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US4661437A Expired / Lapsed US ⏱️ 0.0 years remaining

Photographic material with heterocylic azo dye for the silver dye bleach process

Assignee: Ha Whitten & Co
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Filing: 1985-07-19
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Granted: 1987-04-28
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Expires: 2005-07-19
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Abstract

Abstract A photographic recording material which contains at least one dye of the formula ##STR1## wherein D is the group of atoms necessary to complete a 5-membered ring that contains at least one nitrogen atom, A is hydrogen, alkyl, alkoxy, phenyl, alkylthio, cyano, nitro or halogen, n is 0 to 3, R 1 is hydrogen, alkyl, hydroxyl, acylamino, R 6 is hydrogen or unsubstituted or substituted amino, and R 4 is hydrogen or alkoxy. The material is distinguished by good color reproduction, brilliant colors and excellent lightfastness.

Inventors

  • 👤 Paul Tschopp

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-05 17:35
CPC Classifications
C; C09; C09B; C09B29/00; C09B29/0025; G; G03; G03C; G03C7/00; G03C7/28; G03C7/29

Claims Analysis

Total Claims: 15
Claim 1
Independent Claim 241 words
A photographic recording material for the silver dye bleach process, which material contains in at least one silver halide emulsion layer, or in a colloidal layer adjacent to said layer or layers, at least one oil-soluble azo dye of the formula ##STR59## wherein D is the group of atoms necessary to complete a 5-membered ring selected from the group consisting of pyrazolyl, imidazolyl, triazolyl, thiazolyl, thiadiazolyl, and isothiadiazolyl rings or the derivatives thereof which are fused with a benzene ring, A is hydrogen, C 1 -C 12 alkyl, C 1 -C 4 alkyl which is substituted by alkoxy, phenoxy, acryl, acyloxy, carbalkoxy, cyano or halogen, or is C 1 -C 4 alkoxy, phenyl, phenyl which is substituted by an electronegative group, or is C 1 -C 4 alkylthio, phenyl-substituted C 1 -C 4 alkylthio, cyano, nitro or halogen, and n is 0, 1, 2 or 3, R 1 is hydrogen, C 1 -C 4 alkyl, hydroxyl, or --NHCOL 1 , wherein L 1 is C 1 -C 20 alkyl or substituted carbamoyl, R 6 is hydrogen or --NR 2 R 3 , wherein each of R 2 and R 3 independently of the other is hydrogen, C 1 -C 8 alkyl or C 1 -C 4 which is substituted by acrylamino, phenyl, alkoxy or hydroxyl, and R 4 is hydrogen, C 1 -C 4 alkoxy or --(OCH 2 CH 2 ) m --OCH 3 , wherein m is 1 or 2.
Claim 2
Dependent Claim 241 words
A photographic recording material for the silver dye bleach process, which material contains in at least one silver halide emulsion layer, or in a colloidal layer adjacent to said layer or layers, at least one oil-soluble azo dye of the formula ##STR59## wherein D is the group of atoms necessary to complete a 5-membered ring selected from the group consisting of pyrazolyl, imidazolyl, triazolyl, thiazolyl, thiadiazolyl, and isothiadiazolyl rings or the derivatives thereof which are fused with a benzene ring, A is hydrogen, C 1 -C 12 alkyl, C 1 -C 4 alkyl which is substituted by alkoxy, phenoxy, acryl, acyloxy, carbalkoxy, cyano or halogen, or is C 1 -C 4 alkoxy, phenyl, phenyl which is substituted by an electronegative group, or is C 1 -C 4 alkylthio, phenyl-substituted C 1 -C 4 alkylthio, cyano, nitro or halogen, and n is 0, 1, 2 or 3, R 1 is hydrogen, C 1 -C 4 alkyl, hydroxyl, or --NHCOL 1 , wherein L 1 is C 1 -C 20 alkyl or substituted carbamoyl, R 6 is hydrogen or --NR 2 R 3 , wherein each of R 2 and R 3 independently of the other is hydrogen, C 1 -C 8 alkyl or C 1 -C 4 which is substituted by acrylamino, phenyl, alkoxy or hydroxyl, and R 4 is hydrogen, C 1 -C 4 alkoxy or --(OCH 2 CH 2 ) m --OCH 3 , wherein m is 1 or 2.
Claim 3
Dependent Claim 24 words
A photographic recording material according to claim 1, wherein the ring formed by D in the dye of formula (1) is a 1-phenyl-3-methylpyrazolyl radical.
Claim 4
Dependent Claim 82 words
A photographic recording material according to claim 2, which contains a dye of formula (1), wherein R 1 is hydrogen or C 1 -C 4 alkyl and R 6 is --NR 2 R 3 , wherein each of R 2 and R 3 independently of the other is C 1 -C 4 alkyl or (CH 2 ) p NHCOL 3 , wherein L 3 is C 4 -C 12 alkyl, p is 1, 2, 3 or 4 and R 4 is hydrogen.
Claim 5
Dependent Claim 26 words
A photographic recording material according to claim 1, wherein the ring formed by D in the dye of formula (1) is a benzpyrazolyl or 1-methylbenzpyrazolyl radical.
Claim 6
Dependent Claim 71 words
A photographic recording material according to claim 4, which contains a dye of formula (1), wherein R 1 is hydrogen or --NHCOL 1 , wherein L 1 is C 6 -C 12 alkyl, R 6 is --NR 2 R 3 , wherein each of R 2 and R 3 independently of the other is C 1 -C 4 alkyl or phenyl-substituted C 1 -C 4 alkyl, and R 4 is hydrogen.
Claim 7
Dependent Claim 59 words
A photographic recording material according to claim 2, wherein the ring formed by D in the dye of formula (1) has the formula ##STR60## wherein A 1 is hydrogen, C 1 -C 4 alkyl or C 1 -C 4 alkyl which is substituted by C 1 -C 4 alkoxy, phenoxy, C 2 -C 8 carbalkoxy, acetyl, benzoyl or cyano.
Claim 8
Dependent Claim 75 words
A photographic recording material according to claim 6, which contains a dye of formula (1), wherein R 1 is --NHCOL 1 wherein L 1 is C 1 -C 14 alkyl or N-methyl-N-phenylcarbamoyl, R 6 is --NR 2 R 3 , wherein each of R 2 and R 3 independently of the other is hydrogen, C 1 -C 8 alkyl, or phenyl- or methoxy-substituted C 1 -C 4 alkyl, and R 4 is hydrogen or methoxy.
Claim 9
Dependent Claim 35 words
A photographic recording material according to claim 1, wherein the ring formed by D in the dye of formula (1) is a 1,2,4-triazolyl radical which may be substituted in the 1-position by a decyl radical.
Claim 10
Dependent Claim 57 words
A photographic recording material according to claim 8, which contains a dye of formula (1), wherein R 1 and R 4 are hydrogen and R 6 is --NR 2 R 3 , wherein each of R 2 and R 3 independently of the other is C 1 -C 4 alkyl or phenyl-substituted C 1 -C 4 alkyl.
Claim 11
Dependent Claim 50 words
A photographic recording material according to claim 1, wherein the ring formed by D in the dye of formula (1) has the formula ##STR61## wherein each of A 2 and A 3 independently of the other is hydrogen, nitro or p-nitrophenyl, or A 4 is C 2 -C 4 alkoxy.
Claim 12
Dependent Claim 108 words
A photographic recording material according to claim 10, which contains a dye of formula (1), wherein R 1 is hydrogen, C 5 -C 10 alkyl, --NHCOL 1 , wherein L 1 is C 1 -C 20 alkyl, R 6 is hydrogen or --NR 2 R 3 , wherein each of R 2 and R 3 independently of the other is hydrogen, C 1 -C 4 alkyl, (CH 2 ) p NHCOL 3 , wherein L 3 is C 1 -C 4 alkyl, p is 1, 2, 3 or 4, or is benzyl, and R 4 is hydrogen, methoxy or --(OCH 2 CH 2 ) 2 OCH 3 .
Claim 13
Dependent Claim 44 words
A photographic recording material according to claim 1, wherein the ring formed by D in the dye of formula (1) has the formula ##STR62## wherein A 5 is phenyl, chlorine, trichloromethane or benzylthio, and A 6 is phenyl or C 1 -C 12 alkyl.
Claim 14
Dependent Claim 81 words
A photographic recording material according to claim 12, which contains a dye of formula (1), wherein R 1 is hydrogen, --NHCOL 1 , wherein L 1 is C 1 -C 20 alkyl, and R 6 is --NR 2 R 3 , wherein each of R 2 and R 3 independently of the other is hydrogen, C 1 -C 6 alkyl, or C 1 -C 4 alkyl which is substituted by methoxy, hydroxyl or phenyl, and R 4 is hydrogen or methoxy.
Claim 15
Dependent Claim 33 words
A process for the production of photographic images by the silver dye bleach process, which comprises exposing, developing, dye bleaching silver bleaching and fixing of a photographic recording material according to claim 1.

References Cited (Backward Citations)

US4456668A Cited
US4396710A Cited
US4524123A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1990-04-27 1990-10-27 1991-04-28 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1994-04-27 1994-10-27 1995-04-28 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1998-04-27 1998-10-27 1999-04-28 $7700.00 Window Closed / Lapsed

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