US2792303A - Process for the production of diazotype copies - Google Patents

Process for the production of diazotype copies Download PDF

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Publication number
US2792303A
US2792303A US308938A US30893852A US2792303A US 2792303 A US2792303 A US 2792303A US 308938 A US308938 A US 308938A US 30893852 A US30893852 A US 30893852A US 2792303 A US2792303 A US 2792303A
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United States
Prior art keywords
diazo
compound
film layer
light
diazotype
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US308938A
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Sanders Theodorus Pe Wilhelmus
Wilders Johannes Henri Andreas
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Chemische Fabriek L Van der Grinten NV
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Grinten Chem L V D
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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
    • G03C1/00—Photosensitive materials
    • G03C1/52—Compositions containing diazo compounds as photosensitive substances
    • G03C1/58—Coupling substances therefor
    • 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
    • G03C1/52—Compositions containing diazo compounds as photosensitive substances
    • G03C1/54—Diazonium salts or diazo anhydrides
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S534/00—Organic compounds -- part of the class 532-570 series
    • Y10S534/02—Azo compounds containing chains of eight or more carbon atoms not provided for elsewhere in this class

Definitions

  • the invention relates to a process for the production of diazotype copies by selective exposure (i. e. exposure to light of locally differentiated intensity) of one-component diazo film layers sensitized with a para-tertiaryaminobenzene-diazo compound and suitable for development with a liquid, and subsequent development with a developer containing an azo coupling component.
  • the development referred to above can take place in the known manner by immersion in .a bath of a developer or according to the thin-layer method (the so-called semi-wet development). The latter method is in practice generally carried out mechanically.
  • These methods of development of diazotype copies are usually applied when the diazo layer is of the one-component type, i. e. does not contain any azo coupling component; the developer (diazotype developer) then contains, in addition to buffer salts, one or more azo components which have to cause the formation of the azodyestuifs.
  • diazotype printing use is preferably made of diazo compounds and azo coupling components with a fairly high coupling activity, unless it is desired to use strongly alkaline developers, which is often inadvisable.
  • diazo compounds of slightly less coupling activity in combination with a very active azo coupling component and, conversely, combine a diazo compound of more coupling activity with an azodyestuff component of less coupling activity;
  • the azodyestuffs formed should not bleed in the developer.
  • Substances which in general have sufficient coupling activity for the practical application of the thin-layer development include: p diazo diphenylamine, p-diazoethyl-benzyl-aniline, p -diazo-di-normal-butylaniline, pdiazo-ortho-chloro-diethylaniline, the p-diazo 2.5 dialkoxy-acylanilides, and many others.
  • the p-diazo-2.5- dialkoxyacyl anilides are very active, and even suitable for development at a pH in the vicinity of 7.
  • diazo compounds which in practice are preferably not used for diazotype printing with thin-layer development, in view of insufiicient coupling activity, are: p-diazo-aniline, p-diazo-monomethylaniline, p-diazo-dimethylaniline and also p-diazo-diethylaniline.
  • azo coupling-components having sufiicient coupling activity for the thin-layer development there may be mentioned: beta-naphthol, phloroglucinol, reso-rcinol, phenyl-lmethyl-3-pyrazolone-5 (very active), aceto acetic anilide; azo coupling components with insufiicient coupling activity are: phenol and 2.B-dihydroxynaphthalene- 6-sulphonic acid.
  • diazo film layer ishere used for a special type of diazo layer.
  • diazo layer is Patented May 14, 1957 also used when the diazo compound is simply spread out on the fibres of a paper surface as a dried-up coating, perhaps in the form of a very thin uneven crust or a multitude of crusts. better-in contrast with common usageto speak of a zone instead of a layer proper.
  • a diazo film layer does have the character of a true layer; in this case one may, for example, speak of thickness. It is obvious that a diazo film layer need not be equally thick throughout; it might, for example, show a relief.
  • Such a diazo film layer is formed of matereial which is to be referred to hereinafter as film-forming material.
  • the diazo film layers have to be resistant to the treatment with the thin layer of the aqueous developer.
  • such diazo film layers must not be formed of film-forming matereial which presents serious difliculties when treated with an aqueous liquid, for example merging, dissolving, becoming objectionably sticky, and the like, as is the case with layers of gum, alkyl cellulose, soft gelatine, and similar substances. They must, however, be capable of readily accepting and absorbing the thin layer of developer; otherwise they are not suited for the thin-layer development either.
  • the diazo film layer will usually be mounted on a support; in special cases it may, however, also be independent.
  • photochemical decomposition products products which are capable of acting at room temperature on aqueous solutions of diazo compounds with a pH of over 7, whereas the photochemical decomposition products of other ptertiary-aminobenzene-diazo compounds do not have this effect, or only slightly so.
  • the saidaction if it takes place at all, proceeds more rapidly according as the pH of the solution is higher; it is very clear, for example, in the pH range of 9 to 10.
  • a weakly acidic 0.004 normal solution of the diazonium compound in question is taken and exposed to light until all the diazo compound has been decomposed.
  • the liquid obtained is mixed with an equal volume of 0.004 normal p-diethylaminobenzene-diazonium chloride solution, and brought to a pH of 9.5 through addition of sodium carbonate.
  • the mixture is now left to stand for 15 minutes at 18 C., after which the quantity of p-diethylaminobenzene-diazonium compound left behind is determined.
  • the invention relates to the production of diazotype copies by selective exposure of one-component diazo film layers sensitized with a p-tertiary-aminobenzene-diazo compound and subsequent development with a developer containing an azo coupling component.
  • a diazo film layer containing a p-tertiary-aminobenzene-diazo compound the amino group of which is substituted by residues having in total at least seven carbon atoms and which upon exposure in aqueous solution forms a product that is active, the diazo film layer is exposed and developed with a diazotype developer containing an azo coupling component of the formula:
  • X represents a hydroxyl group or a carboxylic acidamide radical without an aromatic radical in the amide group.
  • the amide group may be substituted by substituents such as amino, hydroxyl, alkyl, substituted alkyl, for example hydroxyalkyl or aminoalkyl, aralkyl. Double substitution is also possible.
  • Aromatic substituents in the amide group render the azo coupling component less suitable, such compounds being only slightly soluble in the developer liquid, at all events if the latter does not contain free alkali; moreover they have a tendency of often spoiling the tone of the lighter areas of the picture and of badly penetrating into the diazo film layer.
  • the eifect obtained with this process consists in that the images thus obtained in the diazo film reproduce some half tones, specifically those in the dark areas of the image, in a richer gradation than is generally the case when other azo coupling components (for example the azo coupling components frequently used in diazotype printing with liquid development: phloroglucinol, phenyl-methylpyrazolone, resorcinol, and beta-naphthol) are used in the diazotype developer.
  • the effect obtained in the process according to the invention is also greater than with the use of para-tertiary-aminobenzene-diazo compounds the photochemical decomposition products of which are inactive in the above sense, even when the azo coupling components prescribed for the invention are used.
  • R1 and R2 are alkyl radicals having together 10, 11 or 12 C atoms, each alkyl radical containing at least 4 and at most 7 C atoms, and not more than one of the two having a side chain attached to the alpha C atom.
  • the diazo film layer is mounted on a clear film-shaped support.
  • the invention constitutes contribution to the application of diazotype printing for these purposes.
  • Particularly strong images with good gradations in the dark half tones are obtained when the diazo content of the diazo film layer is between 0.8 and 2.0 millimols per m.
  • a hydrolysed cellulose acetate is taken, but other esters, mixtures of esters or mixed esters, for example acetate-butyrates, are also very suitable.
  • Particularly good results are obtained when the film-forming material of the diazo film layer consists of a cellulose ester with an acyl content increasing from the accessible side inwards, the portion of the layer that is insoluble in boiling dry acetone being at least 3 g. and at most 15 g. per m
  • One may, however, also use other-more or less hydrophilic-materials, 'for example partially hydrolysed polyvlnyl esters, cellulose film (cellulose hydrate) mounted on a support, for the diazo film layer.
  • gelatine as film-forming material may involve some ditficulties. Gelatine is a not very reliable initial material, and one type may behave differently from another. This behaviour may also be determined by the nature of the diazo compound of the diazo-gelatine layer. I n some cases the exposure is attended with the appearance of a so-called nitrogen screen, in other cases the lightsensitivity is smaller when a given combination of gelatine and diazo compound is used, in other cases again the thin-layer development proceeds slowly, etc.
  • An azo coupling component with which particularly good results are obtained is the hydroxyethylamide of 2-hydroxy-3-naphthoic acid.
  • a borate buffer may be composed of potassium metaborate and potassium tetraborate or of potassium tetraborate and potassium hydroxide.
  • the addition of a xanthine to the diazotype developers is .to be recommended in those cases where the azo coupling component does not dissolve readily.
  • Copies with the full half tone efiect possible according to the invention naturally are not always desirable. If copies with a reduced half tone effect are desired, in the diazo film layer a portion of the para-tertiary-aminobenzene-diazo compound that forms an active product upon exposure is replaced by an equivalent amount of a diazo compound that forms a less active or inactive product, and by the selection of given quantities of the two diazo compounds the reproduction of the half tones can thus be controlled. Preferably two diazo compounds with a fairly matched coupling activity are chosen. If the diazo compound replacing the diazo compound according to the invention forms an azodyestufr" of a different tint with the azo coupling component(s) used, its presence naturally affects the gradation of the ultimate image.
  • Any desired reduction of the half tone effect can also be obtained by replacing in the developer a portion of the azo coupling component(s) according to the inven tion by equivalent amounts of azo coupling component (s) of greater coupling activity.
  • Example 1 acetic acid, averages about 20% (which corresponds to an average number of acetyl groups attached to the OH groups of about 0.7), is impregnated on the deacylated side of the cellulose acetate layer for 30 seconds with the following solution:
  • beta-hydroxynaphthoic acid-hydroxyethylamide g. thiourea 1 g. sodium salt of isopropylnaphthalene-sulphonic acid g. sodium carbonate 1000 cm. water.
  • Example 11 In Example I the p-diazo-di-n-hexylaniline is replaced by an equivalent amount of p-diazo-ethylbenzylaniline, and the development is effected, after exposure under a dia' positive, with a developer of the following composition:
  • beta-hydroxynaphthoic acid-carboxymethylamide is replaced by an equivalent amount of beta-hydroxynaphthoic acid-aminoethylarnide, practically the same result is obtained.
  • polyvinyl acetate 60 g. partially hydrolysed polyvinyl acetate (Elv-anol 2.0- of Dupont, 47% hydrolysed, corresponding to a polyvinyl acetate content of 67%) 12 g. sodium salt of naphthalene-1.3.6-trisulphonic acid 5 g. Zinc chloride double salt of p-diazo-di-n-hexylaniline 650 cm. ethyl alcohol of 96% 350 cm. water,
  • the diazo-polyvinyl acetate layer of 3 g. per m? thus formed contains about 0.8 millimol of diazo compound per m.
  • Example IV Baryta-coated paper of 170 g. per m? with a dull surface is dipped with its baryta-coated side in a solution of 15% polyvinyl acetate (with a softening point of about 130 C. and a molecular weight of about 60,000 according to osmotic determination) in methyl alcohol, and dried. Thus a hydrophobic layer of a thickness of about 5, is formed on the baryta-coated surface. It serves to prevent the penetration into the baryta layer of the diazo solution to be applied subsequently. On to this layer there are new cast about cm. per m. of a (colloidal) solution of 40 C. of:
  • beta-hydroxynaphthoic acid-monoethanolamide 3 g. sodium salt of isopropylnaphthalene-sulphonic acid 3 g. sodium salt of the niono-ethyl-Z-hexyl-ester of sulphuric acid 1 g. potassium salt of hydroquinone-sulphonic acid 70 g. potassium tetraborate-pentahydrate 20 g. potassium carbonate 1000 cm. water A violet image with good reproduction of the half tones of the original is obtained.
  • Example V On to a cellulose acetate film of 140 g. per m? there is applied, through immersion at 30 C., a diazo film layer of the following composition:
  • gelatine J05 of Hasselt Vilvorde
  • zinc chloride double salt of p-diazo-di-n-hexyl aniline 0.2 g. tartaric acid 1000 cm. water.
  • the film layer which after drying has a thickness of about contains about 1 millimol of diazo compound per m.
  • the film has a relatively low light-sensitivity. After exposure under a cinematographic film positive, 10 g. per 111. of the developer of Example III is applied on it. A positive cinematographic copy with good reproduction of the half tones is obtained.
  • Example VI The diazo film layer of Example I is developed, after exposure under a diapositive, by the application of 9 g. per m with a solution consisting of:
  • Example VII Paper with a deacylated cellulose acetate layer as described in Example I is impregnated on the deacylated side of the cellulose acetate layer during 30 seconds with the following solution:
  • beta-hydroxynaphthoic acid-hydroxyethylamide 10 g. caffeine g. thiourea 1 g. sodium salt of isopropylnaphthalene-sulphonic acid 30 g. sodium carbonate 1000 cm. water. i
  • Example VIII Paper is treated and sensitized according to Example I.
  • Example I After exposure under a diapositive the development is efiected in the manner of Example I with a developer of the following composition:
  • a bluish-black image is obtained, with a gradation that is less soft than would have been obtained, if the phloroglucinol had been omitted from the developer.
  • a process for the production of diazotype copies which comprises selectively exposing to light a one-component diazo film layer, the film-forming material of said film layer consisting of an at least partially hydrolyzed cellulose ester wherein the average number of acyl groups attached to OH groups is from 0 to 1.5 and containing a light-sensitive p-tertiary-aminobenzene diazo compound of which the amino group is substituted by hydrocarbon residues containing in total at least seven carbon atoms and which yields an active photochemical decomposition product in the sense that a quantity of the solution obtained upon totally decomposing by light all of said compound contained in a weakly acid 0.004 11 aqueous solution of said compound, when mixed with an equal quantity of a 0.004 11 aqueous solution of p-diethylamino benzene diazonium chloride, and allowed to stand at 18?
  • X is a radical selected from the group consisting of a hydroxyl and a carboxylic acid amide radical containing no aromatic radical attached to the amide nitrogen atom, whereby the aforesaid reaction between said diazo compound and its photochemical decomposition product is brought about at said certain areas of said layer and said azo coupling component couples with the remaining part of said diazo compound.
  • a process for the production of diazotype copies which comprises selectively exposing to light a one-component diazo film layer, the film-forming material of said film layer consisting of an at least partially hydrolyzed cellulose ester, the acyl content of said material increasing progressively from the accessible side of said diazo film layer toward the interior thereof, said diazo film layer comprising from 3 to 15 grams of hydrolyzed matter insoluble in boiling dry acetone per square meter of said layer, and containing a light-sensitive p-tertiary-aminobenzene diazo compound of which the amino group is substituted by hydrocarbon residues containing in total at least seven carbon atoms and which yields an active photochemical decomposition product in the sense that a quantity of the solution obtained upon totally decomposing by light all of said compound contained in a weakly acid 0.004 11 aqueous solution of said compound, when mixed with an equal quantity of a 0.004 11 aqueous solution of p-diethylamino benzene diazonium chloride

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
  • Exposure Of Semiconductors, Excluding Electron Or Ion Beam Exposure (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US308938A 1951-09-19 1952-09-10 Process for the production of diazotype copies Expired - Lifetime US2792303A (en)

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US (1) US2792303A (en, 2012)
BE (1) BE513965A (en, 2012)
CH (1) CH311250A (en, 2012)
DE (1) DE934032C (en, 2012)
ES (1) ES205401A1 (en, 2012)
FR (1) FR1063444A (en, 2012)
GB (1) GB709359A (en, 2012)
NL (2) NL76744C (en, 2012)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3028240A (en) * 1958-01-18 1962-04-03 Keuffel & Esser Co Light sensitive diazotype materials
US3169869A (en) * 1958-06-04 1965-02-16 Grinten Chem L V D Diazotype material
US3228768A (en) * 1960-12-13 1966-01-11 Gen Aniline & Film Corp Process of diffusion printing and a structure for use therein
US3343960A (en) * 1963-09-14 1967-09-26 Keuff & Esser Company Coupling components for lightsensitive diazo coatings
US3365293A (en) * 1963-06-06 1968-01-23 Geigy Ag J R Photographic diazotype films comprising fluorescent ultraviolet absorbers
US3404005A (en) * 1963-10-01 1968-10-01 Ind Dyestuff Company Diazo light-sensitive composition and element
US3506445A (en) * 1964-12-09 1970-04-14 Bexford Ltd Synthetic film materials
US3836369A (en) * 1972-09-05 1974-09-17 Du Pont Diazo photosensitive composition
US4043816A (en) * 1972-05-26 1977-08-23 Oce-Van Der Grinten N.V. Photographic process for making diazotype copies utilizing small quantity of liquid developer

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3300471A (en) * 1964-01-02 1967-01-24 Universal Oil Prod Co p-(nu-cyanoalkyl-nu-hydrocarbylamino)-benzenediazonium chlorides

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB337868A (en) * 1929-08-24 1930-11-13 Humphrey Desmond Murray Improvements in and relating to the manufacture of sensitized bases for photographic purposes
US2037542A (en) * 1933-02-18 1936-04-14 Kalle & Co Ag Light sensitive materials containing light sensitive diazo compounds
US2233038A (en) * 1938-11-17 1941-02-25 Kalle & Co Ag Diazotype process
US2241104A (en) * 1939-01-19 1941-05-06 Naamlooze Vennootschap Chemisc Process and apparatus for the treatment of photographic coatings
US2465760A (en) * 1947-07-02 1949-03-29 Gen Anlline & Film Corp Diazotype materials derived from aryl diazo sulfones
US2528460A (en) * 1946-10-12 1950-10-31 Gen Aniline & Film Corp Diazotype compositions containing ethylene oxide derivatives of amino diazos
US2541178A (en) * 1945-08-18 1951-02-13 Gen Aniline & Film Corp Photographic process for dyeing of textile materials
US2542716A (en) * 1945-07-16 1951-02-20 Gen Aniline & Film Corp Multicolor diazotype layers
US2616803A (en) * 1948-03-11 1952-11-04 Leonard E Ravich Diazotype dyeing and printing of web or sheet material
US2617727A (en) * 1946-03-08 1952-11-11 Gen Aniline & Film Corp Alginate sized diazotype sensitized material
US2672418A (en) * 1950-01-17 1954-03-16 Keuffel & Esser Co Light-sensitive diazotype material

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB337868A (en) * 1929-08-24 1930-11-13 Humphrey Desmond Murray Improvements in and relating to the manufacture of sensitized bases for photographic purposes
US2037542A (en) * 1933-02-18 1936-04-14 Kalle & Co Ag Light sensitive materials containing light sensitive diazo compounds
US2233038A (en) * 1938-11-17 1941-02-25 Kalle & Co Ag Diazotype process
US2241104A (en) * 1939-01-19 1941-05-06 Naamlooze Vennootschap Chemisc Process and apparatus for the treatment of photographic coatings
US2542716A (en) * 1945-07-16 1951-02-20 Gen Aniline & Film Corp Multicolor diazotype layers
US2541178A (en) * 1945-08-18 1951-02-13 Gen Aniline & Film Corp Photographic process for dyeing of textile materials
US2617727A (en) * 1946-03-08 1952-11-11 Gen Aniline & Film Corp Alginate sized diazotype sensitized material
US2528460A (en) * 1946-10-12 1950-10-31 Gen Aniline & Film Corp Diazotype compositions containing ethylene oxide derivatives of amino diazos
US2465760A (en) * 1947-07-02 1949-03-29 Gen Anlline & Film Corp Diazotype materials derived from aryl diazo sulfones
US2616803A (en) * 1948-03-11 1952-11-04 Leonard E Ravich Diazotype dyeing and printing of web or sheet material
US2672418A (en) * 1950-01-17 1954-03-16 Keuffel & Esser Co Light-sensitive diazotype material

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3028240A (en) * 1958-01-18 1962-04-03 Keuffel & Esser Co Light sensitive diazotype materials
US3169869A (en) * 1958-06-04 1965-02-16 Grinten Chem L V D Diazotype material
US3228768A (en) * 1960-12-13 1966-01-11 Gen Aniline & Film Corp Process of diffusion printing and a structure for use therein
US3365293A (en) * 1963-06-06 1968-01-23 Geigy Ag J R Photographic diazotype films comprising fluorescent ultraviolet absorbers
US3343960A (en) * 1963-09-14 1967-09-26 Keuff & Esser Company Coupling components for lightsensitive diazo coatings
US3404005A (en) * 1963-10-01 1968-10-01 Ind Dyestuff Company Diazo light-sensitive composition and element
US3506445A (en) * 1964-12-09 1970-04-14 Bexford Ltd Synthetic film materials
US4043816A (en) * 1972-05-26 1977-08-23 Oce-Van Der Grinten N.V. Photographic process for making diazotype copies utilizing small quantity of liquid developer
US3836369A (en) * 1972-09-05 1974-09-17 Du Pont Diazo photosensitive composition

Also Published As

Publication number Publication date
ES205401A1 (es) 1952-11-01
DE934032C (de) 1955-10-06
BE513965A (en, 2012)
GB709359A (en) 1954-05-19
CH311250A (de) 1955-11-30
FR1063444A (fr) 1954-05-03
NL76744C (en, 2012)
NL164079B (nl)

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