EP0738918A1 - Photographisches negativ-arbeitendes Farbfilmelement - Google Patents

Photographisches negativ-arbeitendes Farbfilmelement Download PDF

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Publication number
EP0738918A1
EP0738918A1 EP95201015A EP95201015A EP0738918A1 EP 0738918 A1 EP0738918 A1 EP 0738918A1 EP 95201015 A EP95201015 A EP 95201015A EP 95201015 A EP95201015 A EP 95201015A EP 0738918 A1 EP0738918 A1 EP 0738918A1
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EP
European Patent Office
Prior art keywords
dye
substituted
layer
film element
element according
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Granted
Application number
EP95201015A
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English (en)
French (fr)
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EP0738918B1 (de
Inventor
Geert Vercruysse
Marc Ailliet
Redgy De Groote
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Agfa Gevaert NV
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Agfa Gevaert NV
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Priority to DE1995618402 priority Critical patent/DE69518402T2/de
Priority to EP19950201015 priority patent/EP0738918B1/de
Publication of EP0738918A1 publication Critical patent/EP0738918A1/de
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Publication of EP0738918B1 publication Critical patent/EP0738918B1/de
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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
    • 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
    • G03C7/3029—Materials characterised by a specific arrangement of layers, e.g. unit layers, or layers having a specific function

Definitions

  • the present invention relates to a photographic colour negative film element with an improved colour hue.
  • Colour negative films are light-sensitive recording film elements having a flexible transparent support and light-sensitive layers composed in such a way that by normal exposure to light in a camera and subsequent chemical processing a negative colour image is obtained.
  • Colour intermediate films are negative working light-sensitive recording elements also having a flexible transparent support and light-sensitive layers composed in such a way that by exposure to light through an original colour negative and subsequent chemical processing a duplicate positive of said original colour negative is obtained and that by exposure to light of another colour intermediate film through said duplicate positive and subsequent chemical processing a duplicate of said original colour negative is obtained.
  • Both types of colour films basically consist of a transparent film support carrying in the given order at least one red-sensitized silver halide emulsion layer, at least one green-sensitized silver halide emulsion layer, at least one blue-sensitive silver halide emulsion layer, and a gelatin antistress layer.
  • a transparent film support carrying in the given order at least one red-sensitized silver halide emulsion layer, at least one green-sensitized silver halide emulsion layer, at least one blue-sensitive silver halide emulsion layer, and a gelatin antistress layer.
  • intermediate layers of a hydrophilic colloid, mostly gelatin are provided for better colour separation.
  • the intermediate layer beneath the blue-sensitive layer(s) currently is a yellow filter layer that absorbs the blue light not absorbed by the blue-sensitive layer(s) and transmits the red and green light to which the lower layers are sensitive.
  • a gelatin intermediate layer is often used, which helps
  • One method to improve the colour rendition of colour negative or a colour intermediate film consists in changing the absorption spectrum of the spectrally sensitized silver halide crystals, in order to absorb exposure light in three well-defined spectral regions, being the blue-light, the green-light and the red-light absorbing regions respectively. A minimum overlap of the said regions is highly requested therefor.
  • spectral sensitizers or combinations thereof offering an adapted absorption in favour of true colour rendition which are less non-migratory, the problem arises that side-absorptions are leading to colour contaminations.
  • a photographic negative-working colour film element comprising on a transparent film support, at least one red-sensitized silver halide emulsion layer comprising at least one cyan-forming coupler, an intermediate layer, at least one green-sensitized silver halide emulsion layer comprising at least one magenta-forming coupler, at least one blue-sensitive silver halide emulsion layer comprising at least one yellow-forming coupler, and a yellow filter layer, situated between the green-sensitive layer(s) and the blue-sensitive layer(s), characterised in that the said yellow filter layer comprises a synthetic clay.
  • At least one synthetic clay is added to the yellow filter layer of the negative-working colour film element.
  • Synthetic clays are clearly differing from natural clays in that the layered structure and composition are well-known and predetermined, and that the addition of specific additives can introduce (new) desired properties.
  • Natural clays are essentially hydrous aluminum silicates, wherein alkali metals or alkaline-earth metals are present as principal constituents. Also in some clay minerals magnesium or iron or both replace the aluminum wholly or in part. The ultimate chemical constituents of the clay minerals vary not only in amounts, but also in the way in which they are combined or are present in various clay minerals. It is also possible to prepare synthetic clays, so that more degrees of freedom can lead to reproducible tailor made clay products for use in different applications.
  • smectite clays are well-known. For the said smectite clays some substitutions in both octahedral and tetrahedral layers of the crystal lattice occur, resulting in a small number of interlayer cations. Smectite clays form a group of "swelling" clays which take up water and organic liquids between the composite layers and which have marked cation exchange capacities.
  • Synthetic chemically pure clays have been produced having an analogous structure as smectite clay and are now available. So the preferred synthetic smectite clay additive for the purposes of this invention is LAPONITE JS, trade mark products of LAPORTE INDUSTRIES Limited, London. Organophilic clays and process for the production thereof have been described in EP-Patent 161 411 B1.
  • LAPONITE JS is described as a synthetic layered hydrous sodium lithium magnesium fluoro-silicate incorporating an inorganic polyphoshate peptiser.
  • the said fluoro-silicate appears as free flowing white powder and hydrates well in water to give virtually clear and colourless colloidal dispersions of low viscosity, also called "sols".
  • On addition of small quantities of electrolyte highly thixotropic gels are formed rapidly.
  • the said thixotropic gels can impart structure to agueous systems without significantly changing viscosity. An improvement of gel strength, emulsion stability and suspending power can be observed by making use of it in the said agueous systems.
  • LAPONITE RDS is described as a synthetic layered hydrous sodium lithium magnesium silicate with analogous properties as LAPONITE JS.
  • Laponite clay as a synthetic inorganic gelling agent for agueous solutions of polar organic compounds has been presented at the Symposium on "Gums and Thickeners", organised by the Society of Cosmetic Chemists of Great Britain, held at Oxford, on 14th October 1969.
  • Laporte Inorganics Laponite Technical Bulletin L104/90/A a complete review about the structure, the chemistry and the relationship to natural clays is presented. Further in Laporte Inorganics Laponite Technical Bulletin L106/90/c properties, preparation of dispersions, applications and the product range are disclosed.
  • a detailed description of "Laponite synthetic swelling clay, its chemistry, properties and application” is given by B.J.R. Mayes from Laporte Industries Limited.
  • the primary particles are platelets having a diameter of about 0.025 ⁇ m and a thickness of about 0.001 ⁇ m.
  • a yellow filter layer situated under the light-sensitive layers which are sensitive to incident blue light.
  • the main compound therein is the yellow dye, having the desired absorption spectrum in order to act as a suitable filter for blue light.
  • colloidal silver can be used, as, depending on the particle size and the particle size distribution the required region of the wavelength spectrum can be covered.
  • the said silver particles can easily be removed in the bleaching step of the processing cycle.
  • Another important compound in the yellow filter layer is the colourless coupler which prevents the wandering of oxidised developer from the green-sensitised layer to the blue-sensitive layer and vice versa in order to prevent colour contamination.
  • addition of the said synthetic clay or a mixture of synthetic clays is not restricted to the filter layer, but addition to at least one other hydrophilic layer is recommended. So, e.g., addition to the interlayer coated between the support and the red-sensitized silver halide emulsion layer, coated closest to the support, and/or, even more preferred, to the interlayer between the red-sensitized and the green-sensitized silver halide emulsion layers is highly recommended.
  • the photographic negative-working film element is built up as has been described in EP-A 582 000.
  • the said non-light-sensitive layers disclosed therein, which, according to this invention optionally comprise at least one synthetic clay, are a blue antihalation layer, coated between the support and the red-sensitized silver halide emulsion layer, coated closest to the support, wherein said blue antihalation layer comprises at least one blue non-diffusing dye in a hydrophilic colloid, said dye absorbing red light.
  • the yellow filter layer in the layer arrangement as described in EP-A 0 582 000 the yellow filter layer, according to this invention, always comprises at least one synthetic clay and at least one yellow non-diffusing dye in a hydrophilic colloid, said dye absorbing blue light and wherein the said dye(s) is (are) removable and/or decolourizable in a processing baths.
  • the said yellow non-diffusing dye is represented by the general formula (I) wherein
  • a particularly preferred yellow non-diffusing dye is 1-(p-carboxyphenyl)-3-methyl-4-(p-hydroxybenzylidene)-2-pyrazolin-5-one.
  • the said yellow non-diffusing dye is represented by the general formula (II) wherein
  • a dye represented by the general formula (III) is present in another embodiment in the said blue antihalation layer of the photographic material according to this invention, wherein said layer optionally comprises at least one synthetic clay.
  • a dye represented by the general formula (III) each of R 5 and R 6 , which may be the same or different, represents hydrogen, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group, and each of R 3 and R 4 , which may be the same or different, represents one of the groups represented by R 1 and R 2 , or a cycloalkyl group.
  • a particularly preferred blue non-diffusing dye in the material according to this invention is the pentamethine oxonol-type barbituric acid derivative dye being the ammonium salt of (1,5-bis-[1-H-3-(p-methoxyphenyl)-barbituric acid]-pentamethine oxonol).
  • said interlayer optionally containing at least one synthetic clay, is a green-light absorbing non-diffusing dye.
  • said dye working as a antihalation dye is a merostyryl dye having the general formula (I) wherein n equals 1.
  • said green-light absorbing dye is an oxonol dye having the general formula (II), wherein m equals 1.
  • Particularly preferred in the photographic element according to this invention is the presence, in solid dispersed or microprecipitated state of the said yellow non-diffusing merostyryl dye and/or the said green-light absorbing non-diffusing antihalation dye and/or the blue non-diffusing dye.
  • the thickness of the yellow filter layer is not critical, though generally a thickness of 0.5 to 3 ⁇ m is used.
  • the thickness and the amount of the dyes present therein are preferably chosen in such a way that the resulting antihalation layer has an optical density of about 0.5 to about 1.5 as measured in its own absorption range.
  • the amount of the yellow dye in the yellow filter layer may vary from 10 mg to 750 mg per m2 and more preferably from 25 to 250 mg per m2. It is clear that the thinner the coated layers, the smaller the light scattering and the sharper the images.
  • Thin coated layers are often related with the possibility to coat less silver emulsion crystals per surface unit, but this is only possible if an optimised relation between crystal size and speed has been reached, eventually with the aid of development accelerators and, especially in colour negative materials, with the aid of suitable development inhibiting releasing couplers, also called DIR-couplers.
  • Particularly preferred herein is the colourless DIR-coupler corresponding to the formula (V) hereinafter, which can be used in at least one of the hydrophilic layers of the material according to this invention.
  • the said DIR-coupler is well-known from DE 3,644,416 and from US-P's 4,049,458; 4,870,000 and 5,021,332.
  • the synthetic clay present in the yellow filter layer and, optionally, in at least another non-light-sensitive hydrophilic layer, in particular the interlayer between the red and green sensitive layers and/or the layer between the support and the red-sensitive layers is a synthetic smectite clay.
  • Preferred clays present in the yellow filter layer are synthetic layered hydrous sodium lithium magnesium silicates and synthetic layered hydrous sodium lithium magnesium fluoro-silicates and more preferably LAPONITE RDS and LAPONITE JS, both trademark names of LAPORTE INDUSTRIES Limited, London.
  • Preferred synthetic clays optionally present in the other hydrophilic non-light-sensitive layers adjacent to the green-sensitised and/or red-sensitised layer(s) are synthetic layered hydrous sodium lithium magnesium fluoro-silicates and more preferably the already mentioned LAPONITE JS.
  • the said synthetic clay(s) is (are) present in an amount of at least 10% by weight versus the amount of hydrophilic colloid present in the yellow filter layer and, optionally, in at least another hydrophilic non-light-sensitive layer.
  • Preferred amounts of synthetic clay added to at least one of the hydrophilic layer(s), and to the yellow filter layer in particular, are from 10 to 250 mg/m 2 , preferably from 20 to 200 mg/m 2 and more preferably from 25 to 150 mg/m 2 .
  • At least one of the hydrophilic non-light-sensitive layers according to this invention comprise at least one development accelerator in order to enhance the sensitivity of the adjacent light-sensitive layers.
  • Especially preferred layers are the protective antistress layer, coated adjacent to the most sensitive blue-light sensitive silver halide emulsion layer and the interlayer between the red- and green-sensitised emulsion layers, adjacent to the most sensitive red-sensitised emulsion layer.
  • a particularly preferred development accelerator used in at least one of the said hydrophilic non-light-sensitive layers, inclusive the yellow filter layer is the compound having the general formula (VI) R[O-CH 2 -CH 2 -S-(LINK 1 -S) x -CH 2 CH 2 -O-(LINK 2 )] y -OR (VI) wherein each of LINK 1 and LINK 2 which may be the same or different represents a divalent linking group; R represents H, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aryl group or an acyl group; x is 1 or 2, and y varies from 2 to 20.
  • the hydrophilic colloid binder of the layers containing the dyes according to the present invention is usually gelatin.
  • Other hydrophilic colloids such as casein, polyvinyl alcohol, poly-N-vinyl pyrrolidone, sodium alginate, sodium carboxymethylcellulose, etc., can also be used either or not in combination with gelatin.
  • at least one of the hydrophilic layers of the photographic element according to this invention further comprises colloidal silica.
  • Suitable silica sols are commercially available such as the "Syton” silica sols (a trademarked product of Monsanto Inorganic Chemicals Div.), the “Ludex” silica sols (a trademarked product of du Pont de Nemours & Co., Inc.), the "Nalco” and “Nalcoag” silica sols (trademarked products of Nalco Chemical Co), the "Snowtex” silica sols of Nissan Kagaku K.K. and the "Kieselsol, Types 100, 200, 300, 500 and 600" (trademarked products of Bayer AG).
  • Particle sizes of the silica sol particles are in the range from 0.003 ⁇ m to 30 ⁇ m. The smaller particles in the range from 0.003 ⁇ m to 0.3 ⁇ m are preferred as its specific surface is larger and as its activity will be more effective.
  • the green-sensitised and red-sensitised emulsion crystals are preferably composed of tabular silver halide crystals, although tabular crystals in the blue-sensitive layer are not excluded.
  • the silver halide emulsions in the layers of the colour negative photographic element according to this invention are preferably silver bromoiodide emulsions having an iodide content from 0.4 to 3 mole %, and more preferably from 0.5 to 1.5 mole % for colour intermediate films and from 3 to 15 mole %, and more preferably from 3 to 9 mole % in the less sensitive layer, even more preferably from 4 to 7 mole %; and more preferably from 5 to 15 mole % and even more preferably from 7 to 15 mole % in the most sensitive layers of each colour sensitive arrangement for colour negative recording films.
  • These silver bromoiodide emulsion crystals can be prepared in gelatin, but also colloidal silica can be a very useful protective colloid as has been illustrated in the unpublished EP-A No. 94200933, filed April 6, 1994.
  • the transparent film support of the photographic colour negative or colour intermediate film element of the present invention is a film of cellulose triacetate, a polyalkylene terephthalate, e.g., polyethylene terephthalate, polyethylene naphthalate or polycarbonate.
  • the photographic negative-working colour film element being a colour negative recording film or a colour intermediate film
  • a backing layer on the side of the transparent film support that is opposite to that carrying the emulsion layers and is provided with an antistatic layer comprising an electroconductive polymer as, e.g., described in US-P 4,089,997, preferably an antistatic layer comprising polystyrene sulphonic acid sodium salt and even more preferred polyethylene dioxy thiophene.
  • This antistatic layer may comprise polymer beads as described in EP-S 0,080,225, these beads protruding from the antistatic layer surface and consequently acting as spacing agents to reduce contact with adjacent surfaces.
  • Samples of colour negative film elements A and B were made. Each sample had a transparent film support, a subbing layer, a red-sensitized silver halide emulsion layer comprising a cyan-forming coupler, an intermediate gelatin layer, a green-sensitized silver halide emulsion layer comprising a magenta-forming coupler, a yellow filter layer, a blue-sensitive silver halide emulsion layer comprising a yellow-forming coupler, and an antistress layer. All samples were identical except for the composition of the yellow filter layer YFL, as explained hereinafter.
  • the corresponding yellow filter layer called YFL-A and YFL-B respectively, were containing (per sq.m) as main components:
  • Both elements A and B had a blue antihalation layer between the support and the red-sensitized silver halide emulsion layer, the blue antihalation layer having a thickness of 1 ⁇ m and comprising 50 mg of the blue dye B-01 (in its ammonium salt form) and 0.7 g of gelatin per m2.
  • a sample of each of the materials A and B was individually placed in contact with a transparent chart or wedge and a first sample of each was selectively exposed to green light.
  • Samples of colour negative film elements C, D and E were made.
  • Sample C had the same composition as sample A (see Example 1) except for the spectral sensitisation of the silver bromoiodide crystals in the green-light sensitive emulsion layer having the highest speed (farther from the support in the green-sensitive layer packet).
  • the crystals of samples C, D and E were each spectrally sensitised with: 0.176 mmole of SS-3; SS-4 and SS-5, the formulae of which are given hereinafter in a molar ratio of 75:20:5.
  • the corresponding yellow filter layer in the materials C, D and E, the corresponding yellow filter layer, called YFL-C, YFL-D and YFL-E respectively, were containing the same components in the same amounts as given in Example 1. According to this invention 25 mg/m 2 of Laponite RDS were additionally added to YFL-B; 50 mg/m 2 to YFL-C. Further the same coating additives and preservatives were added to both materials as in Example 1.
EP19950201015 1995-04-21 1995-04-21 Photographisches negativ-arbeitendes Farbfilmelement Expired - Lifetime EP0738918B1 (de)

Priority Applications (2)

Application Number Priority Date Filing Date Title
DE1995618402 DE69518402T2 (de) 1995-04-21 1995-04-21 Photographisches negativ-arbeitendes Farbfilmelement
EP19950201015 EP0738918B1 (de) 1995-04-21 1995-04-21 Photographisches negativ-arbeitendes Farbfilmelement

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP19950201015 EP0738918B1 (de) 1995-04-21 1995-04-21 Photographisches negativ-arbeitendes Farbfilmelement

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EP0738918A1 true EP0738918A1 (de) 1996-10-23
EP0738918B1 EP0738918B1 (de) 2000-08-16

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0921435A1 (de) * 1997-12-02 1999-06-09 Imation Corp. Lichtempfindliche photographische Silberhalogenidelemente, die gelbe Filterfarbstoffe enthalten
EP1321805A1 (de) * 2001-12-21 2003-06-25 Eastman Kodak Company Silberhalogenidhaltiges Bilderzeugungselement beinhaltend zwischengeschaltete photograpisch nützliche Verbindungen

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH04283746A (ja) * 1991-03-12 1992-10-08 Konica Corp 色素画像形成方法
EP0582000A1 (de) * 1992-08-03 1994-02-09 Agfa-Gevaert N.V. Photographischer Farbnegativ- oder Intermediärfarbfilm

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH04283746A (ja) * 1991-03-12 1992-10-08 Konica Corp 色素画像形成方法
EP0582000A1 (de) * 1992-08-03 1994-02-09 Agfa-Gevaert N.V. Photographischer Farbnegativ- oder Intermediärfarbfilm

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Section Ch Week 9247, Derwent World Patents Index; Class G06, AN 92-385480 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0921435A1 (de) * 1997-12-02 1999-06-09 Imation Corp. Lichtempfindliche photographische Silberhalogenidelemente, die gelbe Filterfarbstoffe enthalten
US6045985A (en) * 1997-12-02 2000-04-04 Tulalip Consultoria Comercial Sociedade Unipessoal S.A. Light-sensitive silver halide photographic elements containing yellow filter dyes
EP1321805A1 (de) * 2001-12-21 2003-06-25 Eastman Kodak Company Silberhalogenidhaltiges Bilderzeugungselement beinhaltend zwischengeschaltete photograpisch nützliche Verbindungen
US6974663B2 (en) 2001-12-21 2005-12-13 Eastman Kodak Company Silver halide imaging element containing intercalated photographically useful compounds

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DE69518402D1 (de) 2000-09-21
EP0738918B1 (de) 2000-08-16
DE69518402T2 (de) 2001-03-08

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