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EP0309160A1 - Photographisches Eintragungsmaterial, enthaltend eine farbbildbildende Kupplerverbindung - Google Patents

Photographisches Eintragungsmaterial, enthaltend eine farbbildbildende Kupplerverbindung Download PDF

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Publication number
EP0309160A1
EP0309160A1 EP88308570A EP88308570A EP0309160A1 EP 0309160 A1 EP0309160 A1 EP 0309160A1 EP 88308570 A EP88308570 A EP 88308570A EP 88308570 A EP88308570 A EP 88308570A EP 0309160 A1 EP0309160 A1 EP 0309160A1
Authority
EP
European Patent Office
Prior art keywords
recording material
coupler
photographic recording
compound
dye
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP88308570A
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English (en)
French (fr)
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EP0309160B1 (de
Inventor
Paul Barrett C/O Eastman Kodak Company Merkel
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Eastman Kodak Co
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Eastman Kodak Co
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Filing date
Publication date
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Priority to AT88308570T priority Critical patent/ATE84886T1/de
Publication of EP0309160A1 publication Critical patent/EP0309160A1/de
Application granted granted Critical
Publication of EP0309160B1 publication Critical patent/EP0309160B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/392—Additives
    • G03C7/39208—Organic compounds
    • G03C7/39236—Organic compounds with a function having at least two elements among nitrogen, sulfur or oxygen

Definitions

  • This invention relates to a color photographic silver halide recording material.
  • the invention relates to an improved photographic recording material containing dye image-forming coupler compounds.
  • Color photographic recording materials generally contain silver halide emulsion layers sensitized to each of the blue, green and red regions of the visible spectrum, with each layer having associated therewith a color-forming compound which, respectively, yields a yellow, magenta or cyan dye.
  • the quality of the resulting color image is primarily based on the dye hues obtained from the respective color-forming compounds.
  • Dye image-forming coupler compounds are frequently employed to provide the desired color image.
  • a problem encountered with such couplers is that the spectral absorption characteristics of dyes obtained therefrom may not have the particular absorption maxima and distribution that are desired. Frequently, a dye which is obtained may have an absorption maximum as little as several nanometers removed from the optimum desired value, and therefore will not have the desired hue, notwithstanding this slight difference in absorption characteristics.
  • Coupler solvents are known to cause shifts in absorption values of dyes.
  • U.S. Patent 3,676,137 describes use of a phosphate ester of a high boiling coupler solvent to shift absorption of a cyan dye to a shorter wavelength in order to reduce excessive red wavelength absorption.
  • shifting absorption of a pyrazolone azomethine dye to a longer wavelength by use of a phenolic compound is known from Journal of the American Chemical Society , 73 , 919 (1951).
  • British Patent Specification 1,076,054 describes a method for incorporating color couplers in gelatin-silver halide emulsions using a combination of a solvent miscible with alkaline solution and a water insoluble organic liquid having a boiling point above 150°C.
  • the insoluble organic liquid can be a hydrocarbon, an ether, an ester, a ketone, an alcohol, an amide as well as various polymeric materials.
  • the amide which is disclosed is N,N-dibutyllauramide.
  • the object of the present invention is to provide a color photographic silver halide recording material having the capability of altering the spectral absorption properties of dyes so that absorption values thereof can be shifted over both broad and narrow ranges as compared with the inherent absorption characteristics of the dyes.
  • a color photo­graphic recording material which comprises a support having thereon a light-sensitive silver halide emulsion layer, a coupler compound which is
  • This invention also relates to a color photographic record comprising a dye formed by a coupling reaction between a dye forming coupler and oxidized silver halide developing agent, which record comprises, in association with the dye, a carbonamide compound having the structural formula: wherein; R1 is a substituted or unsubstituted alkyl or an electron withdrawing group; R2 is a substituted or unsubstituted aryl group or a substituted or unsubstituted alkyl group which is free of carboxylic group substitution; and n is 0 to 3.
  • Electron-withdrawing groups represented by R1 include -CN, -NO2, a halogen atom, - NHR3, - R3 and -SO2R3, where R3 is a substituted or unsubstituted alkyl or a substituted or unsubstituted aryl group.
  • the alkyl groups which can be represented by R1, R2 or R3 can have from 1 to about 20 carbon atoms. Preferred alkyl groups have from 1 to about 12 carbon atoms. Such groups can be straight or branched chain and can be substituted.
  • the aryl groups which can be represented by R2 or R3 can have from about 6 to about 12 carbon atoms and can be substituted.
  • Substituents which can be present on the R1, R2 and R3 groups include other alkyl groups having the 1 to 6 carbon atoms, and halogen atoms. Chlorine is a preferred halogen substituent, particularly on an aryl ring inasmuch as it provides good stability properties and is least expensive to manufacture.
  • the described carbonamide compounds can by synthesized by reacting an aliphatic or an aromatic acid chloride compound having the formula R2COCl with a primary aromatic amine compound of the formula: where R1, R2, R3 and n have the meanings as described above, according to procedures known in the chemical art.
  • the quantity of carbonamide compound, with respect to each part by weight of the coupler be from about 0.05 to about 10 parts, preferably from about 0.2 to about 3 parts by weight of the coupler compound.
  • the amount of carbonamide compound increases, relative to the amount of coupler compound employed, there is usually a detectable increase in the extent of hue shift in the image dye.
  • the particular choice of coupler, of carbonamide compound or the presence of one or more coupler solvents all tend to influence the type and the extent of spectral absorption change in the resulting image dye.
  • Two or more carbonamide compounds may be used in combination to alter the spectral absorption properties of dyes as described herein.
  • the coupler compound When the coupler compound is added to a silver halide emulsion, conventional procedures may be employed.
  • the coupler can first be dissolved in one or more known coupler solvents, such as di-n-butyl phthalate (DBP), and then be mixed with a carbonamide compound as described herein.
  • the coupler compound can be mixed with a carbonamide compound where these compounds are sufficiently compatible, so that known coupler solvents may not be needed.
  • the resulting mixture or solution is then dispersed in aqueous gelatin, preferably containing a surfactant, and the dispersion is added to a silver halide emulsion which can then be coated by known techniques.
  • Preferred carbonamide compounds which are useful for shifting absorption values of dyes include the following:
  • Couplers which form cyan dyes upon reaction with oxidized color developing agents are described in such representative patents and publications as U.S. Patent Nos. 2,474,293; 2,772,162; 2,801,171; 2,895,826; 3,002,836; 3,419,390; 3,476,563; 3,779,763; 3,996,253; 4,124,396; 4,248,962; 4,254,212; 4,296,200; 4,333,999; 4,443,536; 4,457,559; 4,500,635; and 4,526,864, the disclosures of which are incorporated herein by reference.
  • Preferred cyan coupler structures are phenols and naphthols which form cyan dyes on reaction with oxidized color developing agent. These preferred structures include the following moieties: where R4 represents a ballast group, R5 represents one or more halogen atoms (e.g., chloro, fluoro), lower alkyl (e.g., methyl, ethyl, butyl) or lower alkoxy (e.g., methoxy, ethoxy, butoxy) groups and X is hydrogen or a coupling off group.
  • R4 represents a ballast group
  • R5 represents one or more halogen atoms (e.g., chloro, fluoro)
  • lower alkyl e.g., methyl, ethyl, butyl
  • lower alkoxy e.g., methoxy, ethoxy, butoxy
  • X is hydrogen or a coupling off group.
  • R4 on a C-3 type coupler structure is the group such as is described in US Patent 4,333,999.
  • Magenta dye image-forming couplers which are not aldehydebis 5-pyrazolone or pyrazolino-[1,5-a)-benzimidazole magenta type couplers, which form magenta dyes upon reaction with oxidized color developing agents are described in such representative patents and publications as: U.S. Patent Nos. 1,969,479; 2,311,082; 2,343,703; 2,369,489; 2,600,788; 2,908,573; 3,061,432; 3,062,653; 3,152,896; 3,519,429; 3,725,067; 4,120,723; 4,500,630; 4,540,654 and 4,581,326; and European Patent Publication Nos.
  • Preferred magenta couplers include pyrazolones compounds having the structural formulae: pyrazolotriazole compounds having the structural formulae: pyrazolobenzimidazole compounds having the structural formulae: and indazole compounds having the structural formula: wherein X is as defined above; R4 is a ballast group; R6 is halogen (e.g., chloro, fluoro), alkyl or alkoxy having from 1 to 4 carbon atoms, phenyl or substituted phenyl (e.g., 2,4,6-trihalophenyl); R7 is hydrogen or a monovalent organic radical, for example a saturated or unsaturated alkyl group having from 1 to about 20 carbon atoms (methyl, ethyl, propyl, butyl, decyl, dodecyl, heptadecyl, octadecyl); a cycloalkyl group (e.g.
  • cyclohexyl an aralkyl group (e.g. benzyl); an aryl group (e.g. phenyl, alkoxyphenyl in which the alkyl or alkoxy radical has from 1 to about 20 carbon atoms, nitrophenyl, aminophenyl, acylaminophenyl, alkyl­aminophenyl, naphthyl, diphenyl, diphenylether, diphenylthioether); a heterocyclic group (e.g.
  • a-furyl, a-benzofuryl, a-pyridyl an amino, hydroxy or carboxylic acid group, it being possible for the hydrogen atoms of these groups to be substituted, for instance by a mono- or dialkylamino group in which the alkyl groups have from 1 to about 20 carbon atoms; a cycloalkylamino group; an amino group in which one hydrogen atom is replaced by a pyrazolo-[1,5-a]-benzimidazolyl radical which is bonded in 3- position to said nitrogen atom so that couplers result in which two pyrazolo-[1,5-a]-benz­imidazolyl radicals are connected by an amino group, and in which the remaining hydrogen atom may be replaced by a substituent such as an alkyl-, aryl-, aralkyl- or acyl- radical; an acylamino group in which the acyl radical is derived from an aliphatic, aromatic or heterocyclic carboxylic
  • R13 can be an aromatic or heterocyclic radical (phenyl, naphthyl, diphenyl, diphenylether, benzthiazolyl, pyridyl, quinolyl or pyrazolyl) which may be substituted such as by an alkyl group having from 1 to about 20 carbon atoms, hydroxy, alkoxy, halogen, amino, substituted amino, nitro, sulphonic acid or carboxylic acid groups;
  • R9 represents a divalent radical such as wherein R10 can be alkyl, aralkyl, especially phenyl, phenyl substituted preferably in the p-­position by a tertiary amino group such as a dialkylamino group in which at least one of the alkyl groups is substituted by carboxy, sulpho, hydroxy, alkoxy, carboxylalkyl, cyano or the divalent radical wherein R11 and R12 represent alipha-phenyl, naphthyl, diphenyl
  • magenta dye forming coupler compounds which are useful in the practice of this invention include:
  • Couplers which form yellow dyes upon reaction with oxidized color developing agent are described in such representative U. S. Patents as Nos. 2,298,443; 2,875,057, 2,407,210; 3,265,506; 3,384,657; 3,408,194; 3,415,652; 3,447,928; 3,542,840; 4,046,575; 3,894,875; 4,095,983; 4,182,630; 4,203,768; 4,221,860; 4,326,024; 4,401,752; 4,443,536; 4,529,691; 4,587,205; 4,587,207 and 4,617,256 the disclosures of which are incorporated herein by reference.
  • Preferred yellow dye image-forming couplers are acylacetamides, such as benzoylacetanilides and pivalylacetanilides. Structures of such preferred coupler moieties are: where R13 is as defined above R14 is hydrogen or one or more halogen, lower alkyl (e.g. methyl, ethyl) or a ballast (e.g. alkoxy of 16 to 20 carbon atoms) group and X is a coupling off group.
  • Photographic elements in which the photographic couplers of this invention are incorporated can be simple elements comprising a support and a single silver halide emulsion layer, or they can be multilayer, multicolor elements.
  • the coupler compounds of this invention can be incorpo­rated in the silver halide emulsion layer or in another layer, such as adjacent layer, where they will come into reactive association with oxidized color developing agent which has developed silver halide in the emulsion layer.
  • the silver halide emulsion layer can contain, or have associated therewith, other photographic coupler compounds, such as color forming couplers, colored masking couplers, etc. These other photographic coupler compounds can form dyes of the same or different color and hue as the photographic coupler compounds of this invention. Additionally, the silver halide emulsion layer can contain addenda conventionally contained in such layers.
  • a typical multilayer, multicolor photographic element comprises a support having thereon a red-sensitive silver halide emulsion layer having associated therewith a cyan dye image-forming coupler compound, a green-sensitive silver halide emulsion layer having associated therewith a magenta dye image-forming coupler compound and a blue-sensitive silver halide emulsion layer having associated therewith a yellow dye image-forming coupler compound, wherein at least one dye image-forming coupler compound has associated therewith a carbonamide compound as described herein.
  • Each silver halide emulsion layer can be composed of one or more layers and the layers can be arranged in different locations with respect to one another. Typical arrangements are described in U.S. Patent Nos. 3,227,554; 3,620,747; 3,843,369; and 4,400,463 and in U.S. Patent No. 923,045.
  • the light sensitive silver halide emulsions can include coarse, regular or fine grain silver halide crystals or mixtures thereof and can be comprised of such silver halides as silver chloride, silver bromide, silver bromoiodide, silver chlorobromide, silver chloroiodide, silver chlorobromoiodide and mixtures thereof.
  • the emulsions can be negative-working or direc-positive emulsions. They can form latent images predominantly on the surface of the silver halide grains or predominantly on the interior of the silver halide grains. They can be chemically and spectrally sensitized.
  • the emulsions typically will be gelatin emulsions although other hydrophilic colloids can be used in accordance with usual practice.
  • the support can be of any suitable material used with photographic elements.
  • a flexible support is employed, such as a polymeric film or paper support.
  • Such supports include cellulose nitrate, cellulose acetate, polyvinyl­acetal, polyethylene terephthalate, polycarbonate and resinous materials as well as glass, paper or metal.
  • Paper supports can be acetylated or coated with baryta and/or an a-olefin polymer, particularly a polymer of an a-olefin containing 2 to 10 carbon atoms such as polyethylene, polypropylene or ethylene-butene copolymers.
  • association and “associated with” are intended to mean that materials can be in either the same or different layers so long as the materials are accessible to one another.
  • Dyes were dissolved in the coupler solvent, di-n-butyl phthalate (DBP), with or without a carbonamide compound, and coated in a gelatin vehicle in single layers.
  • DBP di-n-butyl phthalate
  • This mixture was passed five times through a colloid mill and 0.2 ml (10% solution) Olin Corp. 10G surfactant and 0.05 ml (5% solution) formaldehyde were added.
  • the milled mixture was then coated on a poly(ethyleneterephthalate) support, 100 mm wet thickness, and dried at 49°C. After 24 hours, the coating was washed for 5 minutes, dried, and spectrophotometric absorption maxima values were obtained.
  • hue shifts to longer wavelengths vary from only a few nanometers to as much as 16 nanometers depending upon the dye and the carbonamide compound used. These variations in wavelength shifts offer a high degree of manipulative control and provide an excellent, inexpensive means to obtain particularly desired hue values with a variety of dye types.

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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
EP88308570A 1987-09-21 1988-09-16 Photographisches Eintragungsmaterial, enthaltend eine farbbildbildende Kupplerverbindung Expired - Lifetime EP0309160B1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT88308570T ATE84886T1 (de) 1987-09-21 1988-09-16 Photographisches eintragungsmaterial, enthaltend eine farbbildbildende kupplerverbindung.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US9917287A 1987-09-21 1987-09-21
US99172 1987-09-21

Publications (2)

Publication Number Publication Date
EP0309160A1 true EP0309160A1 (de) 1989-03-29
EP0309160B1 EP0309160B1 (de) 1993-01-20

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EP88308570A Expired - Lifetime EP0309160B1 (de) 1987-09-21 1988-09-16 Photographisches Eintragungsmaterial, enthaltend eine farbbildbildende Kupplerverbindung

Country Status (5)

Country Link
EP (1) EP0309160B1 (de)
JP (1) JPH01101548A (de)
AT (1) ATE84886T1 (de)
DE (1) DE3877673T2 (de)
ES (1) ES2053752T3 (de)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0399541A2 (de) * 1989-05-25 1990-11-28 Fuji Photo Film Co., Ltd. Farbphotographisches Silberhalogenidmaterial
EP0523640A1 (de) * 1991-07-15 1993-01-20 Eastman Kodak Company Photographische Kupplerzusammensetzungen, die Carbonamide enthalten, sowie Verfahren
US5593816A (en) * 1993-01-11 1997-01-14 Fuji Photo Film Co., Ltd. Silver halide color photographic material and color image forming method
EP0800113A2 (de) 1996-04-05 1997-10-08 Fuji Photo Film Co., Ltd. Photographisches lichtempfindliches Silberhalogenidfarbmaterial
WO2012014955A1 (ja) 2010-07-30 2012-02-02 富士フイルム株式会社 新規なアゾ化合物、水溶液、インク組成物、インクジェット記録用インク、インクジェット記録方法、インクジェット記録用インクカートリッジ、及びインクジェット記録物
WO2012014954A1 (ja) 2010-07-30 2012-02-02 富士フイルム株式会社 新規なアゾ化合物、水溶液、インク組成物、インクジェット記録用インク、インクジェット記録方法、インクジェット記録用インクカートリッジ、及びインクジェット記録物
EP2455431A1 (de) 2003-10-23 2012-05-23 Fujifilm Corporation Tinte und Tintensatz zur Tintenstrahlaufzeichnung
EP2712894A1 (de) 2012-09-26 2014-04-02 Fujifilm Corporation Azoverbindung, wässrige Lösung, Tintenzusammensetzung, Tinte zur Tintenstrahlaufzeichnung, Tintenstrahlaufzeichnungsverfahren, Tintenpatrone zur Tintenstrahlaufzeichnung und tintenstrahlaufzeichnetes Material

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1076054A (en) * 1965-03-30 1967-07-19 Ilford Ltd Production of colour photographic materials
EP0268496A2 (de) * 1986-11-19 1988-05-25 Konica Corporation Lichtempfindliches, photographisches Silberhalogenidmaterial zur Verwendung in einer schnellen Behandlung

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1076054A (en) * 1965-03-30 1967-07-19 Ilford Ltd Production of colour photographic materials
EP0268496A2 (de) * 1986-11-19 1988-05-25 Konica Corporation Lichtempfindliches, photographisches Silberhalogenidmaterial zur Verwendung in einer schnellen Behandlung

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0399541A2 (de) * 1989-05-25 1990-11-28 Fuji Photo Film Co., Ltd. Farbphotographisches Silberhalogenidmaterial
EP0399541A3 (de) * 1989-05-25 1991-04-03 Fuji Photo Film Co., Ltd. Farbphotographisches Silberhalogenidmaterial
US5120636A (en) * 1989-05-25 1992-06-09 Fuji Photo Film Co., Ltd. Silver halide color photographic material containing magenta coupler, specific organic solvent and bisphenol compound
EP0523640A1 (de) * 1991-07-15 1993-01-20 Eastman Kodak Company Photographische Kupplerzusammensetzungen, die Carbonamide enthalten, sowie Verfahren
US5258278A (en) * 1991-07-15 1993-11-02 Eastman Kodak Company Color photographic material containing a coupler composition comprising a pyrazoldtriazole magenta coupler and a carbonamide compound
US5593816A (en) * 1993-01-11 1997-01-14 Fuji Photo Film Co., Ltd. Silver halide color photographic material and color image forming method
EP0800113A2 (de) 1996-04-05 1997-10-08 Fuji Photo Film Co., Ltd. Photographisches lichtempfindliches Silberhalogenidfarbmaterial
US6045987A (en) * 1996-04-05 2000-04-04 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive material
EP2455431A1 (de) 2003-10-23 2012-05-23 Fujifilm Corporation Tinte und Tintensatz zur Tintenstrahlaufzeichnung
WO2012014955A1 (ja) 2010-07-30 2012-02-02 富士フイルム株式会社 新規なアゾ化合物、水溶液、インク組成物、インクジェット記録用インク、インクジェット記録方法、インクジェット記録用インクカートリッジ、及びインクジェット記録物
WO2012014954A1 (ja) 2010-07-30 2012-02-02 富士フイルム株式会社 新規なアゾ化合物、水溶液、インク組成物、インクジェット記録用インク、インクジェット記録方法、インクジェット記録用インクカートリッジ、及びインクジェット記録物
EP2712894A1 (de) 2012-09-26 2014-04-02 Fujifilm Corporation Azoverbindung, wässrige Lösung, Tintenzusammensetzung, Tinte zur Tintenstrahlaufzeichnung, Tintenstrahlaufzeichnungsverfahren, Tintenpatrone zur Tintenstrahlaufzeichnung und tintenstrahlaufzeichnetes Material

Also Published As

Publication number Publication date
JPH01101548A (ja) 1989-04-19
ATE84886T1 (de) 1993-02-15
ES2053752T3 (es) 1994-08-01
DE3877673T2 (de) 1993-08-05
EP0309160B1 (de) 1993-01-20
DE3877673D1 (de) 1993-03-04

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