US2375344A - Color couplers for color development - Google Patents
Color couplers for color development Download PDFInfo
- Publication number
- US2375344A US2375344A US394290A US39429041A US2375344A US 2375344 A US2375344 A US 2375344A US 394290 A US394290 A US 394290A US 39429041 A US39429041 A US 39429041A US 2375344 A US2375344 A US 2375344A
- Authority
- US
- United States
- Prior art keywords
- color
- couplers
- developing
- photographic
- 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
Links
- 238000000034 method Methods 0.000 description 11
- 230000008569 process Effects 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
- 229910052709 silver Inorganic materials 0.000 description 5
- 239000004332 silver Substances 0.000 description 5
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 4
- -1 acyl acetic acid ester Chemical class 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 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 3
- 230000008901 benefit Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 3
- 150000007857 hydrazones Chemical class 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000001828 Gelatine Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 238000009792 diffusion process Methods 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JHGFAGAHQPLGOQ-UHFFFAOYSA-N 1-n,1-n,2-trimethylbenzene-1,4-diamine Chemical compound CN(C)C1=CC=C(N)C=C1C JHGFAGAHQPLGOQ-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
- FLROJJGKUKLCAE-UHFFFAOYSA-N 3-amino-2-methylphenol Chemical class CC1=C(N)C=CC=C1O FLROJJGKUKLCAE-UHFFFAOYSA-N 0.000 description 1
- SKIBELYSXFYZPS-UHFFFAOYSA-N 4-n-ethylbenzene-1,4-diamine Chemical compound CCNC1=CC=C(N)C=C1 SKIBELYSXFYZPS-UHFFFAOYSA-N 0.000 description 1
- 241000285023 Formosa Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 229930194542 Keto Natural products 0.000 description 1
- BZORFPDSXLZWJF-UHFFFAOYSA-N N,N-dimethyl-1,4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000003869 acetamides Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229940083761 high-ceiling diuretics pyrazolone derivative Drugs 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 150000003378 silver Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001228 spectrum Methods 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
- Our invention relates to color photographic images and to means for producing same. More I particularly our invention relates to a process and material for color development in connection with v also the images obtained therewith. 1
- color couplers as well as photographic emulsions or sensitive layers, in which such color couplers are incorporated, and photographic materials comprising a sensitive layer with a content of such a-color coupler.
- colorphotographic image can be obtained by the use of such developers that form colored and-insoluble oxidation products during development, the product thus formed 001-. oring the gelatine adjacent to the developed silver. It is also known that colored images can be formed by the addition to the developing agents of certain products, called color couplers,
- color couplers that can be used.
- This new class of color couplers includes the monoand poly-hydrazones being the products of condensation ofone or more hydrazides, which contain at least one reactive methylene group, with tive methylene groups.
- Example 7 a magenta color.
- Example 3 Example 4: Example 5: Example 6;
- Our color couplers may be added to a developing bath containing a fair amount of a sulflte.
- Another advantage of this invention is that the newcolor couplers are generally soluble in weak bases, such as carbonates, so that they can be added to the developing baths without the Usually the developing baths are only slightly coloredf
- a great advantage offered by the new class I of color 'couplers is that owingto their wide diversity. the most varying tones can be obtained, which is of utmost importance for the mutual adaptation of the different dyes formed-by color development in a material with two or more layers. 1
- Still another advantage of the new color cou plers is that they can quite easily be rendered free from diffusion from one layer into another, which is very important when they are to be incorporated in the emulsion directly.
- condensation with hydrazides contain-. ing a sumcient amount of carbon atoms sufllces.
- the invention comprises the color couplers defined above as well as the improved process oi producing color photographic images by means or these color couplers. Furthermore the invention comprises the improved processfof i'orming color. photographic images by the'incorporation inthe photographic emulsion, before or after coating, of a color coupler as defined above and development of such an emulsion after, exposure.
- the invention also comprises a pho-z 75 Water v tographic emulsion, which contains a color coupier-as defined above and preferably such a color coupler which is-derived from a hydrazide containing' a sufllcient number of carbon atoms to substantially prevent diffusion, as well as a photographic material comprising one or seyeral layers formed of such an emulsion.
- the invention further includes 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, and it includes also a color developer containing these substances.
- the invention also includes a process or method of .color developlment which comprises developing a latent photographic image by means of 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 pounds.
- Our invention further includes photographic elements having at least one layer containing a clear and transparent image composed essentially of the product resulting from the coupling "in situ during development of color couplers as above defined, with the oxidation product 0 an aromatic amino developing agent.
- aromatic compounds which may be as developing agents in the present invention-M include the mono-, diand tri-amino-aryl comagents may be mentioned amino-phenols and amino-cresols and their halogen derivatives and amino-naphthols.
- the developing agents preferably used and Eiv-v ing the best results in connection with the present invention are the aromatic orthoand'paradiamines, such as orthoand para-phenylenediaminesl These developing agents may be substituted in oneamino group or in the ring or- I in one amino group and in the ring, forming different compounds such as:
- color development we not only mean the formation of a colored image by the interaction, during the photographic developing process, of a developer and a color coupler but also the formation of a colored image by the action of an insoluble oxidising agent, such as for instance silverferri-cy'anide, present in a photographic layer, or a developing bath which contains.
- color coupler as' descrlbed above.
- This color coupler according to our invention may also be present in the emulsion.
- Organic solvents for instance acetone, alcohols or the like, may be used-to dissolve the color can be added to the developing bath without the intervention of organic solvents.
- the invention is in no way limited to the use of the color couplers in the developing solution itself.
- one of the essential products viz. the color coupler, which during the development form the dye, can also be added to the photographic emulsion, before or after coating, for instance by adsorption upon the silver salts.
- the other ingredients of the color forming baths containing chiefly the aromatic ammodeveloper, may be applied later, during the developing process, as a bath.
- the present invention maybe utilized in the formation of colored photographic images on plates or papers as well as on film, employing gelatine or other carriers for the silver halide.
- the developing process may be used for the developing of photographic material provided with one or several sensitive layers, which are applied on one side or onboth sides of the support.
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 |
|---|---|---|---|
| GB471840A GB590637A (en) | 1940-03-13 | Improvements in and relating to photographic colour development |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2375344A true US2375344A (en) | 1945-05-08 |
Family
ID=9782481
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US394290A Expired - Lifetime US2375344A (en) | 1940-03-13 | 1941-05-20 | Color couplers for color development |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US2375344A (en)) |
| BE (1) | BE440740A (en)) |
| FR (1) | FR870771A (en)) |
| NL (1) | NL58022C (en)) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2495000A (en) * | 1945-02-24 | 1950-01-17 | Gen Aniline & Film Corp | Production of azo dyestuff images from n-acyl-n-aryl hydrazine developers |
| US2527476A (en) * | 1941-03-17 | 1950-10-24 | Gevaert Photo Prod Nv | Cyanoacetylhydrazones as photographic color couplers |
| US3186840A (en) * | 1958-12-11 | 1965-06-01 | Agfa Ag | Direct positive colored photographic elements containing dihydrazones and process for forming colored masks therefrom |
| US3485627A (en) * | 1964-02-22 | 1969-12-23 | Agfa Ag | Process and material for the preparation of masks for the reproduction of color images |
| US3619196A (en) * | 1968-10-24 | 1971-11-09 | Konishiroku Photo Ind | Light-sensitive color-photographic emulsions |
-
0
- BE BE440740D patent/BE440740A/xx unknown
- NL NL58022D patent/NL58022C/xx active
-
1941
- 1941-03-12 FR FR870771D patent/FR870771A/fr not_active Expired
- 1941-05-20 US US394290A patent/US2375344A/en not_active Expired - Lifetime
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2527476A (en) * | 1941-03-17 | 1950-10-24 | Gevaert Photo Prod Nv | Cyanoacetylhydrazones as photographic color couplers |
| US2495000A (en) * | 1945-02-24 | 1950-01-17 | Gen Aniline & Film Corp | Production of azo dyestuff images from n-acyl-n-aryl hydrazine developers |
| US3186840A (en) * | 1958-12-11 | 1965-06-01 | Agfa Ag | Direct positive colored photographic elements containing dihydrazones and process for forming colored masks therefrom |
| US3485627A (en) * | 1964-02-22 | 1969-12-23 | Agfa Ag | Process and material for the preparation of masks for the reproduction of color images |
| US3619196A (en) * | 1968-10-24 | 1971-11-09 | Konishiroku Photo Ind | Light-sensitive color-photographic emulsions |
Also Published As
| Publication number | Publication date |
|---|---|
| BE440740A (en)) | |
| NL58022C (en)) | |
| FR870771A (fr) | 1942-03-24 |
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