GB865032A - Production of yellow dye images by color development - Google Patents
Production of yellow dye images by color developmentInfo
- Publication number
- GB865032A GB865032A GB9839/59A GB983959A GB865032A GB 865032 A GB865032 A GB 865032A GB 9839/59 A GB9839/59 A GB 9839/59A GB 983959 A GB983959 A GB 983959A GB 865032 A GB865032 A GB 865032A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acetamido
- naphthol
- benzoyl chloride
- prepared
- chloride
- 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
Links
- 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 1
- 239000001043 yellow dye Substances 0.000 title 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 6
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 abstract 4
- 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 abstract 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- BILVLCWOQCFECU-UHFFFAOYSA-N 2-(5-acetamidonaphthalen-2-yl)-4-methoxybenzoic acid Chemical compound CC(=O)NC1=CC=CC2=C1C=CC(=C2)C3=C(C=CC(=C3)OC)C(=O)O BILVLCWOQCFECU-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 abstract 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 abstract 1
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 abstract 1
- NXTNASSYJUXJDV-UHFFFAOYSA-N 3-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(C(Cl)=O)=C1 NXTNASSYJUXJDV-UHFFFAOYSA-N 0.000 abstract 1
- NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 abstract 1
- 238000005618 Fries rearrangement reaction Methods 0.000 abstract 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 abstract 1
- 238000003436 Schotten-Baumann reaction Methods 0.000 abstract 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 abstract 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 abstract 1
- -1 benzoyl halide Chemical class 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 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
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Compounds of the general formula: <FORM:0865032/IV (b)/1> wherein R is hydrogen, halogen, nitro, alkoxy, alkyl or -NHR1 where R1 is alkyl or carboxylic acyl, are prepared by acylating 5-acetamido-2-naphthol with the appropriate benzoyl halide in the presence of aluminium chloride, and then hydrolyzing the acetamido group to the free amine with acid or alkali. Examples are given of the reaction of 5-acetamido-2-naphthol with benzoyl chloride, 2-chloro-benzoyl chloride, 4-methyl-benzoyl chloride or 3-nitro-benzoyl chloride and of the hydrolysis of the products to the free amines. Alternatively, the 5-acetamido intermediates may be prepared by a Fries rearrangement of the benzoic acid esters of 5-acetamido-2-naphthols. Thus, 5-acetamido-1-p-methoxybenzoyl - 2 - naphthol is prepared by refluxing 5-acetamido-2-naphthyl-p-methoxybenzoate with aluminium chloride in tetrachloro-ethane. The product may be hydrolyzed to the corresponding 5-amine. 5-acetamido-2-naphthyl-p-methoxybenzoate is prepared by adding anhydrous, aluminium chloride powder to an ice-cold mixture of 5-acetamido-2-naphthol and p-methoxy benzoyl chloride in tetrachloro-ethane. Alternatively, it is suggested that such esters could be made by a Schotten-Baumann reaction using a benzoyl chloride, the naphthol and sodium hydroxide. Specification 640,382 and U.S.A. Specification 2,486,440 are referred to.
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 |
|---|---|
| GB865032A true GB865032A (en) | 1961-04-12 |
Family
ID=24917977
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9839/59A Expired GB865032A (en) | 1958-04-03 | 1959-03-20 | Production of yellow dye images by color development |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US2921851A (en) |
| BE (1) | BE576817A (en) |
| DE (1) | DE1069470B (en) |
| GB (1) | GB865032A (en) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB540636A (en) * | 1940-03-12 | 1941-10-23 | Eastman Kodak Co | Improvements relating to coupling components for use in colour photography |
| US2486440A (en) * | 1946-01-10 | 1949-11-01 | Gen Aniline & Film Corp | Production of phenazonium dyestuff images |
-
0
- BE BE576817D patent/BE576817A/xx unknown
- DE DENDAT1069470D patent/DE1069470B/en 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
Also Published As
| Publication number | Publication date |
|---|---|
| US2921851A (en) | 1960-01-19 |
| BE576817A (en) | |
| DE1069470B (en) | 1959-11-19 |
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