US3129100A - Developing accelerators for silver halide emulsion layers - Google Patents

Developing accelerators for silver halide emulsion layers Download PDF

Info

Publication number
US3129100A
US3129100A US179472A US17947262A US3129100A US 3129100 A US3129100 A US 3129100A US 179472 A US179472 A US 179472A US 17947262 A US17947262 A US 17947262A US 3129100 A US3129100 A US 3129100A
Authority
US
United States
Prior art keywords
compound
cyanoethoxyethyl
developer
hours
amine
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.)
Expired - Lifetime
Application number
US179472A
Other languages
English (en)
Inventor
Grabhofer Herbert
Schuler Horst
Ulrich Hans
Randolph August
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 NV
Original Assignee
Agfa 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 AG filed Critical Agfa AG
Application granted granted Critical
Publication of US3129100A publication Critical patent/US3129100A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C07C309/66—Methanesulfonates
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03B—APPARATUS OR ARRANGEMENTS FOR TAKING PHOTOGRAPHS OR FOR PROJECTING OR VIEWING THEM; APPARATUS OR ARRANGEMENTS EMPLOYING ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ACCESSORIES THEREFOR
    • G03B21/00—Projectors or projection-type viewers; Accessories therefor
    • G03B21/10—Projectors with built-in or built-on screen
    • G03B21/11—Projectors with built-in or built-on screen for microfilm reading
    • G03B21/118—Reader-printers
    • 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
    • G03C1/04—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein with macromolecular additives; with layer-forming substances
    • G03C1/043—Polyalkylene oxides; Polyalkylene sulfides; Polyalkylene selenides; Polyalkylene tellurides
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/135—Cine film
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/167—X-ray

Definitions

  • This invention concerns a new class of developing accelerators which are chemically characterized by at least one quaternary nitrogen atom substituted by a cyanoethoxyethyl radical as well as a process for developing silver halide emulsion layers.
  • onium salts are similar in their action to the quaternary nitrogen compounds, for example quaternary phosphonium or ternary sulphonium salts.
  • charged onium groups may be present in the molecule.
  • onium salts are most highly effective as development accelerators when alkali developers containing solely hydroquinone as developer compound are used.
  • R o in which R and R stand for alkyl, aralkyl, phenyl, cyanoethyl, or cyanoethoxyethyl or for methylene groups or atoms necessary for completing a heterocyclic ring such as morphohne, piperidine and the like; R represents alkyl,
  • aralkyl phenyl, cyanoethoxyethyl or a radical selected from those having the following general formulae wherein R and R have the meaning specified above;
  • X represents any desired anion, such as a halide, toluenesulfonate or alkyl sulphate anion. It may be pointed out that the anion is not especially critical and is selected according to the requirements of the special composition or emulsion in which the compound is to be used;
  • m is an integer from 2-5, n from 26 and p from 1-100, preferably 1-7.
  • ethylene oxide chains of the compounds represented by the above general formula can be replaced with other alkylene oxide chain such as propylene oxide or butylene oxide chains.
  • the quaternary salts can either be added to the developer or to the emulsion or to both simultaneously.
  • the acceleration effect of the compounds according to the invention is not restricted to certain types of emulsions or developers. It is also apparent with color developers containing aromatic amine developing compounds or with emulsions containing optical or chemical sensitizers such as sulphur compounds, salts of precious metals such as ruthenium, rhodium, palladium, iridium or platinum, furthermore, iodine salts, reducing agents, polyalkylene oxides, mercuric compounds, stabilizing agents such as compounds of the azaindene series, e.g., 4-hydroxy-6-methyl-1,3,3a,7-tetra-azaindene.
  • the accelerators according to the invention can also be advantageously used with fixing developers. They may also surprisingly be used at the same time as anti-fogging agents.
  • COMPOUND I (a) N,N-Dimethyl-N-Cyanoethoxyethylamine (b) Dimethyl-Phenethyl-Cyanoethoxyethyl-Ammonium Chloride 14.2 g. of the aforementioned amine (Ia) and 14 g. of 2-chloroethyl benzene are heated while stirrmg for 2 hours to 150 C., 100 cc. of acetone and the quantity of ethanol (about 10 ml.) necessary for forming a solution are then added. On cooling, 88 g. of quaternary salt with a melting point of 123 C. crystallize out.
  • COMPOUND 11 (a) N,N-Diethyl-N-Cyanoethoxyethylamine 117 g. of diethylaminoethanol and 100 g. of sodium hydroxide are dissolved in 250 cc. of water and 53 g. of acrylonitrile are added dropwise while stirrlng at 45 C. The mixture is left standing for 5 hours at room temperature and is then extracted by shaking three times with methylene chloride, using 250 cc. on each occasion. After distilling off the methylene chloride, an oil is left which is fractionated in vacuo.
  • COMPOUND III (a) N,N-Dibutyl-N-Cyanoethoxyethy[amine 2 g. of sodium methylate are dissolved in 173 g. of di-n-butylethanolamine and 53 g. of acrylonitrile are added while stirring at 35 C. The mixture is left for 6 hours at room temperature and is then stirred with 200 cc. of water, cc. of 25 percent sodium hydroxide solution and 500 cc. of methylene chloride. 155 g. of amine with the boiling point 169 C./ 13.5 torr are recovered from the methylene chloride phase after vacuum distillation.
  • COMPOUND IV Dim ethyl-( p -Chlorobenzy l-Cyanoethoxyethy l-Ammonium Bromide 14.2 g. of N,N-dimethyl-N-cyanoethoxyethylamine (Ia) and 20.5 g. of 4-chlorobenzy1 bromide are thoroughly mixed at room temperature. After 1 hour, crystals have separated out, and these are washed with acetone.
  • COMPOUND V Dim ethyl-4-Nitrobenzy l-Cyanoethoxyethyl- Ammonium Chloride 14.2 g. of N,N-dimethyl-N-cyanoethoxyethyl (Ia) and 17.1 g. of p-nitrobenzyl chloride are heated for 5 hours under reflux in 50 cc. of acetone. The precipitated crystals are suction-filtered and recrystallized from a mixture of acetone and alcohol (10.1).
  • Crystals have a melting point of C. Yield 25 g.
  • COMPOUND XVI E Zhylenc-B is-[N ,N ,N ',N -T etra-M ethyl-N ,N -Di- (Cyanoethoxyethyl ]-A mmonium-Bromide Prepared according to Compound XIII using 1,2-dibromoethane as starting compound.
  • COMPOUND XVII (a) Diethylene-Glycol-Di-Methane-Snlphonic Acid E ter 114.5 g. of methane-sulfo-chloride are added in portions at 0 C. to a solution of 53 g. of diethtylene glycol in 200 .cc. of dried pyridine. After stirring for 1 hour at 10 C. the mixture is poured on ice water, acidified with aqueous hydrochloride, separated with common salt and shaken three times each with 300 cc. of methylene chloride. The collected methylene chloride extracts are dried with sodium sulphate and evaporated. Crystals are obtained having a melting point of 5556 C. after recrystallization from alcohol.
  • a 20 percent aqueous solution is used for photographic applications.
  • COMPOUND XVIII (a) T riethylene Glycol Di-p-Toluene SulfOnic Acid Ester 75 g. of triethylene glycol dissolved in 200cc. of dried pyridine are reacted with 190 g. of toluene sulpho-chloride at 0 C. Further processing is accomplished according to Example XVII. A crystallized compound is obtained which melts after recrystallization from ethanol at 73-74 C.
  • COMPOUND XIX (a) Ethoxy ethyl 0..., Bis [N,N-Dimethyl-N,N,N',N- Tetra-(Cyanoethoxyethyl)JAmmonium-Methane Sulfanate 10.4 g. of diethylene glycol di-methane sulfonic acid ester (XVIIa) and 17.2 g. of di-(fl-cyanoethoxyethyl)-N- methylamine (VIa) are thoroughly mixed, heated in an Oll bath for 45 hours at C. and thereafter further processed as described in Example XVIIc. 21 g. (74 percent of the theory) of a yellowish brown sirupy liquid are obtained.
  • COMPOUND XXI (a) y-Cyan0eth0xypr0pyl-N,N-Di(Cyanoethyl)-Amine 159 g. of acrylonitrile are added in portions with stirring at 45 C. to a solution of 75 g. of 3-aminopropanol- (1) and 10 g. of sodium hydroxide in 250 cc. of water. After stirring for 8 hours the mixture is shaken three times with 250 cc. of methylene chlorideeach. The collected extracts are washed 'with 50 cc. of water, dried 11 with sodium sulphate, filtrated and evaporated. The residue is fractionated in vacuo.
  • COMPOUND XXIII Di-(Ethoxy)-Ethyl ta,w-Bis-N,N'-[Hexa-(Cyanoethoxyethyl) ]-A mmonium-p-Toluene S ul fonale 61.6 g. of tri-(cyanoethoxyethyl)-amine (described in United States Patent No. 2,326,721) and 45.2 g. of triethylene glycol di-p-toluene sulfonic acid ester (XVIIIa) are heated for 5 hours to 120 C. and further processed according to Example XVIIc. 80 g. (75 percent of the theory) of a high viscous product are obtained.
  • COMPOUND XXV (a) Eth0xyethyl-a,w-Bis-[N,N,N',N-Tetra-Betyl-N,N'-Di (Cyanoethoxyethyl -Amm0nium-M ethane S ul fonate 45.2 g. of dibutyl-cyanoethoxyethyl amine (111a) and 26.2 g. of diethylene glycol di-methane sulfonic acid ester (XVIIa) are heated for 4-5 hours to 120 C. and further processed according to Example XVIIc. 50 g. (70 percent of the theory) of a yellowish brown sirupy liquid are obtained.
  • COMPOUND XXVII (a) Octaethylene Glycol Di-Metlmne Sulfonic Acid Ester 114 g. of methane sulpho-chloride are added in portions at 0 C. to a solution of g. of octa-ethyleneglycol in 200 ml. of dried pyridine, whereby the reaction temperature in the flask should not exceed 5 C. The mixture is stirred for 1 /2 hours at room temperature and thereafter poured onto 500 g. of ice. The resulting mixture is acidified with hydrogen chloride, saturated with common salt and extracted with methylene chloride. The organic product is separated, clarified with active carbon and bleaching earth and evaporated. The residue represents a yellowish brown viscous product which does not crystallize.
  • XXVIIa octaethylene glycol di-methane sulfonic acid ester
  • EXAMPLE 1 A negative gelatino-silver bromiodide emulsion with a silver coating of 4.5 g. of Ag/m. and an iodine content of 66 mmol/mol of Ag and also a content of 920 mg. of 4-hydroxy-6-methyl-l,3,3a,7-tetrazaindene is divided into two portions (A-l-B). Portion A is cast on a cellulose triacetate film; to portion B are added 0.6 g. of the oleyl polyether derived from 20 mols of ethylene oxide and 1 mol of oleyl alcohol. The resulting emulsion is also cast on a cellulose triacetate film.
  • the layers are exposed to light behind a stepped wedge with a logarithmic density increase of 0.15 and developed for 5 and 10 minutes, respectively, at 20 C. in a developer of the following composition:
  • the layers are thereafter fixed and rinsed.
  • the comparative compounds have the following chemical constitution:
  • COMPARATIVE COMPOUND 1 DIME-THYL-PHEN- ETHYL-fi-HYDROXYETHYL-AMMONIU M CHLORIDE -8.5 g. of N,N-dimethylaminoethanol and 14 g. of wchlorethyl benzene are heated for 2 hours to C.
  • reaction product is recrystallized from acetone/alcohol Melting point: 9293 C. Yield: 16 g.
  • COMPARATIVE COMPOUND 2.DIETHYL-BENZYL-B- HYDROXYETHYL-AMMONIUM CHLORIDE 17.8 g. of N,N-dirnethyl-aminoethanol and 24.4 g. of 1,6-dibromohexane are heated for 2 hours to 100 C. The reaction product is recrystallized from alcohol.
  • EXAMPLE 2 An orthochromatically sensitized miniature film strip (Agfa Agepe) exposed behind a stepped'wedge is developed'for 3 minutes at 20 C. in a developer having the following composition:
  • the strip is thereafter fixed and rinsed.
  • EXAMPLE 3 A panchromatically sensitized minature film strip (Agfa Isopan IFF exposed behind a stepped wedge is developed for 3 minutes at 20 C. in a developer having the following composition a I Anhydrous Na SO 50 Hydroquinone 1 6.5 Anhydrous N21 CO I 40 NaBr 5 1-phenyl-3-pyrazolidone Q 0.3 Water to make 1000 cc.
  • the strip is then fixed and rinsed.
  • a highly sensitive film (Agfa X-ray dental film) coated on both sides and disposed beneath an aluminium step, is exposed with X-ray radiation and developed for 3 minutes at 20 C. in the developer referred to in Example 2.
  • the same film is developed in a developer which also contains 0.25 g. of the sub-
  • An orthochromatically sensitized miniature film strip (Agfa Agepe) exposed behind a stepped wedge is developed for 3 minutes at 20 C. in a developer having the following composition:
  • the strip is then fixed and rinsed.
  • EXAMPLE 6 A highly sensitive film (Agfa X-ray dental film) coated on both sides and disposed beneath an aluminum step is exposed to X-ray radiation and fixed and developed for 7 minutes at 20 C. with vigorous movement in a combined fixer and developer of the following composition:
  • the same film is developed in a combined fixer and developer which also contains 0.5 g. of the substance II per litre.
  • EXAMPLE 8 A panc-hromatically sensitized miniature film strip (Agfa Isopan IFF) exposed behind a stepped wedge is fixed and developed for 7 minutes at 20 C. with vigorous movement in a combined fixer and developer of the following composition:
  • the same film is developed in a combined fixer and developer which also contains 0.25 or 0.5 g. of the substance II per litre.
  • EXAMPLE 9 A highly sensitive film (AGFA X-ray dental film) coated on both sides and disposed beneath an aluminium step is exposed with X-ray radiation and fixed and developed for 7 minutes at 20 C. with vigorous movement aforementioned combined fixer and developer, which also contains the substances I, VII or Addition, Sensi- Speeirnen g./l. Fogging tiv1ty, 'y 2 degrees 1 2 As in Example 2.
  • EXAMPLE 7 An orthochromatically sensitized miniature film strip 17 in a combined fixer and developer having the following composition:
  • a color positive film strip (Agfa Color Positive Cinefilm Type S) exposed behind a stepped wedge is developed for 8 minutes at C. in a color developer of the following composition:
  • EXAMPLE 11 A silver bromide paper (Agfa Brovira Normal 1) exposed behind a stepped wedge with a logarithmic density increase of 0.1 is developed for 60 seconds at 20 C. in a developer of the following composition and fixed and rinsed in the usual manner.
  • the same paper strip is developed in a developer which also contains 0.2 g. of the Compound XIII per litre.
  • the strip has the sensitivity and gradation of the comparison strip after 50 seconds; at 60 sec. it shows a sensitivity which is higher by one step.
  • EXAMPLE 12 A panchromatically sensitized gelatino-silver bromiodide negative emulsion, containing 0.35 mol of silver halide per litre of casting solution and having a sensitivity of 21 DIN was divided into two portions.
  • Portion A was cast as a comparison test with a casting thickness of 11,41. on a cellulose triacetate support, provided with a subbing layer.
  • Portion B had added thereto 1.5 g. of the Compound II per litre of casting solution and was cast with the same layer thickness.
  • EXAMPLE 13 A panchromatically sensitized photographic film (Agfa Isopan IFF) is exposed through a test wedge, developed for 10 minutes at 20 C., fixed and washed.
  • the developer has the following composition:
  • Samples of the same photographic material are processed under the same conditions with the only exception that the developer additionally contains a certain amount of the Compounds XVII-XX.
  • the improving of the sensitivity is indicated in degrees DIN; as measurement point is selected 3:0.2 over fogging.
  • the compound is prepared according to the following instructions: 52.7 g. of octaethylene glycol di-methane sulfonic acid ester (XXVIIb) and 40.4 g. of triethyl amine are refluxed for 5 hours in 50 cc. of acetone. After evaporating the solvent and the excess of triethylamine, the reaction mixture is extracted for three times with benzene, dissolved in methanol and treated with active carbon, bleaching earth and again with active carbon. After evaporating in vacuo 59 g. (81 percent of the theory) of a yellowish brown-colored highly viscous oil are obtained. A 20 percent aqueous solution is used for the photographic test.
  • EXAMPLE 19 A strip of a color-positive-film (Agfa-color-positive cinefilm type S) is exposed through a test wedge and developed for 8 minutes at 20 C. with a color-forming developer having the following composition:
  • EXAMPLE 20 A silver bromiodide gelatine emulsion having an iodide content of 60 mmol/mol Ag which contains a cyan coupler of the naphthol series for example Z-(N-methyl-N- n octadecyDamino sulfo 1 hydroxy 2 naphthanilide is divided in three portions.
  • Portion A is cast on a suitable support with a thickness of the layer of 5 1.
  • To portion B is added 0.5 g. of the Compound XX/kg. of emulsion.
  • To portion C is added 0.5 g. of the Compound XXVIII/kg. of emul- S1011.
  • the resulting layers of B and C have also a thickness of 5,u.
  • the three samples are exposed through a test wedge and developed under the same conditions for 8 minutes in the color-forming developer described in Example 19. After the usual further processing by means of a bleaching and fixing bath the following results are obtained:
  • a silver bromiodide gelatine emulsion with an iodine content of 40 mmol/mol Ag which contains a magenta coupler of the pyrazolobenzimidazole series for example 3' hepta decyl pyrazolobenzimidazole 5 sulfonic acid (as described in German Patent No. 1,070,030) is processed according to Example 20. It is developed for 14 minutes. The following results are obtained:
  • the development can be accomplished in the presence of silver halide solvents such as water-soluble alkali-metal, alkaline-earthmetal or ammonium thiosulfates, in particular sodium, potassium or ammonium thiosulfate.
  • silver halide solvents such as water-soluble alkali-metal, alkaline-earthmetal or ammonium thiosulfates, in particular sodium, potassium or ammonium thiosulfate.
  • the compounds according to the invention can be added to the developer composition in an amount of 0101-10 g. per litre or to a silver halide emulsion in an amountof 0.1-10 g. per kg. of emulsion.
  • R and R are each a radical of the group consisting of alkyl, phenylalkyl, phenyl, cyanoethyl, and cyanoethoxyethyl and together are the atoms required to complete a heterocyclic radical of the group consisting of morpholino and piperidino;
  • R is a member of the group consisting of alkyl, phenylalkyl, phenyl, cyanoethoxyethyl and radicals having the following formulae wherein m is an integer from 2 to 5, n is an integer from 2 to 6 and p is an integer from 1 to '100; and X is an anion.
  • R and R are each a radical of the group consisting of alkyl, phenylalkyl, phenyl, cyanoethyl, and cyanoethoxyethyl and together are the atoms required to complete a heterocyclic ring, wherein m is an integer from 2 to 5 and p is an integer from 1 to 7, and X is an anion.
  • a light-sensitive photographic material having at least one light-sensitive silver halide emulsion layer and containing between 0.1 and 10 grams per kilogram of the said emulsion of a compound of the following formula in which R and R are each a radical of the group consisting of alkyl, phenylalkyl, phenyl, cyanoethyl, and cyanoethoxyethyl and together are the atoms required to complete a heterocyclic radical of the group consisting of morpholino and piperidino; R is a member of the group consisting of alkyl, phenylalkyl, phenyl, cyanoethoxyethyl and radicals having the following formulae and in which R and R are each a radical of the group consisting of alkyl, phenylalkyl, phenyl, cyanocthyl, and cy- 24 anoethoxyethyl and together are the atoms required to complete a heterocyclic radical of the group

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
US179472A 1961-03-16 1962-03-13 Developing accelerators for silver halide emulsion layers Expired - Lifetime US3129100A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEA0036987 1961-03-16

Publications (1)

Publication Number Publication Date
US3129100A true US3129100A (en) 1964-04-14

Family

ID=6929967

Family Applications (1)

Application Number Title Priority Date Filing Date
US179472A Expired - Lifetime US3129100A (en) 1961-03-16 1962-03-13 Developing accelerators for silver halide emulsion layers

Country Status (4)

Country Link
US (1) US3129100A (enrdf_load_stackoverflow)
DE (1) DE1422811A1 (enrdf_load_stackoverflow)
FR (1) FR1317771A (enrdf_load_stackoverflow)
NL (1) NL276068A (enrdf_load_stackoverflow)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3189448A (en) * 1962-08-22 1965-06-15 Eastman Kodak Co Developing compositions used in photographic transfer processes
US3206308A (en) * 1959-12-28 1965-09-14 Eastman Kodak Co Photographic stratum transfer process and developing compositions therefor
US3502472A (en) * 1965-10-11 1970-03-24 Agfa Gevaert Nv Development accelerators for silver halide emulsion layers
US3532499A (en) * 1965-10-07 1970-10-06 Agfa Gevaert Nv Amino - n - oxides as development accelerators in photography

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2482546A (en) * 1948-07-09 1949-09-20 Gen Aniline & Film Corp Phenoxyalkylamines as accelerators for photographic developers
US2944902A (en) * 1956-07-30 1960-07-12 Eastman Kodak Co Sensitization of photographic emulsions with ionic polyalkylene oxide salts
US3047399A (en) * 1960-04-04 1962-07-31 Ray Brown Method and composition for producing meaty flavor in foods and food products

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2482546A (en) * 1948-07-09 1949-09-20 Gen Aniline & Film Corp Phenoxyalkylamines as accelerators for photographic developers
US2944902A (en) * 1956-07-30 1960-07-12 Eastman Kodak Co Sensitization of photographic emulsions with ionic polyalkylene oxide salts
US3047399A (en) * 1960-04-04 1962-07-31 Ray Brown Method and composition for producing meaty flavor in foods and food products

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3206308A (en) * 1959-12-28 1965-09-14 Eastman Kodak Co Photographic stratum transfer process and developing compositions therefor
US3189448A (en) * 1962-08-22 1965-06-15 Eastman Kodak Co Developing compositions used in photographic transfer processes
US3532499A (en) * 1965-10-07 1970-10-06 Agfa Gevaert Nv Amino - n - oxides as development accelerators in photography
US3502472A (en) * 1965-10-11 1970-03-24 Agfa Gevaert Nv Development accelerators for silver halide emulsion layers

Also Published As

Publication number Publication date
DE1422811A1 (de) 1968-10-24
NL276068A (enrdf_load_stackoverflow)
FR1317771A (enrdf_load_stackoverflow) 1963-05-08

Similar Documents

Publication Publication Date Title
US3021215A (en) Polythialkylenediols as sensitizers for photographic silver halide emulsions
US2944902A (en) Sensitization of photographic emulsions with ionic polyalkylene oxide salts
US2940855A (en) Sensitization of photographic emulsions
US3038805A (en) Non-polymeric open-chain sensitizers
US3247201A (en) 1-carbocyclic aryl-2-tertiary amino-3, 4-hydrocarbon and carbocyclic aryl-3-pyrazolidones
US3705035A (en) Diffusion-fast color-forming developing agents
US3563745A (en) Silver halide photographic materials containing 1-arylmethyl-2-pyrazolin-5-one color couplers
US3615505A (en) Silver halide emulsion containing 2-pyrazolin-5-one color coupler
US2981624A (en) Antifoggants and stabilizers for photographic silver halide emulsion
US2937089A (en) Supersensitized photographic emulsions containing sulfonated compounds
US3266897A (en) Antifoggant agents for photography
US3765901A (en) Spectral sensitization of light-sensitive silver halide emulsions
US3129100A (en) Developing accelerators for silver halide emulsion layers
JP2649692B2 (ja) ハロゲン化銀写真感光材料
US4634660A (en) Development-processing method for silver halide photographic light-sensitive material
US2944900A (en) Sensitization of photographic emulsions with ionic polyalkyene oxide salts
US2743181A (en) Stabilized photographic silver halide emulsions
US3778268A (en) Light-sensitive silver halide photographic material
US3844788A (en) Incorporation of sulfonyl derivatives of isothiourea in light-sensitive elements
JPH0322973B2 (enrdf_load_stackoverflow)
US3895951A (en) Silver halide emulsion supersensitized with a merocyanine dye and a tertiary phosphine sulfide
US3532499A (en) Amino - n - oxides as development accelerators in photography
US3026201A (en) Antifoggants and stabilizers for photographic silver halide emulsions
US3981857A (en) Gelatin hardening process
US2448939A (en) Thioglycolic amide couplers