US2673801A - Production of color photographic images - Google Patents
Production of color photographic images Download PDFInfo
- Publication number
- US2673801A US2673801A US128913A US12891349A US2673801A US 2673801 A US2673801 A US 2673801A US 128913 A US128913 A US 128913A US 12891349 A US12891349 A US 12891349A US 2673801 A US2673801 A US 2673801A
- Authority
- US
- United States
- Prior art keywords
- water
- indazolone
- formula
- solution
- added
- 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
- 238000004519 manufacturing process Methods 0.000 title description 5
- 239000000839 emulsion Substances 0.000 claims description 18
- -1 SILVER HALIDE Chemical class 0.000 claims description 9
- 229910052709 silver Inorganic materials 0.000 claims description 9
- 239000004332 silver Substances 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 5
- 239000000084 colloidal system Substances 0.000 claims description 4
- 239000000243 solution Substances 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 24
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 23
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 239000007864 aqueous solution Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 239000000203 mixture Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 12
- 238000010521 absorption reaction Methods 0.000 description 11
- 229910000027 potassium carbonate Inorganic materials 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- LOCAIGRSOJUCTB-UHFFFAOYSA-N indazol-3-one Chemical compound C1=CC=C2C(=O)N=NC2=C1 LOCAIGRSOJUCTB-UHFFFAOYSA-N 0.000 description 7
- 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 6
- 238000009835 boiling Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 229910021653 sulphate ion Inorganic materials 0.000 description 6
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 229940001482 sodium sulfite Drugs 0.000 description 5
- 235000010265 sodium sulphite Nutrition 0.000 description 5
- AYLDJQABCMPYEN-UHFFFAOYSA-N (4-azaniumylphenyl)-diethylazanium;sulfate Chemical compound OS(O)(=O)=O.CCN(CC)C1=CC=C(N)C=C1 AYLDJQABCMPYEN-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 3
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 3
- XTBFKMDOQMQYPP-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine;hydron;chloride Chemical compound Cl.CCN(CC)C1=CC=C(N)C=C1 XTBFKMDOQMQYPP-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 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
- 239000000706 filtrate Substances 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- QYZZJSKJOTULFS-UHFFFAOYSA-N 2-(2,3-diaminophenyl)-2-phenylpropanedioic acid Chemical compound NC1=CC=CC(C(C(O)=O)(C(O)=O)C=2C=CC=CC=2)=C1N QYZZJSKJOTULFS-UHFFFAOYSA-N 0.000 description 1
- MJNYPLCGWXFYPD-UHFFFAOYSA-N 2-amino-5-sulfobenzoic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1C(O)=O MJNYPLCGWXFYPD-UHFFFAOYSA-N 0.000 description 1
- BSQLQMLFTHJVKS-UHFFFAOYSA-N 2-chloro-1,3-benzothiazole Chemical compound C1=CC=C2SC(Cl)=NC2=C1 BSQLQMLFTHJVKS-UHFFFAOYSA-N 0.000 description 1
- INEJTLPKMPELDM-UHFFFAOYSA-N 4-aminoindazol-3-one Chemical compound NC1=CC=CC2=C1C(=O)N=N2 INEJTLPKMPELDM-UHFFFAOYSA-N 0.000 description 1
- AASCIDHHJKKVMV-UHFFFAOYSA-N 4-chloroindazol-3-one Chemical compound ClC1=CC=CC2=C1C(=O)N=N2 AASCIDHHJKKVMV-UHFFFAOYSA-N 0.000 description 1
- JIKKQMRKAKZLJS-UHFFFAOYSA-N 4-nitroindazol-3-one Chemical compound [O-][N+](=O)C1=CC=CC2=C1C(=O)N=N2 JIKKQMRKAKZLJS-UHFFFAOYSA-N 0.000 description 1
- LGBOAAYNWOZWFE-UHFFFAOYSA-N 6-aminoindazol-3-one hydrochloride Chemical compound Cl.NC1=CC=C2C(N=NC2=C1)=O LGBOAAYNWOZWFE-UHFFFAOYSA-N 0.000 description 1
- 101710134784 Agnoprotein Proteins 0.000 description 1
- PKNSESCSLJMFDK-UHFFFAOYSA-N S(=O)(=O)(OC)OC.CC=1SC2=C(N1)C(=CC=C2)S Chemical compound S(=O)(=O)(OC)OC.CC=1SC2=C(N1)C(=CC=C2)S PKNSESCSLJMFDK-UHFFFAOYSA-N 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical class OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 1
- 125000005064 octadecenyl group Chemical group C(=CCCCCCCCCCCCCCCCC)* 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical compound C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 235000010269 sulphur dioxide Nutrition 0.000 description 1
- 239000000725 suspension 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
- G03C7/32—Colour coupling substances
- G03C7/3231—Couplers containing an indazolone ring
Definitions
- This invention relates to a. process for the production of color photographic images by color development in the presence of a color coupler, to photographic developers, photographic material containing such couplers, and photographic images obtained by such a process.
- a colored image may be formedv by developing a reducible silver salt image in the presence of a compound which during the development couples with the oxidation product of the developing agent and forms a dyestufi which is deposited on the developed silver grains.
- magenta image may also be obtained when a compound is used as a color coupler which does not contain such. an active methylene group.
- a further object of this invention is to provide new photographic developers containing a color coupler.
- Another object of the invention is to provide new photographic material containing a color coupler.
- a reducible silver salt image is developed with a primary aromatic amino developing agent in the presence of a compound corresponding to the following Formula I:
- aromatic nucleus may be isocyclic, heterocyclic
- the polycyclic nucleus completed by Z may contain at least one further -NH-NH-CO- group so as to have a double indazolone compound.
- the compound, as completed by Z may-- also contain two or more nuclei linked by a chemical bound or by a bior poly-valent atom or group, such as Bearing in mind that the new color coupler may be represented by Formula II, it is believed that coupling with the oxidation products of the developing agent occurs at the N-atom in ortho-- position to the OH group. This assumption is These formulae are analogous to the formula LV of Baker for 2-substituted indazolone (J.
- Color couplers according to Formula I may be obtained by causing a molecule of water to split off from aromatic, dihydro-aromatic or heterocyclic monoor poly-(orthohydrazino carboxylic acids) according to the method described by I K. Pfannsteil and J. Janecke in Berichte 751 Sometimes, the preparation of one of said hydrazino acids yields directly the corresponding indazolone because the hydrazino acid although occurring at an intermediate stage cannot be isolated.
- the color coupler according. to my present invention may also be obtained in a manner anal be written in many tautomeric forms, one of which is represented by the following Formula Most of these color coupler are converted into a yellow product when in an oxidizing medium such as a bath for removal of the silver so that a yellow reversal image, which results from the oxidation of th residual color coupler in the bath for removing the silver, is added to the dyestuff image formed on color development. If this is undesirable, the formation of the yellow product may be avoided by treating the color developed emulsion layer, before removing the silver, with a bath containing formaldehyde, a formaldehyde-yielding compound, or another aldehyde. Such an aldehyde is supposed to react with the --NHNHCO group of the coupler, avoiding in this way any subsequent coupling or formation of yellow oxidation products.
- the dyestufis obtained on color development with the color couplers according to the present invention are more stable to acid than those obtained with the known pyrazolones, and those which contain a substituent rendering them fast to diffusion are not removable from the emulsion layer by washing.
- the said new color couplers may further .be
- colloid layer used in the developing solution or in a colloid layer, in the latter case either in a lightg-sensitive layer or in a non-light-sensitive layer adjacent to a sensitive layer or separated therefrom by a water-permeable colloid layer.
- the aromatic amino compounds which may be used as developing agent in. accordance with the present invention include the mono-, diand tri-amino aryl compounds.
- the monoamino developing agents may be .mentioned scope thereof.
- Example 1 1.1 g. indazolone according to Formula IV:
- Example 2 1 g. 4-chloro-indazolone according to Formula V:
- Example 3 11 g. 3.5dichloro-2-amino benzoic acid are dissolved in 50 cc. of a concentrated aqueous so- .lution of hydrochloric acid and 350 cc. water.
- Example 5 8.5 g. 4-sulfo-1-amino benzol-2-carboxylic acid are dispersed in 32 cc. of a concentrated aqueous solution of hydrochloric acid. successively, 64 cc. of an aqueous solution of sodium nitrite 5% are added to the suspension, and then 225 cc. water. The whole is brought slowly into 480 cc. of a solution of S02 while S02 gas is continuously conducted into that solution. After complete addition, S02 is introduced for yet half an hour. Next, the volume of the mixture is reduced to about 150 cc. by evaporation. The mixture is cooled and filtered with suction. The product separated is'recrystallized in a little amount of water. It melts above 300 C. and is believed to be indazolone-5-sulfonic acid corresponding to Formula VIII:
- An exposedpositive motion picture film is developed in the color developer thus prepared and a bluish magenta image is formed.
- Example 6 6.6 g. B-amino-indazolone-hydrochloride, prepared according to Berichte (1912) 1107, and 5.1 g. 2-chlorobenzothiazole are dissolved in cc. absolute ethanol. The solution is evaporated on the water bath. The residue is washed by boiling with ether and then with water. The washed residue is dissolved in 200 cc. ethanol. The volume of the solution is reduced to 20 cc. The product which precipitates after cooling is filtered with suction. It melts at 252255 C. After washing by boiling with water and then with acetone, the melting point may be raised to 270-272 C.
- the product is believed to be 6(2'-benzothiazolyl amino)indazolone according to Formula 2 g. of this indazolone derivative are dissolved in 20 cc. of a methanolic solution of potassium hydroxide N and added to 1 litre of a mixture of equal parts of the following solutions:
- Example 8 A mixture of 5.5 g. G-aminoindazolone-hydrochloride, 3.7 g. phthalic acid anhydride and 5 cc. pyridine is heated for 30 minutes at 180 C. on an oil bath. The mixture is cooled and the solid mass obtained is washed by boiling with water and next with acetone. Melting point is 304-305 C. N content calculated 15.05, found 14.79. The product is believed to be fi-phthal-imido indazolone corresponding to Formula X1:
- Example 10 A solution of 1.1 g. 6-amino-indazolone-hydrochloride and 1.1 g. of the copolymer of styrene and maleic acid anhydride in 5.5 cc. pyridine is boiled for 5 hours. The reaction mixture is washed with boiling water, and then with boiling methanol. A product melting above 300 C. and corresponding to Formula XIII:
- Example 11 3.2 g. S-amino-indazolone hydrochloride prepared according to Berichte 75 (1942) 1107, 6 g. stearic acid chloride and 45 cc. pyridine are refluxed for 5 hours. The residue is washed by boiling first with water, then with acetone and finally with methanol. 5 stearoyl-amino indazolone melting at 218-220 C. and corresponding to- Formula XIV:
- Example 12 0.2 g. of the bis-indazolone derivative called hereinafter 5-(indazolonyl-5') -indazolone, corresponding to Formula XV:
- Example 13 0.2 g. 2-6-dimethyl-4-hydrazino nicotinic anhydride corresponding to Formula XVI:
- Example 14 XVII OH-NH 1 g. of this product is dissolved in cc. of an aqueous solution of potassium hydroxide N/2 and added to 100 cc. of an emulsion for positive motion picture film. This emulsion is coated onto a 10 tained by mixing equal parts of the following solutions:
- Example 16 To 14 g. diamino diphenyl methane dicarboxylic acid and 40 cc. concentrated aqueous solution of hydrochloric acid, 35 cc. of an aqueous solution of sodium nitrite 10% are added while cooling with ice. The reaction mixture is filtered. The filtrate is added in 30 minutes drop by drop to 400 cc. of a saturated aqueous solution of sulphurous anhydride while cooling with icewater and conducting S02 into the reaction mixture. After complete addition, introduction of S02 is continued for another 30 minutes. 400 cc. water are then added and the whole is boiled for one hour, whereupon the mixture is filtered and the filtrate cooled. The precipitate is recrystallized from ethyl alcohol. The S-methylene-bis- (indazolone) obtained corresponds to Formula XIX:
- Photographic developer containing a primary aromatic amino developing agent and a color coupler having a formula selected from the group consisting of For'mulaI:
- A'photographicdeveloper containing a primary aromatic amino developing agent and 5- (indazolonyl-B') -indazolone.
- a photographic material comprising a silver halide emulsion layer and a colloid layer, containing an octadecenyl-succinyl-amino-indazolone.
- a photographic material comprising a silver an teutom r c. fo m of o m la I.v wh Z re ent he n n-m atom r ui for co et n an erqm c ucleus,-
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB30406/48A GB663190A (en) | 1948-11-23 | 1948-11-23 | Improvements in and relating to the production of colour photographic images |
| GB23087/51A GB720284A (en) | 1948-11-23 | 1951-10-03 | Improvements in and relating to the production of colour photographic images |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2673801A true US2673801A (en) | 1954-03-30 |
Family
ID=26256320
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US128913A Expired - Lifetime US2673801A (en) | 1948-11-23 | 1949-11-22 | Production of color photographic images |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US2673801A (en(2012)) |
| BE (2) | BE492307A (en(2012)) |
| CH (2) | CH283789A (en(2012)) |
| DE (2) | DE814996C (en(2012)) |
| FR (2) | FR1015150A (en(2012)) |
| GB (2) | GB663190A (en(2012)) |
| NL (4) | NL172896B (en(2012)) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2866706A (en) * | 1952-12-10 | 1958-12-30 | Ici Ltd | Indazolone colour couplers |
| US2872317A (en) * | 1952-03-21 | 1959-02-03 | Ici Ltd | Colour photographic images produced from indazolone colour couplers |
| DE1130287B (de) * | 1961-02-01 | 1962-05-24 | Agfa Ag | Verfahren zur Herstellung von farbenphotographischen Bildern nach dem Verfahren der farbigen Entwicklung und Material zur Durchfuehrung des Verfahrens |
| US3043694A (en) * | 1960-05-23 | 1962-07-10 | Eastman Kodak Co | Novel class of 3-indazolinone developing agent |
| US3284200A (en) * | 1962-06-07 | 1966-11-08 | Ilford Ltd | 3-pyrazolidone developers |
| US3770447A (en) * | 1970-12-29 | 1973-11-06 | Agfa Gevaert Ag | Light-sensitive silver halide color photographic material containing indazolone couplers |
| US4481268A (en) * | 1981-02-09 | 1984-11-06 | Eastman Kodak Company | Method of forming a photographic dye image |
| WO2015123193A1 (en) * | 2014-02-12 | 2015-08-20 | E. I. Du Pont De Nemours And Company | Fungicidal benzodipyrazoles |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2964402A (en) * | 1951-10-03 | 1960-12-13 | Gevaert Photo Prod Nv | Mono-acetyl indazolone color couplers |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US742405A (en) * | 1901-12-17 | 1903-10-27 | Farbenfabriken Elberfeld Co | Photographic plate and process of making same. |
| US2200306A (en) * | 1937-07-23 | 1940-05-14 | Gen Aniline & Film Corp | Compound having reactive methylene groups |
| GB524557A (en) * | 1938-10-26 | 1940-08-08 | Kodak Ltd | Improvements in and relating to photographic materials and the processing thereof |
| US2213986A (en) * | 1938-04-08 | 1940-09-10 | Ilford Ltd | Production of colored photographic images |
| US2353754A (en) * | 1942-11-07 | 1944-07-18 | Eastman Kodak Co | Color photography using metallic salt coupler compounds |
| GB577804A (en) * | 1943-09-27 | 1946-05-31 | Kodak Ltd | Improvements in and relating to the production and processing of photographic materials |
-
0
- BE BE514576D patent/BE514576A/xx unknown
- NL NL717100393A patent/NL150078B/xx unknown
- BE BE492307D patent/BE492307A/xx unknown
- NL NL80779D patent/NL80779C/xx active
- NL NL84810D patent/NL84810C/xx active
- NL NLAANVRAGE7709088,A patent/NL172896B/xx unknown
-
1948
- 1948-11-23 GB GB30406/48A patent/GB663190A/en not_active Expired
-
1949
- 1949-11-21 FR FR1015150D patent/FR1015150A/fr not_active Expired
- 1949-11-22 US US128913A patent/US2673801A/en not_active Expired - Lifetime
- 1949-11-22 CH CH283789D patent/CH283789A/fr unknown
- 1949-11-24 DE DEG457A patent/DE814996C/de not_active Expired
-
1951
- 1951-10-03 GB GB23087/51A patent/GB720284A/en not_active Expired
-
1952
- 1952-10-02 CH CH304621D patent/CH304621A/fr unknown
- 1952-10-02 FR FR64640D patent/FR64640E/fr not_active Expired
- 1952-10-03 DE DEG9910A patent/DE918484C/de not_active Expired
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US742405A (en) * | 1901-12-17 | 1903-10-27 | Farbenfabriken Elberfeld Co | Photographic plate and process of making same. |
| US2200306A (en) * | 1937-07-23 | 1940-05-14 | Gen Aniline & Film Corp | Compound having reactive methylene groups |
| US2213986A (en) * | 1938-04-08 | 1940-09-10 | Ilford Ltd | Production of colored photographic images |
| GB524557A (en) * | 1938-10-26 | 1940-08-08 | Kodak Ltd | Improvements in and relating to photographic materials and the processing thereof |
| US2353754A (en) * | 1942-11-07 | 1944-07-18 | Eastman Kodak Co | Color photography using metallic salt coupler compounds |
| GB577804A (en) * | 1943-09-27 | 1946-05-31 | Kodak Ltd | Improvements in and relating to the production and processing of photographic materials |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2872317A (en) * | 1952-03-21 | 1959-02-03 | Ici Ltd | Colour photographic images produced from indazolone colour couplers |
| US2866706A (en) * | 1952-12-10 | 1958-12-30 | Ici Ltd | Indazolone colour couplers |
| US3043694A (en) * | 1960-05-23 | 1962-07-10 | Eastman Kodak Co | Novel class of 3-indazolinone developing agent |
| DE1130287B (de) * | 1961-02-01 | 1962-05-24 | Agfa Ag | Verfahren zur Herstellung von farbenphotographischen Bildern nach dem Verfahren der farbigen Entwicklung und Material zur Durchfuehrung des Verfahrens |
| US3284200A (en) * | 1962-06-07 | 1966-11-08 | Ilford Ltd | 3-pyrazolidone developers |
| US3770447A (en) * | 1970-12-29 | 1973-11-06 | Agfa Gevaert Ag | Light-sensitive silver halide color photographic material containing indazolone couplers |
| US4481268A (en) * | 1981-02-09 | 1984-11-06 | Eastman Kodak Company | Method of forming a photographic dye image |
| WO2015123193A1 (en) * | 2014-02-12 | 2015-08-20 | E. I. Du Pont De Nemours And Company | Fungicidal benzodipyrazoles |
Also Published As
| Publication number | Publication date |
|---|---|
| DE814996C (de) | 1951-09-27 |
| DE918484C (de) | 1954-09-27 |
| NL172896B (nl) | |
| NL84810C (en(2012)) | |
| BE492307A (en(2012)) | |
| CH283789A (fr) | 1952-06-30 |
| GB720284A (en) | 1954-12-15 |
| GB663190A (en) | 1951-12-19 |
| BE514576A (en(2012)) | |
| NL80779C (en(2012)) | |
| FR64640E (fr) | 1955-11-30 |
| FR1015150A (fr) | 1952-08-27 |
| CH304621A (fr) | 1955-01-15 |
| NL150078B (nl) |
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