US3898088A - Photographic elements containing polymeric mordants - Google Patents

Photographic elements containing polymeric mordants Download PDF

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Publication number
US3898088A
US3898088A US400778A US40077873A US3898088A US 3898088 A US3898088 A US 3898088A US 400778 A US400778 A US 400778A US 40077873 A US40077873 A US 40077873A US 3898088 A US3898088 A US 3898088A
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styrene
dye
polymer
polymers
mordants
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US400778A
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Hyman L Cohen
Frederick Koeng
I Ponticello
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Eastman Kodak Co
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Eastman Kodak Co
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Priority to US400778A priority Critical patent/US3898088A/en
Priority to CA209,107A priority patent/CA1057994A/en
Priority to FR7431745A priority patent/FR2257608B1/fr
Priority to AU73573/74A priority patent/AU485869B2/en
Priority to JP10992474A priority patent/JPS5534417B2/ja
Priority to DE2445782A priority patent/DE2445782B2/de
Priority to GB4193874A priority patent/GB1474750A/en
Priority to BE148946A priority patent/BE820394A/xx
Priority to US05/551,947 priority patent/US3944424A/en
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Publication of US3898088A publication Critical patent/US3898088A/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
    • G03C8/00—Diffusion transfer processes or agents therefor; Photosensitive materials for such processes
    • G03C8/42—Structural details
    • G03C8/52—Bases or auxiliary layers; Substances therefor
    • G03C8/56—Mordant layers
    • 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
    • G03C1/835—Macromolecular substances therefor, e.g. mordants
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00—Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/142—Dye mordant

Definitions

  • ABSTRACT A water-insoluble polymer comprising repeating units I at least 1/3 of said repeating units having the formula:
  • R and R are hydrogen or alkyl and R, R and R are alkyl groups wherein the total number of carbon atoms in R", R and R is at least 12 and X is an anion, is useful in dye mordant compositions in photographic elements.
  • Preferred dye mordants comprise copolymers with styrene or methyl methacrylate.
  • the present invention relates to novel polymeric compounds which are good mordants for dyes used in photographic systems and to photographic systems using such polymers.
  • dye mordants are those formed by quaternizing a polymer containing tertiary nitrogen atoms with an alkylating or aralkylating agent such as described in US. Pat. No. 3,625,694 issued Dec. 7, 1971, to Cohen et al, and US. Pat. No. 3,709,690 issued Jan. 9, 1973, to Cohen et al.
  • Still another object of this invention is to provide an integral negative receiverphotographic element comprising a support having a layer containing the polymeric mordant of this invention and at least one photosensitive silver halide emulsion layer which has contiguous thereto a dye image-providing material.
  • a dye mordant composition comprising a water-insoluble polymer comprising units represented by the following formula:
  • R and R are hydrogen or alkyl and R may be a group containing at least one aromatic nucleus
  • R, R and R are alkyl radicals comprising at least a total of 12 carbon atoms
  • X is an anion.
  • the water-insoluble polymers of the present invention containing alkyl substituents on the nitrogen atom containing a total of at least 12 carbon atoms have been found to be distinctly superior mordants.
  • Preferred polymers according to this invention comprise units having the following formula:
  • R and R are hydrogen or lower alkyl containing from 1 to 6 carbon atoms such as methyl, ethyl, propyl, butyl, pentyl, hexyl and the like and R can additionally be a group containing at least one aromatic necleus such as aryl including substituted aryl, such as phenyl, tolyl, naphthyl, biphenyl, anthracenyl and the like; R, R and R are alkyl such as methyl, ethyl, propyl, isopropyl, butyl, pentyl, hexyl, octyl, decyl and the like wherein the total number of carbon atoms in R R and R must be at least 12 and preferably from 12 to '30 and X is an anion; i.e., a monovalent negative salt forming ionic radical or atom such as a halide (e.g., a monovalent negative salt forming ionic
  • the polymers can be homopolymers or copolymers with at least one other ethylenically unsaturated monomer so long as at least 1/3 of the repeating units of the copolymer constitute those having the formula described above and the resulting homopolymer or copolymer is water-insoluble and the cationic moiety of the polymer is substantially free of carboxyl(COOH) groups.
  • carboxyl groups in the polymer interferes with effective dye mordanting.
  • Typical ethylenically unsaturated monomers which can be used to form ethenic copolymers (including two, three or more repeating units) according to this invention include ethylene, propylene, l-butene, isobutene, 2-methylpentene, 2-methylbutene, 1,1,4,4-tetramethylbutadiene, styrene, monoethylenically unsaturated esters of aliphatic acids such as vinyl acetate, isopropenyl acetate, allyl acetate, etc.; esters of ethylenically unsaturated monoor dicarboxylic acids such as methyl acrylate, methyl methaalpha-methylstyrene;
  • crylate ethyl acrylate, diethyl methylenemalonate, etc.; monoethylenically unsaturated compounds such as acrylonitrile, allyl cyanide, and dienes such as butadiene and isoprene.
  • a preferred class of ethylenically unsaturated monomers which may be used to form the ethenic polymers of this invention includes the lower l-alkenes having from 1 to 6 carbon atoms, styrene, and tetramethylbutadiene and methyl methacrylate.
  • the polymer must be water-insoluble.
  • a homopolymer having 12 carbon atoms on the R, R and R substituents may be watersoluble and inoperable for the purposes of this invention
  • a similar polymer interpolymerized with styrene in the range of to 80 percent by weight of the interpolymer may be water-soluble and can improve the mordanting properties desired.
  • water-insoluble it is meant that less than one gram of polymer will dissolve per 100 cc of water at room temperature (C).
  • the mordants of this invention are generally prepared by quaternizing a polymer comprising repeating units having the formula:
  • Typical suitable tertiary amines which may be used in this process include tributylamine, trihexylamine, tripentylamine, trioctylamine, diethyldodecylamine, dimethyltetradecylamine, dimethyloctadecylamine, dimethyldodecylamine, triisopentylamine and the like.
  • the vinyl polymer and tertiary amine may be reacted by heating in the presence of a solvent comprising alcohols (including aromatic alcohols) boiling above 100C, particularly methoxyethanol, ethoxyethanol, and benzyl alcohol.
  • the reaction may be carried out at any temperature but it is preferred to keep the reactants to from 70 to l 10C.
  • the reaction may be carried out using substantially equimolar amounts of the polymer e.g. poly(vinylbenzyl halide) or the like and tertiary amine.
  • An exchange of anions may be made, if desired, in order to produce polymeric, quaternary nitrogen group containing mordants to be employed in cer-, tain photographic supports such as dye-transfer systems.
  • the exchange of anions merely involves reacting the polymer with a salt such as silver acetate, silver p-toluenesulfonate or the like containing the preferred anion.
  • the polymers resulting from the above reaction may additionally contain some recurring units of the structure:
  • R is the residue of the alcohol solvent employed in the reaction mixture.
  • R may thus be an alkyl, alkaryl, aryl or alkoxyalkyl group such as methyl, ethyl, phenyl, benzyl, methoxyethyl, ethoxyethyl or the like.
  • the vinyl polymer may be incompletely quaternized by reacting less than a stoichiometric amount of tertiary amine with the polymer.
  • the preferred mole percent quaternization is from to 97.5 percent.
  • the excess haloalkyl groups in the polymer backbone are then further reacted with a compound having more than one amine group such as polyamine.
  • These polyamines may be represented by the formula Z(NR R), wherein Z is an organic group, R and R can be hydrogen, alkyl or aryl and n is 2 or more. Examples of polyamines useful herein are gelatin, 1,4-butanediamine, imidizole, pyrazine, and the like.
  • the amount of polyamine crosslinking agent added may vary from 0 to 20 percent by weight of the polymer. If the polyamine is also used as a binder material greater than 20 percent by weight can be added.
  • the alkylating process may be carried out in a solvent, such as water, acetone, benzene, dimethylfonnamide, dimethyl 'sulfoxide, dimethylacetamide, alcohols such as methanol, ethanol, isopropanol, 2-ethoxyethanol, and the like. Temperatures from 20 to 80C are generally used.
  • Some polymers which illustrate the mordants of this invention contain the following units wherein X is from 0 to 66 percent and y is IOO-X:
  • any of the methods known in the art to homopolymerize the monomers or to copolymerize with other ethylenically unsaturated monomers, such as mass, solution, or bead polymerization can be used to prepare the polymers of this invention, and polymerization catalysts known to the art, such as ultraviolet light treatment, peroxides, azo compounds [i.e., 2,2'-azobis(2- methylpropionitrile)], and the like can be employed.
  • Mordanting amounts of the novel polymers of the invention can be employed, as such, from solvent solutions such as methanol, ethanol, or mixtures of methano] or ethanol with water and the like, or can be incorporated in organic binder materials.
  • the resulting mixture can be used in the preparation of dye imbibition printing blanks, receiving layers for color transfer processes, such as those described in Land U.S. Pat. No. 3,362,819. Rogers U.S. Pat. No. 2,983,606, Whitmore U.S. Pat. No. 3,227,552 and U.S. Pat. No. 3,227,550, and in antihalation layers such as those described in Jones et al U.S. Pat. No. 3,282,699.
  • Satisfactory binders used for this purpose include any of the hydropho- 6O bic binders generally employed in the photographic field, including, for example, poly(vinyl acetate), cellulose acetate butyrate, gelatin, poly(vinyl alcohol) and the like. Exemplary materials are disclosed in Product Licensing Index, Vol. 92, Dec. 1971, publication 9,232, Page 108.
  • a mordanting amount of polymer can be employed in a dye mordanting or dye imagereceiving layer.
  • a binder can be used along with the polymeric mordant in the layer.
  • the amount of dye mordant to be used depends on the amount of dye to be mordanted, the mordanting polymers, the imaging chemistry involved, etc. and can be determined easily by one skilled in this art. It is preferred that between 20 and percent by weight of polymer be used in the dye mordanting layers.
  • the dye image-receiving element can comprise a support having thereon a layer including the polymeric mordant composition of this invention.
  • the element may also comprise other layers, such as a polymeric acid layer, and can also include a timing layer as taught in U.S. Pat. No. 3,362,819 or a light reflective interlayer comprising a light reflective white pigment, such as TiO and a polymeric binder, in accordance with the teaching of Beavers and Bush US Pat. No. 3,445,228.
  • the mordanting compositions of this invention are also especially useful in light-filtering layers, such as in antihalation layers of the type disclosed in Jones and Milton U.S. Pat. No. 3,282,699.
  • the light-filtering layer preferably can comprise a binder and the mordanting compositions of this invention.
  • the layer is adapted to contain a dye held or fixed by the mordanting composition.
  • novel mordants of this invention can also be employed in integral negative-receiver photographic elements such as those described in U.S. application Ser. No. 27,990 of Cole, filed Apr. 13, 1970, now abandoned U.S. application Ser. No. 2,991 of Barr et al., filed Apr. 13, 1970 now abandoned and U.S. Pat. No. 3,415,644 issued Dec. 10, 1968.
  • these integral photographic elements comprise a support having thereon a layer containing one or more of the novel mordants described herein and at least one photosensitive silver halide emulsion layer, the silver halide of which has contiguous thereto a dye image-providing material.
  • the mordants can also be used for fixing the dyes, and particularly acid dyes, used in the preparation of photographic filter, antihalation and gelatino vs silver halide emulsion layers.
  • Such layers can be coated on conventional photographic supports, such as flexible sheet supports (e.g., cellulose acetate, polyester films,
  • mordanting polymers of this invention can be used together, in a single layer or in two or more layers.
  • the mordanting polymers of this invention can also be used in admixture with other mordants in the same layer or in separate layers of the same element.
  • the total coverage of the mordanting layer or layers be from 5 to 55 mg/dm in order to satisfactorily operate as a mordant.
  • Emulsions or compositions containing the polymers can be chemically sensitized with compounds of the sulfur group and/or noble metal salts (such as gold salts), reduction sensitized with reducing agents, or any combination of these.
  • emulsion layers and other layers present in photographic elements made according to this invention can be hardened with any suitable hardener such as aldehyde hardeners, aziridine hardeners, hardeners which are derivatives of dioxane, oxypolysaccharides such as oxystarch, oxy plant gums, and the like.
  • the emulsion can also contain additional additives, particularly those known to be beneficial in photographic emulsions, including for example,
  • Mordanted blanks treated in accordance with this invention are useful for receiving acid dyes from hydrophilic colloid relief images according to prior art techniques.
  • Typical acid dyestuffs which can be transferred to the treated blanks of the invention are Anthracene Yellow GR (400 percent pure Schultz No. 177), Fast Red S Conc. (Colour Index 176), Pontacyl Green SN Ex. (Colour Index 737), Acid blue black (Colour Index 246), Acid Magenta (Colour Index 692), Naphthol Green B. Conc. (Colour Index Brilliant Paper Yellow Ex. Conc. 125 percent (Colour Index 364), Tartrazine (Colour Index 640), Metanil Yellow Conc. (Colour Index 138), Pontacyl Carmine 6B Ex. Conc. (Colour Index 57), Pontacyl Scarlet R Conc. (Colour Index 487) and Pontacyl Rubine R Ex. Conc. (Colour Index 179).
  • EXAMPLE 1 A reactor was charged with grams of poly(styrene-co-vinylbenzyl chloride) in a 1:1 mole ratio of styrene to vinylbenzyl chloride wherein 60 percent of the vinylbenzyl chloride is the meta isomer and 40 percent is the para isomer in 150 ml benzyl alcohol and 16 g of tris (n-pentyl)amine. The mixture was heated on a steam pot for about 16 hours, cooled, and poured into diethyl ether to precipitate the product.
  • poly (styrene-co- EXAMPLE 2 A mixture of 40 g of methyl methacrylate, 61 g of vinylbenzyl chloride, 500 mg of potassium persulfate, 200 mg of sodium bisulfite, 4 ml of the sodium salt of an alkyl-aryl poly(ether sulfate) commercially available under the trademark Triton 770 from Rohm and Haas Company and 200 ml of water was heated at 60C for 3 hours in a nitrogen atmosphere. The mixture was then held at -20C overnight and allowed to come to room temperature. The solid was filtered and washed with water and methanol. The white powder was dried under vacuum at room temperature. The resulting polymer had an inherent viscosity in acetone of 0.87.
  • a reactor was charged with a mixture of 12.5 g of poly (methyl methacrylate-co-vinylbenzyl chloride) prepared above, 21 g of trihexylamine and 200 ml of ethoxyethanol and heated at to C to 3 days in a nitrogen atmosphere. The polymer was precipitated from the resulting viscous solution in hexane, filtered,
  • the poly- 'mer was dissolved in methanol, and precipitated in a mixture of hexaneether 1:1 by volume).
  • the resulting copoly(methyl methacrylate-co,-N,N,N-tri-n-hexyl-N- vinylbenzylammonium chloride) had an inherent viscosity in methanol of 8.56 at 25C and at a concentration of 0.25 g/dl.
  • Example 3 The process of Example 2 was carried out with the substitution of tri-n-butylamine for tri-n-hexylamine. Poly(methyl methacrylate-co-N,N,N-tri-n-butyl-N- vinylbenzylammonium chloride) resulted.
  • EXAMPLE 4 The process of Example 2 was repeated with the substitution of triisopentylamine for tri-n-hexylamine. Poly(methyl methacrylate-co-N,N,N- triisopentylamine-N-vinylbenzylammonium chloride) resulted.
  • the polymers of the present invention were tested for CH -Q -GH lH- mordanting properties in relationship to a dye mordant similar to those described herein, [poly(styrene-co-N- Q benzyl-N ,N-dimethyl-N-( 3-maleimidopropyl )am- OH momum chloride].
  • the mordantmg property tested 2 was K, a competitive constant. 5 3
  • Test Mordant 1 EXAMPLE 26 This 18 a comparative example. Fluid and Dye The general method of reacting tertiary amines having lower alkyl substituents with polyvinyl benzyl chlo- Tio ride copolymers described in the prior art in U.S. Pat. 2 No. 3,178,396 to Lloyd and D. Jones and S. J. Getz, .l. W Ply.
  • the mixture was stirred and heated in a steam ings were taken at 24 hours to determine to which morb h f r 30 i Th polymer ll d d was i the ly q f? a greater
  • the K uble in acetone, methanol, benzene, N,N-dimethylfor- 1S determined by dividing the test mordant reflection mamide and dimethy] ]f id density by the standard mordant reflection density. This provides a ratio of mordanting ability of the tested mordant versus the standard mordant.
  • EXAMPLE 27 A reactor was charged with 50 grams of poly(styrene-co-vinylbenzyl chloride), 0.16 moles of tri-n-hexylamine and 900 ml of Z-methoxyethanol and the mixture was stirred for 24 hours at 95C. The solution was cooled and 15 mls of concentrated HCI were added. The mixture was poured into water, with stirring, to precipitate the polymer and the polymer was washed with water and dried in vacuum to produce 80 g of polymer which was 80 percent quatemized.
  • a photographic element comprising a support, a silver halide layer and a layer comprising a waterinsoluble polymer comprising repeating units represented by the following formula:
  • R and R are hydrogen or alkyl and R, R and R are alkyl groups wherein the total number of carbon atoms in R, R and R is at least 12 and X is an anion.
  • a photographic element of claim 1 wherein the water-insoluble polymer is a copolymer of at least one other ethylenically unsaturated monomer and wherein at least one-third of the repeating units comprise the formula of Claim 1.
  • R and R are hydrogen atoms or alkyl groups and R, R and R are alkyl groups wherein the total number of carbon atoms in R, R and R is at least 12 and X is an anion, having contiguous thereto a dye image providing material.

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US400778A 1973-09-26 1973-09-26 Photographic elements containing polymeric mordants Expired - Lifetime US3898088A (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
US400778A US3898088A (en) 1973-09-26 1973-09-26 Photographic elements containing polymeric mordants
CA209,107A CA1057994A (en) 1973-09-26 1974-09-12 Polymers and photographic elements containing same
FR7431745A FR2257608B1 (enrdf_load_stackoverflow) 1973-09-26 1974-09-20
AU73573/74A AU485869B2 (en) 1973-09-26 1974-09-23 Polymers and photographic elements containing same
JP10992474A JPS5534417B2 (enrdf_load_stackoverflow) 1973-09-26 1974-09-24
DE2445782A DE2445782B2 (de) 1973-09-26 1974-09-25 Photographisches Aufzeichnungsmaterial mit Bildempfangs- oder Lichthofschutzschicht
GB4193874A GB1474750A (en) 1973-09-26 1974-09-26 Polymers for photography
BE148946A BE820394A (fr) 1973-09-26 1974-09-26 Nouveaux mordants polymeres
US05/551,947 US3944424A (en) 1973-09-26 1975-02-21 Photographic or image recieving elements containing polymeric mordants

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US400778A US3898088A (en) 1973-09-26 1973-09-26 Photographic elements containing polymeric mordants

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JP (1) JPS5534417B2 (enrdf_load_stackoverflow)
BE (1) BE820394A (enrdf_load_stackoverflow)
CA (1) CA1057994A (enrdf_load_stackoverflow)
DE (1) DE2445782B2 (enrdf_load_stackoverflow)
FR (1) FR2257608B1 (enrdf_load_stackoverflow)
GB (1) GB1474750A (enrdf_load_stackoverflow)

Cited By (36)

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US3962527A (en) * 1973-03-09 1976-06-08 Eastman Kodak Company Novel polymers and photographic elements containing same
US4055429A (en) * 1975-11-13 1977-10-25 Eastman Kodak Company Inhibitor barrier layers for photographic materials
US4124386A (en) * 1973-10-24 1978-11-07 Fuji Photo Film Co., Ltd. Color diffusion transfer receiving layer comprising polymeric quaternary n-heterocyclic mordant
US4220700A (en) * 1978-02-03 1980-09-02 Eastman Kodak Company Continuous-tone dyed diazo imaging elements
US4220703A (en) * 1978-03-28 1980-09-02 Fuji Photo Film Co., Ltd. Photographic receiving layer with acid processed gelatin
US4247615A (en) * 1980-03-06 1981-01-27 Eastman Kodak Company Continuous-tone dyed diazo imaging process
DE3045447A1 (de) * 1979-12-03 1981-06-19 Polaroid Corp., 02139 Cambridge, Mass. Photographisches aufzeichnungsmaterial und verfahren
US4308335A (en) * 1979-07-20 1981-12-29 Fuji Photo Film Co., Ltd. Color diffusion transfer photographic elements
US4312940A (en) * 1978-08-31 1982-01-26 Fuji Photo Film Co., Ltd. Photographic material containing a novel polymer mordant
US4374194A (en) * 1980-12-08 1983-02-15 Eastman Kodak Company Dye imbibition photohardenable imaging material and process for forming positive dye images
WO1983001002A1 (en) * 1981-09-15 1983-03-31 Dynapol Shareholders Liquidati Quaternary ammonium group-containing polymers having antimicrobial activity
US4482680A (en) * 1981-09-15 1984-11-13 Dynapol Quaternary ammonium group-containing polymers having antimicrobial activity
US4532128A (en) * 1981-09-15 1985-07-30 Dynapol Quaternary ammonium group-containing polymers having antimicrobial activity
US4552835A (en) * 1983-06-17 1985-11-12 Fuji Photo Film Co., Ltd. Silver halide photographic light-sensitive element having a light insensitive upper layer
DE3601657A1 (de) * 1985-01-22 1986-07-24 Fuji Photo Film Co., Ltd., Minami-Ashigara, Kanagawa Photographisches element fuer ein silbersalzdiffusionsuebertragungsverfahren
WO1986004694A1 (en) 1985-02-06 1986-08-14 Fuji Photo Film Co., Ltd. Silver halide photographic photo-sensitive material
EP0210660A2 (en) 1985-07-31 1987-02-04 Fuji Photo Film Co., Ltd. Image forming process
US4794067A (en) * 1987-11-23 1988-12-27 Polaroid Corporation, Patent Dept. Copolymeric mordants and photographic products and processes containing same
US4808510A (en) * 1987-08-20 1989-02-28 Eastman Kodak Company Photographic element and patternable mordant composition
US4812391A (en) * 1986-10-17 1989-03-14 Fuji Photo Film Co., Ltd. Silver halide photographic material containing polymer fixation accelerator
EP0313051A1 (en) 1987-10-20 1989-04-26 Fuji Photo Film Co., Ltd. Silver halide photographic material
US4879204A (en) * 1985-01-29 1989-11-07 Fuji Photo Film Co., Ltd. Silver halide photographic element containing anhydazine compound and specific dyes
US4920036A (en) * 1985-09-20 1990-04-24 Fuji Photo Film Co., Ltd. Photosensitive recording element having pigmented photopolymer layer
US4954339A (en) * 1987-12-23 1990-09-04 Smith Kline & French Laboratories Limited Novel polystyrene anion exchange polymers
US5098701A (en) * 1989-12-04 1992-03-24 Smithkline & French Laboratories, Ltd. Crosslinked pyridinomethacrylate polymers
US5230993A (en) * 1987-06-05 1993-07-27 Fuji Photo Film Co., Ltd. Silver halide photographic element
US5230885A (en) * 1987-12-23 1993-07-27 Smith Kline & French Laboratories Limited Polystyrene anion exchange polymer pharmaceutical composition
EP0580041A2 (en) 1992-07-10 1994-01-26 Fuji Photo Film Co., Ltd. Method of processing silver halide photographic material and composition for processing
EP0589460A1 (en) 1992-09-24 1994-03-30 Fuji Photo Film Co., Ltd. Method for processing a black & white silver halide light-sensitive material
US5622808A (en) * 1995-06-20 1997-04-22 Eastman Kodak Company Receiver for dye imbibition printing
EP0777153A1 (en) 1995-11-30 1997-06-04 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive material
US5654202A (en) * 1992-03-24 1997-08-05 Eastman Kodak Company Stabilization of a patterned planarizing layer for solid state imagers prior to color filter pattern formation
US5709971A (en) * 1995-06-20 1998-01-20 Eastman Kodak Company Dye imbibition printing blanks with antistatic layer
US20050195261A1 (en) * 2004-03-05 2005-09-08 Eastman Kodak Company Fuser for ink jet images and ink formulations
EP1635216A1 (en) 2004-09-14 2006-03-15 Fuji Photo Film Co., Ltd. Photothermographic material
US7368296B2 (en) 2002-01-17 2008-05-06 Applied Biosystems Solid phases optimized for chemiluminescent detection

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JPS6048025B2 (ja) * 1977-09-16 1985-10-24 コニカ株式会社 ハロゲン化銀写真感光材料
US4315978A (en) * 1980-03-06 1982-02-16 Eastman Kodak Company Solid-state color imaging device having a color filter array using a photocrosslinkable barrier
EP0307867A3 (en) * 1987-09-14 1990-08-08 Konica Corporation Light-sensitive silver halide photographic material having superior sharpness and feasible for ultra-rapid processing

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US3625694A (en) * 1968-06-06 1971-12-07 Kodak Ltd Polymers polymeric mordants and elements containing same
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US4124386A (en) * 1973-10-24 1978-11-07 Fuji Photo Film Co., Ltd. Color diffusion transfer receiving layer comprising polymeric quaternary n-heterocyclic mordant
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US4220700A (en) * 1978-02-03 1980-09-02 Eastman Kodak Company Continuous-tone dyed diazo imaging elements
US4220703A (en) * 1978-03-28 1980-09-02 Fuji Photo Film Co., Ltd. Photographic receiving layer with acid processed gelatin
US4312940A (en) * 1978-08-31 1982-01-26 Fuji Photo Film Co., Ltd. Photographic material containing a novel polymer mordant
US4308335A (en) * 1979-07-20 1981-12-29 Fuji Photo Film Co., Ltd. Color diffusion transfer photographic elements
DE3045447A1 (de) * 1979-12-03 1981-06-19 Polaroid Corp., 02139 Cambridge, Mass. Photographisches aufzeichnungsmaterial und verfahren
US4247615A (en) * 1980-03-06 1981-01-27 Eastman Kodak Company Continuous-tone dyed diazo imaging process
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WO1983001002A1 (en) * 1981-09-15 1983-03-31 Dynapol Shareholders Liquidati Quaternary ammonium group-containing polymers having antimicrobial activity
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DE3601657A1 (de) * 1985-01-22 1986-07-24 Fuji Photo Film Co., Ltd., Minami-Ashigara, Kanagawa Photographisches element fuer ein silbersalzdiffusionsuebertragungsverfahren
DE3601657C2 (de) * 1985-01-22 1998-01-29 Fuji Photo Film Co Ltd Photographisches Aufzeichnungsmaterial für das Silbersalzdiffusionsübertragungsverfahren
US4879204A (en) * 1985-01-29 1989-11-07 Fuji Photo Film Co., Ltd. Silver halide photographic element containing anhydazine compound and specific dyes
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US5230993A (en) * 1987-06-05 1993-07-27 Fuji Photo Film Co., Ltd. Silver halide photographic element
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US5230885A (en) * 1987-12-23 1993-07-27 Smith Kline & French Laboratories Limited Polystyrene anion exchange polymer pharmaceutical composition
US4954339A (en) * 1987-12-23 1990-09-04 Smith Kline & French Laboratories Limited Novel polystyrene anion exchange polymers
US5098701A (en) * 1989-12-04 1992-03-24 Smithkline & French Laboratories, Ltd. Crosslinked pyridinomethacrylate polymers
US5654202A (en) * 1992-03-24 1997-08-05 Eastman Kodak Company Stabilization of a patterned planarizing layer for solid state imagers prior to color filter pattern formation
EP0580041A2 (en) 1992-07-10 1994-01-26 Fuji Photo Film Co., Ltd. Method of processing silver halide photographic material and composition for processing
EP0589460A1 (en) 1992-09-24 1994-03-30 Fuji Photo Film Co., Ltd. Method for processing a black & white silver halide light-sensitive material
US5622808A (en) * 1995-06-20 1997-04-22 Eastman Kodak Company Receiver for dye imbibition printing
US5709971A (en) * 1995-06-20 1998-01-20 Eastman Kodak Company Dye imbibition printing blanks with antistatic layer
EP0777153A1 (en) 1995-11-30 1997-06-04 Fuji Photo Film Co., Ltd. Silver halide color photographic light-sensitive material
US7368296B2 (en) 2002-01-17 2008-05-06 Applied Biosystems Solid phases optimized for chemiluminescent detection
US20080227124A1 (en) * 2002-01-17 2008-09-18 Brooks Edwards Solid phases optimized for chemiluminescent detection
EP2101174A1 (en) 2002-01-17 2009-09-16 Applied Biosystems, LLC Solid phases optimized for chemiluminescent detection
US20050195261A1 (en) * 2004-03-05 2005-09-08 Eastman Kodak Company Fuser for ink jet images and ink formulations
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Also Published As

Publication number Publication date
CA1057994A (en) 1979-07-10
FR2257608A1 (enrdf_load_stackoverflow) 1975-08-08
JPS5061228A (enrdf_load_stackoverflow) 1975-05-26
FR2257608B1 (enrdf_load_stackoverflow) 1976-10-22
DE2445782A1 (de) 1975-04-03
GB1474750A (en) 1977-05-25
AU7357374A (en) 1976-03-25
DE2445782B2 (de) 1979-06-28
BE820394A (fr) 1975-03-26
JPS5534417B2 (enrdf_load_stackoverflow) 1980-09-06

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