GB1244676A - Colour photographic silver halide light-sensitive materials - Google Patents
Colour photographic silver halide light-sensitive materialsInfo
- Publication number
- GB1244676A GB1244676A GB39852/69A GB3985269A GB1244676A GB 1244676 A GB1244676 A GB 1244676A GB 39852/69 A GB39852/69 A GB 39852/69A GB 3985269 A GB3985269 A GB 3985269A GB 1244676 A GB1244676 A GB 1244676A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amylphenoxy
- tert
- prepared
- chloro
- acid
- 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 4
- 239000000463 material Substances 0.000 title 1
- 229910052709 silver Inorganic materials 0.000 title 1
- 239000004332 silver Substances 0.000 title 1
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- 150000002828 nitro derivatives Chemical class 0.000 abstract 2
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 abstract 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- NRHMEGHSJZMDFQ-UHFFFAOYSA-N 2,4,4-trimethyloct-1-ene Chemical compound CCCCC(C)(C)CC(C)=C NRHMEGHSJZMDFQ-UHFFFAOYSA-N 0.000 abstract 1
- NDHDBYBYUGLUJG-UHFFFAOYSA-N 2-[2,4-bis(2-methylbutan-2-yl)phenoxy]-n-(4-chloro-3-nitrophenyl)butanamide Chemical compound C=1C=C(Cl)C([N+]([O-])=O)=CC=1NC(=O)C(CC)OC1=CC=C(C(C)(C)CC)C=C1C(C)(C)CC NDHDBYBYUGLUJG-UHFFFAOYSA-N 0.000 abstract 1
- PHCYXPLSQNMCRY-UHFFFAOYSA-N 2-[2,4-bis(2-methylbutan-2-yl)phenoxy]butanoic acid Chemical compound CCC(C(O)=O)OC1=CC=C(C(C)(C)CC)C=C1C(C)(C)CC PHCYXPLSQNMCRY-UHFFFAOYSA-N 0.000 abstract 1
- QAUCLWCEEKGYHF-UHFFFAOYSA-N 2-[2-(2,4,4-trimethylpentan-2-yl)phenoxy]acetyl chloride Chemical compound CC(CC(C)(C)C)(C)C1=C(OCC(=O)Cl)C=CC=C1 QAUCLWCEEKGYHF-UHFFFAOYSA-N 0.000 abstract 1
- IUQAZWKZRSYENF-UHFFFAOYSA-N 2-[4-(2-methylbutan-2-yl)-2-(2,4,4-trimethylpentan-2-yl)phenoxy]acetyl chloride Chemical compound CC(CC)(C)C1=CC(=C(OCC(=O)Cl)C=C1)C(CC(C)(C)C)(C)C IUQAZWKZRSYENF-UHFFFAOYSA-N 0.000 abstract 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 abstract 1
- OLRVZGRGURNZAY-UHFFFAOYSA-N 3-[butyl(hexadecanoyl)amino]propanoic acid Chemical compound C(CCC)N(C(CCCCCCCCCCCCCCC)=O)CCC(=O)O OLRVZGRGURNZAY-UHFFFAOYSA-N 0.000 abstract 1
- LDSIOPGMLLPSSR-UHFFFAOYSA-N 3-chloro-4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C(Cl)=C1 LDSIOPGMLLPSSR-UHFFFAOYSA-N 0.000 abstract 1
- FOHHWGVAOVDVLP-UHFFFAOYSA-N 4-chloro-3-nitroaniline Chemical compound NC1=CC=C(Cl)C([N+]([O-])=O)=C1 FOHHWGVAOVDVLP-UHFFFAOYSA-N 0.000 abstract 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract 1
- VXHXZCAECFDBLX-UHFFFAOYSA-N N-(4-chloro-3-nitrophenyl)-2-[4-(2-methylbutan-2-yl)-2-pentan-2-ylphenoxy]acetamide Chemical compound [N+](=O)([O-])C1=C(C=CC(=C1)NC(COC1=C(C=C(C=C1)C(C)(C)CC)C(C)CCC)=O)Cl VXHXZCAECFDBLX-UHFFFAOYSA-N 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 235000010724 Wisteria floribunda Nutrition 0.000 abstract 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 abstract 1
- 229960001413 acetanilide Drugs 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Substances ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract 1
- NGRXSVFCLHVGKU-UHFFFAOYSA-N ethyl 3-(4-nitrophenyl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=C([N+]([O-])=O)C=C1 NGRXSVFCLHVGKU-UHFFFAOYSA-N 0.000 abstract 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- FZERHIULMFGESH-UHFFFAOYSA-N methylenecarboxanilide Natural products CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 abstract 1
- RWYIWRXZUUNTMT-UHFFFAOYSA-N n-(3-amino-4-chlorophenyl)-2-[2,4-bis(2-methylbutan-2-yl)phenoxy]butanamide Chemical compound C=1C=C(Cl)C(N)=CC=1NC(=O)C(CC)OC1=CC=C(C(C)(C)CC)C=C1C(C)(C)CC RWYIWRXZUUNTMT-UHFFFAOYSA-N 0.000 abstract 1
- 239000012074 organic phase Substances 0.000 abstract 1
- NRZWYNLTFLDQQX-UHFFFAOYSA-N p-tert-Amylphenol Chemical compound CCC(C)(C)C1=CC=C(O)C=C1 NRZWYNLTFLDQQX-UHFFFAOYSA-N 0.000 abstract 1
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 238000010792 warming Methods 0.000 abstract 1
- 238000005406 washing Methods 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
-
- 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
- G03C1/00—Photosensitive materials
- G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
- G03C1/815—Photosensitive materials characterised by the base or auxiliary layers characterised by means for filtering or absorbing ultraviolet light, e.g. optical bleaching
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,244,676. Amides. FUJI PHOTO FILM CO. Ltd. 8 Aug., 1969 [10 Aug., 1968],No. 39862/69. Heading C2C. [Also in Division G2] 2 - Nitro - 4 - [2 - (2,4 - di - tert - amylphenoxy)- butyramido] - chlorobenzene is prepared by adding a degassed acid chloride prepared from 2-(2,4- di - tert - amylphenoxy) butyric acid and thionyl chloride to 4 - chloro - 3 - nitroaniline dissolved in acetonitrile. 2 - Amino - 4 - [2- (2,4 - di - tert - amylphenoxy) - butyramido]- chlorobenzene is obtained by catalytic hydrogenation of the above nitro derivative using Raney nickel. 2 - (4 - nitrobenzoyl) - 2<SP>1</SP>- chloro- 5<SP>1</SP> - [2- (2,4 - di - tert - amylphenoxy} - butyramido] - acetanilide is prepared by heating a mixture of ethyl p - nitrobenzoylacetate and the above amine in xylene. 2 - (4 - Aminobenzoyl) - 2<SP>1</SP> - chloro -. 5<SP>1</SP> - [2 - (2,4 - di - tert - amylphenoxy) - butyramido] - acetanilide is prepared by dissolving the above nitro compound in a methanol, acetic acid and water mixture and adding iron powder while stirring and warming. Similarly 2 - nitro - 4 - [2 - (2 - sec - amyl - 4- tert amylphenoxy) - acetamido] - chlorobenzene, 2 - amino - 4 - [2 - (2 - sec - amyl - 4'- tertamylphenoxy)acetamido] - chlorobenzene, 2 - (4- nitrobenzoyl) - 2<SP>1</SP> - chloro - 5<SP>1</SP> - [2 - -'(2 - secamyl - 4 - tert - amylphenoxy) - acetamido]- acetanilide and 2 - (4 - aminobenzoyl) - 2<SP>1</SP> - chloro- 5<SP>1</SP> - [2 - (2 - sec - amyl - 4 - tert - amylphenoxy)- acetamido] - acetanilide are prepared. A similar series of reactions is also disclosed starting from 3 - (N - butylhexadecanamido)- propionic acid (preparation is given in Japanese Patent Publication 23902/67) and thionyl chloride to obtain the corresponding acid chloride which is then further treated as above. 4 - (1,1 - dimethylpropyl) - 2 - (1,1,3,3 - tetramethylbutyl) - phenoxyacetyl chloride and 3- chloro - 4 - nitroaniline (the latter prepared by the process described in the Journal of the Chemical Society, Volume 1928, page 692) are similarly treated to give the corresponding products. 4 - (1,1 - Dimethylpropyi) 2 - (1,1,3,3 - tetramethylbutyl) - phenoxyacetyl chloride is prepared by adding methanolic sulphuric acid dropwise to a mixture of p - t - amylphenol and 2,4,4- trimethyl-1-octene, refluxing the distilled organic phase (after washing with water) with ethylbromoacetate, potassium carbonate and acetone and then forming the acid chloride from the acid so produced by treatment with excess thionyl chloride.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5696568 | 1968-08-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1244676A true GB1244676A (en) | 1971-09-02 |
Family
ID=13042226
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB39852/69A Expired GB1244676A (en) | 1968-08-10 | 1969-08-08 | Colour photographic silver halide light-sensitive materials |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3649276A (en) |
| BE (1) | BE737248A (en) |
| CA (1) | CA926185A (en) |
| DE (1) | DE1940548A1 (en) |
| FR (1) | FR2016920A1 (en) |
| GB (1) | GB1244676A (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5351214Y2 (en) * | 1975-01-16 | 1978-12-07 | ||
| IT1207929B (en) * | 1979-11-09 | 1989-06-01 | S P A 3 M Italia | U.V. ABSORBING COMPOUNDS AND PHOTOGRAPHIC ELEMENTS THAT CONTAIN THEM |
| JPS58208745A (en) * | 1982-05-28 | 1983-12-05 | Konishiroku Photo Ind Co Ltd | Color photographic sensitive material |
| IT1181384B (en) * | 1983-06-07 | 1987-09-23 | Minnesota Mining & Mfg | ULTRAVIOLET ABSORBER AND PHOTOGRAPHIC MATERIAL THAT INCLUDES IT |
| DE3531383A1 (en) * | 1985-09-03 | 1987-03-05 | Agfa Gevaert Ag | PHOTOGRAPHIC RECORDING MATERIAL WITH A UV ABSORBER AND NEW UV ABSORBER |
| DE19539380A1 (en) * | 1995-07-21 | 1998-11-05 | Hubert K Block | Binding strip |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2367036A (en) * | 1940-10-31 | 1945-01-09 | Du Pont | Processes of color photography and compositions and articles therefor utilizing polymeric color formers |
| BE623419A (en) * | 1961-10-10 | |||
| GB1113038A (en) * | 1966-01-24 | 1968-05-08 | Fuji Photo Film Co Ltd | Light sensitive materials containing yellow-forming couplers |
-
1969
- 1969-08-07 CA CA058877A patent/CA926185A/en not_active Expired
- 1969-08-08 FR FR6930716A patent/FR2016920A1/fr not_active Withdrawn
- 1969-08-08 GB GB39852/69A patent/GB1244676A/en not_active Expired
- 1969-08-08 DE DE19691940548 patent/DE1940548A1/en active Pending
- 1969-08-08 BE BE737248D patent/BE737248A/xx unknown
- 1969-08-08 US US848601A patent/US3649276A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE1940548A1 (en) | 1970-03-05 |
| CA926185A (en) | 1973-05-15 |
| FR2016920A1 (en) | 1970-05-15 |
| US3649276A (en) | 1972-03-14 |
| BE737248A (en) | 1970-01-16 |
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