US3890156A - Desensitizer composition - Google Patents

Desensitizer composition Download PDF

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Publication number
US3890156A
US3890156A US367061A US36706173A US3890156A US 3890156 A US3890156 A US 3890156A US 367061 A US367061 A US 367061A US 36706173 A US36706173 A US 36706173A US 3890156 A US3890156 A US 3890156A
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Prior art keywords
diaza
desensitizer
composition
bicyclo
acid
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Expired - Lifetime
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US367061A
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English (en)
Inventor
Hiroharu Matsukawa
Akio Miyamoto
Akio Watanabe
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Fujifilm Holdings Corp
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Fuji Photo Film Co Ltd
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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M5/00—Duplicating or marking methods; Sheet materials for use therein
    • B41M5/124—Duplicating or marking methods; Sheet materials for use therein using pressure to make a masked colour visible, e.g. to make a coloured support visible, to create an opaque or transparent pattern, or to form colour by uniting colour-forming components
    • B41M5/128—Desensitisers; Compositions for fault correction, detection or identification of the layers

Definitions

  • the present invention relates to a desensitizer composition, more precisely, to a desensitizer composition which reduces or destroys the function of a developer to color a colorless color former.
  • 29546/71 tertiary amines derived from a chemical bonding of a monoalkylarnine, aralkylamine or ethanolamine and ethylene oxide
  • Japanese Patent Publication No. 3569/71 precondensation products of urea resins
  • secondary alkylamines such as didodecylamine; tertiary alkylamines such as triethylamine; primary arylamines such as aniline; aralkylamines such as benzylamine; polyhydroxyl compounds such as polyethylene glycol and glycerin).
  • these desensitizers either have an insufficient desensitizing effect or, if the effect is sufficient, it is necessary to use a large amount of the agents in order to attain a practical effect.
  • these agents have several faults.
  • Some desensitizers color desensitized portions even if a large amount is used, and other desensitizers cause the same phenomenon unless a large amount thereof is used. In particular, these defects are apt to become great with improvements in color formers and developers.
  • color formers containing a fluoran nucleus are especially difficult to desensitize, as compared with Crystal violet lactone, etc.
  • these desensitizers are almost ineffective for developers such as phenol resins or metal salts of aromatic carboxylic acids. Therefore, limits on the few advantageous properties of these developers exist, e.g., the developed color image obtained using the same does not disappear in the presence of water.
  • Another defect of conventional desensitizers is that non-desensitized areas of a developer gradually color with the lapse of time (that is, fog occurs) when a color former is brought into contact with the desensitized developer using an encapsulation system.
  • One object of the present invention is to provide a desensitizer composition having a strong desensitizing effect.
  • Another object of the present invention is to provide a desensitizer composition which has excellent coatability and which can be used for aqueous and oily materials.
  • Still another object of the present invention is to provide a desensitizer composition which does not harmfully affect a color former or a developer or a system containing both a color former and developer.
  • the diaza-bicycloalkene used are those represented by the following formula, and the salts thereof are fatty acid salts thereof or salts thereof with phenols:
  • n is an integer of 2-1 I
  • each ring can be substituted by one or more alkyl groups of 1-4 carbon atoms, where all positions of the ring can be so substituted.
  • the desensitizer of the invention is a substance or compound capable of preventing the reaction of color formers and color developers which are coated on the same or different supports. More precisely, the desensitizer is a substance or compound capable of inactivating the color-formation property of color developers coating it on a layer thereof.
  • acids used for the formation of salts of the diaza-bicycloalkenes fatty acid or phenol type compound can be used.
  • the acids are, for example, saturated fatty acids such as acetic acid, propionic acid, butyric acid, caproic acid, caprylic acid, undecylic acid, lauric acid, tridecylic acid, myristic acid, palmitic acid, heptadecylic acid, stearic acid, etc.; unsaturated fatty acids such as acrylic acid, crotonic acid, undecylenic acid, oleic acid, sorbic acid, linoleic acid, linolenic acid, propiolic acid, etc; isoalkylfatty acids such as 2- ethylhexanoic acid, etc.; hydroxy fatty acids, such as lactic acid, glycolic acid, ricinoleic acid, hydroxystearic acid, etc.
  • saturated fatty acids such as acetic acid, propionic acid, butyric acid, caproic acid, caprylic acid, undecylic acid, lauric acid, tridecylic acid, my
  • phenols are, phenol, substituted phenols (such as cresol, xylenol, ethylphenol, propylphenol, butylphenol, nonylphenol, dodecylphenol, chlorophenol, cyclohexylphenol, phenylphenol, trimethylphenol, tetramethylphenol, naphthol, etc.), polyhydric phenols (such as resorcin, catechol, pyrogallol, hydroquinone, phloroglucinol, dihydroxymethylbenzene, naphthalenediol, etc.), phenol carboxylic acids (such as hydroxybenzoic acids, resorcylic acids, gallic acid, etc.), phenol sulfonic acids, nitrophenols and phenols such as biphenol, bicresol, dibenzylbiphenol, methylenebiphenol, bisphenol A, etc.
  • substituted phenols such as cresol, xylenol,
  • the salts of the above mentioned diazabicycloalkenes can be prepared merely by reacting the diaza-bicycloalkenes with the selected acid.
  • the ratio of the respective reaction components can be equivalent, or excess diazabicycloalkenes can be used, or, excess-acid component can be used.
  • the formation of the salts easily proceeds at room temperature without any particular catalyst, but when solid acids are used, it is advantageous to use an inert volatile solvent such as benzene, toluene, xylene, hexane, heptane or the like.
  • Thesolvent used can easily be removed by any appropriate method after the completion of the reaction.
  • salts are colorless liquids free from any unpleasant odor, and are soluble in an aromatic type solvent as above and an alcohol, and, in addition they are easily dispersed or dissolved in water.
  • aromatic solvents and alcohols aliphatic solvents such as methanol, ethanol, propanol, butanol or arnyl alcohol
  • the solvent is not limited so long as it does not react with the reaction components and products.
  • the compounds of the present invention are effective for desensitization in small quantities, as compared with conventionaldesensitizers.
  • the present compounds display a sufficient desensitization effect in an amount of one-fifth (by weight) of conventional desensitizers.
  • the compound or compounds is/are used in an amount of more than one-fifth of conventional desensitizers, a stronger desensitization effect is attained, and the said weight value one-fifth is determined merely from economic advantages.
  • the compound of the present invention is. used in an amount less than one-fifth (weight amount) of conventional desensitizers, the effect thereof decreases with the decrease of the amount used, but it is to be noted that the compound of the present invention still displays an excellent effect over the same amount of a conventional desensitizer. On these grounds, it is apparent that the amount of the compounds of the present invention to be used is not specifically limited.
  • the amount of the desensitizer of the present invention is not especially limited. However, in commercial use certain proportions will find greater acceptability than others, and usually at least about 1 weight percent to a maximum of weight percent, based on the desensitizer composition weight, of the desensitizer ofthe present invention will be used, more preferably 5 to 30 weight percent. Generally, using from about 10 weight to 20 weight will provide excellent effects in almost cases.
  • the maximum value set above is set purely for economic reasons, and it will be appreciated by one skilled in the art that little need ex' ists to use such high-proportions of desensitizer under normally encountered conditions.
  • the desensitizer composition of the invention contains the compound of the formula and generally an inorganic solid material and a binder.
  • the inorganic solid material is used to provide a desired fluidity and whiteness to the composition, and the binder is used to carry the inorganic solid material.
  • the amount of three components can be set in a wide range according to the desired purposes.
  • the desensitizer composition of the present invention it is sufficient that at least one of the above mentioned diaza-bicycloalkene or salts thereof is contained therein as the desensitizer component, and the other components can be any conventional ones.
  • the other components are the following components which are contained in conventional desensitizer compositions: Natural or synthesic high molecular weight compounds such as ketone resins, polyamide resins, maleic acid resins, fumaric acid resins, phenol resins, epoxy resins, alkyd resins, melamine resins, urea resins, acrylic resins, nitrocellulose, methyl cellulose, cellulose butyrate acetate, butyral resins, casein, gelatin, polyvinyl alcohol, etc.
  • Natural or synthesic high molecular weight compounds such as ketone resins, polyamide resins, maleic acid resins, fumaric acid resins, phenol resins, epoxy resins, alkyd resins, melamine resins, urea resins, acrylic resins, nitrocellulose, methyl cellulose, cellulose butyrate acetate, butyral resins, casein, gelatin, polyvinyl alcohol, etc.
  • the binder can also function to prevent an ink from transferring to piled papers
  • pigments such as titanium dioxide, zinc oxide, barium sulfate, magnesium carbonate, calcium carbonate, barium carbonate, magnesium hydroxide, talc, etc. (these are to improve printability, whiteness and masking power)
  • solvents such as glycols (e.g., ethylene glycol, diethylene glycol, glycerin, polyethylene glycol, polypropylene glycol, etc.), alcohols, e.g., as heretofore recited as saltformation solvents, etc.; fats and oils such as paraffin, Japan wax, etc. (these are to improve abrasion resistance); and drying oils (such as linseed oil, tung oil, bean oil), semidrying oils (such as cotton seed oil, sesame oil, corn oil, rape oil, rice bran oil).
  • additives such as an off setting inhibitor (e.g., starch) as well as other desensitizers can optionally be incorporated in the composition of the present invention.
  • an off setting inhibitor e.g., starch
  • desensitizers can optionally be incorporated in the composition of the present invention.
  • composition of the present invention can be in any form as is commonly used in the art such as an aqueous solution, a solution in an organic solvent (e.g., alcohol solution), an aqueous dispersion, a paste or a solid. It is to be noted that the function of the composition of the present invention is not harmed in any manner due to the kind, amount or form of the other components contained therein, that is the function is present irrespective of the other additives used.
  • the only active desensitizing component required is generally the one or more diazabicycloalkene compounds or the salts thereof.
  • any other components can be freely and optionally selected and the proportion thereof freely varied in a manner known to the art.
  • the high molecular weight compound merely serves, where rough handling is anticipated, to maintain the desensitizer composition in its desired position. Where such extra strength is not needed, the high molecular weight compound can be omitted.
  • the pigments improve commercial properties as recited above. Thus, in instances where such properties are not important, the pigments can be deleted.
  • the solvents are merely for improving coatability, as are the fats and oils. Thus, where coatability is not an important factor, these components can be omitted.
  • the desensitizer composition of the present invention can easily be prepared by those skilled in the art, and can be supplied to a developer by means of various methods such as relief printing or photogravure printing, spraying, hand writing as a crayon or in the form of an eraser, or the like.
  • the developers to which the desensitizer composition of the present invention can be applied are electron acceptors, which are well known in this technical field. They are generally electron-accepting solid acids. Examples thereof are the clay minerals such as terra alba, attapulgite etc.; organic acids such as tannic acid, gallic acid, propyl gallate, etc.; acid polymers such as phenol-formaldehyde resins, phenolacetylene condensation resins, etc.; metal salts of aromatic carboxylic acids such as zinc salicylate, tin salicylate, zinc 2- hydroxynaphthoate, zinc 3,5-di-tert.butyl-salicylate, etc.; or mixtures thereof.
  • Such developers are disclosed in U.S. Pat. Nos. 2,972,547; 3,455,721; 3,427,180; 3,516,845; 3,634,121; and 3,672,935 and in U.S. Ser.
  • - ate copolymer latex a polyvinyl acetate latex, a polyvinylidene chloride latex, a polymethylmethacrylate latex, a polyethylmethacrylate latex, etc.
  • the other is a water-soluble high molecular weight compound such as starch, casein, polyvinyl alcohol, styrene-maleic anhydride copolymer, etc.
  • the color formers reacted with the developers at color forming are almost colorless organiccompounds which are electron donors, and are, for example, triazolemethane type compounds, diphenylmethane type compounds, xanthene type compounds, thiazine type compounds, spiropyran type compounds, etc. Examples these compounds are as follows:
  • Triazolemethane type compounds 3,3-bia(p-dimethylaminophenyl)-6-dimethylaminophthalide or Crystal violet lactone (hereunder referred to as CVL), 3,3-bis(p-dimethylaminophenyl)phthalide, 3-(p-dimethylaminophenyl )-3-( 1,2-dimethylindol-3- yl)phthalide, 3-(p-dimethylaminophenyl)-3-(2-methylindol-3-yl)phthalide, 3-(p-dimethylaminophenyl)-3-(2- phenylindol-3-yl)phthalide, 3,3-bis-( 1 ,2- dimethylindol-3-yl )-5 -dimethylaminophthalide, 3 ,3- bis-( l,2-dimethylindol-3-yl )-6- dimethylaminophthalide, 3 ,3-bis-( 9-ethylc
  • Xa'nthene type compounds Rhodamine-B-anilinolactam, nitroanilino)lactam, chloroanilino)lactam, 7-dimethylamino-2-methoxyfluoran, 7-diethylamino-2-methoxyfluoran, 7- diethylamino-3-methoxyfluoran, 7-diethylamino-3- chlorofiuoran, 7-diethylamino-3-chloro-2- methylfluoran, 7-diethylamino-2,3-dimethylfluoran, 7-diethylamino-(3-acetylmethylamino )fluoran, 7- diethylamino-( 3-methylamino )fluoran, 3 ,7-
  • Thiazine type compounds Benzoyl-leucomethylene leucomethylene blue, etc.
  • the color former solution may, if desired, be applied only to limited. parts of the paper to be coated, which is another embodiment.
  • the color former and the developer can be used in an manner for pressure-sensitive recording papers, heat-sensitive copying papers and the like. 7
  • any encapsulation method of the prior art can be used in the present invention.
  • the Greene et al patent cited above is merely exemplary, as this is a landmark patent in the field of complex coacervation. Any other encapsulation technique can be used without restriction. i
  • the developer sheets, color former sheets and desensitizer ink 'used in the following examples to confirm the effect of the desensitizers of the present invention were prepared as follows: (part means fpart by weight" hereinunder).
  • Coating Solution B a coating solution (Coating Solution B).
  • the thus prepared coating solution was applied to a base paper (weight: 50 g/m and dried toobtain a developer sheet (Developer Sheet B).
  • the coated solids content was 2 glm
  • Preparation of Developer Sheet C 4 parts of caustic soda were dissolved in 200 parts of water, and 25 parts of 3,5-di-tert-butyl-salicylic acid were dissolved therein while stirring.
  • Coating Solution C a 10% aqueous solution of polyvinyl alcohol (trade name: PVA-205 by Kurare Co.) were further added thereto, and the resulting mixture was milled in a ball mill for 10 hours to prepare a coating solution (Coating Solution C).
  • the thus prepared coating solution was applied to a base paper (weight: 50 g/m) and dried to form a developer sheet (Developer Sheet C), the coated solids content being 2 g/m
  • Preparation of Developer Sheet D pare a coating solution.
  • the resulting solution was applied to a base paper (weight: 50 g/rn) and dried to form.
  • a developer sheet (Developer Sheet D), the coated solids content being 2 g/m Preparation of; Color Former Sheet A 10 parts of an acid treated gelatin having an isoelectric point of 8.0 and 10 parts of gum arabic were dissolved in 60 parts of water at 40C, and 02 part of sodium alkylbenzene sulfonate was added thereto as an emulsifier, and then 50 parts of a color former oil were emulsified therein.
  • the color former oil was prepared by dissolving in an oil consisting of 4 parts of diisopropylphenyl and 1 part of kerosene, 2.5% by weight of Crystal violet lactone and 2.0% by weight of benzoyl leucomethylene blue.
  • the resulting ink was applied to each of the above mentioned developer sheets in an amount of 2 g/m 3,6-bis-methoxyfluoran and 2% by weight of benzoyl- 5 and printed as described below. leucomethylene blue, to prepare a color former oil.
  • a color former sheet g p g Test Method (Color Former Sheet B) was prepared according to the procedure of preparing Color Former Sheet A.
  • de- I I k 10 sensitizer which was optionally and freely prepared, Preparanon of Desensmzanon n and the desensitized part was put face to face with a 60 parts of desensitizer as shown in the following Tacolor former sheet, whereupon the coloring operation ble, and, as a binder, 30 parts of rosin-modified maleic was carried out under an electric charge of 600 kg/cm acid resin (trade name: Hitalac X24M, by Hitachi The desensitization effect was evaluated from the re- Chemical Industries Co.) were heated and melted to 15 flection visible density value (Vis. D), obtained by form a varnish. 10 parts of titanium dioxide were added measuring the density of the sheet with a microdensito the resulting varnish and kneaded in athree-roll mill, tometer after it was left to stand for 1 full day.
  • Desensitization effect (Vis.-D) Color former Sheet A Color Former Sheet B Ex. Desensitizer Developer Developer Developer Developer Developer Developer No. Sheet A Sheet B Sheet C Sheet D Sheet A l l,8-diazabicycl0(5,4,0) 0.01 0.01 0.01 0.01 0.01 0.01 0.01 0.01
  • compositions of the present invention are effective to desensitization about 100 times a composition not containing any desensitizer (Comparative Example 1), and about 35 times as effective as a conventional desensitizer (Comparative Example 2-6).
  • the compound of Comparative Example 3 is more effective than the other compounds, but the desensitization effect thereof varies depending upon the kind of color former used.
  • the desensitizers of the present invention are effective for desenstiz ation in any case, and further, the desensitization effect is always great irrespective of the kinds of the used color formers.
  • the present desensitizers are extremely advantageous.
  • a desensitizer composition for desensitizing a developer against coloring a colorless color former, which comprises an inorganic pigment, a resin binder and a desensilizing agent; the improvement comprising, as said agent at least about l weight percent, based on the composition weight, of an amine of the folllowing formula or a salt thereof:
  • n is an integer of 2-1 1
  • each ring can be substituted by one or more alkyl groups of l-4 carbon atoms;
  • fatty acid is selected from the group consisting of a saturated fatty acid, unsaturated fatty acid, isoalkyl fatty'acid and hydroxy fatty acid.
  • fatty acid is selected from the group consisting of acetic, propionic, butyric, caprylic, caproic, undecylic, lauric, tridecyclic, myristic, palmitic, heptadecyclic, stearic, acrylic, crotonic, undecylenic, oleic, sorbic, linoleic, linolenic, propiolic, 2-ethylhexanoic, lactic, glycolic, ricinoleic and hydroxy stearic acid.
  • phenol compound is selected from the group consisting of phenol, cresol, xylenol, ethylphenol, propylphenol, butylphenol, nonylphenol, dodecyiphenol, chlorophenol, cyclohexylphenol, phenylphenol, trimethylphenol, tetramethylphenol, napthol, resorcin, catechol, pyrogallol, hydroquinone, phloroglucinol, dihydroxymethylbenzene, napthalenediol, hydroxybenzoic acid, resorcylic acid, gallic acid, phenol sulfonic acid, nitrophenol, biphenol, bicressol, dibenzylbiphenol, methylenebiphenol and bisphenol A.
  • said electron accepting developer is selected from the group consisting of a clay mineral, an organic acid, an acid polymer, a metal salt of an aromatic carboxylic acid and a mixture thereof.
  • said electron accepting developer is selected from the group consisting of terra alba, attapulgite, tannic acid, gallic acid, propyl gallate, a phenolformalin resin, a phenol acetylene condensation resin, zinc salicylate, tin salicylate, zinc 2-hydroxynaphthoate, zinc 3,5-di-tert-butyl-salicylate and mixture thereof.
  • the desensitizer composition as claimed in claim 1 in combination with a color former which is a colorless, electron donating organic compound.
  • the desensitizer composition as claimed in claim 1 in combination with an electron accepting developer and a color former which is a colorless, electron donating organic compound.
  • the desensitizer composition as claimed in claim l which further comprises a drying oil selected from the group consisting of linseed oil, tung oil, and bean oil.
  • a method for desensitizing a developer which developer produces a colored reaction product upon reaction with a colorless color former, which comprises applying thereto a desensitizer composition comprising an inorganic pigment, a resin binder and a desensitizing agent; the improvement comprising, as said agent, at least about 1 weight percent, based on the composition weight, of an amine of the following formula or a salt thereof:

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US367061A 1972-06-03 1973-06-04 Desensitizer composition Expired - Lifetime US3890156A (en)

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JP5547072A JPS5426926B2 (enrdf_load_stackoverflow) 1972-06-03 1972-06-03

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JP (1) JPS5426926B2 (enrdf_load_stackoverflow)
BE (1) BE800383A (enrdf_load_stackoverflow)
DE (1) DE2328312A1 (enrdf_load_stackoverflow)
FR (1) FR2188508A5 (enrdf_load_stackoverflow)
GB (1) GB1412716A (enrdf_load_stackoverflow)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4001027A (en) * 1975-01-24 1977-01-04 Borden, Inc. Ink containing methylenedisalicylic acid and method for offset printing
US4725315A (en) * 1985-05-31 1988-02-16 Fuji Photo Film Co., Ltd. Desensitizer composition for color developer sheet in pressure sensitive recording system contains a piperidine derivative
US4840927A (en) * 1985-09-09 1989-06-20 Fuji Photo Film Co., Ltd. Desensitizer composition
US5308390A (en) * 1992-09-17 1994-05-03 Deluxe Corporation Ink composition and method of making and using such composition
US5431721A (en) * 1992-09-17 1995-07-11 Deluxe Corporation Ink varnish and composition and method of making the same
US5550097A (en) * 1994-05-31 1996-08-27 Fuji Photo Film Co., Ltd. Color recording method and device
US5549741A (en) * 1992-09-17 1996-08-27 Deluxe Corporation Ink varnish composition
US6531528B1 (en) * 1999-05-05 2003-03-11 Dap Products Inc. Ready to use spackle/repair product containing dryness indicator
US20040224169A1 (en) * 2001-09-11 2004-11-11 Daicel Polymer Ltd. Plated resin molded article and process for producing the same

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3100803A1 (de) * 1981-01-13 1982-08-05 Wacker-Chemie GmbH, 8000 München Mittel zum erhoehen der gleitfaehigkeit von organischen fasern
JPS58108480A (ja) * 1981-07-07 1983-06-28 Furuno Electric Co Ltd 水中探知装置における深度演算回路
US4927971A (en) * 1988-05-11 1990-05-22 Mitsubishi Paper Mills Ltd. Desensitizer composition

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1542058A (fr) * 1966-10-29 1968-10-11 San Abbott Ltd Procédé de préparation de polyuréthanes à partir d'isocyanates et de polyols à l'aide de diazabicycloalkènes comme catalyseurs

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1542058A (fr) * 1966-10-29 1968-10-11 San Abbott Ltd Procédé de préparation de polyuréthanes à partir d'isocyanates et de polyols à l'aide de diazabicycloalkènes comme catalyseurs

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4001027A (en) * 1975-01-24 1977-01-04 Borden, Inc. Ink containing methylenedisalicylic acid and method for offset printing
US4725315A (en) * 1985-05-31 1988-02-16 Fuji Photo Film Co., Ltd. Desensitizer composition for color developer sheet in pressure sensitive recording system contains a piperidine derivative
US4840927A (en) * 1985-09-09 1989-06-20 Fuji Photo Film Co., Ltd. Desensitizer composition
US5308390A (en) * 1992-09-17 1994-05-03 Deluxe Corporation Ink composition and method of making and using such composition
US5338351A (en) * 1992-09-17 1994-08-16 Deluxe Corporation Ink composition and method of making, using and recovering such composition
US5382282A (en) * 1992-09-17 1995-01-17 Deluxe Corporation Ink composition and method of making, using and recovering such composition
US5431721A (en) * 1992-09-17 1995-07-11 Deluxe Corporation Ink varnish and composition and method of making the same
US5549741A (en) * 1992-09-17 1996-08-27 Deluxe Corporation Ink varnish composition
US5550097A (en) * 1994-05-31 1996-08-27 Fuji Photo Film Co., Ltd. Color recording method and device
US6531528B1 (en) * 1999-05-05 2003-03-11 Dap Products Inc. Ready to use spackle/repair product containing dryness indicator
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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GB1412716A (en) 1975-11-05
DE2328312A1 (de) 1973-12-13
JPS4915513A (enrdf_load_stackoverflow) 1974-02-12
JPS5426926B2 (enrdf_load_stackoverflow) 1979-09-06
FR2188508A5 (enrdf_load_stackoverflow) 1974-01-18
BE800383A (fr) 1973-10-01

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