Patent US4533626A successfully refreshed from Google Patents.
US4533626A
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Photographic light-sensitive material with 4-(paranitrophenylazo)naphthol dyes
Assignee: Fujifilm Holdings Corp
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Filing: 1984-07-27
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Granted: 1985-08-06
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Expires: 2004-07-27
Abstract
Abstract A silver halide photographic light-sensitive material is described, containing a compound represented by formula (I) ##STR1## said compound represented by formula (I) being a novel cyan dye-releasing redox compound having various advantages such as providing a high transfer density, a high transfer speed in dye image portions, and high light-fastness.
Inventors
- 👤 Shigetoshi Ono
- 👤 Toru Harada
- 👤 Hirohisa Suzuki
- 👤 Mitsugu Tanaka
- 👤 Shigeru Nakamura
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 19:39
CPC Classifications
C; C09; C09B; C09B29/00; C09B29/10; C09B29/18; C09B29/20; G; G03; G03C; G03C8/00; G03C8/02; G03C8/08; G03C8/10; Y; Y10; Y10S; Y10S534/00; Y10S534/02
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
452 words
A silver halide photographic light-sensitive material containing a compound represented by formula (I) ##STR102## wherein R 1 is an alkyl group or a substituted alkyl group; R 2 is --NHSO 2 R 2' [wherein R 2' is a substituted or unsubstituted alkyl group, an aryl group, a heterocyclic ring, or ##STR103## (wherein D and D' may be the same or different and are each a hydrogen atom or an alkyl group)], or --SO 2 NH--R 2" (wherein R 2" is a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group), and may be positioned at any of the ortho-, meta-, and para-positions relative to the ##STR104## group; m is an integer of 1 or 2; W is --SO 2 -- or --CO--; X is a divalent connecting group represented by the formula --R 3 --L n --R 3' p -- (wherein R 3 and R 3' may be the same or different, and are each a substituted or unsubstituted alkylene group, a substituted or unsubstituted arylene group, or a substituted or unsubstituted aralkylene group; L is a divalent group selected from an oxy group, a carbonyl group, a carboxyamido group, a carbamoyl group, a sulfonamido group, a sulfamoyl group, a sulfinyl group, and a sulfonyl group; and n and p are each 0 or an integer of 1); Y is a redox center capable of releasing a diffusible dye on undergoing a self-cleavage as a result of a redox reaction; Z 1 is a halogen atom, a cyano group, a nitro group, a trifluoromethyl group, an alkyl group, an alkoxy group, a carboxyl group, a carboxylic acid ester group represented by the formula --COOR 4 (wherein R 4 is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted phenyl group), a fluorosulfonyl group, a substituted or unsubstituted phenoxysulfonyl group, a group represented by the formula --SO 2 NR 5 R 6 (wherein R 5 is a hydrogen atom, a substituted or unsubstituted alkyl group; R 6 is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group; and R 5 and R 6 may be combined together directly or through an oxygen atom to form a ring), a group represented by the formula --CONR 5 R 6 (wherein R 5 and R 6 are the same as defined above), a substituted or unsubstituted alkylsulfonyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted phenylsulfonyl group; Z 2 is a hydrogen atom, a halogen atom, a nitro group, a cyano group, or a trifluoromethyl group; and A is a hydroxyl group or a group forming a hydroxyl group upon decomposition.
Claim 2
Dependent Claim
452 words
A silver halide photographic light-sensitive material containing a compound represented by formula (I) ##STR102## wherein R 1 is an alkyl group or a substituted alkyl group; R 2 is --NHSO 2 R 2' [wherein R 2' is a substituted or unsubstituted alkyl group, an aryl group, a heterocyclic ring, or ##STR103## (wherein D and D' may be the same or different and are each a hydrogen atom or an alkyl group)], or --SO 2 NH--R 2" (wherein R 2" is a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aryl group), and may be positioned at any of the ortho-, meta-, and para-positions relative to the ##STR104## group; m is an integer of 1 or 2; W is --SO 2 -- or --CO--; X is a divalent connecting group represented by the formula --R 3 --L n --R 3' p -- (wherein R 3 and R 3' may be the same or different, and are each a substituted or unsubstituted alkylene group, a substituted or unsubstituted arylene group, or a substituted or unsubstituted aralkylene group; L is a divalent group selected from an oxy group, a carbonyl group, a carboxyamido group, a carbamoyl group, a sulfonamido group, a sulfamoyl group, a sulfinyl group, and a sulfonyl group; and n and p are each 0 or an integer of 1); Y is a redox center capable of releasing a diffusible dye on undergoing a self-cleavage as a result of a redox reaction; Z 1 is a halogen atom, a cyano group, a nitro group, a trifluoromethyl group, an alkyl group, an alkoxy group, a carboxyl group, a carboxylic acid ester group represented by the formula --COOR 4 (wherein R 4 is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted phenyl group), a fluorosulfonyl group, a substituted or unsubstituted phenoxysulfonyl group, a group represented by the formula --SO 2 NR 5 R 6 (wherein R 5 is a hydrogen atom, a substituted or unsubstituted alkyl group; R 6 is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted aryl group; and R 5 and R 6 may be combined together directly or through an oxygen atom to form a ring), a group represented by the formula --CONR 5 R 6 (wherein R 5 and R 6 are the same as defined above), a substituted or unsubstituted alkylsulfonyl group, a substituted or unsubstituted aralkyl group, or a substituted or unsubstituted phenylsulfonyl group; Z 2 is a hydrogen atom, a halogen atom, a nitro group, a cyano group, or a trifluoromethyl group; and A is a hydroxyl group or a group forming a hydroxyl group upon decomposition.
Claim 3
Dependent Claim
413 words
A silver halide photographic light-sensitive material as in claim 1, wherein R 1 is an alkyl group having from 1 to 6 carbon atoms or a substituted alkyl group having from 1 to 10 carbon atoms; R 2 is an alkanesulfonamido group having from 1 to 6 carbon atoms, an unsubstituted sulfamoyl group or an alkylsulfamoyl group having from 1 to 6 carbon atoms; m is 1 or 2; W is --SO 2 --; X is a divalent connecting group represented by the formula --R 3 --L n --R 3' p --, wherein R 3 or R 3' is an alkylene group having from 1 to 6 carbon atoms, a substituted alkylene group having from 1 to 10 carbon atoms, an arylene group, or a substituted arylene group; L, n and p each has the same meanings as those in claim 1; Y is a redox center capable of releasing a diffusible dye on undergoing a self-cleavage as a result of a redox reaction; Z 1 is a halogen atom, a cyano group, a nitro group, a straight or branched alkyl group having from 1 to 6 carbon atoms, a straight or branched alkoxy group having from 1 to 8 carbon atoms, --SO 2 NR 5 R 6 wherein R 5 is hydrogen or a substituted or unsubstituted alkyl group having from 1 to 6 carbon atoms, R 6 is a hydrogen atom, an alkyl group having from 1 to 6 carbon atoms, a benzyl group, or a substituted or unsubstituted phenyl group having from 6 to 9 carbon atoms, or R 5 and R 6 combine together to form a 5- or 6-membered heterocyclic ring, --CONR 5 R 6 , wherein R 5 and R 6 are the same as defined above, --SO 2 R 10 , wherein R 10 is a substituted or unsubstituted alkyl group having from 1 to 6 carbon atoms or a benzyl group, or --COOR 7 , wherein R 7 is a substituted or unsubstituted alkyl group having from 1 to 6 carbon atoms or a substituted or unsubstituted phenyl group having from 6 to 10 carbon atoms; Z 2 is a hydrogen atom, a halogen atom, a nitro group, a cyano group or a trifluoromethyl group; and A is a hydroxyl group ##STR105## group, wherein G represents an alkyl group having from 1 to 18 carbon atoms, a halogen-substituted alkyl group having from 1 to 18 carbon atoms, a phenyl group, or a substituted phenyl group.
Claim 4
Dependent Claim
167 words
A silver halide photographic light-sensitive material as in claim 1, wherein R 1 is an alkyl group having from 1 to 3 carbon atoms; R 2 is --NHSO 2 R 2' wherein R 2' is an alkyl group having from 1 to 3 carbon atoms or --SO 2 NHR 2" wherein R 2" is a hydrogen atom or an alkyl group having from 1 to 3 carbon atoms; W is --SO 2 --; X is ##STR106## Z 1 is a halogen atom, a cyano atom, a nitro atom, --SO 2 NR 5 R 6 wherein R 5 and R 6 , which is the same or different, each represents a hydrogen atom, or an alkyl group having from 1 to 3 carbon atoms, or an alkylsulfonyl group having from 1 to 3 carbon atoms; Z 2 is a hydrogen atom, a halogen atom, a nitro group, or a cyano group; the redox center represented by Y is an N-substituted sulfamoyl group; and A is a hydroxyl group.
Claim 5
Dependent Claim
27 words
A silver halide photographic light-sensitive material as in claim 3, wherein the N-substituent for the N-substituted sulfamoyl group is a carbon ring group or a heterocyclic group.
Claim 6
Dependent Claim
22 words
A silver halide photographic light-sensitive material as in claim 1, wherein the redox center represented by Y is an N-substituted sulfamoyl group.
Claim 7
Dependent Claim
27 words
A silver halide photographic light-sensitive material as in claim 5, wherein the N-substituent for the N-substituted sulfamoyl group is a carbon ring group or a heterocyclic group.
Claim 8
Dependent Claim
29 words
A silver halide photographic light-sensitive material as in claim 2, wherein the substituted arylene group for R 3 or R 3' has from 6 to about 11 carbon atoms.
Claim 9
Dependent Claim
157 words
A silver halide photographic light-sensitive material as in claim 1, wherein Y is a group represented by formula (II) ##STR107## wherein β represents a non-metallic atomic group forming a benzene ring, to which a carbon ring or a hetero ring may be fused; α represents a group of the formula --OG 1 or --NHG 2 , wherein G 1 is a hydrogen atom or a group forming a hydroxyl group or hydrolysis, and G 2 is a hydrogen atom, an alkyl group having from 1 to 22 carbon atoms, or a hydrolyzable group; b is 0 or an integer of 1 or 2, wherein when α is a group of the formula --OG 1 , or α is a group of the formula --NHG 2 and G 2 is a hydrogen atom, an alkyl group having from 1 to 8 carbon atoms, or a hydrolyzable group, b is 1 or 2 and; Ball represents a ballast group.
Claim 10
Dependent Claim
157 words
A silver halide photographic light-sensitive material as in claim 2, wherein Y is a group represented by formula (II) ##STR108## wherein β represents a non-metallic atomic group forming a benzene ring, to which a carbon ring or a hetero ring may be fused; α represents a group of the formula --OG 1 or --NHG 2 , wherein G 1 is a hydrogen atom or a group forming a hydroxyl group on hydrolysis, and G 2 is a hydrogen atom, an alkyl group having from 1 to 22 carbon atoms, or a hydrolyzable group; b is 0 or an integer of 1 or 2, wherein when α is a group of the formula --OG 1 , or α is a group of the formula --NHG 2 and G 2 is a hydrogen atom, an alkyl group having from 1 to 8 carbon atoms, or a hydrolyzable group, b is 1 or 2 and; Ball represents a ballast group.
Claim 11
Dependent Claim
156 words
A silver halide photographic light-sensitive material as in claim 1, wherein Y is a group represented by formula (III) ##STR109## wherein β' is an atomic group forming a carbon ring to which a carbon ring or a hetero ring may be fused; α represents a group of the formula --OG 1 or --NHG 2 , wherein G 1 is a hydrogen atom or a group forming a hydroxyl group on hydrolysis, and G 2 is a hydrogen atom, an alkyl group having from 1 to 22 carbon atoms, or a hydrolyzable group; b is 0 or an integer of 1 or 2, wherein when α is a group of the formula --OG 1 , or α is a group of the formula --NHG 2 and G 2 is a hydrogen atom, an alkyl group having from 1 to 8 carbon atoms, or a hydrolyzable group, b is 1 or 2; and Ball represents a ballast group.
Claim 12
Dependent Claim
156 words
A silver halide photographic light-sensitive material as in claim 2, wherein Y is a group represented by formula (III) ##STR110## wherein β' is an atomic group forming a carbon ring to which a carbon ring or a hetero ring may be fused; α represents a group of the formula --OG 1 or --NHG 2 , wherein G 1 is a hydrogen atom or a group forming a hydroxyl group on hydrolysis, and G 2 is a hydrogen atom, an alkyl group having from 1 to 22 carbon atoms, or a hydrolyzable group; b is 0 or an integer of 1 or 2, wherein when α is a group of the formula --OG 1 , or α is a group of the formula --NHG 2 and G 2 is a hydrogen atom, an alkyl group having from 1 to 8 carbon atoms, or a hydrolyzable group, b is 1 or 2 and; Ball represents a ballast group.
Claim 13
Dependent Claim
144 words
A silver halide photographic light-sensitive material as in claim 1, wherein Y is a group represented by formula (IV) ##STR111## wherein β" represents an atomic group forming a hetero ring; α represents a group of the formula --OG 1 or --NHG 2 , wherein G 1 is a hydrogen atom or a group forming a hydroxyl group on hydrolysis, and G 2 is a hydrogen atom, an alkyl group having from 1 to 22 carbon atoms, or a hydrolyzable group; b is 0 or an integer of 1 or 2, wherein when α is a group of the formula --OG 1 , or α is a group of the formula --NHG 2 and G 2 is a hydrogen atom, an alkyl group having from 1 to 8 carbon atoms, or a hydrolyzable group, b is 1 or 2; and Ball represents a ballast group.
Claim 14
Dependent Claim
144 words
A silver halide photographic light-sensitive material as in claim 2, wherein Y is a group represented by formula (IV) ##STR112## wherein β" represents an atomic group forming a hetero ring; α represents a group of the formula --OG 1 or --NHG 2 , wherein G 1 is a hydrogen atom or a group forming a hydroxyl group on hydrolysis, and G 2 is a hydrogen atom, an alkyl group having from 1 to 22 carbon atoms, or a hydrolyzable group; b is 0 or an integer of 1 or 2, wherein when α is a group of the formula --OG 1 , or α is a group of the formula --NHG 2 and G 2 is a hydrogen atom, an alkyl group having from 1 to 8 carbon atoms, or a hydrolyzable group, b is 1 or 2; and Ball represents a ballast group.
Claim 15
Dependent Claim
137 words
A silver halide photographic light-sensitive material as in claim 1, wherein Y is a group represented by formula (V) ##STR113## wherein γ is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, or --CO--G 6 wherein G 6 represents --OG 7 , --S--G 7 or ##STR114## wherein G 7 is a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group, which may be substituted, G 8 is selected from the same group as defined for G 7 , or an acyl group derived from an aliphatic or aromatic carboxylic acid or sulfonic acid, and G 9 is a hydrogen atom or a substituted or unsubstituted alkyl group and; δ is an atomic group forming a condensed benzene ring which may be substituted.
Claim 16
Dependent Claim
137 words
A silver halide photographic light-sensitive material as in claim 2, wherein Y is a group represented by formula (V) ##STR115## wherein γ is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, or --CO--G 6 wherein G 6 represents --OG 7 , --S--G 7 or ##STR116## wherein G 7 is a hydrogen atom, an alkyl group, a cycloalkyl group, or an aryl group, which may be substituted, G 8 is selected from the same group as defined for G 7 , or an acyl group derived from an aliphatic or aromatic carboxylic acid or sulfonic acid, and G 9 is a hydrogen atom or a substituted or unsubstituted alkyl group and; δ is an atomic group forming a condensed benzene ring which may be substituted.
Claim 17
Dependent Claim
32 words
A silver halide photographic light-sensitive material as in claim 1, wherein the compound of formula (I) is incorporated in an amount of from about 1×10 -4 to 1×10 -2 mol/m 2 .
Claim 18
Dependent Claim
32 words
A silver halide photographic light-sensitive material as in claim 1, wherein the compound of formula (I) is incorporated in an amount of from about 2×10 -4 to 2×10 -3 mol/m 2 .
Claim 19
Dependent Claim
32 words
A silver halide photographic light-sensitive material as in claim 2, wherein the compound of formula (I) is incorporated in an amount of from about 1×10 -4 to 1×10 -2 mol/m 2 .
Claim 20
Dependent Claim
32 words
A silver halide photographic light-sensitive material as in claim 2, wherein the compound of formula (I) is incorporated in an amount of from about 2×10 -4 to 2×10 -3 mol/m 2 .
Claim 21
Dependent Claim
42 words
A silver halide photographic light-sensitive material as in claim 1, wherein Y is a redox center capable of releasing a diffusible dye under alkaline conditions, but does not substantially cause the dye release when directly or indirectly reacted with an oxidized developer.
Claim 22
Dependent Claim
24 words
A silver halide photographic light-sensitive material as in claim 1, wherein Y is a redox center capable of releasing a diffusible dye by reduction.
Claim 23
Dependent Claim
29 words
A silver halide photographic light-sensitive material as in claim 1, comprising a support having thereon at least a silver halide emulsion layer associated therewith the compound of formula (I).
References Cited (Backward Citations)
US3942987A
Cited
US4273708A
Cited
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| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
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| 3.5 Years (Year 4) | 1988-08-05 | 1989-02-04 | 1989-08-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-08-05 | 1993-02-04 | 1993-08-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-08-05 | 1997-02-04 | 1997-08-06 | $7700.00 | Window Closed / Lapsed |