US2154918A - Coupling compounds for color forming development - Google Patents
Coupling compounds for color forming development Download PDFInfo
- Publication number
- US2154918A US2154918A US216293A US21629338A US2154918A US 2154918 A US2154918 A US 2154918A US 216293 A US216293 A US 216293A US 21629338 A US21629338 A US 21629338A US 2154918 A US2154918 A US 2154918A
- Authority
- US
- United States
- Prior art keywords
- color
- color forming
- development
- coupling compounds
- forming development
- 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
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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
- G03C7/32—Colour coupling substances
- G03C7/36—Couplers containing compounds with active methylene groups
Definitions
- the present invention relates to coupling compounds for color forming development.
- Color photographic pictures have been produced with the aid of color developing dyestufl. components having active methylene groups which in the development of a latent silver image by me'ans of a developer containing a free amino-group.
- Such dyestuii components are, for example, derivatives of aceto-acetic acid esters,
- a further object of the invention resides in the provision of a new and improved class of dyestufi components, color formers or coupling compounds.
- Still another object of the invention is the proa the new class of color formers.
- a further object is to provide a photographic emulsion for color forming development having incorporated compounds from the new class of color formers being fast to diffusion with respect to the silver halide emulsions.
- R stands for alkyl, aryl and aralkyl
- X is a suitable inorganic acid radical, for example Cl
- ketones there may be used, for example, chloroacetophenone, bromacetophenone, monochloracetone,symmetrical dichloracetone, bromacetonaphthone, para-phenylbromacetophenone, para-phenylc fi p 5 none and diphenylene:para-para'-dichloromethyl ketone.
- the reaction of the methyl ketones and pyridine derivatives is exothermic.
- the opera tion of forming the compound may proceed in the presence or absence of a solvent.
- Suitable so1- m vents are, for example, benzene or ether.
- the new dyestufi components may be added to 15 the developer or to the emulsion.
- yellow dyestuff pictures are produced.
- groups are, for instance, substantive groups as described in U. S. patent application Ser. No. 72,718 filed April 4, 1936, radicals of highly polymeric carboxylic acids as describedinU. S. patent application Ser. No. 90,726 filed July 15, 1936, 30 aliphatic radicals consisting of an extended saturated or unsaturated carbon chain as described in U. S. patent application Ser.No.
- radicals of carbohydrates U. S. patent application Ser. No. 159,518 filed August 17, 1937
- radicalsof natural resins U. S. patent application Ser. No. 164,499 filed September 18, 1937
- sterol radicals U. S. patent application Ser. No. 166,832 filed Octoberl, 1937
- radical ofithe dyestuff component itself recurs periodically (U. S. 5 3 patent application Ser. No. 171,701 filed October 29, 1937).
- radicals may be introduced into the molecule of the dyestufl com-' ponents which make the latter fast to diflusion, which radicals consist of hydroaromatic and Such ' chloride of the formula hydro-heterocyclic residues, then further menthane radicals (U; S. patent application Ser. No. 176,058 filed November 23, 1937).
- These groups may be introduced either directly into the ketone, as for example into the diphenylacetyl chloride, into the pyridine nucleus or at any other position in the molecule, for example into the benzene nucleus of the bromacetophenone and indeed either directly or by means of an amino-, hydroxyl-, or carboxyl group in the form of an acid amide or an ester.
- the dyestuif components may be used in the production of both single layer materials and multi-layer materials, and in the latter case the layers may be arranged on one or both sides of a support. Alternatively a mixture of emulsion particles containing different dyestufl components may be applied to the support.
- ture may be produced by simple color forming development or by reversal development as described in U. S. patent applications Ser. No.
- the above described coupling compounds have an improved reactivity and form the desired dyestufls more easily than the hitherto known. color formers, since the reactive methylene group appears to be activated by the vicinal pyridine nucleus.
- Example 1 An exposed silver halide emulsion layer is developed with a developer of the following composition:
- Example 2 An exposed silver halide emulsion layer is developed with a developer of the .following composition:
- Ayellow dyestufl picture is obtained;
- Example 3.--3 grams of diphenylacylpyridinlum I 000g Ol are dissolved in 25 cc. of methanol end cc. of water, and the solution is added to 400 cc. of a gelatine emulsion of 5 percent strength, and the latter iscast to form a layer.
- dimethyl-aminoaniline there is obtained a yellow picture.
- a color forming developer capable of forming a dyestuff with the oxidation product of an aro-' matic amino developer, a pyridine derivative of the following general formula improvement which comprises employing as "a color forming developer a composition of matter comprising an aqueous solution of an alkali, an
- Silver halide emulsion for color photography capable of beingdeveloped in color by means of an aromatic amino develop'r, said silver halii'le emulsion containing a pyridine derivative of the following general formula inwhichRisamembei-ofthegroupconsisting of alkyL-aryl, and aralkyl, and x is an anion;
- a color-forming developer comprising an aqueoussolution of an alhli. an aromatic amino developlng agent, and a pyridine derivative of in which R is a. member of the group eonsisfln:
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEI0058706 | 1937-07-30 |
Publications (1)
Publication Number | Publication Date |
---|---|
US2154918A true US2154918A (en) | 1939-04-18 |
Family
ID=7194843
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US216293A Expired - Lifetime US2154918A (en) | 1937-07-30 | 1938-06-28 | Coupling compounds for color forming development |
Country Status (4)
Country | Link |
---|---|
US (1) | US2154918A (de) |
BE (1) | BE429448A (de) |
FR (1) | FR841425A (de) |
GB (1) | GB504376A (de) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2421693A (en) * | 1944-09-16 | 1947-06-03 | Gen Aniline & Film Corp | Imidazolone color formers |
US2433632A (en) * | 1942-12-23 | 1947-12-30 | Rca Corp | Fibrous sheet material for the electrolytic formation of azo dye image records thereon |
US2440526A (en) * | 1942-12-23 | 1948-04-27 | Nellie W Solomon | Fibrous sheet material for the electrolytic formation of an azo dyestuff thereon |
US2440954A (en) * | 1945-08-23 | 1948-05-04 | Du Pont | Process for eliminating stain from color-yielding elements by treatment with aromatic aldehydes containing an acyl group |
US2531091A (en) * | 1945-08-03 | 1950-11-21 | Gevaert Photo Prod Nv | N-acetonyl-pyridinium chloride as an azo coupling component in diazotypes |
US2776116A (en) * | 1953-10-29 | 1957-01-01 | Acme Highway Prod | Beam guard for highways and the like |
US5035987A (en) * | 1989-10-05 | 1991-07-30 | Agfa Gevaert Aktiengesellschaft | Color photographic recording material containing a DIR coupler |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2418748A (en) * | 1944-06-07 | 1947-04-08 | Gen Aniline & Film Corp | Heterocyclic color couplers |
-
0
- BE BE429448D patent/BE429448A/xx unknown
-
1937
- 1937-08-24 GB GB23190/37A patent/GB504376A/en not_active Expired
-
1938
- 1938-06-28 US US216293A patent/US2154918A/en not_active Expired - Lifetime
- 1938-07-29 FR FR841425D patent/FR841425A/fr not_active Expired
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2433632A (en) * | 1942-12-23 | 1947-12-30 | Rca Corp | Fibrous sheet material for the electrolytic formation of azo dye image records thereon |
US2440526A (en) * | 1942-12-23 | 1948-04-27 | Nellie W Solomon | Fibrous sheet material for the electrolytic formation of an azo dyestuff thereon |
US2421693A (en) * | 1944-09-16 | 1947-06-03 | Gen Aniline & Film Corp | Imidazolone color formers |
US2531091A (en) * | 1945-08-03 | 1950-11-21 | Gevaert Photo Prod Nv | N-acetonyl-pyridinium chloride as an azo coupling component in diazotypes |
US2440954A (en) * | 1945-08-23 | 1948-05-04 | Du Pont | Process for eliminating stain from color-yielding elements by treatment with aromatic aldehydes containing an acyl group |
US2776116A (en) * | 1953-10-29 | 1957-01-01 | Acme Highway Prod | Beam guard for highways and the like |
US5035987A (en) * | 1989-10-05 | 1991-07-30 | Agfa Gevaert Aktiengesellschaft | Color photographic recording material containing a DIR coupler |
Also Published As
Publication number | Publication date |
---|---|
FR841425A (fr) | 1939-05-19 |
BE429448A (de) | |
GB504376A (en) | 1939-04-24 |
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