GB1004075A - Improvements in or relating to colour couplers and to their production and use in colour photography - Google Patents
Improvements in or relating to colour couplers and to their production and use in colour photographyInfo
- Publication number
- GB1004075A GB1004075A GB24026/63A GB2402663A GB1004075A GB 1004075 A GB1004075 A GB 1004075A GB 24026/63 A GB24026/63 A GB 24026/63A GB 2402663 A GB2402663 A GB 2402663A GB 1004075 A GB1004075 A GB 1004075A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- compound
- anhydride
- dodecylphenyl
- reacting
- 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
- 150000001875 compounds Chemical class 0.000 abstract 11
- -1 4 - dodecylphenyl Chemical group 0.000 abstract 3
- 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 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- NWZPPGPXGOMWRA-UHFFFAOYSA-N 1,3-dioxo-6-(phenylcarbamoyl)-2-benzofuran-5-carboxylic acid Chemical compound C1(=CC=CC=C1)NC(=O)C1=C(C=C2C(C(=O)OC2=O)=C1)C(=O)O NWZPPGPXGOMWRA-UHFFFAOYSA-N 0.000 abstract 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical group C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 abstract 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 abstract 1
- QNGVNLMMEQUVQK-UHFFFAOYSA-N 4-n,4-n-diethylbenzene-1,4-diamine Chemical compound CCN(CC)C1=CC=C(N)C=C1 QNGVNLMMEQUVQK-UHFFFAOYSA-N 0.000 abstract 1
- LIMVJXPZRVXOEI-UHFFFAOYSA-N 6-(benzylcarbamoyl)-1,3-dioxo-2-benzofuran-5-carboxylic acid Chemical compound C(C1=CC=CC=C1)NC(=O)C1=C(C=C2C(C(=O)OC2=O)=C1)C(=O)O LIMVJXPZRVXOEI-UHFFFAOYSA-N 0.000 abstract 1
- HRCWMIDETNRMLE-UHFFFAOYSA-N 6-(cyclohexylcarbamoyl)-1,3-dioxo-2-benzofuran-5-carboxylic acid Chemical compound C1(CCCCC1)NC(=O)C1=C(C=C2C(C(=O)OC2=O)=C1)C(=O)O HRCWMIDETNRMLE-UHFFFAOYSA-N 0.000 abstract 1
- FMENKFUCKSTCQF-UHFFFAOYSA-N 6-[(4-dodecylphenyl)carbamoyl]-1,3-dioxo-2-benzofuran-5-carboxylic acid Chemical compound C(CCCCCCCCCCC)C1=CC=C(C=C1)NC(=O)C=1C=C2C(C(=O)OC2=O)=CC1C(=O)O FMENKFUCKSTCQF-UHFFFAOYSA-N 0.000 abstract 1
- 101100037762 Caenorhabditis elegans rnh-2 gene Proteins 0.000 abstract 1
- 239000004471 Glycine Substances 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229960004050 aminobenzoic acid Drugs 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- GGAUUQHSCNMCAU-UHFFFAOYSA-N butane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)CC(C(O)=O)C(C(O)=O)CC(O)=O GGAUUQHSCNMCAU-UHFFFAOYSA-N 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 239000012024 dehydrating agents Substances 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical group O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 abstract 1
- 150000004060 quinone imines Chemical class 0.000 abstract 1
- XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 abstract 1
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms
- C07D231/52—Oxygen atom in position 3 and nitrogen atom in position 5, or vice versa
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/89—Benzo [c] furans; Hydrogenated benzo [c] furans with two oxygen atoms directly attached in positions 1 and 3
-
- 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
- G03C7/3212—Couplers characterised by a group not in coupling site, e.g. ballast group, as far as the coupling rest is not specific
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Indole Compounds (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
The invention comprises colour couplers of formula I <FORM:1004075/C2/1> where A is a tetravalent radical selected from <FORM:1004075/C2/2> where n is 0 or 1, B is the residue of a compound BNH2 which will react with the oxidation products of N,N - diethyl - p - phenylenediamine, formed during the development of a silver salt image with that compound, to yield a quinoneimine or azamethine dyestuff, R is alkyl, aralkyl, cycloalkyl or aryl, and Y is a direct linkage, -NHCOCH2-, <FORM:1004075/C2/3> or <FORM:1004075/C2/4> and related compounds of formula II, III or IV: <FORM:1004075/C2/5> <FORM:1004075/C2/6> <FORM:1004075/C2/7> Suitable B residues include those containing a -COCH2CO-, cyanacetyl, phenol or 1-naphthol group or a pyrazolone ring. Compounds in which Y is a direct linkage may be prepared by reacting BNH2 with <FORM:1004075/C2/8> above 100 DEG C. to give a compound of formula I or below 100 DEG C. to give a compound of formula III, or with <FORM:1004075/C2/9> followed by reaction with a dehydrating agent and reaction of the resultant anhydride with RNH2 to give a compound of formula IV and, if a compound of formula II is required treating the compound of formula I, III or IV with alkali and acidifying the product. Compounds of formula I where Y is -NHCOCH2- or <FORM:1004075/C2/100> may be prepared by reacting <FORM:1004075/C2/111> with glycine or an aminobenzoic acid, converting the product to an acid chloride with thionyl chloride and reacting the acid chloride with BNH2. Compounds of formula I where Y is <FORM:1004075/C2/122> may be prepared by reacting <FORM:1004075/C2/133> with nitroaniline, reducing the product to the corresponding amine, converting this to the isocyanate and then reacting with BNH2. Intermediate compounds prepared in examples as above are: (1) 4-(4-dodecylphenyl-aminocarbonyl) - 5 - carboxyphthalic anhydride and N - (4 - dodecylphenyl) pyromellitic monoimide mono - anhydride- (5) 5 - n - octadecyl-aminocarbonyltrimellitic acid and N - n - octadecylpyromellitic monoimide monoanhydride- (8) N(4-6) - cyanoacetylphenyl)pyromellitic monoimide monoanhydride- (9) 5 - benzylaminocarbonyl - 4 - carboxyphthalic anhydride and N - benzylpyromellitic monoimide monoanhydride- (12) 5 - phenylaminocarbonyl - 4 - carboxyphthalic anhydride and N - phenylpyromellitic monoimide monoanhydride- (14) 5-cyclohexylaminocarbonyl - 4 - carboxyphthalic anhydride and N - cyclohexylpyromellitic monoimide monoanhydride- (15) the monopotassium salt of N-(4-dodecylphenyl)butane 1,2,3,4-tetracarboxylic acid 1,2 - imide and N - (4-dodecylphenyl) butane tetracarboxylic 1,2-imide 3,4 - anhydride- (17) N - (4 - dodecylphenyl) pyromellitic di - imidoacetic acid and its acid chloride- (22) 1 - hydroxy - 4 - chloro-2 - N - (3 - nitro - and 3 - aminobenzyl) naphthamides. Specifications 547,064, 599,919, 680,474, 680,488, 754,306, 757,368, 791,219, 797,141, 830,797, 865,720, 890,305, 902,266 and 956,261 are referred to.
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL133047D NL133047C (en) | 1963-06-17 | ||
| GB24026/63A GB1004075A (en) | 1963-06-17 | 1963-06-17 | Improvements in or relating to colour couplers and to their production and use in colour photography |
| US375380A US3312715A (en) | 1963-06-17 | 1964-06-15 | Colour couplers and their production and use in colour photography |
| DE19641520157 DE1520157A1 (en) | 1963-06-17 | 1964-06-16 | Process for the manufacture of color couplers |
| CH783264A CH446058A (en) | 1963-06-17 | 1964-06-16 | Use of compounds as color couplers |
| BE649350A BE649350A (en) | 1963-06-17 | 1964-06-16 | |
| FR978562A FR1399079A (en) | 1963-06-17 | 1964-06-17 | Improvements to color trainers, known as chromogenic generators or couplers, to their production and use in color photography |
| NL6406891A NL6406891A (en) | 1963-06-17 | 1964-06-17 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB24026/63A GB1004075A (en) | 1963-06-17 | 1963-06-17 | Improvements in or relating to colour couplers and to their production and use in colour photography |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1004075A true GB1004075A (en) | 1965-09-08 |
Family
ID=10205202
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB24026/63A Expired GB1004075A (en) | 1963-06-17 | 1963-06-17 | Improvements in or relating to colour couplers and to their production and use in colour photography |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3312715A (en) |
| BE (1) | BE649350A (en) |
| CH (1) | CH446058A (en) |
| DE (1) | DE1520157A1 (en) |
| GB (1) | GB1004075A (en) |
| NL (2) | NL6406891A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4374220A (en) | 1968-09-18 | 1983-02-15 | Raychem Corporation | Imide flame retardants and compositions containing them |
| US4535170A (en) * | 1968-09-18 | 1985-08-13 | Raychem Corporation | Flame retardants and compositions containing them |
| US4581396A (en) * | 1968-09-18 | 1986-04-08 | Raychem Corporation | Flame retardants and compositions containing them |
| US4644066A (en) * | 1968-09-18 | 1987-02-17 | Raychem Corporation | Flame retardants and compositions containing them |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3483217A (en) * | 1966-12-02 | 1969-12-09 | Allied Chem | 9,10-dihydro-9,10-dioxoanthracenediyl- bis-(4'-carbamoylphthalimides |
| DE1905864C3 (en) * | 1968-02-07 | 1974-11-21 | Konishiroku Photo Industry Co. Ltd., Tokio | Silver halide color photographic emulsion |
| US3927027A (en) * | 1973-10-31 | 1975-12-16 | Trw Inc | Bis(furfuryl) imide |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2905694A (en) * | 1959-09-22 | Certain esters of i | ||
| US2710803A (en) * | 1953-03-26 | 1955-06-14 | Eastman Kodak Co | Color couplers containing hydroxyalkyl groups |
| US2837557A (en) * | 1953-04-22 | 1958-06-03 | Union Carbide Corp | Esters of n, nu-bis(2-cyanoethyl) carboxamic acids |
| US2933391A (en) * | 1956-09-06 | 1960-04-19 | Eastman Kodak Co | Photographic emulsions containing 5-pyrazolone coupler compounds |
| US2878263A (en) * | 1958-02-14 | 1959-03-17 | Ortho Pharma Corp | 4-methyl-4-phenyl-5-pyrazolone |
| US3014033A (en) * | 1958-03-26 | 1961-12-19 | Glaxo Lab Ltd | Derivatives of tetraiodophthalamic acid |
| US2983608A (en) * | 1958-10-06 | 1961-05-09 | Eastman Kodak Co | Yellow-colored magenta-forming couplers |
| US3148178A (en) * | 1962-11-07 | 1964-09-08 | Eastman Kodak Co | Azo compounds containing a dicarboximido radical |
-
0
- NL NL133047D patent/NL133047C/xx active
-
1963
- 1963-06-17 GB GB24026/63A patent/GB1004075A/en not_active Expired
-
1964
- 1964-06-15 US US375380A patent/US3312715A/en not_active Expired - Lifetime
- 1964-06-16 DE DE19641520157 patent/DE1520157A1/en active Pending
- 1964-06-16 CH CH783264A patent/CH446058A/en unknown
- 1964-06-16 BE BE649350A patent/BE649350A/xx unknown
- 1964-06-17 NL NL6406891A patent/NL6406891A/xx unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4374220A (en) | 1968-09-18 | 1983-02-15 | Raychem Corporation | Imide flame retardants and compositions containing them |
| US4535170A (en) * | 1968-09-18 | 1985-08-13 | Raychem Corporation | Flame retardants and compositions containing them |
| US4581396A (en) * | 1968-09-18 | 1986-04-08 | Raychem Corporation | Flame retardants and compositions containing them |
| US4644066A (en) * | 1968-09-18 | 1987-02-17 | Raychem Corporation | Flame retardants and compositions containing them |
Also Published As
| Publication number | Publication date |
|---|---|
| NL133047C (en) | |
| CH446058A (en) | 1967-10-31 |
| BE649350A (en) | 1964-10-16 |
| US3312715A (en) | 1967-04-04 |
| NL6406891A (en) | 1964-12-18 |
| DE1520157A1 (en) | 1969-11-13 |
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