US3510306A - Developing process for color photography - Google Patents
Developing process for color photography Download PDFInfo
- Publication number
- US3510306A US3510306A US556238A US3510306DA US3510306A US 3510306 A US3510306 A US 3510306A US 556238 A US556238 A US 556238A US 3510306D A US3510306D A US 3510306DA US 3510306 A US3510306 A US 3510306A
- Authority
- US
- United States
- Prior art keywords
- coupler
- group
- color
- yellow
- anilide
- 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 21
- 239000000975 dye Substances 0.000 description 17
- 238000010521 absorption reaction Methods 0.000 description 16
- 150000003931 anilides Chemical class 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- -1 aromatic primary amine Chemical class 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 11
- 229910052709 silver Inorganic materials 0.000 description 10
- 239000004332 silver Substances 0.000 description 10
- 230000003595 spectral effect Effects 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000001043 yellow dye Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 125000004442 acylamino group Chemical group 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 125000004104 aryloxy group Chemical group 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- 230000018109 developmental process Effects 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ULHFFAFDSSHFDA-UHFFFAOYSA-N 1-amino-2-ethoxybenzene Chemical compound CCOC1=CC=CC=C1N ULHFFAFDSSHFDA-UHFFFAOYSA-N 0.000 description 1
- FTZQXOJYPFINKJ-UHFFFAOYSA-N 2-fluoroaniline Chemical compound NC1=CC=CC=C1F FTZQXOJYPFINKJ-UHFFFAOYSA-N 0.000 description 1
- QNDKYJBGVDTFJQ-UHFFFAOYSA-N 3-(2-methylphenyl)-3-oxo-N-phenylpropanamide Chemical compound CC1=C(C(=O)CC(=O)NC2=CC=CC=C2)C=CC=C1 QNDKYJBGVDTFJQ-UHFFFAOYSA-N 0.000 description 1
- XRZDIHADHZSFBB-UHFFFAOYSA-N 3-oxo-n,3-diphenylpropanamide Chemical compound C=1C=CC=CC=1NC(=O)CC(=O)C1=CC=CC=C1 XRZDIHADHZSFBB-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- UNULPFKXRJPSCO-UHFFFAOYSA-N ethyl 3-(2-methylphenyl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1C UNULPFKXRJPSCO-UHFFFAOYSA-N 0.000 description 1
- LLFKVNDSLHMEQC-UHFFFAOYSA-N ethyl 3-(3-methylphenyl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC(C)=C1 LLFKVNDSLHMEQC-UHFFFAOYSA-N 0.000 description 1
- GEQMJBPKCOZHMV-UHFFFAOYSA-N ethyl 3-(4-methylphenyl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=C(C)C=C1 GEQMJBPKCOZHMV-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- KYPIASPTMDEDQB-UHFFFAOYSA-N n,2-diphenylacetamide Chemical compound C=1C=CC=CC=1NC(=O)CC1=CC=CC=C1 KYPIASPTMDEDQB-UHFFFAOYSA-N 0.000 description 1
- ZNQPYZLDPAAVHH-UHFFFAOYSA-N n-(4-aminophenyl)-1-phenylmethanesulfonamide Chemical compound C1=CC(N)=CC=C1NS(=O)(=O)CC1=CC=CC=C1 ZNQPYZLDPAAVHH-UHFFFAOYSA-N 0.000 description 1
- VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Images
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
- G03C7/362—Benzoyl-acetanilide couplers
Definitions
- the invention is directed to an improved color photographic developing process in which a coupler of the formula Y Q-oo omo 0 NH is reacted with the oxidation product of an aromatic primary developer.
- the couplers of this invention are yellow couplers capable of forming yellow dyes, having excellent spectral absorption characteristics for providing ideal yellow images and have good silver removing properties.
- the present invention relates to color photography and more particularly to a color photographic developing process using a color developing solution containing an improved coupler.
- Such a coupler as forms dye images by the reaction thereof with the oxidation product of an aromatic primary amine developer in a color photographic development is known and there are many patents concerned with such couplers.
- Such a coupler will be coupled with the oxidation product of an aromatic primary amine to form a dye which is insoluble in water or a usual developing solution, whereby dye images can be left in the photographic emulsion layer.
- Such a coupler may be added in a developing solution or may be incorporated in a photographic emulsion layer before exposure.
- the coupler in this invention is of the type which is added to a developing solution.
- This type of coupling process is usually a subtractive color process, wherein the couplers capable of forming cyan, magenta and yellow dyes are used.
- Couplers for color photography are required to form, by color development, dyes having desired spectral absorption characteristics.
- a yellow coupler must absorb completely blue lights and transmit completely green and red lights.
- many of the conventionally used couplers are deficient in such characteristics.
- it is, after a first develop ment, exposed in blue light, subjected to a yellow color development, and then bleached and fixed to provide yellow images. But in this case it frequently happens that the reduced silver remains in the bleaching step caused by the slow oxidation of the reduced silver and the silver remains in the yellow image without being removed completely in the fixing step.
- the phenomenon is called insufficient silver removal. This reduces extremely the transparency of the yellow image.
- An object of this invention is to provide a color photographic developing process using an improved yellow coupler capable of forming a yellow dye having the ex- 3,510,306 Patented May 5, 1970 cellent spectral absorption characteristics for providing ideal yellow images and having good silver-removing @woomooun
- X represents a halogen atom, an alkyl group, a trifluoromethyl group, an alkoxy group, an acylamino group or an aryloxy group
- Y represents a hydrogen atom or above-mentioned group X
- Z represents a hydrogen atom or a halogen atom.
- the above alkyl group may be, for example, methyl, ethyl, and propyl groups.
- the above-mentioned alkoxy group may be, for example, methoxy, ethoxy and propoxy groups.
- the acylamino group may be, for example, acetamino, propionamino, benzoylamino, toluenecarboamino, methanesulfoamino, benzenesulfonamino, and toluenesulfonamino groups.
- the aryloxy group may be, for example, phenoxy and tolyloxy groups.
- benzoylacetanilide is useful as a yellow coupler but the dye image obtained by using the yellow coupler has a bad silver-removing property and reduced spectral absorption characteristics.
- the accompanying drawing contains a single figure which is a graphical plot of the absorption curves of a material of this invention and other materials.
- the spectral absorption curve A of a dye image formed by the oxidizing coupling of Z-methylbenzoylaceto-(Z-chloro) anilide ' which is a typical coupler used in this invention and a color developer, 4-N,N-diethylaminoaniline
- the spectral absorption curve C of the dye image obtained from another control coupler, Z-methylbenzoylacetanilide and the above-mentioned color developer In the graph, the vertical axis is graduated for Optical Densityand the horizontal for wavelength of light.
- the dye image obtained from the coupler of this invention has less undesirable components which absorb in the green range and has very excellent absorption characteristics.
- the coupler of this invention has very preferable property in silver removal as shown below.
- the dye image (E) obtained from 2 methylbenzoylaceto-(4-(4- toluenesulfonamido)
- the results are as [fOllOWSZ 5 be considered to be based on the chemical structure thereof in that the benzoyl nucleus has a methyl group and the anilide nucleus has as substituents at least one of the DB group consisting of halogen atoms, alkyl groups, trifluoro- Dye image 1 0 L 5 2 0 methyl groups, alkoxy groups, acylamino groups or aryloxy groups. 8: 2; 8: H2 81%; In particular, as is clear from the examples below, the 0.36 0. 0.28 0.
- the use of the couplers shall not be limited to natural color photography but they may be used for obtaining From the results it will be clear that the couplers used mono-color images or two-color images. in this invention give very good silver removing property. Examples of the yellow couplers useful in this invention The good silver-removing property shows up in the exare as follows:
- PREPARATION 3 4-methylbenzoylaceto- (2-fluoro) anilide-- (Formula 12)
- the procedure as in Preparation 1 was repeated using 1 mole of ethyl-4-methylbenzoylacetate, 1 mole of ofluoroaniline, and 300 ml. of xylene to provide'a white" crystalline product which was recrystallized by using methanol.
- the yield was 49% and the melting'point of the crystal was 109 C.
- Example 2 The same test sample as in Example 1 was subjected to the same diflferential exposure as in the example and then color developed as in the example using Z-methylbenzoylaceto-(Z-ethoxy)anilide (Formula 16) instead of wherein X represents a member selected from the group.
- EXAMPE 3 The same test sample as in Example 1 was subjected to ,diflferential exposure and, using a yellow color developing solution having the following composition, was color developed as in Example 1:
- EXAMPLE 4 The same procedure as'in Example 1 was repeated using as the coupler 4 methylbenzoylaceto-(2-fluoro) anilide (Formula 12) instead of Z-methylbenzoylaceto- (2-ch1oro)anilide to give a positive image of yellow dye having an absorption maximum of 448 nm. and very good transparency.
- EXAMPLE 5 The same procedure as in Example 1 was repeated using as the coupler 2-methylbenzoylaceto(4-(4-toluenesulfonamido)anilide (Formula 17) instead of 2-methylbenzoylaceto-(2-chloro) anilide to provide a positive image of yellow dye having an absorption maximum of 442 nm.
- Y represents a member selected from the group consisting of a hydrogen atom, a halogen atom, an alkyl group, a trifluoromethyl group, an alkoxyl group, an acylamino group and an aryloxy group
- Z represents a member selected from the group consisting of a hydrogen atom and a halogen atom.
- alkyl group is selected from the group consisting of methyl, ethyl and propyl.
- alkoxyl group is selected from the group consisting of methoxy, ethoxy and propoxy.
- acylamino group is selected from the group consisting of acetamino, propionamino, benzoylamino, toluenecarboamino, methane-sulfoneamino, 'benzenesulfoneamino and toluenesulfonamino.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3377565 | 1965-06-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3510306A true US3510306A (en) | 1970-05-05 |
Family
ID=12395809
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US556238A Expired - Lifetime US3510306A (en) | 1965-06-09 | 1966-06-08 | Developing process for color photography |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3510306A (forum.php) |
| BE (1) | BE682258A (forum.php) |
| CH (1) | CH470006A (forum.php) |
| DE (1) | DE1547842C3 (forum.php) |
| GB (1) | GB1122905A (forum.php) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4201584A (en) * | 1977-10-07 | 1980-05-06 | Agfa-Gevaert N.V. | Silver halide elements containing yellow forming color couplers for silver halide photography |
| US4842979A (en) * | 1984-12-27 | 1989-06-27 | Fuji Photo Film Co., Ltd. | Black color heat-sensitive diazo microcapsule recording material with benzoylacetic amide coupler |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB595314A (en) * | 1944-11-02 | 1947-12-02 | Kodak Ltd | Improvements in photographic colour forming developers and process of colour development |
| US2513190A (en) * | 1948-02-18 | 1950-06-27 | Du Pont | Polymeric color formers |
-
1966
- 1966-06-03 GB GB24893/66A patent/GB1122905A/en not_active Expired
- 1966-06-08 BE BE682258D patent/BE682258A/xx unknown
- 1966-06-08 DE DE1547842A patent/DE1547842C3/de not_active Expired
- 1966-06-08 US US556238A patent/US3510306A/en not_active Expired - Lifetime
- 1966-06-09 CH CH832566A patent/CH470006A/de unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB595314A (en) * | 1944-11-02 | 1947-12-02 | Kodak Ltd | Improvements in photographic colour forming developers and process of colour development |
| US2513190A (en) * | 1948-02-18 | 1950-06-27 | Du Pont | Polymeric color formers |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4201584A (en) * | 1977-10-07 | 1980-05-06 | Agfa-Gevaert N.V. | Silver halide elements containing yellow forming color couplers for silver halide photography |
| US4842979A (en) * | 1984-12-27 | 1989-06-27 | Fuji Photo Film Co., Ltd. | Black color heat-sensitive diazo microcapsule recording material with benzoylacetic amide coupler |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1547842A1 (de) | 1970-01-08 |
| DE1547842B2 (de) | 1975-01-09 |
| BE682258A (forum.php) | 1966-11-14 |
| DE1547842C3 (de) | 1975-08-14 |
| GB1122905A (en) | 1968-08-07 |
| CH470006A (de) | 1969-03-15 |
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