EP0013698B1 - Procédé de préparation de feuilles renforcées imprégnées de résines synthétiques par saturation de surfaces fibreuses et feuilles ainsi obtenues - Google Patents

Procédé de préparation de feuilles renforcées imprégnées de résines synthétiques par saturation de surfaces fibreuses et feuilles ainsi obtenues Download PDF

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Publication number
EP0013698B1
EP0013698B1 EP79104248A EP79104248A EP0013698B1 EP 0013698 B1 EP0013698 B1 EP 0013698B1 EP 79104248 A EP79104248 A EP 79104248A EP 79104248 A EP79104248 A EP 79104248A EP 0013698 B1 EP0013698 B1 EP 0013698B1
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EP
European Patent Office
Prior art keywords
synthetic resin
resin dispersion
linking
resin
acrylic
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Expired
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EP79104248A
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German (de)
English (en)
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EP0013698A1 (fr
Inventor
Helmut Dr. Moroff
Hanns Dr. Bössler
Hans Hauser
Gerhard Ladisich
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Roehm GmbH Darmstadt
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Roehm GmbH Darmstadt
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Classifications

    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/20—Macromolecular organic compounds
    • D21H17/33—Synthetic macromolecular compounds
    • D21H17/34—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D21H17/41—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing ionic groups
    • D21H17/44—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing ionic groups cationic
    • D21H17/45—Nitrogen-containing groups
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/20—Macromolecular organic compounds
    • D21H17/33—Synthetic macromolecular compounds
    • D21H17/34—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D21H17/37—Polymers of unsaturated acids or derivatives thereof, e.g. polyacrylates
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/20—Macromolecular organic compounds
    • D21H17/33—Synthetic macromolecular compounds
    • D21H17/34—Synthetic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • D21H17/37—Polymers of unsaturated acids or derivatives thereof, e.g. polyacrylates
    • D21H17/375—Poly(meth)acrylamide
    • D—TEXTILES; PAPER
    • D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
    • D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
    • D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
    • D21H17/20—Macromolecular organic compounds
    • D21H17/33—Synthetic macromolecular compounds
    • D21H17/46—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D21H17/47—Condensation polymers of aldehydes or ketones
    • D21H17/49—Condensation polymers of aldehydes or ketones with compounds containing hydrogen bound to nitrogen
    • 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
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31855—Of addition polymer from unsaturated monomers
    • Y10T428/3188—Next to cellulosic
    • Y10T428/31895—Paper or wood
    • Y10T428/31906—Ester, halide or nitrile of addition polymer
    • 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
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31942—Of aldehyde or ketone condensation product
    • Y10T428/31949—Next to cellulosic
    • Y10T428/31964—Paper
    • 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
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/259—Coating or impregnation provides protection from radiation [e.g., U.V., visible light, I.R., micscheme-change-itemave, high energy particle, etc.] or heat retention thru radiation absorption
    • 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
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2631—Coating or impregnation provides heat or fire protection
    • Y10T442/2721—Nitrogen containing
    • 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
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/273—Coating or impregnation provides wear or abrasion resistance

Definitions

  • thermoplastic materials By impregnating paper, non-woven fabrics and other fibrous fabrics (textiles) with thermoplastic materials, films can be produced that are characterized by tempered surfaces and improved mechanical properties.
  • plastic-impregnated paper foils decorative foils are used for the surface finishing of wood and other suitable materials.
  • DE-A-2 135 072 recommends a process for producing high-gloss surfaces of decorative papers, in which a decorative base paper is impregnated or coated with a filler-free mixture of a thermoplastic and a self-crosslinking, aqueous dispersion based on acrylate, then dried and coated with a high-gloss polish Calendered roll at a temperature between 120 and 180 ° C.
  • linear polymers with repeating N-methylolamide units and with these groups capable of reaction are suitable, preferably in the form of aqueous dispersions in a mixture with thermosetting aminoplast resins, for impregnating or coating nonwoven fabrics.
  • DE-B-16 19 228 relates to a process for the continuous production of nonwoven or nonwoven fabrics impregnated with polymers and heat-cured under pressure.
  • the substrates are continuously impregnated with a mixture of self-crosslinking group-containing acrylic ester polymers or copolymers and thermosetting polymers, the proportion of thermosetting polymers in the impregnating agent being between 5 and 50 percent by weight, and the impregnated nonwovens or woven fabrics are then continuously cured in a heated calender.
  • Impregnated foils of the type mentioned above should, in order to be suitable as decorative foils, preferably have a closed surface, a high tear resistance, sufficient dimensional stability, high resistance, especially against thermal stress and against solvents, and good adhesiveness.
  • thermoplastic polymer can have a relatively great influence on the quality of the finished film.
  • high-quality reinforced films can be obtained by impregnating raw paper or nonwoven fabric with a mixture which on the one hand contains a commercially available, water-soluble urea resin and, on the other hand, an aqueous synthetic resin dispersion with very finely divided particles, the synthetic resin dispersion in the interest of processability and the surface design of the film is still thermoplastically deformable and uncrosslinked at the start of drying, and the crosslinking with the urea resin is brought about by the further heat treatment.
  • these are aqueous dispersions of polymers which have crosslinkable groups which, however, do not self-crosslink under the conditions to be used.
  • the monomers suitable as building blocks of the synthetic resin dispersions to be used according to the invention therefore have the prerequisite that they can react with added (external) reactive units.
  • Such building blocks accessible to external crosslinking are, for example, monomers containing hydroxyl, amino, amide or carboxyl functions.
  • the polymers or copolymers in question are otherwise prepared, for example, on the basis of vinyl esters of lower carboxylic acids, for example having 2 to 4 carbon atoms, such as vinyl acetate, of butadiene or chlorobutadiene with styrene and / or (meth) acrylate esters.
  • suitable dispersions are composed, for example, of olefins, vinyl chloride, vinylidene chloride, styrene or the mixtures of these monomers with one another or with further modifying comonomers, such as, for example, vinyl ethers.
  • a preferred class of dispersions consists of the esters of acrylic and / or methacrylic acid with e, to C 20 alcohols, preferably with C 1 to C 8 alcohols, preferably esters of alcohols with 1 to 4 C atoms, the main amount of the plastic.
  • acrylic and methacrylic acid for example, come as modifying comonomers accessible to external crosslinking.
  • the acrylic and methacrylamide in question. as well as hydroxy and amino alkyl esters of (meth) acrylic acid, which are represented by the formula wherein A is an optionally branched alkyl radical having 2 to 6 carbon atoms, Z is OH.
  • R represents hydrogen or a methyl radical and R, represents hydrogen or an alkyl radical with 1 to 8 carbon atoms, can be played.
  • the proportion of the above-described monomers accessible to external crosslinking is generally 0.5 to 15% by weight, preferably 2-10% by weight, based on the total polymer.
  • acrylic resin dispersions which are composed of methyl methacrylate, a (meth) acrylic ester of an alcohol having 2 to 8 carbon atoms, methacrylic acid amide and methacrylic acid are preferred.
  • the selection and amount of the (meth) acrylic esters of C 2 -C 8 alcohols depend on the desired flexibility of the reinforced film.
  • the preparation of the dispersions to be used according to the invention is known per se; it can be carried out, for example, in accordance with DE-A-1804159.3.
  • the production process is expediently carried out in such a way that a finely divided polymer, i.e. is obtained with a particle radius below 100 nm.
  • aminoplasts provided as the second component of the impregnation mixture according to the invention for impregnating raw papers or nonwovens are the usual precondensates made from urea-formaldehyde (cf. K. Lindner in “Tenside-Textile Aid-Detergent Raw Materials”, Stuttgart 1964, pp. 244-258 ), of which various types are commercially available.
  • the impregnation mixture according to the invention contains the aqueous synthetic resin dispersion of the type described above and the water-soluble aminoplast resin in comparable proportions, for example in a ratio of 10: 1 to 1:10, preferably about 1: 1, calculated in each case on a dry substrate.
  • the soaking liquors generally contain 25 to 60% by weight of total solid (dry content), preferably 35 to 45% by weight.
  • the base papers or nonwoven fabrics can optionally be pretreated in a suitable manner, for example in the manner recommended in DE-B-17 71 903 by pre-impregnation with a polycationic compound or their addition in the manufacture of the base paper.
  • the impregnation liquor can be applied in a manner known per se, for example by leading the paper or nonwoven web through a trough filled with the liquor * .
  • the webs can also be sufficiently impregnated by roller application, spraying or knife application.
  • the amount of resin to be applied can be conveniently adjusted via the concentration and / or viscosity of the soaking liquor. Depending on the requirements of the field of application and the desired final quality, it is usually between 20-150% by weight, preferably 30-80% by weight of the substrate material.
  • the drying process can be directly connected to the treatment with the drinking liquor.
  • the acrylic resin dispersions can be produced by known processes, for example by the emulsion feed process.
  • part of the monomers can be initially emulsified in an aqueous medium and the remaining part of the monomers can be added to the reaction mixture in the form of an aqueous emulsion as the polymerization progresses.
  • the usual anionic, cationic or non-ionic surfactants can be used as emulsifiers. If polycations have been applied to the paper in accordance with DE-B-1771 903 prior to the impregnation, it is advantageous to work with anionic dispersions.
  • suitable anionic surfactants are the sulfuric acid semiesters of higher alcohols.
  • the commercially available, water-soluble per compounds for example hydrogen peroxide and / or alkali metal or ammonium persulfates, may be used as initiators, if appropriate in combination with reducing components (redox systems).
  • reducing components redox systems
  • the reaction temperatures range between room temperature and the boiling point of the systems.
  • the impregnation with the soaking liquor can be carried out by means of an impregnation unit, in which the continuous paper or fiber web is first pre-impregnated by roller application. To vent the pre-soaked web, it is then passed over a so-called breathing distance (dwell time: several seconds). After the air has been removed from the web in this way, the complete impregnation can be carried out in the immersion bath. The excess liquor is then squeezed or stripped off between rollers or doctor blades, thus achieving the desired dosage of the resin layer. For special cases in which particularly good impregnation or one-sided impregnation is desired, a procedure according to DE-A-25 50 980 using a vacuum suction device is appropriate.
  • the impregnated web is passed through a dryer with one or preferably several drying fields without contact.
  • the transport speed of the train depends on the length of the field or fields and the drying temperature.
  • the drying temperature is generally between 60 and 200 ° C. If there are several dry fields, it is advisable to work with graduated temperatures - starting with the lowest temperature. Jet floating dryers are advantageously used as the non-contact drying system.
  • a Paint application device for painting be attached.
  • a suitable sealable adhesive can also be applied using a suitable device, if necessary in a combined procedure.
  • the finished web can then be cut to the desired format or wound up as a roll.
  • the films produced according to the invention are distinguished by their excellent quality.
  • the closed, smooth surface, high resistance to splitting and tearing, high resistance to light and aging, resistance to aggressive substances, heat resistance, easy maintenance and good adhesion can be emphasized. If a matt or semi-matt surface is desired, suitable matting agents can be easily added to the soaking solution.
  • the mixture is kept at this temperature, 0.4 g of potassium persulfate dissolved in 10 g of water are added and 4 minutes later the addition of a previously prepared emulsion of 480 g of water, 7.3 g of sodium dodecyl sulfate, 1.2 g of potassium persulfate and 471 g of ethyl acrylate is started. 251.2 g methyl methacrylate, 15.7 g methacrylic acid and 47.1 g methacrylamide. After the addition (addition time 4 hours), the mixture is kept at 80 ° C. for 1 hour and then cooled to 25 ° C. A 35% aqueous solution of a condensation product of isononylphenol and ethylene oxide (molar ratio 1 50) is then added within 45 minutes and any small amounts of coagulum formed are filtered off through a fine sieve.
  • Example 2 The procedure is as in Example 1, except that 13.2 g of ethyl acrylate and 1.2 g of 2-hydroxyethyl acrylate are used in the initial charge and 722.2 g of ethyl acrylate and 62.8 g of 2-hydroxyethyl acrylate are used in the feed.
  • Absorbent decorative base paper with a basis weight of 80 g / m 2 is in an impregnation liquor consisting of 500 g of the dispersion described in Example 1, 500 g of urea formaldehyde resin (trade name Kautit 420® *. Solids content 50%), 250 g of water and 2 g of ammonium chloride and 2 g Impregnating agent (weakly sulfated beet oil) impregnated in a watering trough.
  • the impregnation is carried out by placing the base paper on the liquor surface for wetting and then immersing it completely.
  • the impregnated paper is then squeezed between two rubber rollers and dried in a drying cabinet at 140 ° C. for 3 minutes.
  • a medium-hard flexible film with a final weight of 124 g / m 2 , a residual moisture content of 4% and a resin quantity of 42.5% (based on the weight of the base paper) is obtained.
  • Example 4 The procedure is as in Example 4, but the impregnation liquor consists of 700 g of dispersion from Example 2, 300 g of urea formaldehyde resin (50% solids content), 250 g of water and 1.5 g of ammonium chloride and 2 g of the wetting agent described in Example 4.
  • the film produced in this way has a highly flexible character (wrapping film), the amount of resin is 41%, the final weight 112.8 g and the residual moisture 5%.
  • An absorbent base paper basis weight 200 gim 2 , is impregnated and further treated in an impregnation liquor which consists of 1,000 g of the dispersion described in Example 3, 600 g of urea formaldehyde (50% solids content), 1.5 ammonium chloride and 3 g of wetting agent .
  • the end product corresponds to a film that is used as edge banding in the furniture and chipboard industry, it has a resin content of 38%, a residual moisture content of 5% and a final weight of 276 g / m 2 .

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Paper (AREA)
  • Laminated Bodies (AREA)
  • Synthetic Leather, Interior Materials Or Flexible Sheet Materials (AREA)
  • Reinforced Plastic Materials (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Claims (8)

1. Procédé pour la fabrication de feuilles renforcées (feuilles de finition) par imprégnation de produits fibreux en nappe, tels que papiers bruts, nappes de fibres ou similaires, avec une résine aminoplaste hydrosolubles et une dispersion aqueuse de résine synthétique, suivie d'un séchage par traitement thermique, caractérisé en ce qu'on utilise, en tant que résine aminoplaste hydrosoluble, une résine à base d'urée et en ce que la dispersion de résine synthétique est faite de particules finement divisées et, en raison du fait qu'elle contient des groupes susceptibles de réticulation par action étrangère, se présente à l'état encore déformable thermoplastiquement et non réticulé au début du séchage, la réticulation par action étrangère étant produite par le traitement thermique ultérieur.
2. Procédé selon la revendication 1, caractérisé en ce qu'on utilise, en tant que dispersion aqueuse de résine synthétique, une dispersion qui contient des fonctions hydroxy, amino, amide ou carboxyle en tant que groupes susceptibles de réticulation par action étrangère.
3. Procédé selon la revendication 1 ou 2, caractérisé en ce qu'on utilise, comme dispersion aqueuse de résine synthétique, le copolymère d'esters d'acide (méth)acrylique avec, en tant que comonomères, l'acide acrylique ou méthacrylique, l'acryl- ou méthacrylamide, un ester hydroxy- et/ou aminoalcoylique de formule.
Figure imgb0004
dans laquelle R est mis pour un atome d'hydrogène ou un radical méthyle, A pour un radical alcoyle à 2-6 atomes de carbone éventuellement ramifié, Z pour un substituant - OH ou NHR, - sur le radical alcoyle, R, représentant un radical alcoyle à 1-8 atomes de carbone ou un atome d'hydrogène.
4. Procédé selon la revendication 3, caractérisé en ce que la proportion des monomères susceptibles de réticulation par action étrangère est comprise entre 0,5 et 15 % en poids, de préférence entre 2 et 10 % en poids, par rapport au polymère total.
5. Procédé selon la revendication 3 ou 4, caractérisé en ce qu'on utilise, en tant que dispersion de résine synthétique, le copolymère de méthacrylate de méthyle, d'esters (méth)acryliques d'alcools en C2 à C8, d'amide d'acide méthacrylique et d'acide méthacrylique.
6. Procédé selon l'une quelconque des revendications 1 à 5, caractérisé en ce que le rayon des particules de la dispersion de résine synthétique est inférieur à 100 nm.
7. Procédé selon l'une quelconque des revendications 1 à 6, caractérisé en ce que le séchage par traitement thermique est effectué à une température comprise entre 80 et 180 °C, de préférence entre 100 et 150 °C.
8. Feuilles renforcées (feuilles de finition), fabriquées d'après le procédé selon l'une quelconque des revendications 1 à 7.
EP79104248A 1979-01-27 1979-10-31 Procédé de préparation de feuilles renforcées imprégnées de résines synthétiques par saturation de surfaces fibreuses et feuilles ainsi obtenues Expired EP0013698B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19792903172 DE2903172A1 (de) 1979-01-27 1979-01-27 Verfahren zur herstellung kunststoffimpraegnierter papiere, faservliese u.dgl.
DE2903172 1979-01-27

Publications (2)

Publication Number Publication Date
EP0013698A1 EP0013698A1 (fr) 1980-08-06
EP0013698B1 true EP0013698B1 (fr) 1983-01-26

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Country Status (5)

Country Link
US (1) US4324832A (fr)
EP (1) EP0013698B1 (fr)
JP (1) JPS55103373A (fr)
BR (1) BR8000296A (fr)
DE (1) DE2903172A1 (fr)

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DE2903172A1 (de) 1980-08-07
JPH0154477B2 (fr) 1989-11-20
US4324832A (en) 1982-04-13
EP0013698A1 (fr) 1980-08-06
DE2903172C2 (fr) 1990-04-19
JPS55103373A (en) 1980-08-07
BR8000296A (pt) 1980-09-30

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