US2437063A - Nondiffusing 1-phenyl-5-pyrazolone couplers for color photography - Google Patents
Nondiffusing 1-phenyl-5-pyrazolone couplers for color photography Download PDFInfo
- Publication number
- US2437063A US2437063A US431263A US43126342A US2437063A US 2437063 A US2437063 A US 2437063A US 431263 A US431263 A US 431263A US 43126342 A US43126342 A US 43126342A US 2437063 A US2437063 A US 2437063A
- Authority
- US
- United States
- Prior art keywords
- pyrazolone
- phenyl
- silver halide
- red
- color
- 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 - Lifetime
Links
- FTCOWMWIZNVSPP-UHFFFAOYSA-N 2-phenyl-4h-pyrazol-3-one Chemical compound O=C1CC=NN1C1=CC=CC=C1 FTCOWMWIZNVSPP-UHFFFAOYSA-N 0.000 title description 5
- 239000000839 emulsion Substances 0.000 description 21
- -1 silver halide Chemical class 0.000 description 21
- 229910052709 silver Inorganic materials 0.000 description 18
- 239000004332 silver Substances 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000975 dye Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000010410 layer Substances 0.000 description 11
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 10
- 238000010521 absorption reaction Methods 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 7
- 108010010803 Gelatin Proteins 0.000 description 6
- 229920000159 gelatin Polymers 0.000 description 6
- 239000008273 gelatin Substances 0.000 description 6
- 235000019322 gelatine Nutrition 0.000 description 6
- 235000011852 gelatine desserts Nutrition 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- BZORFPDSXLZWJF-UHFFFAOYSA-N N,N-dimethyl-1,4-phenylenediamine Chemical compound CN(C)C1=CC=C(N)C=C1 BZORFPDSXLZWJF-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 125000004104 aryloxy group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000009792 diffusion process Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- SKYBRLALUDNCSM-UHFFFAOYSA-N 1,1-dimethyl-2-phenylhydrazine Chemical compound CN(C)NC1=CC=CC=C1 SKYBRLALUDNCSM-UHFFFAOYSA-N 0.000 description 2
- FSJYPYANWQAMSH-UHFFFAOYSA-N 3-heptadecyl-1,4-dihydropyrazol-5-one Chemical compound C(CCCCCCCCCCCCCCCC)C1=NNC(C1)=O FSJYPYANWQAMSH-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 235000019646 color tone Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- AWFYPPSBLUWMFQ-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=C2 AWFYPPSBLUWMFQ-UHFFFAOYSA-N 0.000 description 1
- ILPGQKHPPSSCBS-UHFFFAOYSA-N 2-phenyl-1h-pyrazol-3-one Chemical compound O=C1C=CNN1C1=CC=CC=C1 ILPGQKHPPSSCBS-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- ALLNAVCIMOJNMN-UHFFFAOYSA-N 4-phenylpyrazol-3-one Chemical class O=C1N=NC=C1C1=CC=CC=C1 ALLNAVCIMOJNMN-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 229910000906 Bronze Inorganic materials 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- UOBCZXSWQQWTGC-UHFFFAOYSA-N amino(phenyl)carbamic acid Chemical compound OC(=O)N(N)C1=CC=CC=C1 UOBCZXSWQQWTGC-UHFFFAOYSA-N 0.000 description 1
- WNNBGLYZPXMVJG-UHFFFAOYSA-N amino(phenyl)sulfamic acid Chemical class OS(=O)(=O)N(N)C1=CC=CC=C1 WNNBGLYZPXMVJG-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000010974 bronze Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical compound ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 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
Definitions
- Our present invention relates to the production of color photographic images and more particularly to an improved photographic silver halide emulsion containing a dyestuff former.
- the phenylpyrazolones of the present invention contain in the 3-position ofthe pyrazolone nucleus radicals preventing diffusion, for instance, carbon chains with at least 6 carbon atoms color fogging. :Furthermore, this dyestuif comfication following hereinafter.
- the silver halide emulsion prepared by means of the dyestufi components of the present invention may be cast to form single layers or worked up int'o'a multi-layer material containing further emulsion layers with dyestuff formers for the other component-colorsand, if necessary, filter layers, intermediate layers and anti-halation layers
- the emulsion layers may contain corresponding sensitizers and be arranged on one or both sides of the support.
- the multi-layer material may also comprise emulsion layers capable of producing dyestuffs according to a color photographic'method' rather than that mentioned above, The color images may be obtained by a Useful substituents are alkyl, alkoxy, alkthio,
- the pyrazolones are prepared by reacting phenylhydrazinesulfonic acids or phenylhydrazine carboxylic'acids correspondingly substituted with high-molecular weight acylacetic acid esters.
- the pyrazolones simple development'or a reversal development as negatives or positives respectively.
- Example l 10 g. of 1-(4'-methylphenyl-3'-sulfonic acid) 3-heptadecyl) -5-pyrazolone are neutralized with a diluted sodium hydroxide solution with. warming.
- the resulting solution of the sodium salt is substituted according to the invention are dismadeup to 200 cc. with water, then added to 1 kilo of a silver halide gelatin emulsion and finally cast. After exposure a non-bronzing slightly bluishred dyestuff image having an absorption maximum at about 530 m is produced by treating with a developer of the following composition:
- Example 2 10 g. of the sodium salt of 1-(4'-brompheny1- 3-sulfonic acid) -3-heptadecyl-5-pyrazolone are dissolved in 200 cc. of water with gentle heating and added to 1 kilo of a silver halide gelatin emulsion layer before casting. On color forming development with a developer containing p-dimethylaminoaniline one obtains a non-bronzing, clear 7 and slightly bluish red dyestufi image. This dyestuif shows a maximum absorption of about 530 m
- Example 3 Example 4 10 g.
- Example 7 10 g. of 1-(4-phenoxyphenyl-3-sulfonic acid) 3-heptadecyl-5-pyrazolone are neutralized with 30 cc. of a n/10 sodium hydroxide solution, dissolved with gentle heating, made up to 200 cc. and added to one kilo of a molten silver halide gelatin emulsion before casting.
- the exposed emulsion layer yields a blue-red dyestufi image having an absorption maximum of about 530 m on color forming development with a developer containing dimethylaminoaniline.
- Example 8 If instead of the dyestuff former mentioned in Example '7 1-(4-phenoxyphenyl-3-sulfonic acid) 3 heptadecenyl 5 pyrazolone is used, a blue-red dyestuff image having a maximum absorption of 530 m is produced.
- Example 9 10 g. of 1-(3-chloro-4'-methylphenyl-5'-sulionic acid) -3-heptadecyl-5-pyrazolone is neutralized with a diluted sodium hydroxide solution.
- the clear solution obtained by heating is made up to 200 cc. with water, added to 1 kilo of a molten silver halide gelatin emulsion and cast.
- a blue-red very transparent dyestuff image having an absorption maximum of about 535 m is obtained by the treatment with a developer containing dimethylaminoaniline.
- sodium salts of the pyrazolones of the invention other soluble salts may also be used,.especially alkali metal salts.
- a silver halide emulsion for color forming development containing as the dyestuff former for red a soluble salt of 1-phenyl-5-pyrazolone containing in the 3-position of the pyrazolone nucleus a radical producing fastness to difiusion and in the phenyl nucleus at least one group increasing the solubility in Water and in the positions of said phenyl nucleus selected from the group consisting of the 3-, 4- and 5- positions at least one substituent selected from the class consisting of alkyl, alkoxy, alkthio, alkseleno, aryloxy and halogens.
- a silver halide emulsion for color forming development containing as the dyestuff former for red a soluble salt of 1-phenyl-5-pyrazolone containing in the 3 position of the pyrazolone nucleus a carbon chain having at least 6 carbon atoms and in the phenyl nucleus at least one group increasing the solubility in water and in the positions of said phenylnucleus selected from the group consisting of the 3-, 4- and 5-positions at least one substituent selected from the class consisting of alkyl, alkoxy, alkthio, alkseleno, a-ryloxy and halogens.
- a silver halide emulsion for color forming development containing asthe dyestuff former for red a Water-soluble salt of 1-(4-methylphenyl-3'-sulf0nic acid) -3-heptadecyl-5-pyrazolone.
- a silver halide emulsion for color forming development containing as the dyestuff former for red a soluble salt of 1-( l-chlorphenyl3'-carboxylic acid) -3-heptadecyl-5-pyrazolone.
- a silver halide emulsion for color forming development containing as the dyestuif former for red a soluble salt of a 1-phenyl-5-pyrazolone containing in the 3-position of the pyrazolone nucleus a radical imparting iastness to diffusion in the binding agent of the silver halide emulsion and containing in the phenyl nucleus a group increasing the solubility of the compound in Water and in only one of the positions of said phenyl nucleus selected from the group consisting of the 3-, 4- and 5-positions a substituent selected from the class consisting of alkyl, alkoxy, alkthio, alkseleno, aryloxy and halogen.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Silver Salt Photography Or Processing Solution Therefor (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI0067601 | 1940-08-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2437063A true US2437063A (en) | 1948-03-02 |
Family
ID=7196749
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US431263A Expired - Lifetime US2437063A (en) | 1940-08-08 | 1942-02-17 | Nondiffusing 1-phenyl-5-pyrazolone couplers for color photography |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US2437063A (en(2012)) |
| BE (1) | BE442410A (en(2012)) |
| CH (2) | CH239482A (en(2012)) |
| FR (1) | FR876814A (en(2012)) |
| NL (1) | NL59371C (en(2012)) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2933391A (en) * | 1956-09-06 | 1960-04-19 | Eastman Kodak Co | Photographic emulsions containing 5-pyrazolone coupler compounds |
| US3443954A (en) * | 1964-05-23 | 1969-05-13 | Agfa Ag | Silver halide photographic material containing 3 - acylamino-pyrazolone couplers |
| US3519429A (en) * | 1966-05-16 | 1970-07-07 | Eastman Kodak Co | Silver halide emulsions containing a stabilizer pyrazolone coupler |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR836144A (fr) * | 1935-03-21 | 1939-01-11 | Kodak Pathe | Perfectionnements aux procédés de photographie en couleurs et en particulier aux révélateurs chromogènes |
| US2179239A (en) * | 1935-04-10 | 1939-11-07 | Agfa Ansco Corp | Color photography |
| US2186849A (en) * | 1935-08-07 | 1940-01-09 | Agfa Ansco Corp | Manufacture of photographic silver halide emulsions |
| US2200306A (en) * | 1937-07-23 | 1940-05-14 | Gen Aniline & Film Corp | Compound having reactive methylene groups |
| US2213986A (en) * | 1938-04-08 | 1940-09-10 | Ilford Ltd | Production of colored photographic images |
-
0
- NL NL59371D patent/NL59371C/xx active
- BE BE442410D patent/BE442410A/xx unknown
-
1941
- 1941-08-07 FR FR876814D patent/FR876814A/fr not_active Expired
- 1941-09-04 CH CH239482D patent/CH239482A/de unknown
- 1941-09-04 CH CH234804D patent/CH234804A/de unknown
-
1942
- 1942-02-17 US US431263A patent/US2437063A/en not_active Expired - Lifetime
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR836144A (fr) * | 1935-03-21 | 1939-01-11 | Kodak Pathe | Perfectionnements aux procédés de photographie en couleurs et en particulier aux révélateurs chromogènes |
| US2179239A (en) * | 1935-04-10 | 1939-11-07 | Agfa Ansco Corp | Color photography |
| US2186849A (en) * | 1935-08-07 | 1940-01-09 | Agfa Ansco Corp | Manufacture of photographic silver halide emulsions |
| US2200306A (en) * | 1937-07-23 | 1940-05-14 | Gen Aniline & Film Corp | Compound having reactive methylene groups |
| US2213986A (en) * | 1938-04-08 | 1940-09-10 | Ilford Ltd | Production of colored photographic images |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2933391A (en) * | 1956-09-06 | 1960-04-19 | Eastman Kodak Co | Photographic emulsions containing 5-pyrazolone coupler compounds |
| US3443954A (en) * | 1964-05-23 | 1969-05-13 | Agfa Ag | Silver halide photographic material containing 3 - acylamino-pyrazolone couplers |
| US3519429A (en) * | 1966-05-16 | 1970-07-07 | Eastman Kodak Co | Silver halide emulsions containing a stabilizer pyrazolone coupler |
Also Published As
| Publication number | Publication date |
|---|---|
| CH239482A (de) | 1945-10-15 |
| NL59371C (en(2012)) | |
| FR876814A (fr) | 1942-11-18 |
| CH234804A (de) | 1944-10-31 |
| BE442410A (en(2012)) |
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