US2772163A - Photographic emulsions containing couplers and hydrosols - Google Patents

Photographic emulsions containing couplers and hydrosols Download PDF

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Publication number
US2772163A
US2772163A US349348A US34934853A US2772163A US 2772163 A US2772163 A US 2772163A US 349348 A US349348 A US 349348A US 34934853 A US34934853 A US 34934853A US 2772163 A US2772163 A US 2772163A
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United States
Prior art keywords
hydrosol
emulsion
coupler
acid
solution
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Expired - Lifetime
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US349348A
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English (en)
Inventor
Tong Lee Karl Jan
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Eastman Kodak Co
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Eastman Kodak Co
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Priority to BE528163D priority Critical patent/BE528163A/xx
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Priority to US349348A priority patent/US2772163A/en
Priority to DEE8851A priority patent/DE965616C/de
Priority to FR1110268D priority patent/FR1110268A/fr
Priority to GB11365/54A priority patent/GB759409A/en
Application granted granted Critical
Publication of US2772163A publication Critical patent/US2772163A/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
    • G03C7/00—Multicolour photographic processes or agents therefor; Regeneration of such processing agents; Photosensitive materials for multicolour processes
    • G03C7/30—Colour processes using colour-coupling substances; Materials therefor; Preparing or processing such materials
    • G03C7/388—Processes for the incorporation in the emulsion of substances liberating photographically active agents or colour-coupling substances; Solvents therefor
    • G03C7/3882—Processes for the incorporation in the emulsion of substances liberating photographically active agents or colour-coupling substances; Solvents therefor characterised by the use of a specific polymer or latex

Definitions

  • This invention relates to photography and particularly to a method of incorporating color-forming compounds in photographic emulsions.
  • Coupler compounds capable of coupling with the oxidation product of primary aromatic amino developing agents may be incorporated in'photographic gelatin or silver halide emulsions in a variety of ways depending upon the solubility characteristics of the couplers-and their intended use.
  • Couplers which are solu'ble or partially soluble in water or aqueous systems may be incorporated directly in gelatin usuallyas the alkali metal salt, as described in Fischer, U. S. Patent 1,102,028.
  • Couplers which are soluble in oils or organic solvents may first be mixed with a solvent for the coupler and the solution dispersed in the gelatin as described in Mannes and Godowsky, U. S. Patent 2,304,940, and Ielley and Vittum, U. S.
  • a further object is to provide for incorporating couplers of lower solubility in organic solvents in photographic emulsions.
  • a still further object is to provide a method permitting increased amounts of coupler to be dispersed in photographic emulsions.
  • hydrophilic colloid-coupler mixture a latex or hydrosol of a water-insoluble synthetic polymer including at least an ester of acrylic acid or methacrylic acid with an aliphatic acid having not more than 10 carbon atoms.
  • Figure 1 is a sectional view of a single layer film according to my invention and Figure 2 is a sectional view of a multilayer photographic film constructed according to my invention.
  • My invention is concerned principally With the incorporation of couplers or color-forming compounds in 'gelatino-silver halide emulsions although silver halide 2,772,163 Patented Nov. 27, 1956 "ice to the silver halide emulsion.
  • the solution of coupler may, however, be mixed with the silver halide emulsion and the latex or hydrosol then added.
  • the resulting emulsion containing the coupler and the latex or hydrosol is then coated and dried in the usual Way.
  • the coupler appears in finely dispersed. solid particles and the resin latex is completely compatible with the gelatin or other hydrophilic colloid forming a uniform smooth layer of the colloid.
  • the latex or hydrosol which constitutes the essential feature of my invention is a colloidal suspension in water of a synthetic polymer including at least an ester of acrylic or methacrylic acid with an aliphatic alcohol having not more than 10 carbon atoms.
  • Suitable esters include methylacrylate, ethylacrylate, n-propyl acrylate, isopropyl acrylate, n-butylacrylate, methyl methacrylate, ethyl methacrylate, etc. These may be copolymerized with nitriles, e. g., acrylonitrile, or with styrene or substituted styrenes, e.
  • Three component polymers may be made by copolymerizing the acrylic or methacrylic acid esters with nitriles or styrenes and acrylamide or methacrylamide or alkyl substituted derivatives of acrylamide or methacrylamide.
  • the latex or hydrosol is produced by polymerizing or copolymerizing the monomer or monomers in water or other aqueous system.
  • the method of preparing the hydrosol is not part of my invention but is the invention of William F. Fowler, Jr. and is described in his U. S. Patent 2,739,137. Any of the monomers referred to in that application may be used in preparing the hydrosols which I use.
  • EXAMPLE 1 This example illustrates the incorporation of Waterinsoluble couplers in silver halide emulsions.
  • a hydrosol prepared by the emulsion polymerization of a mixture of 58.8% n-butyl acrylate, 25.2% styrene and 16% methacrylamide as described in Fowler U. S. Patent 2,739,137 using persulfate catalysts and sodium lauryl sulfate as the dispersing agent was diluted to 20% solids concentration.
  • the coupler dispersion was mixed with an equal volume of gelatino-silver halide emulsion containing 17 grams of silver halide per liter of emulsion. After mixing for /2 hour the emulsion was coated on a cellulose acetate supportand dried in the usual way. The coating was clear and showed particles of coupler but no particles of resin upon microscopic examination at 800 diameters.
  • magenta couplers of U. S. Patent 2,369,489 and the cyan couplers of U. S. Patent 2,423,730 were incorporated in emulsions; GH GOOH
  • This example was l'ePeated using the same hydrosol 1-hydroxy-3-carbethoxy-4-[4-(carboxymethyl)phenylazo]-4- but preswelled with 5 cc. benzene per 100 cc. of hydrosol 15 amylphenoxy)'z'naphthanmde before incorporation of the couplers.
  • (4) OH 700011 In addition to the couplers referred to in Example 1 the NH 1 following additional couplers may be used according to a 00 my invention, this list being illustrative only. V 0
  • EXAMPLE 3 This example illustrates-prevention of viscosity increase of emulsions containing soluble couplers.
  • Example 2 '7 cciof-fge latino-silver, halide emulsionof the composition used in Example 2 and 1.5 cc. of saponin solution.
  • a clear uniform yellow dye image was obtained.
  • the viscosity of the coating mixture was hydroxide solution.
  • the coupler was dissolved the of a hydrosol containing 70% butyl acryl'ate and 30% styrene (solids content was then added and the mixture neutralized with 2.5% citric acid to pH 6.5.
  • the film was exposed behind a step tablet having 20 steps of .15 density difference between steps in a totallength of /2".' The exposure-was predetermined to give after development a silver image in the top layer varying across the scale from a very light'image attheextr'emebuter surface to a heavy deposit almost completely through the top layer. The coating was then processed for 15 minutes at 70 F. in the following developer.
  • Potassium alum 7 do 75 After washing the film and bleaching for 5 minutes in a solution of 50 grams of potassium ferricyanide and 20 grams of potassium bromide in 1 liter of water, the film was fixed for 5 minutes in 30% hypo solution and washed. When the film was dry a section of about 10 microns thickness was cut and examined microscopically at 500 diameters.
  • Example 4 cc..of hydrosol of the composition used "in Example '4 (diluted to 7.5% solids) was added and themixture neutralized with 2.5 citric acid to pH 6.5. The dispersion was then mixed with 18.5 cc. of gelatino-silver halide emulsion, coated and tested as in Example 4. When tested 7 in this way, wandering of the coupler was found to have been reduced to 15% from a value of 30% when no hydrosol was used in the emulsion.
  • the heat of reaction raised the temperature about 8 C.
  • the slurry was stirred vigorously for 1 hour. At no time did the solid go completely into solution.
  • the slurry was then washed into a 12-1. flask with 7.5 1..of water and the aqueoussolution was filtered on a 37-cm. Lapp table-top funnel.
  • the product was washed on the funnel with 9 1. of ethyl alcohol and dried. The yield was 356 g. (102% M. P. 194l97 C.
  • the product was then recrystallized from 9 l. of 97% acetic acid, filtered through the tabletop funnel, washedon the funnel with 900 cc. of acetic acid and two 1800-cc. portions of petroleum ether.
  • nitro compound was filtered 011? and washed on the funnel with 600 cc. of 95 acetic acid followed by 600 cc.
  • the flask was removed from the mantle, placed on a steam bath and equipped with a stirrer and dropping funnel. 14.3 g. ,of freshly prepared o-sulfobenzoicanhydride was dissolved in 100 cc. of hot dry xylene and added rapidly to the vigorously stirred amine solution. The temperature was maintained at 90-95 and the stirring was continued for one hour.
  • the latexes or hydrosols which I use are prepared by'the polymerization of the monomers in aqueous solution.
  • the preferred hydrosol is a three-component polymer of n-butylacrylate, styrene and methacrylamide,
  • hydrosols which I may use are ahydrosol of- 70% butyl acrylate and 30% styrene and a hydrosol of 70% ethyl acrylate and 30% acrylonitrile.
  • emulsion layer 17 for blue-sensitive and contains 2 a, yellow-forming coupler contains 2 a, yellow-forming coupler.
  • the same hydrosol may be used in each emulsion.
  • the emulsions made according to my invention may be used in single layer coatings or in multilayer coatings on supports of glass, cellulose ester, synthetic resins,
  • Thehydrosols may also be used'in-a mixed-grain dispersion, that is, one in which a single emulsion layer contains two or more sets of silver halide grainssensitive to difierent spectral regions.
  • a color-forming photographic emulsion comprising a gelatino-silver halide emulsion continuous. phase containing in said gelatin continuous phase a coupler compound capable of coupling with'the oxidation product of a primary aromatic amino developing agent and also in said gelatin continuous phase a hydrosol of a waterinsoluble synthetic polymer made by emulsion polylayer element comprising a support 10 having thereon hydrosol.
  • Figure 2 is a multilayer photographic element inwhich fthe support 10 is coated with emulsion layers 15, 16 and merization, said polymer including at least anester of an acrylic acid with an aliphatic alcohol havingnot more than 10 carbon atoms.
  • a color-forming photographic emulsion comprising a gelatino-silver halide emulsion continuous phase containing in said gelatin continuous phase a coupler compound capable ofcoupling with the oxidation product of a primary aromatic amino developing agent and containing in its acid form a solubilizing group selected from the class consisting of sulfonic acid, carboxylic acid and hydroxyalkyl groups, and also in said gelatin continuous phase a hydrosol of a water-insoluble syntheticpolymer made by emulsion polymerization,
  • said polymer including a butyl acrylate. 7
  • hydrosol is a hydrosol of a water-insoluble copolymer of n-butyl acrylategstyrene and methacrylamide.
  • hydrosol is a hydrosol of a copolymer of 58.8% by weight n-butyl acrylate, 25.2% by weight styrene and 1 6% by weight acrylamide.
  • halide emulsion a coupler compound capable of coupling with the oxidation product of a primary aromatic amino hydroxyalkyl groups, which comprises dissolving said coupler compound in an alkaline solution, mixing the solution of coupler compound in alkaline solution with a hydrosol of a water-insoluble synthetic polymer made.
  • saidpolymer including at least an ester of an acrylic acid with an aliphatic alcohol having not more than 10 carbon atoms, neutralizing the resulting mixture and mixing it with a gelatino-silver halide emulsion to produce dispersed particles of said hydrosol and said coupler in the emulsion.
  • the method-of incorporating in a gelatino-silver halide emulsion a coupler compound capable of coupling with the oxidation product of a primary aromatic amino developing agent on photographic development, and containing in its acid form a solubilizing group selected from the class consisting of sulfonic acid, carboxylic acid and hydroxyalkyl groups, which comprises dis- 7 solving said couplercompound in an alkaline ethyl alcohol solution, mixing the solution of coupler compound in alkaline ethyl valcohol with a'hydrosol, of a 17, a yellow filter layer 18 being imposed between layers 16 and 17.
  • Emulsion layer 15 is red-sensitive and contains a cyan-forming coupler emulsion layer 7 16 for green-sensitive and contains a magenta-forming coupler water-insoluble copolymer made by emulsion polymerization of n-butyl acrylate, styrene and methacrylamide,
  • the method of incorporating in a gelatino-silver halide emulsion a coupler compound capable of coupling with the oxidation product of a primary aromatic amino developing agent on photographic development, and containing in its acid form a solubilizing group selected from the class consisting of sulfonic acid, carboxylic acid and hydroxyalkyl groups which comprises dissolving said coupler compound in an alkaline ethyl alcohol solution, mixing the solution of coupler compound in alkaline ethyl alcohol with a hydrosol of a water-insoluble copolymer made by emulsion polymerization of n-butyl acrylate and styrene, neutralizing the resulting mixture and mixing it with a gelatino-silver halide emulsion to produce dispersed particles of said hydrosol and said coupler in the emulsion.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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US349348A 1953-04-17 1953-04-17 Photographic emulsions containing couplers and hydrosols Expired - Lifetime US2772163A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
BE528163D BE528163A (en(2012)) 1953-04-17
US349348A US2772163A (en) 1953-04-17 1953-04-17 Photographic emulsions containing couplers and hydrosols
DEE8851A DE965616C (de) 1953-04-17 1954-04-11 Verfahren zur Herstellung eines farbenphotographischen Materials
FR1110268D FR1110268A (fr) 1953-04-17 1954-04-16 Produits photosensibles pour la photographie en couleurs et procédé pour leur préparation
GB11365/54A GB759409A (en) 1953-04-17 1954-04-20 Improvements in photographic emulsions containing colour couplers

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GB (1) GB759409A (en(2012))

Cited By (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2979405A (en) * 1956-06-22 1961-04-11 Gevaert Photo Prod Nv Light-sensitive photographic element containing a 1-hydroxy-2-naphthoic acid anilidecolor coupler
DE1173801B (de) * 1962-06-08 1964-07-09 Eastman Kodak Co Verfahren zur Verbesserung der Farbtiefe von nach dem Umkehrfarbentwicklungsverfahren hergestellten Farbbildern
US3271152A (en) * 1962-09-04 1966-09-06 Eastman Kodak Co Light-sensitive elements for color photography and process therefor
US3655407A (en) * 1969-03-10 1972-04-11 Eastman Kodak Co Method of coating dilute aqueous emulsions
JPS4974538A (en(2012)) * 1972-11-16 1974-07-18
US3844784A (en) * 1971-09-30 1974-10-29 Fuji Photo Film Co Ltd Reversal multi-layer color photographic materials
DE2541230A1 (de) * 1974-09-17 1976-05-26 Eastman Kodak Co Verfahren zur herstellung eines polymer-latex
US3985565A (en) * 1974-07-12 1976-10-12 Eastman Kodak Company Photothermographic, composition using a phenolic leuco dye as a reducing agent
US4120725A (en) * 1976-02-24 1978-10-17 Fuji Photo Film Co., Ltd. Color photographic light-sensitive material
US4133687A (en) * 1977-07-08 1979-01-09 Eastman Kodak Company Photographic elements having hydrophilic colloid layers containing compounds having activator precursors and hydrophobic developing agents uniformly loaded in latex polymer particles
US4197127A (en) * 1976-10-08 1980-04-08 Eastman Kodak Company Photographic silver halide composition and element containing sulfonate copolymers
US4199363A (en) * 1974-09-17 1980-04-22 Eastman Kodak Company Processes for achieving uniform, efficient distribution of hydrophobic materials through hydrophilic colloid layers and loaded latex compositions
US4203716A (en) * 1976-11-24 1980-05-20 Eastman Kodak Company Photographic elements having hydrophilic colloid layers containing hydrophobic addenda uniformly loaded in latex polymer particles
US4214047A (en) * 1979-05-04 1980-07-22 Eastman Kodak Company Photographic elements having hydrophilic colloid layers containing hydrophobic addenda uniformly loaded in latex polymer particles
US4247627A (en) * 1979-10-10 1981-01-27 Eastman Kodak Company Photographic elements having hydrophilic colloid layers containing hydrophobic ultraviolet absorbers uniformly loaded in latex polymer particles
US4304769A (en) * 1974-09-17 1981-12-08 Eastman Kodak Company Process for achieving uniform, efficient distribution of hydrophobic materials through hydrophilic colloid layers and loaded latex compositions
US4368258A (en) * 1977-08-17 1983-01-11 Konishiroku Photo Industry Co., Ltd. Process for preparing impregnated polymer latex compositions
US4512969A (en) * 1974-09-17 1985-04-23 Eastman Kodak Company Compositions containing hydrophobic addenda uniformly loaded in latex polymer particles
US5091296A (en) * 1990-06-26 1992-02-25 Eastman Kodak Company Polymer co-precipitated coupler dispersion
US5254592A (en) * 1991-12-31 1993-10-19 Sterling Drug Inc. Multiply substituted anilines, phenols and pyridines-immunomodulating agents
US5258407A (en) * 1991-12-31 1993-11-02 Sterling Winthrop Inc. 3,4-disubstituted phenols-immunomodulating agents
US5582960A (en) * 1995-02-17 1996-12-10 Eastman Kodak Company Photographic print material
US5594047A (en) * 1995-02-17 1997-01-14 Eastman Kodak Company Method for forming photographic dispersions comprising loaded latex polymers
WO2012014955A1 (ja) 2010-07-30 2012-02-02 富士フイルム株式会社 新規なアゾ化合物、水溶液、インク組成物、インクジェット記録用インク、インクジェット記録方法、インクジェット記録用インクカートリッジ、及びインクジェット記録物
WO2012014954A1 (ja) 2010-07-30 2012-02-02 富士フイルム株式会社 新規なアゾ化合物、水溶液、インク組成物、インクジェット記録用インク、インクジェット記録方法、インクジェット記録用インクカートリッジ、及びインクジェット記録物
EP2455431A1 (en) 2003-10-23 2012-05-23 Fujifilm Corporation Ink and ink set for inkjet recording
EP2712894A1 (en) 2012-09-26 2014-04-02 Fujifilm Corporation Azo compound, aqueous solution, ink composition, ink for inkjet recording, inkjet recording method, ink cartridge for inkjet recording, and inkjet recorded material
US10647661B2 (en) 2017-07-11 2020-05-12 Vertex Pharmaceuticals Incorporated Carboxamides as modulators of sodium channels

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE565490A (en(2012)) * 1957-03-08

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1981102A (en) * 1932-08-10 1934-11-20 Agfa Ansco Corp Photographic material and process of making the same
US2186849A (en) * 1935-08-07 1940-01-09 Agfa Ansco Corp Manufacture of photographic silver halide emulsions
GB524554A (en) * 1939-01-23 1940-08-08 Kodak Ltd Improvements in colour photographic materials
GB540368A (en) * 1939-01-23 1941-10-15 Eastman Kodak Co Improvements in and relating to colour couplers and to colour photographic materialscontaining them
US2269158A (en) * 1937-10-05 1942-01-06 Eastman Kodak Co Color photography
US2322027A (en) * 1940-02-24 1943-06-15 Eastman Kodak Co Color photography
US2361936A (en) * 1939-07-20 1944-11-07 Chromogen Inc Photographic materials and process of manufacturing same
US2376005A (en) * 1943-04-10 1945-05-15 Defender Photo Supply Co Inc Photographic emulsion and process of making same
US2478400A (en) * 1945-08-17 1949-08-09 Eastman Kodak Co Silver halide photographic emulsion with developer and color coupler dispersed therein
US2500052A (en) * 1948-06-02 1950-03-07 Eastman Kodak Co Photographic reversal copying process
US2544903A (en) * 1947-05-03 1951-03-13 Eastman Kodak Co Photosensitive coating containing dyes

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR865774A (fr) * 1939-05-22 1941-06-03 Kodak Pathe Perfectionnements aux produits photographiques et procédés pour les préparer
FR961836A (en(2012)) * 1946-12-11 1950-05-23

Patent Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1981102A (en) * 1932-08-10 1934-11-20 Agfa Ansco Corp Photographic material and process of making the same
US2186849A (en) * 1935-08-07 1940-01-09 Agfa Ansco Corp Manufacture of photographic silver halide emulsions
US2269158A (en) * 1937-10-05 1942-01-06 Eastman Kodak Co Color photography
GB524554A (en) * 1939-01-23 1940-08-08 Kodak Ltd Improvements in colour photographic materials
GB540368A (en) * 1939-01-23 1941-10-15 Eastman Kodak Co Improvements in and relating to colour couplers and to colour photographic materialscontaining them
US2304940A (en) * 1939-01-23 1942-12-15 Eastman Kodak Co Color photography
US2361936A (en) * 1939-07-20 1944-11-07 Chromogen Inc Photographic materials and process of manufacturing same
US2322027A (en) * 1940-02-24 1943-06-15 Eastman Kodak Co Color photography
US2376005A (en) * 1943-04-10 1945-05-15 Defender Photo Supply Co Inc Photographic emulsion and process of making same
US2478400A (en) * 1945-08-17 1949-08-09 Eastman Kodak Co Silver halide photographic emulsion with developer and color coupler dispersed therein
US2544903A (en) * 1947-05-03 1951-03-13 Eastman Kodak Co Photosensitive coating containing dyes
US2500052A (en) * 1948-06-02 1950-03-07 Eastman Kodak Co Photographic reversal copying process

Cited By (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2979405A (en) * 1956-06-22 1961-04-11 Gevaert Photo Prod Nv Light-sensitive photographic element containing a 1-hydroxy-2-naphthoic acid anilidecolor coupler
DE1173801B (de) * 1962-06-08 1964-07-09 Eastman Kodak Co Verfahren zur Verbesserung der Farbtiefe von nach dem Umkehrfarbentwicklungsverfahren hergestellten Farbbildern
US3271152A (en) * 1962-09-04 1966-09-06 Eastman Kodak Co Light-sensitive elements for color photography and process therefor
US3655407A (en) * 1969-03-10 1972-04-11 Eastman Kodak Co Method of coating dilute aqueous emulsions
US3844784A (en) * 1971-09-30 1974-10-29 Fuji Photo Film Co Ltd Reversal multi-layer color photographic materials
JPS4974538A (en(2012)) * 1972-11-16 1974-07-18
US3985565A (en) * 1974-07-12 1976-10-12 Eastman Kodak Company Photothermographic, composition using a phenolic leuco dye as a reducing agent
US4199363A (en) * 1974-09-17 1980-04-22 Eastman Kodak Company Processes for achieving uniform, efficient distribution of hydrophobic materials through hydrophilic colloid layers and loaded latex compositions
DE2541230A1 (de) * 1974-09-17 1976-05-26 Eastman Kodak Co Verfahren zur herstellung eines polymer-latex
US4512969A (en) * 1974-09-17 1985-04-23 Eastman Kodak Company Compositions containing hydrophobic addenda uniformly loaded in latex polymer particles
US4304769A (en) * 1974-09-17 1981-12-08 Eastman Kodak Company Process for achieving uniform, efficient distribution of hydrophobic materials through hydrophilic colloid layers and loaded latex compositions
US4120725A (en) * 1976-02-24 1978-10-17 Fuji Photo Film Co., Ltd. Color photographic light-sensitive material
US4197127A (en) * 1976-10-08 1980-04-08 Eastman Kodak Company Photographic silver halide composition and element containing sulfonate copolymers
US4203716A (en) * 1976-11-24 1980-05-20 Eastman Kodak Company Photographic elements having hydrophilic colloid layers containing hydrophobic addenda uniformly loaded in latex polymer particles
US4133687A (en) * 1977-07-08 1979-01-09 Eastman Kodak Company Photographic elements having hydrophilic colloid layers containing compounds having activator precursors and hydrophobic developing agents uniformly loaded in latex polymer particles
US4368258A (en) * 1977-08-17 1983-01-11 Konishiroku Photo Industry Co., Ltd. Process for preparing impregnated polymer latex compositions
US4214047A (en) * 1979-05-04 1980-07-22 Eastman Kodak Company Photographic elements having hydrophilic colloid layers containing hydrophobic addenda uniformly loaded in latex polymer particles
US4247627A (en) * 1979-10-10 1981-01-27 Eastman Kodak Company Photographic elements having hydrophilic colloid layers containing hydrophobic ultraviolet absorbers uniformly loaded in latex polymer particles
US5279931A (en) * 1990-06-26 1994-01-18 Eastman Kodak Company Polymer co-precipitated coupler dispersion
US5091296A (en) * 1990-06-26 1992-02-25 Eastman Kodak Company Polymer co-precipitated coupler dispersion
US5254592A (en) * 1991-12-31 1993-10-19 Sterling Drug Inc. Multiply substituted anilines, phenols and pyridines-immunomodulating agents
US5258407A (en) * 1991-12-31 1993-11-02 Sterling Winthrop Inc. 3,4-disubstituted phenols-immunomodulating agents
US5582960A (en) * 1995-02-17 1996-12-10 Eastman Kodak Company Photographic print material
US5594047A (en) * 1995-02-17 1997-01-14 Eastman Kodak Company Method for forming photographic dispersions comprising loaded latex polymers
EP2455431A1 (en) 2003-10-23 2012-05-23 Fujifilm Corporation Ink and ink set for inkjet recording
WO2012014955A1 (ja) 2010-07-30 2012-02-02 富士フイルム株式会社 新規なアゾ化合物、水溶液、インク組成物、インクジェット記録用インク、インクジェット記録方法、インクジェット記録用インクカートリッジ、及びインクジェット記録物
WO2012014954A1 (ja) 2010-07-30 2012-02-02 富士フイルム株式会社 新規なアゾ化合物、水溶液、インク組成物、インクジェット記録用インク、インクジェット記録方法、インクジェット記録用インクカートリッジ、及びインクジェット記録物
EP2712894A1 (en) 2012-09-26 2014-04-02 Fujifilm Corporation Azo compound, aqueous solution, ink composition, ink for inkjet recording, inkjet recording method, ink cartridge for inkjet recording, and inkjet recorded material
US10647661B2 (en) 2017-07-11 2020-05-12 Vertex Pharmaceuticals Incorporated Carboxamides as modulators of sodium channels
US11603351B2 (en) 2017-07-11 2023-03-14 Vertex Pharmaceuticals Incorporated Carboxamides as modulators of sodium channels
US12281057B2 (en) 2017-07-11 2025-04-22 Vertex Pharmaceuticals Incorporated Carboxamides as modulators of sodium channels

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GB759409A (en) 1956-10-17
FR1110268A (fr) 1956-02-10
BE528163A (en(2012))
DE965616C (de) 1957-06-13

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