US2921851A - Production of yellow dye images by color development - Google Patents
Production of yellow dye images by color development Download PDFInfo
- Publication number
- US2921851A US2921851A US726288A US72628858A US2921851A US 2921851 A US2921851 A US 2921851A US 726288 A US726288 A US 726288A US 72628858 A US72628858 A US 72628858A US 2921851 A US2921851 A US 2921851A
- Authority
- US
- United States
- Prior art keywords
- naphthol
- color
- yellow
- amino
- images
- 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
- 239000001043 yellow dye Substances 0.000 title description 9
- 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 title description 7
- 238000004519 manufacturing process Methods 0.000 title description 4
- -1 SILVER HALIDE Chemical class 0.000 claims description 53
- 229910052709 silver Inorganic materials 0.000 claims description 12
- 239000004332 silver Substances 0.000 claims description 12
- 239000000975 dye Substances 0.000 claims description 11
- 239000000839 emulsion Substances 0.000 claims description 11
- JSYBAZQQYCNZJE-UHFFFAOYSA-N 1,2,4-benzenetriamine Natural products NC1=CC=C(N)C(N)=C1 JSYBAZQQYCNZJE-UHFFFAOYSA-N 0.000 claims description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000007787 solid Substances 0.000 description 13
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 12
- 238000001914 filtration Methods 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 8
- 235000011054 acetic acid Nutrition 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 229950011260 betanaphthol Drugs 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000012065 filter cake Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- QFFVPLLCYGOFPU-UHFFFAOYSA-N barium chromate Chemical compound [Ba+2].[O-][Cr]([O-])(=O)=O QFFVPLLCYGOFPU-UHFFFAOYSA-N 0.000 description 2
- 239000007844 bleaching agent Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- BWGYGWYDRUDOSS-UHFFFAOYSA-N n-(6-hydroxynaphthalen-1-yl)acetamide Chemical compound OC1=CC=C2C(NC(=O)C)=CC=CC2=C1 BWGYGWYDRUDOSS-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000005406 washing Methods 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
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 1
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 1
- NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 description 1
- VDBJCDWTNCKRTF-UHFFFAOYSA-N 6'-hydroxyspiro[2-benzofuran-3,9'-9ah-xanthene]-1,3'-dione Chemical compound O1C(=O)C2=CC=CC=C2C21C1C=CC(=O)C=C1OC1=CC(O)=CC=C21 VDBJCDWTNCKRTF-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000005618 Fries rearrangement reaction Methods 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000630665 Hada Species 0.000 description 1
- YVYHZWMPYKFUBT-UHFFFAOYSA-N N-[6-hydroxy-5-(4-methoxybenzoyl)naphthalen-1-yl]acetamide Chemical compound C(C)(=O)NC1=C2C=CC(=C(C2=CC=C1)C(C1=CC=C(C=C1)OC)=O)O YVYHZWMPYKFUBT-UHFFFAOYSA-N 0.000 description 1
- 238000003436 Schotten-Baumann reaction Methods 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000628 margaroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001419 myristoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000004060 quinone imines Chemical class 0.000 description 1
- 239000001008 quinone-imine dye Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- G03C7/3244—Couplers forming azinic dyes; Specific developers therefor
Definitions
- This invention relates to the preparation of photographic yellow dye images by photographic color-forming development.
- the color formers embraced by the above formula are new entities in that the prior art does not show 5-amin'o Z-naphthols acylated with aroyl groups in thel-position.
- the resulting S-acetamido-l-aroyl-Z-naphthol is then treated with an acid or base to hydrolyze the acetamido group to the free amine in order to obtain the S-amino-l-aroyl-Z-naphthol.
- the color formers as herein described can either be incorporated in the emulsion or in the developer. If the former is desired, the color former should contain a group to prevent diffusion or wandering from its location in the photographic emulsions. Examples of such non-diffusing color formers are represented by compounds of Formulae 6, 7, 8 and'9. I This invention may be carried out so as to use the color developing method for producing colored negatives, colored positives, or reverse images. These methods are general and conventional in the art and their efiicacy is dependent upon the point at which color development takes place.
- the filtrate was. warmed and diluted with an equal volume of water, then set aside to. cool and crystallize. After chilling; the crystalline solids were collected on a Biichner funnel, washed once with aqueous methanol and dried. The yield of orangeyellow product was 87% of theory.
- Example 11 fi-AMING-I-Q-CHLOROBENZOYD2-NAPHTHOL- COMPOUND 2 1-(2-chlorobenzoyl)-5-acetamido-2-naphthol (0.5 g.) was placed in a 50 ml. round bottom flask with 25 ml. of a mixture consisting of equalvolumes of ethanol and concentrated hydrochloric acid. After refluxing for 2-3 5 hours, the solution was allowed to cool and made alkaline with 6 N sodium hydroxide solution. After charcoaling and filtering, the filtrate was acidified with acetic acid.
- the orange-red product was collected by filtration, Washed with water and recrystallized by dissolving in a small 10 amount of boiling methanol, diluting to cloud point with water, and setting aside to cool and crystallize.
- the yield of brick-red product was 0.3 g. with a melting point of 155 C.
- orange filtrate was acidified with acetic acid and the resulting solids collected and washed with water.
- the wet filter cake was dissolved in about 100 ml. of hot methanol, charcoaled and filtered.
- the filtrate was diluted with an equal volume of hot water and set aside to cool and crystallize;
- the yield of orange colored product was 2.1 g. and had a melting point of 200 C. l Analysis.Nitro2en-calc.: 5.01. Found: 5.04.
- Example IV 5-AMINO-1-PMETHOXYBENZOYL-g-NAPHTHOL- COMPOUND 4 OOHa I i OH NH Q5 2
- 1-(4-methoxybenzoyl)-5-acetamido-2-naphthol (2.5 g.) was placed in a flask containing 20 ml. of a solution consisting of equal volumes of, ethanol and hydrochloric acid.
- the resulting solution was refluxed for three hours 10 and then made alkaline with 6 N sodium hydroxide solution.
- the filtrate was acidified with acetic acid, the solids collected by filtration and washed with water.
- the damp filter cake was recrystallized from acetic acid.
- the yield of crystalline 3; product was 0.3 g. with a. meltingpoint of 235 C.
- hydrous aluminum chloride (0.2 mole) was then added portionwise with stirring. When the addition was completed, the reaction was heated on a steam bath for 1 hour. The resulting dark reaction "mixture was poured into about 250 ml. of ice and hydrochloric acid, diluted to about 7 50 mlQand made strongly alkaline with sodium hydroxide solution. After filtering from a slight amount of insoluble material, the layers were separated and the aqueous phase acidified with aceticacid. After collecting the resulting solids on 'a Biichner funnel and washing with water, the damp cake was dissolved in about 250 ml. of hot pyridine containing a small amount of acetic acid, charcoaled and filtered. The hot filtrate was diluted to the cloud point with water and set aside to cool and crystallize. ice and the solids collected by filtration, washed with diluted ethanol, and dried. The yield of pale yellow 7 crystalline produce was 53.3% of theory.
- The mixture was then chilled in Into a 100 ml., 3-necked flask, fitted with a stirrer and thermometer, was placed 25 ml. of dry tetrachloroethane. S-acetamido-Z-naphthol (0.025 mole) was suspended therein followed by 2-chlorobenzoyl chloride (0.025 mole). Anhydrous aluminum chloride powder (0.1 mole) was added portionwise to the chilled suspension (ice bath) with stirring.
- Example X To 100 ml. of a developer solution made up as follows:
- the strip After the strip had been washed free of hypo, it was treated in a 5% solution of sodium carbonate until the reddish-magenta image was completely converted to a brilliant yellow dye image, about 1 minute being sufficient for the conversion.
- the so obtained yellow image was stable to washing and dried, showed excellent light fastness and displayed no tendency to undergo a spectral shift when subjected to conditions as low as pH 5.
- the coupler may be incorporated in the photographic silver halide emulsion in which case one of the non-diffusing type is advantageously employed such as those represented by Formula 7 or 9.
- NHC O CnHas 4. The process of producing yellow azine dyestuff images by color-forming development which comprises exposing a silver halide emulsion and developing the same with a 2,4-diamino-aniline in the presence of a color former having the following formula:
- R is selected from the class consistinglof hy- 6.
- the -proccss as defined inclaim 4owhcrcin thc color dro'gfi, nitro,alkoxy,.alkyl and .-NHR' whcrcinoR' is former has the following formula: :7 selected from the class consisting of alkyl 'and aliphatic l i, I NEcocnHiu, acyl groups. I 5;
- the process as defined in claim 4 whcreinrthe color 5 former has the following formula: 1
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DENDAT1069470D DE1069470B (de) | 1958-04-03 | Photographische Halogensilberemulsion bzw. Entwickler mit einem Farbbildner, der nach der Farbentwickkmg mit einem Entwickler der p-Phenylendiaminreibe ein gelbes Azinfarbs'tofrbild liefert | |
| BE576817D BE576817A (enrdf_load_stackoverflow) | 1958-04-03 | ||
| US726288A US2921851A (en) | 1958-04-03 | 1958-04-03 | Production of yellow dye images by color development |
| GB9839/59A GB865032A (en) | 1958-04-03 | 1959-03-20 | Production of yellow dye images by color development |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US726288A US2921851A (en) | 1958-04-03 | 1958-04-03 | Production of yellow dye images by color development |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2921851A true US2921851A (en) | 1960-01-19 |
Family
ID=24917977
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US726288A Expired - Lifetime US2921851A (en) | 1958-04-03 | 1958-04-03 | Production of yellow dye images by color development |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US2921851A (enrdf_load_stackoverflow) |
| BE (1) | BE576817A (enrdf_load_stackoverflow) |
| DE (1) | DE1069470B (enrdf_load_stackoverflow) |
| GB (1) | GB865032A (enrdf_load_stackoverflow) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR932479A (fr) * | 1940-03-12 | 1948-03-23 | Kodak Pathe | Perfectionnements aux composés organiques employés dans la photographie en couleurs |
| US2525503A (en) * | 1946-01-10 | 1950-10-10 | Gen Aniline & Film Corp | Production of phenazonium dyestuff images |
-
0
- BE BE576817D patent/BE576817A/xx unknown
- DE DENDAT1069470D patent/DE1069470B/de active Pending
-
1958
- 1958-04-03 US US726288A patent/US2921851A/en not_active Expired - Lifetime
-
1959
- 1959-03-20 GB GB9839/59A patent/GB865032A/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR932479A (fr) * | 1940-03-12 | 1948-03-23 | Kodak Pathe | Perfectionnements aux composés organiques employés dans la photographie en couleurs |
| US2525503A (en) * | 1946-01-10 | 1950-10-10 | Gen Aniline & Film Corp | Production of phenazonium dyestuff images |
Also Published As
| Publication number | Publication date |
|---|---|
| BE576817A (enrdf_load_stackoverflow) | |
| DE1069470B (de) | 1959-11-19 |
| GB865032A (en) | 1961-04-12 |
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