GB1044959A - Method and material for producing photographic colour images - Google Patents
Method and material for producing photographic colour imagesInfo
- Publication number
- GB1044959A GB1044959A GB39999/63A GB3999963A GB1044959A GB 1044959 A GB1044959 A GB 1044959A GB 39999/63 A GB39999/63 A GB 39999/63A GB 3999963 A GB3999963 A GB 3999963A GB 1044959 A GB1044959 A GB 1044959A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- methyl
- hexadecylsulphonyl
- hexadecylsulphamoyl
- hexadecylthio
- 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
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 abstract 1
- ZQWSSTSVUYICSB-UHFFFAOYSA-N (2-chloro-4-hexadecylsulfonylphenyl)hydrazine Chemical compound CCCCCCCCCCCCCCCCS(=O)(=O)C1=CC=C(NN)C(Cl)=C1 ZQWSSTSVUYICSB-UHFFFAOYSA-N 0.000 abstract 1
- WVIOEMHKCQHJDP-UHFFFAOYSA-N (2-hexadecylsulfonylphenyl)hydrazine Chemical compound C(CCCCCCCCCCCCCCC)S(=O)(=O)C1=C(C=CC=C1)NN WVIOEMHKCQHJDP-UHFFFAOYSA-N 0.000 abstract 1
- QMPJOPDJJBTIOM-UHFFFAOYSA-N (5-chloro-2-hexadecylsulfanylphenyl)hydrazine Chemical compound C(CCCCCCCCCCCCCCC)SC1=C(C=C(C=C1)Cl)NN QMPJOPDJJBTIOM-UHFFFAOYSA-N 0.000 abstract 1
- HNTGIJLWHDPAFN-UHFFFAOYSA-N 1-bromohexadecane Chemical compound CCCCCCCCCCCCCCCCBr HNTGIJLWHDPAFN-UHFFFAOYSA-N 0.000 abstract 1
- NGIRMPARLVGMPX-UHFFFAOYSA-N 2-amino-4-chlorobenzenethiol Chemical compound NC1=CC(Cl)=CC=C1S NGIRMPARLVGMPX-UHFFFAOYSA-N 0.000 abstract 1
- BXLMGGAHOPLULA-UHFFFAOYSA-N 4-(3-amino-5-oxo-4H-pyrazol-1-yl)-N-hexadecyl-N-methylbenzenesulfonamide Chemical compound CCCCCCCCCCCCCCCCN(C)S(=O)(=O)C1=CC=C(C=C1)N1N=C(N)CC1=O BXLMGGAHOPLULA-UHFFFAOYSA-N 0.000 abstract 1
- JCRHASYDGFLNJP-UHFFFAOYSA-N 4-bromo-n-hexadecyl-n-methylbenzenesulfonamide Chemical compound CCCCCCCCCCCCCCCCN(C)S(=O)(=O)C1=CC=C(Br)C=C1 JCRHASYDGFLNJP-UHFFFAOYSA-N 0.000 abstract 1
- GUOHTIXIZPTEBT-UHFFFAOYSA-N 5-amino-2-(2-chloro-4-hexadecylsulfonylphenyl)-4H-pyrazol-3-one Chemical compound ClC1=C(C=CC(=C1)S(=O)(=O)CCCCCCCCCCCCCCCC)N1N=C(CC1=O)N GUOHTIXIZPTEBT-UHFFFAOYSA-N 0.000 abstract 1
- IFKPFDLYLLDEBI-UHFFFAOYSA-N 5-amino-2-(5-chloro-2-hexadecylsulfanylphenyl)-4H-pyrazol-3-one Chemical compound C(CCCCCCCCCCCCCCC)SC1=C(C=C(C=C1)Cl)N1N=C(CC1=O)N IFKPFDLYLLDEBI-UHFFFAOYSA-N 0.000 abstract 1
- KGQITJUDNMFQLV-UHFFFAOYSA-N 5-amino-2-hexadecan-2-ylsulfonyl-4H-pyrazol-3-one Chemical compound CC(CCCCCCCCCCCCCC)S(=O)(=O)N1N=C(CC1=O)N KGQITJUDNMFQLV-UHFFFAOYSA-N 0.000 abstract 1
- WYAGIIOJESNXEN-UHFFFAOYSA-N Cl.C(CCCCCCCCCCCCCCC)SC1=C(N)C=C(C=C1)Cl.N(=O)OCCC(C)C Chemical compound Cl.C(CCCCCCCCCCCCCCC)SC1=C(N)C=C(C=C1)Cl.N(=O)OCCC(C)C WYAGIIOJESNXEN-UHFFFAOYSA-N 0.000 abstract 1
- 229910006069 SO3H Inorganic materials 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 abstract 1
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 125000006849 chlorophenylene group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000012954 diazonium Substances 0.000 abstract 1
- 150000001989 diazonium salts Chemical class 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- JGQIXXYPXISIQT-UHFFFAOYSA-N n-hexadecyl-4-hydrazinyl-n-methylbenzenesulfonamide Chemical compound CCCCCCCCCCCCCCCCN(C)S(=O)(=O)C1=CC=C(NN)C=C1 JGQIXXYPXISIQT-UHFFFAOYSA-N 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 abstract 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 235000011150 stannous chloride Nutrition 0.000 abstract 1
- 239000001119 stannous chloride Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- -1 substituted Chemical class 0.000 abstract 1
Classifications
-
- 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
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms
-
- 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
- G03C7/18—Processes for the correction of the colour image in subtractive colour photography
-
- 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
- G03C7/38—Couplers containing compounds with active methylene groups in rings
- G03C7/384—Couplers containing compounds with active methylene groups in rings in pyrazolone rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Coloring (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Abstract
The invention comprises pyrazolones of the general formula <FORM:1044959/C2/1> wherein A is -SO3H or a salt thereof, Z completes an aromatic nucleus such as a benzene ring which may carry further substituents such as methyl, chloro or bromo, Y is a bivalent aromatic radical such as phenylene or chlorophenylene, X is -O-, -S-, -SO2-, -SO2NH- or a substituted -SO2NH-group, the sulphur atoms of such -SO2NH- groups, being attached to Y, D is an acyclic aliphatic radical of 5-20 carbon atoms and n is 1 or 2. The compounds are made by the following reaction scheme:- <FORM:1044959/C2/2> 1 - (2 - n - Hexadecylthio - 5 - chlorphenyl) - 3 - amino - 2 - pyrazolin - 5 - one is made by reacting ethyl b -amino-b -ethoxyacrylate in the presence of sodium methylate with 2-n-hexadecylthio - 5 - chlorphenyl hydrazine obtained by reducing with stannous chloride a diazonium salt solution formed by diazotizing with isoamyl nitrite 2 - n - hexadecylthio - 5 - chloroaniline hydrochloride prepared by condensing n-hexadecyl bromide with 2-mercapto-5-chloro-aniline. 1 - [4 - (N - methyl - N - hexadecylsulphamoyl)phenyl] - 3 - amino - 2 - pyrazolin - 5 - one is made by condensing ethyl b -imino-b -ethoxy propionate with 4-(N-methyl-N-hexadecylsulphamoyl) -phenyl hydrazine obtained by refluxing 4-(N-methyl-N-hexadecylsulphamoyl)-bromobenzene with anhydrous hydrazine. 1 - (4 - Hexadecylsulphonyl - 2 - chlorophenyl)3 -amino-2pyrazolin-5-one is obtained analogously via 4-hexadecylsulphonyl-2-chlorophenylhydrazine. 1 - (2 - Hexadecylsulphonyl) - 3 - amino - 2pyrazolin-5-one is obtained analogously via 2-hexadecylsulphonylphenylhydrazine.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB39999/63A GB1044959A (en) | 1963-10-10 | 1963-10-10 | Method and material for producing photographic colour images |
| US402652A US3330660A (en) | 1963-10-10 | 1964-10-08 | Method and material for producing photographic color images |
| BE654111D BE654111A (en) | 1963-10-08 | 1964-10-08 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB39999/63A GB1044959A (en) | 1963-10-10 | 1963-10-10 | Method and material for producing photographic colour images |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1044959A true GB1044959A (en) | 1966-10-05 |
Family
ID=10412642
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB39999/63A Expired GB1044959A (en) | 1963-10-08 | 1963-10-10 | Method and material for producing photographic colour images |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US3330660A (en) |
| GB (1) | GB1044959A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4443536A (en) * | 1981-08-25 | 1984-04-17 | Eastman Kodak Company | Nondiffusible photographic couplers and photographic elements and processes employing same |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2353205A (en) * | 1939-03-31 | 1944-07-11 | Eastman Kodak Co | Color-forming compound containing sulphonamide groups |
| US2369489A (en) * | 1941-09-25 | 1945-02-13 | Eastman Kodak Co | Acylated amino pyrazolone couplers |
| NL263254A (en) * | 1959-11-13 |
-
1963
- 1963-10-10 GB GB39999/63A patent/GB1044959A/en not_active Expired
-
1964
- 1964-10-08 US US402652A patent/US3330660A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4443536A (en) * | 1981-08-25 | 1984-04-17 | Eastman Kodak Company | Nondiffusible photographic couplers and photographic elements and processes employing same |
Also Published As
| Publication number | Publication date |
|---|---|
| US3330660A (en) | 1967-07-11 |
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