US2310226A - Process for the manufacture of photographic materials - Google Patents
Process for the manufacture of photographic materials Download PDFInfo
- Publication number
- US2310226A US2310226A US346435A US34643540A US2310226A US 2310226 A US2310226 A US 2310226A US 346435 A US346435 A US 346435A US 34643540 A US34643540 A US 34643540A US 2310226 A US2310226 A US 2310226A
- Authority
- US
- United States
- Prior art keywords
- solution
- dye
- water
- forming
- layer
- 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
Links
- 238000000034 method Methods 0.000 title description 20
- 239000000463 material Substances 0.000 title description 8
- 238000004519 manufacturing process Methods 0.000 title description 3
- 239000000243 solution Substances 0.000 description 34
- 239000000126 substance Substances 0.000 description 21
- 238000009740 moulding (composite fabrication) Methods 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000000975 dye Substances 0.000 description 15
- 239000000839 emulsion Substances 0.000 description 14
- 230000003165 hydrotropic effect Effects 0.000 description 13
- -1 silver halide Chemical class 0.000 description 13
- 229910052709 silver Inorganic materials 0.000 description 12
- 239000004332 silver Substances 0.000 description 12
- 108010010803 Gelatin Proteins 0.000 description 8
- 229920000159 gelatin Polymers 0.000 description 8
- 239000008273 gelatin Substances 0.000 description 8
- 235000019322 gelatine Nutrition 0.000 description 8
- 235000011852 gelatine desserts Nutrition 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000011230 binding agent Substances 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000000987 azo dye Substances 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- LWEAHXKXKDCSIE-UHFFFAOYSA-M 2,3-di(propan-2-yl)naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S([O-])(=O)=O)=C(C(C)C)C(C(C)C)=CC2=C1 LWEAHXKXKDCSIE-UHFFFAOYSA-M 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VJGYRGWNECLPCM-UHFFFAOYSA-N 4-amino-2-benzylbenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C(CC=2C=CC=CC=2)=C1 VJGYRGWNECLPCM-UHFFFAOYSA-N 0.000 description 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229940053200 antiepileptics fatty acid derivative Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001045 blue dye Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- OBNCKNCVKJNDBV-UHFFFAOYSA-N ethyl butyrate Chemical compound CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000005404 monopole Effects 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- WBHHMMIMDMUBKC-QJWNTBNXSA-N ricinoleic acid Chemical compound CCCCCC[C@@H](O)C\C=C/CCCCCCCC(O)=O WBHHMMIMDMUBKC-QJWNTBNXSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- PYODKQIVQIVELM-UHFFFAOYSA-M sodium;2,3-bis(2-methylpropyl)naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 PYODKQIVQIVELM-UHFFFAOYSA-M 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
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
- 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
- G03C7/3885—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 solvent
-
- 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
Definitions
- This invention relates to color photographic materials and has for its object the provision of processes for the manufacture of photographic colloids containing dye-forming substances which can be used to form filter layers or as silver halide emulsion layers especially in color photographic materials.
- the process is applicable to waterinsoluble dye-forming substances, true aqueous solutions of which can be obtained by means of hydrotropic substances.
- the dye-forming substances may be of different kinds and may, for example, be used for the formation of azo dyes, vat dyes and in the process of so-called color developrnent.
- insoluble dye components are incorporated into photographic layers by forming a true aqueous solution of the dye component with the aid of a sufficient quantity of a wetting agent with hydrotropic properties, thereaftermixing the solution thus obtainedwith a binding agent solution or with an emulsion, for instance, a silver halide emulsion, using the final product to make a layer.
- any insoluble dye A component that can be made to form true aqueous solutions by means of hydrotropic agents is suitable.
- preparation of the dye component solutions can be still further facilitated by using in addition to the hydrotropic substances organic solvents that are miscible with water, such as methyl alcohols, ethyl alcohol, acetone, dioxane, pyridine or diacetine in small quantities.
- hydrotropic Wetting agents is used inthis specification to denote salts of a polar constitution such as the alkali salts of alkylated or aralkylated naphthalene sulphomc acids, or of benzyl sulphanilic acid, or of other organic acids such as enumerated by Ullman in Encyclopaedie der Technischen Chemie, 2nd edition, vol. E, page 808, which are capable of multiplying the water solubility of difficult. soluble compounds, especially such organic compounds.
- hydrotropic wetting agents enumerated as examples in my co-pending patent application No. 14,068/38 may be used. These include the sulphuric acid ester of the butyric ester of ricinolic acid (known as Avirol AH, made by H. Th.
- BoehmeAvirol is a registered trademark
- Monopol Soap the sodium salt of sulphonated castor oil
- Sapamine MS a special basic fatty acid amide manufactured by the Society for'Chemical Industry in Basle Sapamine is a registered trade-mark
- Nekal BX a special alkylated naphthalene sulphonic acid manufactured by the I. G. Far-benindustrie A. G.Nekal is a registered trademark).
- Nekal AEM a mixture of the sodium salt of a special alkylated naphthalene sulphonic acid with glue manufactured by I. G. Maschinenindustrie A. G
- Igepones special fatty acid derivatives manufactured by the I. G. Maschinenindustrie A. G.- Igepone is a registered trade-mark
- gelatin containing the dye component is thereafter thoroughly mixed with an equal amount of silver halide gelatin emulsion to yield a light-sensitive emulsion suificient to cover 0.3 sq. metre,
- the light-sensitive layer containing the dye component may then be used for the. production of a dye-image in a multi-layer material.
- the process employed for obtaining the dyeimage may be the known process of the local destrustion of the dye component depending on a silver image produced in the layer, and afterwards forming an azo dye from the dye component remaining in the layer; or converting the dye component to an azo dye uniformly throughout the layer and afterwards destroying the dye locally in dependence on the silver image.
- diazotized sulphanilic acid for instance, the dinaphthole yields an orange azo dye.
- the layer maybe used in a material for the process of so-called color development in which case the dinaphthole serves as a coupling component for color development yielding a blue dye with the ordinary colo'r developers.
- Silver halide emulsions prepared according to the process described above can be sensitized in the usual manner by adding sensitizers at any stage of their preparation.
- a multi-layer material for color photographic purposes can be prepared by superimposing silver halide emulsions prepared in accordance with the invention.
- a process for producing layers for photographic purposes which comprises dissolving a dye-forming substance which is substantially insoluble in water in a solution comprising water and a quantity of a hydrotropic substance sufficient to form a true solution, incorporating a binding agent in said solution and then forming said solution into a layer.
- a process for producing layers for photographic piu'poses which comprises dissolving a dye-forming substance which is substantially insoluble in water in a solution comprising water and a quantity of a hydrotropic substance sumcient to form a true solution, incorporating a colloid solution in said solution and then form-- ing said solution'into a layer.
- A' process for producing layers for photographic purposes which comprises dissolving a dye-forming substance which is substantially insoluble in water in a solution comprising water and a quantity of a hydrotropic substance sufficient to form a true solution, adding a silver halide emulsion 'to said solution and then forming said solution into a layer.
- a process for producing layers for photographic purposes which comprises dissolving a dye-forming substance which is substantially insoluble in water in a solution comprising water and a quantity of a hydrotropic substance sufiicient to form a true solution, incorporating a ,bindingagent and a light-sensitive silver halide insaid solution and then forming said solution into a layer.
- a process for producing layers for photographic purposes which comprises dissolving a dye-forming substance which is substantially insoluble in water in a solution comprising water and a quantity of a hydrotropic substance sufiiv cient to form a true solution, adding a silver halide gelatin emulsion to said solution and then forming said emulsion containing the dye-forming substance into a layer.
- a process for producing layers for photographic purposes which comprises dissolving a dye-forming substance which is substantially insoluble in water in a solution comprising water and a quantity of a hydrotropic substance sufflcient to form a true solution, incorporating a silver halide gelatin emulsion and a sensitizing dye in said solution and then forming said solution into a color sensitized light-sensitive layer.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Description
, atented Feb. 9, 1943 PROCESS FOR THE PHOTUGRAP jlBla Gaspar, Hollywood, Calif., assignor to Chromogen, Nevada Incorporated, a corporation of No Drawing. Application July 19, 1940, Serial No.
346,435. In Great tain July 19, 1939 6 Glaims.
This invention relates to color photographic materials and has for its object the provision of processes for the manufacture of photographic colloids containing dye-forming substances which can be used to form filter layers or as silver halide emulsion layers especially in color photographic materials.
The process described in my prior patent application Serial Number 267,905, filed April 14, 1939, consists in the preparation of true aqueous solutions of dyes insoluble in water with the aid of wetting agents with hydrotropic properties. The solutions thus obtained are then mixed with binding agent solutions or with emulsions of binding agents, for instance, with gelatin solutions or with silver halide gelatin emulsions.
In prior patents the inventor described photographic materials for color photographic purposes containing dye components and also described processes for obtaining multicolor photographic pictures with such materials. As described in these patents, in general, insoluble components have to be converted into soluble derivatives thereof in order to facilitate'their incorporation in. the layer.
It is an object of the present invention to provide a process for incorporating water-insoluble dye-forming substances into photographic emulsions without the necessity of converting the insoluble dye-forming substances intosoluble derivatives. The process is applicable to waterinsoluble dye-forming substances, true aqueous solutions of which can be obtained by means of hydrotropic substances. The dye-forming substances may be of different kinds and may, for example, be used for the formation of azo dyes, vat dyes and in the process of so-called color developrnent.
According to the present invention, therefore, insoluble dye components are incorporated into photographic layers by forming a true aqueous solution of the dye component with the aid of a sufficient quantity of a wetting agent with hydrotropic properties, thereaftermixing the solution thus obtainedwith a binding agent solution or with an emulsion, for instance, a silver halide emulsion, using the final product to make a layer.
For carrying out this process any insoluble dye A component that can be made to form true aqueous solutions by means of hydrotropic agents is suitable. In many cases the preparation of the dye component solutions can be still further facilitated by using in addition to the hydrotropic substances organic solvents that are miscible with water, such as methyl alcohols, ethyl alcohol, acetone, dioxane, pyridine or diacetine in small quantities.
The term, "hydrotropic Wetting agents is used inthis specification to denote salts of a polar constitution such as the alkali salts of alkylated or aralkylated naphthalene sulphomc acids, or of benzyl sulphanilic acid, or of other organic acids such as enumerated by Ullman in Encyclopaedie der Technischen Chemie, 2nd edition, vol. E, page 808, which are capable of multiplying the water solubility of difficult. soluble compounds, especially such organic compounds.
In practicing the process of the present invention, the hydrotropic wetting agents enumerated as examples in my co-pending patent application No. 14,068/38 may be used. These include the sulphuric acid ester of the butyric ester of ricinolic acid (known as Avirol AH, made by H. Th. BoehmeAvirol is a registered trademark), the sodium salt of sulphonated castor oil (known as Monopol Soap, manufactured by Chemische Fabrik Stockhausen & Co.-Monopol is a registered trade-mark), Sapamine MS (a special basic fatty acid amide manufactured by the Society for'Chemical Industry in Basle Sapamine is a registered trade-mark) and Nekal BX (a special alkylated naphthalene sulphonic acid manufactured by the I. G. Far-benindustrie A. G.Nekal is a registered trademark).
In addition to these, compounds acting similarly may also be used, such as Nekal AEM (a mixture of the sodium salt of a special alkylated naphthalene sulphonic acid with glue manufactured by I. G. Farbenindustrie A. G), and the Igepones (special fatty acid derivatives manufactured by the I. G. Farbenindustrie A. G.- Igepone is a registered trade-mark).
2 grams of Nekal AEM and 0.5 cc. of pyridine are dissolved in 5 cos. of water. To this solution there is added an aqueous solution of 0.3 gram of dinaphthole. After filtering off a small undissolved residue, a clear solution of the dye component is obtained. Thereupon 15 cos. of a 20% gelatin solution is thoroughly mixed with the solution of the dye component. The slightly alkaline solution is neutralized with acetic acid, and after solidifying, the gelatin ispreferably washed.
The gelatin containing the dye component is thereafter thoroughly mixed with an equal amount of silver halide gelatin emulsion to yield a light-sensitive emulsion suificient to cover 0.3 sq. metre,
The light-sensitive layer containing the dye component may then be used for the. production of a dye-image in a multi-layer material. The process employed for obtaining the dyeimage may be the known process of the local destrustion of the dye component depending on a silver image produced in the layer, and afterwards forming an azo dye from the dye component remaining in the layer; or converting the dye component to an azo dye uniformly throughout the layer and afterwards destroying the dye locally in dependence on the silver image. On coupling with diazotized sulphanilic acid, for instance, the dinaphthole yields an orange azo dye.
Similarly the layer maybe used in a material for the process of so-called color development in which case the dinaphthole serves as a coupling component for color development yielding a blue dye with the ordinary colo'r developers.
Silver halide emulsions prepared according to the process described above can be sensitized in the usual manner by adding sensitizers at any stage of their preparation.
A multi-layer material for color photographic purposes can be prepared by superimposing silver halide emulsions prepared in accordance with the invention.
I claim:
l. A process for producing layers for photographic purposes which comprises dissolving a dye-forming substance which is substantially insoluble in water in a solution comprising water and a quantity of a hydrotropic substance sufficient to form a true solution, incorporating a binding agent in said solution and then forming said solution into a layer.
2. A process for producing layers for photographic piu'poses which comprises dissolving a dye-forming substance which is substantially insoluble in water in a solution comprising water and a quantity of a hydrotropic substance sumcient to form a true solution, incorporating a colloid solution in said solution and then form-- ing said solution'into a layer.
3. A' process for producing layers for photographic purposes which comprises dissolving a dye-forming substance which is substantially insoluble in water in a solution comprising water and a quantity of a hydrotropic substance sufficient to form a true solution, adding a silver halide emulsion 'to said solution and then forming said solution into a layer.
4. A process for producing layers for photographic purposes which comprises dissolving a dye-forming substance which is substantially insoluble in water in a solution comprising water and a quantity of a hydrotropic substance sufiicient to form a true solution, incorporating a ,bindingagent and a light-sensitive silver halide insaid solution and then forming said solution into a layer.
5. A process for producing layers for photographic purposes which comprises dissolving a dye-forming substance which is substantially insoluble in water in a solution comprising water and a quantity of a hydrotropic substance sufiiv cient to form a true solution, adding a silver halide gelatin emulsion to said solution and then forming said emulsion containing the dye-forming substance into a layer.
6. A process for producing layers for photographic purposes which comprises dissolving a dye-forming substance which is substantially insoluble in water in a solution comprising water and a quantity of a hydrotropic substance sufflcient to form a true solution, incorporating a silver halide gelatin emulsion and a sensitizing dye in said solution and then forming said solution into a color sensitized light-sensitive layer.
BELA GAsPAR.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2310226X | 1939-07-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2310226A true US2310226A (en) | 1943-02-09 |
Family
ID=10903570
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US346435A Expired - Lifetime US2310226A (en) | 1939-07-19 | 1940-07-19 | Process for the manufacture of photographic materials |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2310226A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3335011A (en) * | 1962-03-23 | 1967-08-08 | Pavelle Corp | Production of stabilized dispersions of color couplers for photographic materials |
| US3372030A (en) * | 1962-12-14 | 1968-03-05 | Pavelle Corp | Method of shortening the processing time of color photography |
| US5298389A (en) * | 1992-09-29 | 1994-03-29 | Eastman Kodak Company | Dry gelatin addition to an emulsion/dispersion mixture |
-
1940
- 1940-07-19 US US346435A patent/US2310226A/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3335011A (en) * | 1962-03-23 | 1967-08-08 | Pavelle Corp | Production of stabilized dispersions of color couplers for photographic materials |
| US3372030A (en) * | 1962-12-14 | 1968-03-05 | Pavelle Corp | Method of shortening the processing time of color photography |
| US5298389A (en) * | 1992-09-29 | 1994-03-29 | Eastman Kodak Company | Dry gelatin addition to an emulsion/dispersion mixture |
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