Redox Cleavable Dye Or Dye Precursor Releaser Patents (Class 430/242)
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Patent number: 8358570Abstract: A method of drawing a pattern for magnetic transfer on a substrate, including the steps of rotating the substrate and scanning the substrate, by an electron beam, in a circumferential direction thereof, deflecting, using a deflection signal, the electron beam in a radial direction thereof, and switching irradiation of the electron beam on and off, so as to create the pattern of a plurality of dots.Type: GrantFiled: October 22, 2010Date of Patent: January 22, 2013Assignee: Fuji Electric Co., Ltd.Inventor: Hiroto Kikuchi
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Patent number: 6124084Abstract: A silver halide photographic light-sensitive material comprising a support having provided thereon a layer containing at least one cyan dye image forming compound represented by the following formula (1):(Dye-X).sub.1 --Y (1)wherein Dye, X, Y and q are as defined in the specification. The silver halide photographic light-sensitive material containing the cyan dye image forming compound according to the present invention provides a cyan color image excellent in fastness to light, humidity and heat.Type: GrantFiled: July 24, 1998Date of Patent: September 26, 2000Assignee: Fuji Photo Film Co., Ltd.Inventors: Keiichi Tateishi, Takayoshi Kamio, Tetsu Kamosaki, Yasuhiro Ishiwata, Hideaki Naruse
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Patent number: 5332654Abstract: A novel class of N-substituted triarylmethane sulfonamides is provided which undergo reversible oxidation into colored form and reversible reduction of the oxidized form into colorless form. Preferred embodiments comprise xanthene sulfonamides having N-aryl substituents, e.g., hydroquinone substituents. These compounds possess redox potentials ranging between about +200 to -500 millivolts and thus are useful as dyes for producing photographic, photothermographic, thermal, and pressure-induced images, as well as being useful as redox indicators in a wide variety of biological and chemical reactions.Type: GrantFiled: June 11, 1993Date of Patent: July 26, 1994Assignee: Polaroid CorporationInventors: Myron S. Simon, Marcis M. Kampe, David P. Waller
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Patent number: 5233028Abstract: (1) Dicyanoimidazole compound derivative represented by the formula [I] ##STR1## [R.sup.1, R.sup.2 : alkyl group, alkoxyalkyl group, hydroxyalkyl group, .beta.-cyanoethyl group, .beta.-chloroethyl group, aralkyl group, aryl group; X: hydrogen atom, lower alkoxy group, methyl group, halogen atom; Y: hydrogen atom, methyl group, methoxy group, formylamino group, alkylcarbonylamino group, alkylsulfonylamino group, alkoxycarbonylamino group; --Q--: --(CR.sub.2).sub.n --[n: integer of 1 to 12, R: hydrogen atom, alkyl group], ##STR2## --CH.dbd.CH--, --CH.sub.2 CH.dbd.CHCH.sub.2 --, --CH.sub.2 --CH.dbd.CH--]. (2) Magenta toner for color electrophotography containing at least one kind of the dicyanoimidazole compound derivative represented by the formula [I] as a coloring agent.(3) Colored resin and resin color filter containing at least one kind of the dicyanoimidazole compound derivative represented by the formula [I] in solution.Type: GrantFiled: February 1, 1991Date of Patent: August 3, 1993Assignee: Orient Chemical Industries, Ltd.Inventors: Masahiro Ohtsuka, Tohru Tamura
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Patent number: 4810615Abstract: Dye releasing compounds which release dyes corresponding to formula I ##STR1## wherein R.sup.1 denotes alkyl, aryl, arylamino, alkoxy or aryloxy,R.sup.2 denotes H or halogen,R.sup.3 denotes alkyl with 2-4 carbon atoms,R.sup.4 denotes H or one or more substituents such as alkyl, alkoxy, acylamino or halogen, including a substituent in the ortho-position to the group ##STR2## which together with R.sup.5 completes a cyclic amino group, R.sup.5 denotes alkyl with up to 4 carbon atoms or a group which together with a subsituent denoted by R.sup.4 or together with R.sup.6 completes a cyclic amino group, andR.sup.6 denotes alkyl with up to 4 carbon atoms or a group which together with R.sup.5 completes a cyclic amino groupare suitable for the production of light-stable cyan colour images.Type: GrantFiled: June 8, 1987Date of Patent: March 7, 1989Assignee: Agfa-Gevaert AktiengesellschaftInventors: Immo Boie, Hans Vetter, Kaspar Wingender
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Patent number: 4746592Abstract: Color correction of negative images resulting from diffusion transfer photographic recording materials is obtained through use of two dye image-providing compounds, each of which is capable of releasing a diffusible dye. One of the dye image-providing compounds releases a diffusible dye as a result of silver halide development whereas the other compound releases dye in areas where no development occurs.Type: GrantFiled: August 27, 1986Date of Patent: May 24, 1988Assignee: Eastman Kodak CompanyInventor: Kin K. Lum
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Patent number: 4600681Abstract: Metal complexes, particularly copper and nickel complexes of azo dyes corresponding to general formula (I) are suitable as color dyes for the production of color images by the dye diffusion transfer process. The dyes are (in non-metallized form), in the form of so-called "dye-releasers", bound to a redox-active carrier radical provided with a ballast group, which dye-releasers are associated to a light-sensitive silver halide emulsion layer. During development, the metallizable dyes are image-wise released and are converted, after diffusion into a light-receiving layer, into the corresponding metal complexes ##STR1## wherein E represents an electron acceptor radical; andK represents the radical of an azo coupler component, derived from an open-chain or closed ring ketomethylene compound, a cyclic enamine compound or a phenolic compound.Type: GrantFiled: June 26, 1985Date of Patent: July 15, 1986Assignee: Agfa-Gevaert AktiengesellschaftInventors: Peter Bergthaller, Jurgen Strauss, Hans-Volker Runzheimer, Gerhard Wolfrum
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Patent number: 4594426Abstract: Benzoxazole derivatives represented by general formula (I) which are intermediates for synthesis of o-sulfonamidophenol derivatives useful as dye releasing redox compounds in a color diffusion transfer color image forming process: ##STR1## wherein R.sup.1 and R.sup.2, which may be the same as or different from each other, each represents an alkyl group or an aryl group or they may combine and form a ring; R.sup.3 represents a hydrogen atom, an alkyl group or an aryl group; R.sup.4 represents an alkyl group or an aryl group; R.sup.5 represents an alkyl group, an alkoxy group, an alkylthio group, an arylthio group, a halogen atom or an acylamino group, or --CR.sup.1 R.sup.2 R.sup.3 and R.sup.5 may combine and form the nucleus ##STR2## which is condensed at the 6- and the 7-positions of the benzoxazole nucleus; and n is 0, 1 or 2.Type: GrantFiled: January 16, 1981Date of Patent: June 10, 1986Assignee: Fuji Photo Film Co., Ltd.Inventors: Shinsaku Fujita, Koichi Koyama, Yoshio Inagaki
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Patent number: 4579805Abstract: Dyes corresponding to formula I may be released imagewise from dye releasers in the dye diffusion transfer process. The dyes obtained are lightfast cyan dyes with improved spectral properties and reduced sensitivity to reducing agents ##STR1## the meanings of symbols given in formula I (A, A', G, R.sup.1, R.sup.2, R.sup.3 and R.sup.4) are indicated in the description.Type: GrantFiled: November 23, 1984Date of Patent: April 1, 1986Assignee: Agfa-Gevaert AktiengesellschaftInventors: Peter Bergthaller, Hauke Furstenwerth, Rudolf Stolzenburg, Paul Marx, Holger Heidenreich
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Patent number: 4524124Abstract: 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: GrantFiled: June 18, 1984Date of Patent: June 18, 1985Assignee: Agfa-Gevaert AktiengesellschaftInventors: Peter Bergthaller, Rudolf Stolzenburg, Paul Marx, Rainer Hamprecht
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Patent number: 4524123Abstract: 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: GrantFiled: March 27, 1984Date of Patent: June 18, 1985Assignee: Agfa-Gevaert AktiengesellschaftInventors: Gunther Schenk, Peter Bergthaller, Holger Heidenreich, Gerhard Wolfrum
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Patent number: 4521506Abstract: 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: GrantFiled: June 5, 1984Date of Patent: June 4, 1985Assignee: Agfa-Gevaert AktiengesellschaftInventors: Rudolf Stolzenburg, Peter Bergthaller, Gerhard Wolfrum, Jurgen Strauss
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Patent number: 4520095Abstract: 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: GrantFiled: October 4, 1983Date of Patent: May 28, 1985Assignee: Konishiroku Photo Industry Co., Ltd.Inventors: Tatsuhiko Kobayashi, Satoru Ikeuchi, Kazumasa Watanabe, Shunji Suginaka
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Patent number: 4439513Abstract: 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: GrantFiled: December 28, 1982Date of Patent: March 27, 1984Assignee: Fuji Photo Film Co., Ltd.Inventors: Kozo Sato, Shinsaku Fujita, Hideki Naito, Hiroshi Hara
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Patent number: 4425422Abstract: 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: GrantFiled: May 6, 1982Date of Patent: January 10, 1984Assignee: Konishiroku Photo Industry Co., Ltd.Inventors: Tawara Komamura, Jiro Takahashi, Ryuichiro Kobayashi
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Patent number: 4420550Abstract: 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: GrantFiled: January 17, 1983Date of Patent: December 13, 1983Assignee: Eastman Kodak CompanyInventors: Steven Evans, James K. Elwood
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Patent number: 4419435Abstract: 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: GrantFiled: January 17, 1983Date of Patent: December 6, 1983Assignee: Eastman Kodak CompanyInventors: James A. Reczek, James K. Elwood
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Patent number: 4409315Abstract: Photographic assemblages are described employing positive-working redox dye-releasers and a cover sheet containing an oxidant having an electrode potential of from about -200 mV up to about 1000 mV versus a saturated calomel electrode at a pH of about 5 to about 6. The oxidant is capable of oxidizing electron transfer agent in the system. The reduced form of the oxidant is incapable of reducing the positive-working redox dye-releaser. After processing, the oxidant reacts with the electron transfer agent to prevent it from reacting with the dye releaser which would otherwise cause further dye release. D.sub.min stability is thereby improved.Type: GrantFiled: June 28, 1982Date of Patent: October 11, 1983Assignee: Eastman Kodak CompanyInventors: Eugene A. Armour, Richard P. Henzel, Rowland G. Mowrey
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Patent number: 4407930Abstract: Photographic elements, diffusion transfer assemblages and processes are described which employ a nondiffusible, redox, dye-releasing compound comprising a ballasted, sulfonamidophenol or sulfonamidonaphthol compound having a dye moiety attached thereto through the sulfonamido group of the compound, the sulfonamido group being located in a position which is conjugated with respect to the position of the hydroxy group of the compound, and wherein(a) the compound has at least one substituent thereon in a position which is conjugated with respect to the position of the sulfonamido group, the substituent being selected from the group consisting of hydroxy, sulfonamido, phosphonamido and carbonamido, and(b) the compound not having a hydroxy, alkoxy, aryloxy, sulfonamido, phosphonamido or carbonamido group thereon in a position which is conjugated with respect to the position of the hydroxy group of the compound,with the proviso that when the compound is a 2-sulfonamidophenol and has only one substituent thereon inType: GrantFiled: May 21, 1982Date of Patent: October 4, 1983Assignee: Eastman Kodak CompanyInventors: Robert E. Ross, Lee J. Fleckenstein, Michael E. Campbell
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Patent number: 4407931Abstract: 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: GrantFiled: June 28, 1982Date of Patent: October 4, 1983Assignee: Eastman Kodak CompanyInventor: Steven Evans
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Patent number: 4407928Abstract: Photographic assemblages and processes are described employing positive-working redox dye-releasers and a processing composition containing a ketal blocked quinone which is soluble therein. After processing, when the pH is lowered, the free quinone is released for reaction with residual electron transfer agent present in the assemblage to prevent it from reacting with the dye releaser, which would otherwise cause further dye release. D.sub.min stability is thereby improved.Type: GrantFiled: June 28, 1982Date of Patent: October 4, 1983Assignee: Eastman Kodak CompanyInventor: Noel R. Vanier
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Patent number: 4396699Abstract: A process for the production of a multi-color dye image by dye diffusion transfer operating with a photographic multilayer multi-color material containing different non-diffusing dyes or dye precursor compounds that when contacted with an aqueous alkaline liquid remain immobile in an alkali-permeable colloid layer but are capable of being reduced by a developing agent at a rate slower than the reduction of image-wise developable silver halide and in reduced state under alkaline conditions are capable of releasing a diffusible dye or dye precursor moiety, and wherein as illustrated in the drawing dye images with higher color saturation are obtained by more extensive oxidation of developing agent in the image-wise photo-exposed area due to the use in the alkaline processing liquid of a silver halide solvent forming an alkali-soluble and reducible silver complex compound.Type: GrantFiled: August 12, 1981Date of Patent: August 2, 1983Assignee: AGFA-Gevaert, N.V.Inventors: Wilhelmus Janssens, Daniel A. Claeys
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Patent number: 4391896Abstract: Curve shape control, especially for lower scale contrast, of a photographic element is achieved by employing with the silver halide emulsion layer two nondiffusible redox dye-releasing compounds of different relative reactivities, the reactivity of the compound which is more reactive being at least 1.5 times the reactivity of the compound which is less reactive. Preferred compounds are ballasted sulfonamido compounds, each of which has a color-providing moiety attached thereto through a sulfonamido group which is alkali-cleavable upon oxidation. Preferred more reactive sulfonamido compounds have a N,N-disubstituted carbamoyl ballast group. The color-providing moieties can be (1) transferred imagewise to an image-receiving layer to provide a useful image, or (2) can be merely diffused out of the element to provide a retained image therein which can be treated to form a color transparency or a motion picture film.Type: GrantFiled: September 20, 1978Date of Patent: July 5, 1983Assignee: Eastman Kodak CompanyInventors: Thomas O. Maier, Jack L. Richards
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Patent number: 4386150Abstract: 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: GrantFiled: December 18, 1981Date of Patent: May 31, 1983Assignee: Polaroid CorporationInventors: Stephen R. Herchen, Gary N. Widiger
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Patent number: 4381339Abstract: Novel non-diffusing reducible compounds of formula I which under alkaline development conditions release a diffusible photographically useful compound are of use in color diffusion transfer processes. ##STR1## R.sup.0 completes a ring system; E represents a reducible group;W reduces the electron density in the position of E so that E is reducible under photographic development conditions;GR.sup.1 represents a group from which photographically useful compound R.sup.1 is released;XR.sup.2 represents a group that by reduction of E is activated to cooperate with GR.sup.1 in an intramolecular reaction with release of R.sup.1.Type: GrantFiled: April 9, 1981Date of Patent: April 26, 1983Assignee: Agfa-Gevaert AktiengesellschaftInventors: Gunter Renner, Erich Wolff
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Patent number: 4369243Abstract: 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: GrantFiled: March 6, 1981Date of Patent: January 18, 1983Assignee: Agfa-Gevaert AktiengesellschaftInventors: Hans-Heinrich Credner, Wolfgang Lassig, Karl-Wilhelm Schranz
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Patent number: 4366240Abstract: 5- or 6-membered .alpha.-lactones of phenolic compounds, in which the phenyl ring carries a hydroxyl or amino group in its 2- or 4-position to the lactonized phenolic hydroxyl group and in which the lactone ring carries an electron accepting substituent, so that the lactone ring is readily cleavable at pH values of from 10 to 13 to form an electron donor compound (ED-compound) having a redox potential of less than +0.255 V determined against a normal calomel electrode at pH 0 are useful ED precursor compounds for non-diffusing reducible color providing compounds.Type: GrantFiled: February 17, 1981Date of Patent: December 28, 1982Assignee: Agfa-Gevaert AktiengesellschaftInventors: Wolfgang Lassig, Ernst Meier, Siegfried Schleger
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Patent number: 4363865Abstract: 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: GrantFiled: March 4, 1981Date of Patent: December 14, 1982Assignee: Eastman Kodak CompanyInventors: James A. Reczek, Thomas R. Welter
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Patent number: 4357411Abstract: 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: GrantFiled: July 13, 1981Date of Patent: November 2, 1982Assignee: Eastman Kodak CompanyInventor: Norman W. Kalenda
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Patent number: 4357412Abstract: 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: GrantFiled: July 13, 1981Date of Patent: November 2, 1982Assignee: Eastman Kodak CompanyInventors: Richard B. Anderson, Norman W. Kalenda
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Patent number: 4357410Abstract: 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: GrantFiled: July 13, 1981Date of Patent: November 2, 1982Assignee: Eastman Kodak CompanyInventors: Richard B. Anderson, Norman W. Kalenda
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Patent number: 4353975Abstract: A dye-diffusion transfer process for producing (a) dye image(s) with improved dye density is provided, said process comprising the steps of:(1) image-wise photo-exposing a photographic color material, which contains at least one alkali-permeable silver halide hydrophilic colloid layer which contains in operative contact therewith or therein a non-diffusing dye or dye precursor compound that when contacted with an aqueous alkaline liquid remains immobile in an alkali-permeable colloid layer and is capable of being reduced by a silver halide developing agent at a rate slower than that of imagewise developable silver halide and in reduced state under alkaline conditions is capable of releasing a diffusible dye or dye precursor moiety, and(2) applying in the presence of a developing agent an aqueous alkaline liquid to said photoexposed material, characterized in that said liquid contains triisopropanolamine.Type: GrantFiled: August 12, 1981Date of Patent: October 12, 1982Assignee: Agfa-Gevaert, N.V.Inventors: Wilhelmus Janssens, Daniel A. Claeys
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Patent number: 4346161Abstract: 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: GrantFiled: April 29, 1981Date of Patent: August 24, 1982Assignee: Eastman Kodak CompanyInventors: James J. Krutak, Robert J. Maleski, William H. Moore
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Patent number: 4336322Abstract: 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: GrantFiled: July 18, 1980Date of Patent: June 22, 1982Assignee: Fuji Photo Film Co., Ltd.Inventors: Shinsaku Fujita, Koichi Koyama, Yoshio Inagaki, Kokichi Waki
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Patent number: 4323635Abstract: A color photographic material suitable for processing with an alkaline solution in the presence of a developing agent is described, comprising a support and, in sequence, the following five layers:(1) a first emulsion layer containing an internal latent image forming direct reversal silver halide emulsion that is selectively sensitive to light in a first spectral region;(2) a first color material layer containing a ballasted dye releasing redox compound that provides a dye image that selectively absorbs light in the first spectral region;(3) an intermediate layer containing a ballasted reducing agent that captures an oxidized developing agent or electron transfer agent;(4) a second emulsion layer containing an internal latent image forming direct reversal silver halide emulsion that is selectively sensitive to light in a second spectral region; and(5) a second color material layer containing a ballasted dye releasing redox compound that provides a dye image that selectively absorbs light in the second spectraType: GrantFiled: November 6, 1980Date of Patent: April 6, 1982Assignee: Fuji Photo Film Co., Ltd.Inventor: Yasushi Oishi
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Patent number: 4308336Abstract: In color photographic sensitive materials comprising at least one direct reversal silver halide emulsion layer associated with a diffusible dye-releasing redox compound on a base, the improvement which comprises that at least one of a layer containing said redox compound or said direct reversal silver halide emulsion layer contains about 5 to 200 mg per 100 millimols silver in the emulsion layer of a compound represented by the general formula (I): ##STR1## wherein A.sub.1 and A.sub.2 each represents a hydrogen atom or a hydrolyzable group, P, Q and R which may be the same or different each represents a hydrogen atom, an alkyl group, an aryl group, an alkylthio group, an arylthio group, a hydroxyl group, a halogen atom, an alkoxy group, an aryloxy group, a heterocyclic group or an --S--Z.sup.2 group, Z.sup.1 and Z.sup.2 may be the same or different and each represents an unsaturated heterocyclic residue which is photographically inactive when bonded to the hydroquinone through the sulfur moiety, and --S--Z.Type: GrantFiled: September 2, 1980Date of Patent: December 29, 1981Assignee: Fuji Photo Film Co., Ltd.Inventors: Kokichi Waki, Keiichi Adachi, Seiki Sakanoue
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Patent number: 4287292Abstract: 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: GrantFiled: August 1, 1980Date of Patent: September 1, 1981Assignee: Eastman Kodak CompanyInventors: Derek D. Chapman, James A. Reczek
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Patent number: 4273855Abstract: A compound of the following formula and use of this compound in a photographic material and a photographic diffusion transfer process for the production of color images: ##STR1## wherein R represents a hydrogen atom or an alkyl group with 1 to 4 C atoms;A represents an oxyalkylene group, such as --CH.sub.2 --CH.sub.2 --O--;n represents 1 or 2;X represents a residue of a dye or a dye precursor, which either directly or by means of an intermediate link Z is linked to the SO.sub.2 -group;Z represents an alkylene group of 1 to 6 C atoms, an arylene group, or a heterocyclic group, which is linked to the residue X either directly or by means of --O--, --S--, --SO.sub.2 --, --NR-- (R being hydrogen or an alkyl group), --CO--, --CO--NH--, or --SO.sub.2 --NH--;R.sup.1 represents --OR.sup.2, --SR.sup.2 or ##STR2## R.sup.2 being hydrogen, an alkyl group with 1 to 22 C atoms, a cycloalkyl group or an aryl group wherein said alkyl, cycloalkyl and aryl groups may be further substituted, R.sup.Type: GrantFiled: March 12, 1979Date of Patent: June 16, 1981Assignee: AGFA-GEVAERT N.V.Inventors: Jan Jaeken, Andre Verhecken, Hans Vetter, Paul Marx
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Patent number: 4269928Abstract: A photographic dye diffusion transfer process is provided which operates by imagwise release of a dye.The dye diffuses to a receiving layer and is mordanted there to give a dye image. The dyes are released from a compound of the formula D--E--F--BAL by reductive cleavage.D is a group which contains the residue of diffusible dye, BAL is a ballasting group which renders the compound containing it substantive to the layer in which it is present, D and E being joined by any type of chemical bond and E and F represent a single or double bond system which links D and BAL and which has a reduction potential above -200 mV measured against a standard hydrogen electrode at a pH of less than 3 and which bond can be reductively cleaved at a pH of less than 3 by a reducing agent which is able to act at a pH below 3.Type: GrantFiled: February 23, 1979Date of Patent: May 26, 1981Assignee: Ciba-Geigy AktiengesellschaftInventors: Leslie F. A. Mason, Rainer Kitzing, Brian R. D. Whitear, William E. Long, Glenn P. Wood, David L. R. Reeves
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Patent number: 4264701Abstract: Diffusion transfer color processes and products are disclosed employing image-dye providing materials providing magenta image dyes having the chromophoric system represented by the formula ##STR1## wherein each R is the same or different and is an alkyl group, and each X is the same or different and is hydrogen or an alkyl group (including substituted alkyl). The dye image-providing material includes a diffusion control moiety, such as a hydroquinonyl group, and may be diffusible or nondiffusible as a function of the diffusion control moiety.Type: GrantFiled: April 24, 1980Date of Patent: April 28, 1981Assignee: Polaroid CorporationInventors: Louis Locatell, Jr., Howard G. Rogers, Ruth C. Bilofsky, Ronald F. Cieciuch, Charles M. Zepp
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Patent number: 4264704Abstract: Novel xanthene dye developer compounds which include three or four silver halide developing groups are disclosed. Also described are photographic products and processes utilizing the dye developers.Type: GrantFiled: April 24, 1980Date of Patent: April 28, 1981Assignee: Polaroid CorporationInventors: Alan L. Borror, Louis Cincotta, Edmond M. Mahoney, Michael H. Feingold
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Patent number: 4258117Abstract: A method is disclosed of photographically processing a negative-working imagewise exposed silver halide photographic element to produce a reversal dye image comprising (a) developing the imagewise exposed silver halide with an electron transfer agent to produce oxidized electron transfer agent which reacts with a competing oxidizable substance and (b) developing silver halide remaining with the electron transfer agent in the presence of a dye image providing compound capable, after the competing oxidizable substance has been depleted, of reacting with the oxidized electron transfer agent to produce a reversal dye image. Image transfer film units are disclosed useful in the practice of this method. Such film units include those containing in addition to the competing oxidizable substance and initially immobile dye image providing compound a layer containing additional silver halide and a scavenger separating the additional silver halide from the immobile dye image providing compound.Type: GrantFiled: November 1, 1979Date of Patent: March 24, 1981Assignee: Eastman Kodak CompanyInventors: John Morgan, Peter D. Marsden
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Patent number: 4258120Abstract: A nondiffusible sulfonamido compound which is alkali-cleavable upon oxidation to release a diffusible photographically useful material, said nondiffusible sulfonamido compound having the formula: ##STR1## wherein: (a) R.sup.1 is alkyl, aryl sulfamyl, carbamyl, carbonamido, carbonyl, carbonyloxy or sulfonamido;(b) R.sup.2 is alkyl having from 1 to 18 carbon atoms, aryl, or alkylphenyl having from 7 to 12 carbon atoms;(c) R.sup.3 and R.sup.4 are independently alkyl, or aryl, or R.sup.3 and R.sup.4, taken together, form a fused carbocyclic or heterocyclic ring;(d) NHSO.sub.2 PUG represents a sulfonamido group;(e) PUG represents a photographically useful group; and(f) at least one of R.sup.1, R.sup.2, R.sup.3, or R.sup.Type: GrantFiled: April 24, 1979Date of Patent: March 24, 1981Assignee: Eastman Kodak CompanyInventors: Claude F. Gerbal, Thomas E. Gompf, Pierre D. Collet
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Patent number: 4256826Abstract: A bleach-fix sheet for use in color photographic processes comprises a support having thereon a bleaching agent, a fixing agent and a hardened hydrophilic binder. In a preferred embodiment, the bleach-fix sheet is useful to bleach and fix a retained image in a color image diffusion transfer unit.Type: GrantFiled: August 14, 1978Date of Patent: March 17, 1981Assignee: Eastman Kodak CompanyInventors: Gerhard Popp, Patrick H. Saturno, Keith H. Stephen
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Patent number: 4256831Abstract: A light-sensitive photographic element comprising a support and at least one light-sensitive silver halide emulsion layer coated thereon having associated therewith a magenta image dye-providing compound which releases a magenta dye or a precursor thereof corresponding to the imagewise exposure of said emulsion layer, said magenta dye-providing compound being a compound represented by formula [I]: ##STR1## wherein Car represents a carrier moiety which can be oxidized under alkaline conditions to release a diffusible dye or a precursor thereof from said compound;R.sup.1 and R.sup.2, which may be the same or different, independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms (provided that the total sum of carbon atoms in R.sup.1 and R.sup.2 does not exceed 5), or R.sup.1 and R.sup.Type: GrantFiled: August 22, 1979Date of Patent: March 17, 1981Assignee: Konishiroku Photo Industry Co., Ltd.Inventors: Masaru Kanbe, Kazumasa Watanabe, Morito Uemura, Jiro Takahashi, Ryuichiro Kobayashi, Tatsuhiko Kobayashi
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Patent number: 4250246Abstract: 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 magenta dye releasing redox (DRR) compound.Type: GrantFiled: June 25, 1979Date of Patent: February 10, 1981Assignee: Fuji Photo Film Co., Ltd.Inventors: Isamu Itoh, Yoshinobu Yoshida
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Patent number: 4242435Abstract: For the production of cyan and magenta images by the dye diffusion transfer process dye-providing compounds of the formula I are suitable ##STR1## in which A=an oxydizable carrier residue containing a diffusion-preventing radical;n= 0 or 1;P=a monocyclic aromatic radical;M=hydrogen, halogen, alkyl sulfonyl, aryl sulfonyl or sulfamoyl;Q=acylamino;R.sup.1 =hydrogen or a hydrolyzable radical.Type: GrantFiled: February 9, 1979Date of Patent: December 30, 1980Assignee: AGFA-Gevaert, A.G.Inventors: Walter Puschel, Hans Vetter, Paul Marx
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Patent number: 4234672Abstract: Shifted photographic dyes which have good storage stability, yet rapidly unblock under processing conditions contain a blocked hydroxy group and a neighboring group that anchimerically assists the hydrolytic cleavage of the blocking group under processing conditions.Type: GrantFiled: October 10, 1978Date of Patent: November 18, 1980Assignee: Eastman Kodak CompanyInventors: John A. Ford, Gregory J. Lestina
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Patent number: 4232107Abstract: Said material contains a quinone-type compound which corresponds to one of the formulae (A) or (B) and which is capable in reduced state and under alkaline conditions of releasing a photographically useful group e.g. a dye: ##STR1## wherein: each of (Nuox).sup.1 and (Nuox).sup.2 represents an oxidized nucleophilic group,Z represents a bivalent atomic group which is electronegative,Q together with the Z group represents a releasable photographically useful group,each of R.sup.1, R.sup.2 and R.sup.3 is hydrogen, halogen, alkyl, alkoxy, or an acylamino group or R.sup.1 and R.sup.2 in adjacent positions on the ring form a ring fused with the remainder of the molecule, or R.sup.2 and R.sup.3 together are fused with the remainder of the molecule.each of R.sup.4 and R.sup.5 represents hydrogen or a hydrocarbon group.At least one of the substituents R.sup.1, R.sup.2, R.sup.3, R.sup.4 or R.sup.5 is a ballasting group X.Type: GrantFiled: March 15, 1979Date of Patent: November 4, 1980Assignee: AGFA-GEVAERT N.V.Inventor: Wilhelmus Janssens
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Patent number: T994003Abstract: Photographic elements, diffusion transfer assemblages and processes are described which employ a novel nondiffusible compound having a novel releasable azo dye. The dyes are azophenols, or precursors of azophenols, and have an electron withdrawing group in one of the positions ortho to the phenolic hydroxy group and a carbamoyl electron withdrawing group in the other position ortho to the phenolic hydroxy group.Type: GrantFiled: September 21, 1979Date of Patent: May 6, 1980Inventor: Kenneth N. Kilminster