GB1351395A - Photographic silver halide emulsions containing a yellow coupler - Google Patents
Photographic silver halide emulsions containing a yellow couplerInfo
- Publication number
- GB1351395A GB1351395A GB1383772A GB1383772A GB1351395A GB 1351395 A GB1351395 A GB 1351395A GB 1383772 A GB1383772 A GB 1383772A GB 1383772 A GB1383772 A GB 1383772A GB 1351395 A GB1351395 A GB 1351395A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tetradecyloxybenzoyl
- prepared
- methyl
- boiling
- chloroacetanilide
- 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
- -1 silver halide Chemical class 0.000 title abstract 9
- 239000000839 emulsion Substances 0.000 title 1
- 229910052709 silver Inorganic materials 0.000 title 1
- 239000004332 silver Substances 0.000 title 1
- 238000009835 boiling Methods 0.000 abstract 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 abstract 2
- BIHLZWLBGMIQSN-UHFFFAOYSA-N 2-tetradecoxybenzoic acid Chemical compound CCCCCCCCCCCCCCOC1=CC=CC=C1C(O)=O BIHLZWLBGMIQSN-UHFFFAOYSA-N 0.000 abstract 2
- ZIWRQXKJHNXOTA-UHFFFAOYSA-N 2-tetradecoxybenzoyl chloride Chemical compound CCCCCCCCCCCCCCOC1=CC=CC=C1C(Cl)=O ZIWRQXKJHNXOTA-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- 238000001816 cooling Methods 0.000 abstract 2
- 239000005457 ice water Substances 0.000 abstract 2
- ONWLNVBODYFXCJ-UHFFFAOYSA-N methyl 2-tetradecoxybenzoate Chemical compound CCCCCCCCCCCCCCOC1=CC=CC=C1C(=O)OC ONWLNVBODYFXCJ-UHFFFAOYSA-N 0.000 abstract 2
- NUYRVTHCWWOKQL-UHFFFAOYSA-N methyl 3-oxo-3-(2-tetradecoxyphenyl)propanoate Chemical compound COC(CC(C1=C(C=CC=C1)OCCCCCCCCCCCCCC)=O)=O NUYRVTHCWWOKQL-UHFFFAOYSA-N 0.000 abstract 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 abstract 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 abstract 2
- 238000003756 stirring Methods 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- KOFZTCSTGIWCQG-UHFFFAOYSA-N 1-bromotetradecane Chemical compound CCCCCCCCCCCCCCBr KOFZTCSTGIWCQG-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- ROMKXWPGOILXHH-UHFFFAOYSA-N ethyl 3-oxo-2-(2-tetradecoxybenzoyl)butanoate Chemical compound C(C)OC(C(C(=O)C)C(C1=C(C=CC=C1)OCCCCCCCCCCCCCC)=O)=O ROMKXWPGOILXHH-UHFFFAOYSA-N 0.000 abstract 1
- JDPRRECMRPCSIF-UHFFFAOYSA-N ethyl 3-oxobutanoate;sodium Chemical compound [Na].CCOC(=O)CC(C)=O JDPRRECMRPCSIF-UHFFFAOYSA-N 0.000 abstract 1
- 125000004494 ethyl ester group Chemical group 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 229960001047 methyl salicylate Drugs 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract 1
- 239000008096 xylene Substances 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
- G03C7/36—Couplers containing compounds with active methylene groups
- G03C7/362—Benzoyl-acetanilide couplers
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Abstract
1351395 Alkoxy - benzoyl - acetanilides and intermediates therefor AGFA-GEVAERT AG 24 March 1972 [25 March 1971] 13837/72 Heading C2C [Also in Division G2] 2 - Tetradecyloxybenzoyl - 4<SP>1</SP>- methylacetanilide is prepared by boiling 4-aminotoluene and methyl 2 - tetradecyloxybenzoylacetate in xylene. Methyl 2-tetradecyloxybenzoylacetate is prepared by boiling α-(2-tetradecyloxybenzoyl) acetoactic acid ethyl ester, 30% by weight sodium methoxide solution and methanol, pouring into water, acidifying and extracting with ether. α - (2 - Tetradecyloxybenzoyl)acetoacetic acid ethyl ester is prepared by boiling 2-tetradecyloxybenzoyl chloride and sodium acetoacetic acid ethyl ester in benzene, pouring into ice water, and acidifying with 10% by weight hydrochloric acid. 2-Tetradecyloxybenzoyl chloride is prepared by adding thionyl chloride to fused 2 - tetradecyloxybenzoic acid. 2 - Tetradecyloxybenzoic acid is prepared by refluxing methyl 2 - tetradecyloxybenzoate dissolved in ethanol with aqueous potassium hydroxide, stirring into water and acidifying with 10% by weight hydrochloric acid. Methyl 2-tetradecyloxybenzoate is prepared by boiling sodium metal dissolved in ethylene glycol monomethyl ether followed by the addition of methyl salicylate in ethylene glycol monomethyl ether, adding tetradecylbromide dropwise, boiling, cooling and stirring into water. 2 - Tetradecyloxybenzoyl - 2<SP>1</SP>- methoxyacetanilide 2 - tetradecyloxybenzoyl - 2<SP>1</SP> - chloro- 5<SP>1</SP> - N - methylsulphamyl - acetanilide and 2- tetradecyloxybenzoyl - 4<SP>1</SP>- methyl - sulphonyl acetanilide are prepared in a similar manner to 2- tetradecyloxybenzoyl - 4<SP>1</SP>- methylacetanilide. 2 - Tetradecyloxybenzoyl - 4<SP>1</SP>- methyl - chloroacetanilide is prepared by adding dropwise sulphuryl chloride in chloroform while cooling with ice water to 2-tetradecyloxybenzoyl-4<SP>1</SP>- methylacetanilide in chloroform. 2 - Tetradecyloxybenzoyl - 2<SP>1</SP> - methoxy - chloroacetanilide, 2 - tetradecyloxybenzoyl - 2<SP>1</SP> - chloro - 5<SP>1</SP> - N- methylsulphamyl - chloroacetanilide and 2 - tetradecyloxybenzoyl - 4<SP>1</SP>- methylsulphonyl - chloroacetanilide are prepared similarly.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2114577A DE2114577C3 (en) | 1971-03-25 | 1971-03-25 | Color photographic recording material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1351395A true GB1351395A (en) | 1974-04-24 |
Family
ID=5802772
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1383772A Expired GB1351395A (en) | 1971-03-25 | 1972-03-24 | Photographic silver halide emulsions containing a yellow coupler |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3849140A (en) |
| BE (1) | BE780672A (en) |
| DE (1) | DE2114577C3 (en) |
| FR (1) | FR2130713B1 (en) |
| GB (1) | GB1351395A (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH627562A5 (en) | 1977-04-29 | 1982-01-15 | Ciba Geigy Ag | COLOR PHOTOGRAPHIC MATERIAL. |
| FR2405504A1 (en) * | 1977-10-07 | 1979-05-04 | Agfa Gevaert | YELLOW CHROMOGENOUS COPULANTS FOR SILVER HALIDE PHOTOGRAPHY |
| JPS557702A (en) * | 1978-06-01 | 1980-01-19 | Konishiroku Photo Ind Co Ltd | Silver halide color photographic material |
| DE3313721A1 (en) * | 1983-04-15 | 1984-10-18 | Agfa-Gevaert Ag, 5090 Leverkusen | COLOR PHOTOGRAPHIC COLOR COUPLING RECORD MATERIAL |
| JPS6069653A (en) * | 1983-09-27 | 1985-04-20 | Fuji Photo Film Co Ltd | Formation of color image |
| AU5455698A (en) * | 1996-11-21 | 1998-06-10 | Applied Imaging Corporation | Photographic color couplers used as cytochemical contrast markers |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2407210A (en) * | 1944-04-14 | 1946-09-03 | Eastman Kodak Co | Color couplers |
| GB1052488A (en) * | 1964-02-01 | |||
| BE757638A (en) * | 1969-10-17 | 1971-04-01 | Fuji Photo Film Co Ltd | LIGHT-SENSITIVE MATERIAL FOR COLOR PHOTOGRAPHY, CONTAINING A NEW YELLOW CHROMOGENIC COUPLER |
-
1971
- 1971-03-25 DE DE2114577A patent/DE2114577C3/en not_active Expired
-
1972
- 1972-03-15 BE BE780672A patent/BE780672A/en unknown
- 1972-03-22 US US00236972A patent/US3849140A/en not_active Expired - Lifetime
- 1972-03-24 GB GB1383772A patent/GB1351395A/en not_active Expired
- 1972-03-24 FR FR7210558A patent/FR2130713B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| BE780672A (en) | 1972-09-15 |
| DE2114577A1 (en) | 1972-10-05 |
| DE2114577C3 (en) | 1981-12-03 |
| FR2130713A1 (en) | 1972-11-03 |
| US3849140A (en) | 1974-11-19 |
| FR2130713B1 (en) | 1977-04-01 |
| DE2114577B2 (en) | 1981-04-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| 746 | Register noted 'licences of right' (sect. 46/1977) | ||
| PCNP | Patent ceased through non-payment of renewal fee |