Substituted At Coupling Position With Other Than Hydrogen Patents (Class 430/387)
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Patent number: 5491049Abstract: The present invention provides a photographic element comprising a support, at least one photosensitive silver halide layer and in or adjacent said silver halide layer a colour coupler of one of the general formulas: ##STR1## wherein R.sup.1 is a subsituted or unsubstituted aryl or a subsituted or unsubstituted heterocylic group,R.sup.2 is a subsituted or unsubstituted, saturated or unsaturated, primary or secondary alkyl group in which the carbon atom which joins R.sup.2 to rest of the coupler has at least one fluorine atom attached to it,R.sup.3 is an electron-withdrawing group, andX is H or a coupling-off group,and wherein the electron-withdrawing properties of R.sup.1 are such that the dye formed on coupling with oxidised colour developing agent 4-(N-ethyl-N-2-hydroxyethyl)-2-methylphenylenediamine has a .lambda..sub.max of from 537 to 570 nm.The invention also includes the coupler composition, methods of synthesizing the coupler and a method of forming an image in a photographic element.Type: GrantFiled: May 4, 1994Date of Patent: February 13, 1996Assignee: Eastman Kodak CompanyInventor: Philip A. Allway
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Patent number: 5482821Abstract: The invention provides a photographic process and element where the element comprises a light sensitive silver halide layer containing (1) an image dye-forming bicyclic azole coupler having bonded to the coupling site a group other than hydrogen which is clearable during the development process; (2) an azopyrazolone masking coupler; and (3) a stabilizing coupler having bonded to the coupling site only hydrogen atoms and/or carbon atoms which are not cleavable to permit dye formation during development.Type: GrantFiled: September 30, 1993Date of Patent: January 9, 1996Assignee: Eastman Kodak CompanyInventors: Daniel L. Kapp, Janet N. Younathan
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Patent number: 5470696Abstract: A photographic element comprising a support, at least one photosensitive silver halide layer and associated therewith a color coupler of the general formula (1) or (2): ##STR1## wherein A and B represent the same or different electron-withdrawing group,X is H or a group which splits off on coupling with oxidized color developer,R is an alkyl, cycloalkyl, aryl or heterocyclic which may be substituted, --COR.sup.1, --CSR.sup.1, SOR.sup.1, SO.sub.2 R.sup.1, --NHCOR.sup.1, --CONHR.sup.1, --COOR.sup.1, --COSR.sup.1, --NHSO.sub.2 R.sup.1 wherein R.sup.1 is an alkyl, cycloalkyl, or aryl group any of which are optionally substituted,and wherein two or more of A, B, R, and X optionally form part of a ring,Link is a linking group andn is 0, 1 or 2.Type: GrantFiled: June 1, 1993Date of Patent: November 28, 1995Assignee: Eastman Kodak CompanyInventor: Hugh M. Williamson
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Patent number: 5470697Abstract: A magenta coupler and a light sensitive silver halide color photographic material containing the coupler are disclosed. The magenta coupler is represented by formulas ##STR1## wherein R.sub.1 is a hydrogen atom or a substituent, R.sub.2, R.sub.3 and R.sub.4 each represents a hydrogen atom or a substituent, L is an alkylene group, n is 0 or 1, R.sub.5 and R.sub.6 each represents a hydrogen atom or a substituent, where R.sub.5 and R.sub.6 may be condensed to form a cycle, and X is a hydrogen atom or an atom or a group that can be released upon the reaction with an oxidation product of color developing agent.Type: GrantFiled: June 1, 1994Date of Patent: November 28, 1995Assignee: Konica CorporationInventors: Hiroshi Kita, Hiroshi Ishidai, Yutaka Kaneko
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Patent number: 5462848Abstract: Color photographic materials comprise a support bearing a silver halide emulsion and a coupler composition. The coupler composition comprises a two-equivalent pyrazolone magenta dye-forming coupler, a ballasted carbonamide compound, and a developer inhibitor-releasing coupler. The carbonamide compound reduces continued coupling of the pyrazolone magenta dye-forming coupler during the bleach step in a color photographic process without altering the advantageous properties provided by the combination of the two-equivalent pyrazolone magenta dye-forming coupler and the developer inhibitor-releasing coupler.Type: GrantFiled: June 10, 1993Date of Patent: October 31, 1995Assignee: Eastman Kodak CompanyInventors: Paul B. Merkel, Stephen P. Singer
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Patent number: 5460924Abstract: This invention provides an accelerator for peracid bleaches used for bleaching silver halide photographic elements. The accelerator is a complex of ferric (Fe III) ion and a 2-pyridinecarboxylic acid or a 2,6-pyridinecarboxylic acid. The accelerator may be contained in the bleaching solution, a solution preceding the bleaching solution or in the photographic elements themselves.Type: GrantFiled: April 20, 1994Date of Patent: October 24, 1995Assignee: Eastman Kodak CompanyInventors: John M. Buchanan, Stuart T. Gordon, Keith H. Stephen, Richard P. Szajewski, Sidney J. Bertucci
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Patent number: 5457007Abstract: The image forming process of the present invention includes subjecting a photosensitive material having at least one dye-forming layer for each of the three primary colors on a support to scanning exposure using light sources modulated in accordance with the image data, thereby reproducing a full color image of quality in which delicate shades in a high density color developed portion of high purity are reproduced stably.Type: GrantFiled: July 13, 1994Date of Patent: October 10, 1995Assignee: Fuji Photo Film Co., Ltd.Inventor: Masahiro Asami
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Patent number: 5457020Abstract: Novel bicyclic pyrazolo couplers containing a ballast group of formula (I): ##STR1## are useful in photographic materials and processes. The couplers exhibit increased coupling activity, and provide formation of dyes having improved maximum magenta image dye density, hue, and dye light stability when employed in color photographic materials and processes.Type: GrantFiled: December 18, 1992Date of Patent: October 10, 1995Assignee: Eastman Kodak CompanyInventors: Philip T. S. Lau, Ping W. Tang, Stanley W. Cowan
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Patent number: 5451501Abstract: A 1H-pyrazolo[1,5-b][1,2,4]triazole magenta coupler having a t-alkyl group at the position-6 and an amido group-substituted phenyl group at the position-2 is disclosed. There is also disclosed a silver halide color photographic material containing the same.Type: GrantFiled: May 26, 1993Date of Patent: September 19, 1995Assignee: Fuji Photo Film Co., Ltd.Inventors: Yuki Mizukawa, Masuji Motoki, Tadahisa Sato, Osamu Takahashi
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Patent number: 5445926Abstract: Disclosed is a method for processing color photographic materials having a layer structure in which a cyan color-forming layer is disposed on the upper side of a pyrazoloazole type magenta coupler-containing magenta color-forming layer. A layer which does not contain any hydroquinones but contains a ultraviolet absorbent is provided above the cyan coupler-containing silver halide emulsion layer having a high chloride content, while below the cyan coupler-containing emulsion layer is provided another layer containing hydroquinones but not containing any ultraviolet absorbent. These materials are processed rapidly with a color developer under a reduced replenishment condition, wherein the amount of a color developer replenished is controlled to below 120 ml/m.sup.2, to provide color images fast to light and free from bluish unevenness in the edge part thereof.Type: GrantFiled: October 23, 1992Date of Patent: August 29, 1995Assignee: Fuji Photo Film Co., Ltd.Inventor: Kazunori Hasebe
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Patent number: 5443945Abstract: The invention provides novel photographic compositions comprising a propene isomer of the formula ##STR1## wherein A B or E, each individually represent hydrogen, or an electron withdrawing group, selected for example from --CN, --NO.sub.2, --SO.sub.2 R, --SO.sub.2 NH--, --CO.sub.2 R, --COR, --CONHR, --CONHAr, --CF.sub.3 halogen, amino, aryl, aralkyl, alkyl, cycloalkyl, alkyl (carbonyl)oxy, aryl (carbonyl)oxy, carboxy, alkoxycarbonyl, aryloxycarbonyl, carbamomyl, acyl, alkylaminocarbonyl, arylaminocarbonyl, alkoxycarbonylamino, acylamino, ureido, alkylsulphonylamino, arylsulphonylamino, sulphamoylamino, alkylsulphonyl, arylsulphonyl, sulphamoyl, imido, alkylthio, arylthio and heterocycles; the invention also provides a propene isomer of the formula I wherein D represents a group of the formula Ar--L--wherein Ar is a phenyl group optionally substituted with one or more substituents, and --L-- is a linking group incorporating a lone pair of electrons; and A, B, E and X are defined as R is above defined.Type: GrantFiled: May 19, 1993Date of Patent: August 22, 1995Assignee: Eastman Kodak CompanyInventor: Hugh M. Williamson
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Patent number: 5441851Abstract: A photographic element with a support and a silver halide emulsion layer includes a two-equivalent pyrazolone magenta dye-forming coupler and a heterocyclic nitrogen addendum which is a protic imidazole or a pyridine. The heterocylic nitrogen compound reduces continued coupling of two-equivalent magenta dye-forming couplers after removal from a developer solution, obviating the need for a stop bath after the development stage.Type: GrantFiled: November 25, 1991Date of Patent: August 15, 1995Assignee: Eastman Kodak CompanyInventors: Stephen P. Singer, Paul B. Merkel
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Patent number: 5429913Abstract: Photographic coupler compositions comprise a magenta dye-forming coupler and an alcohol in an amount sufficient to increase the activity of the dye-forming coupler. The alcohol is of the formula ##STR1## wherein R.sub.1 is selected from the group consisting of (a) unsubstituted alkyl and alkenyl groups, (b) alkyl groups containing one or more substitutents selected from the group consisting of aryl groups, alkenyl groups, halogen atoms, alkoxy groups, alkoxy carbonyl groups and acyloxy groups, (c) unsubstituted aryl groups and (d) aryl groups containing one or more substituents selected from the group consisting of alkyl groups, alkoxy groups, alkoxy carbonyl groups and acyloxy groups; and R.sub.2 and R.sub.3 are individually selected from hydrogen and the group of moieties from which R is selected, provided that the total number of carbon atoms contained in R.sub.1, R.sub.2 and R.sub.3 is at least 10.Type: GrantFiled: August 30, 1993Date of Patent: July 4, 1995Assignee: Eastman Kodak CompanyInventors: Paul B. Merkel, Edward Schofield
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Patent number: 5418123Abstract: (Magenta) colour images with improved stability to light may be obtained with a colour photographic recording material containing compounds of formula I as magenta couplers. The magenta couplers of formula I are particularly suitable for use in recording materials of positive colour images on light reflecting or transparent supports.Type: GrantFiled: November 12, 1993Date of Patent: May 23, 1995Assignee: Bayer AktiengesellschaftInventor: Erich Wolff
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Patent number: 5411841Abstract: Improved hue, speed of dye formation and reduced staining are provided by a photographic element comprising a light-sensitive silver halide layer having associated therewith a 1-phenyl-3-anilino-pyrazolo-5-one coupler comprising a ballasted parent and a coupling-off group and containing substituents on the 1-phenyl and 3-anilino rings of the parent having Hammett sigma values which together sum to at least 1.1, the coupler further having at the 4-position of the pyrazolone ring a coupling-off group comprising a phenylthio group containing a carbonamido substituent in the position para to the sulfur on the phenylthio ring with the substituents on the phenylthio ring selected such that the calculated log P of the thiophenol corresponding to the coupling-off group is at least 4.Type: GrantFiled: May 24, 1993Date of Patent: May 2, 1995Assignee: Eastman Kodak CompanyInventors: Stephen P. Singer, Paul B. Merkel, Bernard A. J. Clark, Paul L. R. Stanley
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Patent number: 5411848Abstract: A photographic element, and coupler employed therein, comprises a photographic silver halide emulsion layer containing a yellow dye-forming coupler having a the general formula: ##STR1## wherein Z is a ballasted group which splits off on silver halide development which is of such size and configuration to render the coupler non-diffusible in photographic layers, prior to splitting off, andR.sup.1 and R.sup.2 are each individually an alkyl or aryl group whose combined effect is to render the yellow dye formed on coupling sufficiently mobile to produce image smearing.Type: GrantFiled: July 14, 1994Date of Patent: May 2, 1995Assignee: Eastman Kodak CompanyInventors: John D. Goddard, Danuta Gibson
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Patent number: 5409808Abstract: Disclosed is a silver halide color photographic material having at least one light-sensitive silver halide emulsion layer on a support and containing at least one coupler of formula (I): ##STR1## where R.sub.1 represents an alkyl group; R.sub.2 and R.sub.3 each represent a hydrogen atom, an alkyl group or an aryl group, provided that both R.sub.2 and R.sub.3 are not hydrogen atoms at the same time; R.sub.4 and R.sub.5 each represent an alkyl group; X represents a hydrogen atom or a substituent capable of splitting off by coupling with an oxidation product of a developing agent; Y represents a substituent; n represents 0 or 1; and m represents an integer of from 0 to 3. The material has excellent sensitivity and gradation and has improved storage stability, especially latent image stability.Type: GrantFiled: February 12, 1993Date of Patent: April 25, 1995Assignee: Fuji Photo Film Co., Ltd.Inventors: Yuki Mizukawa, Hideaki Naruse, Toshiyuki Watanabe, Tadahisa Sato
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Patent number: 5405969Abstract: The invention provides a process for making a thioether compound having the formula:A--S--Rcomprising reacting:(1) Compound I having the formula:A--H (I)where A comprises a carbon atom bonded to H where that carbon is either capable of ionizing to a nucleophilic state or is conjugated to such an atom, with(2) Compound II having the formula:H--SR or RSSR (II)wherein R is selected from the group consisting of:(a) a substituted or-unsubstituted aryl group or alicyclic group, said groups being carbocyclic or heterocyclic, and(b) a thiocarbonyl group,in the presence of a base and an oxidizing agent that is free of reactive halogen and that is capable of oxidizing H--SR to RSSR.Type: GrantFiled: December 10, 1993Date of Patent: April 11, 1995Assignee: Eastman Kodak CompanyInventors: Charles W. Wright, Joan C. Potenza, John E. Leary, Jr., Chang K. Kim
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Patent number: 5403703Abstract: A silver halide color photographic light-sensitive material has at least one light-sensitive silver halide emulsion layer on a support, contains a pyrazoloazole-based coupler, and further contains a compound represented by Formula (I) and/or Formula (II) below:Formula (I) A--(L.sub.1).sub.j --(L.sub.2).sub.m --[(L.sub.3).sub.n --PUG].sub.sFormula (II) A--L.sub.4 --L.sub.5 --PUGwhere A represents a coupler moiety or an oxidation-reduction group, each of L.sub.1 and L.sub.3 represents a divalent timing group, L.sub.2 represents a timing group with a valency of 3 or more and does not use electron transfer via a conjugated system, L.sub.4 represents a coupling group such as --OCO--, L.sub.5 represents a group for releasing PUG by electron transfer along a conjugated system or L.sub.4, PUG represents a photographically useful group, each of j and n independently represents 0, 1, or 2, m represents 1 or 2, and s represents a number obtained by subtracting 1 from a valence number of L.sub.Type: GrantFiled: August 13, 1992Date of Patent: April 4, 1995Assignee: Fuji Photo Film Co., Ltd.Inventors: Keiji Mihayashi, Atsuhiro Ohkawa
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Patent number: 5399467Abstract: Novel photographic silver halide materials contain dye-forming couplers represented by formula (I): ##STR1## wherein K is a coupler moiety based on pyrazolone, phenol, naphthol, enamine, or acylacetamide to which the ballast group is attached, are useful in photographic materials and processes. The containing the couplers exhibit increased coupling activity, and provide formation of dyes having improved maximum magenta image dye density, contrast, and development speed.Type: GrantFiled: October 29, 1993Date of Patent: March 21, 1995Assignee: Eastman Kodak CompanyInventors: Sundaram Krishnamurthy, Stanley W. Cowan
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Patent number: 5389500Abstract: Disclosed is a method for forming color photographic images which comprises printing of color images obtained by use of a color photographic light-sensitive material, having on a support, a blue-sensitive silver halide emulsion layer, a green-sensitive silver halide emulsion layer and a red-sensitive silver halide emulsion layer onto a printing color photographic light-sensitive material having on a support, a yellow color forming layer, a magenta color forming layer and a cyan color forming layer, wherein the following requirements (A) and (B) are fulfilled,(A) wavelength .lambda..sub.B.sup.max to give the maximum value in spectral sensitivity distribution of a blue-sensitive silver halide emulsion layer is within the limits of 415 nm to 470 nm, and the sensitivity of the blue-sensitive emulsion layer at 480 nm is not more than 35% of the sensitivity at .lambda..sub.B.sup.Type: GrantFiled: October 19, 1993Date of Patent: February 14, 1995Assignee: Konica CorporationInventors: Hiroshi Shimazaki, Kuniaki Uezawa, Satoru Shimba, Yoshitaka Yamada
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Patent number: 5387500Abstract: A photographic element including a support and at least two green-sensitive silver halide emulsion layers of different sensitivity, each emulsion layer including a two-equivalent pyrazoloazole magenta dye-forming coupler having a structure according to formula I of the disclosure. The activity of the dye-forming coupler present in the layer of lower sensitivity is less than the activity of the dye-forming coupler present in the layer of higher sensitivity.Type: GrantFiled: May 27, 1994Date of Patent: February 7, 1995Assignee: Eastman Kodak CompanyInventors: Hans G. Ling, Drake M. Michno
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Patent number: 5378587Abstract: A photographic element contains a photographic silver halide layer having associated therewith a bicyclic pyrazolo coupler having a ballast group represented by Formula (I):--C(R').sub.m --L--Y--Ar(R").sub.nwherein:L is a divalent linking group connecting the methylene group to the remainder of the ballast group and containing at least one group selected from the group consisting of --NR.sup.1 CO--, --CONR.sup.1 --, --NR.sup.1 SO.sub.2 -- and --SO.sub.2 NR.sup.1 --, wherein R.sup.1 is hydrogen or a substituent;Y is a divalent linking group connecting L to Ar and containing a member selected from the group consisting of --O--, --S--, and --NR.sup.1 -- wherein R.sup.1 is hydrogen or a substituent;Ar is an aryl group;each R' and R" is independently a substituent, provided that at least one R" is a substituted or unsubstituted alkyl or alkoxy group having at least 10 carbon atoms; andm and n are at least 1.Type: GrantFiled: December 18, 1992Date of Patent: January 3, 1995Assignee: Eastman Kodak CompanyInventors: Sundaram Krishnamurthy, Stanley W. Cowan
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Patent number: 5376519Abstract: A color photographic material and process provide a two-equivalent 3-anilino pyrazolone magenta dye-forming coupler, a phenolic coupler solvent and at least one amine compound.Type: GrantFiled: April 23, 1992Date of Patent: December 27, 1994Assignee: Eastman Kodak CompanyInventors: Paul B. Merkel, Stephen P. Singer
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Patent number: 5372920Abstract: A multilayered color photographic element contains a support having coated thereon photographic silver halide emulsion layers including at least one blue-sensitive and at least three red-sensitive silver halide emulsion layers, said red-sensitive layers respectively being most, mid, and least red-sensitive relative to each other, said most and mid red-sensitive layers being contiguous, and the most red-sensitive layer being a coupler starved layer, which element comprises:(a) a yellow image dye-forming coupler and substantially no development inhibitor releasing coupler in the most red-sensitive layer; and(b) at least one development inhibitor releasing coupler in the mid red-sensitive layer.Type: GrantFiled: June 11, 1993Date of Patent: December 13, 1994Assignee: Eastman Kodak CompanyInventor: Larry D. Edwards
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Patent number: 5362882Abstract: A novel pyrrolotriazole derivative is disclosed, represented by any one of formulae (I), (II), (III), (IV), or (V): ##STR1## A heat transfer dye providing material is also disclosed, comprising a support having thereon a dye providing layer containing a heat migrating dye, said dye providing layer containing at least one pyrrolotriazole azomethine dye represented by any one of formulae (I), (II), (III), or (IV).Type: GrantFiled: June 5, 1992Date of Patent: November 8, 1994Assignee: Fuji Photo Film Co., Ltd.Inventors: Makoto Suzuki, Yasuhiro Shimada, Koushin Matsuoka, Shigeru Yamazaki, Katsuyoshi Yamakawa, Kozo Sato
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Patent number: 5358829Abstract: Novel bicyclic pyrazolo couplers contain a sulfone group of formula (I):--L--NHC(.dbd.O)--(L).sub.n --B--SO.sub.2 --R.sup.1 Iwherein:each L is independently a divalent group linking the adjacent groups;n is 0 or 1;B is a divalent group selected from aryl, aryloxy, aryloxyalkyl, and --C(R.sup.2)(R.sup.3)-- wherein R.sup.2 and R.sup.3 are independently hydrogen or alkyl; andR.sup.1 is a substituted or unsubstituted alkyl having 1 to 22 carbon atomsThese couplers are useful in photographic materials and processes. They exhibit improved color reproduction and dye light stability when employed in color photographic materials and processes.Type: GrantFiled: December 18, 1992Date of Patent: October 25, 1994Assignee: Eastman Kodak CompanyInventors: Ping W. Tang, Stanley W. Cowan
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Patent number: 5350667Abstract: A photographic element contains a light-sensitive silver halide layer having associated therewith a coupler which is a pyrazolone compound with a coupling-off substituent at the -4-position, said compound having the formula: ##STR1## wherein each R.sup.1 is independently a substituted or unsubstituted alkylsulfonyl or arylsulfonyl group; each R.sup.2 and R.sup.3 is independently a substituent; R.sup.4, R.sup.5, and R.sup.6 are independently hydrogen or substituted or unsubstituted alkyl groups; m and n are independently 0 or 1 but both are not 0; x1 and x2 are independently 0 to 5; and y is 0 to 3; provided that each of R.sup.3, R.sup.4, R.sup.5, and R.sup.6 is selected such that the calculated log P of the thiophenol corresponding to the substituent at the 4-position of the pyrazolone is at least 4. The photographic element provides an improved combination of low continued coupling together with a magenta hue exhibiting a long wavelength of maximum absorption.Type: GrantFiled: June 17, 1993Date of Patent: September 27, 1994Assignee: Eastman Kodak CompanyInventors: Stephen P. Singer, Paul B. Merkel, Bernard Arthur J. Clark, Paul Louis R. Stanley
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Patent number: 5342749Abstract: A silver halide color photographic material comprising a support having thereon at least one silver halide emulsion layer and containing a 1H-pyrazolo[5,1-c]-1,2,4-triazole couplers represented by the general formula (I) of the general formula (II): ##STR1## wherein A represents a group which is bonded to L via the benzene ring or a carbon atom in R.sup.Type: GrantFiled: December 21, 1993Date of Patent: August 30, 1994Assignee: Fuji Photo Film Co., Ltd.Inventors: Kei Sakanoue, Keizo Kimura
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Patent number: 5336593Abstract: The improved silver halide color photographic material contains at least one pyrazolotriazole base magenta coupler represented by the following general formula [Ia] or [Ib]: ##STR1## This photographic material is improved in image keeping quality, especially in lightfastness, without lowering the efficiency of color formation and it also insures good color reproduction.Type: GrantFiled: July 2, 1993Date of Patent: August 9, 1994Assignee: Konica CorporationInventors: Koji Daifuku, Hiroshi Kita, Yutaka Kaneko
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Patent number: 5318884Abstract: Photographic silver halide materials and processes employ at least one coupler having a coupling-off group which includes a carbocyclic or heterocyclic ring which bears a silyl substituent on at least one of its ring carbon atoms and is attached via another of its ring atoms either directly or through a linking group or atom to the coupling position of the coupler. The silyl substituent bears three groups which are independently aromatic groups, heterocyclic groups, aliphatic groups or additional silyl groups bonded through a linking atom to the silicon atom in said silyl substituent.Type: GrantFiled: December 7, 1992Date of Patent: June 7, 1994Assignee: Eastman Kodak CompanyInventor: Sundaram Krishnamurthy
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Patent number: 5302504Abstract: A silver halide color photographic material which comprises a coupler is disclosed. The coupler is represented by a formula I or II, ##STR1## The meaning of each symbol is defined in the specification. The color photographic material of the invention gives a magenta image excellent in preserving stability.Type: GrantFiled: September 16, 1991Date of Patent: April 12, 1994Assignee: Konica CorporationInventors: Shuji Kida, Hidenubu Ohya
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Patent number: 5302496Abstract: Novel pyrazoloazole dye-forming couplers contain on the azole ring a group containing a carbon atom bonded directly to the azole ring and wherein this carbon atom is bonded directly to a nitrogen atom in the group. Such couplers provide advantageous bathochromic hue shift in dyes formed from the couplers. These couplers are useful in photographic silver halide materials and processes.Type: GrantFiled: September 18, 1992Date of Patent: April 12, 1994Assignee: Eastman Kodak CompanyInventors: Robert F. Romanet, Teh-Hsuan Chen
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Patent number: 5300407Abstract: An image forming method is disclosed which comprises developing a silver halide photographic material with a developing solution containing an aromatic primary amine developing agent in the presence of an imidazo[1,2-b]pyrazole type coupler represented by the following general formula (I): ##STR1## wherein R.sub.1 represents a hydrogen atom, an alkyl group, an alkoxy group, an aryloxy group or an aryl group; R.sub.2 represents an alkoxy group, an aryloxy group or an amino group; R.sub.3 represents a hydrogen atom, an alkyl group or an aryl group; and X represents a hydrogen atom or a group capable of being released upon coupling with an oxidation product of an aromatic primary amine developing agent.The magenta coupler represented by general formula (I) is excellent in color reproducibility, sensitivity and color density.A silver halide color photographic material containing the magenta coupler is also disclosed.Type: GrantFiled: December 2, 1991Date of Patent: April 5, 1994Assignee: Fuji Photo Film Co., Ltd.Inventors: Koshin Matsuoka, Tadahisa Sato
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Patent number: 5298368Abstract: Photographic coupler compositions comprise (a) a pyrazolone magenta dye-forming coupler compound, and (b) a sulfoxide compound in an amount sufficient to reduce continued coupling of the coupler compound during the bleach step of a color photographic process. The sulfoxide compound is of the formula ##STR1## wherein R.sub.1 and R.sub.2 are individually selected from the group consisting of straight and branched chain alkyl groups, alkenyl groups and alkylene groups; straight and branched chain alkyl groups, alkenyl groups and alkylene groups containing at least one substituent selected from the group consisting of alkoxy, aryloxy, aryl, alkoxycarbonyl, aryloxycarbonyl, acyloxy, carbonamido and carbamoyl groups and halogen atoms; a phenyl group; and a phenyl group containing at least one substituent selected from the group consisting of alkyl, alkoxy, aryloxy, aryl, alkoxycarbonyl, aryloxycarbonyl, acyloxy, carbonamido and carbamoyl groups and halogen atoms. Additionally, R.sub.1 and R.sub.Type: GrantFiled: April 23, 1991Date of Patent: March 29, 1994Assignee: Eastman Kodak CompanyInventors: Paul B. Merkel, Edward Schofield, Stephen P. Singer
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Patent number: 5288597Abstract: A method of forming a color image which comprises providing a silver halide color photographic material including a support having thereon at least one photosensitive layer containing at least one coupler which forms a dye upon a coupling reaction with an oxidized product of an aromatic primary amine color developing agent and a substantially silver iodide-free silver halide emulsion containing at least 90 mol. % of silver chloride, which silver halide color photographic material further contains at least one compound of the following formula (I) or (II), and subjecting said silver halide color photographic material to imagewise exposure and then to development with a substantially benzyl alcohol-free developer for not less than 90 seconds.Type: GrantFiled: June 3, 1993Date of Patent: February 22, 1994Assignee: Fuji Photo Film Co., Ltd.Inventor: Yasuhiro Hayashi
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Patent number: 5273864Abstract: This invention provides a processing method for an exposed silver halide color photographic material, which enables cut-down of the times required for bleaching-and-fixing and for washing and yet affords a stable image excellent in color reproduction. The processing method of this invention is characterized in that the silver halide color photographic material is developed with a color developing solution substantially free of benzyl alcohol, and that the thus developed photographic material is subjected to bleaching-and-fixing for a time of not more than 70 seconds and then subjected to washing for a time of not more than 70 seconds. Another important aspect of the invention resides in the use of a magenta coupler in the processing method with a merit that a stable colored image having excellent hue is developed without the fear of formation of stains although the times for the bleaching-and-fixing and for the washing are shortened remarkedly.Type: GrantFiled: May 29, 1990Date of Patent: December 28, 1993Assignee: Fuji Photo Film Co., Ltd.Inventors: Takatoshi Ishikawa, Nobuo Sakai, Minoru Sakai
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Patent number: 5262292Abstract: Pyrazolone magenta dye-forming couplers having a particular arylthio coupling-off group enhance the photographic properties and improve the manufacturing and handling characteristics of materials and processes employing such couplers. The coupler contains an N-phenyl group, a 3-anilino group and a 4-(arylthio) coupling off group containing a particular aryloxymethylacylamino group as an ortho substituent. A broad range of improvements are realized including stability, reactivity, hue, and dye density in addition to simplified and safer manufacture.Type: GrantFiled: April 23, 1992Date of Patent: November 16, 1993Assignee: Eastman Kodak CompanyInventors: Sundaram Krishnamurthy, Thomas A. Rosiek, Vincent J. Flow, David S. Bailey, David J. Giacherio, John L. Pawlak, Stephen P. Singer
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Patent number: 5256529Abstract: A magenta dye-forming pyrazolotriazole coupler solubilized by one or two sulfonamido groups results in a coupler having increased coupling activity, low fog and good dispersability. The couplers are useful in photographic elements and react with oxidized silver halide to form dyes, and/or to release photographically useful groups.Type: GrantFiled: July 27, 1992Date of Patent: October 26, 1993Assignee: Eastman Kodak CompanyInventors: Robert F. Romanet, Hans G. Ling, David Hoke
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Patent number: 5256528Abstract: A photographic element and process provide a magenta coupler of the formula: ##STR1## wherein (a) at least one of X1, X2 and R1 and at least one of R2 and R3 is a substituent individually selected from carbamoyl, alkoxycarbonyl, aryloxycarbonyl, sulfamoyl, alkylsulfonyl, arylsulfonyl, alkoxysulfonyl, aryloxysulfonyl, alkylsulfoxyl, arylsulfoxyl, acyloxy, cyano, nitro, and trifluoromethyl;(b) the substituents X1, X2, R1, R2 and R3 not selected from the (a) group may be selected from alkyl, alkoxy, aryloxy, acylamino, alkylthio, arylthio, sulfonamido, alkylureido, arylureido, alkoxycarbonylamino, aryloxycarbonylamino, and halogen and in the case of R3 hydrogen;(c) substituents R1 and R2 are para or meta to the carbon attached to the nitrogen atom;(d) a and b are 1 to 3;(e) Q is an alkylthio or arylthio coupling-off group.The element provides a deeper magenta hue and reduced blue absorption by the resulting magenta dye.Type: GrantFiled: April 23, 1992Date of Patent: October 26, 1993Assignee: Eastman Kodak CompanyInventors: Paul B. Merkel, Stephen P. Singer, Bernard Arthur Clark, Paul Louis R. Stanley
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Patent number: 5254451Abstract: A silver halide color photographic light sensitive material comprising a magenta represented by Formula I-3 or I-4 is disclosed. ##STR1## R.sub.1, R.sub.2 and R.sub.4 represent each a substituent; X represents a hydrogen atom or a group capable of splitting off;Y represents a group consisting of non-metal atoms necessary to form a 5- or 6-membered heterocyclic ring;m is 1 or 2; andn is 0 to 4.The invention provides a silver halide color photographic light sensitive material having exellent color reproducibility and color producibility, in which material stability against light of magenta dye image is remarbly improved.Type: GrantFiled: September 22, 1992Date of Patent: October 19, 1993Assignee: Konica CorporationInventors: Hiroshi Kita, Yutaka Kaneko, Noboru Mizukura, Toru Kubota
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Patent number: 5250400Abstract: Novel pyrazolotriazole couplers containing a ballast group of formula (I): ##STR1## are useful in photographic materials and processes. The couplers exhibit increased coupling activity, and provide formation of dyes having improved maximum magenta image dye density, contrast, and development speed when employed in color photographic materials and processes.Type: GrantFiled: February 26, 1992Date of Patent: October 5, 1993Assignee: Eastman Kodak CompanyInventors: Sundaram Krishnamurthy, Ping-Wah Tang, Stanley W. Cowan
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Patent number: 5250405Abstract: Color photographic materials comprise a support bearing a silver halide emulsion and a coupler composition. The coupler composition comprises a two-equivalent pyrazolone magenta dye-forming coupler, a ballasted carbonamide compound, and a developer inhibitor-releasing coupler. The carbonamide compound reduces continued coupling of the pyrazolone magenta dye-forming coupler during the bleach step in a color photographic process without altering the advantageous properties provided by the combination of the two-equivalent pyrazolone magenta dye-forming coupler and the developer inhibitor-releasing coupler.Type: GrantFiled: August 29, 1991Date of Patent: October 5, 1993Assignee: Eastman Kodak CompanyInventors: Paul B. Merkel, Stephen P. Singer
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Patent number: 5246820Abstract: A photographic element having improved granularity contains a dye-forming coupler containing a carbamic acid precursor capable of being converted into a carbamic acid group during processing, and wherein after processing the carbamic acid group decomposes, leaving the dye substantially non-diffusable.Type: GrantFiled: March 3, 1992Date of Patent: September 21, 1993Assignee: Eastman Kodak CompanyInventors: Jared B. Mooberry, James J. Seifert, Stephen P. Singer
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Patent number: 5246819Abstract: In accordance with the present invention a method for continuously processing a silver halide color photographic material with a color developer containing at least one aromatic primary amine color-developing agent is disclosed. The silver halide color photographic material at least one of the layers of which contains a silver halide emulsion of a high chloride comprising 80 mol % or over of silver chloride is processed, after exposure to light, with the replenishing amount of the color developer being 20 to 120 ml per m.sup.2 of the silver halide photographic material. The silver halide photographic material contains at least one of pyrazoloazole magenta couplers.Type: GrantFiled: July 25, 1991Date of Patent: September 21, 1993Assignee: Fuji Photo Film Co., Ltd.Inventors: Kazuaki Yoshida, Takatoshi Ishikawa
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Patent number: 5242789Abstract: A silver halide photographic material comprising a support having thereon a silver halide emulsion layer containing at least one coupler represented by the following formulae (I) and (II): ##STR1## wherein R.sub.1 represents an alkyl group, an aryl group or a heterocyclic group; R.sub.2 or R'.sub.2 represents an alkyl group, an aryl group; and X represents a coupling split-off group liked through a nitrogen or a sulfur atom.Type: GrantFiled: June 22, 1990Date of Patent: September 7, 1993Assignee: Fuji Photo Film Co., Ltd.Inventors: Tadahisa Sato, Nobuo Furutachi
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Patent number: 5234805Abstract: Pyrazolotriazole couplers having a ballast-containing group of the formula (I) attached to the pyrazolotriazole ring group ##STR1## wherein: R, R.sup.2, R.sup.a and R.sup.b represent hydrogen or a substituent;L is a divalent linking group connecting the ballast containing group to the pyrazolotriazole ring;L' is a linking group connecting the --BD group to the phenylene ring;n is 0 or 1;B represents --N(R.sup.c)--SO.sub.2 --, wherein R.sup.c represents hydrogen or a substituent; andD represents substituted or unsubstituted alkyl are useful in silver halide photographic materials and processes. The couplers exhibit increased coupling efficiency, and provide formation of dyes having improved maximum magenta image dye density when employed in color photographic materials and processes.Type: GrantFiled: February 26, 1992Date of Patent: August 10, 1993Assignee: Eastman Kodak CorporationInventors: Ping-Wah Tang, Sundaram Krishnamurthy, Stanley W. Cowan
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Patent number: 5232821Abstract: Photographic coupler compositions comprise (a) a magenta dye-forming coupler compound, and (b) a sulfoxide compound or a sulfone compound in an amount sufficient to improve the light stability of a magenta dye formed from the magenta dye-forming coupler compound. The sulfoxide compound is of the formula ##STR1## and the sulfone compound is of the formula ##STR2## wherein R.sub.1 and R.sub.Type: GrantFiled: April 1, 1991Date of Patent: August 3, 1993Assignee: Eastman Kodak CompanyInventors: Paul B. Merkel, Edward Schofield
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Patent number: 5215872Abstract: A method of processing a silver halide color photographic material is disclosed, comprising a support having provided thereon at least one light-sensitive emulsion layer, which comprises the steps of color developing the material with a developer to which a replenisher is added and bleaching the developed material, wherein the material contains a coupler represented by the following general formula (I) and the amount of replenisher added to the color developer is 600 ml or less per m.sup.2 of the material: ##STR1## wherein A represents a coupler group, and when A is a phenol or naphthol coupler group, n is 1, and when A is any other coupler group, n is 0; and R represents an alkyl group having from 1 to 4 carbon atoms, or a pyridyl group. Images having excellent photographic characteristics are obtained by the method even though the amount of the replenisher is reduced.Type: GrantFiled: April 16, 1991Date of Patent: June 1, 1993Assignee: Fuji Photo Film Co., Ltd.Inventors: Masatoshi Goto, Keiji Mihayashi
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Patent number: 5206129Abstract: Disclosed is a dye forming coupler represented by formula (I): ##STR1## wherein R.sup.1 and R.sup.2, which may be the same or different, each represents a substituent group, and X is a hydrogen atom or a group which can be eliminated by a coupling reaction with the oxidized species of a primary aromatic amine derivative.Type: GrantFiled: November 7, 1991Date of Patent: April 27, 1993Assignee: Fuji Photo Film Co., Ltd.Inventors: Kozo Sato, Kiyoshi Takeuchi, Yoshio Ishii