US2852385A - Supersensitization of photographic emulsions - Google Patents

Supersensitization of photographic emulsions Download PDF

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US2852385A
US2852385A US584553A US58455356A US2852385A US 2852385 A US2852385 A US 2852385A US 584553 A US584553 A US 584553A US 58455356 A US58455356 A US 58455356A US 2852385 A US2852385 A US 2852385A
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series
quinoline
emulsion
dye
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Jean E Jones
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Eastman Kodak Co
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Eastman Kodak Co
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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
    • G03C1/08—Sensitivity-increasing substances
    • G03C1/28—Sensitivity-increasing substances together with supersensitising substances
    • G03C1/29—Sensitivity-increasing substances together with supersensitising substances the supersensitising mixture being solely composed of dyes ; Combination of dyes, even if the supersensitising effect is not explicitly disclosed

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  • This invention relates to photographic silver halide emulsions useful in color photography and photographic silver halide emulsions containing dicarbocyanine dyes, and as supersensitizers therefor, styryl-type bases.
  • the sensitization produced by a given dye varies somewhat with the type of emulsion in which the dye is incorporated.
  • the sensitization of a given emulsion by a given dye may be altered by varying the conditions in the emulsion. For example, the sensitization may be increased by increasing the silver ion concentration or decreasing the hydrogen ion concentration (i. e., increasing the alkalinity) or both.
  • sensitization can be increased by bathingv plates, coated with a spectrally sensitized emulsion, in water or in aqueous solutions of ammonia.
  • Such a process of altering the sensitivity of a sensitized emulsion by increasing the silver ion concentration and/ or by decreasing the hydrogen ion concentration is commonly called hypersensitization.
  • Hypersensitized emulsions have generally poor keeping qualities.
  • R and R each represents an alkyl-group (such as methyl, ethyl, B-hydroxyethyl, carboxymethyl, S-carboxyethyl, carbomethoxymethyl, carbethoxymethyl, etc., n
  • X represents an acid radical, such as chloride, iodide, bromide, perchlorate, p-toluenesulfonate, benzenesulfonate, ethylsulfate, methylsulfate, etc.
  • Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus conmethylbenzothiazole, S-methylbenzothiazole, 6-methylbenzothiazole, S-bromobenzothiazole, d-bromobenzothia- Patented Sept. 16, 1958 thoselenazole series (e.
  • a-naphthoselenazole, B-naphthoselenazole, etc. a heterocyclic nucleus of the benzoxazole series (e. g., benzoxazole, S-hydroxybenzoxazole, 6- hydroxybenzoxazole, S-chlorobenzoxazole, S-methoxybenzoxazole, 6-methoxybenzoxazole, 5- phenylbenzoxazole, 5- bromobenzoxazole, etc.), a heterocyclic nucleus of the naphthoxazole series (e.
  • a-naphthoxazole, /3-naph thoxazole, etc. a heterocyclic nucleus of the Z-quinoline series (e. g., Z-quinoline, 6-methyl-2-quinoline, 7-methyl- 2-quinoline, S-methyl-Z-quinoline, 6-chloro-2-quinoline, 8-chloro-2-quinoline, 4-chloro-2-quinoline, 5-ethoxy-2- quinoline, 6-ethoxy-2-quinoline, 7-ethoxy-2-quinoline, 6- hydroxy-Z-quinoline, 7-hydroxy-2-quinoline, 6-methoxy-2- quinoline, etc.), .a heterocyclic nucleus of the 4-quinoline series (e.
  • benzimidazole series e.g., benzimidazole, S-chlorobenzimidazole, 5,6-di-chlorobenzimidazole, 1,7- trimethylenebenizimidazole, etc.
  • a heterocyclic nucleus of the 5,6-benz0quinoline series e. g., 5,6-benzo-2-quinoline, etc.
  • Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus selected from the group consisting of those of the benzoxazole series (e.
  • styryl-type'bases useful in practicing my invention can advantageously be represented by the following general formulas:
  • R represents a monocyclic aryl group of the benzene series, such as phenyl, dimethylaminophenyl (o-, m-, or -p), diethylaminophenyl (0 m-, or p-), aminophenyl (o-, m-, or p-), hydroxyphenyl (0-, m-, or p-), chlorophenyl (o-, m-, or -p-), etc.
  • 11 represents a positive integer of from 1 to 2
  • L represents a nitrogen atom or a methine group, i.
  • R is a hydrogen atom, a cyano group, an alkoxyl group (methoxyl, ethoxyl, etc., for example), etc.
  • Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus, such as those of the thiazole series, those of the benzothiazole series, those of the naphthothiazole series, those of the oxazole series, those of the benzoxazole series, those of the naphthoxazole series, those of the selenazole series,-those of the benzoselenazole series, those of the naphthoselenazole series, those of the perinaphtho- 1,3-thiazine series, those of the Z-quinoline series (It is 1),
  • these styryl-type bases can be prepared by condensing a heterocyclic base containing a reactive amino or methyl group with an aromatic aldehyde.
  • they can be prepared by dequaternization of the corresponding styryl dyes, as described in U. S. Patent 2,169,434, issued August 15, 1939.
  • Listed below are representative styryl-type bases of Formulas II or III which can advantageously be employed in my invention.
  • 2-p-dimethylaminostyryl-a-n aphthothiazole COH C HOHa 2-styrylbenzimidazole
  • I incorporate one or more of the dicarbocyanine dyes represented by Formula I represented by Formulas II or III above.
  • My invention is particularly directed to the ordinarily employed gelatino-silver-halide emulsions.
  • my super.- sensitizing combinations can be employed in silver halide emulsions in which the carrier is other than gelatin, e. 'g., a resinous substance or cellulosic material which has no deteriorating efiect on the light-sensitive materials.
  • the dicarbocyanine dyes and styryl-type bases can be em ployed in various concentrations depending upon the effects desired.
  • the optimum or near optimum concentration of the dicarbocyanine dyes which I employ in practicing my invention isof the order of from 0.616 to 0.30 g. per mol. of silver halide in the emulsion.
  • the styryI-type bases which I employ in my invention can advantageously be employed at a concentration of from about 0.010 to'1.0 g. per mol. of silver halide in the emulsion.
  • the ratio of concentration of dicarbocyanine dye to styryl-type base can vary rather widely in my combination, e. g. from 1:1 to 1:100 (by weight) inmany cases.
  • sensitizing dyes and styryl-type bases in silver halide emulsions are well known to those skilled in the art. While the dicarbocyanine dyes and styryl-type bases can be directly dispersed in the emulsions, it is convenient to add the same in the form of solutions in appropriate solvents. Methanol, ethanol, pyridine, and the like have proven satisfactory for many of the dyes of Formula I and bases of Formulas Hand III. Mixtures ofsolvents, e. g., pyridine diluted with methanol or acetone, can also be used.
  • solvents e. g., pyridine diluted with methanol or acetone
  • the dicarbocyanine dyes and styryl-type bases are dispersed in the finished emulsions and should be uniformly distributed throughout the emulsions.
  • the following procedure is N-methyl-p-aminophenol sulfate g 2.0 Hydroquinone e g 8.0 Sodium sulfite (desiccated) g 90.0 Sodium carbonate (monohydrate) g 52.5 Potassium bromide g. 5.0 Water to make liter 1
  • the speed (red), gamma and fog for each of the coatings was then measured. The results are recorded in Table I.
  • Stock solutions of the dicarbocyanine dyes and styryl-type bases are prepared by dissolving the same in appropriate solvents as described above. Then, to the flowable gelatino-silver-halide emulsion, the desired amounts of the stock solution of one of the dyes (or styryl-type bases) are slowly added, while stirring the emulsion. Stirring is continued until the dye is thoroughly incorporated in the emulsion. Then the desired amount 0t the stock solution of the styryl-type base (or dye, if
  • styryl-type base has been added first) is slowly added to the emulsion, while stirring. Stirring is continued until the second solution is thoroughly incorporated.
  • the supersensitized emulsion can then be coatedout on a suitable support, such as glass, cellulose derivative film, resin film, or paper, to a suitable thickness and allowed to dry.
  • a suitable support such as glass, cellulose derivative film, resin film, or paper.
  • the details of such coating methods are well known to those skilled in the art.
  • the foregoing procedures and proportions are to be regarded only as illustrative.
  • my invention is directed to any silver halide emulsion containing a combination of the aforesaid di-carbocyanine dyes and styryl-type bases whereby a supersensitizing effect is obtained.
  • My invention is primarily directed tothe ordinarily employed gelatino-silver-halide developing-out emulsions, e. g., gelatino-silver-chloride, -chlorobromide, -chloroio dide, '-chlorobromiodide, -bromide and -bromiodide de-' veloping-out emulsions.
  • Emulsions which form the latent image mostly inside the silver halide grains such as the emulsions set forth in U. S. Patent 2,456,956, dated December 21, 1948, can also be employed in practicing my invention.
  • the emulsions prepared in accordance with my inven- 7 auric trichloride, etc.) See U. S. Patents 2,540,085; 2,597,856 and 2,597,915), various palladium compounds, such as palladium chloride (U. S. 2,540,086), potassium chloropalladate (U. S. 2,598,079), etc., or mixtures of such sensitizers; antifoggants, such as ammonium chloroplatinate (U. S. 2,566,245), ammonium chloroplatinite (U. S. 2,566,263), benzotriazole, nitrobenzimidazole, nitroindazole, benzidine, mercaptans, etc.
  • various palladium compounds such as palladium chloride (U. S. 2,540,086), potassium chloropalladate (U. S. 2,598,079), etc., or mixtures of such sensitizers
  • antifoggants such as ammonium chlor
  • Example A.2-p-diethylaminobenzalamirwbenzothiazole An intimate mixture of 1.5 g. (1. mol.) of 2-aminobenzothiazole and 1.8 g. 1. mol.) of p-diethylaminobenzaldehyde was heated, with stirring, in a test tube over a free flame for three minutes. The deep orange sticky mass was dissolved in 2 ml. of methyl alcohol, the solution was stirred with ml. of ether and the whole chilled for one hour in a freezing mixture of ice and acetone. The crystals were collected on a filter and washed with ether. The yield of dye was crude, 8% after four recrystallizations from ligroin (B. P. 6675 C.) and 3% after a further recrystallization from aqueous alcohol.
  • dicarbocyanine dyes of my invention these styryl dyes do not generally provide the consistent results illustrated in the above examples with respect to the styryl-type bases. It has been found, for example, that the styryl dye, 2-pdimethylaminostyrylbenzoxazole ethiodide, can be employed in supersensitizing combination with various dicarbocyanine dyes, such as dye a of Table I.
  • the accompanying drawing illustrates the supersensitizing effect obtained with three of my new combinations of dyes in gelatino-silver-bromiodide emulsions.
  • Each figure in the drawing is a digrammatic reproduction of three spectrograms.
  • the sensitivity of the emulsion containing only the dicarbocyanine dye of Formula I is represented by the solid curve
  • the sensitivity of the same emulsion containing only the styryl-type .base of Formula II or III is represented by the curve consisting of dotted lines
  • the sensitivity of the same emulsion containing both the dicarbocyanine dye of Formula I and the styryl-type base of Formula II or III is represented by the curve consisting of alternating long and short lines.
  • curve A represents the sensitivity of an ordinary gelatino-silver-brorniodide emulsion sensitized with 3,3'-diethyloxathiadicarbocyanine iodide
  • curve B represents the sensitivity of the same emulsion sensitized with 2-p-diethylaminobenzalaminobenzothiazole
  • curve C represents the sensitivity of the same emulsion sensitized I p-diethylaminostyrylbenzothiazole.
  • curve A represents the sensitvity of an ordinary gelatino-silver-bromiodide emulsion sensitized with 3,3'-diethyloxathiadicarbocyanine iodide
  • curve D repre sents the sensitivity of the same emulsion sensitized with 1 2-p-diethylaminostyrylbenzothiazole
  • curve E represents the sensitivity of the same emulsion sensitized with both 3,3'-diethyloxathiadicarbocyanine iodide and 2- Sensitometric measurements for emulsions sensitized in the manner shown in Fig. 2 are given in Example 8 of the above table.
  • curve a represents the sensitivity of an ordinary gelatino-sllver-bromiodide emulsion sensitized with 3,3-diethyloxathiadicarbocyanine iodide
  • curve F represents the sensitivity of the same emulsion sensitized with 2-[4-( pdimethylaminophenyl) LEI-butadienyl] benzothiazole
  • curve G represents the sensitivity of the same emulsion sensitized with 3,3-diethyloxathiadicarbocyanine iodide and 2-4-(p-dirnethylarninophenyl)-1,3- butadienyl] benzothiazole.
  • R and R each represents an alkyl group
  • n a positive integer of from 1 to 2
  • X represents an acid radical
  • Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus selected from the group consisting of those of the bcnzothiazole series, those of the naphthothiazo-le series, those of the benzoselenazole series, those of the benzoxazole series, those of the naphthoxazole series, those of the Z-quinoline series, those of the 4-quinoline series, and those of the benzimidazole series
  • Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus selected from the group consisting of those of the benzoxazole series, those of the naphthoxazole, those of the hemselenazole series, those of the naphthoselenazole series, those of the benzothiazole series, and those of the naphthothiazole series, and at least one heterocyclic
  • Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus selected from the group consisting of those of the thiazole series, those of the benzothiazole series, those of the naphthothiazole series, those of the benzoxazole series, those of the benzoselenazole series, those of the perinaphtho-1,3-thiazine series, those of the benzimidazole series, those of the 2- qninoline series, those of the 4-quinoline series, and those of the Z-pyridine series
  • L represents a member selected from the group consisting of a nitrogen atom and a methine group.
  • R represents an aryl group
  • n represents a positive integer of from 1 to 2.
  • R represents an aryl group
  • n represented by the following general formula:
  • R and R each represents an alkyl group containing from 1 to 2 carbon atoms, n represents a positive integer of from 1 to 2, X represents an acid radical, Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus selected from the group consisting of those of the benzothiazole series, those of the naphthothiazole series, those of the benzoselenazole series, those of the benzoxazole series, those of the naphthoxazole series, those of the Z-quinoline series, those of the 4-quinoline series, and those of the benzimidazole series, and Z represents the nonmetallic atoms necessary to complete a heterocyclic nucleus selected from the group consisting of those of the benzoxazole series, those of the naphthoxazole series, those of the benzoselenaz-ole series, those of the naphthoselenazole series, those of the benzothiazole series, and those of the naphthothiazole series
  • Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus selected from the group consisting of those of the thiazole series, those of the benzothiazole series, those of the naphthothiazole series, those of the benzoxazole series, those of the benzoselenazole series, those of the perinaphtho-1,3-thiazine series, those of the benzimidazole series, those of the Z-quin'oline series, those of the 4-quin'oline series, and those of the 2- pyridine series
  • L represents a member selected from the group consisting of a nitrogen atom and a methine group
  • R represents a monocyclic aryl group of the benzene series
  • n represents a positive integer of from 1 to 2.
  • a photographic gelatino-silver-halide developingout emulsion sensitized with a supersensitizing combine tion of at least one'dicarbocyanine dye selected from those represented by the following general formula:
  • R and R each represents an alkyl group containing from 1 to 2 carbon atoms
  • n represents a positive integer of from 1 to 2
  • X represents an acid radical
  • Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus selected from the group consisting of those of the benzothiazole series, those of the naphthothiazole series, those of the benzoselenazole series, those of the benzoxazole series, those of the naphthoxazole series, those of the Z-quinoline series, those of the 4-quinoline series, and those of the benzimidazole series
  • Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus selected from the group consisting of those of the benzoxazole series, those of the naphthoxazole series, those of the benzoselenazole series, those of the naphthoselenazole series, those of the benzothiazol series, and those of the naphth
  • a pyridine series L represents a member selected from the group consisting of anitrogen atom and a methine group, R represents a monocyclic aryl group of the benzene series, and n represents a positive integer of from 1 to 2.
  • R and R each represents an alkyl group containing from 1 to 2 carbon atoms
  • X represents an acid radical
  • Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus of the benzothiazole series
  • Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus of the benzoxazole series
  • at' least one heterocyclic base selected from those represented by the following general formula:
  • Z represents the non-metallic atoms necessary to complete aheterocyclic nucleus selected from-the group consisting of those of the thiazole series, those of the henzothiazole series, those of the naphthothiazole series, those of the 'benzoXazole-series, those of the benzoselenazole series, those of the perinaphtho-l,3-thiazine series, those of the benzimidazole series, those of the 2-quinoline series, and those of the 2-pyridine series, L represents a member selected from the group consisting of a nitrogen atom and a methinegroup, :and R represents a monocyclic aryl group of the benzene series.
  • R and R each represents an alkyl group containing from 1 to 2 carbon atoms
  • X represents an acid radical
  • Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus of the benzethiazole series, and at least one heterocyclic base selected from those represented by the following general formula:
  • Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus selected from the group consisting of those of the thiazole series, those of the benzothiazole series, those of the naphthothiazole series, those of the benzoxazole series, those of the henzoselenazole series, those of the perinaphtho-l,3-thiazine series, those of the benzimidazole series, those of the 2- quinoline series, and those of the 2-pyricline series
  • L represents a member selected from the group consisting of a nitrogen atom and a methine group
  • R represents a monocyclic aryl group of the benzene series.
  • EIl -RI X wherein Z, represents the non-metallic atoms necessary to complete a heterocyclic nucleus of the benzothiazole series, and R represents a monocyclic aryl group of the benzene series.
  • R and R each represents an alkyl group containing from 1 to 2 carbon atoms
  • X represents an acid radical
  • 2 represents the non-metallic atoms necessary to complete a heterocyclic nucleus of the benzoxazole series, and at least one heterocyclic base selected from those represented by the following general formula:
  • Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus selected from the group consisting of those of the thiazole series, those of the benzothiazole series, those of the naphthothiazole seires, those of the benzoxazole series, those of the benzoselenazole series, those of the perinaphtho-l,3-thiazine series, those of the benzimidazole series, those of the 2- 'quinoline series, and those of the Z-pyridine series, 1., represents a member selected from the group consisting of a nitrogen atom and a methine group, and R represents a monocyclic aryl group of the benzene series.
  • R and R each represents an alkyl group containing from 1 to 2 carbon atoms, X represents an acid radical, and Z represents the non-metallic atoms neces sary to complete a heterocyclic nucleus of the benzoxazole series, and at least one heterocyclic base selected from those represented by the following general formula;
  • Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus of the naphthothiazole series
  • R represents a monocyclic aryl group of the benzene series.
  • a photographic gelatino-silver-halide developingout emulsion sensitized with a supersensitizing coinbination of at least 0 ae dicarbocyanine dye selected from those represented by the following general formula:
  • R and R each represents an alkyl group containing from 1 to 2 carbon atoms
  • X represents an acid radical
  • Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus of the benzothiazole series
  • Z represents the non-metallic atoms necessary to complete a heterocyclic nucleus of the benzoxazole series

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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)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
US584553A 1956-05-14 1956-05-14 Supersensitization of photographic emulsions Expired - Lifetime US2852385A (en)

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BE557439D BE557439A (pt) 1956-05-14
US584553A US2852385A (en) 1956-05-14 1956-05-14 Supersensitization of photographic emulsions
GB15061/57A GB858062A (en) 1956-05-14 1957-05-13 Improvements in dye-sensitized photographic emulsions
FR1195614D FR1195614A (fr) 1956-05-14 1957-05-13 Nouvelle émulsion photographique sursensibilisée par des bases styryliques

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3847621A (en) * 1971-12-07 1974-11-12 Konishiroku Photo Ind Laser-sensitive silver halide photosensitive material
US5166046A (en) * 1990-01-24 1992-11-24 Konica Corporation Spectrally sensitized silver halide photographic material
US6156776A (en) * 1995-06-08 2000-12-05 Yu; Dingwei Tim Diaryl substituted thiazoles useful in the treatment of fungal infections
US6380187B2 (en) 1999-03-25 2002-04-30 Dingwei Tim Yu Class of thiomorpholino substituted thiazoles
CN106279062A (zh) * 2016-07-20 2017-01-04 南方医科大学 一种苯并噻唑2‑乙腈衍生物及其应用

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2075046A (en) * 1932-11-04 1937-03-30 Eastman Kodak Co Photographic emulsion containing supersensitized pinacyanol
US2313922A (en) * 1938-07-08 1943-03-16 Eastman Kodak Co Photographic emulsion
US2448858A (en) * 1945-11-23 1948-09-07 Eastman Kodak Co Optically supersensitized photographic silver halide emulsion
US2680686A (en) * 1949-02-01 1954-06-08 Gevaert Photo Producten Sensitized and supersensitized photographic emulsions

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2075046A (en) * 1932-11-04 1937-03-30 Eastman Kodak Co Photographic emulsion containing supersensitized pinacyanol
US2313922A (en) * 1938-07-08 1943-03-16 Eastman Kodak Co Photographic emulsion
US2448858A (en) * 1945-11-23 1948-09-07 Eastman Kodak Co Optically supersensitized photographic silver halide emulsion
US2680686A (en) * 1949-02-01 1954-06-08 Gevaert Photo Producten Sensitized and supersensitized photographic emulsions

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3847621A (en) * 1971-12-07 1974-11-12 Konishiroku Photo Ind Laser-sensitive silver halide photosensitive material
US5166046A (en) * 1990-01-24 1992-11-24 Konica Corporation Spectrally sensitized silver halide photographic material
US6156776A (en) * 1995-06-08 2000-12-05 Yu; Dingwei Tim Diaryl substituted thiazoles useful in the treatment of fungal infections
US6380187B2 (en) 1999-03-25 2002-04-30 Dingwei Tim Yu Class of thiomorpholino substituted thiazoles
CN106279062A (zh) * 2016-07-20 2017-01-04 南方医科大学 一种苯并噻唑2‑乙腈衍生物及其应用
CN106279062B (zh) * 2016-07-20 2018-06-05 南方医科大学 一种苯并噻唑2-乙腈衍生物及其应用

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GB858062A (en) 1961-01-04

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