1 to 8 carbon atoms; phenylene; or phenylene substituted with chloro, bromo, cyano, nitro, methoxy, methyl, carboxy, or sulfo; L represents 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 2 radicals does not exceed 14 carbon atoms; R represents hydrogen, or alkyl having 1 to 6 carbon atoms; J represents sulfonyl or carbonyl; m and q each represent an integer having a value of 0 or 1; R 1 represents hydrogen, chloro, bromo, fluoro, alkyl having 1 to 6 carbon atoms or alkoxy having 1 to 6 carbon atoms; Q is the 5- or 8-position relative to the hydroxy radical and represents hydrogen, hydroxy, or -NHCOR 3 or -NHSO 2 R 3 wherein R 3 is alkyl having 1 to 6 carbon atoms, alkyl having 1 to 4 carbon atoms substituted with hydroxy, cyano, sulfinyl, carboxy or sulfo; benzyl, phenyl or phenyl substituted with carboxy, chloro, methyl, methoxy, or sulfonyl; G represents hydroxy, an alkali metal salt thereof, a photographically inactive amine salt thereof, or a hydrolyzable acyloxy group having the formula: ##EQU14## wherein R 4 is alkyl having 1 to 18 carbon atoms or phenyl; E represents hydrogen, sulfo, -SO 2 NR 5 R 6 wherein R 5 represents hydrogen or alkyl having 1 to 6 carbon atoms and R 6 represents hydrogen, alkyl having 1 to 6 carbon atoms, alkyl having 1 to 4 carbon atoms substituted with hydroxy, cyano, sulfamoyl, carboxy or sulfo; benzyl; phenyl, or phenyl substituted with hydroxy, sulfonyl, sulfamoyl, carboxy, or sulfo; or E represents ##SPC38## wherein each member is as described previously; r is an integer having a value of 1 or 2; Z represents chloro, bromo, or fluoro; carboxy, -COOR 4 wherein R 4 is as described previously, sulfo, a sulfamoyl radical as described for E, as well as hydrogen, alkoxy having 1 to 6 carbon atoms, alkyl having 1 to 6 carbon atoms, alkyl having 1 to 6 carbon atoms substituted with cyano, hydroxy, sulfamoyl, carboxy, or alkylsulfonamido having 1 to 4 carbon atoms; or -CON(R 5 ) 2 wherein each R 5 is the same or different and is as described previously; X 1 represents alkylene, phenylene or substituted phenylene as described for R 2 ; X 2 represents alkylene as described for R 2 ; with the proviso that there be only one sulfo or carboxy radical present in said compound and that only one of R 1 and Z be hydrogen.
Claim 2
Dependent Claim 542 words
A nondiffusible sulfonamido compound which is alkali-cleavable upon oxidation to release a diffusible colorproviding moiety from a benzene nucleus thereof, said compound having a formula as follows: ##SPC37## wherein Ball represents an organic ballasting group containing at least 8 carbon atoms which renders the compound nondiffusible in a photographic element during development in an alkaline processing composition; Y represents the carbon atoms necessary to complete a benzene or naphthalene nucleus; X represents -R 2 -L n -R 2 p - where each R 2 can be the same or different and each represents alkylene having 1 to 8 carbon atoms; phenylene; or phenylene substituted with chloro, bromo, cyano, nitro, methoxy, methyl, carboxy, or sulfo; L represents 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 2 radicals does not exceed 14 carbon atoms; R represents hydrogen, or alkyl having 1 to 6 carbon atoms; J represents sulfonyl or carbonyl; m and q each represent an integer having a value of 0 or 1; R 1 represents hydrogen, chloro, bromo, fluoro, alkyl having 1 to 6 carbon atoms or alkoxy having 1 to 6 carbon atoms; Q is the 5- or 8-position relative to the hydroxy radical and represents hydrogen, hydroxy, or -NHCOR 3 or -NHSO 2 R 3 wherein R 3 is alkyl having 1 to 6 carbon atoms, alkyl having 1 to 4 carbon atoms substituted with hydroxy, cyano, sulfinyl, carboxy or sulfo; benzyl, phenyl or phenyl substituted with carboxy, chloro, methyl, methoxy, or sulfonyl; G represents hydroxy, an alkali metal salt thereof, a photographically inactive amine salt thereof, or a hydrolyzable acyloxy group having the formula: ##EQU14## wherein R 4 is alkyl having 1 to 18 carbon atoms or phenyl; E represents hydrogen, sulfo, -SO 2 NR 5 R 6 wherein R 5 represents hydrogen or alkyl having 1 to 6 carbon atoms and R 6 represents hydrogen, alkyl having 1 to 6 carbon atoms, alkyl having 1 to 4 carbon atoms substituted with hydroxy, cyano, sulfamoyl, carboxy or sulfo; benzyl; phenyl, or phenyl substituted with hydroxy, sulfonyl, sulfamoyl, carboxy, or sulfo; or E represents ##SPC38## wherein each member is as described previously; r is an integer having a value of 1 or 2; Z represents chloro, bromo, or fluoro; carboxy, -COOR 4 wherein R 4 is as described previously, sulfo, a sulfamoyl radical as described for E, as well as hydrogen, alkoxy having 1 to 6 carbon atoms, alkyl having 1 to 6 carbon atoms, alkyl having 1 to 6 carbon atoms substituted with cyano, hydroxy, sulfamoyl, carboxy, or alkylsulfonamido having 1 to 4 carbon atoms; or -CON(R 5 ) 2 wherein each R 5 is the same or different and is as described previously; X 1 represents alkylene, phenylene or substituted phenylene as described for R 2 ; X 2 represents alkylene as described for R 2 ; with the proviso that there be only one sulfo or carboxy radical present in said compound and that only one of R 1 and Z be hydrogen.
Claim 3
Dependent Claim 21 words
A compound as described in claim 1 wherein m has a value of 0, and r has a value of 1.
Claim 4
Dependent Claim 25 words
A compound as described in claim 1 wherein Y represents the atoms necessary to complete a naphthalene nucleus and r has a value of 1.
Claim 5
Dependent Claim 20 words
A compound as described in claim 1 wherein G is a hydroxy radical, and r has a value of 1.
Claim 6
Dependent Claim 25 words
A compound as described in claim 1 wherein R 1 represents alkoxy having 1 to 4 carbon atoms, and r has a value of 1.
Claim 7
Dependent Claim 235 words
A compound as described in claim 1 wherein Y represents the atoms necessary to complete a naphthalene nucleus; R 2 represents alkylene having 1 to 4 carbon atoms, phenylene or phenylene substituted with carboxy, chloro, methyl or methoxy; L represents sulfamoyl, sulfonamido, carbamoyl or carboxamido; R represents hydrogen; n is 0, p is 0; q is an integer having a value of 1; m is an integer having a value of 0 or 1; R 1 represents alkoxy having 1 to 4 carbon atoms; Q represents hydrogen, hydroxy, -NHCOR 3 or -NHSO 2 R 3 wherein R 3 represents alkyl having 1 to 4 carbon atoms; alkyl having 1 to 4 carbon atoms substituted with hydroxy, cyano, sulfomoyl, carboxy, or sulfo; benzyl, phenyl or phenyl substituted with carboxy, chloro, methyl, methoxy or sulfamoyl; E represents sulfo, --SO 2 NHR 6 wherein R 6 is hydrogen, alkyl having 1 to 4 carbon atoms, or alkyl having 1 to 4 carbon atoms substituted with hydroxy, cyano, sulfamoyl, carboxy or sulfo; benzyl, phenyl or phenyl substituted with hydroxy, sulfonyl, sulfamoyl, carboxy or sulfo; r has a value of 1; and Z represents hydrogen, alkyl having 1 to 4 carbon atoms; chloro; alkyl having 1 to 6 carbon atoms substituted with hydroxy, cyano, sulfamoyl, carboxy, sulfo, or alkylsulfonamido having 1 to 4 carbon atoms; X 1 represents phenylene; and X 2 represents alkylene having 1 to 4 carbon atoms.
Claim 8
Dependent Claim 14 words
A compound as described in claim 6 wherein m has a value of 0.
Claim 9
Dependent Claim 11 words
A compound as described in claim 6 wherein G is hydroxy.
Claim 10
Dependent Claim 55 words
A compound as described in claim 6 wherein X represents phenylene; J represents sulfonyl; X 1 represents phenylene; X 2 represents alkylene of 1 to about 4 carbon atoms; Q represents hydrogen, hydroxy, --NHSO 2 CH 3 , or --NHCOCH 3 ; and Z represents hydrogen, chloro, or --CH 2 NHSO 2 CH 3 .
Claim 11
Dependent Claim 11 words
A compound as described in claim 6 wherein Ball represents ##SPC39##

References Cited (Backward Citations)

US2706684A Cited
US3148062A Cited
US3443940A Cited
US3443939A Cited
US3459548A Cited
US3498785A Cited
US3751406A Cited
US3585028A Cited
US3628952A Cited
US3709693A Cited
US3737316A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1979-01-05 1979-07-07 1980-01-06 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1983-01-05 1983-07-07 1984-01-06 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1987-01-05 1987-07-07 1988-01-06 $7700.00 Window Closed / Lapsed

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