US2214483A - Photographic color picture - Google Patents
Photographic color picture Download PDFInfo
- Publication number
- US2214483A US2214483A US265758A US26575839A US2214483A US 2214483 A US2214483 A US 2214483A US 265758 A US265758 A US 265758A US 26575839 A US26575839 A US 26575839A US 2214483 A US2214483 A US 2214483A
- Authority
- US
- United States
- Prior art keywords
- acid
- emulsion
- layer
- color
- development
- 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
- 239000000839 emulsion Substances 0.000 description 28
- 239000010410 layer Substances 0.000 description 25
- 229910052709 silver Inorganic materials 0.000 description 18
- 239000004332 silver Substances 0.000 description 18
- -1 silver halide Chemical class 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 229910052799 carbon Inorganic materials 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 238000009792 diffusion process Methods 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- JGVXXBLZLMUBPB-NSCUHMNNSA-N (2e)-2-ethylidene-3-oxobutanedioic acid Chemical compound C\C=C(\C(O)=O)C(=O)C(O)=O JGVXXBLZLMUBPB-NSCUHMNNSA-N 0.000 description 1
- 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 description 1
- GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 229940051880 analgesics and antipyretics pyrazolones Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 229940093858 ethyl acetoacetate Drugs 0.000 description 1
- BTNMPGBKDVTSJY-UHFFFAOYSA-N keto-phenylpyruvic acid Chemical compound OC(=O)C(=O)CC1=CC=CC=C1 BTNMPGBKDVTSJY-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- WTBAHSZERDXKKZ-UHFFFAOYSA-N octadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCCCC(Cl)=O WTBAHSZERDXKKZ-UHFFFAOYSA-N 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 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
Definitions
- photographicv color pictures can-be produced with the aid of color developmentby introducinginto the developer or into the photographic layer a color former which condenses with certain developer substances-to produce a color on thesilver image.
- dyestuff formers for color development-there have been proposed among others aliphatic and aromatic acid methylene compounds, for example ethylacetoacetate and its derivatives, ethylbenzoylacetate, pyrazolones or the like.
- This one object'of ourinvention to provide a processof the kind in'question in which there are used for color development pyroracemic acids and derivatives of pyroracemic acids in which the .methyl group contains as a. substituent a radicle of aliphatic, isocyclicor heterocyclic nature, having double linking adjacent to said methyl group.
- Vinylene groups may be substituted,
- R1-'CI-I2-CO R2 infl which R1 is a radicle. of acyclic, .isocyclic or heterocyclic nature which has one or more double linkings adjacent to the CI-Iz-group and may contain-substituents, for instance methyl, carboxyl or the like, and R2 is carboxyl, a substituted carboxyl, ON or the like.
- oxalocrotonic acid diethyl ester oxalosorbic 891d diethyl ester
- quinolyl-pyroracemic acid The color formers may be. added either to the photographic developer or to the emulsion.. With color develop-. ers, for example pararivative thereof yellow, orange or red dyestufi images are obtained. incorporated in the photographic layer it is, to
- the foregoing y means of the usual chemical may be made fast polymerization as described inthe
- the silver halide emulsion containing color formers fast to diffusion may be' used in known manner single layer or sion layers may for making photographic multilayer material.
- the emul also be made by distributing dif-' ferently sensitized emulsions having different color formers in the support.
- the aid of silver inaccordance be removed or black and wh'te pictures with halide emulsion layers produced with the invention the silver may be left' in the layer with the dyestuff image.
- Example 2. -To 1 kilo of a silver halide emulsion there are formula added 5 grams of the sodium salt ester of the exposed layer yields on development with paradimethylaminoaniline a yellow dyestufi image.
- Example 3. -To 1 kilo of a silver halide emulsion there are added 5 grams the oxalosorbic acid of the sodium salt of diethyl ester of the formula cH-wm-omcoocnin and the emulsion is cast to form a layer.
- Example 4 To 1 kilo of a silver halide emulsion 5 grams of oxalomethylcrotonic acid ethyl 5 ester are added and the emulsion is cast to form a layer. The exposed layer yields on development with .para-diethylaminoaniline' a reddish yellow dyestufi image.
- Example 5 To 1 kilo of a silver halide emulan orange-red dyestufi of ortho-nitrophenyl-pyroracemic acid. and the. emulsion is cast to form a layer;
- Example 1.0.4-aminophenyl-pyroracemic acid is.caused; toreact in pyridine with stearic acid chloride fand the 4 stearoylarninophenyl-racemic acid thus obtained is precipitated. by meansv of' dilute acid. 5 grams of. this. product are added to 1. kilo. of. a silver halide emulsion .and the emulsion-is cast. to form aflayer. Tliefexposed' layer yields on development with para-diethylaminoaniline a yellow dyestuif image.
- Example 11-.+4.eaminophenyl-racemic acid is caused to react in pyridine withll l' diphenyl- 5Q; dicarboxylic. acid chloride and the product is. pre-' cipitated;.. 51 grams. of the product obtained are added to lkilo of'a silver halide emulsionand the emulsion is cast to form a layer. The exposed emulsion yields on development with para-diethylaminoaniline a. yellow dyestufi image.
- Example 12.-To 1. kilo of aisilver halide emule sionthere. are added. 5 grams of quinoxalyl-Z- pyroracemic acid ethyl ester corresponding with the formula I CCH2.C 0.0 O 0 CZHE m ing with the formula sion there are added 5 grams of the sodium salt:
- the exposedlayer yields on development. with para-diethyl--
- the exposed and the emulsion is cast to form a layer.
- the exposed layer yields on development with para-diethylaminoaniline an orange dyestufi image.
- Example 14 To 1 kilo of a silver halide emulsion there are added 5 grams of benzoxazole-2- pyroracemic acid corresponding with the formula CCH2.C 0.0 OOH N andthe emulsion is cast to form a layer. The exposed-layer yields.) on development with para-diethylaminoanilinaan. orange dyestufi image.
- R1 is a radicle selected from the classconsisting ofran'yaliphatic radiclej. an; i'socyclio radicle and aheterocyclic. radicle, saidradicla having an unsaturated double bond adjacent'itos said CI-Iz-group
- R2 isaradicle selected from the class consisting of carboxyl; substituted carboxyl, and UN; .to .reaouwith the oxidation-productof anc aromatic developer.
- the improvement whichcomprises exposing a photographic silver halide emulsion containing asthe dyestuifi-former a derivative of the pyjacent to the carbon atom of said methyl group,
- said derivative containing a radicle imparting thereto fastness to diffusion with respect to the binding agent of said emulsion, and developing said emulsion with an aromatic amino developer.
- Silver halide emulsion for color photography comprising a derivative of the p-yroracemic acid, at least the methyl group of said acid being substituted by an organic radicle having an unsaturated double bond in a position adjacent to the carbon atom of said methyl group, said derivative containing a radicle imparting thereto fastness to diffusion with respect to the binding agent of said emulsion.
- a dyestuif forming developer comprising an aqueous solution containing an aromatic amino developing agent and a derivative of the p yroracemic acid, at least the methyl group: of said acid being substituted by an organic radicle having an unsaturated double bond in a position 1 adjacent to the carbon atom of said methyl group.
- a silver halide emulsion for color photography containing as a color-forming development component a derivative of pyroracemic acid of the following general formula wherein R1 is an organic radicle, having an unsaturated double bond in a position adjacent to the WILI'IELM SCHNEIDER.
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEI0061048 | 1938-04-09 |
Publications (1)
Publication Number | Publication Date |
---|---|
US2214483A true US2214483A (en) | 1940-09-10 |
Family
ID=7195385
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US265758A Expired - Lifetime US2214483A (en) | 1938-04-09 | 1939-04-03 | Photographic color picture |
Country Status (3)
Country | Link |
---|---|
US (1) | US2214483A (fr) |
BE (1) | BE433702A (fr) |
FR (1) | FR852803A (fr) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2435173A (en) * | 1944-06-07 | 1948-01-27 | Gen Aniline & Film Corp | Acetyl n-heterocyclic couplers for color photography |
US5066576A (en) * | 1989-10-03 | 1991-11-19 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8545539B2 (en) | 2008-05-12 | 2013-10-01 | Edwin E. Spencer | Proximal humeral fracture reduction and fixation device |
-
0
- BE BE433702D patent/BE433702A/xx unknown
-
1939
- 1939-04-03 US US265758A patent/US2214483A/en not_active Expired - Lifetime
- 1939-04-07 FR FR852803D patent/FR852803A/fr not_active Expired
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2435173A (en) * | 1944-06-07 | 1948-01-27 | Gen Aniline & Film Corp | Acetyl n-heterocyclic couplers for color photography |
US5066576A (en) * | 1989-10-03 | 1991-11-19 | Fuji Photo Film Co., Ltd. | Silver halide color photographic material |
Also Published As
Publication number | Publication date |
---|---|
BE433702A (fr) | |
FR852803A (fr) | 1940-03-04 |
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