Substituted At Coupling Position With Other Than Hydrogen Patents (Class 430/385)
  • Patent number: 9229322
    Abstract: Disclosed and claimed herein is a composition of matter having a general structure chosen from (I), (II), (III) or (IV); wherein X and Y are the same or different, wherein at least one of X and Y comprises an acid labile group, wherein R1 is a saturated or unsaturated group having from 1-4 carbon atoms, R2 is chosen from hydrogen or a saturated or unsaturated group having from 1-4 carbon atoms, R3 is a saturated or unsaturated group having from 1-4 carbon atoms, and R4 is a saturated or unsaturated group having from 1-4 carbon atoms.
    Type: Grant
    Filed: October 21, 2014
    Date of Patent: January 5, 2016
    Inventors: Alex Phillip Graham Robinson, Dongxu Yang, Andreas Frommhold, Thomas Lada, John L. Roth, Xiang Xue, Edward A. Jackson
  • Patent number: 9122156
    Abstract: Disclosed herein is a composition of matter having a general structure chosen from (I), (II), (III) or (IV); at least one photo acid generator; at least one crosslinker; and at least one solvent; wherein X and Y are the same or different, wherein at least one of X and Y comprises an acid labile group, wherein R1 is a saturated or unsaturated group having from 1-4 carbon atoms, R2 is chosen from hydrogen or a saturated or unsaturated group having from 1-4 carbon atoms, R3 is a saturated or unsaturated group having from 1-4 carbon atoms, and R4 is a saturated or unsaturated group having from 1-4 carbon atoms.
    Type: Grant
    Filed: October 21, 2014
    Date of Patent: September 1, 2015
    Inventors: Alex Philip Graham Robinson, Dongxu Yang, Andreas Frommhold, Thomas Lada, John L. Roth, Xiang Xue, Edward A. Jackson
  • Patent number: 7166422
    Abstract: Provided is a silver halide color photographic material having at least one yellow-coloring photosensitive silver halide emulsion layer, at least one magenta-coloring photosensitive silver halide emulsion layer, at least one cyan-coloring photosensitive silver halide emulsion layer, and at least one non-photosensitive non-coloring hydrophilic colloid layer on a reflective support, wherein, after being color developed, the reflection density A(?) at a wavelength of ? nm in the non-exposed portion of the material is at most 0.07 at 450 nm, at most 0.09 at 550 nm and at most 0.07 at 650 nm and the mean grain size of the silver halide grains in the yellow-coloring photosensitive silver halide emulsion layer in the material is at most 0.70 ?m.
    Type: Grant
    Filed: May 22, 2002
    Date of Patent: January 23, 2007
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Shinichi Nakahira, Shin Soejima, Hiroyuki Yoneyama, Naoya Shibata, Naoto Ohshima
  • Patent number: 7112400
    Abstract: An image forming method including a step of imagewise exposing a silver halide color photographic photosensitive material having, on a support, photographic constituent layers including at least one blue sensitive silver halide emulsion layer, at least one green sensitive silver halide emulsion layer, at least one red sensitive silver halide emulsion layer, and at least one non-photosensitive hydrophilic colloid layer, a color developing step, a bleach-fixing step and a rinsing step.
    Type: Grant
    Filed: November 3, 2004
    Date of Patent: September 26, 2006
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Shin Soejima, Kentaro Okazaki
  • Patent number: 6900006
    Abstract: The invention relates to a photographic element comprising at least one light-sensitive silver halide emulsion layer having associated therewith in the same dispersion a certain de-aggregating compound at least one heterocyclic cyan dye-forming coupler of a specified formula and an aromatic stabilizer of a particular formula. The combination provides improved image stability.
    Type: Grant
    Filed: December 4, 2002
    Date of Patent: May 31, 2005
    Assignee: Eastman Kodak Company
    Inventors: Danuta Gibson, David Clarke, Christopher J. Winscom, Michael W. Crawley
  • Patent number: 6858380
    Abstract: A silver halide color photosensitive material comprises at least one layer on a support. At least one of the layers contains a coupler represented by general formula (I): wherein X represents H or split-off group; R1 and R2 independently represents an electron withdrawing group whose Hammett ?p value is 0.20 or greater, provided that the sum of R1 and R2 ?p values is 0.65 or greater; R3 represents a group selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl and heterocyclic, each of which may have a substituent; R4 represents H, or a group selected from alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, acyl, alkoxycarbonyl, aryloxycarbonyl and carbamoyl, each of which may have a substituent, provided that R3 and R4 may be bonded to form a ring; R11, R12 and R13 independently represent an alkyl group having 1-30 carbon atoms; R represents a substituent; and n represents an integer of 0-3.
    Type: Grant
    Filed: January 28, 2003
    Date of Patent: February 22, 2005
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Yasuhiro Kato, Hisashi Mikoshiba, Naoto Matsuda
  • Patent number: 6852479
    Abstract: An image forming method including a step of imagewise exposing a silver halide color photographic photosensitive material having, on a support, photographic constituent layers including at least one blue sensitive silver halide emulsion layer, at least one green sensitive silver halide emulsion layer, at least one red sensitive silver halide emulsion layer, and at least one non-photosensitive hydrophilic colloid layer, a color developing step, a bleach-fixing step and a rinsing step. At least one of the at least one red sensitive silver halide emulsion layer contains at least one compound represented by the following general formula (IA) and/or at least one coupler represented by the following general formulae (PTA-I) and (PTA-II).
    Type: Grant
    Filed: April 23, 2003
    Date of Patent: February 8, 2005
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Shin Soejima, Kentaro Okazaki
  • Patent number: 6806042
    Abstract: A print material having a support, at least one red-sensitive silver halide emulsion layer containing at least one cyan coupler, at least one green-sensitive silver halide emulsion layer containing at least one magenta coupler and at least one blue-sensitive silver halide emulsion layer containing at least one yellow coupler, characterised in that the red-sensitive layer contains at least one oil former, the cyan coupler is of the formula in which R1 means a hydrogen atom or an alkyl group, R2 means an alkyl, aryl or hetaryl group, R3 means an alkyl or aryl group, R4 means an alkyl, alkenyl, alkoxy, aryloxy, acyloxy, acylamino, sulfonyloxy, sulfamoylamino, sulfonamido, ureido, hydroxycarbonyl, hydroxycarbonylamino, carbamoyl, alkylthio, arylthio, alkylamino or arylamino group or a hydrogen atom and Z means a hydrogen atom or a group eliminable under the conditions of chromogenic development, and the ratio by weight of oil former to cyan coupler is less than 1:1, is distinguished by exc
    Type: Grant
    Filed: July 2, 2003
    Date of Patent: October 19, 2004
    Assignee: Agfa-Gevaert
    Inventors: Ralf Weimann, Markus Geiger, Cuong Ly, Klaus Sinzger, Beate Weber, Heinz Wiesen
  • Patent number: 6783924
    Abstract: A color photographic silver halide material comprising a substrate, at least one red-sensitive silver halide emulsion layer containing at least one cyan coupler, at least one green-sensitive silver halide emulsion layer containing at least one magenta coupler and at least one blue-sensitive silver halide emulsion layer containing at least one yellow coupler, characterised in that the silver halide crystals of the red-sensitive layer have a chloride content of at least 95 mol %, the cyan coupler corresponding to formula wherein R1 represents a hydrogen atom or an alkyl group, R2 represents an alkyl, aryl or hetaryl group R3 represents an alkyl or aryl group, R4 represents an alkyl, alkenyl, alkoxy, aryloxy, acyloxy, acylamino, sulphonyloxy, sulphamoylamino, sulphonamido, ureido, hydroxycarbonyl, hydroxycarbonylamino, carbamoyl, alkylthio, arylthio, alkylamino or arylamino group or a hydrogen atom and Z represents a hydrogen atom or a group which may be split off under the conditions of c
    Type: Grant
    Filed: July 2, 2003
    Date of Patent: August 31, 2004
    Assignee: Agfa-Gevaert
    Inventors: Ralf Weimann, Markus Geiger, Cuong Ly, Klaus Sinzger, Beate Weber, Heinz Wiesen
  • Patent number: 6780573
    Abstract: The invention relates to a color silver halide photographic element comprising a light-sensitive silver halide emulsion layer, said silver halide emulsion being in reactive association with an amino acid compound according to Formula (I): wherein: COUP is a moiety that reacts with oxidized developer to release the amino acid timing group but does not substantially contribute any density in the visible region to the element after processing is complete; n is 0 or 1; R1 is an alkyl or alkenyl group of 4 carbon atoms or more or an aryl group with 10 carbon atoms or more; R2 is an alkyl or aryl group so the sum total of carbon atoms in R1 and R2 together are at least 5; and PUG is a photographically useful group.
    Type: Grant
    Filed: May 30, 2003
    Date of Patent: August 24, 2004
    Assignee: Eastman Kodak Company
    Inventors: Stephen P. Singer, Christopher W. Grote, Robert C. Stewart, Janet N. Younathan, Jerrold N. Poslusny
  • Patent number: 6764815
    Abstract: A color photographic print material which contains a cyan coupler of the formula in which R1 means a hydrogen atom or an alkyl group, R2 means OR3 or NR4R5, R3 means an unsubstituted or substituted alkyl group with 1 to 6 C atoms, R4 means an unsubstituted or substituted alkyl group with 1 to 6 C atoms, R5 means a hydrogen atom or an unsubstituted or substituted alkyl group with 1 to 6 C atoms, R6 means an unsubstituted or substituted alkyl group and Z means a hydrogen atom or a group eliminable under the conditions of chromogenic development, wherein the total number of the C atoms of the alkyl groups R3 to R6 in a coupler molecule is 8 to 18, is simultaneously distinguished by good light and dark stability as well as by good color reproduction. The couplers furthermore exhibit very good solubility in conventional coupler solvents.
    Type: Grant
    Filed: May 9, 2003
    Date of Patent: July 20, 2004
    Assignee: AGFA-Gevaert
    Inventor: Ralf Weimann
  • Patent number: 6730465
    Abstract: The invention relates to a photographic element comprising at least one light-sensitive silver halide emulsion layer having associated therewith a heterocyclic magenta or cyan dye-forming coupler of formula (I), wherein HET is a heterocyclic coupler comprising at least two fused rings and having at least one bridgehead nitrogen atom; S is bonded to a position of HET capable of releasing the heterocyclylthio moiety from HET upon reaction with oxidized developer; X is a heteroatom selected from nitrogen, oxygen and sulfur, bonded to the carbon atom bearing the exocyclic S and to other ring atoms only; and Z are the atoms necessary to complete an unsubstituted or substituted heterocyclic ring or ring system, which may contain one or more other heteroatoms selected from nitrogen, oxygen and sulfur; provided also that the heterocyclylthio moiety released upon reaction with oxidized developer does not significantly inhibit silver development nor cause a bleach acceleration effect.
    Type: Grant
    Filed: March 10, 2003
    Date of Patent: May 4, 2004
    Assignee: Eastman Kodak Company
    Inventors: Philip A. Allway, Paul L. Stanley
  • Publication number: 20040067455
    Abstract: This invention relates to a photographic element comprising a support and at least two silver halide emulsion layers further comprising an electron transfer agent releasing compound represented by the formula (I):
    Type: Application
    Filed: September 16, 2002
    Publication date: April 8, 2004
    Applicant: Eastman Kodak Company
    Inventors: John E. Keevert, Stephen P. Singer, Kenneth J. Reed, Kenneth J. Lushington, Mary C. Brick, James A. Friday
  • Patent number: 6699650
    Abstract: There is provided a photographic element comprising at least one silver halide emulsion layer having associated therewith a novel phenolic cyan dye-forming coupler of formula (I) wherein X is hydrogen or a group that can be split off by the reaction of the coupler with an oxidised colour developing agent, and one of Y and Z is the group  wherein each R is independently an unsubstituted or substituted alkyl or aryl group or a 5-10 membered heterocyclic ring which contains one or more heteroatoms selected from nitrogen, oxygen and sulfur, which ring is unsubstituted or substituted; R1 is hydrogen or an unsubstituted or substituted alkyl or aryl group, R2 is an unsubstituted or substituted alkyl or aryl group or a 5-10 membered heterocyclic ring which contains one or more heteroatoms selected from nitrogen, oxygen and sulfur, which ring is unsubstituted or substituted; R3 is hydrogen or an unsubstituted or substituted alkyl or aryl group, n is 1 or 2, and the othe
    Type: Grant
    Filed: May 22, 2001
    Date of Patent: March 2, 2004
    Assignee: Eastman Kodak Company
    Inventors: David Clarke, Llewellyn J. Leyshon, Katie E. Smith
  • Publication number: 20040038158
    Abstract: An image forming method including a step of imagewise exposing a silver halide color photographic photosensitive material having, on a support, photographic constituent layers including at least one blue sensitive silver halide emulsion layer, at least one green sensitive silver halide emulsion layer, at least one red sensitive silver halide emulsion layer, and at least one non-photosensitive hydrophilic colloid layer, a color developing step, a bleach-fixing step and a rinsing step. At least one of the at least one red sensitive silver halide emulsion layer contains at least one compound represented by the following general formula (IA) and/or at least one coupler represented by the following general formulae (PTA-I) and (PTA-II).
    Type: Application
    Filed: April 23, 2003
    Publication date: February 26, 2004
    Applicant: FUJI PHOTO FILM CO., LTD.
    Inventors: Shin Soejima, Kentaro Okazaki
  • Patent number: 6689549
    Abstract: Disclosed is a photographic element comprising a light-sensitive silver halide emulsion layer having associated therewith a cyan coupler having the formula: wherein: the term “NB coupler” represents a coupler of formula (I) that forms a dye with the developer 4-amino-3-methyl-N-ethyl-N-(2-methanesulfonamidoethyl) aniline sesquisulfate hydrate for which the left bandwidth (LBW) using spin-coating is at least 5nm less than that of the same dye in solution form; V is a sulfone, sulfoxide or sulfonamide-containing group; Y is H or a coupling-off group; each Z1, Z2, Z3 and Z* are an independently selected substituent group where p is 0 to 2; provided that Z1, and Z2 or Z2 and Z3 can join to form a ring; provided further that Z1, and Z2 do not join to form an aromatic or heterocyclic ring; and provided further that the combined sum of the aliphatic carbon atoms in V, all Z′, Z″ and all Z* is at least 8.
    Type: Grant
    Filed: December 11, 2002
    Date of Patent: February 10, 2004
    Assignee: Eastman Kodak Company
    Inventors: William J. Begley, Brian Thomas, Natasha Andrievsky
  • Publication number: 20040023171
    Abstract: A print material having a support, at least one red-sensitive silver halide emulsion layer containing at least one cyan coupler, at least one green-sensitive silver halide emulsion layer containing at least one magenta coupler and at least one blue-sensitive silver halide emulsion layer containing at least one yellow coupler, characterised in that the red-sensitive layer contains at least one oil former, the cyan coupler is of the formula 1
    Type: Application
    Filed: July 2, 2003
    Publication date: February 5, 2004
    Applicant: Agfa-Gevaert N.V. (Belgium)
    Inventors: Ralf Weimann, Markus Geiger, Cuong Ly, Klaus Sinzger, Beate Weber, Heinz Wiesen
  • Patent number: 6680165
    Abstract: The invention provides a color negative photographic element comprising a light sensitive silver halide emulsion imaging layer having associated therewith a cyan dye-forming coupler dispersion comprising a first 2-ureido-5-acylamino substituted phenolic cyan dye-forming coupler [P], a second phenolic cyan dye-forming coupler [AP] where the 2-substituent is other than an ureido group, a substantially non-color-developable phenolic activator compound [ACT], and a non-phenolic organic coupler solvent having a boiling point of at least 150C; wherein compounds represented by [P], [AP], and [ACT] are present in the coupler dispersion in relative weight fractions of from 0.30 to 0.65 for [P], from 0.15 to 0.35 for [AP], and from 0.15 to 0.
    Type: Grant
    Filed: October 24, 2002
    Date of Patent: January 20, 2004
    Assignee: Eastman Kodak Company
    Inventors: Jerrold N. Poslusny, Paul B. Merkel, David A. Steele, Drake M. Michno, David S. Ross, Richard K. Rothrock, Paul L. Zengerle
  • Publication number: 20030232289
    Abstract: Disclosed is a colour photographic element containing one or more cyan dye-forming couplers, a UV absorber and a specific class of stabiliser, and an imaging process used therewith. The element exhibits improved stability.
    Type: Application
    Filed: October 11, 2002
    Publication date: December 18, 2003
    Applicant: Eastman Kodak Company
    Inventors: Danuta Gibson, Llewellyn J. Leyshon, David Clarke
  • Patent number: 6641990
    Abstract: Disclosed is a photographic element comprising a light-sensitive silver halide emulsion layer having associated therewith a cyan coupler having the formula: wherein: the term “NB coupler” represents a coupler of formula (I) that forms a dye with the developer 4-amino-3-methyl-N-ethyl-N-(2-methanesulfonamidoethyl) aniline sesquisulfate hydrate for which the left bandwidth (LBW) using spin-coating is at least 5 nm less than that of the same dye in solution form; V is a sulfone, sulfoxide or sulfonamide-containing group; Y is H or a coupling-off group; each Z′, Z″ and Z* is an independently selected substituent group where n and p are independently 0 to 2; X1 and X2 are halogen atoms and may be the same or different; and provided that the combined sum of the aliphatic carbon atoms in V, all Z′, Z″ and all Z* is at least 8.
    Type: Grant
    Filed: August 29, 2002
    Date of Patent: November 4, 2003
    Assignee: Eastman Kodak Company
    Inventors: William J. Begley, Brian Thomas
  • Patent number: 6562558
    Abstract: Disclosed is a photographic element comprising a light-sensitive silver halide emulsion layer having associated therewith a cyan “NB coupler” having the formula (I): wherein: the term “NB coupler” represents a coupler of formula (I) that forms a dye for which the left bandwidth (LBW) using spin-coating is at least 5 nm less than that of the same dye in solution form; X is selected from O, NR* or S and R* is an alkyl, carbocyclic or heterocyclic group; L is a linking group and a is 0 or 1; Y is H or a coupling-off group; Z* is a substituent group and p is 0 to 2; and R1 and R2 are independently selected H or substituents; provided that the combined sum of the aliphatic carbon atoms in R1, R2, R*, L and all Z* is at least 8.
    Type: Grant
    Filed: December 6, 2001
    Date of Patent: May 13, 2003
    Assignee: Eastman Kodak Company
    Inventors: William J. Begley, Gary M. Russo
  • Patent number: 6548234
    Abstract: The invention provides a photographic element comprising at least one light-sensitive silver halide emulsion layer having associated therewith at least one cyan dye-forming coupler, UV absorber and (A) a stabilizer of formula (I) wherein R1 is an unsubstituted or substituted alkyl or aryl group or a 5- to 10- membered heterocyclic ring which contains one or more heteroatoms selected from nitrogen, oxygen and sulfur, which ring is unsubstituted or substituted; Z is a hydrogen atom or a substituent group; X is a group selected from —SO2—, —SO—, —COO—,—CO— and —CS—, W is one or more unsubstituted or independently substituted alkylene groups connecting the nitrogen atom to X, and p is 0 or 1; R2 is a substituent group; or the groups represented by Z and R2 can be joined to form a ring which may be substituted; and (B) a high-boiling solvent of formula (II) wherein R3 is an unsubstituted or substituted alkyl or
    Type: Grant
    Filed: August 21, 2001
    Date of Patent: April 15, 2003
    Assignee: Eastman Kodak Company
    Inventor: Danuta Gibson
  • Patent number: 6541192
    Abstract: A silver halide color photographic lightsensitive material comprising at least one layer on a support, wherein the at least one layer contains a coupler represented by formula (I) below wherein X represents a hydrogen atom, halogen atom, arylthio group, carbamoyloxy group, heterocyclic carbonyloxy group, etc., each of R1 and R2 represents an electron-attracting group having a Hammett's substituent constant &sgr;p value of not less than 0.20, the sum of the &sgr;p values of R1 and R2 being not less than 0.65, each of R3 and R4 represents a alkyl group, alkenyl group, alkynyl group, cycloalkyl group, cycloalkenyl group, etc., or alternatively, R3 and R4 may bond together to form a ring structure; and each of R11 to R15 independently represents a hydrogen atom or a substituent.
    Type: Grant
    Filed: November 21, 2001
    Date of Patent: April 1, 2003
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Yasuhiro Kato, Hisashi Mikoshiba, Naoto Matsuda, Tetsuro Kojima
  • Patent number: 6528241
    Abstract: A light-sensitive silver-halide color photographic element comprising a multifunctional coupler enabling formation of an infrared dye on development, wherein the multifunctional coupler has the property that it is capable of forming a distinctly colored cyan dye with an oxidized form of the developer 4-(N-ethyl-N-2-hydroxyethyl)-2-methylphenylenediamine.
    Type: Grant
    Filed: August 13, 2001
    Date of Patent: March 4, 2003
    Assignee: Eastman Kodak Company
    Inventor: Richard P. Szajewski
  • Patent number: 6521397
    Abstract: Disclosed is a photographic element comprising a support bearing a light sensitive silver halide emulsion layer having associated therewith a dye forming coupler having a formula I, wherein: Ballast is a group containing at least 6 aliphatic carbon atoms, V represents a chain of three or four atoms, which may be substituted, selected from C, N, O and S sufficient to form an aromatic ring fused to the azole ring and n is 0 or 1, provided that if n is 0, Y and Ballast are directly attached to the 5-membered azole ring, W is an electron withdrawing group selected from the group consisting of —CN, —CONR1R2, —CO2R1, —NO2, and —SO2R1 where R1 and R2 are H or substituents; X is H or a coupling-off group; Y is H or a substituent; Z is an atom or group selected from >N—R, —O—, and —S—.
    Type: Grant
    Filed: April 12, 2002
    Date of Patent: February 18, 2003
    Assignee: Eastman Kodak Company
    Inventors: Mbiya Kapiamba, Donald R. Diehl, James L. Edwards, David G. Lincoln, Gary M. Russo
  • Patent number: 6518000
    Abstract: Disclosed is a photographic element comprising a light-sensitive silver halide emulsion layer having associated therewith a coupler that forms a dye for which the &lgr;max using spin-coating is shifted towards the infrared region of the spectrum by at least 30 nm, when compared to the &lgr;max of the same dye in solution form, to a value of at least 700 nm. Such an element is useful for recording metadata with an image.
    Type: Grant
    Filed: January 30, 2002
    Date of Patent: February 11, 2003
    Assignee: Eastman Kodak Company
    Inventors: William J. Begley, Gary M. Russo, Mathilde R. Triguel
  • Patent number: 6513212
    Abstract: A color photographic element comprising at least three light-sensitive units which have their individual sensitivities in different wavelength regions, at least one of units comprising a light-sensitive silver-halide emulsion, binder, and a coupler represented by formula I: COUP—(T)m—L—DYE′  (I) wherein COUP is a coupler parent group capable of reacting with an oxidized developer to form a first cyan dye and is bonded at a coupling position to a releasable group that forms a second dye of the same hue, as described in the specification.
    Type: Grant
    Filed: December 19, 2001
    Date of Patent: February 4, 2003
    Assignee: Eastman Kodak Company
    Inventors: Jared B. Mooberry, Wojciech K. Slusarek, David T. Southby, David H. Levy, Xiqiang Yang
  • Patent number: 6426178
    Abstract: The invention relates to a photographic element for forming neutral images comprising a cyan dye-forming coupler, a magenta dye-forming coupler of formula wherein Ra and Rb represents H or a substituent; X is hydrogen or a coupling-off group; Za, Zb, and Zc are a substituted methine group, ═N—, ═C—, or —NH—; and yellow dye-forming coupler of formula,  wherein R5 is an alkoxy group with more than one carbon atom, aryloxy, anilino, arylthio, alkylthio, or dialkylamino groups linked to the anilide phenyl ring by oxygen, sulfur or nitrogen; R6 is selected from hydrogen, halogen, alkoxycarbonyl(—CO2R), carbamoyl(—CONRR′), carbonamido(—NRCOR′), sulfonate(—OSO2R), sulfamoyl (—SO2NRR′), sulfonamido(—NRSO2R′), or sulfonyl(—SO2R); R and R′ may be hydrogen, alkyl or aryl groups; q is 1 to 4; R7 is alkyl, cyclic, or multicyclic alky, aryl, heterocyclic, heteroaromatic, and
    Type: Grant
    Filed: August 7, 2000
    Date of Patent: July 30, 2002
    Assignee: Eastman Kodak Company
    Inventors: Michael R. Roberts, Kurt M. Schroeder, Frank D. Coms
  • Patent number: 6387606
    Abstract: Disclosed is a photographic element comprising a light-sensitive silver halide emulsion layer having associated therewith a cyan “NB coupler” having the formula (I): wherein: the term “NB coupler” represents a coupler of formula (I) that forms a dye for which the left bandwidth (LBW) using spin-coating is at least 5 nm less than that of the same dye in solution form; Y is H or a coupling-off group; each Z″ and Z* is an independently selected substituent group where n is 0 to 4 and p is 0 to 2; W2 represents the atoms necessary to complete a heterocyclic ring group; and V is a sulfone or sulfoxide containing group; provided that the combined sum of the aliphatic carbon atoms in V, all Z″ and all Z* is at least 8. The element exhibits improved cyan dye hue.
    Type: Grant
    Filed: October 18, 2001
    Date of Patent: May 14, 2002
    Assignee: Eastman Kodak Company
    Inventors: William J. Begley, Frank D. Coms, Gary M. Russo
  • Patent number: 6368780
    Abstract: A silver halide photographic material excellent in color generation, color reproduction and image fastness, which comprises at least one coupler represented by the following formula: wherein R1 represents an alkyl group which may be optionally substituted, with the proviso that an alkyl group substituted by a halogen atom alone and an alkyl group substituted by a halogen atom and an aryl group are excluded from R1; R2 and R3, which may be the same or different, each represents a hydrogen atom or a substituent; and X1 represents a group which can leave by coupling with an oxidation product of a color developing agent; and an image formation method using the same.
    Type: Grant
    Filed: July 28, 2000
    Date of Patent: April 9, 2002
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Kiyoshi Takeuchi, Taiji Katsumata, Satoshi Sano, Yuki Mizukawa
  • Publication number: 20020025497
    Abstract: A silver halide color photographic light-sensitive material has a red-, green-, and blue-sensitive emulsion layer in this order from the side closest to a support.
    Type: Application
    Filed: July 6, 2001
    Publication date: February 28, 2002
    Inventors: Naoto Matsuda, Hisashi Mikoshiba
  • Patent number: 6348302
    Abstract: An image-forming method using an exposure head having plural beam light sources that correspond to each exposure point and that emit each light with the same wavelength, to subject to exposure a light-sensitive material provided at least with a light-sensitive silver halide emulsion and a binder on a support, which method comprises arranging M sets of the beam light sources in a sub-scanning direction, perpendicular to a main scanning direction, along which the exposure head is moved, at predetermined intervals, and allowing the light-sensitive material to move in the sub-scanning direction, in steps of a distance of (the length of the exposure head in the aligned direction)/N (N≧2), to carry out superposing exposure N times, with an exposure time per exposure being 10−3 sec or less, thereby forming M×N pixels per exposure head in every M sets of exposure point, to form an image, wherein the silver halide emulsion contains Ir, in an amount to be added of 10−7 to 10−10 mol per mol of
    Type: Grant
    Filed: July 13, 2000
    Date of Patent: February 19, 2002
    Assignee: Fuji Photo Film Co., Ltd.
    Inventor: Takuji Kosugi
  • Publication number: 20020015923
    Abstract: The invention provides a multilayer silver halide color photographic element comprising a support having coated thereon at least two red-sensitive silver halide emulsion layers having different sensitivity to red light, characterized in that the most sensitive of said red-sensitive silver halide emulsion layers comprises a core-shell silver bromoiodide tabular emulsion having a pure bromide core, a total silver iodide content lower than 10% and an aspect ratio higher than 4.
    Type: Application
    Filed: May 21, 2001
    Publication date: February 7, 2002
    Applicant: Tulalip
    Inventors: Giuseppe Rocca, Antonio Poggi, Simona Fava
  • Publication number: 20020012886
    Abstract: The present invention relates to a novel blocked phenylenediamine developer useful, in reactive association, for enabling, on development, a non-magenta color, for example a cyan color, from a dye-forming coupler. In one embodiment, the developer has the property that the dye color formed with the coupler is distinctly different from the color formed by the same coupler with an oxidized form of the conventional developer 4-(N-ethyl-N-2-hydroxyethyl)-2-methylphenylenediamine. The invention is also directed to a light-sensitive silver-halide color photographic element comprising the blocked developing agent according to the present invention.
    Type: Application
    Filed: May 31, 2001
    Publication date: January 31, 2002
    Applicant: Eastman Kodak Company
    Inventors: Richard P. Szajewski, Lyn M. Irving
  • Publication number: 20010014432
    Abstract: Disclosed is a photographic element comprising a light-sensitive silver halide emulsion layer having associated therewith a cyan “NB coupler” having the formula (I): 1
    Type: Application
    Filed: February 12, 2001
    Publication date: August 16, 2001
    Inventors: William J. Begley, Frank D. Coms, Gary M. Russo
  • Patent number: 6261755
    Abstract: The invention provides a photographic element comprising at least one light-sensitive silver halide emulsion layer having associated therewith: (A) a phenolic cyan dye-forming narrow bandwidth “NB coupler”; (B) a phenolic cyan dye-forming coupler of formula (II): wherein: R3 is an unsubstituted or substituted alkyl or aryl group or a 5-10 membered heterocyclic ring which contains one or more heteroatoms selected from nitrogen, oxygen and sulfur, which ring is unsubstituted or substituted; R4 is an unsubstituted or substituted alkyl group; R5 is hydrogen, halogen or an unsubstituted or substituted alkyl or aryl group or a 5-10 membered heterocyclic ring which contains one or more heteroatoms selected from nitrogen, oxygen and sulfur, which ring is unsubstituted or substituted; and Z is a hydrogen atom or a group which can be split off by the reaction of the coupler with an oxidized color-developing agent; and (C) a stabilizer of formula (III) wherein: eac
    Type: Grant
    Filed: February 28, 2000
    Date of Patent: July 17, 2001
    Assignee: Eastman Kodak Company
    Inventors: Danuta Gibson, James S. Honan, Thomas A. Rosiek
  • Patent number: 6251575
    Abstract: Disclosed is a photographic element comprising a light-sensitive silver halide emulsion layer having associated therewith a “NB coupler” having the formula (I): wherein: the term “NB coupler” represents a coupler of formula (I) that forms a dye for which the left bandwidth (LBW) using spin-coating is at least 5 nm less than that of the same dye in solution form; Y is H or a coupling-off group; each Z* is an independently selected substituent group where p is 0 to 2; V is a substituent group containing a sulfone group; R4 is represented by the formula wherein each of R5, R6 and R7 is hydrogen or an independently selected substituent with no more than one being hydrogen; provided that two or more of R5, R6 and R7 may join to form a ring or rings and provided that the combined sum of the aliphatic carbon atoms in V, R4 and all Z* is at least 8, and provided further that R4 is not a fully fluorinated alkyl group. Such elements provide improved hue.
    Type: Grant
    Filed: November 1, 2000
    Date of Patent: June 26, 2001
    Assignee: Eastman Kodak Company
    Inventors: William J. Begley, Gary M. Russo, Denis T. Curt
  • Patent number: 6242609
    Abstract: A method for manufacturing a color coupler used in a silver halide photographic light-sensitive material using an ammonium trihalide. Said method for manufacturing the color coupler comprising the following step: a step for halogenating a coupling position of a four equivalent coupler using a halogenating agent, wherein said halogenating agent is said ammonium trihalide.
    Type: Grant
    Filed: April 7, 1999
    Date of Patent: June 5, 2001
    Assignee: Konica Corporation
    Inventor: Fumio Ishii
  • Patent number: 6207363
    Abstract: Disclosed is a photographic element comprising a light-sensitive silver halide emulsion layer having associated therewith a cyan “NB coupler” having the formula (I): wherein: the term “NB coupler” represents a coupler of formula (I) that forms a dye for which the left bandwidth (LBW) using spin-coating is at least 5 nm less than that of the same dye in solution form; Y is H or a coupling-off group; each Z″ and Z* is an independently selected substituent group where n is 1 to 4 and p is 0 to 2; W2 represents the atoms necessary to complete a carbocyclic or heterocyclic ring group; and V is a sulfone or sulfoxide containing group; provided that the combined sum of the aliphatic carbon atoms in V, all Z″ and all Z* is at least 8; provided further that there is one and only one Z″ substituent ortho to the carbonamido group linking the W2 ring to the rest of the coupler; and provided still further that when W2 forms a carbocyclic aromatic ring, at
    Type: Grant
    Filed: December 28, 1999
    Date of Patent: March 27, 2001
    Assignee: Eastman Kodak Company
    Inventors: William J. Begley, Frank D. Coms, Gary M. Russo
  • Patent number: 6197492
    Abstract: Disclosed is a photographic element comprising a light-sensitive silver halide emulsion layer having associated therewith a cyan “NB coupler” having the formula (I): wherein: the term “NB coupler” represents a coupler of formula (I) that forms a dye for which the left bandwidth (LBW) using spin-coating is at least 5nm less than that of the same dye in solution form; Y is H or a coupling-off group; each Z″ and Z* is an independently selected substituent group where n is 0 to 4 and p is 0 to 2; W2 represents the atoms necessary to complete a heterocyclic ring group; and V is a sulfone or sulfoxide containing group; provided that the combined sum of the aliphatic carbon atoms in V, all Z″ and all Z* is at least 8. The element exhibits improved cyan dye hue.
    Type: Grant
    Filed: December 28, 1999
    Date of Patent: March 6, 2001
    Assignee: Eastman Kodak Company
    Inventors: William J. Begley, Frank D. Coms, Gary M. Russo
  • Patent number: 6197491
    Abstract: Disclosed is a photographic element comprising a light-sensitive silver halide emulsion layer having associated therewith a “NB coupler” having the formula (I): wherein: the term “NB coupler” represents a coupler of formula (I) that forms a dye for which the left bandwidth (LBW) using spin-coating is at least 5 nm less than that of the same dye in solution form; Y is H or a coupling-off group; each Z* is an independently selected substituent group where p is 0 to 2; V is a substituent group containing a sulfonamido group; R4 is hydrogen or a group bonded to the carbonamido group by an aliphatic carbon atom; provided that the combined sum of the aliphatic carbon atoms in V, R4 and all Z* is at least 8. The element provides a dye of improved hue.
    Type: Grant
    Filed: December 28, 1999
    Date of Patent: March 6, 2001
    Assignee: Eastman Kodak Company
    Inventors: William J. Begley, Gary M. Russo, Denis T. Curt
  • Patent number: 6197490
    Abstract: Disclosed is a photographic element comprising a light-sensitive silver halide emulsion layer having associated therewith a “NB coupler” having the formula (I): wherein the term “NB coupler” represents a coupler of formula (I) that forms a dye for which the left bandwidth (LBW) using spin-coating is at least 5 nm less than that of the same dye in solution form; Y is H or a coupling-off group; each Z″ and Z* is an independently selected substituent group where n is 0 to 5 and p is 0 to 2; W2 represents the atoms necessary to complete a carbocyclic or heterocyclic ring group; and V is a substituent group containing a sulfonamido group; provided that the combined sum of the aliphatic carbon atoms in V, all Z″ and all Z* is at least 8. The element provides a dye of improved hue.
    Type: Grant
    Filed: December 28, 1999
    Date of Patent: March 6, 2001
    Assignee: Eastman Kodak Company
    Inventors: William J. Begley, Gary M. Russo, Denis T. Curt
  • Patent number: 6194132
    Abstract: Disclosed is a photographic element comprising a light-sensitive silver halide emulsion layer having associated therewith a cyan coupler having the formula: wherein: V is a sulfone or sulfoxide containing group; Y is H or a coupling-off group; W2 represents the atoms necessary to complete a carbocyclic or heterocyclic ring group; each Z″, Z* and Z# is an independently selected substituent group where n and r are independently 0 to 4 and p is 0 to 2; and X is a halogen atom, and s is 1 to 5; provided that the combined sum of the aliphatic carbon atoms in V, all Z″, all Z#, and all Z* is at least 8. The element exhibits improved cyan dye stability.
    Type: Grant
    Filed: December 28, 1999
    Date of Patent: February 27, 2001
    Assignee: Eastman Kodak Company
    Inventors: William J. Begley, Frank D. Coms, Gary M. Russo
  • Patent number: 6190852
    Abstract: Disclosed is a photographic element comprising a light-sensitive silver halide emulsion layer having associated therewith a cyan dye-forming coupler represented by Formula (I): wherein: each R1 and R3 is an independently selected substituent, m is 0 to 5, and p is 0 to 2; X is hydrogen or a coupling-off group; W and W2 represent the atoms necessary to complete rings; and R2 is an alkyl or aryl group. The element provides desirable hue properties and ease of synthesis.
    Type: Grant
    Filed: December 28, 1999
    Date of Patent: February 20, 2001
    Assignee: Eastman Kodak Company
    Inventors: Albert J. Mura, Raymond P. Scaringe, John W. Harder
  • Patent number: 6190850
    Abstract: Disclosed is a photographic element comprising a light-sensitive silver halide emulsion layer having associated therewith a cyan “NB coupler” having the formula (I): wherein: the term “NB coupler” represents a coupler of formula (I) that forms a dye for which the left bandwidth (LBW) using spin-coating is at least 5 nm less than that of the same dye in solution form; Y is H or a coupling-off group; each Z″ and Z* is an independently selected substituent group where n is 1 to 4 and p is 0 to 2; W2 represents the atoms necessary to complete a carbocyclic or heterocyclic ring group; and V is a sulfone or sulfoxide containing group; provided that the combined sum of the aliphatic carbon atoms in V, all Z″ and all Z* is at least 8; and the sum of the aliphatic carbon atoms in all Z″ substituents combined is at least 6; provided further that when W2 forms a carbocyclic aromatic ring, at least one Z″ is selected from the group consisting of alk
    Type: Grant
    Filed: December 28, 1999
    Date of Patent: February 20, 2001
    Assignee: Eastman Kodak Company
    Inventors: William J. Begley, Frank D. Coms, Gary M. Russo
  • Patent number: 6190851
    Abstract: Disclosed is a photographic element complising a light sensitive silver halide emulsion layer having associated therewith a cyan dye forming coupler having Formula (I): wherein R1 and R3 independently represent hydrogen or an alkyl group; R2 represents a carbocyclic or heterocyclic aromatic group; n represents 1, 2, or 3; each X is an independently selected substituent where at least one X located at a position of the phenyl ring meta or para to the sulfonyl group and is either an alkoxy group having a branched carbon or an aiyloxy group; and Z represents hydrogen or a group that can be split off by the reaction of the coupler with an oxidized color-developing compound; provided that the substituents of the compound of formula (I) are selected so that the compound has a melting point of 160° C. or less. The element provides improved phase stability during manufacturing while exhibiting satisfactory hue and dye light stability.
    Type: Grant
    Filed: December 28, 1999
    Date of Patent: February 20, 2001
    Assignee: Eastman Kodak Company
    Inventors: John W. Harder, James S. Honan, Albert J. Mura
  • Patent number: 6180331
    Abstract: Disclosed is a photographic element comprising a light-sensitive silver halide emulsion layer having associated therewith a cyan “NB coupler” having the formula (I): wherein: the term “NB coupler” represents a coupler of formula (I) that forms a dye for which the left bandwidth (LBW) using spin-coating is at least 5 nm less than that of the same dye in solution form; Y is H or a coupling-off group; each Z″ and Z* is an independently selected substituent group where n is 1 to 4 and p is 0 to 2; W2 represents the atoms necessary to complete a carbocyclic ring group; and V is a substituent containing a heterocyclic sulfone or sulfoxide group; provided that the combined sum of the aliphatic carbon atoms in V, all Z″ and all Z* is at least 8. The element exhibits improved cyan dye hue.
    Type: Grant
    Filed: December 28, 1999
    Date of Patent: January 30, 2001
    Assignee: Eastman Kodak Company
    Inventors: William J. Begley, Frank D. Coms, Gary M. Russo
  • Patent number: 6068969
    Abstract: There is disclosed a silver halide color photographic light-sensitive material, which comprises a compound of formula (I): wherein, in formula (I), R.sup.11 is a hydrogen atom, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, or an aryl group; R.sup.12, R.sup.13, R.sup.14, R.sup.15, R.sup.16, and R.sup.17, each independently represent a hydrogen atom or an alkyl group having 1 to 30 carbon atoms, and n is 0 or 1. This color photographic light-sensitive material is excellent in fastness of dye image.
    Type: Grant
    Filed: January 22, 1999
    Date of Patent: May 30, 2000
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Hisashi Mikoshiba, Shin Soejima, Yasuhiro Shimada, Osamu Takahashi, Yasuaki Deguchi
  • Patent number: 6048674
    Abstract: The invention provides photographic element comprising a first light sensitive silver halide emulsion layer having associated therewith a cyan dye-forming coupler, a second light sensitive silver halide emulsion layer having associated therewith a magenta dye-forming coupler, and a third light sensitive silver halide emulsion layer having associated therewith a yellow dye-forming coupler,wherein the normalized spectral transmission density distribution curve of the dye formed by the cyan coupler upon development with a p-phenylenediamine developer has a density between 0.7 and 0.78 at 600 nm and a density between 0.8 and 0.91 at 610 nm. Such an element enables an increase in the color gamut for imaging.
    Type: Grant
    Filed: December 23, 1998
    Date of Patent: April 11, 2000
    Assignee: Eastman Kodak Company
    Inventors: Elizabeth McInerney, Patti L. Bushnell
  • Patent number: 6043017
    Abstract: The present invention relates to a new compound of formula (I) with the proviso that Y represents N, and also relates to a colour photographic silver halide material comprising at least one red-sensitive silver halide layer with which according to the invention a compound of formula (I) is associated, and also relates to a photographic colour development process in which couplers of formula (I) are reacted with colour developers of the phenylenediamine and/or diaminotoluene type to form coupling products which exhibit a strong absorption, particularly in the infrared region. The present invention further relates to the use of compounds of formula (I) as cyan and/or infrared couplers in colour photographic silver halide materials.
    Type: Grant
    Filed: June 24, 1999
    Date of Patent: March 28, 2000
    Assignee: Agfa-Gevaert NV
    Inventor: Peter Bergthaller