US2293004A - Photographic color picture - Google Patents
Photographic color picture Download PDFInfo
- Publication number
- US2293004A US2293004A US265601A US26560139A US2293004A US 2293004 A US2293004 A US 2293004A US 265601 A US265601 A US 265601A US 26560139 A US26560139 A US 26560139A US 2293004 A US2293004 A US 2293004A
- Authority
- US
- United States
- Prior art keywords
- emulsion
- hydroxy
- silver halide
- pyridone
- layer
- 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
- 239000000839 emulsion Substances 0.000 description 54
- 229910052709 silver Inorganic materials 0.000 description 33
- 239000004332 silver Substances 0.000 description 33
- -1 silver halide Chemical class 0.000 description 31
- 150000001875 compounds Chemical class 0.000 description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 description 13
- 238000000034 method Methods 0.000 description 10
- 239000000975 dye Substances 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000004305 biphenyl Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- SKYBRLALUDNCSM-UHFFFAOYSA-N 1,1-dimethyl-2-phenylhydrazine Chemical compound CN(C)NC1=CC=CC=C1 SKYBRLALUDNCSM-UHFFFAOYSA-N 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 238000009792 diffusion process Methods 0.000 description 5
- 150000004806 hydroxypyridines Chemical class 0.000 description 5
- GGOZGYRTNQBSSA-UHFFFAOYSA-N pyridine-2,3-diol Chemical class OC1=CC=CN=C1O GGOZGYRTNQBSSA-UHFFFAOYSA-N 0.000 description 5
- GRFNBEZIAWKNCO-UHFFFAOYSA-N 3-pyridinol Chemical compound OC1=CC=CN=C1 GRFNBEZIAWKNCO-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 235000005811 Viola adunca Nutrition 0.000 description 3
- 240000009038 Viola odorata Species 0.000 description 3
- 235000013487 Viola odorata Nutrition 0.000 description 3
- 235000002254 Viola papilionacea Nutrition 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- JTXRCERIDLOGDK-UHFFFAOYSA-N 6-hydroxy-5-phenyl-1h-pyridin-2-one Chemical compound OC1=NC(O)=CC=C1C1=CC=CC=C1 JTXRCERIDLOGDK-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 159000000000 sodium salts Chemical class 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
- WKQDMVRMDXBNLR-UHFFFAOYSA-N 1-hexyl-6-hydroxy-4-methylpyridin-2-one Chemical compound CCCCCCN1C(O)=CC(C)=CC1=O WKQDMVRMDXBNLR-UHFFFAOYSA-N 0.000 description 1
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-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
- QGNQEODJYRGEJX-UHFFFAOYSA-N 4h-isoquinoline-1,3-dione Chemical compound C1=CC=C2C(=O)NC(=O)CC2=C1 QGNQEODJYRGEJX-UHFFFAOYSA-N 0.000 description 1
- KBUWQCXQODASRJ-UHFFFAOYSA-N 6-hydroxy-5-methyl-1h-pyridin-2-one Chemical compound CC1=CC=C(O)N=C1O KBUWQCXQODASRJ-UHFFFAOYSA-N 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- DXTUTXYCHFWRQC-UHFFFAOYSA-N isoquinolin-4-ol Chemical compound C1=CC=C2C(O)=CN=CC2=C1 DXTUTXYCHFWRQC-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B60—VEHICLES IN GENERAL
- B60C—VEHICLE TYRES; TYRE INFLATION; TYRE CHANGING; CONNECTING VALVES TO INFLATABLE ELASTIC BODIES IN GENERAL; DEVICES OR ARRANGEMENTS RELATED TO TYRES
- B60C3/00—Tyres characterised by the transverse section
- B60C3/04—Tyres characterised by the transverse section characterised by the relative dimensions of the section, e.g. low profile
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01G—HORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
- A01G9/00—Cultivation in receptacles, forcing-frames or greenhouses; Edging for beds, lawn or the like
- A01G9/24—Devices or systems for heating, ventilating, regulating temperature, illuminating, or watering, in greenhouses, forcing-frames, or the like
- A01G9/245—Conduits for heating by means of liquids, e.g. used as frame members or for soil heating
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F28—HEAT EXCHANGE IN GENERAL
- F28F—DETAILS OF HEAT-EXCHANGE AND HEAT-TRANSFER APPARATUS, OF GENERAL APPLICATION
- F28F1/00—Tubular elements; Assemblies of tubular elements
- F28F1/02—Tubular elements of cross-section which is non-circular
- F28F1/06—Tubular elements of cross-section which is non-circular crimped or corrugated in cross-section
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A40/00—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production
- Y02A40/10—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production in agriculture
- Y02A40/25—Greenhouse technology, e.g. cooling systems therefor
Definitions
- My present invention relates to the manufacture of photographic color pictures.
- One object of my invention is to provide as the dyestuff former a simple or substituted hydroxypyridine.
- Another object of this invention is to provide as the dyestufi former a compound with a con- 4-methyl-6-hydroxy-2-pyridone.
- the silver halide emulsion having the dyestuil former fast to diffusion may be made into a photographic layer in the known manner and there may be one or several layers on one or both sides of a support superimposed on each other.
- the layers may be used for taking black and white pictures or color pictures.
- the emulsion layers are preferably sensitized for different regions of the spectrum. If desired several dyestuff formers may be contained in one layer and these may be so selected that on development a neutral grey picture is prodensed pyridine ring system having in the pyridine nucleus one or several hydroxy groups.
- the dyestuff former used according to the invention may be substituted in the pyridine ring or in the condensed ring or rings in any desired manner.
- Examples of compounds suitable for the invention are 3-hydroxypyridine, 2.6-dihydroxypyridine, 1-phenyl-6-hydroxy-2-pyridine, 4-hydroxyisoquinoline, 1-(4-carbe thoxy-phenyl) -4-methyl-6-hydroxy-2-pyridone.
- dyestuff formers may be added either to a the developer or to the emulsion.
- color developers for example para-phenylenediamine or a derivative thereof blue or blue-violet dyestufi images are obtained.
- the emulsion layers may also be made in other manner, for example differently sensitized emulsions with different dyestuif formers may be distributed in the form of small particles on a support.
- the color picture may be produced in various ways for example in the manner described in any one of the U. S. Patents 2,179,228, 2,179,238, 2,186,849, 2,178,612 and 2,186,730.
- the pictures may be developed by simple color development or by reversal development, as described in U. S. Patents 2,229,137 and 2,179,234.
- the silver may be removed from the silver halide emulsion layer or the silver may be allowed to remain in the layer together with the dyestuif picture.
- Example 1 To 1 kilo of a silver halide emulsion there are added 5 grams of 3-hydroxypyridine and the emulsion is cast to form a layer. After exposure development with para-dimethylaminoaniline produces a bluedyestuil image.
- Example 2 To 1 kilo of a silver halide emul-- sion there are added 5 grams of 2.6-dihydroxypyridine. This emulsion is cast to form a layer. After exposure development with para-dimethylaminoaniline produces a blue dyestuif image.
- Example 3 To 1 kilo of silver halide emulsion there are added 5 grams of l-phenyl-4-methyl-6-hydroxy-2-pyridone of the formula and the emulsion is cast to form a layer. After exposure and development with para-dimethylaminoaniline a. blue-violet dyestufl image: is ob- H crystallizes.
- Example 5 -1 mol of p-methyl-glutaconic acid is melted together with 1 mol of stearylamine and the mass is dissolved in methanol. From the solution 1-octadecyl-4-methyl-6-hydroxy- 2-pyridone of the formula 0 I nicu-cuiin la crystallizes.
- Example 6 II'o 1 kilooffa silver halide emulsion there is added 1.3-dihydroxy-isoquinoline homo-phthalimide of the formula in the'form of a sodium salt in a quantity of 5 grams and the emulsion is cast to form a layer. After exposure and development with paradimethylaminoaniline a blue dyestufl image is obtained.
- Example 7 1 kilo of the silver halide emulsion there are added 5 grams of the sodium salt of 1.4-diphenyl-6-hydroxy-2-pyridone of the formula is recrystallized from methanol. 5 grams of this compound are added to 1 kilo of a silver halide emulsion and this is cast to form a layer. After exposure development with para-dimethylaminoaniline produces a blue dyestufi image.
- Example 9 The 1 (4 aminodiphenylY- 4 methylr-6-hydroxy-2-pyridone made as described in Example 8 is dissolved in dilute caustic soda lye and to the solution benzoyl chloride is added by drops. 1 (4' benzoylaminodiphenyl) 4 methyl-6-hydroxy-2-pyridone of the formula is precipitated. It is filtered with suction and washed. 5 grams of this compound are added to 1 kilo'of the silver halide emulsion and this is cast to form a layer. After exposure and development with para-dimethylaminoaniline a blue dyestufl' image is obtained.
- Example 10 To 1 kilo of a silver halide emulsion there are added 5 grams of 1-butyl-4- methy1-6-hydroxy-2-pyridone. The emulsion is then cast to form a layer. After exposure development with para dimethylaminoaniline yields a blue dyestufl' image.
- Example 11 To 1 kilo of a silver halide emulsion there are added 5 grams of 1-hexyl-4- methyl-6-hydroxy-2-pyridone. The emulsion is then cast to form a layer. After exposure development wit h para dimethylaminoaniline yields a blue dyestuii' image.
- Example 12 To 1 kilo of a silver halide emulsion there are added 5 grams of 1-octyi-4- methyl-fi-hydroxy-Z-pyridone. The emulsion is After exposure development with para-dimethylaminoaniline yields a blue dyestui! image.
- Example 13 To 1 kilo of a silver halide emulsion there are added 5 grams of 1-dodecyi-4- methyl-6-hydroxy-2-pyridone. The emulsion is then cast to form a layer. After exposure development with para-dimethylaminoaniline yields a blue dyestufl image.
- Example 14 To 1 kilo of a silver halide emulsion there are added 5 grams of l -cyclohexyl-dmethyl-6-hydroxy-2-pyridone. The emulsion is then cast to form a layer, After exposure development with para-dimethylaminoaniline yields a blue dyestufl image.
- Example 15 To 1 kilo of a silver halide emulsion there are added 5 grams of 1-methyl-4- 'phenyl-6-hydroxy-2-pyridone. The emulsion is then cast to form a layer. After exposure development with para -.dimethylaminoaniline phenyl-6-hydroxy-2-pyridone.
- Example 16 --To 1 kilo or a silver halide emulsion there are added 5 grams of 1-butyl-4- phenyl-G-hydroxy-Z-pyridone. The emulsion is then cast to form 'a layer. After exposure development with para-dimethylaminoaniline yields a blue dyestufi image.
- Example 17 To 1 kilo of a silver halide mulsion there are added 5 grams of 1-hexyl-4- The emulsion is then cast to form a layer. After exposure development with para-dimethylaminoaniline yields a blue dyestufl image.
- Example 18 To 1 kilo of a silver halide emulsion there are added 5 grams of 1-octyl-4- phenyl-G-hydroxy-Z-pyridone. The emulsion is then cast to form a layer. After exposure development with para-dimethylamino'aniline yields a blue dyestufi image.
- Example 19 To 1 kilo ofa silver halide emulsion there are added 5 grams of l-dodecyli- The emulsion is then cast to 'form a layer.
- improvement which comprises developing the exposed photographic silver halid emulsion with an aromatic amino developer containing as the dyestufi former a compound selected from the class consisting of hydroxypyridines and hydroxy-2- pyridones in which the N-atom is tertiary.
- the improvement which comprises exposing a photographic silver halide emulsion containing as the dyestufi former a compound selected from the class consisting of hydroxypyridines and hydroxy-2-pyridones in which the ring N-atom is tertiary and developing said emulsion with an aromatic amino developer.
- the improvement which comprises exposing a photographic silver halide emulsion containing as the dyestuif former a compound selected from the class consisting of hydroxypyridines and hydroxy-2-pyridones in which the ring N-atom is tertiary, said compound containing a radicle imparting thereto fastness to diffusion with respect to the binding agent of said emulsion, and developing said emulsion with an aromatic amino developer;
- Silver halide emulsion for color photography containing as a color forming component a compound selected irom the class consisting of hy droxypyridines and hydroxy-Z-pyridones in which the ring N-atom is tertiary, said compound containing a radicle imparting thereto fastness to difiusion with respect to the binding agent of said emulsion.
- a dyestufi forming developer comprising an aqueous olution containing an aromatic amino developing agent and a compound selected from the class consisting of hydrorypyridines and hydroxy-2-pyridones in which the ring N-atom is tertiary.
- Silver halide emulsions for color photography containing as a color forming component a compound selected from the class consisting of hydroxypyridines and hydroxy-2epyridones in which the ring N-atoms is tertiary.
- the improvement which comprises developing an exposed photographic silver halide emulsion with an aromatic amino developer in the presence of a color former selected from the class consisting of hydroxypyridlnes and hydroxy-2-pyridones in which the ring N-atom is tertiary.
- composition as defined in claim' 4 wherein said color former is l-octadecyl-4- methyl-6-hydroiry-2-pyridone.
- composition as defined in claim 4 wherein said color former is 1-(4'-amino-diphenyl) -4-methyl-6-hydroxy-2-pyridone.
- composition as defined in claim 4 wherein said color former is l-octyl-4-methyl-6- hydroxy-Z-pyridone.
Landscapes
- Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Mechanical Engineering (AREA)
- Geometry (AREA)
- Thermal Sciences (AREA)
- General Engineering & Computer Science (AREA)
- General Physics & Mathematics (AREA)
- Soil Sciences (AREA)
- Environmental Sciences (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEI0061027 | 1938-04-07 |
Publications (1)
Publication Number | Publication Date |
---|---|
US2293004A true US2293004A (en) | 1942-08-11 |
Family
ID=7195380
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US265601A Expired - Lifetime US2293004A (en) | 1938-04-07 | 1939-04-01 | Photographic color picture |
Country Status (3)
Country | Link |
---|---|
US (1) | US2293004A (en(2012)) |
BE (1) | BE433687A (en(2012)) |
FR (1) | FR870393A (en(2012)) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2421693A (en) * | 1944-09-16 | 1947-06-03 | Gen Aniline & Film Corp | Imidazolone color formers |
US5202224A (en) * | 1990-01-09 | 1993-04-13 | Fuji Photo Film Co., Ltd. | Dye-forming coupler, a silver halide color photographic material using same, and a method for processing the silver halide color photographic material |
US5260177A (en) * | 1988-03-16 | 1993-11-09 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive material |
-
0
- BE BE433687D patent/BE433687A/xx unknown
-
1939
- 1939-04-01 US US265601A patent/US2293004A/en not_active Expired - Lifetime
- 1939-04-06 FR FR870393D patent/FR870393A/fr not_active Expired
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2421693A (en) * | 1944-09-16 | 1947-06-03 | Gen Aniline & Film Corp | Imidazolone color formers |
US5260177A (en) * | 1988-03-16 | 1993-11-09 | Fuji Photo Film Co., Ltd. | Silver halide color photographic light-sensitive material |
US5202224A (en) * | 1990-01-09 | 1993-04-13 | Fuji Photo Film Co., Ltd. | Dye-forming coupler, a silver halide color photographic material using same, and a method for processing the silver halide color photographic material |
Also Published As
Publication number | Publication date |
---|---|
BE433687A (en(2012)) | |
FR870393A (fr) | 1942-03-10 |
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