US3649287A - Method of incorporating photographic ingredients into a photographic colloid - Google Patents

Method of incorporating photographic ingredients into a photographic colloid Download PDF

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Publication number
US3649287A
US3649287A US889722A US3649287DA US3649287A US 3649287 A US3649287 A US 3649287A US 889722 A US889722 A US 889722A US 3649287D A US3649287D A US 3649287DA US 3649287 A US3649287 A US 3649287A
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water
soluble
group
gelatin
photographic
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US889722A
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Alfons Jozef De Pauw
Jan Albert Carpentier
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Agfa Gevaert NV
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Agfa Gevaert NV
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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
    • G03C1/00—Photosensitive materials
    • G03C1/76—Photosensitive materials characterised by the base or auxiliary layers
    • G03C1/825—Photosensitive materials characterised by the base or auxiliary layers characterised by antireflection means or visible-light filtering means, e.g. antihalation
    • 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
    • G03C1/00—Photosensitive materials
    • G03C1/005—Silver halide emulsions; Preparation thereof; Physical treatment thereof; Incorporation of additives therein
    • 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
    • G03C7/388—Processes for the incorporation in the emulsion of substances liberating photographically active agents or colour-coupling substances; Solvents therefor

Definitions

  • the method comprises the steps of 1. dissolving the photographic ingredient in a photographically inert organic liquid consisting essentially of V tetrahydrothiophene-l,l-dioxide, N-methyl-2- pyrrolidinone, ethylene glycol, glycerol, acetonitrile or formamide. 2. forming a dispersion of the photographic ingredient by mixing the solution obtained with an aqueous solution K of a hydrophilic photographically inert colloid miscible v with gelatin more particularly a colloid of the following classes A to C Le.
  • water-soluble modified natural colloid substances selected from the group of:
  • non-ionic starches anionic starches water-soluble alginic acid derivatives non-ionic cellulose gums anionic cellulose gums
  • C Synthetic water-soluble resins selected from the 92. Qn n Qf n r m s ami-a rline i y alcohol, N-binylpyrrolidinone, vinyl methyl ether, acrylic acid and salts thereof, methacrylic acid groups and salts thereof, maleic acid salts thereof or acrylamide units, maleic anhydride, water-soluble polymers containing alkylene oxide units, water-soluble prepolycondensates and polycondensate that are miscible with gelatin and selected from the group consisting of water-soluble urea-formaldehyde, water-soluble melamine formaldehyde, water-soluble guanamineformaldehyde, water-soluble alkyd and water-soluble .B9 Y FF es and 3.
  • the present application is a continuation-in-part applica tion of our copending application Ser. No. 511,969 filed Dec. 6, 1965, now abandoned BACKGROUND OF THE INVENTION
  • the invention relates to the field of the preparation of photographic silver halide emulsion materials and more particularly to a method of incorporating photographic ingredients in a light-sensitive gelatin silver halide emulsion.
  • the color couplers containing a water-solubilizing group such as a sulfonic acid (salt) group or carboxylic acid (salt) group cause an increase of the viscosity of colloid solutions containing gelatin.
  • a water-solubilizing group such as a sulfonic acid (salt) group or carboxylic acid (salt) group
  • the present invention is directed to a process for incorporating photographic ingredients that are only slightly watersoluble and contain a water-solubilizing group, e.g., of the type of a sulphonic acid or carboxylic acid group in free acid or salt form in a gelatin silver halide emulsion.
  • a water-solubilizing group e.g., of the type of a sulphonic acid or carboxylic acid group in free acid or salt form in a gelatin silver halide emulsion.
  • Said process comprises the steps of 1. dissolving the photographic ingredient in a photographically inert organic liquid consisting essentially of tetrahydrothiophene-l l -dioxide, N-methyl-Z-pyrrolidinone, ethylene glycol, glycerol, acetonitrile or formamide,
  • B water-soluble modified natural colloid substances selected from the group of a. nonionic starches b. anionic starches c. water-soluble alginic acid derivatives d. nonionic cellulose gums e. anionic cellulose gums C.
  • Synthetic water-soluble resins selected from the group consisting of vinyl polymers containing vinyl alcohol, N-vinylpyrrolidinone, vinyl methyl ether, maleic anhydride, acrylic acid and salts thereof, methacrylic acid groups and salts thereof, maleic acid and salts thereof or acrylamide units, water-soluble polymers containing alkylene oxide units, water-soluble prepolycondensates and polycondensates that are miscible with gelatin and selected from the group consisting of water-soluble urea-formaldehyde, water-soluble melamine formaldehyde, water-soluble guanamine-formaldehyde, water-soluble alkyd and water-soluble polyester resins, and
  • color couplers that are poorly water-soluble and contain a water-solubilizing group, salt forming or salt group from a concentrated stock solution without necessitating the use of alkali'and a pl-l-adjustment of the silver halide emulsion.
  • a photographically inert protective colloid that does not interact like gelatin does with the photographic ingredient makes it possible to prepare stock solutions not suffering from viscosity changes during long storage time.
  • slightly or poorly water-soluble photographic ingredient a photographic ingredient such as a dye, e.g., a dye suited for use in a filter or antihalation layer, a color coupler, a mask-forming compound or a developing agent, that practically does not dissolve in water at room temperature although containing a water-solubilizing group, more particularly an ingredient that dissolves for at most 2 g. per ml. of water at a temperature of 20 C.
  • a dye e.g., a dye suited for use in a filter or antihalation layer, a color coupler, a mask-forming compound or a developing agent, that practically does not dissolve in water at room temperature although containing a water-solubilizing group, more particularly an ingredient that dissolves for at most 2 g. per ml. of water at a temperature of 20 C.
  • the photographic ingredients suitable for incorporation into a photographic silver halide emulsion according to the method of the present invention may contain long chain residues to render them fast to difl usion in photographic colloid layers.
  • starch acetates e.g., corn starch acetates containing 1 to 4 percent of acetyl groups.
  • hydroxyl alkyl starch derivatives e.g., hydroxyethyl and hydroxypropyl starch derivatives.
  • Anionic starches are produced by the introduction of carboxyl, sulphonic acid, sulphuric acid or phosphoric acid groups into starch. This permits the preparation of water-soluble alkali metal or ammonium salts.
  • the class of nonionic cellulose gums includes, e.g., hydroxy alkyl cellulose derivatives and polyoxyalkylene cellulose derivatives.
  • Anionic cellulose gums are produced by the introduction of carboxyl, sulphonic acid, sulphuric acid or phosphoric acid groups into cellulose. This permits the preparation of the corresponding water-soluble alkali metal or ammonium salts.
  • anionic cellulose gums are more particularly mentioned carboxymethylcellulose, methyl cellulose-m-sulfobenzoate, ethyl cellulose-sulfosuccinate and acetyl cellulose sulfosuccinate.
  • copoly styrene/maleic anhydride (50/50)
  • water-soluble homoand copolymers of ethylene oxide and/or propylene oxide e.g., the water-soluble alkylene oxide units containing polymers described in the US. Pat. specification No. 2,848,330 and the United Kingdom Pat. specifications Nos. 920,637945,857-945,340 and 940,051 and further watersoluble-melamine-formaldehyde resins.
  • the amount of the water-soluble colloid(s) which are added to a gelatin silver halide emulsion together with the photo graphic ingredient can be comprised between 5 percent and 33 percent by weight in respect of the total weight of binder of the silver halide grains and is preferably between 15 percent and 25 percent.
  • the solvent or solvents can be removed by washing the gelled and noodled light-sensitive composition, or by evaporation from the gelled light-sensitive emulsion under vacuum.
  • Remaining amounts of the polar solvents used in the present invention do not cause desensitization or fogging of the lightsensitive silver halide emulsion.
  • a slightly water-soluble color coupler containing (a) sulphonic acid or (a) carboxylic acid group(s) in free acid or salt form is dissolved, normally by heating preferably between 50 and 80 C. in one of the said polar solvents or a mixture of such a polar solvent and a solvent having a dielectric constant at 20 C. lower than that of ethylene glycol, the less polar solvent however being present only in minor amounts (e.g., 5 to percent by weight) and the solution obtained is thoroughly mixed with a solution of at least one of the said water-soluble high-molecular weight compounds which are dissolved in water or a mixture of water and one of the said polar solvents.
  • a stable transparent composition can be formed, which can be stored for weeks.
  • the said composition is preferably incorporated by stirring into the melted gel of the light-sensitive gelatin silver halide emulsion whereupon the composition obtained is gelled and the polar solvent(s) is (are) removed at least partially by washing the gelled composition with water.
  • the photographic coatings when prepared according to the color coupler incorporating technique as described above, produce on color development very sharp, highly transparent colored images.
  • a little wetting agent facilitates the dispersion of the photographic ingredient in the hydrophilic colloid medium.
  • suitable moistening agents are saponin, arylalkyl sulphonates and polyoxyalkylene compounds, more particularly:
  • n is a positive integer from 5 to 50.
  • SOaNB is dissolved at 60 C in 10 ml. of tetrahydrothiophene-l :ldioxide.
  • the solution obtained is added, while stirring, to a solution of l gm. of ethyl cellulose-a-(B-sulpho )monosuccinate (DS ethoxy 2.2, DS B-sulpho monosuccinic acid ester 0.8, viscosity at 20 C. of a 2 percent solution in water 4 cp.) and 1 ml. of saponine, in 10 ml. of water.
  • a homogeneous and very fine dispersion of color coupler is obtained.
  • the said dispersion is mixed at a temperature of 38 C. with 50 gm. of a red-sensitized silver bromoiodide emulsion containing 0.33 mole of silver bromide, 0.0075 mole of silver iodide and gm. of gelatin per kg. of emulsion.
  • the emulsion is coated onto a cellulose triacetate support and the coating is dried at 40 C.
  • EXAMPLE 2 1 gm. of color coupler having the following structural formula is dissolved at 50 C in 10 ml. of N-methyl-2-pyrrolidinone. The solution obtained is added, while stirring, to a solution of 1 gm. of hydroxy ethyl cellulose (DS 0.85, MS:l.33 and viscosity of a 2 percent aqueous solution at 20 C.: l 1.2 cp.), and 1 ml. of saponine in IQ ml. of water.
  • 1 gm. of hydroxy ethyl cellulose DS 0.85, MS:l.33 and viscosity of a 2 percent aqueous solution at 20 C.: l 1.2 cp.
  • a homogeneous and very fine dispersion of color coupler is obtained.
  • the said dispersion is mixed at a temperature of 38 C. with 50 gm. of a green-sensitized silver bromoiodide emulsion containing 0.33 mole of silver bromide, 0.0075 mole of silver iodide and gm. of gelatin per kg.
  • the emulsion obtained is allowed to cool and the obtained gel noodled and washed for 90 minutes with cold water. The noodles are then remelted at 50 C whereupon the emulsion is coated in the usual manner.
  • EXAMPLE 3 1 gm. of color coupler having the following structural formula is dissolved at 60 C in 10 ccs. of formamide. The solution obtained is added, while stirring, to a solution of l g. of methyl cellulose-m-sulphobenzoate (DS methoxy L78, B8 msulphobenzoic acid ester 0.62, viscosity of a 2 percent aqueous solution at 20 C. 3.5 cp.) and 1 ml. of saponine in 10 ml. of water.
  • a solution of l g. of methyl cellulose-m-sulphobenzoate DS methoxy L78, B8 msulphobenzoic acid ester 0.62, viscosity of a 2 percent aqueous solution at 20 C. 3.5 cp.
  • a homogeneous and very fine dispersion of color coupler is obtained.
  • the said dispersion is mixed at a temperature of 38 C. with 60 gm. of a positive silver bromoiodide emulsion containing 80 gm. of gelatin, 0.33 mole of silver bromide and 0.0075 mole of silver iodide.
  • the emulsion is coated onto a cellulose triacetate support and then dried at 40C.
  • EXAMPLE 4 1 gm. of color coupler having the following structural formula:
  • a homogeneous and very fine dispersion of color coupler is obtained.
  • the said dispersion is mixed at a temperature of 38 C. with 60 gm. of a positive silver bromoiodide emulsion containing 80 gm. of gelatin, 0.33 mole of silver bromide and 0.0075 mole of silver iodide.
  • the emulsion is coated onto a cellulose triacetate support whereupon the coating is dried at 40 C.
  • SO Na is dissolved at 80 C. in 10 ml. of glycerol.
  • the solution obtained is added while stirring to a solution in 10 ml. of water of 1 gm. of copoly (styrene/maleic anhydride)( 50/50) (intrinsic viscosity [1;] measured at C. in acetone 0.22) and 1 ml. of saponine.
  • a homogeneous and very fine dispersion of color coupler is obtained.
  • the said dispersion is mixed at a temperature of 38 C. with 60 gm. of a positive silver bromoiodide emulsion containing 80 gm. of gelatin, 0.33 mole of silver bromide and 0.0075 mole of silver iodide.
  • the emulsion is coated onto a cellulose triacetate support whereupon the coating is dried at 40 C.
  • a homogeneous and very fine dispersion of color coupler is obtained.
  • the said dispersion is mixed at a temperature of 38 C. with 60 gm. of a positive silver bromoiodide emulsion containing 80 gm. of gelatin, 0.33 mole of silver bromide and soan 0:0 N l I ll mcc-Nncois dissolved at 60 C. in 10 ml. of dimethyl sulphoxide.
  • the solution obtained is added, while stirring to a solution of 1 gm. of hydroxy ethyl cellulose (DS 0.85, MS 1.33, viscosity at 20 C. of a 2 percent aqueous solution l 1.2 cp.), and 1 ml. of saponine in 10 ml. of water.
  • a homogeneous and very fine dispersion of color coupler is obtained.
  • the said dispersion is mixed at a temperature of 38 C. with 60 gm. of silver bromo-iodide emulsion containing 0.33 mole of silver bromide, 0.0075 mole of silver iodide and gm. of gelatin per kg. of emulsion.
  • the emulsion is coated onto a cellulose triacetate support whereupon the coating is dried at 40 C.
  • EXAMPLE 8 1 gm. of color coupler having the following structural formula is dissolved at 60 C. in i0 ml. of formamide. The solution obtained is added while stirring to a solution of l g. of NIKRU- LAN HW (Registered Trademark for a water-soluble melamine-formaldehyde textile resin of Cassella Farbwerke Mainkur A.G. Frankfurt (Main) W-Germany) in 10 ml. of water.
  • NIKRU- LAN HW Registered Trademark for a water-soluble melamine-formaldehyde textile resin of Cassella Farbwerke Mainkur A.G. Frankfurt (Main) W-Germany
  • a homogeneous and very fine dispersion of color coupler is obtained.
  • the said dispersion is mixed at a temperature of 38 C. with 60 gm. of a positive silver bromo-iodide emulsion containing 80 gm. of gelatin, 0.33 mole of silver bromide and 0.0075 mole of silver iodide.
  • the emulsion is coated onto a cellulose triacetate support whereupon the coating is dried at 40 C.
  • EXAMPLE 9 1 gm. of color coupler as described in example 8 is dissolved at 60 C. in formamide. The thus obtained solution is added while stirring to a solution of 1 gm. of methyl cellulose-msulphobenzoate (DS methoxy 1.78, DS m-sulphobenzoic acid ester 0.62, viscosity of a 2 percent aqueous solution at 20 C. 3.5 cp.) in 5 ml. of formamide. The solution obtained is mixed at a temperature of 38 C. with a mixture of 60 gm. of a positive emulsion as described in example 8, 20 ml. of water and 1 ml. of saponine. The thus prepared light-sensitive composition is coated onto a cellulose triacetate support and dried at 40 C.
  • methyl cellulose-msulphobenzoate DS methoxy 1.78, DS m-sulphobenzoic acid ester 0.62, viscosity of a 2 percent aqueous solution at 20
  • EXAMPLE l0 1 gm. of color coupler as described in example 5 is dissolved in 5 ml. of ethylene glycol. The obtained solution is added while stirring to a solution of 1 gm. of copoly(styrene/maleic anhydride) (50/50) (intrinsic viscosity [1;] measured at 25 C.
  • i acetone 012) i a mi of L of meth ol and 5 l, to the desired thickness in order to form a yellow lilter layer. of water.
  • the thus obtained solution is mixed at a temperature we l im: of 38 C. with a mixture of 60 gm. of a p i i l i as l.
  • gelatin gel i.e., a gelatin sol or gelatin solution
  • sisting of agar-agar, amylose, amylopectine, nonionic EXAMPLE l2 starches, anionic starches, water-soluble alginic acid Example 11 is repeated but in lieu of l gm. of the cellulose derivatives, nonionic cellulose gums, anionic cellulose derivative, 1 gm.
  • a very fine dispersion of the dye is obtained formaldehyde watef'sPluble melammefmmaldehlde, which can be homogeneously mixed with a melted gelatin gel water'soluble guanamme-fol'maldellyde Water-Soluble or coated directly as a filter layer on a transparent support.
  • alkyd and walersoluble Polyester "isms, and EXAMPLE 14 3. homogeneously distributing the obtained dispersion into 0 5 gm EYE d f example 1 1 i dissolved at 15 a gelatin solution or a photographic gelatino silver halide ml. of formamide. The solution obtained is added, while stiremulsion ring, to a solution of 1 gm.
  • the 50 water-solubililing group being a carboxylic acid or sulphonic solution obtained can be incorporated homogeneously in a acid groupsln free acid or Salt formmelted gelatin gel or coated directly on a transparent support

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
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US889722A 1965-01-25 1969-12-31 Method of incorporating photographic ingredients into a photographic colloid Expired - Lifetime US3649287A (en)

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GB3150/65A GB1099416A (en) 1965-01-25 1965-01-25 Method of incorporating photographic ingredients into a photographic colloid

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BE (1) BE675530A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
CH (1) CH472058A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
DE (1) DE1522352A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
FR (1) FR1475750A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
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Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4214047A (en) * 1979-05-04 1980-07-22 Eastman Kodak Company Photographic elements having hydrophilic colloid layers containing hydrophobic addenda uniformly loaded in latex polymer particles
US4247627A (en) * 1979-10-10 1981-01-27 Eastman Kodak Company Photographic elements having hydrophilic colloid layers containing hydrophobic ultraviolet absorbers uniformly loaded in latex polymer particles
US4395479A (en) * 1981-09-23 1983-07-26 J. T. Baker Chemical Company Stripping compositions and methods of stripping resists
US4430422A (en) 1982-01-26 1984-02-07 Agfa-Gevaert, N.V. Method of dispersing photographic adjuvants in a hydrophilic colloid composition
US4957857A (en) * 1988-12-23 1990-09-18 Eastman Kodak Company Stabilization of precipitated dispersions of hydrophobic couplers
US5015564A (en) * 1988-12-23 1991-05-14 Eastman Kodak Company Stabilizatin of precipitated dispersions of hydrophobic couplers, surfactants and polymers
US5087554A (en) * 1990-06-27 1992-02-11 Eastman Kodak Company Stabilization of precipitated dispersions of hydrophobic couplers
US5256527A (en) * 1990-06-27 1993-10-26 Eastman Kodak Company Stabilization of precipitated dispersions of hydrophobic couplers
US5607828A (en) * 1996-06-14 1997-03-04 Eastman Kodak Company High chloride {100} tabular grain emulsions improved by peptizer modification
US20030148129A1 (en) * 2000-02-25 2003-08-07 Nippon Paint Co., Ltd Method of forming composite coating film
US20040224169A1 (en) * 2001-09-11 2004-11-11 Daicel Polymer Ltd. Plated resin molded article and process for producing the same

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2870012A (en) * 1955-12-23 1959-01-20 Eastman Kodak Co Microdispersions of photographic color couplers
US3050394A (en) * 1959-09-30 1962-08-21 Gen Aniline & Film Corp Method of incorporating color couplers in hydrophlic colloids
US3287133A (en) * 1963-03-01 1966-11-22 Eastman Kodak Co Photographic dye developer dispersions utilizing water-soluble sulfites

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2870012A (en) * 1955-12-23 1959-01-20 Eastman Kodak Co Microdispersions of photographic color couplers
US3050394A (en) * 1959-09-30 1962-08-21 Gen Aniline & Film Corp Method of incorporating color couplers in hydrophlic colloids
US3287133A (en) * 1963-03-01 1966-11-22 Eastman Kodak Co Photographic dye developer dispersions utilizing water-soluble sulfites

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4214047A (en) * 1979-05-04 1980-07-22 Eastman Kodak Company Photographic elements having hydrophilic colloid layers containing hydrophobic addenda uniformly loaded in latex polymer particles
US4247627A (en) * 1979-10-10 1981-01-27 Eastman Kodak Company Photographic elements having hydrophilic colloid layers containing hydrophobic ultraviolet absorbers uniformly loaded in latex polymer particles
US4395479A (en) * 1981-09-23 1983-07-26 J. T. Baker Chemical Company Stripping compositions and methods of stripping resists
US4430422A (en) 1982-01-26 1984-02-07 Agfa-Gevaert, N.V. Method of dispersing photographic adjuvants in a hydrophilic colloid composition
US4957857A (en) * 1988-12-23 1990-09-18 Eastman Kodak Company Stabilization of precipitated dispersions of hydrophobic couplers
US5015564A (en) * 1988-12-23 1991-05-14 Eastman Kodak Company Stabilizatin of precipitated dispersions of hydrophobic couplers, surfactants and polymers
US5087554A (en) * 1990-06-27 1992-02-11 Eastman Kodak Company Stabilization of precipitated dispersions of hydrophobic couplers
US5256527A (en) * 1990-06-27 1993-10-26 Eastman Kodak Company Stabilization of precipitated dispersions of hydrophobic couplers
US5607828A (en) * 1996-06-14 1997-03-04 Eastman Kodak Company High chloride {100} tabular grain emulsions improved by peptizer modification
US20030148129A1 (en) * 2000-02-25 2003-08-07 Nippon Paint Co., Ltd Method of forming composite coating film
US20040224169A1 (en) * 2001-09-11 2004-11-11 Daicel Polymer Ltd. Plated resin molded article and process for producing the same

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BE675530A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1966-05-16
DE1522352A1 (de) 1969-07-24
FR1475750A (fr) 1967-04-07
NL6600628A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1966-03-25
GB1099416A (en) 1968-01-17
CH472058A (de) 1969-04-30

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