US3379533A - Dyes derived from 1, 2-disubstituted-3, 5-pyrazolidinediones and photographic elements containing such dyes - Google Patents

Dyes derived from 1, 2-disubstituted-3, 5-pyrazolidinediones and photographic elements containing such dyes Download PDF

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US3379533A
US3379533A US286449A US28644963A US3379533A US 3379533 A US3379533 A US 3379533A US 286449 A US286449 A US 286449A US 28644963 A US28644963 A US 28644963A US 3379533 A US3379533 A US 3379533A
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series
mol
dyes
dye
nuclei
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Philip W Jenkins
Leslie G S Brooker
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Eastman Kodak Co
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Eastman Kodak Co
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Priority to DEE27158A priority patent/DE1237896B/de
Priority to FR977517A priority patent/FR1401588A/fr
Priority to BE649026A priority patent/BE649026A/xx
Priority to GB23979/64A priority patent/GB1075391A/en
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03C—PHOTOSENSITIVE MATERIALS FOR PHOTOGRAPHIC PURPOSES; PHOTOGRAPHIC PROCESSES, e.g. CINE, X-RAY, COLOUR, STEREO-PHOTOGRAPHIC PROCESSES; AUXILIARY PROCESSES IN PHOTOGRAPHY
    • G03C1/00—Photosensitive materials
    • G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
    • G03C1/825—Photosensitive materials characterised by the base or auxiliary layers characterised by antireflection means or visible-light filtering means, e.g. antihalation
    • G03C1/83—Organic dyestuffs therefor
    • G03C1/832—Methine or polymethine dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
    • C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
    • C09B23/06—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups three >CH- groups, e.g. carbocyanines
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
    • C09B23/08—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines
    • C09B23/083—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines five >CH- groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/10—The polymethine chain containing an even number of >CH- groups
    • C09B23/105—The polymethine chain containing an even number of >CH- groups two >CH- groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/10—The polymethine chain containing an even number of >CH- groups
    • C09B23/107—The polymethine chain containing an even number of >CH- groups four >CH- groups
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
    • C09B23/12—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain being branched "branched" means that the substituent on the polymethine chain forms a new conjugated system, e.g. most trinuclear cyanine dyes

Definitions

  • This invention is related to dyes for photography and more particularly to dyes derived from 1,2-disuhstituted- 3,5-pyrazolidinediones and their use as sensitizers for photographic silver halide emulsions and/or bleachable filter dyes for light absorbing layers in photographic elements.
  • cyanine dyes are useful for spectral sensitization of silver halide emulsions, that is, for extending the sensitivity of the silver halide to light of longer wavelengths.
  • Such light-filtering layers may be coated over the light-sensitive layer, between two difierently sensitized light-sensitive layers, between a light-sensitive layer and the support or on the side of the support opposite to the side bearing a light-sensitive layer.
  • Dyes useful for filter layers must not only absorb light of the desired wavelengths but must be readily bleachable and/ or removable during the normal photographic processing operations. New sensitizing and/or light-filtering dyes are desired for use in photographic elements.
  • a further object is to provide new cyanine, merocyanine, styryl and holopolar dyes derived from 1,2-disubstituted-3,5-pyrazolidinediones that are valuable for use in photographic elements.
  • Another object is to provide a synthesis for making our new dyes.
  • Another object is to provide photographic silver halide emulsions containing our new dyes.
  • Still another object is to provide photographic elements comprising a support, at least one hydrophilic colloid layer containing light-sensitive silver halide and at least one hydrophilic layer containing at least one of our dyes.
  • R and R each represents the same or a different group selected from the class consisting of alkyl groups, e.g., methyl, ethyl, phenethyl, propyl, butyl, hexyl, cyclohexyl, dodecyl, octadecyl, etc. and aryl groups, e.g., phenyl, 4-methylphenyl, 4-methoxyphenyl, etc.
  • alkyl groups e.g., methyl, ethyl, phenethyl, propyl, butyl, hexyl, cyclohexyl, dodecyl, octadecyl, etc.
  • aryl groups e.g., phenyl, 4-methylphenyl, 4-methoxyphenyl, etc.
  • R and R are as defined previously;
  • R represents an alkyl group, e.g., methyl, earbethoxymethyl, ethyl, carbethoxyethyl, carboxyethyl, propyl, butyl, 4-sulfobutyl, hexyl, dodecyl, octadecyl, etc.; or an aryl group, e.g., phenyl, 4-methylphenyl, etc.;
  • Our dyes are valuable for use in photographic elements. Certain of the dyes have sensitizing properties for silver halide emulsions while others are easily bleachable by photographic processing solutions and can therefore be used in the preparation of bleachable filter or antihalation layers. Some of our dyes are useful in filter layers coated over the light-sensitive layer(s) or between two or more light-sensitive layers which may be differently sensitized as in elements for color photography.
  • the dyes of our invention are produced to advantage by heating the l,2-disubstituted-3,S-pyrazolidinedione or its 4-substituted derivative with the appropriate intermediate in a suitable inert solvent, preferably in the presence of a basic condensing agent.
  • the condensation reactions are carried out to advantage by heating the reaction mixture to a temperature between room temperature and the reflux temperature.
  • any of the well known basic condensing agents are used, such as the trialkylamines, e.g., triethylamine, tri-Il- 4 propylamine, triisopropylamine, tri-n-butylamine, etc., the N,N-dialkylanilines, e.g., N,N-dimethylaniline, N,N-diethylaniline, etc., the N-alkylpiperidines, e.g., N-methylpiperidine, N-ethylpiperidine, etc.
  • the trialkylamines e.g., triethylamine, tri-Il- 4 propylamine, triisopropylamine, tri-n-butylamine, etc.
  • the N,N-dialkylanilines e.g., N,N-dimethylaniline, N,N-diethylaniline, etc.
  • the N-alkylpiperidines e.g., N-
  • Y represents a group, such as ethyl (to produce a simple merocyanine), fi-acetanilidovinyl or thioacetonylidene (to produce a merocarbocyanine), or 4-methoxybutadienyl, or 4-anilinovinyl-1,3-butadienyl (to produce a merodicarbocyanine dye), and X- represents any acid anion, e.g., chloride, bromide, methylsulfate, ethylsulfate, p-toluenesulfonate, perchlorate, etc.
  • the Y group can also be methyl when 4-(5-acetanilido-2,4-pentadienylidine)-l,2- substituted-3,S-pyrazolidinedione isused in the condensation reaction.
  • the oxonols of Formula III are prepared to advantage by condensing the appropriate compound of Formula I with diethoxymethyl acetate (to give a monomethinoxonol), trimethoxypropene (to give 'a trimethinoxonol) and 1-anilino-5-phenylimino-1,3-pentadiene hydrochloride (to give a pentamethinoxonol).
  • R p, q, W, W and X ' are as defined previously and R represents an alkyl group or an aryl group.
  • the styryl dyes of Formula V are prepared to advantage by condensing a compound of Formula I with an intermediate such as p-dimethyl'aminobenzaldehyde or p-dimethylaminocinnamaldehyde. No basic condensing agent is needed for these reactions.
  • Dye 5,-4 (3-ethyl-2-benzothiazolinylidene ethylidene] 1,2-diphenyl-3 ,5 -pyrazolidinedione 1,2-diphenyl-3,5-pyrazolidinedione (1 mol., 1.25 g.), 2- fl-acetanilidovinyl-3-ethylbenzothiazolium iodide (1 mol.,
  • Dye 1 1.-4- [4- 3-ethyl-2-b enzoxazolinylidcne -2-butenylidene]-1,2-dimethyl'3 ,5 -pyrazolidinedione l,2-dimethyl-3,S-pyrazolidinedione (1 mol., 0.45 g.), 2-(4-rnethoxybutadienyl)-3-ethylbenzoxazolium iodide (1 mol., 1.15 g.), and triethylarnine (1 mol., 0.35 g.) were dissolved in ethanol (10 ml.), and the solution was heated under reflux for twenty minutes. The reaction mixture was cooled and diluted with water (200 ml.).
  • the dye suspension was chilled overnight, and the crude product was collected by filtration and dried.
  • the desired dye was extracted from the crude product with boiling benzene (125 ml.).
  • the dye was precipitated from the benzene solulion by the addition of ligroin ml., B.P. 100ll5 C.) and, after chilling, was isolated by filtration. After one recrystallization from benzene and ligroin (B.P. 100- C.), the yield of pure dye was 0.2 g. (18%), M.P. 222.5-224.5 C. dec.
  • the reaction mixture was cooled and diluted with water ml.).
  • the dye suspension was chilled overnight, and the crude product was collected by filtration. This damp product was boiled with 50 ml. of methanol. After chilling the mixture overnight, the methanol was decanted and the residual gum dissolved in pyridine. This solution was filtered and diluted with methanol. The solution was chilled, and the crude dye was isolated by filtration and dried. After two recrystallizations from pyridine and methanol, the yield of pure dye was 0.65 g. (14%), M.P. 225.5-227.5 C. dec.
  • the reaction mixture was cooled and diluted with ether (250 ml.). After chilling the mixture overnight, the ether was decanted and the residue was boiled with methanol (50 ml.). The mixture was chilled, and the crude product was isolated by filtration, washed with methanol, and dried. After two recrystallizations from pyridine and methanol the yield of pure dye was 1.1 g. (31% MP. 290.5292.0 C. dec.
  • Dye 20 -Bis-( 1,2-diphenyl-4-pyrazo1idine-3,5 -dione trimethineoxonol triethylammonium salt 1,2-diphenyl-3,S-pyrazolidinedione (1 mol., 5.05 g.), trimethoxypropene (1 mol., 1.35 g.), and triethylamine (1 mol., 2.0 g.) were dissolved in ethanol (25 ml.), and the solution was heated under reflux for fifteen minutes. The reaction mixture was chilled overnight, and the crude product was isolated by filtration and dried. After two recrystallizations from methanol, the yield of pure dye was 0.9 g. (14%), M.P. 2335-2350 C. dec.
  • the reaction mixture was chilled overnight, and the crude product was isolated by filtration, washed with ether, and dried.
  • the crude dye weighed 11.8 g. (65%) and was employed without further purification as an intermediate in the preparation of additional dyes.
  • Two recrystallizations of a sample of the crude dye (2.0 g.) from glacial acetic acid containing acetic anhydride gave 1.5 g. (75% recovery), M.P. 241.0242.0 C.
  • the 1,2-disubstituted-3,5-pyrazolidinediones were prepared by conventional methods well known in the art.
  • the new dyes of the invention are advantageously incorporated in the finished silver halide emulsion and should, of course, be uniformly distributed throughout the emulsion.
  • the methods of incorporating dyes in emulsions are r latively simple and well known to those skilled in the art of emulsion making. For example, it is convenient to add the dyes from solutions in appropriate solvents, in which the solvent selected should have no deleterious effect on the ultimate light-sensitive materials. Methanol, isopropanol, pyridine, etc. alone or in combination have proven satisfactory as solvents for the majority of our new dyes.
  • the type of silver halide emulsions that are sensitized with our dyes include any of those prepared with hydrophilic colloids that are known to be satisfactory for dis persing light-sensitive silver halides, for example, emulsions prepared with hydrophilic colloids, such as natural materials, e.g., gelatin, albumin, agar-agar, gu'm arabic, alginic acid, etc., and synthetic hydrophilic resins, e.g., polyvinyl alcohol, polyvinyl pyrolidone, cellulose ethers, partially hydrolyzed cellulose acetate, etc.
  • hydrophilic colloids such as natural materials, e.g., gelatin, albumin, agar-agar, gu'm arabic, alginic acid, etc.
  • synthetic hydrophilic resins e.g., polyvinyl alcohol, polyvinyl pyrolidone, cellulose ethers, partially hydrolyzed cellulose acetate, etc.
  • concentration of our new dyes in the emulsion can vary widely, -i.e., from about 5 to about 100 mgs. per liter of fiowable emulsion.
  • concentration will vary according to the type of light-sensitive material in the emulsion and according to the effects desired.
  • the most advantageous dye concentration for any given emulsion can be readily determined by making the tests and observations customarily used in the art of emulsion making.
  • our dyes can be incorporated by other methods in many of the emulsions customarily used in the art.
  • the dyes can be incorporated by bathing a plate or film bearing an emulsion, in a solution of the dye.
  • Photographic silver halide emulsions such as those listed above, containing the sensitizing dyes of our invention can also contain such addenda as chemical sensiiizers, e.g., sulfur sensitizers (e.g., allyl thiocarbamide, thiourea, allylisothiocyanate, cystinc, etc.), various gold compounds (e.g., potassium chloroaurate, auric trichloride, etc.) (see U.S. patents to W. D. Baldsiefen, 2,540,- 085, granted Feb. '6, 1951; R. E. Damschroder, 2,597,- 856, granted May 27, 1952; and H. C.
  • chemical sensiiizers e.g., sulfur sensitizers (e.g., allyl thiocarbamide, thiourea, allylisothiocyanate, cystinc, etc.), various gold compounds (e.g., potassium chloroaurate, auric
  • our emulsions are coated to advantage on any of the materials used for photographic elements including, for example, paper, glass, cellulose acetate, cellulose nitrate, synthetic film-forming resins, etc.
  • Example 1 The representative dyes of our invention were each added, in sensitizing amounts ranging from about 20 mg. to about 170 mg. per mole of silver halide, to individual portions of a gelatino-silver bromoiodide emulsion containing 0.77 mole percent of silver iodide or a silver chlorobromide emulsion containing 40 mole percent of silver bromide (both of which are described by Trivelli and Smith, Photographic Science, vol. 79, 330 (1939)). After digesting for 10 minutes at C., the emulsions were coated on a cellulose acetate support and dried. A sample of each coating was exposed on an IB sensitometer and to a wedge spectrogram. The exposed coatings were photographically developed for three minutes in a conventional developer solution, fixed with a conventional fixing bath, washed and dried. The sensitizing ranges and sensitizing maxima determined from the processed images are recorded with the dye and type of emulsion.
  • dyes ll, 13, l7, 18, 19, 20 and 21 are bleached by photographic developer solutions and are therefore useful as dyes for light-filtering layers in photographic elements.
  • Certain dyes of our invention derived from 1,2-disubstituted-3,S-pyrazolidinediones are valuable spectral sensitizers for photographic silver halide emulsions and photographic elements coated therefrom.
  • the preferred sensitizers include the merocyanines, holopolar dyes, and oxonols.
  • Other dyes of our invention are bleachable by photographic developers and find use as filter dyes in photographic elements.
  • R and R each represent a group selected from the class consisting of an alkyl group and an aryl group;
  • R represents a group selected from the class consisting of an alkyl group and an aryl group;
  • L and L each represent a methine group;
  • r represents an integer of from 1 to 3;
  • W and W each represent the nonmetallic atoms required to complete a 5 to 6 membered heterocyclic nucleus selected from nuclei of the class consisting of nuclei of the thiazole series, nuclei of the benzothiazole series, nuclei of the naphthothiazole series, nuclei of the thionaphtheno-T,6',4,5-thiazole series, nuclei of the oxazole series, nuclei of the benzoxazole series, nuclei of the naphthoxazole series, nuclei of the selenazole series, nuclei of the benzoselenazole series, nuclei of
  • R represent alkyl groups and m represents an integer from 1 to 2.
  • a light-sensitive photographic emulsion comprising a hydrophilic colloid, silver halide and a dye selected from those having the formulas:
  • R and R each represents a group selected from the class consisting of an alkyl group and an aryl group; R represents a group selected from the class consisting of an alkyl group and an aryl group; L and L each represent a methine group; r represents an integer of from 1 to 3; and W and W each represent the nonmetallic atoms required to complete a 5 to 6 membered heterocyclic nucleus selected from nuclei of the class consisting of nuclei of the thiazole series, nuclei of the benzothiazole series, nuclei of the naphthothiazole series, nuclei of the thionaphtheno-7',6',4,5-thiazole series, nuclei of the oxazole series, nuclei of the benzoxazole series, nuclei of the naphthoxazole series, nuclei of the selenazole series, nuclei of the benzoselenazole series, nuclei of the naphthosel
  • a photographic element comprising a support, at least one hydrophilic colloid layer containing light-sensitive silver halide and at least one hydrophilic colloid layer containing a dye selected from those having the formulas:
  • R and R each represents a group selected from the class consisting of an alkyl group and an aryl group; R represents a group selected from the class consisting of an alkyl group and an aryl group; L and L each represent a methine group; 2' represents an integer of from 1 to 3; and W and W each represent the nonmetallic atoms required to complete a 5 and 6 rnernbered heterocyclic nucleus selected from nuclei of the class consisting of nuclei of the thiazole series, nuclei of the benzothiazole series, nuclei of the naphthothiazole series, nuclei of the thionaphtheno-7',6',4,S-thiazole series, nuclei of the oxazole sen'es, nuclei of the benzoxazole series, nuclei of the naphthoxazole series, nuclei of the selenazole series, nuclei of the benzoselenazole series, nucle
  • a light-sensitive photographic emulsion comprising a hydrophilic colloid, silver halide, and the dye bis- (1,2-diphenyl 4 pyrazolidine-3,5-dione)pentamethineoxonol.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
US286449A 1963-06-10 1963-06-10 Dyes derived from 1, 2-disubstituted-3, 5-pyrazolidinediones and photographic elements containing such dyes Expired - Lifetime US3379533A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
US286449A US3379533A (en) 1963-06-10 1963-06-10 Dyes derived from 1, 2-disubstituted-3, 5-pyrazolidinediones and photographic elements containing such dyes
DEE27158A DE1237896B (de) 1963-06-10 1964-06-04 Photographisches Aufzeichnungsmaterial
FR977517A FR1401588A (fr) 1963-06-10 1964-06-09 Nouveaux colorants utilisables dans les produits photographiques
BE649026A BE649026A (de) 1963-06-10 1964-06-09
GB23979/64A GB1075391A (en) 1963-06-10 1964-06-10 Dyes, processes for preparing them and photographic emulsions and photographic light absorbing layers containing them

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US286449A US3379533A (en) 1963-06-10 1963-06-10 Dyes derived from 1, 2-disubstituted-3, 5-pyrazolidinediones and photographic elements containing such dyes

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BE (1) BE649026A (de)
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GB (1) GB1075391A (de)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3440053A (en) * 1966-12-22 1969-04-22 Eastman Kodak Co Silver halide photographic emulsions containing allopolar cyanine dyes
US3687946A (en) * 1968-05-13 1972-08-29 Gaf Corp Novel tetranuclear methine dyes, processes for preparing the same, and electrophotographic systems and silver halide emulsions containing the same
WO1986004694A1 (fr) 1985-02-06 1986-08-14 Fuji Photo Film Co., Ltd. Materiau photographique photosensible a l'halogenure d'argent
JPH01183652A (ja) * 1988-01-18 1989-07-21 Fuji Photo Film Co Ltd ハロゲン化銀写真感光材料
US5091295A (en) * 1989-09-20 1992-02-25 Fuji Photo Film Co., Ltd. Color photographic material and method of forming color image
US6210447B1 (en) * 1996-03-22 2001-04-03 L'oreal Compositions containing pyrazolin-3,5-dione couplers for use in keratin fiber dyeing methods and kits
US6399290B1 (en) * 1992-01-13 2002-06-04 Eastman Kodak Company Silver halide imaging materials
WO2009123154A1 (ja) * 2008-03-31 2009-10-08 富士フイルム株式会社 紫外線吸収材料

Citations (8)

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Publication number Priority date Publication date Assignee Title
US2272163A (en) * 1942-02-03 Office-
US2427911A (en) * 1944-05-12 1947-09-23 Ilford Ltd 3, 5-diketo pyrazolidine color formers
US2639282A (en) * 1949-09-29 1953-05-19 Eastman Kodak Co Resin-dyes of the cyanine type
GB781551A (en) * 1955-01-10 1957-08-21 Bayer Ag N-carboxy-3,5-pyrazolidine-dione derivatives
US2895955A (en) * 1957-06-05 1959-07-21 Eastman Kodak Co Tricarbocyanine infrared absorbing dyes
US2955939A (en) * 1956-09-13 1960-10-11 Eastman Kodak Co Holopolar cyanine dyes and photographic emulsions containing them
US2965486A (en) * 1958-06-02 1960-12-20 Eastman Kodak Co Polymethine sensitizing dyes and photographic emulsions
US2984664A (en) * 1958-05-14 1961-05-16 Ilford Ltd Process for preparation of pentamethincyanines

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2272163A (en) * 1942-02-03 Office-
US2427911A (en) * 1944-05-12 1947-09-23 Ilford Ltd 3, 5-diketo pyrazolidine color formers
US2639282A (en) * 1949-09-29 1953-05-19 Eastman Kodak Co Resin-dyes of the cyanine type
GB781551A (en) * 1955-01-10 1957-08-21 Bayer Ag N-carboxy-3,5-pyrazolidine-dione derivatives
US2955939A (en) * 1956-09-13 1960-10-11 Eastman Kodak Co Holopolar cyanine dyes and photographic emulsions containing them
US2895955A (en) * 1957-06-05 1959-07-21 Eastman Kodak Co Tricarbocyanine infrared absorbing dyes
US2984664A (en) * 1958-05-14 1961-05-16 Ilford Ltd Process for preparation of pentamethincyanines
US2965486A (en) * 1958-06-02 1960-12-20 Eastman Kodak Co Polymethine sensitizing dyes and photographic emulsions

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3440053A (en) * 1966-12-22 1969-04-22 Eastman Kodak Co Silver halide photographic emulsions containing allopolar cyanine dyes
US3687946A (en) * 1968-05-13 1972-08-29 Gaf Corp Novel tetranuclear methine dyes, processes for preparing the same, and electrophotographic systems and silver halide emulsions containing the same
WO1986004694A1 (fr) 1985-02-06 1986-08-14 Fuji Photo Film Co., Ltd. Materiau photographique photosensible a l'halogenure d'argent
JPH01183652A (ja) * 1988-01-18 1989-07-21 Fuji Photo Film Co Ltd ハロゲン化銀写真感光材料
JPH0693092B2 (ja) 1988-01-18 1994-11-16 富士写真フイルム株式会社 ハロゲン化銀写真感光材料
US5091295A (en) * 1989-09-20 1992-02-25 Fuji Photo Film Co., Ltd. Color photographic material and method of forming color image
US6399290B1 (en) * 1992-01-13 2002-06-04 Eastman Kodak Company Silver halide imaging materials
US6210447B1 (en) * 1996-03-22 2001-04-03 L'oreal Compositions containing pyrazolin-3,5-dione couplers for use in keratin fiber dyeing methods and kits
US6551360B2 (en) * 1996-03-22 2003-04-22 Laurent Vidal Pyrazoline-3,5-dione-containing compositions for dyeing keratin fibres; their use in dyeing as couplers; dyeing process
WO2009123154A1 (ja) * 2008-03-31 2009-10-08 富士フイルム株式会社 紫外線吸収材料

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BE649026A (de) 1964-10-01
GB1075391A (en) 1967-07-12
DE1237896B (de) 1967-03-30

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