EP0000714B1 - Agent améliorant la rétention, la séparation de l'eau et la préparation, en particulier pour la fabrication du papier - Google Patents

Agent améliorant la rétention, la séparation de l'eau et la préparation, en particulier pour la fabrication du papier Download PDF

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Publication number
EP0000714B1
EP0000714B1 EP78100444A EP78100444A EP0000714B1 EP 0000714 B1 EP0000714 B1 EP 0000714B1 EP 78100444 A EP78100444 A EP 78100444A EP 78100444 A EP78100444 A EP 78100444A EP 0000714 B1 EP0000714 B1 EP 0000714B1
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EP
European Patent Office
Prior art keywords
product
integer
polyethylene glycol
component product
retention
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
EP78100444A
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German (de)
English (en)
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EP0000714A2 (fr
EP0000714A3 (en
Inventor
Rudolf Behn
Lutz Dr. Hoppe
Branislav Dr. Böhmer
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dow Produktions und Vertriebs GmbH and Co OHG
Original Assignee
Wolff Walsrode AG
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Publication of EP0000714A3 publication Critical patent/EP0000714A3/de
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C02—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F—TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE
    • C02F1/00—Treatment of water, waste water, or sewage
    • C02F1/52—Treatment of water, waste water, or sewage by flocculation or precipitation of suspended impurities
    • C02F1/54—Treatment of water, waste water, or sewage by flocculation or precipitation of suspended impurities using organic material
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
    • C08G69/48—Polymers modified by chemical after-treatment
    • 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
    • D21H17/54—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds obtained by reactions forming in the main chain of the macromolecule a linkage containing 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
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S210/00—Liquid purification or separation
    • Y10S210/928—Paper mill waste, e.g. white water, black liquor treated

Definitions

  • the invention relates to polyethylene glycol-polyaminoamide condensation products for retention purposes. Improvement of washable solids, to accelerate the dewatering of suspensions and to process industrial water, waste water and sludge more quickly, especially in the paper industry.
  • a polyamino amide production of the polyamino amide, for example, by condensation of adipic acid and diethylene triamine
  • a polyether with a filiform molecular structure and terminal tertiary amino groups production of the polyether, for example from glycol, epichlorohydrin and dimethylamine
  • this adduct is then reacted with epichlorohydrin.
  • the aforementioned adduct is already highly branched, so that when it is subsequently crosslinked with epichlorohydrin, it leads to a considerably entangled molecular structure, which has a disadvantageous effect when this auxiliary is used as a retention and drainage agent. because because of this tangled molecular structure, only a fraction of the auxiliary molecule can be fully effective in the above sense.
  • polyethylene polyamines having 15 to 500 alkyleneimine units with a crosslinking agent obtained from the reaction of polyalkylene glycol ether with epichlorohydrin, in amounts of 0.08 to 0.001 mol of crosslinking agent per 1 equivalent of nitrogen in the polyalkylene polyamine to react and thus to crosslink.
  • a crosslinking agent obtained from the reaction of polyalkylene glycol ether with epichlorohydrin, in amounts of 0.08 to 0.001 mol of crosslinking agent per 1 equivalent of nitrogen in the polyalkylene polyamine to react and thus to crosslink.
  • the basic polyamides used here are high molecular weight water-soluble products which are obtained by the action of compounds which are polyfunctional with respect to amino groups on basic polyamides dissolved or dispersed in water from polyvalent amines, dicarboxylic acids and aminocarboxylic acids or lactams containing at least three carbon atoms, and for their preparation from 1 val of the basic amino groups contained in the basic polyamides, less than 1 val of reactive groups were used in the polyfunctional compounds.
  • the polyalkylene polyamines are crosslinked with, for example, epichlorohydrin.
  • the resulting acid which has been subsequently acidified, has a structure due to the procedural interconnected starting blocks, in which, for example, cationic side chains are missing, which is why optimal reaction and dewatering performance cannot yet be achieved.
  • composition as a building block has polyalkylene glycol compounds and is characterized in that it is a reaction product C which results from the reaction of an aliphatic polyethylene glycol ether amine as partial product A which, by the action of a), 0.25 to 1 mol, preferably 0.7 to 1 mole, of a polyalkylene polyamine of the general formula where y and z are an integer between 2 and 4, preferably 2 and 3; n represents an integer between 2 and 5 and m represents an integer between 0 and 5, preferably between 0 and 3, and / or 0.25 to 2 mol, preferably 0.8 to 2 mol, of an amine of the general formula where R and R 2 are
  • products can be used equally well as polyfunctional compounds here, e.g. B. can be selected from a group which includes epibromohydrin, epifluorohydrin, the dihaloalkanes, glyoxal-bis-acrylamide, bis-acrylamidoacetic acid, acrylaminoglycolic acid, tetraallyloxyethane and other compounds, epichlorohydrin is preferred here.
  • reaction product c) consists of 1 mol of the polyethylene glycol of the general formula where r is an integer between 1 and 27, preferably 1 and 24, when 2 mol of epichlorohydrin has been formed and when 0.5 to 7, preferably 2.5 to 6.8 mol, of partial product B, based on polyalkylene polyamine of the basic polyaminoamide, has been implemented.
  • the aid can be varied in a relatively wide range without reducing its special performance.
  • tools can be obtained in the aforementioned manner, the z. B. in 20% by weight aqueous solution at 25 ° C have a viscosity of 50 on the one hand to 1000 mPa on the other.
  • This so-called partial product A in the form of its chloropolyethylene glycol ether amine is then combined with the part product B known per se, namely a basic polyamino amide to form a polyethylene glycol ether amine polyamino amide, which is called intermediate AB as mentioned above.
  • This intermediate product AB is then reacted again with a polyfunctional compound selected from the special group of polyfunctional compounds mentioned above, here preferably with epichlorohydrin, in such a way that the end product C is finally in the form of a polyethylene glycol ether-amine-polyaminoamide-epichlorohydrin resin.
  • Chloride determination (measurement method, at the same time explanation of the following Table 2)
  • the above-mentioned newsprint suspension is obtained by mechanical defibration of commercially available newsprint and subsequent speck-free beating of the defibrated product in a conventional kitchen mixer.
  • the measurements are carried out at a pH of 6.5 and 4.8, which is adjusted with a 1% by weight aqueous alum solution.
  • the fiber concentration is 2 g / l water.
  • the 0 sample listed in Table 5 is of course dependent on the choice of waste paper used.
  • the same determination method is used both for the examples according to the invention and for the further comparative examples in order to achieve comparable values.
  • the filler retention is characterized by the ash content of paper sheets that are produced on the »Rapid-Köthen réelle « in accordance with leaflet V / 8/57 of the Association of Pulp and Paper Chemists and Engineers (old version was leaflet 108).
  • Diethylenetriamine is a 100% pure substance.
  • Polyethylene glycol ether is present as the pure substance, the number added in the table indicates the average molecular weight of this compound, for example 400; 600; 1000; 6000 etc.
  • Polyaminoamide resin solution which contains the secondary amines as a reactive group. 1 mole of this compound corresponds to 1 NH.
  • Adipic acid is present as a 100 weight percent solid.
  • Caprolactam is a 100% by weight solid.
  • Salt from adipic acid and hexamethylenediamine is present as a 100 percent solid
  • Diethanolamine is always available as a 100 percent by weight substance.
  • Trimethylamine is always available as a 45 weight percent aqueous solution.
  • Dimethylamine is always available as a 40 weight percent aqueous solution.
  • intermediate B in the relevant examples 1b to 3b always contains the same amounts of adipic acids (AS) and diethylenetriamine (DTRA).
  • AS adipic acids
  • DTRA diethylenetriamine
  • caprolactam (CL) was also used, and in example 3b the salt of adipic acid and hexamethylenediamine (hexamethylenediammonium adipate; AH-S) was also used.
  • the reaction takes place at a reaction temperature of at most 65 ° C in a time of 2.5 hours in the form of an addition reaction.
  • the resulting product namely polyethylene glycol bis-ß-hydroxy-y-chloropropyl ether, is now after adding 271.7 ml of deionized water, which is stirred in at 65 ° C in two minutes, with 35.4 g of DTRA, corresponding to 0.336 moles offset via an inlet funnel.
  • the temperature is kept at 65 ° C if necessary by means of water cooling. After one hour, the reaction solution temperature drops due to the completion of the reaction between the aforementioned substances.
  • the partial product A ( ⁇ -hydroxy-y-chloropropylpolyethylene glycol ether- ⁇ -hydroxy-y-propylamine) formed in this way gave the following values in its analysis:
  • adipic acid (100% by weight corresponding to 10 mol, solid) were placed in a pressure vessel designed as a steel autoclave with a stirrer, a temperature sensor in the form of a thermal sensor and a distillation condenser; 1124.5 g of diethylenetriamine (100% by weight corresponding to 10.9 mol; liquid) and 226.34 g of caprolactam (100% by weight corresponding to 2 mol; solid) were introduced in the form of their pure substances. After the above-mentioned filling material has been overlaid with oxygen-free nitrogen, which thus replaces the supernatant residual gas mixture, the contents of the vessel are heated to 160 ° C. after the end of the reaction vessel and left at this temperature for 30 minutes with stirring.
  • the water of reaction released is then distilled off (a total of 360 ml, corresponding to 100% of theory).
  • the reaction mixture, which is now free of condensation, is then further heated to 180 ° C. and stirred at this temperature for a further two hours.
  • the mixture reacts further, nitrogen being continuously passed through the condensing reaction mass.
  • Example 10 of DE-OS 2 434 816 was reworked by adding the polyaminoamide V 12 (produced from adipic acid, diethylenetriamine and hexamethylenediamine adipate) with the crosslinker V 4 (reaction product from polyethylene glycol and epichlorohydrin) according to the description of Examples 1 to 14 on page 12 of the DE-OS was implemented.
  • the viscosity of the 18 percent solution the condensation products were 609 mPa. s (shear rate 24.5 sec -1 at 20 ° C).
  • the polyethylene glycol-polyaminoamide condensation product according to the invention for improving the retention of washable solids, for accelerating the dewatering of suspensions and for the faster treatment of industrial waters, wastewater and sludges by adding basic water-soluble polymers as an aqueous polymer solution can be used primarily advantageously in the paper industry, but is at the same time advantageous also very well suited for the treatment of industrial water, waste water purification and sludge conditioning in other branches of industry.
  • sludge treatment includes the treatment of fresh sludge and activated sludge as well as the sludge thickening and sludge flotation processes known per se, in which the aid according to the invention can be used very well.
  • auxiliaries for example in the clarification process, are insensitive to the addition of a number of different substances, which is why it is readily possible, for example inorganic flocculants, such as those based on aluminum and iron salts or on the base of lime compounds are commercially available, without the auxiliary properties of the invention being adversely affected in terms of their use properties.
  • the aid according to the invention is used in sedimentation and clarification tanks, it is recommended to use it in an amount of approximately 0.1 to 4 mg per liter of the substance to be clarified.
  • the water can be removed from the sludge better and more quickly if the auxiliary according to the invention is used in amounts of about 2 to 12 kg per ton of dry sludge is added to the substance to be treated.
  • the sludge to be treated is to be stabilized, it is appropriate to add about 50 to 150 mg of the Aids according to the invention are added to the sludge for each corresponding unit of quantity.
  • the stabilization advantageously occurs by promoting the formation of tear-resistant flakes by the aid.
  • the said auxiliary can of course not only be added separately, but also in admixture with the other substances required in papermaking, such as dyes, antioxidants, optical brighteners and fluorescent agents, since the aid is not sensitive to these substances.
  • the aforementioned additional method of prior mixing of the additives is often used because, for example, optical brighteners and fluorescent agents are generally only required in small amounts in the paper in order to achieve the desired change in the appearance of the paper.
  • the auxiliary according to the invention can of course also be used in completely different areas than those mentioned above.
  • the agent can be used as well as an improver for the wet strength of fabrics (especially paper). use, in the latter case, however, advantageously after acidification of the agent.
  • the auxiliary according to the invention is very stable in storage even in the basic medium if, as the person skilled in the art knows, only as much crosslinking agent as required is added in the preparation of the crosslinking agent, for example using epichlorohydrin.
  • the agent can still be used, but must then be acidified in order to achieve a suitable storage stability, which also reliably prevents any gelling that might otherwise occur in this case.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Hydrology & Water Resources (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Environmental & Geological Engineering (AREA)
  • Water Supply & Treatment (AREA)
  • Paper (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Polyamides (AREA)
  • Separation Of Suspended Particles By Flocculating Agents (AREA)

Claims (6)

1. Produits de condensation de polyéthylèneglycol-polyaminoamides par réaction d'une polyéthylèneglycoiéthéramine aliphatique comme produit partiel A avec des polyaminoamides basiques comme produit partiel B, avec formation d'un produit intermédiaire AB et réaction du produit intermédiaire AB obtenu avec des composés polyfonctionnels, le produit partiel A ayant été formé par l'action de a) 0,25 à 1 mole d'une polyalkylènepolyamine de formule générale
Figure imgb0019
dans laquelle y et z représentent un nombre entier entre 2 et 4, n un nombre entier entre 2 et 5 et m un nombre entier entre 0 et 5, et/ou b) 0,25 à 2 moles d'une amine de formule générale
Figure imgb0020
dans laquelle Ri et R2 sont des restes alkyles identiques ou différents de formule générale CxH2x+l ou CxH2x ― OH, dans lesquels x est un nombre entier entre 1 et 4 et R3 est l'hydrogène ou un reste alkyle de formule générale CxH2x+1, dans lequel x est un nombre entier entre 1 et 4, sur le produit de réaction c) d'un polyéthylèneglycol et de l'épichlorhydrine, le produit partiel B ayant été formé à partir d'au moins une polyalkylènepolyamine et/ou au moins un acide aminocarboxylique ou son lactame et/ou l'adipate d'hexaméthylènediammonium, les proportions dans la formation du produit intermédiaire AB étant choisies de telle sorte que l'on ajoute à chaque mole, rapportée au polyéthylèneglycol du produit partiel A, 0,5 à 7 moles rapportées à la polyalkylènepolyamine du produit partiel B et le produit intermédiaire AB ayant été obtenu par réaction des groupes halogènes du produit partiel A avec les groupements NH du produit partiel B avec élimination d'acides halohydriques.
2. Produits de condensation selon la revendication 1, caractérisés en ce que l'on a utilisé l'épichlorhydrine comme composé polyfonctionnel.
3. Produits de condensation selon les revendications 1 et 2, caractérisés en ce que le produit de réaction c) a été formé à partir d'une mole du polyéthylèneglycol de formule générale
Figure imgb0021
dans laquelle r est un nombre entier entre 1 et 27, avec 2 moles d'épichlorhydrine.
4. Produits de condensation selon les revendications 1-3, caractérisés en ce que le produit partiel A a été obtenu par l'action de 0,7 à 1 mole de polyalkylènepolyamine a) dans laquelle y ou z est 2 ou 3 et/ou 0,8 à 2 moles d'amine b) sur le produit de réaction c) et on le fait réagir ensuite avec 2,5 - 6,8 moles du produit partiel B.
5. Utilisation des produits de condensation selon les revendications 1 -4 en solution aqueuse de polymère pour l'amélioration de la rétention de substances solides rinçables, pour l'accélération de la déshydratation de suspensions et pour le traitement plus rapide d'eaux industrielles, d'eaux résiduaires et de boues.
6. Utilisation selon la revendication 5 dans l'industrie de préparation du papier.
EP78100444A 1977-08-13 1978-07-19 Agent améliorant la rétention, la séparation de l'eau et la préparation, en particulier pour la fabrication du papier Expired EP0000714B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2736651 1977-08-13
DE19772736651 DE2736651A1 (de) 1977-08-13 1977-08-13 Hilfsmittel zur verbesserung der retention, entwaesserung und aufbereitung, insbesondere bei der papierherstellung

Publications (3)

Publication Number Publication Date
EP0000714A2 EP0000714A2 (fr) 1979-02-21
EP0000714A3 EP0000714A3 (en) 1979-03-21
EP0000714B1 true EP0000714B1 (fr) 1982-03-31

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ID=6016378

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EP78100444A Expired EP0000714B1 (fr) 1977-08-13 1978-07-19 Agent améliorant la rétention, la séparation de l'eau et la préparation, en particulier pour la fabrication du papier

Country Status (9)

Country Link
US (1) US4267059A (fr)
EP (1) EP0000714B1 (fr)
JP (1) JPS5432186A (fr)
AT (1) AT365681B (fr)
CA (1) CA1124963A (fr)
DE (2) DE2736651A1 (fr)
FI (1) FI64177C (fr)
IT (1) IT1112697B (fr)
NO (1) NO151625C (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2141130A (en) * 1983-06-09 1984-12-12 Grace W R & Co Polyamidoaminepolyamines
EP0158247A1 (fr) * 1984-04-11 1985-10-16 Bayer Ag Agent auxiliaire de papier
US5395412A (en) * 1991-01-15 1995-03-07 Poly Id Ag Method and apparatus for the treatment of fiber pieces
WO1999006469A1 (fr) * 1997-07-29 1999-02-11 Hercules Incorporated Resines de polyamidoamine/epichlorhydrine supportant des chaines laterales de polyol comme agents de resistance a l'etat sec
US5886095A (en) * 1996-05-30 1999-03-23 Wolff Walsrode Ag Process for the preparation of retention and dewatering agents based on polyamino-ethers

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4347339A (en) * 1981-05-08 1982-08-31 Nalco Chemical Company Cationic block copolymers
US6896769B2 (en) 1999-01-25 2005-05-24 Kimberly-Clark Worldwide, Inc. Modified condensation polymers containing azetidinium groups in conjunction with amphiphilic hydrocarbon moieties
US6517678B1 (en) 2000-01-20 2003-02-11 Kimberly-Clark Worldwide, Inc. Modified polysaccharides containing amphiphillic hydrocarbon moieties
US6596126B1 (en) 1999-01-25 2003-07-22 Kimberly-Clark Worldwide, Inc. Modified polysaccharides containing aliphatic hydrocarbon moieties
US6398911B1 (en) 2000-01-21 2002-06-04 Kimberly-Clark Worldwide, Inc. Modified polysaccharides containing polysiloxane moieties
US6465602B2 (en) 2000-01-20 2002-10-15 Kimberly-Clark Worldwide, Inc. Modified condensation polymers having azetidinium groups and containing polysiloxane moieties
US10662586B2 (en) 2017-06-28 2020-05-26 Gpcp Ip Holdings Llc Cationic polyetheramine dispersants for preparing papermaking stock

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1771043C3 (de) * 1968-03-27 1979-05-23 Bayer Ag, 5090 Leverkusen Selbstvernetzende wasserlösliche Produkte und deren Verwendung als Naßfestmittel für Papier
DE1771814C2 (de) * 1968-07-16 1974-05-09 Bayer Ag, 5090 Leverkusen Hilfsmittel-Verwendung für die Papierfabrikation
CH541595A (de) * 1970-06-05 1973-09-15 Sandoz Ag Verfahren zur Herstellung von neuen Polyätheraminen
DE2353430C2 (de) * 1973-10-25 1982-04-15 Wolff Walsrode Ag, 3030 Walsrode Verfahren zur Herstellung von kationischen Polyaminopolyamiden und deren Verwendung als Papiererzeugungshilfsmittel
DE2434816C3 (de) * 1974-07-19 1981-01-22 Basf Ag, 6700 Ludwigshafen Verfahren zur Herstellung von stickstoffhaltigen Kondensationsprodukten und deren Verwendung als Retentionsmittel, Flockungsmittel und Entwässerungsbeschleuniger bei der Papierherstellung

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2141130A (en) * 1983-06-09 1984-12-12 Grace W R & Co Polyamidoaminepolyamines
FR2547303A1 (fr) * 1983-06-09 1984-12-14 Grace W R Ltd Polyamidoaminepolyamine soluble dans l'eau et procede de production d'un produit en feuille a base d'une fibre cellulosique
EP0158247A1 (fr) * 1984-04-11 1985-10-16 Bayer Ag Agent auxiliaire de papier
US5395412A (en) * 1991-01-15 1995-03-07 Poly Id Ag Method and apparatus for the treatment of fiber pieces
US5886095A (en) * 1996-05-30 1999-03-23 Wolff Walsrode Ag Process for the preparation of retention and dewatering agents based on polyamino-ethers
WO1999006469A1 (fr) * 1997-07-29 1999-02-11 Hercules Incorporated Resines de polyamidoamine/epichlorhydrine supportant des chaines laterales de polyol comme agents de resistance a l'etat sec
US6165322A (en) * 1997-07-29 2000-12-26 Hercules Incorporated Polyamidoamine/epichlorohydrin resins bearing polyol sidechains as dry strength agents
AU732514B2 (en) * 1997-07-29 2001-04-26 Hercules Incorporated Polyamidoamine/epichlorohydrin resins bearing polyol sidechains as dry strength agents

Also Published As

Publication number Publication date
US4267059A (en) 1981-05-12
NO151625B (no) 1985-01-28
ATA587278A (de) 1981-06-15
FI782461A7 (fi) 1979-02-14
IT1112697B (it) 1986-01-20
FI64177C (fi) 1983-10-10
IT7826760A0 (it) 1978-08-11
AT365681B (de) 1982-02-10
NO151625C (no) 1985-05-08
DE2861707D1 (en) 1982-05-06
JPS5432186A (en) 1979-03-09
EP0000714A2 (fr) 1979-02-21
NO782730L (no) 1979-02-14
CA1124963A (fr) 1982-06-08
FI64177B (fi) 1983-06-30
EP0000714A3 (en) 1979-03-21
DE2736651A1 (de) 1979-02-15

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