US2311020A - Method of dispersing coloring materials in water swellable colloids - Google Patents

Method of dispersing coloring materials in water swellable colloids Download PDF

Info

Publication number
US2311020A
US2311020A US371776A US37177640A US2311020A US 2311020 A US2311020 A US 2311020A US 371776 A US371776 A US 371776A US 37177640 A US37177640 A US 37177640A US 2311020 A US2311020 A US 2311020A
Authority
US
United States
Prior art keywords
water
gelatin
coupler
solvent
colloid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US371776A
Inventor
Jr David E Bennett
Scheuring S Fierke
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eastman Kodak Co
Original Assignee
Eastman Kodak Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Application granted granted Critical
Publication of US2311020A publication Critical patent/US2311020A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • 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
    • 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
    • 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
    • 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
    • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/924—Significant dispersive or manipulative operation or step in making or stabilizing colloid system
    • Y10S516/928—Mixing combined with non-mixing operation or step, successively or simultaneously, e.g. heating, cooling, ph change, ageing, milling

Definitions

  • This invention relates to a methodof dispersing coloring materials in water swellable photographic colloids and particularly to the manufacture of sensitive photographic emulsions containing couplers.
  • coloring materials such as couplers are mixed with a cellulosic material in the presence of asolvent for the coupler and the cellulosic material and dispersions of the cellulosic material and coupler in gelatin are formed.
  • a solvent for the coupler and the cellulosic material and dispersions of the cellulosic material and coupler in gelatin are formed.
  • First attempts to accomplish the removal of the solvent by spray drying the emulsion containing the coupler produced satisfactory dispersions but resulted in particles of about 4 to 5 microns in diameter and when these were dispersed in gelatin the resulting film was sometimes hazy.
  • an object of the present invention to provide a method for incorporating mixtures of coloring materials and water-insoluble colloids in a water-swellable photographic colloid and maintaining the particle size small enough to prevent haze in the resulting film.
  • a further object is to provide a novel method for incorporating couplers in gelatin emulsions.
  • the coloring material referred to herein may be a dye, a leuco dye or a coupler.
  • coupler we mean the well known type of color forming compound containing a reactive methylene or phenolic hydrom'l group which is reactive to 12 Claims. (oi. -7)
  • the water-swellable or hydrophilic colloid referred to herein may be gelatin or agar.
  • the water-insoluble colloid with which the coloring material is mixed may be a cellulose ester such as collodion or cellulose acetate, a synthetic resin, or a natural gum.
  • a common solvent is used.
  • commonsolvenV we mean a solvent which dissolves both the coupler in its acid or non-water-soluble salt form and the water-insoluble colloid This mixture is dispersed in the presence of a dispersing agent in aqueous solution, the dispersing agent being either gelatin or a material such as a fatty alcohol sulfate.
  • the method used according to our invention may be conveniently illustrated by reference to the incorporation of a coupler in a gelatin emulsion although it is to be understood that the method is equally applicable to the coloration of other coloring materials such as dyes in other water-swellable colloids such as plain photogaphic gelatin.
  • couplers are usually incorporated in it by forming the water-soluble sodium salt of the coupler and mixing this with the gelatin or emulsion. According to our process, it is not necessary to form the water-soluble salt of the coupler but the coupler may be incorporated in the emulsion in its acid form.
  • the coupler is mixed with a waterinsoluble material such as collodion in a common solvent such as butyl acetate. This solution is then added to an aqueous solution containing a dispersing agent such as gelatin or a higher fatty alcohol sulfate. The mixture is then treated to form a dispersion of the solution of the coupler and the water-insoluble colloid solution in the aqueous solution.
  • the suspension formed in this way is heated preferably under vacuum to remove the butyl acetate or other solvent employed in the preparation of solution and coupler and water-insoluble colloid. After the volatile solvent is removed, the suspension of fine particles in the aqueous solution is added to a gelatin emulsion and, after mixing with it, the resulting emulsion is coated.
  • the solvent may be removed after mixture with the gelatin or the solution of coupler and water-insoluble col- Example 1 20 cc. of a commercial collodion emulsion are diluted with 20 cc.
  • Gardinol is a well known dispersing agent of the long chain alcohol sulfate type.
  • the suspension was then recirculated through a small homogenizer for 5 minutes and was vacuum distilled to remove solvents employed in the preparation of collodion emulsion and the butyl acetate which was added. Prior to the removal of the solvent by vacuum, small amounts of N-octyl alcohol were added to prevent foaming. After the volatile solvents were removed, the suspension of the fine particles in the Gardinol solution was added to 50 cc. of a 6% gelatin solution and the samples were coated.
  • a gelatin solution can be used instead of the Gardinol solution.
  • the whole mixture is heated on a steam bath at 100 C. with constant stirring to evaporate all of the butyl acetate and some of the water. At the end of the evaporation process the volume has been reduced to about 300 cc.
  • This dispersion of cellulose nitrate particles containing the coupler is added to 1000 cc. of a red-sensitive gelatino-silver halide emulsion.
  • the resulting emulsion is coated on a suitable support.
  • a yellow filter layer is then coated on the emulsion, consisting of tartrazine in gelatin.
  • the top layer consists of a green-sensitive silver halide gelatin emulsion to which has been added a cellulose nitrate dispersion made as described in the preceding paragraph, but using as the coupler a mixture yielding an orange-red dye upon development.
  • Suitable couplers for this purpose are n-propyl-p-benzoyl acetoamino benzene sulfonate and 2-cyanoacetylnaphthalene-sulfon-N-methyl anilide. These couplers are used in the amount of 5 grams each and producing an orange red dye upon development in a coupling developer. This emulsion is coated as the top layer to produce a two-layer sensitive material.
  • the film may contain a yellow dye throughout the emulsions which is removable during processing either by virtue of its solubility or its susceptibility to a chemical action of one of the processing baths.
  • the method described in the present specification offers advantages over the spray drying procedure from the standpoint both of simplicity and of increased yield.
  • the method is also less hazardous and produces dispersed particles of an average size of one micron or less.
  • the method of dispersing a coloring material in a water-swellable photographic colloid which comprises dissolving the coloring material and a water-insoluble colloid in a common solvent which is a non-solvent for the water-swellable colloid, emulsifying the solution in an aqueous solution of a dispersing agent, removing the solvent from the emulsion by evaporation while the particles of coloring material and waterinsoluble colloid are in a dispersed form and suspending the coloring material and waterinsoluble colloid in finely divided form in the water-swellable colloid.
  • the method of dispersing a coloring material in a water-swellable photographic colloid which comprises dissolving the coloring material and a water-insoluble colloid in a common solvent which is a non-solvent for the water-swellable colloid, emulsifying the solution in thewaterswellable colloid, and removing the solvent by evaporation while the particles of coloring material and water-insoluble colloid are in a dispersed form, thereby leaving the coloring material and water-insoluble colloid suspended in finelydivided form in the water-swellable colloid.
  • the method of dispersing a coloring material in gelatin which comprises dissolving the coloring material and a water-insoluble colloid in a common solvent which is a non-solvent for the gelatin, emulsifying the solution in water containing a dispersing agent, and removing the solvent by evaporation while the particles of coloring material and water-insoluble colloid are in a dispersed form, thereby leaving the coloring material and water-insoluble colloid suspended in finely-divided form in the aqueous solution, and mixing it with the gelatin.
  • the method of dispersing a coupler in gelatin which comprises dissolving the coupler and a water-insoluble colloid in a common solvent which is a non-solvent for the gelatin, emulsifying the solution in water containing a dispersing agent, and removing the solvent by evaporation while the particles of coupler and water-insoluble colloid are in a dispersed form, thereby leaving the coupler and water-insoluble colloid suspended in finely-divided form in the aqueous solution, and mixing it with the gelatin.
  • the method of dispersing a coloring material in gelatin which comprises dissolving the coloring material and cellulose ester in a common solvent which is a non-solvent for the gelatin, emulsifying the solution in water containing a dispersing agent and removing the solvent by evaporation whilethe particles of coloring material and cellulose ester are in a. dispersed form, thereby leaving the coloring material and cellulose ester suspended in finely-divided form in the aqueous solution, and mixing it with the gelatin.
  • the method of dispersing a coupler in gelatin which comprises dissolving the coupler and collodion in a common solvent which is a nonsolvent for the gelatin, emulsifying the solution in water containing a dispersing agent, and removing the solvent by evaporation while the particles or coupler and collodion are in a dispersed form, thereby leaving the coupler and collodion suspended in finely-divided form in the aqueous solution, and mixing it with the gelatin.
  • the method of dispersing a coupler in gelatin which comprises dissolving the coupler and a water-insoluble colloid in a common solvent which is a non-solvent for the gelatin, emulsifying the solution in water containing a dispersing agent, and removing the solvent by evaporation under vacuum while the particles of coupler and water-insoluble colloid are in a dispersed form, thereby leaving the coupler and water-insoluble colloid suspended in finely-divided form in the aqueous solution, and mixing it with the gelatin.
  • the method of dispersing a coupler in gelatin which comprises dissolving the coupler and a water-insoluble colloid in a common solvent which is a non-solvent; for the gelatin, emulsifying the solution in water containing a dispersing agent, and removing the solvent by vacuum distillation while the particles of coupler and waterinsoluble colloid are in a dispersed form, thereby leaving the coupler and water-insoluble colloid suspended in finely-divided form in the aqueous solution, and mixing it with the gelatin.
  • the method of dispersing a coupler in a gelatino-silver halide emulsion which comprises dissolving the coupler and a water-insoluble colloid in a common solvent which is a non-solvent for the gelatin of the emulsion, emulsifying the solution in water containing a dispersing agent and removing the solvent by evaporation under vacuum while the particles of the coupler and water-insoluble colloid are in a dispersed form, thereby leaving the coupler and water-insoluble colloid suspended in finely divided form in the aqueous solution and mixing said solution with the gelatino silver halide emulsion.

Landscapes

  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)

Description

Patented Feb. 16, 1943 METHQD F DISPERSING COLORING MATE- BIALS IN WATER SWELLABLE COLLOIDS David E. Bennett, Jr., and Scheuring s. Fierke, Rochester, N. Y., asslgnora to Eastman Kodak Company, Rochester, N. Y., a corporation of v New Jersey No Dra. Application December 26, 1940. Se-
rial No. 371,776. In Great Britain December This invention relates to a methodof dispersing coloring materials in water swellable photographic colloids and particularly to the manufacture of sensitive photographic emulsions containing couplers.
There have been many proposals of methods for incorporating coloring materials such as dyes or color forming compounds in photographic gelatin, particularly sensitive photographic emulsions. When materials such as couplers are incorporated in photographic emulsions, it is usually desirable that the couplers do not difiuse from the layers in which they are incorporated, especially when such layers are used in multilayer coatings. One method of incorporating coloring materials in photographic gelatin layers is described in Mannes & Godowsky U. S. application Serial No. 314,689, filed January 19, 1940. According to the method described in that application, coloring materials such as couplers are mixed with a cellulosic material in the presence of asolvent for the coupler and the cellulosic material and dispersions of the cellulosic material and coupler in gelatin are formed. In preparing these dispersions, it is necessary to remove a part or all of the solvent used to disssolve the cellulosic material and the coupler. First attempts to accomplish the removal of the solvent by spray drying the emulsion containing the coupler produced satisfactory dispersions but resulted in particles of about 4 to 5 microns in diameter and when these were dispersed in gelatin the resulting film was sometimes hazy.
It is, therefore, an object of the present invention to provide a method for incorporating mixtures of coloring materials and water-insoluble colloids in a water-swellable photographic colloid and maintaining the particle size small enough to prevent haze in the resulting film. A further object is to provide a novel method for incorporating couplers in gelatin emulsions. Other objects will appear from the following description of our invention.
These objects are accomplished by dispersing the solution of the coloring material and the water-insoluble colloid in an aqueous vehicle, preferably water or dilute gelatin solution, and removing the solvent from the aqueous dispersion while the particles of coloring material and water-insoluble colloid are in dispersed form.
The coloring material referred to herein may be a dye, a leuco dye or a coupler. By coupler we mean the well known type of color forming compound containing a reactive methylene or phenolic hydrom'l group which is reactive to 12 Claims. (oi. -7)
form a dye in the presence of the oxidized form of primary aromatic amino coupling developers.
The water-swellable or hydrophilic colloid referred to hereinmay be gelatin or agar.
The water-insoluble colloid with which the coloring material is mixed may be a cellulose ester such as collodion or cellulose acetate, a synthetic resin, or a natural gum.
lln preparing the solutions of the coloring material and the water-insoluble colloid, a common solvent is used. By "commonsolvenV we mean a solvent which dissolves both the coupler in its acid or non-water-soluble salt form and the water-insoluble colloid This mixture is dispersed in the presence of a dispersing agent in aqueous solution, the dispersing agent being either gelatin or a material such as a fatty alcohol sulfate.
The method used according to our invention may be conveniently illustrated by reference to the incorporation of a coupler in a gelatin emulsion although it is to be understood that the method is equally applicable to the coloration of other coloring materials such as dyes in other water-swellable colloids such as plain photogaphic gelatin.
Since gelatin is a hydrophilic colloid, couplers are usually incorporated in it by forming the water-soluble sodium salt of the coupler and mixing this with the gelatin or emulsion. According to our process, it is not necessary to form the water-soluble salt of the coupler but the coupler may be incorporated in the emulsion in its acid form. The coupler is mixed with a waterinsoluble material such as collodion in a common solvent such as butyl acetate. This solution is then added to an aqueous solution containing a dispersing agent such as gelatin or a higher fatty alcohol sulfate. The mixture is then treated to form a dispersion of the solution of the coupler and the water-insoluble colloid solution in the aqueous solution. This may be done by passing the mixture through a small homogen-' izer. The suspension formed in this way is heated preferably under vacuum to remove the butyl acetate or other solvent employed in the preparation of solution and coupler and water-insoluble colloid. After the volatile solvent is removed, the suspension of fine particles in the aqueous solution is added to a gelatin emulsion and, after mixing with it, the resulting emulsion is coated. As an alternative, the solvent may be removed after mixture with the gelatin or the solution of coupler and water-insoluble col- Example 1 20 cc. of a commercial collodion emulsion are diluted with 20 cc. of normal butyl acetate and 1.5 grams or 1,4-di-(w-benzoylacetamino)-benzene. This solution was then added to 100 cc. of a 1'2 solution of Gardinol WA in water. Gardinol is a well known dispersing agent of the long chain alcohol sulfate type. The suspension was then recirculated through a small homogenizer for 5 minutes and was vacuum distilled to remove solvents employed in the preparation of collodion emulsion and the butyl acetate which was added. Prior to the removal of the solvent by vacuum, small amounts of N-octyl alcohol were added to prevent foaming. After the volatile solvents were removed, the suspension of the fine particles in the Gardinol solution was added to 50 cc. of a 6% gelatin solution and the samples were coated.
Instead of the Gardinol solution, a gelatin solution can be used.
The whole mixture is heated on a steam bath at 100 C. with constant stirring to evaporate all of the butyl acetate and some of the water. At the end of the evaporation process the volume has been reduced to about 300 cc. This dispersion of cellulose nitrate particles containing the coupler is added to 1000 cc. of a red-sensitive gelatino-silver halide emulsion. The resulting emulsion is coated on a suitable support. A yellow filter layer is then coated on the emulsion, consisting of tartrazine in gelatin.
The top layer consists of a green-sensitive silver halide gelatin emulsion to which has been added a cellulose nitrate dispersion made as described in the preceding paragraph, but using as the coupler a mixture yielding an orange-red dye upon development. Suitable couplers for this purpose are n-propyl-p-benzoyl acetoamino benzene sulfonate and 2-cyanoacetylnaphthalene-sulfon-N-methyl anilide. These couplers are used in the amount of 5 grams each and producing an orange red dye upon development in a coupling developer. This emulsion is coated as the top layer to produce a two-layer sensitive material.
In place of the tartrazine filter dye, the film may contain a yellow dye throughout the emulsions which is removable during processing either by virtue of its solubility or its susceptibility to a chemical action of one of the processing baths.
The method described in the present specification offers advantages over the spray drying procedure from the standpoint both of simplicity and of increased yield. The method is also less hazardous and produces dispersed particles of an average size of one micron or less.
The examples included in the present specification are illustrative only and it is to be understood that our invention is limited only by the scope of the appended claims.
We claim:
1. The method of dispersing a coloring material in a water-swellable photographic colloid which comprises dissolving the coloring material and a water-insoluble colloid in a common solvent which is a non-solvent for the water-swellable colloid, emulsifying the solution in an aqueous solution of a dispersing agent, removing the solvent from the emulsion by evaporation while the particles of coloring material and waterinsoluble colloid are in a dispersed form and suspending the coloring material and waterinsoluble colloid in finely divided form in the water-swellable colloid.
2. The method of dispersing a coloring material in a water-swellable photographic colloid, which comprises dissolving the coloring material and a water-insoluble colloid in a common solvent which is a non-solvent for the water-swellable colloid, emulsifying the solution in thewaterswellable colloid, and removing the solvent by evaporation while the particles of coloring material and water-insoluble colloid are in a dispersed form, thereby leaving the coloring material and water-insoluble colloid suspended in finelydivided form in the water-swellable colloid.
3. The method of dispersing a coloring material in gelatin, which comprises dissolving the coloring material and a water-insoluble colloid in a common solvent which is a non-solvent for the gelatin, emulsifying the solution in water containing a dispersing agent, and removing the solvent by evaporation while the particles of coloring material and water-insoluble colloid are in a dispersed form, thereby leaving the coloring material and water-insoluble colloid suspended in finely-divided form in the aqueous solution, and mixing it with the gelatin.
4. The method of dispersing a coupler in gelatin, which comprises dissolving the coupler and a water-insoluble colloid in a common solvent which is a non-solvent for the gelatin, emulsifying the solution in water containing a dispersing agent, and removing the solvent by evaporation while the particles of coupler and water-insoluble colloid are in a dispersed form, thereby leaving the coupler and water-insoluble colloid suspended in finely-divided form in the aqueous solution, and mixing it with the gelatin.
5. The method of dispersing a coloring material in gelatin, which comprises dissolving the coloring material and cellulose ester in a common solvent which is a non-solvent for the gelatin, emulsifying the solution in water containing a dispersing agent and removing the solvent by evaporation whilethe particles of coloring material and cellulose ester are in a. dispersed form, thereby leaving the coloring material and cellulose ester suspended in finely-divided form in the aqueous solution, and mixing it with the gelatin.
6. The method of dispersing a coupler in gelatin, which comprises dissolving the coupler and collodion in a common solvent which is a nonsolvent for the gelatin, emulsifying the solution in water containing a dispersing agent, and removing the solvent by evaporation while the particles or coupler and collodion are in a dispersed form, thereby leaving the coupler and collodion suspended in finely-divided form in the aqueous solution, and mixing it with the gelatin.
7. The method of dispersing a coupler in gelatin, which comprises dissolving the coupler and a water-insoluble colloid in a common solvent which is a non-solvent for the gelatin, emulsifying the solution in water containing a dispersing agent, and removing the solvent by evaporation under vacuum while the particles of coupler and water-insoluble colloid are in a dispersed form, thereby leaving the coupler and water-insoluble colloid suspended in finely-divided form in the aqueous solution, and mixing it with the gelatin.
8. The method of dispersing a coupler in gelatin, which comprises dissolving the coupler and a water-insoluble colloid in a common solvent which is a non-solvent; for the gelatin, emulsifying the solution in water containing a dispersing agent, and removing the solvent by vacuum distillation while the particles of coupler and waterinsoluble colloid are in a dispersed form, thereby leaving the coupler and water-insoluble colloid suspended in finely-divided form in the aqueous solution, and mixing it with the gelatin.
9. The method of claim 4, in which the solvent is an ester.
10. The method of claim 4, in which the solvent is an ester of a lower fatty alcohol and a lower fatty acid.
11. The method of claim 7, in which a foampreventing agent is added to the emulsion prior to removal of the solvent.
12. The method of dispersing a coupler in a gelatino-silver halide emulsion which comprises dissolving the coupler and a water-insoluble colloid in a common solvent which is a non-solvent for the gelatin of the emulsion, emulsifying the solution in water containing a dispersing agent and removing the solvent by evaporation under vacuum while the particles of the coupler and water-insoluble colloid are in a dispersed form, thereby leaving the coupler and water-insoluble colloid suspended in finely divided form in the aqueous solution and mixing said solution with the gelatino silver halide emulsion.
DAVID E. BENNETT, JR. SCHEURING S. FIERKE.
US371776A 1939-01-23 1940-12-26 Method of dispersing coloring materials in water swellable colloids Expired - Lifetime US2311020A (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
GB236780X 1939-01-23
GB281239X 1939-12-28
GB291239X 1939-12-29
GB190140X 1940-01-19
GB230240X 1940-02-23

Publications (1)

Publication Number Publication Date
US2311020A true US2311020A (en) 1943-02-16

Family

ID=27516200

Family Applications (4)

Application Number Title Priority Date Filing Date
US314689A Expired - Lifetime US2304940A (en) 1939-01-23 1940-01-19 Color photography
US363012A Expired - Lifetime US2318788A (en) 1939-01-23 1940-10-26 Incorporation of couplers in nongelatin emulsions
US371776A Expired - Lifetime US2311020A (en) 1939-01-23 1940-12-26 Method of dispersing coloring materials in water swellable colloids
US371650A Expired - Lifetime US2279406A (en) 1939-01-23 1940-12-26 Color process using cellulose ester emulsions

Family Applications Before (2)

Application Number Title Priority Date Filing Date
US314689A Expired - Lifetime US2304940A (en) 1939-01-23 1940-01-19 Color photography
US363012A Expired - Lifetime US2318788A (en) 1939-01-23 1940-10-26 Incorporation of couplers in nongelatin emulsions

Family Applications After (1)

Application Number Title Priority Date Filing Date
US371650A Expired - Lifetime US2279406A (en) 1939-01-23 1940-12-26 Color process using cellulose ester emulsions

Country Status (6)

Country Link
US (4) US2304940A (en)
BE (1) BE440854A (en)
CH (1) CH236780A (en)
FR (3) FR51566E (en)
GB (2) GB540525A (en)
NL (2) NL65241C (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2534654A (en) * 1946-01-11 1950-12-19 Polaroid Corp Ultraviolet absorbing filter
US4349455A (en) * 1979-03-27 1982-09-14 Fuji Photo Film Co., Ltd. Emulsification process

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2415382A (en) * 1944-03-31 1947-02-04 Du Pont Photographic elements including hydrophilic color formers
US2454043A (en) * 1944-04-04 1948-11-16 Ilford Ltd Gelatino-silver halide photographic elements containing higher fatty alcohols
US2527262A (en) * 1944-10-30 1950-10-24 Ilford Ltd Photographic layers containing gelatin-anion soap complexes and their preparation
GB585758A (en) * 1944-10-30 1947-02-24 John Alfred Henry Hart Improvements in or relating to the production of photographic emulsions
US2527267A (en) * 1944-10-30 1950-10-24 Ilford Ltd Photographic layers containing gelatin-sulfonic acid complexes, and their preparation
US2527268A (en) * 1944-10-30 1950-10-24 Ilford Ltd Production of photographic emulsions
US2576850A (en) * 1945-04-26 1951-11-27 Du Pont Gelling of polymeric compounds
US2428208A (en) * 1945-06-20 1947-09-30 Eastman Kodak Co Dichromate bleach bath containing a wetting agent and method of bleaching therewith
US2478400A (en) * 1945-08-17 1949-08-09 Eastman Kodak Co Silver halide photographic emulsion with developer and color coupler dispersed therein
US2528496A (en) * 1946-04-30 1950-11-07 Chalkley Lyman Photosensitive leucocyanide composition
US2571725A (en) * 1946-08-15 1951-10-16 Eastman Kodak Co Eliminating stain in photographic color material
US2577127A (en) * 1946-11-23 1951-12-04 Du Pont Photographic element with colloid layer containing color former and nonionic wettingagent
US2565418A (en) * 1947-08-13 1951-08-21 Eastman Kodak Co Method of preparing photographic silver halide emulsions
BE484580A (en) * 1947-08-29
BE528163A (en) * 1953-04-17
BE543744A (en) * 1954-12-20
US2843489A (en) * 1955-07-29 1958-07-15 Eastman Kodak Co Mixed packet photographic emulsions with polyvinyl resin continuous phase
BE551312A (en) * 1955-10-01
US2870012A (en) * 1955-12-23 1959-01-20 Eastman Kodak Co Microdispersions of photographic color couplers
GB852922A (en) * 1957-09-04 1960-11-02 Gen Aniline & Film Corp Color formers containing a m-alkylphenoxyacyl group
GB864060A (en) * 1957-11-01 1961-03-29 Gen Aniline & Film Corp Mixed grain photographic emulsions
US3033680A (en) * 1958-01-13 1962-05-08 Eastman Kodak Co Plasticized gelating compositions
CA684233A (en) * 1959-05-25 1964-04-14 C. Haas Howard Photographic products and processes
JPS5448538A (en) * 1977-09-12 1979-04-17 Konishiroku Photo Ind Co Ltd Color photographic material
JPS56126830A (en) * 1980-03-11 1981-10-05 Konishiroku Photo Ind Co Ltd Silver halide photographic sensitive material
IT1197427B (en) * 1982-05-14 1988-11-30 Gian Franco Menicucci METHOD FORMULATION METHOD FOR DENTAL AND COMPLEX USE OF ALLOYS SO OBTAINED
US4725529A (en) 1985-04-30 1988-02-16 Konishiroku Photo Industry Co., Ltd. Developing inhibitor arrangment in light-sensitive silver halide color photographic materials
EP0204530B1 (en) 1985-05-31 1991-09-11 Konica Corporation Method for forming direct positive color image
AU591540B2 (en) 1985-12-28 1989-12-07 Konishiroku Photo Industry Co., Ltd. Method of processing light-sensitive silver halide color photographic material
US5700608A (en) * 1995-07-31 1997-12-23 Eastman Kodak Company Process for making photographic emulsions and photographic elements and emulsions containing latent image forming units internally containing sensitizing dye

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2534654A (en) * 1946-01-11 1950-12-19 Polaroid Corp Ultraviolet absorbing filter
US4349455A (en) * 1979-03-27 1982-09-14 Fuji Photo Film Co., Ltd. Emulsification process

Also Published As

Publication number Publication date
NL65241C (en)
FR57149E (en) 1952-12-15
FR51566E (en) 1943-02-05
FR951528A (en) 1949-10-27
CH236780A (en) 1945-03-15
GB540525A (en) 1941-10-20
US2318788A (en) 1943-05-11
GB540368A (en) 1941-10-15
BE440854A (en)
US2304940A (en) 1942-12-15
US2279406A (en) 1942-04-14
NL63641C (en)

Similar Documents

Publication Publication Date Title
US2311020A (en) Method of dispersing coloring materials in water swellable colloids
US2322027A (en) Color photography
US2835579A (en) N-alkyl and acylphenol coupler solvents for color photography
US3912517A (en) Method of incorporating photographic ingredients into hydrophilic colloids
US2322006A (en) Photographic filter and antihalation layer
US4006025A (en) Process for dispersing sensitizing dyes
US2322005A (en) Photographic bleach-out layer
EP0075231B1 (en) Process for providing a matt surface on a photographic material and photographic material provided with such matt surface
EP0167081B1 (en) Silver halide photographic recording material
DE69013708T2 (en) Filter dyes for photographic elements.
US2327828A (en) Colloidal carbon antihalation layer
US3469987A (en) Method of spectrally sensitizing photographic silver halide emulsions
DE1622274A1 (en) Photographic material with improved lubricity
JPS6137609B2 (en)
EP0136506B1 (en) Photographic silver halide recording material
DE2409689A1 (en) PHOTOGRAPHIC SENSITIVE MATERIALS
JPS5950695B2 (en) Manufacturing process of aqueous polymer latex composition
US2533514A (en) Photographic emulsions containing color couplers and amide coupler solvents
US2271234A (en) Colloidal carbon antihalation layer
DE1805880A1 (en) Process for the preparation of a halogen silver emulsion having a color coupler dispersed therein
US2368287A (en) Photographic element and method of making it
DE2516967A1 (en) PHOTOGRAPHIC SENSITIVE SILVER HALOGENIDE MATERIAL
US2478400A (en) Silver halide photographic emulsion with developer and color coupler dispersed therein
US2276323A (en) Photographic silver halide emulsion
DE3408329A1 (en) PHOTOGRAPHIC LIGHT-SENSITIVE SILVER HALOGENIDE MATERIAL