US3702767A - Spectrally sensitized light sensitive material - Google Patents

Spectrally sensitized light sensitive material Download PDF

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US3702767A
US3702767A US103798A US3702767DA US3702767A US 3702767 A US3702767 A US 3702767A US 103798 A US103798 A US 103798A US 3702767D A US3702767D A US 3702767DA US 3702767 A US3702767 A US 3702767A
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dye
dyes
silver halide
group
oxo
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Hans Ohlschlager
Oskar Riester
Heinz Meckl
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Agfa Gevaert AG
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Agfa Gevaert AG
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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
    • C09B23/0008—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain
    • C09B23/0025—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain the substituent being bound through an oxygen atom
    • 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
    • C09B23/0008—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain
    • C09B23/005—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain the substituent being a COOH and/or a functional derivative thereof
    • C09B23/0058—Methine or polymethine dyes, e.g. cyanine dyes substituted on the polymethine chain the substituent being a COOH and/or a functional derivative thereof the substituent being CN
    • 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
    • C09B23/0075—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain being part of an heterocyclic ring
    • 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
    • C09B23/10—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
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0622—Heterocyclic compounds
    • G03G5/0644—Heterocyclic compounds containing two or more hetero rings
    • G03G5/0661—Heterocyclic compounds containing two or more hetero rings in different ring systems, each system containing at least one hetero ring
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0664—Dyes
    • G03G5/0666—Dyes containing a methine or polymethine group
    • G03G5/0668—Dyes containing a methine or polymethine group containing only one methine or polymethine group
    • G03G5/067—Dyes containing a methine or polymethine group containing only one methine or polymethine group containing hetero rings
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/06—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor characterised by the photoconductive material being organic
    • G03G5/0664—Dyes
    • G03G5/0666—Dyes containing a methine or polymethine group
    • G03G5/0672—Dyes containing a methine or polymethine group containing two or more methine or polymethine groups
    • G03G5/0674—Dyes containing a methine or polymethine group containing two or more methine or polymethine groups containing hetero rings

Definitions

  • the invention relates to light sensitive layers, in particular to silver halide emulsion layers, which are spectrally sensitized with new types of sensitizing dyes.
  • the adsorption on the silver halide should be so strong that the sensitizing effect is disturbed as little as possible by other necessary additives such as Wetting agents and emulsifiers, stabilizers, colour couplers, dyes which can be bleached, white toners, etc.
  • the sensitization must also be ensured under extreme conditions such as elevated temperature and high humidity.
  • the sensitizing dyes must not increase the basic fog present, as occasionally occurs with basic cyanine dyes.
  • the sensitizing dyes must, in addition, have certain sensitizing properties which, apart from a sufficient intensity of sensitization in the sensitization range, include above all a steep decrease in sensitization at the transition to longer wavelengths of light. For the reasons mentioned above, there is considerable interest in finding new sensitizing dyes which do not have the disadvantages mentioned.
  • sensitizing dyes for sensitizing light sensitive layers in particular silver halide emulsion layers, which do not have the disadvantages mentioned above.
  • a photographic material comprising at least one spectrally sensitized silver halide emulsion layer has now been found which contains, as sensitizing dyes, a dye of the following Formula I or II:
  • R R and R are the same or different radicals and are hydrogen, alkyl preferably containing up to 6 carbon atoms such as methyl, ethyl, propyl, isopropyl or butyl, cycloalkyl such as cyclohexyl, aralkyl such as benzyl or aryl such as phenyl;
  • R and R are the same or diflierent radicals and are (1) saturated or unsaturated aliphatic groups which preferably contain up to 6 carbon atoms and which may be substituted, e.g. with phenyl, hydroxy, amino, carboxyl, sulpho, sulphonylamino, sulphamyl, carbonamido, carbamyl, carbalkoxy, sulphato or thiosulphato, (2) cycloalkyl such as cyclohexyl or (3) aryl, in particular phenyl;
  • R and R are the same or different radicals, and are hydrogen, saturated or olefinically unsaturated aliphatic groups containing up to 3 carbon atoms, alkoxy preferably having up to 3 carbon atoms, such as methoxy or ethoxy, alkylthio having preferably up to 3 carbon atoms, such as methylthio or ethylthio, or aryl, for example phenyl;
  • R R and R are the same or different radicals and are (1) hydrogen, (2) saturated or olefinically unsaturated aliphatic groups which may be substituted, e.g. with phenyl, hydroxyl or carboxyl, or (3) aryl such, for example, as phenyl or naphthyl;
  • R cyano, carbalkoxy or thiocarbamido
  • X and Z are the same or different and represent O-
  • S, --NR or CO-NR p, q and r anion are the same or different and represent 0 or 1; any photographically inert, e.g. halide such as chloride, bromide or iodide, perchlorate, sulphate, methylsulphate, p-toluenesulphonate and the like; the anion is absent if R contains an acid group in anionic form so that a betaine is present;
  • Q a radical required to complete a heterocyclic group comprising a S-membered or 6-membered hetero ring;
  • the heterocyclic group may also comprise a condensed benzene or naphthalene ring and may contain further substituents;
  • the heterocyclic groups may be any of alkoxy preferably'with up or ethyl, halogen such as chlorine or bromine, hydroxyl,
  • xo-5,6,7,8-tetrahydroquinolines are heterocyclic bases which can easily be prepared by condensation of dihydroresorcinols with 1,3 dicarbonyl compounds or their derivatives in the presence of ammonia or ammonium acetate.
  • the merocyanines are obtained e.g. by condensation of a quaternary salt of a 2-methyl- (or 4-methyl-) 5-oxo- 5,6,7,8-tetrahydroquinoline base with an alkoxyalkylidene derivative of a cyclic ketornethylene compound, for example N-alkyl 5 ethoxymethylenerhodanine or by condensation of a Z-anilidovinylquaternary salt of a 5- 0x0 5,6,7,8 tetrahydroquinoline with ketomethylene compounds. e.g. with rhodanines, oxazolidone thiones,
  • thiohydantoins or pyrazolones If a quaternary salt of 2,4 dimethyl 5 oxa-tetrahydroquinoline is used, condensation occurs either at the methyl group in the 4-position or at the methyl group in the 2-position, depending on the condensation conditions and the solvent.
  • 1,2,4 trimethyl 5 oxo-tetrahydroquinolinium methyl sulphate with N-ethyl-5-ethoxymethylene rhodanine in pyridine for example, Dye 3 is obtained whereas when alcohol is used as solvent, Dye 2 is obtained.
  • additional dyes can be prepared by known methods, for example by further quaternisation and renewed condensation, e.g. with 'keto methylene compounds or with 2 methylquaternary salts of heterocyclic bases.
  • further condensation of merocyanines obtained from rhodanine rhodacyanines are obtained.
  • Mono and tri-methine dyes may also be prepared by the usual processes, for example starting from 2- (or 4-) methyl 5 0x0 5,6-,'7,8 tetrahydroquinolinium quaternary salts by condensation with suitably substituted derivatives of any heterocyclic bases, e.g. 2-alkylthioor 2 anilidovinyl-quaternary salts, or conversely by condensation of 2 anilidovinyl 5 oxo 5,6,7,8-tetrahydroquinoline quaternary salts with 2 methylquaternary salts of heterocyclic bases.
  • Dye2 1.7 g. of 2,4 dimethyl 5 oxo 5,6,7, 8-tetrahydroquinoline and 1.1 ml. of dimethylsulphate are heated on an oil bath to 60 C., the reaction temperature rising to C. The mixture is heated for another 10 minutes at C. and then heated on a steam bath for 15 minutes together with 2.1 g. of N-ethyl-S-ethoxymethylenerhodanine and 2 ml. of triethylamine in 20 ml. of alcohol. Dye 2 precipitates. After cooling, it is isolated by suction filtration and recrystallised from chloroform/ methanol. 1.7 g., M.P.: 241 C. (decomposition).
  • Dye 9 1.7 g. of Dye 1 and 2.5 ml. of dimethylsulphate are heated to 110 C. on an oil bath for 15 minutes.
  • the quaternary salt obtained is triturated with acetone to remove excess dimethylsulphate and then heated on a steam bath for minutes together with 0.8 g. of N- ethylrhodanine in 50 ml. of alcohol with the addition of 2 ml. of triethylamine.
  • the mixture is cooled and Dye 9 is isolated by suction filtration, washed with methanol and recrystallised from chloroform/methanol. 0.8 g., M.P.: 273-276" C.
  • Dye 24 3.4 g. of Dye 1 are quaternised as described in the previous example and the quaternary salt is heated on a steam bath for minutes together with 3.3 g. of 2,5,6 trimethyl 3 ethyl-benzothiazolium iodide in ml. of alcohol and 2 ml. of triethylamine. The dye which crystallises on cooling is removed by suction filtration and recrystallised from methanol. 1.7 g. of Dye 24 is obtained, M.P. 273-275 C. (decomposition).
  • Dye 34 4.2 g. of 1-methyl-2-anilidovinyl-5-oxo-5,6,7,8-tetra-hydroquinolinium tosylate and 3.2 g. of N-methyllepidinium tosylate in 30 ml. of acetonitrile are heated together on a steam bath for 10 minutes with the addition of 2 ml. of triethylamine and 1.5 ml. of acetic acid anhydride. After cooling, suction filtration and recrystallisation from methanol, 2.3 g. of Dye 34 of MP. 215 C. are obtained.
  • the absorption maxima and sensitization maxima of the dyes according to the invention are shifted towards longer wavelengths by 15 to 20 nm. compared with comparable dyes derived from uor 'y-picoline (absorption maximum of 3-ethyl-5- 1-ethyl-2'(1 (H) pyridylidene ethylene] -rhodanine: 540 nm.; Brooker et al., J. Am. Chem. Soc. 73, 5336).
  • the dyes according to the invention produce sensitizations of high intensity on silver halide emulsions and in contrast to the corresponding quinoline dyes they show a spectrally narrower sensitization curve.
  • the s'ensitizations obtained are completely resistant to the influence of the usual additives such as wetting agents, emulsifiers, stabilizers and colour couplers or dyes which can be bleached, even at elevated temperature and high humidity. It has also been found to be an advantage that the dyes can be easily Washed out so that photographic layers which have been sensitized with these dyes have no interfering colour after processing. The dyes are therefore valuable sensitizers especially for colour photographic materials.
  • the sensitizing dyes according to the invention may be used in any silver halide emulsions.
  • Suitable silver halides are silver chloride, silver bromide or mixtures thereof, if desired with a small silver iodide content of up to 10 mol percent.
  • the silver halides may be dispersed in the usual hydrophilic compounds, for example in carboxymethylcellulose, polyvinyl alcohol, poyvinylpyrrolidone, alginic acid and its salts, esters or amides or, preferably, in gelatine.
  • the sensitizing dyes for use according to the present invention are advantageously added to the photographic emulsions after chemical ripening and before casting.
  • the methods used for this are generally known in the art.
  • the sensitizing dyes are generally incorporated with the emulsion in the form of solutions, e.g. in alcohol or mixtures of alcohol and water.
  • the solvents must, of course, be compatible with gelatine and must not exert any adverse influence on the photographic properties of the emulsion. Water, methanol or mixtures thereof are generally used as solvents.
  • the quantity of sensitizing dye added may vary within wide limits, e.g. between 10 and mg. per mol of silver halide, preferably between 30 and 300 mg. per mol of silver halide.
  • the concentration of the dye can be adapted to the given requirements, depending on the nature of the emulsion, the desired sensitization effect, etc. The most suitable concentration for any given emulsion can easily be determined by the usual tests employed in photographic practice.
  • the emulsions may also be chemically sensitized, e.g. by the addition of compounds which contain sulphur during chemical ripening, for example allyl isothiocyanate, allyl thiourea, sodium thiosulphate and the like.
  • Reducing agents e.g. the tin compounds described in Belgian patent specifications Nos. 493,464 or 568,687, polyamines such as diethylenetriamine or aminomethylsulphinic acid derivatives, e.g. according to British patent specification No. 789,823, may also be used as chemical sensitizers.
  • Noble metals or noble metal compounds such as gold, platinum, palladium, iridium, ruthenium or rhodium are also suitable chemical sensitizers. This method of chemical sensitization has been described in the article by R. Koslowsky, Z. Wiss. Phot. 46, 65-72 (1951).
  • the emulsions may also be sensitized with polyalkylene oxide derivatives, e.g. with polyethylene oxide having a molecular weight of between 1,000 and 20,000, or with condensation products of alkylene oxide and aliphatic alcohols, glycols, cyclic dehydration products of hexitols, alkyl substituted phenols, aliphatic carboxylic acids, aliphatic amines, aliphatic diamines and amides.
  • the condensation products have a molecular weight of at least 700 and preferably more than 1,000.
  • the emulsions may in addition also contain other spectral sensitizers, e.g. the usual polymethine dyes such as neutrocyanines, basic or acid carbocyanines, rhodacyanines, hemicyanines, styryl dyes, oxonoles and the like. Sensitizers of this type have been described in the work by F. M. Hamer The Cyanine Dyes and related Compounds (1964).
  • spectral sensitizers e.g. the usual polymethine dyes such as neutrocyanines, basic or acid carbocyanines, rhodacyanines, hemicyanines, styryl dyes, oxonoles and the like.
  • Sensitizers of this type have been described in the work by F. M. Hamer The Cyanine Dyes and related Compounds (1964).
  • the monoand tri-methinecyanines of the present invention may advantageously be combined with compounds which contain a mercapto group and a sulphonic acid group such as those mentioned in French patent specification No. 1,426,623; a supersensitizing efiect is then observed.
  • the emulsions according to the invention may contain the usual stabilizers, e.g. homopolar or salt-containing compounds of mercury with aromatic or heterocyclic rings, such as mercaptotriazoles, simple mercury salts, sulphonium mercury double salts and other mercury compounds.
  • suitable stabilizers include azaindenes, especially tetraand pentaazaindenes, in particular those which are substituted with hydroxyl or amino groups. Compounds of this type have been described in the article by Birr, Z. Wiss. Phot. 47, 258, (1952).
  • Other suitable stabilizers include heterocyclic mercapto compounds, e.g. phenylmercapto tetrazole, quaternary benzothiazole derivatives, benzotriazole and the like.
  • the emulsions may be hardened in the usual manner, for example with formaldehyde or halo-substituted aldehydes which contain a carboxyl group, such as mucobromic acid, di-ketones, methanesulphonic acid esters, dialclehydes and the like.
  • the emulsions according to the invention may be used for various photographic processes, for example for materials used for producing original photographs, for copying materials, for reprotechnical films, for X-ray films, for materials which are suitable for the silver salt diffusion process, for colour photographic materials, for photographic materials for the silver dye bleaching process, etc.
  • the sensitizers for use according to the invention are in addition suitable for the spectral sensitization of electrophotographic layers, especially layers which contain photoconductive zinc oxide distributed in an insulating binder.
  • EXAMPLE 1 To 1 kg. of a conventional silver chlorobromide emulsion are added 10 g. of sodium salt of the cyan-forming coupler 1 hydroxy-4-sulfo-N-n-octadecyl-2-naphthamide as a 5% aqueous solution and are further added mg. of a dye of the following Table 1. The emulsion is cast on a baryta-coated paper and dried. The various samples are exposed behind a step-wedge (V5 steps) and filters which are transparent only for red or green light, respectively. The samples are then developed in a color-forming developer bath, follower by fixing and rinsing.
  • V5 steps step-wedge
  • the outstanding sensitizing intensity of the dyes according to the invention is shown in the following Table 1 from the number of visible steps which is used as a measure for the relative sensitivity of the sensitized emulsions.
  • the known red sensitizer of the following formula is used as comparison.
  • EXAMPLE 2 In this example is shown the sensitization of an electrophotographic zinc oxide layer using the dyes according to the present invention.
  • This mixture is cast on a baryta-coated paper (25 g. of zinc oxide per m9) and dried.
  • the samples are charged and then exposed for 15 seconds behind a step wedge (increase of density 0.1) using an incandescent lamp of 450 watt and an intensity of 2280 lux.
  • the development is performed according to a common developing method employing a powder developer.
  • the senitivity is shown by the number of steps at which no toner 24 aparticles are deposited a ndwhich maintain the original density. The more steps, the greater is the sensitivity.
  • a light sensitive photographic material which comprises a sensitising dye selected from the group consisting of the Formulae I or II:
  • a silver halide emulsion containing material as claimed in claim 1 which comprises 10 to 1000 mg. of the said dye per mol of silver halide.
  • a material as claimed in claim 1 which comprises 30 to 300 mg. of dye per mole of silver halide.
  • a material as claimed in claim 2 which also comprises one or more colour couplers.
  • a silver halide emulsion containing material as claimed in claim 5 which comprises 10 to 1000 mg. of the said dye per mole of silver halide.
  • a material as claimed in claim 3 which also comprises one or more couplers.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Photoreceptors In Electrophotography (AREA)
  • Plural Heterocyclic Compounds (AREA)
US103798A 1970-01-15 1971-01-04 Spectrally sensitized light sensitive material Expired - Lifetime US3702767A (en)

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BE (1) BE761459A (enExample)
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GB (1) GB1339491A (enExample)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3844798A (en) * 1969-07-10 1974-10-29 Agfa Gevaert Ag Spectrally sensitized light-sensitive silver halide photographic material
US5256784A (en) * 1992-01-16 1993-10-26 Minnesota Mining And Manufacturing Company Nonlineaphores and polymers incorporating such nonlineaphores
US5362812A (en) * 1993-04-23 1994-11-08 Minnesota Mining And Manufacturing Company Reactive polymeric dyes
US5422236A (en) * 1993-09-27 1995-06-06 Minnesota Mining And Manufacturing Company Spectrally sensitized silver halide photographic elements

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7550482B2 (en) 2004-02-27 2009-06-23 Merz Pharma Gmbh & Co. Kgaa Tetrahydroquinolones and their use as modulators of metabotropic glutamate receptors
TWI301760B (en) 2004-02-27 2008-10-11 Merz Pharma Gmbh & Co Kgaa Tetrahydroquinolinones and their use as antagonists of metabotropic glutamate receptors

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3844798A (en) * 1969-07-10 1974-10-29 Agfa Gevaert Ag Spectrally sensitized light-sensitive silver halide photographic material
US5256784A (en) * 1992-01-16 1993-10-26 Minnesota Mining And Manufacturing Company Nonlineaphores and polymers incorporating such nonlineaphores
US5362812A (en) * 1993-04-23 1994-11-08 Minnesota Mining And Manufacturing Company Reactive polymeric dyes
US5532111A (en) * 1993-04-23 1996-07-02 Minnesota Mining And Manufacturing Company Reactive polymeric dyes
US5741620A (en) * 1993-04-23 1998-04-21 Minnesota Mining And Manufacturing Company Reactive polymeric dyes
US5422236A (en) * 1993-09-27 1995-06-06 Minnesota Mining And Manufacturing Company Spectrally sensitized silver halide photographic elements

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DE2001572A1 (de) 1971-07-22
BE761459A (nl) 1971-07-12
GB1339491A (en) 1973-12-05
FR2075616A5 (enExample) 1971-10-08

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