US2992920A - Production of colored photographic images - Google Patents
Production of colored photographic images Download PDFInfo
- Publication number
- US2992920A US2992920A US720013A US72001358A US2992920A US 2992920 A US2992920 A US 2992920A US 720013 A US720013 A US 720013A US 72001358 A US72001358 A US 72001358A US 2992920 A US2992920 A US 2992920A
- Authority
- US
- United States
- Prior art keywords
- quinazolone
- phenyl
- acetamino
- melting
- color
- 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
- -1 2-(BENZOYL-ACETAMINO-PHENYL)-4-QUINAZOLONE Chemical compound 0.000 claims description 25
- QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical compound C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 4
- 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 claims description 4
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 2
- CLTCEJOGPAFBKG-UHFFFAOYSA-N 5-amino-4-phenyl-1h-quinazolin-2-one Chemical compound C1=2C(N)=CC=CC=2NC(=O)N=C1C1=CC=CC=C1 CLTCEJOGPAFBKG-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 150000005130 benzoxazines Chemical class 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- PXBFMLJZNCDSMP-UHFFFAOYSA-N 2-Aminobenzamide Chemical class NC(=O)C1=CC=CC=C1N PXBFMLJZNCDSMP-UHFFFAOYSA-N 0.000 description 1
- XLCWFYGVARZILQ-UHFFFAOYSA-N 2-[benzoyl(nitro)amino]benzamide Chemical compound [N+](=O)([O-])N(C=1C(C(=O)N)=CC=CC1)C(C1=CC=CC=C1)=O XLCWFYGVARZILQ-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
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 1
- UKEXFPMVJDDZBO-UHFFFAOYSA-N 6-benzamido-6-nitrocyclohexa-2,4-diene-1-carboxylic acid Chemical compound [N+](=O)([O-])C1(C(C(=O)O)C=CC=C1)NC(C1=CC=CC=C1)=O UKEXFPMVJDDZBO-UHFFFAOYSA-N 0.000 description 1
- 239000004133 Sodium thiosulphate Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 159000000000 sodium salts Chemical class 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
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
- Yellow colored images are usually obtained by de- Welopment in the presence of compounds which contain an active methylene group, particularly acylacetanilide derivatives.
- a reducible "silver salt image is developed with ;an aromatic aminowdeveloping agent in the presence of a compound according to the formula: i
- the ketodiazine nucleus may be for example 4-pyrirnidone or 4-quinazolone.
- the sodium salt of anthranilic acid is condensed with 0-, mor p-nitrobenzoylchloride.
- the resulting amide is treated with acetic anhydride, thus looses a molecule of water and is converted into a nitrophenylbenzoxazine compound.
- This compound is converted with ammonium hydroxide and pyridine into nitrobenzoylanthranilamide which by boiling in diluted sodium hydroxide is converted into nitrophenylquinazolone.
- the latter is reduced with hydrogen and Raney nickel to the corresponding aminophenyl quinazolone which by condensation with XCH COOC H gives the desired coupler.
- metaand para-nit-robenzoylanthranilic acid obtained according to M. Bogert, R. Gortner and C. Amend, J.A.C.S. 33(1911), 952 may be converted into 2-(mand p-nitrophenyl)benzoxazine according to the same authors.
- the corresponding o-compound may be obtained as follows: o-nitro-benzoylanthranilic acid obtained. according to H. Meyer, Ann. 351 (1907), 273, may be converted into 2-(o-nitrophenyl)benzoxazine according to G. schroeter and O. Eisleb, Ann. 367(1909), 132.
- p-nitrobenzoylanthranilamide .melting at 242 C.
- o-nitro-benzoylanthranilarnide melting at 192 C.
- These anthranilamides may be converted into quinazolones.
- m-nitrobenzoylanthranilamide is refluxed with sodium hydroxide N.
- the reaction mixture is acidified with hydrochloric acid and the precipitate is recrystallized from dimethyl-formamide. Small yellow needles of Z-(m-nitrophenyl)quinazolone, melting above 300 C., are obtained.
- 2-(p-nitrophenyl)-quinazolone is dissolved in a mixtune on? piperidine and Water (equal parts by volume) and reduced in the presence of Raney nickel by hydrogen under a pressure of 30 kg. per sq. cm. and at 75 C. until the theoretical absorption of hydrogen has taken place.
- the reaction mixture is concentrated in vacuum and acidified with acetic acid.
- 2-(m-nitrophenyl)quinazolone is reduced in sodium hydroxide N by hydrogen under a pressure of 3 "kg; per sq. .cm. at 5.0-" C; in the presence .ofRaney nickel.
- the reaction mixture is acidified with hydrochloric acid A precipitate is formed by addition of ammonium hydroxide.
- the resulting 2- (m-aminophenyDquinazolone melts at 251 C.
- 2-(o-nitrophenyl)quinazolone is reduced in dimethylforrnamide in the presence of Raney nickel by hydrogen under a pressure of kg. per sq. cm. at 70 C.
- the resulting 2-(o-aminophenyl)quinazolone melts at 27.5- 227 C.
- couplers may be prepared as follows:
- the said quinazolones are refluxed in dimethylformamide together with an excess of 10-15% of beta-ketcester.
- the resulting beta-keto-anilide precipitates, is washed with methanol and recrystallized from glycolrnet'hyl ether or dimethyl-for-mamide.
- color couplers may arise from adding to the developer a compound which differs from the color coupler only because in the active CH -grou-p one or two hydrogen atoms are replaced by a group capable of splitting off either before development occurs by the action of the alkali in the developing solution or during the color-development.
- aromatic amino compounds which according to our invention are used as developing agents, comprise mono-, diand tri-amino aryl compounds, particularly NzN-dialkyl-para-phenylene diamines and derivatives such as NrN-dialkyl-N'-sulphomethyl-para-phenylene diamines.
- mono-amino developers may be mentioned amino phenols and arnino-cresols and their halogen den'vatives, and also amino-naphthols.
- An exposed photographic film strip coated with a silver halide emulsion layer is developed in a bath of the following composition:
- One of the couplers 1 to' 7 prepared as described above 1 Water to 50 cmfi.
- Solution B is added to'Solution A and water is added to the resulting solution to 1,000 cm.*.
- a yellow image is obtained.
- We claim: 7 1. Process for obtaining a colored photographic image, comprising developing an image consisting of a reducible silver salt with a color forming developer'com tainin-g an N,N-dialkyl-para-pheny1ene diamine as a developing agent, and a quinazolone color coupler selected from the group consisting of 2-(benzoyl-acetamino-phenyl)-4-quinazolone, 2-[m(p-anisoyl-acetamino)-phenyl]- 4 quinazolone, 2 (m-acetyl-acetamino-phenyl) -4-quinazolone, Z-[m-(alpha-furoyl-acetamino)phenyl]-4-quinazolone, and 2-[m-(alpha-thenoyl-acetamino)phenyl]-4- quinazolone.
- Photographic developer containing an N,N-dialkylpara-phenylene diamine as a developing agent, and a quinazolone compound as a color coupler, said quinazolone compound being selected from the group consisting of Z-(benzoyl-acetamiino-phenyl)-4-quinazolone, 2-1[m-' (p-anisoyl-acetamino)phenyl]-4-quinazolone, 2 (m-acetyl-acetamino-phenyl) -4-quinazolone, 2 [m (alpha-furoyl-acetamino)phenyl]-4-quinazolone, and Z-[m-(alphathenoyl-acetamino)-pheny1] -4-quinazolone.
- Process for obtaining a colored photographic image comprising developing an image consisting of a reducible silver salt with a color forming developer containing an N,N-dialkyl-para-phenylene diamine as a developing agent, and 2 (benzoyl-acetamino-phenyl)-4- quinazolone as a color coupler.
- Photographic developer containing an N,N-dialkyl para-pheny-lene diamine as a developing agent, and 2- (benzoyl-acetamino-phenyl) 4-quinazolone as a color coupler.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8588/57A GB856158A (en) | 1957-03-15 | 1957-03-15 | Improvements in or relating to the production of coloured photographic images |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2992920A true US2992920A (en) | 1961-07-18 |
Family
ID=9855376
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US720013A Expired - Lifetime US2992920A (en) | 1957-03-15 | 1958-03-10 | Production of colored photographic images |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US2992920A (en)) |
| BE (1) | BE565656A (en)) |
| FR (1) | FR1201538A (en)) |
| GB (1) | GB856158A (en)) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3161512A (en) * | 1959-12-23 | 1964-12-15 | Ilford Ltd | Colour couplers and their production and use in colour photography |
| US3645742A (en) * | 1968-01-05 | 1972-02-29 | Agfa Gevaert Nv | Color photography |
| US4057432A (en) * | 1970-12-26 | 1977-11-08 | Konishiroku Photo Industry Co., Ltd. | Acylacetanilide coupler with heterocyclic diacyl amino coupling-off group |
| US20100137387A1 (en) * | 2007-05-03 | 2010-06-03 | Neurosearch A/S | Beta-keto-amide derivatives useful as ion channel modulators |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI70036C (fi) * | 1980-01-31 | 1986-09-12 | Ciba Geigy Ag | Kromogena kinazolinfoereningar |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2500487A (en) * | 1948-11-09 | 1950-03-14 | Gen Aniline & Film Corp | Yellow diffusion-fast color formers of the benzimidazole class |
| US2668112A (en) * | 1950-12-20 | 1954-02-02 | Gevaert Photo Prod Nv | Manufacture of photographic color images |
-
0
- BE BE565656D patent/BE565656A/xx unknown
-
1957
- 1957-03-15 GB GB8588/57A patent/GB856158A/en not_active Expired
-
1958
- 1958-03-10 US US720013A patent/US2992920A/en not_active Expired - Lifetime
- 1958-03-14 FR FR1201538D patent/FR1201538A/fr not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2500487A (en) * | 1948-11-09 | 1950-03-14 | Gen Aniline & Film Corp | Yellow diffusion-fast color formers of the benzimidazole class |
| US2668112A (en) * | 1950-12-20 | 1954-02-02 | Gevaert Photo Prod Nv | Manufacture of photographic color images |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3161512A (en) * | 1959-12-23 | 1964-12-15 | Ilford Ltd | Colour couplers and their production and use in colour photography |
| US3645742A (en) * | 1968-01-05 | 1972-02-29 | Agfa Gevaert Nv | Color photography |
| US4057432A (en) * | 1970-12-26 | 1977-11-08 | Konishiroku Photo Industry Co., Ltd. | Acylacetanilide coupler with heterocyclic diacyl amino coupling-off group |
| US20100137387A1 (en) * | 2007-05-03 | 2010-06-03 | Neurosearch A/S | Beta-keto-amide derivatives useful as ion channel modulators |
Also Published As
| Publication number | Publication date |
|---|---|
| GB856158A (en) | 1960-12-14 |
| FR1201538A (fr) | 1959-12-30 |
| BE565656A (en)) |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US2592364A (en) | p-phenylenediamine developer containing alkylacylamidoethyl or alkylacylamidoethoxyring substituents | |
| US2524725A (en) | Magenta phenazonium dyestuff images from 8-hydroxyquinoline couplers | |
| US3446622A (en) | Process for the preparation of color images using 2 - ureido phenolic couplers | |
| GB562205A (en) | Improvements in and relating to colour forming development and colour photographic elements | |
| US2455169A (en) | Colored couplers | |
| US3996253A (en) | Process for the preparation of color images | |
| US2992920A (en) | Production of colored photographic images | |
| US2412700A (en) | Thioglycolic amides | |
| US2324123A (en) | Fog inhibitor for photographic developers | |
| US3013879A (en) | Production of color photographic images | |
| US3245787A (en) | Production of color photographic images | |
| US2592363A (en) | P-phenylenediamine developer containing nu-alkylacetamido ethyl substituent | |
| US4446216A (en) | Photographic material | |
| US3222176A (en) | Photographic colour images from amino substituted phenols | |
| US2271229A (en) | Fog inhibitor for photographic developers | |
| US2668112A (en) | Manufacture of photographic color images | |
| US2979405A (en) | Light-sensitive photographic element containing a 1-hydroxy-2-naphthoic acid anilidecolor coupler | |
| US2902366A (en) | Acylated 3-aminopyrazolone couplers | |
| US3892576A (en) | Photographic water-insoluble compounds having a hydrophobic diffusion-fast substituent | |
| US2897079A (en) | Production of colored photographic images with oxodiazole couplers | |
| US2695234A (en) | Photographic development | |
| US4426444A (en) | Hydroquinone derivatives and their use in photographic materials | |
| US2375344A (en) | Color couplers for color development | |
| US3028237A (en) | Masking of cyan images in color photography | |
| US2868829A (en) | Colour photography |