EP0708933A1 - Element photographique possedant une dispersion particulaire solide d'un piegeur de revelateur oxyde - Google Patents

Element photographique possedant une dispersion particulaire solide d'un piegeur de revelateur oxyde

Info

Publication number
EP0708933A1
EP0708933A1 EP94922427A EP94922427A EP0708933A1 EP 0708933 A1 EP0708933 A1 EP 0708933A1 EP 94922427 A EP94922427 A EP 94922427A EP 94922427 A EP94922427 A EP 94922427A EP 0708933 A1 EP0708933 A1 EP 0708933A1
Authority
EP
European Patent Office
Prior art keywords
dispersion
oxidized developer
scavenger
crystalline solid
hydrazide
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.)
Ceased
Application number
EP94922427A
Other languages
German (de)
English (en)
Inventor
Mary Christine Brick
Norma Bettina Platt
Paul Leo Zengerle
Jeffrey Louis Hall
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eastman Kodak Co
Original Assignee
Eastman Kodak Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Publication of EP0708933A1 publication Critical patent/EP0708933A1/fr
Ceased legal-status Critical Current

Links

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
    • 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
    • G03C1/00—Photosensitive materials
    • G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein

Definitions

  • This invention relates to the use of hydrazide oxidized developer scavengers in photographic elements.
  • One aspect of this invention comprises a photographic element comprising a support having thereon at least one silver halide emulsion layer, and a layer, which is the same or different from the silver halide layer, comprising crystalline solid particles consisting essentially of a hydrazide oxidized developer scavenger dispersed in a binder.
  • Another aspect of this invention comprises a process for preparing a crystalline solid particle dispersion of a hydrazide oxidized developer scavenger, comprising the steps of : (a) milling crystalline solid particles of the hydrazide oxidized developer scavenger in an aqueous medium in the presence of a dispersing agent and in the substantial absence of an organic solvent to form a first dispersion; and (b) adding the first dispersion to an aqueous medium comprising a binder to form a second dispersion.
  • a further aspect of this invention comprises a process for preparing a photographic element which comprises the steps of:
  • This invention provides a way of improving the utilization of hydrazide oxidized developer scavengers.
  • the stability of the oxidized developer scavenger dispersion during melt coating operations is improved when the hydrazide is in the form of a crystalline solid particle dispersion.
  • hydrazide oxidized developer scavengers are used as conventional oil-in-water dispersions, and their use in the form of crystalline solid particle dispersions has not, up to now, been described or suggested.
  • hydroquinone derivative oxidized developer scavengers incorporated in a photographic element in the form of conventional oil- in-water dispersions suffer from oxidative instability which is reduced if the hydroquinone is incorporated in the form of a crystalline solid particle dispersion.
  • Hydrazide derivative oxidized developer scavengers do not suffer from oxidative instability when dispersed as conventional oil-in-water dispersions.
  • hydrazide oxidized developer scavengers useful in the practice of the present invention are well known and can be prepared by synthesis techniques known in the art.
  • Preferred hydrazide scavengers are of the general formula
  • Rl represents an electron donating group
  • R ⁇ represents a hydrogen atom or an alkyl, alkoxy, aryl, aryloxy, aralkyl or amino group
  • n is an interger from 1 to 5.
  • Particularly preferred hydrazide scavengers are compounds of the formula:
  • the scavenger compounds should be crystalline solids and substantially water insoluble at coating conditions, which generally involve temperatures from 10 C to 50 C, and pH from 5.0 to 7.0.
  • the crystalline solid particle dispersion can be formed by precipitating or reprecipitating the compound in the form of a dispersion in the presence of one or more dispersing agents, or by well known milling techniques. Reprecipitating techniques which involve dissolving the scavenger and precipitating by changing the solvent and/or pH in the presence of a dispersing agent are well known in the art. Reprecipitating techniques are described, for example, in US Application Serial No. 07/812,503 by Texter, et al, filed 12/20/91, and are herein incorporated by reference.
  • Milling techniques are also well known in the art, and examples include ball milling, media milling, attritor milling, jet milling or colloid milling the scavenger in the presence of a dispersing agent.
  • the dispersing agent is preferably an anionic, nonionic or zwitterionic surfactant, or a water soluble homopolymer or copolymer. Mixtures of two or more dispersing agents can be used in the practice of this invention.
  • the total amount of dispersing agent can vary over a wide range, generally from about 1% to about 200%, preferably about 5% to about 100%, the percentages being by weight, based on the weight of the scavenger.
  • Particularly preferred dispersing agents are an alkali metal salt of an alkarylene sulfonic acid, such as the sodium salt of dodecyl benzene sulfonic acid, the sodium salt of isopropylnaphthalene sulfonic acid or a mixture of monomers, dimers, trimers and tetramers of the sodium salt of isopropylnaphthalene sulfonic acid; an alkali metal salt of an alkyl sulfuric acid, such as sodium decyl sulfate or sodium dodecyl sulfate; or an alkali metal salt of an alkyl sulfosuccinate, such as sodium bis (2-ethylthexyl) succinic sulfonate, diethyIpentyl sodium sulfosuccinate, dimethyIpentyl sodium sulfosuccinate.
  • an alkali metal salt of an alkarylene sulfonic acid such
  • milling media is used to prepare the dispersion
  • the mill is charged with the media such as, for example, spheres of silica, sand, zirconium oxide, zirconium silicate, alumina, titania, glass, etc.
  • the bead sizes typically range from 0.25 to 3.0 millimeters (mm) in diameter.
  • the scavenger particles in the dispersion should have mean diameters from 0.01 to 10.0 micrometers ( ⁇ m) and preferably from 0.05 to 5.0 micrometers ( ⁇ ) .
  • the use of solid particle dispersions in imaging is described, for example, in US Patent No. 4,006,025 to Swank et al and US Patent No.
  • the scavenger compounds can be used in the ways and for the purposes that scavengers for oxidized developing agent are employed in the art. They can be incorporated in a silver halide emulsion layer of the photographic element or in a separate. layer of the element. When incorporated in a separate layer, that layer is preferably an interlayer between silver halide emulsion layers although it can be an undercoat layer coated below all of the silver halide emulsion layers or an overcoat layer coated above all of the silver halide emulsion layers.
  • the two silver halide layers preferably comprise a coupler that' can react with oxidized developer such as a color developer to form or release a photographically useful group.
  • oxidized developer such as a color developer
  • photographically useful groups are known in the art and may be groups such as dyes, development modifiers such as development inhibitors, and the like.
  • the amount of scavenger compound employed will depend upon the particular purpose for which the scavenger is to be used and the degree of scavenging desired. Typically useful results are obtained when the scavenger is employed in an amount of between about 5 and 1000 mg/sq. meter per layer.
  • the vehicle for the crystalline solid particle dispersion can be essentially any photographic vehicle, such as gelatin and other hydrophilic colloids, or various synthetic polymers such as polyvinyl alcohol or acrylamide polymers.
  • Photographic vehicles commonly employed in silver halide photographic elements are described in Research Disclosure, December 1978, Item No. 17643, Section IX, the disclosure of which is incorporated herein by reference.
  • the photographic elements of the present invention can be simple black-and-white or monochrome elements comprising a support bearing a layer of the silver halide emulsion, or they can be multi-layer and/or multicolor elements. They can be designed for processing with separate solutions or for in-camera processing.
  • Multicolor elements contain dye image forming units sensitive to each of the three primary regions of the spectrum. Each unit can be comprised of a single emulsion layer or of multiple emulsion layers sensitive to a given region of the spectrum.
  • the layers of the element, including the layers of the image-forming units, can be arranged in any desired order.
  • the emulsion or emulsions can be disposed as one or more segmented layers, e.g., as by the use of microvessels or microcells, as described in U.S. Patent No. 4,362,806 to Whitmore.
  • a preferred photographic element according to this invention comprises a support bearing at least one blue-sensitive silver halide emulsion layer having associated therewith a yellow image dye-providing material, at least one green-sensitive silver halide emulsion layer having associated therewith a magenta image dye-providing material and at least one red- sensitive silver halide emulsion layer having associated therewith a cyan image dye-providing material, the element containing a scavenger of this invention.
  • the scavenger is in an interlayer between silver halide emulsion layers sensitive to the same or different silver halide emulsion layers.
  • the elements of the present invention can contain additional layers conventional in photographic elements, such as overcoat layers, spacer layers, filter layers, antihalation layers, pH lowering layers (sometimes referred to as acid layers and neutralizing layers), timing layers, opaque reflecting layer, opaque light-absorbing layers and the like.
  • the support can be any suitable support used with photographic elements. Typical supports include polymeric films, paper (including polymer-coated paper) , glass and the like. Details regarding supports and other layers of the photographic elements of this invention are contained in Research Disclosure. December 1978, Item 17643, referred to above.
  • the support can be coated with a magnetic recording layer as discussed in Research Disclosure 34390 of November 1992, the disclosure of which is incorporated herein by reference.
  • the light-sensitive silver halide emulsions employed in the photographic elements of this invention 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 bromo-iodide, silver chlorobromide, silver chloroiodide, silver chlorobromoiodide, and mixtures thereof.
  • the emulsions can be negative working or direct positive emulsions. They can form latent images predominantly on the surface of the silver halide grains or in the interior of the silver halide grains. They can be chemically and spectrally sensitized in accordance with usual practices.
  • the emulsions typically will be gelatin emulsions although other hydrophilic colloids can be used in accordance with usual practice. Details regarding the silver halide emulsions are contained in Research Disclosure, Item 17643, December 1978, and the references listed therein.
  • the photographic silver halide emulsions can contain other addenda conventional in the photographic art.
  • Useful addenda are described, for example, in Research Disclosure, December 1978, Item 17643.
  • Useful addenda include spectral sensitizing dyes and desensitizers, antifoggants, masking couplers, DIR couplers, DIR compounds, anti-stain agents, image dye stabilizers, absorbing materials, coating aids, plasticizers and lubricants, and the like.
  • the dye image-providing material employed in the photographic element it can be incorporated in the silver halide emulsion layer or in a separate layer associated with the emulsion layer.
  • the dye image-providing material can be any of a number known in the art, such as dye-forming couplers, bleachable dyes, dye developers and redox dye- releasers, and the particular one employed will depend on the nature of the element and the type of image desired.
  • Dye image-providing materials employed with conventional color materials designed for processing with separate solutions are preferably dye-forming couplers; i.e., compounds which couple with oxidized developing agent to form a dye.
  • Preferred couplers which form cyan dye images are phenols and naphthols.
  • Preferred couplers which form magenta dye images are pyrazolones and pyrazolotriazoles.
  • Preferred couplers which form yellow dye images are benzoylacetanilides and pivalylacetanilides.
  • Dye image-providing materials useful in diffusion transfer film units contain a dye moiety and a monitoring moiety.
  • the monitoring moiety in the presence of an alkaline processing solution and as a function of silver halide development, is responsible for a change in mobility of the dye moiety.
  • These dye image-providing materials can be initially mobile and rendered immobile as a function of .silver halide development, as described in U.S. Pat. No. 2,983,606. Alternatively, they can be initially immobile and rendered mobile, in the presence of an alkaline processing solution, as a function of silver halide development.
  • This latter class of materials include redox dye-releasing compounds.
  • the monitoring group is a carrier from which the dye is released as a direct function of silver halide development or as an inverse function of silver halide development.
  • Compounds which release dye as a direct function of silver halide development are referred to as negative-working release compounds, while compounds which release dye as an inverse function of silver halide development are referred to as positive-working release compounds.
  • the developing agents that can be used to develop the photographic elements of this invention, the oxidized form of which can be reduced by the scavengers of this invention, include hydroquinones, aminophenols, 3-pyrazolidones and phenylene diamines. Some of these developing agents, when used for certain applications, are referred to in the art as electron transfer agents.
  • the particular developing agent employed will depend on the particular type of photographic element to be processed. For example, phenylene diamines are the developers of choice for use with color photographic elements containing dye-forming couplers, while 3-pyrazolidones are preferably used with image transfer materials containing redox dye releasers.
  • Representative developing agents include: hydroquinone, N-methylaminophenol, l-phenyl-3- pyrazolidone, l-phenyl-4,4-dimethyl-3-pyrazolidone, 1- phenyl-4-methyl-4-hydroxymethyl-3-pyrazolidone, N,N- diethyl-p-phenylenediamine, 3-methyl-N,N-diethyl-p- phenylenedi mine, 3-methoxy-N,N-diethyl-p- phenylenediamine, N,N,N' ,N' -tetramethyl-p- phenylenediamine.
  • the dispersions used in the evaluation were prepared as follows:
  • a conventional oil-in-water dispersion of a photographically useful hydrazide oxidized developer scavenger, Compound 1 was prepared by dissolving 12.0 g of Compound 1 in 12.0 g of di-n-butylphthalate and 24.0 g of ethyl acetate at 60°C, then combining with an aqueous phase consisting of 16.0 g gelatin, 6.0 g of a 10% solution of a mixture of monomers, dimers, trimers and tetramers of the sodium salt of isopropylnaphthalene sulfonic acid, commercially available as Alkanol-XC from DuPont, and 130.0 g distilled water. The mixture was then passed through a colloid mill 5 times, followed by evaporation of ethyl acetate using a rotary evaporator and replacement with distilled water to yield a dispersion having 6.0% Compound 1 and 8.0% gelatin.
  • Dispersion B was prepared the same as Dispersion A except 3.0 g N, N-diethyl lauramide was substituted for 12.0 g di-n-butylphthalate, and 139.0 g distilled water was used.
  • a crystalline solid particle dispersion, Dispersion C, of Compound 1 was prepared by placing 2.4 g of Compound 1 in a 120 ml glass jar containing 18.0 g distilled water, 3.6 g of a 6.7% aqueous solution of octylphenoxy ethylene oxide sulfonate, commercially available as TX200 from Rohm and Haas, and 60 ml of 1.8 mm zirconium oxide beads. The jar was placed on a
  • SWECO vibratory mill for 5 days.
  • the milled slurry was mixed with gelatin and water to yield a dispersion containing 5% Compound 1 and 7% gelatin.
  • Dispersion D a conventional oil-in-water dispersion of Compound 1, was prepared the same as Dispersion A except 6.0 g di-n-butylphthalate and 136.0 g distilled water were used.
  • Preparation E a conventional oil-in-water dispersion of Compound 1, was prepared the same as Dispersion A except 6.0 g di-n-butylphthalate and 136.0 g distilled water were used.
  • Dispersion E was prepared the same as Dispersion D except tricresylphosphate was substituted for di-n-butylphthalate.
  • the oxidized developer scavenger dispersions were evaluated for particle growth as set forth below.
  • Compound 1 was dispersed as an oil-in-water dispersion as both Dispersion D and Dispersion E, and as a crystalline solid particle dispersion as Dispersion C. All dispersions were held for 24 hours at 45°C, and the particle size of each dispersion was measured by near infrared turbidimetry before and after the holding period. Table I gives the particle size in results, in microns, of the dispersions of Compound 1 before and after the holding period.
  • oxidized developer dispersions were evaluated as set forth below in color negative photographic materials prepared, exposed and processed according to conventional procedures .
  • Multilayer films were prepared, each comprising three color records separated by one or more interlayers, each of which contains a dispersion of oxidized developer scavenger.
  • the purpose of the interlayer is to prevent oxidized developer generated in one of the color layers from affecting any chemical reactions in another color layer.
  • the following compounds were used in preparing the multilayer film structures set forth below.
  • EXAMPLE 2 the oxidized developer scavenger Compound 1, dispersed as a crystalline solid particle dispersion, Dispersion C, is compared a conventional dispersion of Compound 1, Dispersion B.
  • multilayer films were prepared in which red- and green-sensitive layers were separated by an interlayer that contained the dispersions as described below. More specifically, the multilayer photographic film used as a COMPARISON in this example contained, inter alia, the following layers and materials:
  • a multilayer film of this invention INVENTION 2-2 was prepared in the same manner as the COMPARISON, except that in the interlayer, the conventional dispersion Dispersion B of Compound 1, is replaced with a crystalline solid particle dispersion Dispersion C of Compound 1 (0.0807 g/square meter) .
  • the photographic film elements were tested for the ability the interlayer formulation to prevent color contamination as follows:
  • each interlayer formulation may be determined by the following method.
  • the multilayer containing interlayers formulated with the control, comparison or invention dispersions is exposed to red or green light only.
  • the exposed color record is the only layer that develops and is designated the "causer" layer. Any other color records, which are not developing, are designated “receiver” layers.
  • the only way for color density to change in a receiver layer is for oxidized developer from the causer layer to diffuse through the interlayer to the receiver layer. Differences in the density in a receiver layer indicate differences in the effectiveness of the scavenger in reacting with oxidized developer and preventing color contaminatio .

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  • Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)

Abstract

Un accroissement indésirable de particules comprenant un révélateur oxydé par l'hydrazide dans une dispersion photographique peut être fortement réduit lorsque le piégeur d'hydrazide se présente sous la forme d'une dispersion de particules solides cristallines dispersées dans un milieu aqueux. On prépare la dispersion en agitant les particules solides cristallines du piégeur dans un milieu aqueux en présence d'un agent de dispersion et en l'absence substantielle d'un solvant organique.
EP94922427A 1994-05-16 1994-05-16 Element photographique possedant une dispersion particulaire solide d'un piegeur de revelateur oxyde Ceased EP0708933A1 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US1994/005446 WO1995031752A1 (fr) 1994-05-16 1994-05-16 Element photographique possedant une dispersion particulaire solide d'un piegeur de revelateur oxyde

Publications (1)

Publication Number Publication Date
EP0708933A1 true EP0708933A1 (fr) 1996-05-01

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Family Applications (1)

Application Number Title Priority Date Filing Date
EP94922427A Ceased EP0708933A1 (fr) 1994-05-16 1994-05-16 Element photographique possedant une dispersion particulaire solide d'un piegeur de revelateur oxyde

Country Status (3)

Country Link
EP (1) EP0708933A1 (fr)
JP (1) JPH09500983A (fr)
WO (1) WO1995031752A1 (fr)

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1157501A (en) * 1965-09-10 1969-07-09 Ilford Ltd Photographic Colour Transfer Process.
FR2344050A1 (fr) * 1976-03-09 1977-10-07 Agfa Gevaert Ag Technique d'introduction d'additifs photographiques dans des emulsions d'un sel d'argent
DE68929026T2 (de) * 1988-04-21 2000-01-27 Eastman Kodak Co. (A New Jersey Corp.), Rochester Photographisches Element, das einen Fänger für das Entwickleroxidationsprodukt enthält
US5300394A (en) * 1992-12-16 1994-04-05 Eastman Kodak Company Dispersions for imaging systems

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9531752A1 *

Also Published As

Publication number Publication date
WO1995031752A1 (fr) 1995-11-23
JPH09500983A (ja) 1997-01-28

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