US3639127A - Silver halide emulsions containing a dye derived from 4,6-diaryl substituted picolinium salts as desensitizer - Google Patents

Silver halide emulsions containing a dye derived from 4,6-diaryl substituted picolinium salts as desensitizer Download PDF

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US3639127A
US3639127A US57831A US3639127DA US3639127A US 3639127 A US3639127 A US 3639127A US 57831 A US57831 A US 57831A US 3639127D A US3639127D A US 3639127DA US 3639127 A US3639127 A US 3639127A
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silver halide
iodide
nucleus
dye
halide emulsion
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Leslie G S Brooker
Daniel S Daniel
Robert C Taber
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Eastman Kodak Co
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Eastman Kodak Co
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    • 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
    • C09B23/0091—Methine or polymethine dyes, e.g. cyanine dyes having only one heterocyclic ring at one end of the methine chain, e.g. hemicyamines, hemioxonol
    • 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
    • C09B23/08—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
    • C09B23/02—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
    • C09B23/086—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 more than 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
    • 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
    • C09B23/14—Styryl dyes
    • C09B23/145—Styryl dyes the ethylene chain carrying an heterocyclic residue, e.g. heterocycle-CH=CH-C6H5
    • 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
    • G03C1/10—Organic substances
    • G03C1/12—Methine and polymethine dyes
    • 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
    • G03C1/36—Desensitisers

Definitions

  • the dyes present in the photographic silver halide emulsions and photographic elements of our invention include those having the following general formulas:
  • R represents a phenyl nucleus (including substituted phenyl) such as phenyl, an alkylphenyl preferably containing from one to four carbon atoms in the alkyl portion such as pmethylphenyl, p-ethylphenyl, p-propylphenyl, pisopropylphenyl, p-butylphenyl, m-methylphenyl, ethylphenyl, etc., an alkoxyphenyl preferably containing from one to five carbon atoms in the alkoxy portion such as pmethoxyphenyl, p-ethoxyphenyl, p-propoxyphenyl, pisopropoxyphenyl, p-butoxyphenyl, p-pentyloxyphenyl, mm
  • B- carboxyethyl, y-carboxypropyl or w-carboxybutyl for example, an alkanoyloxyalkyl group such as B-acetoxyethyl, B- propionyloxyethyl, 'y-acetoxypropyl, w-acetoxybutyl or w-butyryloxybutyl, for example, an alkoxycarbonylalkyl group such as methoxycarbonylmethyl, B-methoxycarbonylethyl, B- ethoxycarbonylethyl, y-ethoxycarbonylpropyl or m-ethoxycarbonylbutyl, for example, an aralkyl group such as benzyl or phenethyl, for example, or an aryl group (including substituted aryl) such as phenyl, tolyl, chlorophenyl, sulfophenyl or carboxyphenyl, for example,
  • a 2-thio-2,4-oxazolidinedione nucleus i.e., a 2-thio-2,4( 3H,5H )oxazoledione nucleus
  • a 2-thio-2,4-oxazolidinedione nucleus i.e., a 2-thio-2,4( 3H,5H )oxazoledione nucleus
  • 3-ethyl-2-thio-2, 4-oxazolidinedione 3-(2-sulfoethyl)-2-thio-2,4-oxazolidinedione, 3-(4-sulfobutyl)-2-thio-2,4-oxazolidinedione, 3-(3-carboxypropyl)-2-thio-2,4 -oxazolidinedione, etc.
  • a thianaphthenone nucleus e.g., 3-(2H)-thianaphthenone, etc.
  • a 2-thio-2,5-thiazolidinedione nucleus i.e., a 2-thio-2,S(3 H,4H)-thiazoledione nucleus
  • a 2,4-thiazolidinedione nucleus e.g., 2,4-thiazolidinedione, 3-ethyl-2,4-thiazolidinedione, S-phenyl-2,4,-thiazolidinedione, 3-oz-naphthyl-2,4-thiazolidinedione, etc.
  • a thiazolidinone nucleus e.g., 4-thiazolidinone, 3-ethyl- 4-thiazolidinone, 3-phenyl-4-thiazolidinone, 3-a-naphthyl-4- thiazolidinone, etc.
  • a 2-thiazolin-4-one nucleus e.g., 4-thiazolidinone, 3-ethyl- 4-thiazolidinone
  • the above-defined dye compounds include both sensitizers and desensitizers for light-sensitive photographic silver-halide emulsions. Those that are sensitizers contain no desensitizing groups and are the preferred species, whereas those that are desensitizers always contain at least one strongly negative group such as a nitro or phenylazo substituent on a phenyl nucleus. All of the above compounds are crystalline and soluble in water and alcohol.
  • the dyes are produced by heating a mixture of a quaternary salt of above formulas V or V1 with the appropriate intermediate.
  • the reaction mixtures are heated to advantage in any suitable solvents used in dye synthesis including solvents such as ethanol, propanol, dioxane, pyridine, quinoline, and the like, at temperatures up to the reflux temperature of the mixture.
  • the reaction is carried out in the presence of a basic condensing agent such as a tertiary amine, e.g., trimethylamine, triethylamine, tri-npropylamine, tri-n-butylamine, N-methylpiperidine, N-ethylpiperidine, N,N-dimethylaniline, N,N-diethylaniline, etc.
  • a basic condensing agent such as a tertiary amine, e.g., trimethylamine, triethylamine, tri-npropylamine, tri-n-butylamine, N-methylpiperidine, N-ethylpiperidine, N,N-dimethylaniline, N,N-diethylaniline, etc.
  • the symmetrical cyanine dyes of formula I are prepared to advantage by heating a mixture of a compound of formula V with diethoxymethyl acetate (forms carbocyanine), trimethoxypropene (forms dicarbocyanine), l-anilino-S- phenylimino-l,3-pentadiene hydrochloride (forms tricarbocyanine), etc., preferably in a solvent and in the presence of a tertiary amine such as mentioned above.
  • G, 1R,,X and Z are as previously defined, g represents a positive integer of from one to two R represents an aryl group of from 67 carbon atoms, c.g., phenyl, p-tolyl, etc., and R represents an alkyl group of from 1-12 carbon atoms. This is preferably carried out in a suitable solvent and in the presence of a basic condensing agent.
  • the unsymmetrical cyanine dyes of formula ll wherein n is 2 are prepared in generally similar manner from a mixture of a compound of formula Vl with formula VII.
  • the styryl dyes of formula [II are prepared to advantage by heating a mixture of a compound of formula V or formula V] with the appropriate N,N-disubstituted p-aminobenzaldehyde, N,N-disubstituted p-aminocinnamaldehyde, m-nitrobenzaldehyde, etc., preferably in a suitable solvent and in the presence of a basic condensing agent.
  • EXAMPLE l-2METHYL4,6-DIPHENYLPYRYLIUM IODIDE CH B C1121 Sulfuric acid (30 ml.) was slowly added to acetic anhydride (100 ml.) and the mixture was heated at 70 C. for 2 hours. Acetophenone (30 ml.) and an additional portion of acetic anhydride (15 ml.) were then added and the mixture heated at 50 C. for 24 hours. To the cooled mixture ethanol (200 ml.) was added and the mixture was chilled for 3 hours. The product was collected on the filter and washed with ether.
  • the sulfoacetate was suspended in water (1,000 ml.) and converted to the iodide by stirring with sodium iodide (20 g.) at 60 C. for 1 hour. The product was collected on the filter and washed with water and then ethanol. The crude yield was 22 g. (53 percent). After one recrystallization from ethanol it melted at 220222 C. with decomposition.
  • the fluoborate was suspended in water (1,000 ml.) and converted to the iodide by stirring with sodium iodide (20 g.) at 60 for 1 hour.
  • the product was collected on a filter and washed with water and then alcohol.
  • the crude yield was 33.2 g. Recrystallized from ethanol it melted at 244246 C. with decomposition.
  • Table 9 Yield Melting Point Recrystallization
  • EXAMPLE 12 This example illustrates the increase in sensitivity produced in photographic silver halide emulsions by a number of the preferred dyes used in preparing the emulsions of the invention.
  • the dyes were tested in a silver bromoiodide emulsion containing 0.77 mole percent iodide of the type described by Trivelli and Smith, Phat. Journal, 79, 330 (1939).
  • the dyes, dissolved in suitable solvents, were added to separate portions of the emulsions at the concentrations indicated.
  • the emulsions were then coated at a coverage of 432 mg. silver/ft. on a cellulose acetate film support. A sample of each coating was exposed on an Eastman IB Sensitometer and to a wedge spectrograph, processed for 3 minutes in a developer of the following composition:
  • the dyes are advantageously incorporated in the washed, finished silver halide emulsion and should, of course, be uniformly distributed throughout the emulsion.
  • the methods of incorporating dyes in emulsions are relatively 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 case the solvent selected should be completely free from any deleterious effect on the ultimate light-sensitive materials. Methanol, isopropanol, pyridine, etc., alone or in admixtures, have proven satisfactory as solvents for the majority of the dyes.
  • the type of silver halide emulsions that can be sensitized with the dyes include any of those prepared with hydrophilic colloids that are known to be satisfactory for dispersing silver halides, for example, emulsions comprising natural materials such as gelatin, albumin, agar-agar, gum arabic, alginic acid, etc., and hydrophilic synthetic resins such as polyvinyl alcohol, polyvinyl pyrrolidone, cellulose ethers, partially hydrolyzed cellulose acetate, and the like.
  • the concentration of the dyes in the emulsion can vary widely, i.e., from about 5 to mg. per liter of flowable emulsion.
  • the specific concentration will vary according to the type of light-sensitive material in the emulsion and according to the effects desired.
  • the suitable and most economical concentration for any given emulsion will be apparent to those skilled in the art upon making the tests and observations customarily used in the art of emulsion making.
  • the dyes can be incorporated by other methods in many of the photographic silver halide emulsions customarily employed in the art.
  • the dyes can be incorporated by bathing a plate or film upon which an emulsion has been coated, in the solution of the dye in an appropriate solvent. Bathing methods, however, are not to be preferred ordinarily.
  • Photographic silver halide emulsions such as those listed above, containing the dyes described Hereiricari also contain such addenda as chemical sensitizers, e.g., sulfur sensitizers, (e.g., allyl thiocarbamide, thiourea, allylisothiocyanate, cystine, etc.), various gold compounds (e.g., potassium chloroaurate, auric trichloride, etc.) (see U.S. Pat. to W. D.
  • color couplers such as those described in I. F. Salminen et al., U.S. Pat. No. 2,423,730 granted July 7, 1947, Spence and Carroll U.S. Pat. No. 2,640,776, issued June 2, 1953, etc.; or mixtures of such addenda.
  • Dispersing agents for color couplers such as those set forth in U.S. Patents to E. E. Jelley et al. No. 2,322,027, granted June 15, 1943, and L. D. Mannes et al. No. 2,304,940, granted Dec. 15, 1942, can also be employed in the photographic emulsions of our invention.
  • R represents a member selected from the group consisting of phenyl, alkylphenyl, alkoxyphenyl, halogen substituted phenyl and nitrophenyl
  • R represents a member selected from the group consisting of an alkyl group, allyl, a sulfoalkyl group, a hydroxyalkyl group, an alkoxyalkyl group, a carboxyalkyl group, an alkanoyloxyalkyl group, an alkoxycarbonylalkyl group, an aralkyl group or an aryl group
  • R represents a member selected from the group consisting of a dialkylamino group and a nitro group
  • X represents an acid anion
  • A represents a member selected from the group consisting of a hydroxyalkyl group, a dialkylamino group, a dialsylesi noa kyl group fih group a (B b.
  • y represents a positive integer of from 1 to 2 and R represents a member selected from the group consisting of a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a dialkylamino group, a nitro group, a phenylazo group, an alkylthio group, a 2-methyl-5(or 6)-benzothiazolyl group, a 2-methyl-5(or 6)-benzoxazolyl group and a 2-methyl-5(or 6)- benzimidazolyl group
  • A represents a member selected from A when n is 1, and a divalent alkylene group when n is 2
  • Z represents the nonmetallic atoms required to complete a heterocyclic nucleus selected from the group consisting of a thiazole nucleus, a benzothiazole nucleus, a naphthothiazole nucleus, a thionaphtheno-7', 6, 4, S-thiazole nucleus,
  • a photographic silver halide emulsion in accordance 16 A photographic element comprising a support having coated thereon at least one layer containing a photographic silver halide emulsion of claim 2.
  • a photographic element comprising a support having coated thereon at least one layer containing a photographic silver halide emulsion of claim 3.
  • a photographic element comprising a support having coated thereon at least one layer containing a photographic silver halide emulsion of claim 4.
  • a photographic element comprising a support having coated thereon at least one layer containing a photographic silver halide emulsion of claim 5.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
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  • General Physics & Mathematics (AREA)
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  • Plural Heterocyclic Compounds (AREA)
US57831A 1970-07-23 1970-07-23 Silver halide emulsions containing a dye derived from 4,6-diaryl substituted picolinium salts as desensitizer Expired - Lifetime US3639127A (en)

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Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2352035A1 (fr) * 1976-05-17 1977-12-16 Minnesota Mining & Mfg Colorants methiniques de 4-nitrobenzylidene et leurs applications
US4876347A (en) * 1985-09-21 1989-10-24 Basf Aktiengesellschaft Methine dyes having a pyridyl group and a pyridyl or a quinolinyl group
US20040256598A1 (en) * 2003-04-01 2004-12-23 Gregory Plos Composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one compound comprising an acid functional group and processes therefor
US20040258641A1 (en) * 2003-04-01 2004-12-23 Gregory Plos Cosmetic composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one cationic polymer, and a dyeing process therefor
US20050005368A1 (en) * 2003-04-01 2005-01-13 Gregory Plos Process for dyeing, with a lightening effect, human keratin fibers that have been permanently reshaped, using at least one composition comprising at least one fluorescent dye
US20050008593A1 (en) * 2003-04-01 2005-01-13 Gregory Plos Dye composition comprising at least one fluorescent dye and a non-associative thickening polymer for human keratin materials, process therefor, and method thereof
US20050005371A1 (en) * 2003-04-01 2005-01-13 Chrystel Pourille-Grethen Method of dyeing human keratin materials with a lightening effect with compositions comprising at least one fluorescent dye and at least one amphoteric or nonionic surfactant, composition thereof, process thereof, and device therefor
US20050008594A1 (en) * 2003-04-01 2005-01-13 Gregory Plos Composiiton for dyeing human keratin materials, comprising at least one fluorescent dye and at least one polyol, process therefor and use thereof
US20050011018A1 (en) * 2003-04-01 2005-01-20 Andrew Greaves Process for dyeing human keratin fibers, having a lightening effect, comprising at least one fluorescent compound and compositions of the same
US20050028301A1 (en) * 2001-09-28 2005-02-10 Florent Pastore Dyeing composition with a brightening effect for human kerationous fibres
US20050031562A1 (en) * 2003-04-01 2005-02-10 Luc Gourlaouen Composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one associative polymer, process therefor and use thereof
US20050076457A1 (en) * 2003-04-01 2005-04-14 Gregory Plos Composition for dyeing a human keratin material, comprising at least one fluorescent dye and at least one insoluble conditioning agent, process thereof, use thereof, and devices thereof
US20050098763A1 (en) * 2003-04-01 2005-05-12 Gregory Plos Composition for dyeing human keratin materials, comprising a fluorescent dye and a particular sequestering agent, process therefor and use thereof
US20060010617A1 (en) * 2002-12-24 2006-01-19 Luc Gourlaouen Method for dyeing or coloring human keratin materials with lightening effect using a composition comprising at least one fluorescent compound and at least one optical brightener
JP2006111884A (ja) * 1993-07-12 2006-04-27 Molecular Probes Inc 環式置換−非対称シアニン染料
US7147673B2 (en) 2003-04-01 2006-12-12 L'oreal S.A. Composition for dyeing human keratin materials, comprising at least one fluorescent dye and at least one insoluble polyorganosiloxane conditioning polymer, process therefor and use thereof
JP2007291403A (ja) * 1994-10-27 2007-11-08 Molecular Probes Inc 選択された透過性を有する置換非対称シアニン色素
US20090288674A1 (en) * 2003-04-01 2009-11-26 L'oreal S.A. Cosmetic dye composition with a lightening effect for human keratin materials, comprising at least one fluorescent dye and at least one aminosilicone, and process of dyeing
CN1798540B (zh) * 2003-04-01 2010-05-26 莱雅公司 用于染色人角蛋白物质具有变淡效果的方法,特别的荧光或非荧光化合物以及含有它的组合物
US20100228008A1 (en) * 2005-05-24 2010-09-09 Enzo Life Sciences, Inc. C/O Enzo Biochem, Inc. Dyes linked to target molecules, oligonucleotides or polynucleotides comprising dye molecules, composite dyes and other compositions useful for detecting or quantifying desirable target molecules

Citations (2)

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US1994170A (en) * 1930-09-20 1935-03-12 Agfa Ansco Corp Compound of the distyryl pyridinium salt series and its production
US2984664A (en) * 1958-05-14 1961-05-16 Ilford Ltd Process for preparation of pentamethincyanines

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1994170A (en) * 1930-09-20 1935-03-12 Agfa Ansco Corp Compound of the distyryl pyridinium salt series and its production
US2984664A (en) * 1958-05-14 1961-05-16 Ilford Ltd Process for preparation of pentamethincyanines

Cited By (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2352035A1 (fr) * 1976-05-17 1977-12-16 Minnesota Mining & Mfg Colorants methiniques de 4-nitrobenzylidene et leurs applications
US4876347A (en) * 1985-09-21 1989-10-24 Basf Aktiengesellschaft Methine dyes having a pyridyl group and a pyridyl or a quinolinyl group
JP2006111884A (ja) * 1993-07-12 2006-04-27 Molecular Probes Inc 環式置換−非対称シアニン染料
JP2009280820A (ja) * 1994-10-27 2009-12-03 Molecular Probes Inc 選択された透過性を有する置換非対称シアニン色素
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GB1366506A (en) 1974-09-11
CA981516A (en) 1976-01-13
FR2103210A5 (Direct) 1972-04-07

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