US2380809A - Color couplers for photographic color development - Google Patents
Color couplers for photographic color development Download PDFInfo
- Publication number
- US2380809A US2380809A US389222A US38922241A US2380809A US 2380809 A US2380809 A US 2380809A US 389222 A US389222 A US 389222A US 38922241 A US38922241 A US 38922241A US 2380809 A US2380809 A US 2380809A
- Authority
- US
- United States
- Prior art keywords
- color
- photographic
- development
- developing
- couplers
- 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000000034 method Methods 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 229910052709 silver Inorganic materials 0.000 description 7
- 239000004332 silver Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 6
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 6
- QNGVNLMMEQUVQK-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C=C1 QNGVNLMMEQUVQK-UHFFFAOYSA-N 0.000 description 5
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 229910000029 sodium carbonate Inorganic materials 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- -1 silver salts Chemical class 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 235000010265 sodium sulphite Nutrition 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- QPKNFEVLZVJGBM-UHFFFAOYSA-N 2-aminonaphthalen-1-ol Chemical class C1=CC=CC2=C(O)C(N)=CC=C21 QPKNFEVLZVJGBM-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- 101100373139 Caenorhabditis elegans mig-14 gene Proteins 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 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
- G03C7/32—Colour coupling substances
- G03C7/36—Couplers containing compounds with active methylene groups
Definitions
- This invention relates to photographic color development and to processes of color development for use in connection with color photography.
- Y-rCHri-B where Y is one of the electro-negative groups CR- or 2.00- (wherexis anelhior aryl group, substituted or unsubstitimd) while B is an arylor hctcrocyclo-substitutcd amino roup.
- the invention are compounds having the general formula: "Ii "if --on
- the invention comprises the process of poration, in the photographic emulsion, before or after coating, of a color coupler as above deiineii and, further. the process of developing a latent photographic image by means of a color developer comprising in addition to an aromatic amino developing agent a color. coupler as above defined.
- the invention includes the method of color development which comprises developing a latent photographic image by means 01' an aromatic amino developer in the presence of color couplers as above defined, and eliminating the silver image which is formed during development so that a clear and transparent color image remains.
- the invention also consists in new or improved color iorming developers comprising, in addition to an aromatic amino developing agent, color couplers as above, defined.
- the present invention includesphoto- 2 l s,sso,soc
- graphic elements having at least one layer con- B essentially of the product resulting from the taining maker and transparent image composed cm-C c-N coupling in situ during development of color couplers as above defined, with the oxidation 5 K Cnhco product of an aromatic amino developing agent.
- the aromatic amino compounds which may be uethmol' "com" 100 used as developing asents in the present inventlon include the mono-, diand tri-amino-aryl- For m B to compounds.
- the mono-amino developing Rosanna 4 agents may be mentioned amino-phenols and amlno-cresols and their halogen derivatives and 4 amino-naphthols.
- the developing agents preferably used and g pan phenylened e g 3 having hitherto given the best results in connecl5 s u tion with the present invention are the aromatic fi fi fi g zgfl'i "g" :3 orthoand para-diamines. such as para-phenyl- 7 sodium hydroxide 2 enedlamine and its substitution products.
- These water h" 1000 developing agents may be substituted in one aminogroup'orintheringorinbothJormingzo 3 compounds such as: NR diethyl-para-phenylenedlamine.
- the invention is in no way limited to the use oi the color couplers in the developing solution itself.
- the color coupler which during the development forms the dye, can also be added to the photographic emulsion (for instance by adsorption upon the silver salts) before or after coating.
- the other ingredients of the color forming baths containing chiefly the aromatic amino developer, may be applied later, during the developing process. as a bath.
- the present invention may be utilized in the formation of colored photographic images on plates or papers as well as on films, employing gelatine or some other carrier substance :lor the silver halide.
- the developing process may be used for developing photographic material, provided with one or more sensitive layers, which are, applied on one side or on both sides of the support.
- the silver formed during the developing process may be eliminated.
- a bath should be used, however, which does not destroy the dye.
- a bath consisting of a solution in water of potassium ferricyanide and sodium thiosulphateeasily eliminates the silver without destroying the dye, leaving a pure dye image.
- the process of developing a colored image in a. gelatin-silver halide photographic layer which comprises coupling the development product of a primary aromatic amino developing compound with the coupler compound, 3 benzyl-5 acetonyll,2,4-oxodiazole 2.
- the process of developing a colored image in a gelatin-silver halide photographic layer which comprises coupling the development productof a primary aromatic amino developing compound with the color coupler compound of the general formula wherein X is an electro-negative organic radicalselected from the class consisting of acyl and cyano, while Y is an organic radical of the class consisting of substituted alkyl.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB31978/39A GB540760A (en) | 1939-12-11 | 1939-12-11 | Improvements in and relating to colour couplers for photographic colour development |
| GB22002/48A GB645043A (en) | 1939-12-11 | 1948-08-20 | Improvements in or relating to the production of colour photographic images |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2380809A true US2380809A (en) | 1945-07-31 |
Family
ID=26255644
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US389222A Expired - Lifetime US2380809A (en) | 1939-12-11 | 1941-04-18 | Color couplers for photographic color development |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US2380809A (en)) |
| BE (2) | BE440012A (en)) |
| DE (1) | DE870947C (en)) |
| FR (2) | FR869169A (en)) |
| GB (2) | GB540760A (en)) |
| IT (1) | IT390064A (en)) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2441491A (en) * | 1944-05-12 | 1948-05-11 | Ilford Ltd | Cyanacetylamino phenol color formers for color photography |
| US2531004A (en) * | 1947-11-26 | 1950-11-21 | Gen Aniline & Film Corp | Acetonitriles as azo components in diazotypes |
| DE1045230B (de) * | 1956-03-23 | 1958-11-27 | Gevaert Photo Prod Nv | Verfahren zur Herstellung photographischer Farbbilder nach dem Farbentwicklungsverfahren |
| US3189452A (en) * | 1961-12-05 | 1965-06-15 | Eastman Kodak Co | Color-forming photographic process utilizing a bleach-fix followed by a bleach |
| US4871652A (en) * | 1988-09-07 | 1989-10-03 | Eastman Kodak Company | Photographic silver halide material and process |
| US5066576A (en) * | 1989-10-03 | 1991-11-19 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
| US5162196A (en) * | 1989-11-20 | 1992-11-10 | Fuji Photo Film Co., Ltd. | Color coupler for photography and silver halide photographic material comprising the same |
| WO2017062523A2 (en) | 2015-10-05 | 2017-04-13 | Dsm Ip Assets B.V. | Oil compositions and methods of making |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE619300A (en)) * | 1959-04-06 | |||
| CH627562A5 (de) | 1977-04-29 | 1982-01-15 | Ciba Geigy Ag | Farbphotographisches material. |
-
0
- BE BE490600D patent/BE490600A/xx unknown
- BE BE440012D patent/BE440012A/xx unknown
- IT IT390064D patent/IT390064A/it unknown
-
1939
- 1939-12-11 GB GB31978/39A patent/GB540760A/en not_active Expired
-
1940
- 1940-12-11 DE DEG1238D patent/DE870947C/de not_active Expired
-
1941
- 1941-01-11 FR FR869169D patent/FR869169A/fr not_active Expired
- 1941-04-18 US US389222A patent/US2380809A/en not_active Expired - Lifetime
-
1948
- 1948-08-20 GB GB22002/48A patent/GB645043A/en not_active Expired
-
1949
- 1949-08-18 FR FR59472D patent/FR59472E/fr not_active Expired
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2441491A (en) * | 1944-05-12 | 1948-05-11 | Ilford Ltd | Cyanacetylamino phenol color formers for color photography |
| US2531004A (en) * | 1947-11-26 | 1950-11-21 | Gen Aniline & Film Corp | Acetonitriles as azo components in diazotypes |
| DE1045230B (de) * | 1956-03-23 | 1958-11-27 | Gevaert Photo Prod Nv | Verfahren zur Herstellung photographischer Farbbilder nach dem Farbentwicklungsverfahren |
| US2897079A (en) * | 1956-03-23 | 1959-07-28 | Gevaert Photo Prod Nv | Production of colored photographic images with oxodiazole couplers |
| US3189452A (en) * | 1961-12-05 | 1965-06-15 | Eastman Kodak Co | Color-forming photographic process utilizing a bleach-fix followed by a bleach |
| US4871652A (en) * | 1988-09-07 | 1989-10-03 | Eastman Kodak Company | Photographic silver halide material and process |
| US5066576A (en) * | 1989-10-03 | 1991-11-19 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
| US5162196A (en) * | 1989-11-20 | 1992-11-10 | Fuji Photo Film Co., Ltd. | Color coupler for photography and silver halide photographic material comprising the same |
| WO2017062523A2 (en) | 2015-10-05 | 2017-04-13 | Dsm Ip Assets B.V. | Oil compositions and methods of making |
Also Published As
| Publication number | Publication date |
|---|---|
| IT390064A (en)) | |
| FR869169A (fr) | 1942-01-26 |
| GB645043A (en) | 1950-10-25 |
| BE440012A (en)) | |
| BE490600A (en)) | |
| GB540760A (en) | 1941-10-29 |
| DE870947C (de) | 1953-03-19 |
| FR59472E (fr) | 1954-05-25 |
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