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
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- 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)
Description
Patented Sept. 10, 1940 Wilhelm Schneider and Germany, assignors,
General Aniline & Film Corporation,-
N. Y., a corporation of Delaware No Drawing. Application April 3, 1939, Serial No. 265,758. In GermanyApril 9, 1938 8Claims. (0195-6) Our present invention relates to the manufacture of photographic color pictures.
It is known that 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. As 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. 1 A
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,
further object of this invention is the provision of compounds having the following general formula 1.
. R1-'CI-I2-CO R2 inflwhich 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.
Other objects vof our invention, will become apparent from the following detailed description. For example the following compounds may be used: 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
be recommended that it should be made fast to.
diffusion with respect to the binding agent of the layer, by the introduction of special groups.v For information about such groups the following UL 2,179,238, 2,178,612, 2,186,849, 2,186,733, 2,186,851, ,186,719, 191,952, filed S. Patent Nos. 2,179,244, 2,186,732, 2,186,852, and application Ser.v No.
February 23, 1938, may be consulted. Y The group that is to impart fastness to diffusion may be introduced into the molecule of the color phenyl-pyroracemic acid,
henylenediamine or a de-' When the color former is former in the manner described in applications b methods; or the color former to dilfusion by said applications.
Hermann 'Lohaus, Dessau, by mesne assignments, to New York,
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 emulalso be made by distributing dif-' ferently sensitized emulsions having different color formers in the support.
form'of small particles on a produced in various manners, for example as described'in the U. S.
Patent Nos.
111,250, filed November 2,179,228, 2,179,238, 2,186,849, 6,730, and application Ser. 'No.
17, 1936. The image may be produced in the exposed emulsion layer by simple color development or by'reversal developthe U. S. Patent applications Ser.'No. 148,731, filed June 17, 1937, and U. S. Patent No. 2179,23 1.
In producing ,the aid of silver inaccordance be removed or black and wh'te pictures with halide emulsion layers produced with the invention the silver may may be left' in the layer with the dyestuff image.
The following tion Example 1.-To
examples illustrate the inven- 1 kilo of a silver halide emulsion 5 grams of the sodium salt of phenylpyro-' racemic acid of the formula CsH5-CHa-COCOOH are added and the emulsion is cast to form a layer.
The exposed layer yields on development withpara-dimethylaminoaniline a yellow 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. The
exposed layer yields on development with paradiethylaminoaniline image.
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. I
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;
aminoaniline a red dyestuifimage. v
Example 6.To 1 kilo of. asilven halide-emul;--
sion there are added 5 grams of the sodium saltof para-nitrophenyl-pyroracemic acid. and the emulsion is cast to form a layer. The exposed;
layer yields on development withpara-diethylaminoaniline a red dyestuff image.
Example 7..-T.o-1 kilo of a silver halide emul-.
353 pyroracemic acidethyl ester and the. emulsionv is.cast to-form a layer. The exposed layer yields on. development with para-diethylaminoaniline a yellow dyestufi image.
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.
Exam'pZe'15.-To'-1= kilo of a silver halide emulsion-there-are added5 grams of benzthiazole-Z pyroracemic acid corresponding with the formula substituted by an organic radicle having. an...
unsaturated double: bond; in. a. position adjacent: to the carbon atom of .said;methyl.group,-.to.react with the-oxidation: product or. an aromatic: deeveloper. 1
2;. In a process of producing v a'. photographic: color picture by dyestufi' formingidevelopment; the improvement Whichcomprisesacausing asithea dyestuff former a compoundri corresponding: with.
the 1 following general;fonnu1a'.E;iCH2;.-CO I-Rq, in which 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. I 1
3; In a: process of producing a photographiecolor picture by dyestuff' forming development, the improvement which comprises developin'gthe exposed photographic silver halide-emulsiomwith an. aromatic amino developer containing asthe dyestuif" former a: derivative of the pyroracemic acid; at leastthe methyl-'group-of said acid being substituted byan organic 'radicle havinganun saturated double loondin a position adjacent'to the carbon atom of'said methyl group; 7
4. In a process offproducing a: photographic' color picture by dyestufi forming development; the improvement which: comprises exposing. a photographic silver halide emulsion containing! as the dyestufi former a' derivative-ofthe. py roracemic acid, at'least-the methyl g1'oup=ofsaid.- acid being substitut'edby-an.organic'radicle hav ing an unsaturateddoublebond in a. position: ad jacent to the carbon atom of said methyligroup; and: developing' said emulsion with an aromaticamino developen' Y r l 5. In atprocess -of producing" a photographic color picture by dyestuif forming development} the improvementwhichcomprises 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.
6. 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.
7. 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. p
8. 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.
HERMANN LOHAUS.
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 (en) |
| BE (1) | BE433702A (en) |
| FR (1) | FR852803A (en) |
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/en 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 (en) | |
| FR852803A (en) | 1940-03-04 |
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