Monoazo Patents (Class 430/562)
  • Patent number: 4528258
    Abstract: A process for forming an image which comprises heating a light-sensitive material comprising a support having thereon at least a light-sensitive silver halide, a binder and a dye-releasing redox compound which is reductive to the light-sensitive silver halide and which is capable of releasing a hydrophilic dye upon reaction with the light-sensitive silver halide on heating, after imagewise exposure or simultaneously with imagewise exposure, in a substantially water-free condition the dye-releasing redox compound being represented by the formula (I) wherein R represents a phenyl group having a hydroxy-substituted alkoxy group or an alkoxy-substituted alkoxy group at at least the 2-position thereof with respect to the diazo group and a group of the formula --SO.sub.2 NH--Y at the 5-position thereof with respect to the diazo group where Y represents a group capable of being oxidized silver halide to release a dye moiety including the --SO.sub.2 NH moiety.
    Type: Grant
    Filed: March 12, 1984
    Date of Patent: July 9, 1985
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Hiroshi Kitaguchi, Hideki Naito
  • Patent number: 4524122
    Abstract: Photographic elements and diffusion transfer assemblages employing a nondiffusible compound capable of releasing at least one diffusible cyan dye moiety, and having the formula: ##STR1## wherein: (a) J represents SO.sub.2 or CO,(b) R represents a substituted or unsubstituted alkyl group of from 1 to about 10 carbon atoms or a substituted or unsubstituted aryl group of from 6 to about 12 carbon atoms,(c) G represents a hydroxy group, a salt thereof, or a hydrolyzable precursor thereof,(d) CAR represents a ballasted carrier moiety, and(e) D.sup.1, D.sup.2, and D.sup.3 each independently represents H or one or more electron-withdrawing groups selected from --SO.sub.2 Y.sup.1, --CONY.sup.1 Y.sup.2, --Cl, --COY.sup.1, --C.tbd.N and --SO.sub.2 NY.sup.1 Y.sup.2, where Y.sup.1 and Y.sup.2 each independently represents hydrogen, a substituted or unsubstituted alkyl group of from 1 to about 10 carbon atoms or a substituted or unsubstituted aryl group of from 6 to about 12 carbon atoms.
    Type: Grant
    Filed: September 26, 1984
    Date of Patent: June 18, 1985
    Assignee: Eastman Kodak Company
    Inventors: Lynda D. Weber, Paul B. Merkel, Harold C. Warren, III
  • Patent number: 4524124
    Abstract: Monoazo dyes corresponding to the following formula ##STR1## are suitable for use as light-stable cyan image dyes stable to reducing agents for the dye diffusion transfer process.In the above formula:Q represents the remainder of the molecule required to complete a fused benzene or thiophene ring, which contains additional electron acceptor groups, or to complete a fused pyridine, pyrimidine, pyridazine, pyrazine or thiazole ring;G represents --OH, acyloxy;R.sup.1 represents H or one or two identical or different radicals selected from the group consisting of halogen, acyl, acylamino and --CN;Y represents H, --OH, an amino group optionally substituted by alkyl or aryl, a cyclic amino group or a group of the formula --NH--SO.sub.2 --R.sup.2 ;R.sup.2 represents alkyl, aryl, an amino group optionally substituted twice by alkyl or a cyclic amino group;n=0, 1 or 2.
    Type: Grant
    Filed: June 18, 1984
    Date of Patent: June 18, 1985
    Assignee: Agfa-Gevaert Aktiengesellschaft
    Inventors: Peter Bergthaller, Rudolf Stolzenburg, Paul Marx, Rainer Hamprecht
  • Patent number: 4524123
    Abstract: Azo dyes corresponding to the formula (II): ##STR1## wherein G represents a group capable of forming a 5-membered chelate ring and R.sup.5 represents aryl or a thienyl group, combined with metal ions, in particular copper or nickel ions, to form stable azo dye-metal complexes which have advantageous spectral properties. They are therefore particularly suitable for the production of highly light-fast cyan images, e.g. by the Ink-Jet process, in which they may be used directly in the form of colored inks, or by the dye diffusion transfer process, in which they are released image-wise from corresponding dye-releasers in the course of development and transferred to a dye-absorbent layer.
    Type: Grant
    Filed: March 27, 1984
    Date of Patent: June 18, 1985
    Assignee: Agfa-Gevaert Aktiengesellschaft
    Inventors: Gunther Schenk, Peter Bergthaller, Holger Heidenreich, Gerhard Wolfrum
  • Patent number: 4521506
    Abstract: Azo dyes corresponding to the formula (I): ##STR1## wherein R.sup.1 represents a releasable group, R.sup.2 represents H, halogen or sulphonyl, R.sup.3 and R.sup.4 represent H or groups not capable of chelate formation, and Q represents a group for completing a phenyl or naphthyl group,combine with nickel ions to form stable azo dye-metal complexes which have advantageous spectral properties. They are therefore particularly suitable for the production of highly light-fast magenta images, e.g. by the ink jet process, in which they may be used directly in the form of colored inks, or by the dye diffusion transfer process, in which they are released imagewise from suitable dye-releasers in the course of development and transferred to a dye-receptive layer.
    Type: Grant
    Filed: June 5, 1984
    Date of Patent: June 4, 1985
    Assignee: Agfa-Gevaert Aktiengesellschaft
    Inventors: Rudolf Stolzenburg, Peter Bergthaller, Gerhard Wolfrum, Jurgen Strauss
  • Patent number: 4520095
    Abstract: A photographic light-sensitive element having at least one light-sensitive silver halide layer and a dye image forming non-diffusible material which, upon a redox reaction under alkaline conditions releases a diffusible cyan dye or precursor thereof wherein said material is ##STR1## wherein Car represents a carrier component having at least on Ball group as a part thereof which alone or together with other such groups in said Car renders said compound non-diffusible during development in alkaline processing solution, said Car being capable of releasing from said compound a diffusible dye or the precursor thereof as the result of a redox reaction under alkaline conditions:R represents a hydrogen atom or an alkyl group having from 1 to 3 carbon atoms;R.sup.1 is ##STR2## wherein R.sup.2 and R.sup.3 are independently selected from a hydrogen atom, or an alkyl, a cycloalkyl or an aryl group having from 1 to 30 carbon atoms, and R.sup.2 and R.sup.
    Type: Grant
    Filed: October 4, 1983
    Date of Patent: May 28, 1985
    Assignee: Konishiroku Photo Industry Co., Ltd.
    Inventors: Tatsuhiko Kobayashi, Satoru Ikeuchi, Kazumasa Watanabe, Shunji Suginaka
  • Patent number: 4517286
    Abstract: A color diffusion transfer process light-sensitive element is disclosed. The element is comprised of a support having coated thereon a light-sensitive silver halide emulsion layer which is associated with a dye image-providing compound. The dye image-providing compound is dispersed in a copresent state with a compound represented by the general formula (I): ##STR1## wherein the substituents within the general formula (I) are defined within the specification. The element has improved maximum image density and by utilizing the compound of the general formula (I) it is possible to obtain improved dispersion stability.
    Type: Grant
    Filed: December 2, 1983
    Date of Patent: May 14, 1985
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Yasuhiro Noguchi, Masakazu Morigaki
  • Patent number: 4493885
    Abstract: A color photographic element for the diffusion transfer process comprising a support having thereon at least one photosensitive silver halide emulsion layer, the silver halide emulsion layer having associated therewith a dye releasing redox compound or a dye releasing coupler and the dye releasing redox compound or the dye releasing coupler releasing a diffusible metal complex having coordinated therewith a dye or a dye precursor and a cyclic or straight or branched chain multidenate ligand by reaction with the oxidation product of a developing agent.
    Type: Grant
    Filed: May 10, 1983
    Date of Patent: January 15, 1985
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Shinsaku Fujita, Yukio Maekawa, Shigetoshi Ono
  • Patent number: 4483915
    Abstract: A photographic silver halide material comprises a shifted dye compound capable of releasing a dye moiety, characterized in that said compound corresponds in reduced state to general formula (1) and in oxidized state to general formula (2):A.sup.1 --L--P (1)A.sup.2 --L--P (2)wherein:A.sup.1 represents a hydroquinonyl group including a substituted hydroquinonyl group, or such group forming part of a fused ring system,A.sup.2 represents a quinonyl group including a substituted quinonyl group, or such group forming part of a fused ring system,L represents a bivalent group which undergoes a cleavage under hydrolytic alkaline conditions when the compound is in reduced state corresponding to formula (1),P represents an organic dye moiety incorporating an azo chromophoric group --N.dbd.
    Type: Grant
    Filed: November 29, 1983
    Date of Patent: November 20, 1984
    Assignee: Agfa-Gevaert, N. V.
    Inventors: Christian C. Van de Sande, Armand M. Van den Bergh, Wilhelmus Janssens
  • Patent number: 4481278
    Abstract: Novel chrome complexed azo and azomethine yellow dye developers which include a substantially colorless symmetrical ligand. Also disclosed are photographic products and processes which utilize the dye developers.
    Type: Grant
    Filed: October 29, 1982
    Date of Patent: November 6, 1984
    Assignee: Polaroid Corporation
    Inventors: Patrick F. King, Stephen G. Stroud
  • Patent number: 4473632
    Abstract: A heat-developable color photographic material is disclosed. The material is comprised of a support having thereon a light-sensitive silver halide, a hydrophilic binder and a dye releasing redox compound represented by the general formula (I): ##STR1## the substituents within the general formula (I) are disclosed within the specification. The heat-developable color photographic material can easily provide a clear and stable color image by imagewise exposure to light and a heat-development procedure. A method of forming a color image using the heat-developable color photographic material is also disclosed.
    Type: Grant
    Filed: December 28, 1983
    Date of Patent: September 25, 1984
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Hiroshi Kitaguchi, Kozo Sato, Shinsaku Fujita, Hideki Naito
  • Patent number: 4473631
    Abstract: A heat-developable color photographic material is disclosed. The material is comprised of a support having thereon at least a light-sensitive silver halide, a hydrophilic binder, a dye releasing compound reductive and capable of releasing a hydrophilic dye and a compound represented by the following general formula (A): ##STR1## wherein A.sub.1, A.sub.2, A.sub.3, and A.sub.4, which may be the same or different, each represents a hydrogen atom or a substituent selected from an alkyl group, a substituted alkyl group, a cycloalkyl group, an aralkyl group, an aryl group, a substituted aryl group and a heterocyclic group, or A.sub.1 and A.sub.2 or A.sub.3 and A.sub.4 may combine with each other to form a ring.The heat-developable color photographic material can easily provide in a short time a clear and stable color image having a high color density and low fog by imagewise exposure and heat development procedure.
    Type: Grant
    Filed: November 4, 1983
    Date of Patent: September 25, 1984
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Hiroyuki Hirai, Hideki Naito, Hiroshi Hara, Kozo Sato
  • Patent number: 4468452
    Abstract: A color diffusion transfer photographic element comprising a support having provided thereon a layer containing a dye-providing material associated with a light-sensitive silver halide emulsion, wherein said dye-providing material is a metal chelate compound represented by the following general formula (I) or (II): ##STR1## wherein M.sup.I represents a monovalent, divalent, or trivalent cation; X represents a monovalent, divalent, or trivalent anion; Z and Z.sup.2 each represents an aromatic carbon ring nucleus or heterocyclic ring nucleus having 5 to 7 carbon atoms; G represents a chelating group; Z.sup.1 represents an aromatic carbon ring nucleus or heterocyclic nucleus composed of 5 to 7 atoms; said nucleus having (a) a nitrogen atom, or (b) a carbon atom bonded to a chelating group at the position adjacent to the position bonded to the azo group; Z.sup.3 represents an electron attractive group; Z.sup.
    Type: Grant
    Filed: March 24, 1983
    Date of Patent: August 28, 1984
    Assignee: Fuji Photo Film Company, Limited
    Inventors: Shigeru Nakamura, Shigetoshi Ono, Seiji Suzuki, Hirohisa Suzuki
  • Patent number: 4461827
    Abstract: Metal complexes, particularly copper and nickel complexes, of azo dyes corresponding to formula suitable for use as magenta-colored image dyes for the production of colored images by the dye diffusion transfer process. The dyes are linked (in non-metallized form) to a carrier radical provided with a ballast group as so-called color-providing compounds which are associated with a photosensitive silver halide emulsion layer. During development, the metallizable dyes are released imagewise and, after diffusion into an image-receiving layer, are converted into the corresponding metal complexes. ##STR1## In formula II, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 represent H, F, Cl, Br, --CN, --NO.sub.2, --CF.sub.3, --OCH.sub.3, --SCF.sub.3, alkyl, alkoxy, alkylthio, acylamino, alkyl sulphonyl, aryl sulphonyl, --CO--X or --SO.sub.2 Y; or two adjacent radicals from the group of radicals R.sup.1 to R.sup.4 together represent a fused benzene ring;R.sup.
    Type: Grant
    Filed: January 3, 1983
    Date of Patent: July 24, 1984
    Assignee: AGFA-Gevaert Aktiengesellschaft
    Inventors: Peter Bergthaller, Gunther Schenk, Gerhard Wolfrum
  • Patent number: 4458012
    Abstract: Disclosed is a light-sensitive silver halide color photographic material having at least one light-sensitive silver halide emulsion layer on a support, characterized in that said light-sensitive silver halide emulsion layer contains a cyan coupler represented by formula [I] shown below, and said light-sensitive silver halide emulsion layer and/or a layer contiguous to said light-sensitive silver halide emulsion layer contains a colored cyan coupler represented by the formula [II]: ##STR1## wherein X, R.sub.1 and R.sub.2 are as defined in the specification; ##STR2## wherein (Coup--).sub.c, L, Q.sub.1, Q.sub.2, M, j, and G are as defined in the specification.
    Type: Grant
    Filed: February 22, 1983
    Date of Patent: July 3, 1984
    Assignee: Konishiroku Photo Industry Co., Ltd.
    Inventors: Kenji Ito, Satoru Shimba, Yasuo Tsuda, Hiroshi Sugita
  • Patent number: 4456668
    Abstract: Azo dyes of the formula ##STR1## in which X.sub.1 and X.sub.2 independently of one another are alkyl, cycloalkyl, alkenyl, aryl or aralkyl, Y.sub.1 is hydrogen or alkyl, Y.sub.2 is hydrogen, alkyl, alkenyl or aryl or together with Y.sub.1 stands for the atoms required to complete a ring, Z.sub.1 is hydrogen, alkyl, alkenyl, alkoxy, aryl, aryloxy, alkylmercapto, arylmercapto, halogen, cyano, carbalkoxy or stands for the atoms which together with Y.sub.1 form a ring, and D.sub.1 is the radical of a heterocyclic azo component such as a thienyl, thiazolyl, benzthiazolyl, pyrazolyl or imidazolyl radical, or is phenyl optionally substituted by alkyl, cycloalkyl, alkoxy, alkenyl, electronegative substituents such as halogen, cyano, nitro or carboxylic acyl, alkyl- or phenylsulfone or N-alkyl or N,N-dialkyl-substituted sulfonamido, can be used as image dyes in photographic silver dye-bleach materials, or for dyeing textile materials.
    Type: Grant
    Filed: September 29, 1982
    Date of Patent: June 26, 1984
    Assignee: Ciba Geigy AG
    Inventors: John Lenoir, Gerald Jan
  • Patent number: 4444867
    Abstract: Sulfilimine compounds of formula I ##STR1## wherein X is the integrating residue of a photographically active compound H.sub.2 N--A--X andA is a linking member between X and N consisting of a benzene ring having at least two electron-attracting groupsare suitable compounds for photographic recording materials. The compounds can be split reductively to release the photographically active compound. Where the photographically active compound is a dye or dye precursor the sulfilimine compounds are suitable dye releasers for color diffusion transfer processes.
    Type: Grant
    Filed: April 18, 1983
    Date of Patent: April 24, 1984
    Assignee: Agfa-Gevaert Aktiengesellschaft
    Inventor: Hans-Heinrich Credner
  • Patent number: 4439513
    Abstract: A color photographic light-sensitive material is disclosed. The material is comprised of a support having thereon a layer containing at least one kind of dye releasing 2-acylamino-1-naphthol derivative represented by the following general formula (I):R--L--D (I)wherein R represents a reducing group represented by the following general formula (II): ##STR1## wherein the substituents R.sub.1 -R.sub.8 are defined within the application; L represents a connecting group between R and D wherein specific examples of L are defined in the specification; and D represents a dye or a precursor of a dye. The dye releasing 2-acylamino-1-naphthol derivative of the present invention has a high dye releasing efficiency when it is oxidized. The derivative of the invention can release a dye having a good diffusibility and can provide a high dye transfer density and thus it is suitable to use as a coloring material in a color photographic light-sensitive material of diffusion transfer type.
    Type: Grant
    Filed: December 28, 1982
    Date of Patent: March 27, 1984
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kozo Sato, Shinsaku Fujita, Hideki Naito, Hiroshi Hara
  • Patent number: 4431728
    Abstract: There is disclosed a silver halide photographic light-sensitive material which comprises a support, a combination of an unfogged surface latent image type silver halide photographic emulsion and a material which is non-diffusible under alkali conditions and which is capable of releasing a diffusible development inhibitor or a precursor thereof as a result of cross oxidation with an oxidized product of a photographic developing agent; and a combination of an internal latent image type silver halide photographic emulsion whose silver halide grains contain therein, prior to development, fog nuclei and a dye image-forming material which is initially non-diffusible under alkaline conditions but which is capable of releasing a diffusible dye or a precursor thereof as a result of being oxidized by the oxidized product of said photographic developing agent.
    Type: Grant
    Filed: June 9, 1982
    Date of Patent: February 14, 1984
    Assignee: Konishiroku Photo Industry Co., Ltd.
    Inventors: Takao Abe, Tatsuhiko Kobayashi
  • Patent number: 4430425
    Abstract: Color photographic silver halide material which contains in at least one coupler containing silver halide emulsion layer or in a layer adjacent thereto(a) a hydroquinone of the formula ##STR1## wherein p is 1 or 2 and q is 0 or 1, provided that p+q is 1 or 2, R is a radical of the formula ##STR2## wherein Q is selected from the residues (1) --COZR.sub.4, wherein Z is O or NR.sub.5, and R.sub.4 is hydrogen, alkyl optionally interrupted by oxygen, cycloalkyl, alkenyl, aryl, aralkyl or a heterocyclic ring, and R.sub.5 is hydrogen or alkyl or together with R.sub.4 and the nitrogen atom to which they are bonded form a heterocyclic ring,(2) --OX, wherein X is R.sub.5 or --COR.sub.7, wherein R.sub.7 is hydrogen, alkyl cycloalkyl, alkenyl, aryl or aralkyl,(3) --NR.sub.8 R.sub.9, wherein R.sub.8 is hydrogen or alkyl, and R.sub.9 is hydrogen, alkyl or --COR.sub.7, or R.sub.8 and R.sub.9 together with the nitrogen atom to which they are bonded form a ring,(4) --P(O)(OR.sub.10 ')([O].sub.x R.sub.
    Type: Grant
    Filed: June 18, 1982
    Date of Patent: February 7, 1984
    Assignee: Ciba-Geigy AG
    Inventor: David G. Leppard
  • Patent number: 4427763
    Abstract: A color photographic recording material, in which a precursor compound for a yellow mask coupler is contained in a green-sensitive layer or in a layer adjacent thereto and in which a blue-sensitive layer is arranged between this layer and the layer support, permits very good sharpness with satisfactory speed.
    Type: Grant
    Filed: August 30, 1982
    Date of Patent: January 24, 1984
    Assignee: Agfa-Gevaert Aktiengesellschaft
    Inventors: Joachim W. Lohmann, Gunter Renner, Wolfgang Sauerteig
  • Patent number: 4425422
    Abstract: A method for the formation of a color photographic image comprising exposure and development of a photographic element, said photographic element comprising at least one silver halide emulsion layer, a compound capable of releasing a diffusible azo dye compound during development, and at least one mordant layer arranged on a support. The color image formation is effected by the reaction of multivalent metallic ions with an azo dye compound having the formula: ##STR1## wherein G.sup.1 is an alkoxy or a thioalkoxy metallic chelating group; G.sup.2 is a metallic chelating group in which an oxygen atom is involved in the chelate formation; and Z.sup.1 and Z.sup.2 each is a group of atoms necessary to form an aromatic carbocyclic ring or a heterocyclic ring. The azo dye compound and the metallic ions form a metal complex by coordination of the azo group and the G.sup.1 and G.sup.2 groups of the azo dye compound with the multivalent metallic ions.
    Type: Grant
    Filed: May 6, 1982
    Date of Patent: January 10, 1984
    Assignee: Konishiroku Photo Industry Co., Ltd.
    Inventors: Tawara Komamura, Jiro Takahashi, Ryuichiro Kobayashi
  • Patent number: 4420550
    Abstract: Photographic elements, diffusion transfer assemblages, coordination complexes and processes are described which employ a novel nondiffusible compound capable of releasing at least one diffusible magenta dye moiety comprising a 4-(2-heterocyclylazo)phenol having a heterocyclic ring fused thereto, the compound having the formula: ##STR1## wherein: (a) X represents the atoms necessary to complete a 5- or 6-membered heterocyclic ring;(b) Y represents the atoms necessary to complete a 5- or 6-membered heterocyclic fused ring;(c) CAR represents a ballasted carrier moiety capable of releasing the diffusible magenta dye moiety as a function of development of a silver halide emulsion layer under alkaline conditions;(d) R represents a hydroxy group, a salt thereof, or a hydrolyzable precursor thereof, or CAR which is linked to the dye moiety through an oxygen atom thereon; and(e) n is 0, 1 or 2, with the proviso that when n is 0, then R is CAR which is linked to the dye moiety through an oxygen atom thereon.
    Type: Grant
    Filed: January 17, 1983
    Date of Patent: December 13, 1983
    Assignee: Eastman Kodak Company
    Inventors: Steven Evans, James K. Elwood
  • Patent number: 4419435
    Abstract: Photographic elements, diffusion transfer assemblages, coordination complexes and processes are described which employ a novel nondiffusible compound capable of releasing at least one diffusible cyan dye moiety comprising a 6-heterocyclylazo-3-pyridinol, the compound having the formula: ##STR1## wherein: (a) Y represents the atoms necessary to complete a 5- or 6-membered aromatic heterocyclic fused ring;(b) CAR represents a ballasted carrier moiety capable of releasing the diffusible cyan dye moiety as a function of development of a silver halide emulsion layer under alkaline conditions;(c) R represents a hydroxy group, a salt thereof, or a hydrolyzable precursor thereof, or CAR which is linked to the dye moiety through an oxygen atom thereon; and(d) n is 0, 1 or 2 with the proviso that when n is 0, then R is CAR which is linked to the dye moiety through an oxygen atom thereon.
    Type: Grant
    Filed: January 17, 1983
    Date of Patent: December 6, 1983
    Assignee: Eastman Kodak Company
    Inventors: James A. Reczek, James K. Elwood
  • Patent number: 4418143
    Abstract: Azo dyes of formula II are released on development from dye releasers which are associated with a light-sensitive silver halide emulsion layer. The azo dyes are chelatable and form with metal ions blue or cyan dye-metal-complex image dyes. ##STR1## In the formula A.sup.1 and A.sup.2 represent electronegative substituents whose meta-sigma values .sigma..sub.m (according to D. H. McDaniel and H. C. Brown in J. Org. Chem. 23, 420 et seq (1958) conform to at least one of the following three relationships:1. .sigma..sub.m (A.sup.1), .sigma..sub.m (A.sup.2) +0.332. .sigma..sub.m (A.sup.1) +.sigma..sub.m (A.sup.2) +0.75;3. .sigma..sub.m (A.sup.1) +0.33 and A.sup.2 represents--SO.sub.2.sup.XX represents H, --OH, --NH.sub.
    Type: Grant
    Filed: February 22, 1982
    Date of Patent: November 29, 1983
    Assignee: Agfa-Gevaert Aktiengesellschaft
    Inventors: Peter Bergthaller, Gunther Schenk, Gerhard Wolfrum, Hans-Volker Runzheimer, Holger Heidenreich
  • Patent number: 4416979
    Abstract: A photographic light-sensitive element for a color diffusion transfer process which has a silver halide emulsion layer and also employs a nondiffusible cyan dye releasing compound. The compound is capable of releasing a diffusible metallic complex which forms an azo dye under alkaline conditions as a function of the development of the silver halide in said silver halide emulsion layer.
    Type: Grant
    Filed: May 6, 1982
    Date of Patent: November 22, 1983
    Assignee: Konishiroku Photo Industry Co., Ltd.
    Inventors: Jiro Takahashi, Tawara Komamura, Ryuichiro Kobayashi
  • Patent number: 4409143
    Abstract: Azo dyes of the formula in which X.sub.1 and X.sub.2 independently of one another are alkyl, cycloalkyl, alkenyl, aryl or aralkyl, Y.sub.1 is hydrogen or alkyl, Y.sub.2 is hydrogen, alkyl, alkenyl or aryl or together with Y.sub.1 stands for the atoms required to complete a ring, Z.sub.1 is hydrogen, alkyl, alkenyl, alkoxy, aryl, aryloxy, alkylmercapto, arylmercapto, halogen, cyano, carbalkoxy or stands for the atoms which together with Y.sub.1 form a ring, and D.sub.1 is the radical of a heterocyclic azo component such as a thienyl, thiazolyl, benzthiazolyl, pyrazolyl or imidazolyl radical, or is phenyl optionally substituted by alkyl, cycloalkyl, alkoxy, alkenyl, electronegative substituents such as halogen, cyano, nitro or carboxylic acid, alkyl- or phenylsulfone or N-alkyl or N,N-dialkyl-substituted sulfonamido, can be used as image dyes in photographic silver dye-bleach materials, or for dyeing textile materials.
    Type: Grant
    Filed: April 28, 1981
    Date of Patent: October 11, 1983
    Assignee: Ciba-Geigy AG
    Inventors: John Lenoir, Gerald Jan
  • Patent number: 4407931
    Abstract: Photographic elements, diffusion transfer assemblages, coordination complexes and processes are described which employ a novel nondiffusible compound having a releasable yellow dye moiety or precursor thereof, the compound having the formula: ##STR1## wherein: (a) X represents the atoms necessary to complete a 5- or 6-membered aromatic heterocyclic fused ring;(b) Z represents alkyl, substituted alkyl, aryl or substituted aryl;(c) R represents CN or J--L;(d) J represents a bivalent ##STR2## group; (e) L represents alkyl, substituted alkyl, aryl, substituted aryl, or can be taken together with Z to complete a carbonyl-containing 5- or 6-membered heterocyclic or carbocyclic ring;(f) Z.sup.
    Type: Grant
    Filed: June 28, 1982
    Date of Patent: October 4, 1983
    Assignee: Eastman Kodak Company
    Inventor: Steven Evans
  • Patent number: 4396710
    Abstract: Cyan images may be prepared by the dye diffusion transfer process, using dye-releasers which on development release diffusible dyes capable of forming light-fast cyan metal-dye-complexes particularly with copper or nickel ions. As also the dye-releasers are capable of complexation, cyan images can be prepared not only from the released dyes but also from the dye-releasers ("retained image"). Released dyes and dye-releasers of the present invention contain a chromophor of the following formula: ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4, which may be the same or different, each represents --H, --F, --Cl, --Br, --CN, --NO.sub.2, --CF.sub.3, --OCF.sub.3, --SCF.sub.3, alkyl, alkoxy, alkylthio, acylamino, alkylsulfonyl, arylsulfonyl, --CO--X or --SO.sub.2 --Y or two adjacent groups R.sup.1 -R.sup.4 together constitute a condensed benzene ring which may contain further substituents;R.sup.5 represents hydrogen or a substituent having an electron donor character;R.sup.
    Type: Grant
    Filed: April 12, 1982
    Date of Patent: August 2, 1983
    Assignee: Afga-Gevaert Aktiengesellschaft
    Inventors: Peter Bergthaller, Gunther Schenk, Gerhard Wolfrum, Hans-Volker Runzheimer
  • Patent number: 4393132
    Abstract: For the production of light-fast yellow images (transfer images and retained images) by the dye diffusion transfer process dye-releasers are useful which on development release diffusible azo dyes which can complex with nickel or copper ions and which in one of their tautomeric forms correspond to the general formula: ##STR1## wherein R.sup.1 represents alkyl, alkenyl or cycloalkyl having up to 8 carbon atoms,Z represents a radical required for completing a benzene or naphthalene ring; andL represents a substituent having a group which results from the splitting from a carrier radical.
    Type: Grant
    Filed: April 23, 1982
    Date of Patent: July 12, 1983
    Assignee: Agfa-Gevaert Aktiengesellschaft
    Inventors: Gunther Schenk, Peter Bergthaller, Gerhard Wolfrum, Rudolf Stolzenburg
  • Patent number: 4386150
    Abstract: Diffusion transfer photographic color processes and products are described utilizing novel image dye-providing materials which provide image dyes having the chromophoric system represented by the formula ##STR1## wherein X is ##STR2## or --SO.sub.2 --R.sub.1 ; Z is H, alkyl or aryl; R is H, alkyl or aryl; DYE is any dye moiety; R.sub.1 is H, alkyl, aryl, --NH.sub.2, --NHR.sub.2, --N(R.sub.2).sub.2 or --OR.sub.2 ; R.sub.2 is H, alkyl or aryl; and m is 1 or 2. The image dye providing material includes a diffusion control moiety such as a hydroquinonyl group or a precursor thereof and may be diffusible or nondiffusible as a function of the diffusion control moiety.
    Type: Grant
    Filed: December 18, 1981
    Date of Patent: May 31, 1983
    Assignee: Polaroid Corporation
    Inventors: Stephen R. Herchen, Gary N. Widiger
  • Patent number: 4379819
    Abstract: A color-photographic recording material for the silver dye bleach process, which contains oil-soluble azo dyes of the formula ##STR1## in which R.sub.1 is hydrogen, alkyl, alkoxy, alkenyl, acyl, carbalkoxy, acylamino, carbamide, sulfonamide, alkylsulfone, arylsulfone, aryloxy, arylsulfonic acid ester, hydroxyl, cyano, nitro or halogen, R.sub.2 is hydrogen, alkyl, alkoxy, carbalkoxy, carbamide, sulfonamide, alkylsulfone, arylsulfone, aryloxy, cyano, nitro or halogen, R.sub.3 is hydrogen, alkyl, alkoxy, phenoxy, sulfonamide, alkylsulfone, sulfonic acid ester, cyano, nitro, halogen, carbalkoxy, carbamide or phosphoric acid diester, R.sub.4 is hydrogen, alkyl, alkoxy, carbalkoxy, carbamide, sulfonamide, acylamino, alkylsulfone, arylsulfone, hydroxyl, cyano, nitro or halogen, R.sub.5 is hydrogen, alkyl or carbalkoxy, X.sub.1 is hydrogen, alkyl, alkoxy, acylamino, alkylsulfonamide or hydroxyl, Y.sub.
    Type: Grant
    Filed: April 28, 1981
    Date of Patent: April 12, 1983
    Assignee: Ciba-Geigy AG
    Inventors: John Lenoir, Gerald Jan, Mario Fryberg
  • Patent number: 4374923
    Abstract: A direct positive silver halide photographic light-sensitive material is described comprising a support having coated thereon at least one light-sensitive silver halide photographic emulsion layer, wherein at least one layer of the light-sensitive silver halide photographic emulsion layers and other hydrophilic colloid layers contains a compound represented by formula (I) ##STR1## wherein R.sup.1 and R.sup.2 can each represent a hydrogen atom, an aliphatic group, an aromatic group, or a heterocyclic group; R.sup.3 represents a hydrogen atom or an aliphatic group; R.sup.4 represents a hydrogen atom, an aliphatic group, or an aromatic group; and X represents a divalent aromatic group.
    Type: Grant
    Filed: November 17, 1981
    Date of Patent: February 22, 1983
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Shigeo Hirano, Tadao Sugimoto, Nobuyuki Tsujino
  • Patent number: 4369243
    Abstract: Sulfilimine compounds of formula I ##STR1## in which R.sup.3 is the residue of a diffusible photographically active compound can be split reductively to release the residue together with a group --SO.sub.2 --NH.sub.2. When R.sup.3 represents the radical of a dye or dye precursor the sulfilimines are useful as color providing compounds in dye diffusion transfer processes.
    Type: Grant
    Filed: March 6, 1981
    Date of Patent: January 18, 1983
    Assignee: Agfa-Gevaert Aktiengesellschaft
    Inventors: Hans-Heinrich Credner, Wolfgang Lassig, Karl-Wilhelm Schranz
  • Patent number: 4368260
    Abstract: A photographic light-sensitive element which comprises on a support a light-sensitive silver halide emulsion layer and having associated therewith a non-diffusible compound capable of, under alkaline condition, releasing a diffusible azo dye, said compound having the formula (1), ##STR1## wherein X represents a group of atoms necessary to complete a naphthalene ring or a benzene ring, G.sup.1 represents a hydroxy group, a salt thereof or a hydrolyzable precursor thereof, G.sup.2 represents a carboxy group, a salt thereof or a hydrolyzable precursor thereof, a hydroxy group, a salt thereof or a hydrolyzable precursor thereof, R.sup.1 is a hydrogen atom, an alkyl group or an aryl group, R.sup.2 is a hydrogen atom, an alkyl group or an aryl group, R.sup.2 represents a hydrogen atom, a halogen atom, an alkyl group, a carboxy group, a carbamoyl group or an amino group, each of which group may be substituted, R.sup.
    Type: Grant
    Filed: December 23, 1981
    Date of Patent: January 11, 1983
    Assignee: Konishiroku Photo Industry Co., Ltd.
    Inventors: Tawara Komamura, Jiro Takahashi, Ryuichiro Kobayashi
  • Patent number: 4368251
    Abstract: A photographic light-sensitive sheet containing at least one light-sensitive silver halide emulsion layer, with at least one of said emulsion layers being associated with a compound represented by the following general formula (I) or (II): ##STR1## wherein B.sub.1 represents a hydrogen atom or an alkyl group, etc.; B.sub.2 represents a hydrogen atom, an alkyl group, an acyl group, an alkylsulfonyl group, etc.; D.sub.1 and D.sub.2 may be the same or different and each represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, etc., provided that D.sub.2 does not represent an alkoxy-substituted alkoxy group; E.sub.1 and E.sub.2 may be the same or different and each represents a hydrogen atom, a cyano group, halogen atom, an alkyl group, an alkoxy group, a sulfonamido group, a carbonamido group, a sulfamoyl group, a carbamoyl group, etc., provided that E.sub.2 does not represent an alkoxy-substituted alkoxy group; R.sup.1 represents an alkylene group containing two or more carbon atoms; R.sup.
    Type: Grant
    Filed: April 16, 1980
    Date of Patent: January 11, 1983
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Shigetoshi Ono, Shinsaku Fujita
  • Patent number: 4367278
    Abstract: A color photographic light-sensitive material comprising a support having thereon at least one light-sensitive silver halide emulsion layer having associated therewith a compound encompassed by one of two general formulae which are specifically disclosed. The compound associated with the silver halide emulsion layer is an azo dye image-forming compound which provides a yellow dye image having excellent transferability and light fastness. The azo dye image forming compound is particularly suitable for use in a photographic material for a color diffusion transfer process. The disclosed material is capable of providing a transferred dye image with a high maximum image density (D.sub.max), a low minimum background density (D.sub.min), a good gradation and excellent color hue.
    Type: Grant
    Filed: May 6, 1981
    Date of Patent: January 4, 1983
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Tooru Harada, Yasuhiro Noguchi
  • Patent number: 4363865
    Abstract: Imidomethyl blocked photographic image dyes and dye releasing compounds are useful in photographic elements, film units and processes. The blocked photographic dyes and dye releasing compounds have the structures: ##STR1## wherein: J represents ##STR2## X represents the atoms to complete at least one 5- or 6-membered ring; R represents hydrogen, alkyl of 1 to 4 carbon atoms or aryl of 6 to 12 carbon atoms;Q represents ##STR3## --Q--DYE represents the residue of a diffusible photographic dye; and CAR is a ballasted carrier moiety from which the dye moiety is released as a function of silver halide development.
    Type: Grant
    Filed: March 4, 1981
    Date of Patent: December 14, 1982
    Assignee: Eastman Kodak Company
    Inventors: James A. Reczek, Thomas R. Welter
  • Patent number: 4358525
    Abstract: Photographically useful compounds such as photographic reagents and photographic dyes are blocked with a grouping which, under alkaline conditions, is cleaved from the compound by an intramolecular nucleophilic displacement reaction. The compounds are resistant to unblocking under storage conditions, but are uniformly unblocked under conditions encountered during photographic processing.
    Type: Grant
    Filed: August 12, 1981
    Date of Patent: November 9, 1982
    Assignee: Eastman Kodak Company
    Inventors: Jared B. Mooberry, William C. Archie, Jr.
  • Patent number: 4358532
    Abstract: A photographic element containing a compound represented by formula (I) ##STR1## wherein G represents --OR.sup.1 or --NHR.sup.2, R.sup.1 represents hydrogen or a hydrolyzable moiety, R.sup.2 represents hydrogen or an alkyl group containing from 1 to 50 carbon atoms, Z represents a photographically useful group, A represents an atomic group forming an aromatic ring, Ball represents an organic immobilizing group on the aromatic ring, which cntains from 8 to 50 carbon atoms, m represents an integer of 1 or 2, X represents a divalent organic group, Nu represents a nucleophilic group, and n represents an integer of 1 or 2, and X with the nucleophilic group Nu is capable of forming a 5- to 12-membered ring by oxidation having an electrophilic center at the carbon atom substituted by the --NHSO.sub.2 Z group.
    Type: Grant
    Filed: July 15, 1981
    Date of Patent: November 9, 1982
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Koichi Koyama, Shinsaku Fujita
  • Patent number: 4358526
    Abstract: A photographic light-sensitive sheet for the color diffusion transfer process which comprises a support having thereon at least one light-sensitive silver halide emulsion layer having associated therewith a compound represented by the following general formula (I): ##STR1## wherein X.sup.1 represents --J--NR.sup.2 -- or --NR.sup.2 --J-- wherein R.sup.2 represents a hydrogen atom or an alkyl group, and J represents --SO.sub.2 -- or --CO--; R.sup.1 represents an alkyl group; X.sup.2 represents --R.sup.3 --L).sub.k (R.sup.4).sub.e -- wherein R.sup.3 and R.sup.4, which may be the same or different, each represents an alkylene group, a substituted alkylene group, a phenylene group or a substituted phenylene group, L represents --O--, --CO--, --SO.sub.2 NH--, --CONH--, --NHSO.sub.2 --, --NHCO--, --SO.sub.2 -- or --SO--, k represents 0 or 1, and e represents 1 when k is 1, or 1 or 0 when k is 0, provided that when X.sup.2 bonds to X.sup.1, X.sup.1 bonds to R.sup.
    Type: Grant
    Filed: August 18, 1981
    Date of Patent: November 9, 1982
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Shinsaku Fujita, Isamu Itoh, Shigetoshi Ono, Tooru Harada, Yoshinobu Yoshida
  • Patent number: 4357412
    Abstract: Photographic elements, diffusion transfer assemblages and processes are described which employ a novel nondiffusible compound having a releasable, bridged, azoaminophenol magenta dye moiety or precursor thereof having the formula: ##STR1## wherein: (a) R represents hydrogen, a hydrolyzable moiety or CAR;(b) R.sup.1 represents hydrogen;(c) R.sup.2 represents an alkyl group of 1 to about 6 carbon atoms or CAR; or R.sup.1 and R.sup.2 represent an alkylene group which can be taken together with the atoms to which they are attached to complete a 5- or 6-membered heterocyclic ring;(d) R.sup.3 represents an alkyl group of 1 to about 6 carbon atoms or CAR;(e) R.sup.4 represents hydrogen; or R.sup.3 and R.sup.
    Type: Grant
    Filed: July 13, 1981
    Date of Patent: November 2, 1982
    Assignee: Eastman Kodak Company
    Inventors: Richard B. Anderson, Norman W. Kalenda
  • Patent number: 4357411
    Abstract: Photographic elements, diffusion transfer assemblages and processes are described which employ a novel nondiffusible compound having a releasable, 2-(2-pyridylazo)-4,5-bis(tertiary amino)phenol black dye moiety or precursor thereof, such as: ##STR1## wherein: (a) R represents hydrogen, a hydrolyzable moiety or CAR;(b) R.sup.1 and R.sup.2 each independently represents an alkyl group of 1 to about 6 carbon atoms, CAR, or can be taken together with the nitrogen atom to which they are attached to complete a 5- or 6-membered heterocyclic ring;(c) R.sup.3 and R.sup.4 each independently represents an alkyl group of 1 to about 6 carbon atoms, CAR, or can be taken together with the nitrogen to which they are attached to complete a 5- or 6-membered heterocyclic ring;(d) CAR represents a ballasted carrier moiety capable of releasing the diffusible black dye moiety or precursor thereof under alkaline conditions; and(e) n is 0, 1 or 2, with the proviso that when n is 0, then at least one of R, R.sup.1, R.sup.2, R.sup.
    Type: Grant
    Filed: July 13, 1981
    Date of Patent: November 2, 1982
    Assignee: Eastman Kodak Company
    Inventor: Norman W. Kalenda
  • Patent number: 4357410
    Abstract: Photographic elements, diffusion transfer assemblages and processes are described which employ a novel nondiffusible compound having a releasable, pyridylazo(dialkylamino)phenol magenta dye moiety or precursor thereof, having the formula: ##STR1## wherein: (a) R represents hydrogen, a hydrolyzable moiety, or may be taken together with the NHSO.sub.2 group to which it is attached to form CAR;(b) R.sup.1 represents hydrogen, a hydrolyzable moiety or CAR;(c) R.sup.2 and R.sup.3 each independently represents hydrogen, CAR, an alkyl group of 1 to about 6 carbon atoms, or they can be taken together with the nitrogen to which they are attached to form a 5- or 6-membered heterocyclic ring, or one of R.sup.2 and R.sup.3 can be an aryl group having from 6 to about 10 carbon atoms; and(d) CAR represents a ballasted carrier moiety capable of releasing the diffusible magenta dye moiety or precursor thereof under alkaline conditions;with the proviso that at least one of R, R.sup.1, R.sup.2 and R.sup.3 is CAR.
    Type: Grant
    Filed: July 13, 1981
    Date of Patent: November 2, 1982
    Assignee: Eastman Kodak Company
    Inventors: Richard B. Anderson, Norman W. Kalenda
  • Patent number: 4346155
    Abstract: Photographic elements, diffusion transfer assemblages and processes are described which employ a novel nondiffusible compound having a releasable 6-arylazo-3-pyridinol magenta dye moiety or precursor thereof having the formula: ##STR1## wherein: (a) R represents hydroxy or amino;(b) R.sup.1 represents hydrogen, a hydrolyzable moiety or CAR;(c) G represents carboxy; a hydrolyzable ester or a sulfamoyl group;(d) CAR represents a ballasted carrier moiety capable of releasing the diffusible 6-arylazo-3-pyridinol dye moiety or precursor thereof under alkaline conditions; and(e) n is 0, 1 or 2, with the proviso that when n is 0, then R.sup.1 is CAR.
    Type: Grant
    Filed: August 24, 1981
    Date of Patent: August 24, 1982
    Assignee: Eastman Kodak Company
    Inventors: Derek D. Chapman, James A. Reczek
  • Patent number: 4346161
    Abstract: Photographic elements, diffusion transfer assemblages and processes are described which employ a novel nondiffusible compound having a releasable 6-(2-thienylazo)-3-pyridinol cyan dye moiety or precursor thereof, the compound containing:(a) in the 3-position of the thienylazo moiety a carboxy group, a salt thereof or a hydrolyzable precursor thereof; and(b) a ballasted carrier moiety which is capable of releasing the diffusible 6-(2-thienylazo)-3-pyridinol dye moiety or precursor thereof under alkaline conditions.
    Type: Grant
    Filed: April 29, 1981
    Date of Patent: August 24, 1982
    Assignee: Eastman Kodak Company
    Inventors: James J. Krutak, Robert J. Maleski, William H. Moore
  • Patent number: 4341858
    Abstract: Direct-positive photographic emulsions and elements which include internal-image silver halide grains, a nucleating amount of a hydrazine compound and a redox dye releaser are improved by the incorporation of a nucleation-promoting amount of a quinone oxidizing agent. Diffusion transfer images made from elements using these emulsions exhibit improved image discrimination and improved maximum density.
    Type: Grant
    Filed: May 1, 1981
    Date of Patent: July 27, 1982
    Assignee: Eastman Kodak Company
    Inventors: Eleanor Chaffee, Richard C. Tuites
  • Patent number: 4340661
    Abstract: A photographic light sensitive sheet for color diffusion transfer process which comprises a light sensitive silver halide emulsion layer associated with a novel azo dye-providing compound containing a --OR.sup.1 --O--R.sup.2 moiety as an indispensable substituent wherein R.sup.1 represents an alkylene group having 2 or more carbon atoms and R.sup.2 represents an alkyl group or a substituted alkyl group.
    Type: Grant
    Filed: April 3, 1980
    Date of Patent: July 20, 1982
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Shigetoshi Ono, Shinsaku Fujita
  • Patent number: 4336322
    Abstract: A color photographic light-sensitive material is described containing a dye-releasing redox compound having the following formula: ##STR1## wherein G represents a hydroxy group or a group providing a hydroxy group by hydrolysis;Col represents a dye or a dye precursor;R.sup.1 and R.sup.2, which may be the same or different, each represents an alkyl group or an aromatic group, and R.sup.1 and R.sup.2 together can form a ring;R.sup.3 represents hydrogen, an alkyl group or an aromatic group;R.sup.4 can represent an alkyl group or an aromatic group;R.sup.5 can represent an alkyl group, an alkoxy group, an alkylthio group, an arylthio group, a halogen atom or an acylamino group;n is 0, 1 or 2; andR.sup.4 and an R.sup.5 together can form a heterocyclic ring, R.sup.1 and R.sup.4 together can form a heterocyclic ring, R.sup.1 and an R.sup.5 together can form a ring, R.sup.1, R.sup.2 and R.sup.3 together can form an adamantyl ring, and the total number of carbon atoms of R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sub.n.
    Type: Grant
    Filed: July 18, 1980
    Date of Patent: June 22, 1982
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Shinsaku Fujita, Koichi Koyama, Yoshio Inagaki, Kokichi Waki
  • Patent number: 4310612
    Abstract: Photographically useful compounds such as photographic reagents and photographic dyes are blocked with a grouping which, under alkaline conditions, is cleaved from the compound by an intramolecular nucleophilic displacement reaction. The compounds are resistant to unblocking under storage conditions, but are uniformly unblocked under conditions encountered during photographic processing.
    Type: Grant
    Filed: October 10, 1978
    Date of Patent: January 12, 1982
    Assignee: Eastman Kodak Company
    Inventors: Jared B. Mooberry, William C. Archie, Jr.