EP0027988B1 - Matériau photographique d'halogénure d'argent sensible à la lumière - Google Patents

Matériau photographique d'halogénure d'argent sensible à la lumière Download PDF

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Publication number
EP0027988B1
EP0027988B1 EP80106379A EP80106379A EP0027988B1 EP 0027988 B1 EP0027988 B1 EP 0027988B1 EP 80106379 A EP80106379 A EP 80106379A EP 80106379 A EP80106379 A EP 80106379A EP 0027988 B1 EP0027988 B1 EP 0027988B1
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Prior art keywords
compound
compounds
gelatin
hardening
substituted
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EP80106379A
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German (de)
English (en)
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EP0027988A1 (fr
Inventor
Johannes Dr. Sobel
Wolfgang Dr. Himmelmann
Peter Dr. Bergthaller
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Agfa Gevaert AG
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Agfa Gevaert AG
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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
    • G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • G03C1/06—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with non-macromolecular additives
    • G03C1/30—Hardeners

Definitions

  • the invention relates to a light-sensitive silver halide photographic material, the gelatin layers of which have been hardened with a compound containing vinylsulfonyl groups.
  • metal salts such as chromium, aluminum or zirconium salts, aldehydes and halogen-containing aldehyde compounds, in particular formaldehyde, dialdehydes and mucochloric acid, 1,2- and 1,4-diketones such as cyclohexanedione-1,2 and quinones and chlorides of 2-basic organic Acids, such as anhydrides of tetracarboxylic acids, compounds with several reactive vinyl groups such as vinylsulfones, acrylamides, compounds with at least 2 easily cleavable, heterocyclic 3-membered rings such as ethylene oxide and ethylene imine, polyfunctional methanesulfonic acid esters and bis-a-chloroacylamido compounds.
  • metal salts such as chromium, aluminum or zirconium salts, aldehydes and halogen-containing aldehyde compounds, in particular formaldehyde, dialdehydes and mucochloric acid, 1,2- and
  • high molecular weight curing agents such as e.g. Polyacrolein or its derivatives or copolymers and alginic acid derivatives are known, which are used specifically as layer-limited curing agents.
  • the use of the compounds mentioned for photographic purposes is associated with a number of serious disadvantages. Some of these compounds are photographically active and are therefore unsuitable for hardening photographic materials, others influence the physical properties, e.g. the fragility of the gelatin layers so disadvantageous that they cannot be used. Others cause coloration or a change in pH during the curing reaction. In addition, it is particularly important for the hardening of photographic layers that the hardening reaches its maximum as soon as possible after drying so that, as in the case of mucochloric acid or formaldehyde, for example, the permeability of the material to be hardened to the developer solution does not change continuously .
  • crosslinking agents for gelatin also have a skin-damaging effect, e.g. the ethyleneimine compounds, so that their use is not appropriate for physiological reasons alone.
  • hardening agents for photographic gelatin layers are compounds with 2 or more acrylic acid amido groups in the molecule, N, N ', N " -trisacryloylhydrotriazine or methylenebisacrylamide.
  • the hardening of the compounds after some time is good, but the compounds are sparingly soluble in water, which can lead to nonuniformities in the hardening within the layer.
  • DE-C-1 100942 aromatic vinyl sulfone compounds and DE-A-1547733 nitrogen or oxygen as heteroatoms containing heterocyclic vinyl sulfone compounds are known.
  • DE-C-1 808685 and DE-A-2348194 describe bis-vinylsulfonylalkyl compounds as curing agents.
  • the known vinyl sulfone compounds have proven to be disadvantageous as curing agents in several respects. They are either not sufficiently water-soluble and require special measures to enable their use in photographic gelatin layers, or they adversely affect the drying behavior of the layers. Other of these compounds increase the viscosity of the casting compositions so that the processing of the casting compositions into layers is disturbed.
  • Known hardeners of the vinyl sulfone type also cause migration of photographic additives from one layer to the other, particularly in color photographic recording materials, which causes color changes and those of the photographic properties.
  • DE-A-2635518 discloses as curing agents reaction products which are obtained when reactions of compounds having at least 3 vinylsulfonyl groups in the molecule with compounds having a water-soluble group and a group which can react with a vinylsulfonyl group.
  • Anionic vinylsulfonyl compounds are formed.
  • these connections have disadvantages. They show strong post-curing in gelatin-containing photographic layers, i.e. their optimal effect only begins after the material has been stored for a long time. As a result, the layer swelling in the water decreases with increasing duration of storage and as a result the sensitometric data of the material change continuously.
  • the viscosity increases with increasing digestion time, which no longer permits an error-free pouring.
  • the invention is based on the object of providing a hardening agent for photographic gelatin which has sufficient water solubility for this purpose, a hardening reaction which quickly comes to its optimum effect, and has no disruptive post-hardening effect.
  • DE-C-1100942 provides information about the production processes suitable for aromatic vinyl sulfone compounds.
  • Heterocyclic vinylsulfonylalkyl compounds can be prepared in the manner described in DE-A-1547733.
  • the preparation of sulfonamide esters can be found in DE-B-1 094735 and 1178071 or GB-A-1 071 298.
  • Information about the production of vinylsulfonylalkanes can be found in DE-A-2348194.
  • amines which are used as amine salts, e.g. Chlorides or sulfates with which compounds (A) containing vinylsulfonyl groups can be reacted are, for example, the following compounds (B):
  • the amines of the formula (B) are commercially available products.
  • the curing agents according to the invention - hereinafter referred to as (C) - contain at least 2 vinylsulfonyl groups and at least one group obtained by reacting a vinylsulfonyl group with an amine (compounds (B)) in the molecule.
  • the reaction products are water-soluble and have excellent crosslinking properties for gelatin-containing layers.
  • the compounds (C) are obtained by reacting the solutions of the compounds (A) with solutions of the compounds (B) in the form of their amine salts or as free amines, in the latter case the amines being converted into the amine salts after the reaction has ended, for example by addition corresponding amounts of an acid such as HCl or H Z S0 4 .
  • the molar ratios of the vinylsulfonyl compounds and amines in the reaction vary depending on the number of vinylsulfonyl groups of the compounds (A). Basically, the reaction product contains at least two unreacted vinyl sulfone groups. 1 mol of compound (A) is preferably reacted with 0.5-1 mol of compound (B).
  • reaction products are preferably used as they are after the reaction, i.e. without isolating them. However, the reaction products can also be isolated and purified.
  • the cationic compounds of the invention are generally used as curing agents as they are obtained in the production process. However, if the purpose so requires, they can also be used in more dilute or concentrated solutions. Incidentally, the hardening of the gelatin with the hardening agents of the invention can be carried out according to all methods customary for this.
  • the hardeners are generally incorporated into the casting solutions in an amount of 0.01 to 100% by weight and preferably 0.1 to 10% by weight, based on the dry weight of the gelatin.
  • the timing of the addition is not critical.
  • Silver halide emulsions will expediently add the hardener after chemical ripening.
  • the hardening agent can of course also be introduced in the form of a solution using the so-called overlay process in a layered structure.
  • photographic layers are to be understood very generally as layers which are used in the context of photographic materials, for example light-sensitive silver halide emulsion layers, protective layers, filter layers, antihalo layers, backing layers or very generally photographic auxiliary layers.
  • light-sensitive emulsion layers for which the curing method according to the invention is excellently suitable, mention may be made, for example, of layers which are based on non-sensitized emulsions, X-ray emulsions and other spectrally sensitized emulsions.
  • the curing method of the invention has also proven itself for curing the gelatin layers used for the various black-and-white and color photographic processes, such as negative, positive and diffusion transfer processes or printing processes.
  • the method according to the invention has proven to be particularly advantageous for the hardening of photographic layer dressings which are intended for carrying out color photographic processes, e.g. those which contain emulsion layers with color couplers or emulsion layers which are intended for treatment with solutions which contain color couplers.
  • the effect of the compounds used in the manner according to the invention is not impaired by the usual photographic additives.
  • the hardening agents are also indifferent to photographically active substances, e.g. water-soluble and emulsified water-insoluble color components, stabilizers and sensitizers. Furthermore, they have no adverse effect on the light-sensitive silver halide emulsions.
  • the emulsion layers can be any known silver halide, e.g. Contain silver chloride, silver iodide, silver bromide, silver iodobromide, silver chlorobromide and silver chlorobiodobromide.
  • the emulsions can be chemically sensitized by noble metal compounds, e.g. through compounds of ruthenium, rhodium, palladium, iridium, platinum, gold, ammonium chloropalladate, potassium chloroplatinate, potassium chloropalladite, or potassium chloroaurate. They can also contain special sensitizers for sulfur compounds, tin (11) salts, polyamines or polyalkylene oxide compounds.
  • the emulsions can be optically sensitized with cyanine dyes, merocyanine dyes and mixed cyanine dyes.
  • the emulsions can be a wide variety of couplers, for example colorless couplers, colored couplers, stabilizers such as mercury bonds, triazole compounds, azaindene compounds, benzothiazolium compounds or zinc compounds, wetting agents, such as dihydroxyalkanes, agents which improve the film-forming properties, for example the water-dispersible, particulate copolymers or maleic polymers, styrene / maleic acid or styrene polymer, obtained in the emulsion polymerization of alkyl acrylate or alkyl methacrylate / acrylic acid or methacrylic acid copolymers Styrene / maleic anhydride half alkyl ester copolymers, coating aids, such as polyethylene glycol lauryl ether, and a wide variety of other photographic additives.
  • couplers for example colorless couplers, colored couplers, stabilizers such as mercury bonds, triazole compounds, azaindene compounds, benzo
  • the hardening agents of the invention do not have the property of suddenly having their hardening effect, nor do they tend to over-harden gelatin layers. Both properties represent a significant advantage for the manufacturing process of photographic materials.
  • the layered structure is then dried.
  • the photographic film thus produced serves as a comparison material in the following.
  • the production of the film is repeated, with the individual layers per film sample being each one of the curing agents C / 1, C / 2, C / 3, C / 4, C / 11 and C / 15 in an amount of 0.02 g per gram of gelatin.
  • test object is developed as a black sheet in a conventional color development process and weighed after the final bath after wiping off the excess water. The sample is then dried and weighed again. The difference from the area of the test object to 1 m 2 converts the water absorption per m 2 .
  • the swelling is measured gravimetrically after treatment of a test strip in distilled water at 22 ° C. for 10 minutes. It is characterized by the swelling factor:
  • a metal tip of a defined size is passed over the wet layer and loaded with increasing weight.
  • the wet scratch resistance is indicated by the weight at which the tip leaves a visible scratch mark on the layer.
  • a high weight corresponds to a high wet scratch resistance.
  • a color control material is produced by successively applying the following layers onto a paper base laminated with polyethylene and provided with an adhesive layer, the emulsion layers containing the usual additions of wetting agents, stabilizers, etc.:
  • 1, 2 and 5 g of the compounds according to the invention are added to 100 g of gelatin in the form of the aqueous solutions at pH 6.2 to 100 ml of ready-to-pour photographic silver bromide gelatin emulsion which contains 10% by weight gelatin.
  • the mixtures are stirred well and poured onto a prepared cellulose triacetate base using a conventional casting machine and dried. The usual additions are not changed. Details regarding the composition of the samples, the various test conditions and finally the results are summarized in Table 3 below.
  • the layer melting point 100 ° C. is obtained after standing for 1 day with the exclusion of air at 22 ° C., a sign of a relatively fast and uniform crosslinking. All photographic properties are preserved. Veil and sensitivity are not changed. Liability on the pad is good.
  • Compound C / 1 was used as the curing agent according to the invention. 2% by weight hardener based on gelatin was added to the casting solutions. The casting solutions were poured onto a cellulose triacetate support provided with an adhesive layer and dried (layer thickness 10 ⁇ m).
  • the table shows that the comparative samples VV1 and VV2 harden strongly during long-term storage.
  • the swelling factors are initially relatively high and decrease significantly after long-term storage. This lowers the maximum densities of the developed film samples (slowed through development or reduced silver opacity). If you are aiming for materials that show good developability and medium hardening after long-term storage, it is necessary to use fewer hardening agents. However, one has to accept the disadvantage of having strongly swelling, ie too soft, photographic layers for shorter storage times.
  • the compound C / 1 according to the invention used for comparison cures the material relatively quickly to an average degree of hardening and then shows only insignificant post-hardening in the case of long-term storage.
  • the hardeners of the invention thus give a balanced hardening of the photographic material, which is largely independent of the storage.

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

Claims (8)

1. Elément photographique photosensible à l'halogénure d'argent constitué d'un support de couches sur lequel est appliquée au moins une couche contenant de la gélatine et durcie avec un composé contenant des groupes vinylsulfonyle, caractérisé en ce que le composé durcissant est le produit réactionnel (dont la molécule contient au moins deux groupes vinylsulfonyle libres) de deux composés répondant aux formules générales suivantes:
Figure imgb0066
dans laquelle:
R représente un groupe d'hydrocarbure aliphatique n-valent pouvant être substitué, un groupe d'hydrocarbure aromatique n-valent pouvant être substitué, un groupe cycloalkyle n-valent pouvant être substitué, ou un groupe hétérocyclique n-valent pouvant être substitué, et
n est un nombre entier de 3 à 6,

et
Figure imgb0067
dans laquelle:
RI et R2 sont identiques ou différents et représentent chacun un atome d'hydrogène ou un groupe alkyle inférieur,
R3 représente un groupe alkyle, un groupe ami- noalkyle, un groupe cycloaliphatique pouvant être substitué, un groupe aromatique pouvant être substitué, ou encore un noyau hétérocyclique pentagonal ou hexagonal pouvant être relié à l'atome d'azote du composé (B) directement ou par l'intermédiaire d'un groupe contenant du carbone, ou
R2 et R3 ensemble représentent les atomes nécessaires pour compléter un système à noyau hétérocyclique, le noyau pouvant contenir, en plus de l'atome d'azote, un atome d'oxygène ou un autre atome d'azote.
2. Elément photosensible suivant la revendication 1, caractérisé en ce qu'on le durcit avec un produit réactionnel d'un des composés:
Figure imgb0068
avec un des composés
Figure imgb0069
3. Elément photosensible suivant la revendication 1, caractérisé en ce que le composé durcissant est le produit réactionnel de 1 mole du composé
C(CH2S02CH=CH2)4 et de 0,75 mole du composé
Figure imgb0070
4. Elément photosensible suivant la revendication 1, caractérisé en ce que le composé durcissant est le produit réactionnel de 1 mole du composé
C(CH2So2CH=CH2)4 et de 0,5 mole du composé
Figure imgb0071
5. Elément photosensible suivant une des revendications 1 à 4, caractérisé en ce qu'il contient 0,1 à 10% en poids du composé durcissant, calculé sur le poids sec de la gélatine.
6. Elément photosensible suivant les revendications 1 à 5, caractérisé en ce qu'il est un élément à plusieurs couches pour la photographie en couleurs.
EP80106379A 1979-10-30 1980-10-20 Matériau photographique d'halogénure d'argent sensible à la lumière Expired EP0027988B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2943806 1979-10-30
DE19792943806 DE2943806A1 (de) 1979-10-30 1979-10-30 Lichtempfindliches photographisches silberhalogenidmaterial

Publications (2)

Publication Number Publication Date
EP0027988A1 EP0027988A1 (fr) 1981-05-06
EP0027988B1 true EP0027988B1 (fr) 1982-05-05

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EP80106379A Expired EP0027988B1 (fr) 1979-10-30 1980-10-20 Matériau photographique d'halogénure d'argent sensible à la lumière

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EP (1) EP0027988B1 (fr)
CA (1) CA1146000A (fr)
DE (2) DE2943806A1 (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3523360A1 (de) * 1985-06-29 1987-01-08 Agfa Gevaert Ag Lichtempfindliches fotografisches aufzeichnungsmaterial
DE3628717A1 (de) * 1986-08-23 1988-02-25 Agfa Gevaert Ag Haertungsmittel fuer proteine, eine damit gehaertete bindemittelschicht und eine solche schicht enthaltendes fotografisches aufzeichnungsmaterial
DE3708541A1 (de) * 1987-03-17 1988-10-13 Agfa Gevaert Ag Haertungsmittel fuer proteine, eine damit gehaertete bindemittelschicht und ein eine solche schicht enthaltendes fotografisches aufzeichnungsmaterial
JPS63241539A (ja) * 1987-03-30 1988-10-06 Fuji Photo Film Co Ltd ゼラチンの硬化方法
JP2528344B2 (ja) * 1988-02-10 1996-08-28 富士写真フイルム株式会社 ハロゲン化銀カラ―写真感光材料
US5187259A (en) * 1990-11-14 1993-02-16 Eastman Kodak Company Chain extended gelatin
DE69317783T2 (de) * 1993-12-02 1998-11-12 Agfa Gevaert Nv Bildelement zur Herstellung einer lithographischen Druckplatte durch das Silbersalzdiffusion-Übertragungsverfahren
US5411856A (en) * 1994-01-10 1995-05-02 Eastman Kodak Company Carbamyl-substituted bis(vinylsulfonyl) methane hardeners

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1622260A1 (de) * 1968-02-16 1969-11-27 Agfa Gevaert Ag Verfahren zur Haertung von photographischen,gelatinehaltigen Schichten
JPS5144164A (en) * 1974-10-14 1976-04-15 Konishiroku Photo Ind Zerachinno kokaho
US4142897A (en) * 1975-08-09 1979-03-06 Konishiroku Photo Industry Co., Ltd. Gelatino silver halide photographic material hardened with a reaction product of a vinylsulfonyl compound and a water soluble compound

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Publication number Publication date
DE3060375D1 (en) 1982-06-24
EP0027988A1 (fr) 1981-05-06
US4349624A (en) 1982-09-14
DE2943806A1 (de) 1981-05-14
CA1146000A (fr) 1983-05-10

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