EP0049449A1 - Matériau photosensible à base d'halogénure d'argent pour enregistrement photographique - Google Patents

Matériau photosensible à base d'halogénure d'argent pour enregistrement photographique Download PDF

Info

Publication number
EP0049449A1
EP0049449A1 EP81107680A EP81107680A EP0049449A1 EP 0049449 A1 EP0049449 A1 EP 0049449A1 EP 81107680 A EP81107680 A EP 81107680A EP 81107680 A EP81107680 A EP 81107680A EP 0049449 A1 EP0049449 A1 EP 0049449A1
Authority
EP
European Patent Office
Prior art keywords
gelatin
dione
alkyl
ring
compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP81107680A
Other languages
German (de)
English (en)
Other versions
EP0049449B1 (fr
Inventor
Hans Dr. Langen
Erich Dr. Wolff
Erwin Dr. Ranz
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.)
Agfa Gevaert AG
Original Assignee
Agfa Gevaert AG
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 Agfa Gevaert AG filed Critical Agfa Gevaert AG
Publication of EP0049449A1 publication Critical patent/EP0049449A1/fr
Application granted granted Critical
Publication of EP0049449B1 publication Critical patent/EP0049449B1/fr
Expired 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
    • 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
    • G03C1/33—Spot-preventing agents
    • 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
    • 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 photographic silver halide recording material which, in addition to a crosslinking agent which activates the carboxyl groups of the gelatin used as binders, contains a compound which is capable of reacting as an aldehyde scavenger.
  • Photographic recording materials usually consist of a layer support and light-sensitive gelatin-containing silver halide emulsion layers and / or non-light-sensitive auxiliary layers, likewise containing gelatin, applied thereon.
  • the light-sensitive silver halide gelatin emulsion layers of color photographic recording materials contain the color components required to form the image dyes in the three primary colors.
  • the multilayer recording materials mentioned here in black and white and color photography and their production are generally known and are described, for example, in the "Photography” chapter in Ullmann's Encyclopedia of Industrial Chemistry, 4th edition, volume 18
  • crosslinking agents which are also called hardeners. Both inorganic and organic, photographically inert compounds which can crosslink the gelatin via the carboxyl groups or the amino groups are suitable as hardening agents.
  • curing agents are aldehydes, e.g. Formaldehyde, glyoxal, glutaraldehyde, aldehyde acids, e.g. Mucochloric acid, diketones, e.g. Diacetyl, dihalides, e.g.
  • 1,3-dichloropropanol bis-vinyl sulfone compounds, diisocyanate bisulfite compounds, bis-epoxides, bisacyridines, peptide reagents such as carbodiimides, N-carbamoylpyridinium and isoxazolium salts or substituted 2,4-dichlorotriazines, e.g. N.N'.N "-Trisacryloyl-perhydro-s-triazine called.
  • aldehydes such as formaldehyde, glyoxal, glutaraldehyde or succinaldehyde as curing agents are associated with certain difficulties.
  • aldehydes can not only bring about a crosslinking of the gelatin layers that is difficult to limit, they can also improve the functionality of the color components contained in the layers and they can give rise to fog.
  • This disadvantageous effect is also to be expected if the aldehydes have not been specifically incorporated into the photographic materials, but instead have penetrated into the photographic layers during an unintended storage of the photographic material in an aldehyde-containing atmosphere.
  • This situation can occur when photographic materials are stored in furniture that is made of plywood that has been glued with a formalin-containing adhesive, such as a melamine-formaldehyde resin or a phenol-formaldehyde resin. If a photographic material is now stored in such pieces of furniture, then the formaldehyde originating from the gluing can cause a more or less strong veiling of the photographic layers, which in any case affects the quality of the photographic images produced with this material. If the photographic material is a color photographic material, the quality loss caused by the effect of the aldehyde will be even more blatant, since in this case the ⁇ compensation of the three emulsion layers producing the color image will also be disturbed.
  • a formalin-containing adhesive such as a melamine-formaldehyde resin or a phenol-formaldehyde resin.
  • aldehyde scavengers In order to avoid the described disadvantages caused by aldehydes, attempts have been made to incorporate so-called aldehyde scavengers into the photographic materials, which are compounds which are able to trap the aldehyde.
  • DE-OS 1 772 816 it is known from DE-OS 1 772 816 to add photographic layers, for example N, N'-ethylene urea, 2,3-dihydroxynaphthalene or dimedone, in order to fix formaldehyde.
  • photographic layers for example N, N'-ethylene urea, 2,3-dihydroxynaphthalene or dimedone.
  • DE-OS 2,332,426 a photographic recording material is described which contains in one of its colloid layers in addition to a V inylsulfonylhärter an acyclic urea as Aldehydentferner.
  • U.S. Patent 3,652,278 relates to a method of reducing fog in photographic materials to be stored in an atmosphere containing formaldehyde.
  • US Pat. No. 2,309,492 It is also known from US Pat. No. 2,309,492 to process photographic materials which contain an aldehyde hardener in the presence of an organic compound which is capable of reacting with the aldehyde.
  • the compounds include hydroxylamines, hydrazines, hydrazo compounds, semicarbazides, naphthalenediamines and dimethyldihydroresorcinol.
  • US Pat. No. 3,168,400 also relates to a method for stabilizing photographic images. The method is to harden the binder of the photographic material before developing the material and after exposure to an aldehyde, and then removing the unused aldehyde by treatment with the aqueous solution of an amine compound.
  • Suitable amines are, for example, hydroxylamine, semicarbazide, hydrazine, biuret, Aminoguanidine etc.
  • Aldehyde-containing photographic materials are treated according to DE-OS 2 227 144 in baths which contain hydroxylamine or a water-soluble salt of hydroxylamine and an aromatic polyhydroxyl compound with 2 hydroxyl groups in the ortho position, for example an o-dihydroxy compound from the benzene series.
  • the invention has for its object to develop a photographic recording material which is protected against fogging, especially after prolonged storage under the action of aldehydes, and whose contrast and sensitivity are not adversely affected by such storage.
  • ring carbon atoms with 1 to 5 carbon atoms containing straight-chain or branched Be alkyl groups carry a fused cycloaliphatic or aromatic 6-membered ring or an aliphatic 5- or 6-ring in spiro linkage. can.
  • the total number of carbon atoms in the substituents is not greater than 6.
  • color photographic recording materials the gelatin layers of which are hardened with a hardening agent from the group consisting of the carbamoylonium, carbamoylpyridinium and carbamoyloxypyridinium salts and which also contain one of the diketo compounds according to the invention. are largely immune to the harmful effects caused by aldehydes.
  • a hardening agent from the group consisting of the carbamoylonium, carbamoylpyridinium and carbamoyloxypyridinium salts and which also contain one of the diketo compounds according to the invention.
  • the purple-4-equivalency couplers such as those e.g. described in DE-OS 2 015 867, DE-OS 2 408-665 and US Pat. No. 3,062,653.
  • the cyclic diketo compounds of the invention can be used in the layers of photographic recording materials together with the curing agents mentioned, without the two additives adversely affecting one another in any way.
  • the diketo compounds can be added to the casting solution of one or more of the sub-layers of the photographic recording material, depending on the conditions of the casting. In general, it is sufficient to coat the recording material with a top layer which contains the diketo compound. The layered structure is then adequately protected against the penetration of aldehyde vapors.
  • the application of the diketo compounds in this form has in particular - sondere in color photographic multilayered materials proven.
  • the amount of the diketo compound applied with the top layer can be dimensioned such that they diffuse into the layer structure during the drying process The resulting compound is evenly distributed over the layers of the dressing containing the color components, thereby achieving an optimal protective effect.
  • the diketo compounds can be introduced in all water-miscible solvents or in water itself. Particularly advantageous are low-boiling solvents which can be easily removed when the photographic material is poured on, e.g. Methanol, ethanol, propanol, (t) -butanol, acetone, methyl ethyl ketone, acetonitrile.
  • cyclic diketo compounds to be used are understandably dependent on the extent to which protection of the recording material is required. They will therefore depend on the aldehyde concentration to be considered, the sensitivity of the components within the photographic material to be protected and finally the solubility of the cyclic diketo compounds used.
  • at least 0.05 mol of the cyclic diketo compound per mol of hardener is sufficient.
  • the use is from 0.1 to 6 moles per mole of curing agent diketo compound, said amounts of from 0.2 to 2 moles per mole of curing agent as Diketoverbindun g have proven particularly suitable.
  • hydrophilic colloids can be used in the layers of the recording material in addition to the gelatin, colloidal albumin, agar, gum arabic, dextrans, alginic acid, cellulose derivatives, eg up to an acetyl content 19-26% hydrolyzed cellulose acetate, polyacrylamide, imidatinstrumente polyacrylamides, Cin, V inylalkoholpolymere with urethane / Carboxylic acid groups or cyanoacetyl groups, such as vinyl alcohol, vinyl cyanoacetate copolymers, polyvinyl alcohols, polyvinyl pyrrolidones, hydrolyzed polyvinyl acetates, polymers such as those obtained in the polymerization of proteins and saturated acylated proteins with monomers with vinyl groups, polyvinylamines, polyaminoethyl methacrylates and polyethylenimine are used.
  • cyclic diketo compounds used in accordance with the invention in connection with the carbamoylonium, carbamoylpyridinium and carbamoyloxypyridinium hardeners have proven to be particularly advantageous in that they in no way affect the sensitometric properties of the photographic material affect, although they would in principle be able to couple due to the presence of an active carbon atom.
  • the compounds known as aldehyde scavengers they have a high reactivity towards aldehydes, which makes the use of the curing agent mentioned possible in practice.
  • the samples were sized 35x250 mm for 7 days at room temperature in a vessel with a volume of 27 l containing a mixture of 650 g glycerol, 350 g water and 1 ml 30% formaldehyde, stored and then checked in comparison with a normally stored material. The purple residual color density remaining in% of the color density 1.5 via veil was evaluated in each case.
  • the effect of the present 1,3-diketo compounds is compared with that of known aldehyde removers.
  • the diketo compounds and the comparison compounds 170 mg each of layer 7 of example 1, 180 mg of layer 8 of example 1 and 100 mg of layer 9 of example 1 were added.
  • Table 2 shows that practically only the cyclic 1,3-diketo compounds of the invention have a protective effect.
  • diketo compound no. 26 are added to layers 1 and 2 from example 1 and 145 mg to layers 7, 8 and 9 of example 1. In all cases, compound no. II / 10. used. A purple color density of 90% was measured on all 5 samples after storage under a formalin atmosphere. As the example shows, the same protective effects are achieved it does not matter whether the diketo compound is embedded in a layer which lies above or below the purple layer to be protected or which is the purple layer itself.

Landscapes

  • 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)
  • Plural Heterocyclic Compounds (AREA)
  • Pyrane Compounds (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
EP81107680A 1980-10-08 1981-09-28 Matériau photosensible à base d'halogénure d'argent pour enregistrement photographique Expired EP0049449B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19803037912 DE3037912A1 (de) 1980-10-08 1980-10-08 Lichtempfindliches fotografisches silberhalogenid-aufzeichnungsmaterial
DE3037912 1980-10-08

Publications (2)

Publication Number Publication Date
EP0049449A1 true EP0049449A1 (fr) 1982-04-14
EP0049449B1 EP0049449B1 (fr) 1983-09-28

Family

ID=6113849

Family Applications (1)

Application Number Title Priority Date Filing Date
EP81107680A Expired EP0049449B1 (fr) 1980-10-08 1981-09-28 Matériau photosensible à base d'halogénure d'argent pour enregistrement photographique

Country Status (5)

Country Link
US (1) US4418142A (fr)
EP (1) EP0049449B1 (fr)
JP (1) JPS57100423A (fr)
CA (1) CA1164709A (fr)
DE (2) DE3037912A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0247482A3 (en) * 1986-05-28 1988-08-03 Miles Laboratories, Inc. Hardened reagent coatings, and processes for the preparation thereof
EP0172463B1 (fr) * 1984-08-24 1990-05-09 Shionogi & Co., Ltd. Procédé pour la préparation de dérivés de l'acide thiazole glutaconique

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS60258545A (ja) * 1984-05-10 1985-12-20 Fuji Photo Film Co Ltd ハロゲン化銀カラ−写真感光材料
JPS60237445A (ja) * 1984-05-10 1985-11-26 Fuji Photo Film Co Ltd ハロゲン化銀カラ−写真感光材料
US4639415A (en) * 1984-09-17 1987-01-27 Konishiroku Photo Industry Co., Ltd. Silver halide color photographic material containing a magenta color image-forming coupler
JP2565766B2 (ja) * 1988-02-09 1996-12-18 富士写真フイルム株式会社 ハロゲン化銀写真感光材料
JPH0431371U (fr) * 1990-07-11 1992-03-13
DE69535305T2 (de) * 1994-09-09 2007-06-21 Koyama, Shozo, Matsumoto Mittel zum herabsetzen von molekülfunktionen
US20200031983A1 (en) 2017-02-09 2020-01-30 Dow Global Technologies Llc Polyurethanes having low levels of aldehyde emissions
WO2020024231A1 (fr) 2018-08-02 2020-02-06 Dow Global Technologies Llc Procédés de réduction des émissions d'aldéhyde dans des mousses de polyuréthane
WO2020024236A1 (fr) 2018-08-02 2020-02-06 Dow Global Technologies Llc Procédés de réduction des émissions d'aldéhyde dans des mousses de polyuréthane

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3447926A (en) * 1965-01-22 1969-06-03 Eastman Kodak Co Color photographic silver halide elements containing 4-substituted urazoles and/or cycloalkane-1,3-diones
DE1772816A1 (de) * 1967-07-08 1970-10-22 Fuji Photo Film Co Ltd Lichtempfindliches photographisches Halogensilbermaterial
US3811891A (en) * 1972-06-27 1974-05-21 Eastman Kodak Co Silver halide photographic element containing a vinylsulfonyl compound hardener and an acrylic urea as formaldehyde scavenger
DE2439551C2 (de) * 1974-08-17 1985-11-21 Agfa-Gevaert Ag, 5090 Leverkusen Verfahren zur Härtung photographischer Schichten

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Keine Entgegenhaltungen *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0172463B1 (fr) * 1984-08-24 1990-05-09 Shionogi & Co., Ltd. Procédé pour la préparation de dérivés de l'acide thiazole glutaconique
EP0247482A3 (en) * 1986-05-28 1988-08-03 Miles Laboratories, Inc. Hardened reagent coatings, and processes for the preparation thereof

Also Published As

Publication number Publication date
JPH0226211B2 (fr) 1990-06-08
DE3161041D1 (en) 1983-11-03
US4418142A (en) 1983-11-29
JPS57100423A (en) 1982-06-22
CA1164709A (fr) 1984-04-03
DE3037912A1 (de) 1982-05-27
EP0049449B1 (fr) 1983-09-28

Similar Documents

Publication Publication Date Title
EP0549976B1 (fr) Système antihalo blanchissable
DE857885C (de) Stabilisatoren fuer photographische Emulsionen
EP0011051B1 (fr) Matériel d'enregistrement photographique en couleurs, procédé pour sa stabilisation et préparation d'images photographiques en couleurs
DE964654C (de) Photographisches Material mit einer ultraviolettabsorbierenden Schicht
EP0049449B1 (fr) Matériau photosensible à base d'halogénure d'argent pour enregistrement photographique
DE2439551A1 (de) Verfahren zur haertung photographischer schichten
DE2043270B2 (de) Farbentwickeltes farbphotographisches aufzeichnungsmaterial
DE2541267C3 (de) Photographisches Aufzeichnungsmaterial
DE2538889A1 (de) Verfahren zur einarbeitung eines oelloeslichen zusatzes in ein lichtempfindliches photographisches silberhalogenidmaterial
DE3148108C2 (fr)
DE2043271A1 (de) Lichtempfindliches Farbfotomatenal
DE2648286C3 (de) Verfahren zum Härten von photographischen Silberhalogenidemulsionen
EP0181289A2 (fr) Procédé pour stabiliser un matériau photographique contenant un coupleur magenta
DE19714614A1 (de) Farbfotografisches Silberhalogenidmaterial
DE69201848T2 (de) Verfahren zum Härten von Gelatine.
EP0237887B1 (fr) Procéde de préparation d'un matériau d'enregistrement photographique
DE2241400A1 (de) Lichtempfindliches photographisches silberhalogenidmaterial
DE2036998A1 (de) Verfahren zur Vernetzung von photo graphischen Gelatineschichten
DE1547664A1 (de) Mehrschichtiges farbphotographisches Material
DE1130283B (de) Verfahren zum Haerten photographischer Schichten
EP0023670A1 (fr) Emulsion photographique, procédé de production et matériaux photographiques
DE19617770A1 (de) Farbfotografisches Silberhalogenidmaterial
DE2008113A1 (de) Verfahren zum Härten photographischer Gelatineschichten
DE2332755A1 (de) Lichtempfindliches, lithographisches silberhalogenidaufzeichnungsmaterial
DE1597496A1 (de) Verfahren zur Haertung von photographischen,gelatinehaltigen Schichten

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

17P Request for examination filed

Effective date: 19810928

AK Designated contracting states

Designated state(s): BE CH DE FR GB IT

ITF It: translation for a ep patent filed
GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Designated state(s): BE CH DE FR GB IT LI

REF Corresponds to:

Ref document number: 3161041

Country of ref document: DE

Date of ref document: 19831103

ET Fr: translation filed
PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed
REG Reference to a national code

Ref country code: GB

Ref legal event code: 746

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: BE

Payment date: 19900905

Year of fee payment: 10

ITTA It: last paid annual fee
PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: CH

Payment date: 19901029

Year of fee payment: 10

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LI

Effective date: 19910930

Ref country code: CH

Effective date: 19910930

Ref country code: BE

Effective date: 19910930

BERE Be: lapsed

Owner name: AGFA-GEVAERT A.G.

Effective date: 19910930

REG Reference to a national code

Ref country code: CH

Ref legal event code: PL

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 19920817

Year of fee payment: 12

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 19920918

Year of fee payment: 12

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 19920922

Year of fee payment: 12

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Effective date: 19930928

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 19930928

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19940531

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Effective date: 19940601

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST