US2875057A - Benzoylacet-o-alkoxyanilide couplers for color photography - Google Patents

Benzoylacet-o-alkoxyanilide couplers for color photography Download PDF

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Publication number
US2875057A
US2875057A US575099A US57509956A US2875057A US 2875057 A US2875057 A US 2875057A US 575099 A US575099 A US 575099A US 57509956 A US57509956 A US 57509956A US 2875057 A US2875057 A US 2875057A
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Prior art keywords
mole
coupler
mixture
filtered
water
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US575099A
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English (en)
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Fred C Mccrossen
Paul W Vittum
Weissberger Arnold
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Eastman Kodak Co
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Eastman Kodak Co
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Priority to BE543742D priority Critical patent/BE543742A/xx
Priority to FR1152880D priority patent/FR1152880A/fr
Priority to DEE11703A priority patent/DE1000233B/de
Priority to GB36558/55A priority patent/GB800108A/en
Application filed by Eastman Kodak Co filed Critical Eastman Kodak Co
Priority to US575099A priority patent/US2875057A/en
Priority to FR71153D priority patent/FR71153E/fr
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Publication of US2875057A publication Critical patent/US2875057A/en
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    • 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
    • G03C7/362—Benzoyl-acetanilide couplers

Definitions

  • a distinctive feature of the coupler compounds having the above formulas residesjn. the; presence of the; alkoxyl group in the ortho position of only the anilide nucleus.
  • the benzoylacetanilide coupler compounds contain an alkoxyl group of from about 1 to 20 carbon atoms in the ortho position of the anilide group but contain no alkoxyl group on the benzoyl group but do contain an acylamido group attached directly to either the benzoyl or the anilideigroup of the coupler, as in the first general formula above, the coupler compounds possess properties separate and distinct from the coupler compounds of the mentioned. patents.
  • the accompanying drawing illustrates the distinctive features of the compounds of the invention.
  • the absorption curves 1, 2 and 3 of dyes obtained by development of a silver halide emulsion with a primary aromatic amino silver halide developer in the presence of the compounds 1, 2 andl 3 having the structures shown in the legend of the drawing.
  • a comparison of curves 1 and 2 shows that the effect of the introduction of the methoxyl group in the ortho position of the benzoyl group of compound 1 to obtain compound 2, is to shift the whole absorption curve toward the shorter wave lengths without altering its shape or sharpness of absorption.
  • the tan product is filtered, washed well with water, and dried.
  • the amorphous solid is recrystallized from 10-15 parts of methyl alcohol to yield 33 g. (56%) of white product which sinters at 72 C. and melts at 135-137 C., but occasionally contains alcohol of solvation and melts at 75-78 C.
  • Example 3 Coupler No. III is prepared as follows:
  • a-Benzoyl-Z-methoxy-Smitroacetanilide was placed 100 ml. of histological xylene, and 16.8 grams (0.1 mole) of 4-nitro-2-aminoanisole (Ber. 13, 389). grams (0.1 mole) of ethyl benzoylacetate was added all at once. After refluxing 2 hours, about 3-5 ml. of ethyl alcohol had been collected. The yellow solution was filtered hot and allowed to-cool to room temperature. The yellow solid which separated wasfiltered, washed with 50 ml.
  • the couplers isomeric to I and III are prepared similarly from the isomeric u-benzoyl methoxynitroacetanilides.
  • a-(m-Aminobenzoyl)-2-methoxyacetanilide In a 5- liter, three-necked flask, equipped with, stirrer, reflux condenser and addition tube, are placed 104 g. of technical-grade sodium sulfide (0.8 mole) and 200 ml. of water. The mixture is stirred gently on a steam bath'until solution is complete, and 3200 ml. of ethyl alcohol is added. The mixture is boiled and 126 g. (0.4 mole) of a-(m-nitrobenzoyl)-2-methoxyacetanilide is added portionwise over a period of fifteen minutes with good stir: ring.
  • the brown reaction mixture is heated at the boil ing point for one-half hour and poured on about an equal volume of ice.
  • To the cold solution is added 212 g. (4 moles) of solid ammonium chloride.
  • the mixture is stirred manually until the ammonium chloride is ,dissolved, and allowed to stand for forty minutes.
  • the product is' filtered by suction and washed on the funnel with several liters of water, until the washings are colorless.
  • the pale-yellow product is dissolved in 1600 ml. of boiling alcohol and 100 ml. of hot water added. A small amount of Darco is added, and the solution is filtered while hot.
  • the cooled filtrate yields 89.1 g. (78.5%) of flufly yellow product, M. P. 139.5-40 C.
  • the reaction mixture was drowned with stirring during fifteen minutes in 600 cc. of water, the product separating in white granules. Stirring was continued for forty-five minutes and the mixture filtered readily through a 5-inch Biichner funnel. The white solid was washed on the funnel with 2 liters of water, not over 20 C. Immediately, when the cake was no longer covered by water, it shrank in a characteristic manner away from the edge of the funnel as though threatening to become gummy. This change failed to occur as the cake was sucked and pressed thoroughly. The solid, which could be broken up easily, was air-dried, 60 g. being obtained; it had an indistinct melting range, starting at about C Twelve hundred cc.
  • Example 6 C-ouplerNo. VI is prepared as follows: u (4-nitr0benz0yl)-2-0ctadecyloxyacetanilide.-A mixture of 36.1 g. (0.10 mole) of Z-octadecyloxyaniline and 23.7g. (0.10 mole) of ethyl a-(4-nitrobenzoyl)acetate was heatedfor 1 /2 hours in 200ml. of boiling xylene under a steam-jacketed stillhead which permitted the removal of the xylene-alcohol azeo trope. The mixture was filtered hot and chilled. The bright yellow product was filtered, washed with methanol and dried; yield 41 g. (74%),MIP'I 80 81 C.
  • Boiliiig' was continued for twohour's. The mixture was cooled and filtered. The solid was recrystallized from acetic acid; yield 620g; (82%), M. P. 153-5 C. The melting point was raised to 157-8" C. after one more crystallization from acetic acid (with Norite).
  • Example 8 Coupler No. VIII is prepared as follows: oz-ben'zO'yl-4[2-(2.4-di-teit.-mfiylphenoay) 5' an'iifio benzamido]-2 methoxyacetanilide hydrochloride.-A mix ture of 6.7 g. (0.01 mole) of a-benzoyl-4[2 (2,4-di-tertamylphenoxy)-5-nitrobenzamido]' 2 methoxyacetani lide, 30 ml. of% ethanol, 20 m1. of water and140'm l. of glacial acetic acid was heated to the boiling point. To the solution was added 6.7 g.
  • Example 9 o-anisidine, 0.2 g. of anhydrous sodium acetatc and225 ml. of xylene was heated under a steam-heateddistillation columnfor 1% hours; as the ethanol-toluene a'zeotrope was distilled. Fifteen milliliters of solvent were distilled off and the distillant was filtered. Most of the xylene was distilledin vacuo from the filtrate, and the residue was treated with hexane. The solid was filtered and crystallized twice from acetonitrile. The yield of product was 7 g., M1 P. 166-7 C.
  • the isomeric Compound XV (a- ⁇ 3-[a-(2,4-di-n-amylphenoxy)butyramido] -benzoyl ⁇ - 2 methoxyacetanilide) was prepared in the same manner except using 2,4-di-namylphenol instead of 2,4-di-tert-amylphenol and was a white solid having a M..P. of 80 C.
  • Compounds XIV and XV are particularly valuable since they have lower melting points than, e. g., Compound IV which facilitates the incorporation of the compounds into gelatin emulsions by means of coupler solvents.
  • coupler compounds of the invention can be incorporated into silver halide emulsion layers by use of oily coupler solvents as described in the Mannes and Godowsky U. S. Patent 2,304,940, December 15, 1942, and the Jelley and Vittum U. S. Patent 2,322,027, June 15, 1943.
  • coupler compounds such as VI to IX containing terminal ester groups can also be hydrolyzed with alkali and when dissolved in aqueous alkaline solution can be incorporated directly into a silver halide emulsion.
  • Coupler IV 0.6 gram of coupler IV is dissolved in a mixture of 0.3 gram of di-n-butyl phthalate and 2.5 ml. of ethyl acetate by heating with stirring. This solution is mixed with 17.7 ml. of 10% gelatin solution containing 2 ml. of 5% Alkanol B. The mixture is put through a colloid mill four times to eifect dispersion. Fourteen ml. of
  • water is used to rinse out the colloid mill and this is added to the dispersion.
  • the dispersion is then chilled and allowed to set. It is then shredded and dried on a stainless steel screen to remove the water and the ethyl acetate.
  • the dried dispersion is then added to 33 ml. of water and allowed to soak for 20 minutes.
  • the mixture is then warmed to 40 C. to melt the gelatin.
  • the melted dispersion is mixed with 8.5 ml. of a sensitive silver halide emulsion and the resulting mixture is coated in the normal manner upon a film base support.
  • the resulting film is then exposed under an image and developed in a color developing composition as follows:
  • the result is to obtain a silver and yellow dye image in the emulsion layer from which the silver image can be removed by well-known methods.
  • the dye image thus obtained has light absorption properties similar to that obtained from compound 3 (Compound HI of Example 3) as shown in the drawing.
  • Similar results are obtained when the other couplers of the invention are incorporated into silver halide emulsion layers and developed by means of p-phenylenediamine developer compositions.
  • any color-forming developer containing a primary amino group may be used.
  • These compounds are usually used in the salt form, such as the hydrochloride or the sulfate which are more'stable than the amines themselves.
  • the suitable compounds are diethyl-p-phenylenediamine hydrochlo-' ride, monomethyl-p-phenylenediamine hydrochloride, dimethyl-p-phenylenediamine hydrochloride and 2-amino- S-diethylaminotoluene hydrochloride.
  • the p-aminophenols and their substitution products may also be used where the amino group is unsubstituted. All of these developers have an unsubstituted amino group which enables the oxidation products of the developer to couple with the color-forming compounds to form a dye image.
  • emulsion layers containing the couplers contain as the emulsion vehicle gelatin or other water-permeable organic colloids such as albumin, partially hydrolyzed cellulose esters and partially hydrolyzed polyvinyl esters, polyvinyl alcohol, etc.
  • the carrier may be supported by a transparent medium such as glass, a cellulose ester or synthetic resin or a non-transparent reflecting medium such as paper or an opaque cellulose ester.
  • the emulsion may be coated as a single layer on the support or as one of a number of superposed layers on one or both sides of the support.
  • the superposed layers may be diiferentially sensitized as is conventional in color photography.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US575099A 1954-12-20 1956-03-30 Benzoylacet-o-alkoxyanilide couplers for color photography Expired - Lifetime US2875057A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
BE543742D BE543742A (ja) 1954-12-20
FR1152880D FR1152880A (fr) 1954-12-20 1955-12-14 Nouveaux benzoylacétanilides et leurs applications notamment pour la photographie en couleurs
DEE11703A DE1000233B (de) 1954-12-20 1955-12-17 Farbenphotographisches Material mit mindestens einer photographischen, einen alkoxylierten Benzoylacetanilidkuppler enthaltenden Halogensilberemulsion
GB36558/55A GB800108A (en) 1954-12-20 1955-12-20 Improved colour couplers for use in colour photography
US575099A US2875057A (en) 1954-12-20 1956-03-30 Benzoylacet-o-alkoxyanilide couplers for color photography
FR71153D FR71153E (fr) 1954-12-20 1957-03-30 Nouveaux benzoylacétanilides et leurs applications notamment pour la photographie en couleurs

Applications Claiming Priority (2)

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US47615954A 1954-12-20 1954-12-20
US575099A US2875057A (en) 1954-12-20 1956-03-30 Benzoylacet-o-alkoxyanilide couplers for color photography

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BE (1) BE543742A (ja)
DE (1) DE1000233B (ja)
FR (2) FR1152880A (ja)
GB (1) GB800108A (ja)

Cited By (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3056674A (en) * 1961-02-01 1962-10-02 Gen Aniline & Film Corp Color formers for producing yellow dye images by color development
DE1285885B (de) * 1964-02-01 1968-12-19 Fuji Photo Film Co Ltd Farbfotografisches Aufzeichnungsmaterial
US3472145A (en) * 1962-08-31 1969-10-14 Ciba Ltd Silver halide emulsions containing acylacetylamino couplers containing sulfuric acid ester groups
US3503748A (en) * 1962-08-31 1970-03-31 Ciba Ltd Light-sensitive photographic silver halide layer for the color developing process
US4409323A (en) * 1980-02-15 1983-10-11 Konishiroku Photo Industry Co., Ltd. Silver halide photographic material
EP0112162A2 (en) 1982-12-13 1984-06-27 Konica Corporation Light-sensitive silver halide photographic material
EP0124795A2 (en) 1983-04-11 1984-11-14 Fuji Photo Film Co., Ltd. Silver halide photographic emulsion
EP0143570A2 (en) 1983-11-02 1985-06-05 Konica Corporation Silver halide color photographic material
EP0147854A2 (en) 1983-12-29 1985-07-10 Fuji Photo Film Co., Ltd. Silver halide photographic light-sensitive materials
EP0200502A2 (en) 1985-04-30 1986-11-05 Konica Corporation Light-sensitive silver halide color photographic material
EP0201033A2 (en) 1985-04-30 1986-11-12 Konica Corporation A method for processing silver halide color photographic materials
EP0200878A1 (en) 1982-02-24 1986-11-12 Konica Corporation Light-sensitive silver halide color photographic material
EP0202616A2 (en) 1985-05-16 1986-11-26 Konica Corporation Method for color-developing a silver halide photographic light-sensitive material
EP0204530A2 (en) 1985-05-31 1986-12-10 Konica Corporation Method for forming direct positive color image
EP0204175A1 (en) 1985-05-09 1986-12-10 Fuji Photo Film Co., Ltd. Silver halide color photographic materials
EP0228914A2 (en) 1985-12-28 1987-07-15 Konica Corporation Method of processing lightsensitive silver halide color photographic material
EP0253390A2 (en) 1986-07-17 1988-01-20 Fuji Photo Film Co., Ltd. Photographic support and color photosensitive material
EP0266797A2 (en) 1986-11-07 1988-05-11 Fuji Photo Film Co., Ltd. Method of processing silver halide color photographic material and photographic color developing composition
US5021333A (en) * 1989-09-05 1991-06-04 Eastman Kodak Company Color photographic element, compounds and process
EP0452984A1 (en) 1985-09-25 1991-10-23 Fuji Photo Film Co., Ltd. Process for processing silver halide color photographic material for photographing use
US5118599A (en) * 1991-02-07 1992-06-02 Eastman Kodak Company Yellow couplers for photographic elements and processes
EP0574090A1 (en) 1992-06-12 1993-12-15 Eastman Kodak Company One equivalent couplers and low pKa release dyes
US5360713A (en) * 1992-11-12 1994-11-01 Eastman Kodak Company Yellow dye-forming couplers and color photographic elements containing these couplers
US5427898A (en) * 1992-12-04 1995-06-27 Eastman Kodak Company Yellow couplers having an arloxy coupling-off group which contains an ortho polarizable functional group
EP0684515A1 (en) 1994-05-27 1995-11-29 Eastman Kodak Company Photographic element and process incorporating a high dye-yield image coupler providing improved granularity
EP0686873A1 (en) 1994-06-08 1995-12-13 Eastman Kodak Company Color photographic element containing new epoxy scavengers for residual magenta coupler
EP0695968A2 (en) 1994-08-01 1996-02-07 Eastman Kodak Company Viscosity reduction in a photographic melt
EP0698816A1 (en) 1994-08-26 1996-02-28 Eastman Kodak Company Photographic paper formed with low molecular weight polyvinyl alcohol having low oxygen permeability
US5571661A (en) * 1994-06-09 1996-11-05 Konica Corporation Silver halide light-sensitive color photographic material
EP0777151A2 (en) 1995-11-30 1997-06-04 Eastman Kodak Company Photographic element containing yellow dye-forming coupler comprising a dye light stability enhancing ballast and process
EP0779536A1 (en) 1995-12-04 1997-06-18 Konica Corporation Light-and heat-sensitive recording material and recording method by use thereof
EP0779544A1 (en) 1995-12-11 1997-06-18 Eastman Kodak Company Photographic element containing an improved pyrazolotriazole coupler
EP0779543A1 (en) 1995-12-11 1997-06-18 Eastman Kodak Company Photographic element containing an improved pyrazolotriazole coupler
US5939244A (en) * 1997-09-26 1999-08-17 Eastman Kodak Company Photographic coupler and element
WO2013032827A1 (en) 2011-08-31 2013-03-07 Eastman Kodak Company Motion picture films to provide archival images

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1239317A (ja) * 1957-06-19 1960-12-16
GB852922A (en) * 1957-09-04 1960-11-02 Gen Aniline & Film Corp Color formers containing a m-alkylphenoxyacyl group

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2678882A (en) * 1952-01-23 1954-05-18 Eastman Kodak Co Aromatic sulfonyl halinde couplers for color photography

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2678882A (en) * 1952-01-23 1954-05-18 Eastman Kodak Co Aromatic sulfonyl halinde couplers for color photography

Cited By (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3056674A (en) * 1961-02-01 1962-10-02 Gen Aniline & Film Corp Color formers for producing yellow dye images by color development
US3472145A (en) * 1962-08-31 1969-10-14 Ciba Ltd Silver halide emulsions containing acylacetylamino couplers containing sulfuric acid ester groups
US3503748A (en) * 1962-08-31 1970-03-31 Ciba Ltd Light-sensitive photographic silver halide layer for the color developing process
DE1285885B (de) * 1964-02-01 1968-12-19 Fuji Photo Film Co Ltd Farbfotografisches Aufzeichnungsmaterial
US4409323A (en) * 1980-02-15 1983-10-11 Konishiroku Photo Industry Co., Ltd. Silver halide photographic material
EP0200878A1 (en) 1982-02-24 1986-11-12 Konica Corporation Light-sensitive silver halide color photographic material
EP0112162A2 (en) 1982-12-13 1984-06-27 Konica Corporation Light-sensitive silver halide photographic material
EP0124795A2 (en) 1983-04-11 1984-11-14 Fuji Photo Film Co., Ltd. Silver halide photographic emulsion
EP0143570A2 (en) 1983-11-02 1985-06-05 Konica Corporation Silver halide color photographic material
EP0147854A2 (en) 1983-12-29 1985-07-10 Fuji Photo Film Co., Ltd. Silver halide photographic light-sensitive materials
EP0201033A2 (en) 1985-04-30 1986-11-12 Konica Corporation A method for processing silver halide color photographic materials
EP0200502A2 (en) 1985-04-30 1986-11-05 Konica Corporation Light-sensitive silver halide color photographic material
EP0204175A1 (en) 1985-05-09 1986-12-10 Fuji Photo Film Co., Ltd. Silver halide color photographic materials
EP0202616A2 (en) 1985-05-16 1986-11-26 Konica Corporation Method for color-developing a silver halide photographic light-sensitive material
EP0204530A2 (en) 1985-05-31 1986-12-10 Konica Corporation Method for forming direct positive color image
EP0452984A1 (en) 1985-09-25 1991-10-23 Fuji Photo Film Co., Ltd. Process for processing silver halide color photographic material for photographing use
EP0228914A2 (en) 1985-12-28 1987-07-15 Konica Corporation Method of processing lightsensitive silver halide color photographic material
EP0253390A2 (en) 1986-07-17 1988-01-20 Fuji Photo Film Co., Ltd. Photographic support and color photosensitive material
EP0266797A2 (en) 1986-11-07 1988-05-11 Fuji Photo Film Co., Ltd. Method of processing silver halide color photographic material and photographic color developing composition
US5021333A (en) * 1989-09-05 1991-06-04 Eastman Kodak Company Color photographic element, compounds and process
US5118599A (en) * 1991-02-07 1992-06-02 Eastman Kodak Company Yellow couplers for photographic elements and processes
EP0574090A1 (en) 1992-06-12 1993-12-15 Eastman Kodak Company One equivalent couplers and low pKa release dyes
US5360713A (en) * 1992-11-12 1994-11-01 Eastman Kodak Company Yellow dye-forming couplers and color photographic elements containing these couplers
US5427898A (en) * 1992-12-04 1995-06-27 Eastman Kodak Company Yellow couplers having an arloxy coupling-off group which contains an ortho polarizable functional group
EP0684515A1 (en) 1994-05-27 1995-11-29 Eastman Kodak Company Photographic element and process incorporating a high dye-yield image coupler providing improved granularity
EP0686873A1 (en) 1994-06-08 1995-12-13 Eastman Kodak Company Color photographic element containing new epoxy scavengers for residual magenta coupler
US5571661A (en) * 1994-06-09 1996-11-05 Konica Corporation Silver halide light-sensitive color photographic material
EP0695968A2 (en) 1994-08-01 1996-02-07 Eastman Kodak Company Viscosity reduction in a photographic melt
EP0698816A1 (en) 1994-08-26 1996-02-28 Eastman Kodak Company Photographic paper formed with low molecular weight polyvinyl alcohol having low oxygen permeability
EP0777151A2 (en) 1995-11-30 1997-06-04 Eastman Kodak Company Photographic element containing yellow dye-forming coupler comprising a dye light stability enhancing ballast and process
EP0779536A1 (en) 1995-12-04 1997-06-18 Konica Corporation Light-and heat-sensitive recording material and recording method by use thereof
EP0779544A1 (en) 1995-12-11 1997-06-18 Eastman Kodak Company Photographic element containing an improved pyrazolotriazole coupler
EP0779543A1 (en) 1995-12-11 1997-06-18 Eastman Kodak Company Photographic element containing an improved pyrazolotriazole coupler
US5939244A (en) * 1997-09-26 1999-08-17 Eastman Kodak Company Photographic coupler and element
WO2013032827A1 (en) 2011-08-31 2013-03-07 Eastman Kodak Company Motion picture films to provide archival images

Also Published As

Publication number Publication date
FR1152880A (fr) 1958-02-26
GB800108A (en) 1958-08-20
FR71153E (fr) 1959-10-13
BE543742A (ja)
DE1000233B (de) 1957-01-03

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