EP0724191A1 - Mikroausgefällte Farbdispersionen enthaltende photographische Materialien geeignet für Anwendungen mit schneller Verarbeitung - Google Patents

Mikroausgefällte Farbdispersionen enthaltende photographische Materialien geeignet für Anwendungen mit schneller Verarbeitung Download PDF

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Publication number
EP0724191A1
EP0724191A1 EP95203367A EP95203367A EP0724191A1 EP 0724191 A1 EP0724191 A1 EP 0724191A1 EP 95203367 A EP95203367 A EP 95203367A EP 95203367 A EP95203367 A EP 95203367A EP 0724191 A1 EP0724191 A1 EP 0724191A1
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EP
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Prior art keywords
dye
substituted
photographic material
dyes
merostyryl
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EP95203367A
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English (en)
French (fr)
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EP0724191B1 (de
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Robert c/o Agfa-Gevaert N.V. DIE 3800 Lemahieu
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Agfa Gevaert NV
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Agfa Gevaert NV
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    • 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
    • G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
    • G03C1/825—Photosensitive materials characterised by the base or auxiliary layers characterised by antireflection means or visible-light filtering means, e.g. antihalation
    • G03C1/83—Organic dyestuffs therefor
    • G03C1/832—Methine or polymethine dyes
    • 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

  • the present invention relates to dispersions of filter dyes and their use as antihalation and anti-cross-over dyes in photographic elements.
  • Dispersions of non-spectrally sensitizing dyes are widely used in photographic elements, particularly in photographic elements of the silver halide type. They may be used in a photosensitive silver halide emulsion layer as screening dye dispersions, in an undercoat layer adjacent to the photosensitive layer and/or in a backing layer on the side of the support opposite to the photosensitive layer(s) in order to absorb reflected and scattered light thereby serving as antihalation dye dispersions. In an overcoat or interlayer the said dispersions may be used to shield a particular photosensitive layer against undesired exposure being therefore referred to as filter or absorber dye, thereby adjusting the sensitivity of a photographic element as required in the production specifications.
  • an absorber dye dispersion can be present in one or more filter layers between silver halide emulsion layers that are coated at opposite sides of a transparent film support of an X-ray recording material.
  • the imagewise exposure of said recording material proceeds in a cassette between a pair of X-ray intensifying screens that each are held in contact with an adjacent silver halide emulsion layer.
  • the absorption spectrum of the dye dispersion should approximately be equal to the sensitivity spectrum of the corresponding silver halide emulsion in the layer of which a sharp image has to be reproduced.
  • filter dyes present in dispersed form remain, i.e., that they are non-migratory, in the layer wherein they have been incorporated especially when this layer is in direct contact with the silver halide emulsion layer in order to prevent a desensitizing action on the silver halide.
  • the filter dyes present in dispersed form may not stain the photographic material after image processing. Therefore preference is given to filter dyes that decolorize or can be removed from the photographic element in the processing stage. This requirement is nowadays becoming more and more stringent as rapid processing times are of increasing interest.
  • filter dyes characterized by the presence of a 2-pyrazoline-5-one nucleus substituted with a carboxyphenyl group and including a methine group or chain linked to a dialkylamino group are described in US-P 4,857,446.
  • the decolorization of said filter dyes proceeds very rapidly in alkaline aqueous processing baths.
  • the monomethine dyes have an absorption spectrum of which the maximum is in the shorter wavelength range of the visible spectrum so that normally a second filter dye is needed to block or absorb green light and even a third one to absorb radiations of longer wavelengths, e.g., radiations in the red or even in the infrared region.
  • the problem is how to get the filter dye in a coated layer so that all the requirements mentioned previously are met.
  • Normally storage dispersions of said solid particle dispersions are formed in aqueous gelatinous medium by means of ball milling, sand milling, roller milling and other techniques. Said techniques are not very economically interesting as milling times from 6 to 24 hours are not exceptionnal.
  • the mechanical load therein is very hard as temperature increases may lead to a partial destruction of the dyes.
  • milling techniques are leading to the blocking of the mechanical process as the viscosity is increasing dramatically.
  • the long preparation time makes a preparation " directly ready-for-incorporation in coating solutions" impossible.
  • the dispersions have to be stored and desintegration of the dispersing colloid and/or agglomeration of the dye particles may occur.
  • Microprecipitation techniques have, e.g., been described in DE-PS 932 343 wherein the statement is made that "alkaline soluble dyes can be precipitated in acid medium, e.g., in the presence of gelatin” and in EP-Specification 15 601, wherein it has been disclosed that "it is possible to use the dyes in their salt form and to convert them in situ into their acid form”.
  • JP-A 61185568 in EP-S 19 299, EP-A's 323 729; 549 486 and 549 489; in GB 1,210,253 and 1,305,441 and in US-P's 4,970,139; 5,075,205; 5,077,184; 5,089,380; 5,104,776; 5,155,015 and in 5,182,189.
  • Precipitation of mixtures of dyes in an alkaline gelatinous solution of alkaline soluble dyes by acidifying said solution, in order to get them in dispersed form, covering an extended wavelength region, can however lead to an increase of the viscosity of the solution. This depends not only on the degree of viscosity of the gelatin used, but also on the choice of the dye mixture (amount of dyes and ratio by weight of the dyes), the particle size (further determining the dissolution rate) and of the chemical composition of the dyes.
  • a still further object of this invention is to eliminate the need to provide storage dispersions and to prepare these dispersions "in situ" at the time the coating solution is prepared.
  • a photographic material comprising a support and on at least side thereof at least one light-sensitive silver halide emulsion layer characterised in that said material comprises at least one hydrophilic colloid layer, comprising a dispersion of at least two dyes: at least one dye being a merostyryl dye and the at least one other dye being an oxonol dye, wherein both dyes are soluble at a pH value above 8.0 and insoluble at a pH value below 6.0, and wherein at least said oxonol dye is in the form of a microprecipitated dispersion.
  • a method of preparing the dispersion of at least two dyes according to this invention is also disclosed, wherein at least said at least one oxonol dye is microprecipitated by acidifying an aqueous alkaline solution.
  • a method of processing the photographic material comprising the steps of developing, fixing, rinsing and drying, within a total processing cycle of less than 60 seconds.
  • dispersions of at least two dyes has to be interpreted as being different from a mixture of two classical dispersions obtained by mechanical techniques such as, e.g., ball milling said dyes apart or together in the presence of gelatin.
  • the dispersion of at least two dyes present in a silver halide material according to this invention that at least one oxonol dye is present in the form of a microprecipitated dispersion.
  • Said microprecipitated dispersion is obtained by the method of acidifying an aqueous alkaline solution.
  • the presence of the at least one merostyryl dye in microprecipitated form may occur in the said dispersion mixture.
  • Dye dispersions of at least two dyes to be incorporated in the silver halide photographic material according to this invention are those wherein at least one merostyryl dye corresponding to the formula (I), and at least one microprecipitated oxonol dye corresponding to the formula (II), are present.
  • Preferred merostyryl dyes present in at least one hydrophilic layer of a photographic material according to this invention are represented by the general formula (I) wherein n represents 0 or 1; each of p and q independently represents 0, 1 or 2; Q represents the atoms necessary to form an acidic nucleus; each of R 1 and R 2 independently represents hydrogen, substituted or unsubstituted alkyl, substituted or unsubstituted aryl, COOR 3 , NHCOR 4 or NHSO 2 R 5 with R 3 representing hydrogen or substituted or unsubstituted alkyl, each of R 4 and R 5 independently representing substituted or unsubstituted alkyl, or substituted or unsubstituted aryl, X represents OR 6 , SR 6 or NR 7 R 8 , wherein R 6 represents H, substituted or unsubstituted alkyl, substituted or unsubstituted aryl and each of R 7 and R 8 which may be the same or different represents hydrogen, substituted or
  • said ionizable group is situated at R 2 .
  • the acidic nucleus is preferably a pyrazolone, barbituric acid, thiobarbituric acid, rhodanine, hydantoine, oxazolidindione, thio-oxazolidindione or an isoxazolinone.
  • the necessary atoms represented by L 1 -L 3 are mono- or trimethine.
  • Said oxonol dye(s) has (have) been described, e.g., in US-P's 4,092,168 and 4,288,534.
  • the dispersion of at least two dyes is incorporated in at least one hydrophilic colloid layer of a silver halide photographic material wherein the absorption spectrum is in the region from 370 to 700 nm and wherein the amount per sq.m. of the merostyryl dye(s) corresponding to the formula (I) is from 0.1 to 0.3 g, whereas the amount per sq.m. of the oxonol dye(s) is about 0.1 g, i.a. from 0.09 to 0.11 g.
  • the ratio by weight, of the said at least one merostyryl dye corresponding to the formula (I) and the said at least one oxonol dye corresponding to the formula (II) is from 3:1 to 1:1 in the said at least one hydrophilic colloid layer of the silver halide photographic material according to this invention.
  • Preparation methods of the dye dispersion of the said at least two dyes are leading to particle sizes of the dispersion which are smaller than 500 nm.
  • Particle sizes smaller than 500 nm require an acidifying step of alkaline solutions (coating solutions or separate solutions containing at least one dye) in well-defined pH-conditions.
  • a pH-stat apparatus can be used to controll these conditions, but the rate at which the acidic solutions are added is important too. Both conditions are not only determining the ultimate particle size of the dispersed dye particles, but are also determining the absorption densities over the whole wavelenght region from 370 to 700 nm that can be obtained.
  • Preferred absorption densities in said wavelength region are at least 0.3, and, more preferably, at least 0.6. It is evident that more finely dispersed dye particles require a lower coating amount of the said dyes in order to reach the preferred absorption densities. Moreover in the alkaline developer it is evident that finer alkali soluble dye particles are decolourised more quickly and can be more easily removed from the silver halide photographic material in the further processing steps. It is clear that this is in favour of rapid processing applications of the photographic material according to this invention.
  • a preferred acidic solution to acidify alkaline dye solutions and/or coating solutions is citric acid, although other acids can also be used.
  • microprecipition of an alkaline dye solution proceeds in the presence of a protective colloid.
  • Preferred protective colloids are gelatin and/or silica sol. Further specific embodiments if silica sol is used as a protective colloid have been described in EP-A 569 074, which is incorporated herein by reference. In the thus obtained dye dispersions the ratio by weight of gelatin or silica to the dyes is preferably from 1:5 to 5:1.
  • One method of incorporating dyes in at least one hydrophilic colloid layer of a photographic material according to this invention consists in that at least one oxonol dye according to the general formula (II) is microprecipitated by the step of acidifying an alkaline solution in which said at least one dye is soluble.
  • Said alkaline solution can be a separately prepared solution that is added to the coating solution afterwards.
  • After addition of (a) merostyryl dye(s) according to the general formula (I) to the said coating solution coating is performed on at least one side of a support to form at least one hydrophilic colloid layer of said photographic material.
  • At least one oxonol dye according to the general formula (II) is microprecipitated by acidifying the coating solution which already contains a merostyryl dye according to the general formula (I) in dispersed form.
  • Said coating solution can be acidic or alkaline beforehand.
  • the at least one merostyryl dye according to the general formula (I) can be present as a microprecipitated dispersion (when the coating solution is acidic) or as a solubilized dye (when said coating solution is alkaline).
  • Another method of incorporating dyes in at least one hydrophilic colloid layer of a photographic material according to this invention consists in that said at least one oxonol dye according to the general formula (II) is microprecipitated before addition to the acidic coating solution which contains the merostyryl dye according to the general formula (I) in dispersed form and wherein said microprecipitated oxonol dye is added thereto.
  • the coating solution is already acidic. Further coating of the said coating solution follows on at least one side of a support to form at least one hydrophilic colloid layer.
  • an alkaline solution of the at least one oxonol dye according to the general formula (II) is added to the acidic coating solution, which contains the merostyryl dye according to the general formula (I) in dispersed form.
  • said merostyryl dye(s) according to the formula (I), present in dispersed form has (have) been prepared by the step of microprecipitation, characterised in that an aqueous alkaline solution of the said dye(s) is (are) acidified
  • This preparation step can occur in the coating solution before addition of the oxonol dye(s) or in a separate precipation vessel.
  • incorporating dyes in at least one hydrophilic colloid layer of a photographic material according to this invention is performed in such a way that at least one merostyryl dye according to the general formula (I) and at least one oxonol dye according to the general formula (II) are microprecipitated apart or together before or after addition to the coating solution by acidifying the said at least one aqueous alkaline dye or alkaline coating solution.
  • This addition to the coating solution may proceed consecutively or simultaneously.
  • Said coating solution may still be alkaline, whereafter an acidifying step can be applied afterwards.
  • the coating solution can be acidified just before coating on a support.
  • an acidic solution can be added to the coating solution or an acidic coating solution can be coated simultaneously together with the said coating solution.
  • Said coating solution can be alkaline or slightly acidic before coating.
  • dispersions of dyes according to this invention in the light-sensitive silver halide layer(s) is not excluded, it is preferred to incorporate them into hydrophilic non light-sensitive layers as there are one or more backing layers in the case of single side coated materials, antihalation undercoat layers, interlayers, protective layers and/or outermost layers.
  • an X-ray photographic material or a material for micrography contains one or more layers wherein dye dispersions as described hereinbefore are incorporated, although other materials are not excluded either.
  • multilayer materials such as, e.g., colour materials, may contain at least one filter layer, interlayer and/or antihalation layer wherein dye dispersions prepared according to the method of this invention are present.
  • Interlayers in the layer arrangement of such multilayer materials may contain very fine light-insensitive silver halide particles with a diameter of 10 to 100 nm known as Lippmann emulsions, incorporated into said layers, e.g., to serve as scavangers to prevent oxidized developer products to migrate into adjacent layers.
  • the dye dispersions prepared by the method according to this invention may be used to adjust the sensitivity of the photographic material as required by the production specifications. So it is possible to apply a dosing feeder just before coating the hydrophilic layer concerned and to control the production of the photographic material in this way.
  • the dye dispersions according to this invention absorbing in the blue, green and red spectral range can be used advantageously between silver halide emulsion layers of double-sided emulsion coated (duplitized) photographic film material as applied in X-ray recording for use with visible light emitting X-ray conversion phosphor screens.
  • the light that would cross the support and to some extent become scattered thereby, is considerably attenuated and cannot give rise to an unsharp image into an opposite silver halide emulsion layer.
  • the dye dispersions are incorporated into non-light sensitive hydrophilic colloid layers a radiographic material that is provided at both sides of the support with a silver halide emulsion layer and an antistress layer as a protective layer coated thereover.
  • the radiographic material preferably has on both sides of the film support silver halide emulsion coatings that are split into two distinctive emulsion layers having silver halide crystals of different average grain size one of which is a high speed emulsion layer and the other is a low speed emulsion layer; the high speed emulsion layer being situated at a larger distance from the support than the low speed emulsion layer.
  • the layer arrangement may also be opposite to the previously cited sequence in order to get a higher contrast. Moreover even without using a separate anticrossover layer this layer arrangement reduces crossover, especially in the critical low density area.
  • the crossover reduction is improved without leaving a colour stain upon processing, especially upon rapid processing in less than 60 seconds, preferably in 45, 38 or 30 seconds as reference processing times of materials with high-throughput.
  • said dispersions absorbing blue, green and red light can be used in an antihalation layer of a photographic silver halide photographic material according to this invention in order to improve image sharpness by absorbing exposure light penetrating the emulsion layer(s) into the direction of the support.
  • the use of said light absorbing dye dispersions in an antihalation layer is particularly advantageous in silver halide photographic emulsion materials that are made spectrally sensitive to blue, green or red light and of which the exposure proceeds with a suitable light source.
  • a method of processing is disclosed of a photographic material according to this invention built up with hydrophilic layers containing dye dispersions according to this invention, said method comprising the steps of developing, fixing, rinsing and drying, within a total processing cycle of less than 60 seconds.
  • a processing time of less than 45 seconds and even less than 30 seconds can be obtained.
  • the dyes dispersed as disclosed herein are easily solubilized and are indeed removed almost completely from a hydrophilic waterpermeable colloid layer of a photographic silver halide emulsion material by its common alkaline aqueous liquid processing without leaving any residual stain.
  • the presence of sulfite in the processing solution contributes to a more rapid discoloration of the filter dyes.
  • a more convenient method of dispersion is followed by preparing the dispersion "in situ" in a coating solution.
  • the dyes were dissolved in water and alkali as described hereinafter and were added to a gelatin solution at 40°C.
  • the pH value was adjusted with an aqueous acidic solution to a value of about 5.0 in order to obtain a particle size of less than 500 nm.
  • a dispersion was obtained by dissolving dye-(IIIa) and dye-(IVb) in an aqueous alkaline solution.
  • the solutions were added to an aqueous solution of 20 % of gelatin and dispersed by neutralisation with an aqueous acidic solution to a solution pH of about 5.0.
  • a 2 %, respectively 1 % dispersion of the respective dye-(IIIa) and dye-(IVb) in 3.3 % of gelatin was obtained, the particle size of which was less than 500 nm.
  • Dye dispersions prepared by acidifying the alkaline solutions of said dyes are called “in situ dispersions” (further indicated by ISD), opposite to the classic “gelatinous milling dispersions” (further indicated as GMD).
  • Coating solutions were made for antihalation layers. Besides the dyes or dye dispersions added thereto, a latex compound, surfactants, a biocid (phenol) and a hardening agent (formaldehyde) were present in the aqueous gelatinous solution.
  • the viscosity of the coating solution of Example 1, as in Fig. 2, was measured at a coating pH of 5.3 and at a coating temperature of 36°C by means of a viscosimeter and expressed in mPas for each measurement.
  • in situ prepared dispersions of merostyryl dyes and oxonol dyes are offering the possibility to make “in situ” prepared dispersions, opposite to the little handsome "storage dispersions”. Moreover the viscosity of the coating solution is not increased, even not if higher amounts of dyes are precipitated and/or if said coating solution is stored for several hours before coating.
  • a weight ratio between dye IIIa and dye IVb of about 2 or more offers the lowest increase of the viscosity at a coating pH value of 4.5. It is clear that lower amounts of gelatin are leading to a lower increase in viscosity if the coating pH is lowered.

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EP19950203367 1994-12-27 1995-12-06 Mikroausgefällte Farbdispersionen enthaltende photographische Materialien geeignet für Anwendungen mit schneller Verarbeitung Expired - Lifetime EP0724191B1 (de)

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EP19950203367 EP0724191B1 (de) 1994-12-27 1995-12-06 Mikroausgefällte Farbdispersionen enthaltende photographische Materialien geeignet für Anwendungen mit schneller Verarbeitung

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EP94203766 1994-12-27
EP94203766 1994-12-27
EP19950203367 EP0724191B1 (de) 1994-12-27 1995-12-06 Mikroausgefällte Farbdispersionen enthaltende photographische Materialien geeignet für Anwendungen mit schneller Verarbeitung

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EP0724191B1 EP0724191B1 (de) 2003-08-27

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6045986A (en) * 1997-05-20 2000-04-04 Tulalip Consultoria Commerial Sociedade Unipessoal S.A. Formation and photographic use of solid particle dye dispersions
EP1246003A1 (de) * 2001-03-29 2002-10-02 Agfa-Gevaert Verfahren zur Herstellung von zusammen ausgefällten mikrokristallinen Farbstoffdispersionen und Materialien, die Schichten mit diesen Dispersionen aufweisen
US6641621B2 (en) 2001-03-29 2003-11-04 Agfa-Gevaert Method of preparing co-precipitated microcrystalline dye dispersions and layers coated therewith in materials
EP1246004A3 (de) * 2001-03-29 2006-07-26 Agfa-Gevaert Verfahren zur Herstellung von zusammen ausgefällten mikrokristallinen Farbstoffdispersionen und Materialien, die Schichten mit diesen Dispersionen aufweisen

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0549489A1 (de) * 1991-12-20 1993-06-30 Eastman Kodak Company Mikrofällungsverfahren zur Dispergierung photographischer Filterfarbstoffe
EP0554834A2 (de) * 1992-02-03 1993-08-11 Fuji Photo Film Co., Ltd. Verfahren zur Dispergierung eines Farbstoffs und ein Farbstoff enthaltendes photographisches Silberhalogenidmaterial
EP0587229A2 (de) * 1992-09-11 1994-03-16 Agfa-Gevaert N.V. Filterfarbstoffe für Schnellverarbeitungs-Verwendungen

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0549489A1 (de) * 1991-12-20 1993-06-30 Eastman Kodak Company Mikrofällungsverfahren zur Dispergierung photographischer Filterfarbstoffe
EP0554834A2 (de) * 1992-02-03 1993-08-11 Fuji Photo Film Co., Ltd. Verfahren zur Dispergierung eines Farbstoffs und ein Farbstoff enthaltendes photographisches Silberhalogenidmaterial
EP0587229A2 (de) * 1992-09-11 1994-03-16 Agfa-Gevaert N.V. Filterfarbstoffe für Schnellverarbeitungs-Verwendungen

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6045986A (en) * 1997-05-20 2000-04-04 Tulalip Consultoria Commerial Sociedade Unipessoal S.A. Formation and photographic use of solid particle dye dispersions
EP1246003A1 (de) * 2001-03-29 2002-10-02 Agfa-Gevaert Verfahren zur Herstellung von zusammen ausgefällten mikrokristallinen Farbstoffdispersionen und Materialien, die Schichten mit diesen Dispersionen aufweisen
US6641621B2 (en) 2001-03-29 2003-11-04 Agfa-Gevaert Method of preparing co-precipitated microcrystalline dye dispersions and layers coated therewith in materials
US7026108B2 (en) 2001-03-29 2006-04-11 Agfa-Gevaert Method of preparing co-precipitated microcrystalline dye dispersions and layers coated therewith in materials
EP1246004A3 (de) * 2001-03-29 2006-07-26 Agfa-Gevaert Verfahren zur Herstellung von zusammen ausgefällten mikrokristallinen Farbstoffdispersionen und Materialien, die Schichten mit diesen Dispersionen aufweisen

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