US3437481A - Resin compositions - Google Patents

Resin compositions Download PDF

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Publication number
US3437481A
US3437481A US432882A US3437481DA US3437481A US 3437481 A US3437481 A US 3437481A US 432882 A US432882 A US 432882A US 3437481D A US3437481D A US 3437481DA US 3437481 A US3437481 A US 3437481A
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United States
Prior art keywords
acid
resin
vinyl
photoconductive
blend
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Expired - Lifetime
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US432882A
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English (en)
Inventor
Richard B Graver
Walter A Wallman
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Ashland LLC
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Ashland Oil Inc
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Classifications

    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
    • G03G5/0528—Macromolecular bonding materials
    • G03G5/0592—Macromolecular compounds characterised by their structure or by their chemical properties, e.g. block polymers, reticulated polymers, molecular weight, acidity
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
    • C08L67/08—Polyesters modified with higher fatty oils or their acids, or with resins or resin acids
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D167/00—Coating compositions based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Coating compositions based on derivatives of such polymers
    • C09D167/08—Polyesters modified with higher fatty oils or their acids, or with natural resins or resin acids
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
    • G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
    • G03G5/02—Charge-receiving layers
    • G03G5/04—Photoconductive layers; Charge-generation layers or charge-transporting layers; Additives therefor; Binders therefor
    • G03G5/05—Organic bonding materials; Methods for coating a substrate with a photoconductive layer; Inert supplements for use in photoconductive layers
    • G03G5/0528—Macromolecular bonding materials
    • G03G5/0557—Macromolecular bonding materials obtained otherwise than by reactions only involving carbon-to-carbon unsatured bonds
    • G03G5/056—Polyesters

Definitions

  • the present invention relates to novel resin compositions and, more particularly, to resin compositions which are useful in the electro-photographic art.
  • Direct electrostatic processes employ a substrate, normally paper, containing a coating of a p'hotoconductor, such as zinc oxide, uniformly dispersed in a binder.
  • a substrate normally paper
  • a coating of a p'hotoconductor such as zinc oxide
  • Direct electrostatic processes are described in detail in US. Patent 3,052,539 and US. Patent 3,121,006.
  • the Zinc oxide coated paper is first made sensitive to light by giving it a blanket negative electrostatic charge in the substantial absence of any ultra-violet or visible radiation.
  • One convenient means of giving the zinc oxide layer on electrostatic negative charge is by means of ion transfer from a corona discharge.
  • the zinc oxide photoconductive layer can then be exposed to a photographic image in the usual manner, portions of the zinc oxide or other photoconductor which receive light or ultra-violet radiation losing wholly, or in part (depending upon extent of exposure), the negative electrostatic charge, while the unexposed portions of the photoconductive layer retain their negative electrostatic charge.
  • the resulting latent image can then be developed by means of a pigmented powder which has a charge opposite to the negative charge of the unexposed areas of the photoconductive layer.
  • the pigmented powder is thus firmly attached or attracted to the negatively charged areas.
  • the pigmented resin powder can then be affixed to the photoconductive layer by simply melting the resinous vehicle at a temperature below the charting temperature of the paper so that the resinous powder becomes fused to the surface of the original photoconductive layer.
  • a particularly useful means of developing the latent electrophotographic image comprises use of a magnetic brush.
  • This magnetic brush development makes use of a ferromagnetic powder such as iron filings,
  • the resulting mixture can then be picked up by a magnet on which the iron particles or other ferromagnetic powder particles arrange themselves in the conventional pattern so that the long chains of filings resemble an ordinary brush.
  • the electrostatic attraction between the charged pigmented resin particles and the oppositely charged image areas in the photoconductive material is greater than the attraction between these particles and the ferromagnetic powder, so that the pigmented resin is deposited on the surface of the photoconductive material, roughly in proportion to the residual charge on the surface of the photoconductive coating.
  • Other methods of developing the latent image include the use of pigment dispersions in organic solvents and resin solutions.
  • the resin employed in combination with the photoconductor to form the photoconductive coating is of extreme importance in the success of the process.
  • the resin must be an extremely good insulator which prevents decay of the electrostatic charge before the photoconductive coating is exposed to the image.
  • the resin In order to have the photoconductor accept a maximum electrostatic charge, it is necessary that as many of the individual photoconductor particles are separately encapsulated by the resin.
  • the resin must therefore be capable of properly wetting the p-hotoconductor and keep it in place in the photoconductive matrix.
  • the resin should not interfere in the discharge of the electrostatic charge when the coating is exposed to the image to be copied.
  • the binder resin employed should cause good adhesion to the support.
  • the resin should not exhibit color or decompose on aging.
  • the resin should bond readily to the pigmented developer and give rise to good printing quality.
  • novel compositions of the present invention comprise blends of (a) alkyd resins which are soluble in hydrocarbon solvents and have acid numbers of less than 10 and hydroxyl numbers of less than with (b) 5 to 40% by weight of the composition of a polymer of a vinyl monomer having the general formula R2 where R is hydrogen, chlorine, or a methyl group, and R is selected from the group consisting of phenyl, chlorine, fluorine,
  • R is a lower alkyl group of 1 to 4 carbon atoms and preferably methyl or ethyl.
  • the blend exhibits synergistically improved insulating and electrical properties as compared to the components of the blend.
  • acid number is meant the milliequivalents of KOH required to neutralize the acid in one gram of polymer and by hydroxyl number is meant the milliequivalents of KOl-I required to saponify the hydroxyl groups in one gram of resin on esterification with an acid anhydride. The details of these standard tests are known in the art.
  • alkyd resins have heretofore been employed as binders for photoconductors, such compositions have shown serious deficiencies with respect to their ability to retain an electrostatic charge in the absence of light and the degree to which such compositions can be charged. This deficiency of alkyd resins is in part ascribed to the wide molecular weight distribution of hydrocarbon soluble alkyd resins, and their high acid and hydroxyl numbers.
  • the alkyd resins employed in the compositions of the present invention are preferably prepared by reacting the alkyd resin components to form an alkyd resin if a high acid number which is soluble, refluxing a solution of the acidic alkyd resin in a hydrocarbon solvent having a boiling point in the range of about 150 to about 420 F., the solvent being employed in a concentration of 30 to 70% of the total mixture, while removing any water of reaction and continuing the reaction until the desired acid number below is obtained.
  • the alkyd resins are of the fast or air drying type which contain generally from about 25 to 70% by weight of the resin of a monobasic acid selected from the class consisting of aliphatic, alicyclic, and aromatic acids having from 4 to 26 carbon atoms, which can also be defined by the general formula RCOOH wherein R is a hydrocarbyl radical of 3 to 25 carbon atoms, about to about 60% by weight of the total composition of a polybasic acid containing two or more carboxylic acid groups, such as phthalic anhydride, phthalic acid, isophthalic acid, terephthalic acid, maleic anhydride, fumaric acid, adipic acid, and succinic acid, and from about 15 to 45% by weight of a polyhydric alcohol containing two or more hydroxyl groups such as trimethylol ethane, trimethylol propane, glycerol, pentaerythritol, sorbitol, ethylene glycol, propylene glycol, neopent
  • the preferred monobasic acids employed in the alkyd resin compositions are the unsaturated fatty acids, having from 12 to 24 carbon atoms, such as are derived from soya, linseed, safilower, tung, cocoanut, walnut, rape seed, perilla, sunflower, castor, cottonseed, tuna, sardine, menhaden, and tallow oil.
  • Other monobasic acids which can be employed in the alkyd resins either by themselves or in combination with the fatty acids include benzoic acid, p-tertbutyl benzoic acid, rosin acids, cyclohexane carboxylic acid, abietic acid, pelargonic acid and the like.
  • the saturated acids can be used to control the viscosity of the resin and increase its thermoplasticity.
  • saturated monobasic acids are employed in a concentration not exceeding 50% of the total concentration of monobasic acids. It is to be understood, however, that the composition of the alkyd resin employed in the present invention is not critical as long as the resin is soluble in a hydrocarbon solvent and has the required acid and hydroxyl number. The preparation of alkyd resins meeting these requirements is more fully disclosed in copending application SN. 1249 filed J an. 8, 1960* now abandoned.
  • the second component of the blends of the present invention comprises a polymer of a vinyl monomer containing substituents of the type defined.
  • Particularly suitable polymers are the acrylic ester polymers and copolymers, vinyl halide polymers and c0- polymers, polystyrene, poly(alpha-methylstyrene) styrene acrylate copolymers and vinyl ester polymers.
  • the acrylic esters of these polymers comprise in general esters of acrylic and methacrylic acid in which the ester radical contains from one to four carbon atoms and more particularly such acrylic esters as methyl methacrylate, ethyl acrylate, n-butyl acrylate, and isobutyl acrylate.
  • the vinyl halide polymers employed are principally poymers of vinyl chloride and vinylidene chloride.
  • the vinyl ester polymers employed are normally vinyl acetate polymers although polymers of vinyl esters having from four to six carbon atoms are operable. These vinyl polymers may be homopolymers or may be copolymers of each other and of other ethylenically unsaturated monomers. If copolymers of the described vinyl monomers are employed, the described vinyl monomers must constitute the major component of the vinyl resin, i.e., the concentration of the vinyl monomers or combination of the vinyl monomers must be greater than 50%.
  • the concentration of the acid or alcohol in the vinyl resin must be such that the total acid concentration and hydroxyl concentration in the blend does not exceed the required acid and hydroxyl limitations.
  • the concentration of the acid or alcohol comonomer should not be such that, when it is employed in the blend with the alkyd resin, the acid number of the blend exceeds ten or the hydroxyl number of the blend exceeds 100. Since, however, the vinyl resin can be employed in a concentration of 5 to 40% it will be apparent that the composition of the vinyl polymer can be substantially varied. Vinyl polymers which do not contain either acid or hydroxyl groups are, however, preferred blending agents for the binder compositions of the present invention.
  • the vinyl polymer is employed in a concentration of 5 to 40% and preferably in a concentration of 7 to 15% by weight of the total composition. More than one vinyl polymer can be employed. It will be recognized that in view of the properties required of good binders, the concentration of the vinyl polymer in the blend should be such that a compatible blend with the alkyd resin is formed, and hence the upper concentration of a particular vinyl polymer component in a particular blend may be limited by its compatibility with the alkyl resin.
  • the photoconductive compositions of the present composition are prepared using methods heretofore developed, such as described in US. Patents 3,128,179 and 3,121,006.
  • the vinyl polymer is added to the alkyl resin solution to which is then added the photoconductor and such other additives as photosensitive dyes and similar materials.
  • the ratio of the photoconductor, such as zinc oxide, to the binder can be varied over a wide range.
  • Sufiicient binder should be employed to insulate each of the photoconductive particles from the surrounding particles in the composition.
  • the most useful or optimum quantity of zinc oxide to resin binder for a particular photoconductive composition can be readily determined by making a series of test coatings wherein the quantity and relative amounts of the photoconductor to the binder resin are employed. In general the ranges will be from 10 to 90% by weight of the total composition.
  • Example 1 An alkyd resin was prepared by employing 725 parts of soya fatty acid, 332 parts of glycerol, 196 parts of pentaerythritol, and 932 parts of phthalic anhydride. The components were admixed and cooked in the conventional manner until an acid value of about 40-50 was reached, at which time the reaction mixture was diluted with 4,000 parts of xylene, and the reaction continued at reflux until a resin solution was obtained having an acid number of 6-10. The acid number was determined in accordance with the standard procedure and constitutes the number of milliequivalents of potassium hydroxide which are required to neutralize the acid in one gram of resin. At a non-volatile solids content of 50% this resin was found to have a viscosity of 15 to 25 stokes.
  • the coating was found to accept a maximum voltage of 825 volts, showed a 20 second dark decay voltage of 760 volts, a one second exposure voltage of 410 volts, a residual voltage of 75 volts after an exposure time of 1.3 seconds.
  • the print quality of the coating was extremely good. Particularly unexpected was the improvement in maximum voltage and residual voltage since the acrylate copolymer by itself has a maximum voltage of 400 to 500 volts while the alkyl resin by itself has a maximum voltage of 5 to 600 volts.
  • Example 2 The procedure of Example 1 was repeated employing instead of the acrylate copolymer a vinyl acetate copolymer commercially available as VAGD. The same electrical properties as obtained in Example 1 were obtained with this resin blend.
  • Example 3 The procedure of Example 1 was repeated using instead of the acrylate copolymer a copolymer of vinylidene chloride and vinyl chloride. Substantially the same electrical properties were obtained on the resulting coating as in Example 1.
  • Example 4 An alkyd resin was prepared by employing 638 parts soya fatty acid, 45.4 parts of p-tert-butyl benzoic acid, 299 parts of trimethylol propane and 635 parts of phthalic anhydride. The components were admixed and refluxed with 5% xylene at 400 F. until an acid number of 25 to 30 was attained. Xylene was then added until a non-volatile content of 50% was reached and the reflux was continued at 465 to 480 F. until a resin solution was obtained in which the resin had an acid number of 6 to 10, a hydroxyl number of 70 to 80, and a viscosity of 5 to 10 stokes at a non-volatile solids content of 50%. Photoconductive compositions were prepared following the procedure of Example 1. The electrical properties of coatings prepared from the photoconductive composition were the same as those shown in Example 1.
  • a photoconductive composition comprising a blend of (a) an alkyd resin having an acid number of less than 10 and a hydroxyl number of less than 100, said resin being soluble in hydrocarbon solvents, and composed of (1) about 25 to 70% by weight of monobasic acid of 4 to 26 carbon atoms, (2) about 15 to 60% by weight of a polycarboxylic acid, and (3) about 15 to 45 by weight of a polyhydric alcohol having more than two hydroxyl groups; and (b) from 5 to 40% by weight of the blend of a polymer of a vinyl monomer having the general formula where R is selected from the group consisting of hydrogen, chlorine, and methyl radicals, and R is selected from the group consisting of phenyl, chlorine, fluorine,
  • R is a lower alkyl group of 1 to 4 carbon atoms
  • said polymer consisting essentially of said monomer, said blend having an acid number of less than 10 and a hydroxyl number of less than 100 and containing uniformly dispersed therein from 10 to by weight of the photoconductive composition of a photoco'nductor.
  • polyhydric alcohol is selected from the class consisting of pentaerythritol, trimethylol ethane, triethylol propane, and glycerol.
  • a photoconductive composition comprising a blend of (a) an alkyd resin having an acid number of less than 10, a hydroxyl number of less than 100, said resin being soluble in hydrocarbon solvents and composed of (1) about 25 to 70% by Weight of an unsaturated fatty acid having from 12 to 24 carbon atoms, (2) about 15 to 60% by weight of a polycarboxylic acid selected from the class consisting of phthalic acid, isophthalic acid, adipic acid, fumaric acid, maleic acid, and anhydrides thereof, and (3) about 15 to 45 by weight of a polyhydric alcohol selected from the class consisting of glycerol, trimethylol ethane, triethylol propane, and pentaerythritol and (b) from to 40% by weight of the blend of a polymer of a vinyl monomer having the general formula where R is selected from the group consisting of hydrogen, chlorine, and methyl radicals, and R is selected from the group consisting of phenyl, chlorine, fluorine,
  • R is a lower alkyl group of 1 to 4 carbon atoms
  • said polymer consisting essentially of said vinyl monomer, said blend having an acid number of less than and a hydroxyl number of less than 100 and containing uniformly dispersed therein from 10 to 90% by weight of the photoconductive composition of a photoconductor.
  • the photoconductive composition of claim 7 wherein the monomer of the vinyl polymer is n-butyl acrylate, n-butyl methacrylate, or methyl methacrylate.

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  • Chemical & Material Sciences (AREA)
  • Physics & Mathematics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Organic Chemistry (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Photoreceptors In Electrophotography (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Polyesters Or Polycarbonates (AREA)
US432882A 1965-02-15 1965-02-15 Resin compositions Expired - Lifetime US3437481A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US43288265A 1965-02-15 1965-02-15

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US3437481A true US3437481A (en) 1969-04-08

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US432882A Expired - Lifetime US3437481A (en) 1965-02-15 1965-02-15 Resin compositions

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US (1) US3437481A (enrdf_load_stackoverflow)
JP (1) JPS497496B1 (enrdf_load_stackoverflow)
BE (1) BE675793A (enrdf_load_stackoverflow)
DE (1) DE1270282B (enrdf_load_stackoverflow)
FR (1) FR1466190A (enrdf_load_stackoverflow)
GB (1) GB1141282A (enrdf_load_stackoverflow)
NL (1) NL6601858A (enrdf_load_stackoverflow)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3519421A (en) * 1967-09-26 1970-07-07 Gaf Corp Electrophotographic recording material
US3709684A (en) * 1970-12-11 1973-01-09 Ica America Inc Photoconductive compositions and elements employing polyoxyalkylene bisphenol a fumarates as binders
US4030921A (en) * 1974-11-19 1977-06-21 Konishiroku Photo Industry Co., Ltd. Electrophotographic photosensitive material
US4427754A (en) 1981-03-10 1984-01-24 Mitsubishi Paper Mills, Ltd. Electrophotographic lithographic printing plate
US5320923A (en) * 1993-01-28 1994-06-14 Hewlett-Packard Company Reusable, positive-charging organic photoconductor containing phthalocyanine pigment, hydroxy binder and silicon stabilizer

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS52105825A (en) * 1976-03-03 1977-09-05 Konishiroku Photo Ind Co Ltd Electronic photographic photosensitive material
JPH0690546B2 (ja) * 1986-03-14 1994-11-14 富士写真フイルム株式会社 電子写真式平版印刷用原版
JPH0750338B2 (ja) * 1986-05-02 1995-05-31 富士写真フイルム株式会社 電子写真式平版印刷用原版

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2767151A (en) * 1952-08-29 1956-10-16 Armstrong Cork Co Copolymers of aryl olefins and alpha beta ethylenically unsaturated carboxylic acid esters of oxidized nonfrosting siccative oils
US3080331A (en) * 1957-11-12 1963-03-05 Schenectady Chemical Insulating varnish including an oilmodified alkyd resin and an oil soluble phenol-formaldehyde resin
US3121006A (en) * 1957-06-26 1964-02-11 Xerox Corp Photo-active member for xerography
US3149087A (en) * 1961-11-08 1964-09-15 Monsanto Co Plasticized halogen-containing resins
US3281498A (en) * 1960-05-13 1966-10-25 Minnesota Mining & Mfg Vinyl plastisols having polycarboxyl containing polyesters as plasticizers

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL295738A (enrdf_load_stackoverflow) * 1962-07-27 1900-01-01

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2767151A (en) * 1952-08-29 1956-10-16 Armstrong Cork Co Copolymers of aryl olefins and alpha beta ethylenically unsaturated carboxylic acid esters of oxidized nonfrosting siccative oils
US3121006A (en) * 1957-06-26 1964-02-11 Xerox Corp Photo-active member for xerography
US3080331A (en) * 1957-11-12 1963-03-05 Schenectady Chemical Insulating varnish including an oilmodified alkyd resin and an oil soluble phenol-formaldehyde resin
US3281498A (en) * 1960-05-13 1966-10-25 Minnesota Mining & Mfg Vinyl plastisols having polycarboxyl containing polyesters as plasticizers
US3149087A (en) * 1961-11-08 1964-09-15 Monsanto Co Plasticized halogen-containing resins

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3519421A (en) * 1967-09-26 1970-07-07 Gaf Corp Electrophotographic recording material
US3709684A (en) * 1970-12-11 1973-01-09 Ica America Inc Photoconductive compositions and elements employing polyoxyalkylene bisphenol a fumarates as binders
US4030921A (en) * 1974-11-19 1977-06-21 Konishiroku Photo Industry Co., Ltd. Electrophotographic photosensitive material
US4427754A (en) 1981-03-10 1984-01-24 Mitsubishi Paper Mills, Ltd. Electrophotographic lithographic printing plate
US5320923A (en) * 1993-01-28 1994-06-14 Hewlett-Packard Company Reusable, positive-charging organic photoconductor containing phthalocyanine pigment, hydroxy binder and silicon stabilizer

Also Published As

Publication number Publication date
NL6601858A (enrdf_load_stackoverflow) 1966-08-16
FR1466190A (fr) 1967-01-13
GB1141282A (en) 1969-01-29
BE675793A (enrdf_load_stackoverflow) 1966-08-01
DE1270282B (de) 1968-06-12
JPS497496B1 (enrdf_load_stackoverflow) 1974-02-20

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