GB558855A - Improvements in colour forming developers, processes of colour development and photographic emulsions for forming coloured images - Google Patents
Improvements in colour forming developers, processes of colour development and photographic emulsions for forming coloured imagesInfo
- Publication number
- GB558855A GB558855A GB8511/42A GB851142A GB558855A GB 558855 A GB558855 A GB 558855A GB 8511/42 A GB8511/42 A GB 8511/42A GB 851142 A GB851142 A GB 851142A GB 558855 A GB558855 A GB 558855A
- Authority
- GB
- United Kingdom
- Prior art keywords
- pyrazolone
- anilino
- acetyl
- bromanilino
- group
- 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
- 239000000839 emulsion Substances 0.000 title 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 abstract 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 abstract 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 abstract 1
- PAEBEUZTAPIOIO-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-(1-methyl-3-oxo-2-phenyl-5-propan-2-ylpyrazol-4-yl)urea Chemical compound O=C1N(C=2C=CC=CC=2)N(C)C(C(C)C)=C1NC(=O)NC1=CC=C(Cl)C=C1 PAEBEUZTAPIOIO-UHFFFAOYSA-N 0.000 abstract 1
- WNFPNYJXZDMKQI-UHFFFAOYSA-N 1-isothiocyanato-4-(2-methylbutan-2-yl)benzene Chemical compound C(C)(C)(CC)C1=CC=C(C=C1)N=C=S WNFPNYJXZDMKQI-UHFFFAOYSA-N 0.000 abstract 1
- OMMTWGSEEFLNOQ-UHFFFAOYSA-N 2-acetyl-5-(2-bromophenyl)iminopyrazolidin-3-one Chemical compound C(C)(=O)N1N=C(CC1=O)NC1=C(C=CC=C1)Br OMMTWGSEEFLNOQ-UHFFFAOYSA-N 0.000 abstract 1
- UBXMFRNVKJYYIJ-UHFFFAOYSA-N 2-acetyl-5-(4-iodophenyl)iminopyrazolidin-3-one Chemical compound C(C)(=O)N1N=C(CC1=O)NC1=CC=C(C=C1)I UBXMFRNVKJYYIJ-UHFFFAOYSA-N 0.000 abstract 1
- WAZMKWZANLPIQM-UHFFFAOYSA-N 2-acetyl-5-phenyliminopyrazolidin-3-one Chemical compound C(C)(=O)N1N=C(CC1=O)NC1=CC=CC=C1 WAZMKWZANLPIQM-UHFFFAOYSA-N 0.000 abstract 1
- ACWHNIQGRPMZMQ-UHFFFAOYSA-N 2-benzoyl-5-phenyliminopyrazolidin-3-one Chemical compound C(C1=CC=CC=C1)(=O)N1N=C(CC1=O)NC1=CC=CC=C1 ACWHNIQGRPMZMQ-UHFFFAOYSA-N 0.000 abstract 1
- NVNQBSAGKYGGQW-UHFFFAOYSA-N 2-methyl-5-phenyliminopyrazolidin-3-one Chemical compound CN1N=C(CC1=O)NC1=CC=CC=C1 NVNQBSAGKYGGQW-UHFFFAOYSA-N 0.000 abstract 1
- XISQSPCFZGPMNT-UHFFFAOYSA-N 3-(4-methoxyanilino)-1,4-dihydropyrazol-5-one Chemical compound C1=CC(OC)=CC=C1NC1=NNC(=O)C1 XISQSPCFZGPMNT-UHFFFAOYSA-N 0.000 abstract 1
- RQUPXQYTWVIBIV-UHFFFAOYSA-N 4-(2-methylbutan-2-yl)aniline Chemical compound CCC(C)(C)C1=CC=C(N)C=C1 RQUPXQYTWVIBIV-UHFFFAOYSA-N 0.000 abstract 1
- XIAYEIOGEIZBJB-UHFFFAOYSA-N 4-[(1-acetyl-5-oxopyrazolidin-3-ylidene)amino]benzonitrile Chemical compound C(C)(=O)N1N=C(CC1=O)NC1=CC=C(C=C1)C#N XIAYEIOGEIZBJB-UHFFFAOYSA-N 0.000 abstract 1
- JBDRZHYDWGFPPH-UHFFFAOYSA-N 5-(2-bromophenyl)iminopyrazolidin-3-one Chemical compound BrC1=C(NC2=NNC(C2)=O)C=CC=C1 JBDRZHYDWGFPPH-UHFFFAOYSA-N 0.000 abstract 1
- UPHYIGXENVCUDS-UHFFFAOYSA-N 5-(4-bromophenyl)iminopyrazolidin-3-one Chemical compound Brc1ccc(NC2=NNC(=O)C2)cc1 UPHYIGXENVCUDS-UHFFFAOYSA-N 0.000 abstract 1
- WVTYBIRPWOKATG-UHFFFAOYSA-N 5-(4-iodophenyl)iminopyrazolidin-3-one Chemical compound IC1=CC=C(NC2=NNC(C2)=O)C=C1 WVTYBIRPWOKATG-UHFFFAOYSA-N 0.000 abstract 1
- NOZWDPICYADQLV-UHFFFAOYSA-N 5-anilinopyrazol-3-one Chemical compound N1=NC(=O)C=C1NC1=CC=CC=C1 NOZWDPICYADQLV-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- 101710178035 Chorismate synthase 2 Proteins 0.000 abstract 1
- 101710152694 Cysteine synthase 2 Proteins 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- WCXXMDGUNOKGGE-UHFFFAOYSA-N N-[4-[(5-oxopyrazolidin-3-ylidene)amino]phenyl]acetamide Chemical compound N(C(=O)C)C1=CC=C(NC2=NNC(C2)=O)C=C1 WCXXMDGUNOKGGE-UHFFFAOYSA-N 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- -1 alkyl hydrazine Chemical compound 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 abstract 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 150000002540 isothiocyanates Chemical class 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 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
- G03C7/38—Couplers containing compounds with active methylene groups in rings
- G03C7/384—Couplers containing compounds with active methylene groups in rings in pyrazolone rings
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Pyridine Compounds (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
558,855. Pyrazolones and their intermediates. KODAK, Ltd. June 22, 1942, No. 8511. Convention date, Nov. 14, 1941, [Class 2 (iii)] [Also in Group XX] Pyrazolones having the general formula wherein R represents an alkyl or aryl group, and R<SP>1</SP> a hydrogen atom or an alkyl group, are prepared by condensing an isothiocyanate with ethyl acetoacetate and reacting the product with hydrazine hydrate or an alkyl hydrazine. Those products wherein R<SP>1</SP> is hydrogen may be acylated, e.g. by means of an organic anhydride or chloride in the presence of a condensing agent such as pyridine. Examples specified are 3 - anilino - 5 pyrazolone, 1 - acetyl - 3 - anilino - 5 - pyrazolone, 3 - α - naphthylamino - 5 - 'pyrazolone, 1 - acetyl - 3 - α - naphthylamino - 5 - pyrazolone, 3 - p - acetaminoanilino - 5 - pyrazolone, 3 - o - bromanilino - 5 - pyrazolone, 1 - acetyl - 3 - o - bromanilino - 5 - pyrazolone, 3 - p - - bromanilino - 5 - pyrazolone, 1 - acetyl - 3 - p - bromanilino - 5 - pyrozolone, 3 - p - methoxyanilino - 5 - pyrazolone, 3 - p - cyanolino - 5 - pyrazolcne, 1 - acetyl - 3 - p - cyanoanilino - 5 - pyrazolone, 3 - p nitranilino - 5 - pyrazolone, 3 - n - amylamino - 5 - pyrazolone, 3 - p - iodoanilino - 5 - pyrazolone, 1 - acetyl - 3 - p - iodoanilino - 5 - pyrazolone, 1 - n - valeryl - 3 - anilino 5 - pyrazolone, 3 - p - tert. - amylanilino - 5 - pyrazalone, 3 - p - dimethylaminoanilino - 5 - pyrazolone, 1 - benzoyl - 3 - anilino - 5 - pyrazolone, 1 - phenoxyacet - 3 - anilino - 5 - pyrazolone, 1 - methoxyacet - 3 - anilino - 5 - pyrazolone, and 1 - methyl - 3 - anilino - 5 - pyrazolone. The compounds are used as colour couplers, (see Group XX), Specifications 427,472, 427,516, 427,518, 427,520, 440,032, 440,089, 447,092, 507,841, 524,154, 524,554, 524,555, 540,366, 540,368, and 541,589, [all in Group XX], are referred to. p - tert - amylphenyl isothiocyanate is prepared by reacting p - tert - amylaniline saturated with NH 3 , with CS 2 , removing excess NH 3 , and reacting with phosgene.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US419172A US2311081A (en) | 1941-11-14 | 1941-11-14 | Iminopyrazolone coupler for color photography |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB558855A true GB558855A (en) | 1944-01-25 |
Family
ID=23661096
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8511/42A Expired GB558855A (en) | 1941-11-14 | 1942-06-22 | Improvements in colour forming developers, processes of colour development and photographic emulsions for forming coloured images |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US2311081A (en) |
| FR (1) | FR965998A (en) |
| GB (1) | GB558855A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2672417A (en) * | 1949-12-31 | 1954-03-16 | Gevaert Photo Prod Nv | Production of color photographic images |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2929511B2 (en) * | 1991-09-25 | 1999-08-03 | コニカ株式会社 | Silver halide color photographic materials |
| JPH0588324A (en) * | 1991-09-25 | 1993-04-09 | Konica Corp | Silver halide color photographic sensitive material |
| JP3443504B2 (en) | 1995-12-27 | 2003-09-02 | コニカ株式会社 | Silver halide color photographic materials |
-
1941
- 1941-11-14 US US419172A patent/US2311081A/en not_active Expired - Lifetime
-
1942
- 1942-06-22 GB GB8511/42A patent/GB558855A/en not_active Expired
-
1947
- 1947-08-01 FR FR965998D patent/FR965998A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2672417A (en) * | 1949-12-31 | 1954-03-16 | Gevaert Photo Prod Nv | Production of color photographic images |
Also Published As
| Publication number | Publication date |
|---|---|
| FR965998A (en) | 1950-09-27 |
| US2311081A (en) | 1943-02-16 |
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