EP0144738A1 - Succinic monodialkyl amides as water-soluble corrosion inhibitors - Google Patents

Succinic monodialkyl amides as water-soluble corrosion inhibitors Download PDF

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EP0144738A1
EP0144738A1 EP84113211A EP84113211A EP0144738A1 EP 0144738 A1 EP0144738 A1 EP 0144738A1 EP 84113211 A EP84113211 A EP 84113211A EP 84113211 A EP84113211 A EP 84113211A EP 0144738 A1 EP0144738 A1 EP 0144738A1
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corrosion inhibitors
carbon atoms
water
amides
mono
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EP0144738B1 (en
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Alfred Dr. Struve
Horst Dr. Upadek
Jürgen Dr. Geke
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Henkel AG and Co KGaA
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    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23F—NON-MECHANICAL REMOVAL OF METALLIC MATERIAL FROM SURFACE; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL; MULTI-STEP PROCESSES FOR SURFACE TREATMENT OF METALLIC MATERIAL INVOLVING AT LEAST ONE PROCESS PROVIDED FOR IN CLASS C23 AND AT LEAST ONE PROCESS COVERED BY SUBCLASS C21D OR C22F OR CLASS C25
    • C23F11/00—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent
    • C23F11/08—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids
    • C23F11/10—Inhibiting corrosion of metallic material by applying inhibitors to the surface in danger of corrosion or adding them to the corrosive agent in other liquids using organic inhibitors
    • C23F11/14—Nitrogen-containing compounds
    • C23F11/145—Amides; N-substituted amides

Definitions

  • the invention relates to the use of alkanolamine salts of alkenylsuccinic acid halamides as corrosion inhibitors in aqueous systems.
  • reaction products of alkenylsuccinic anhydrides with long-chain dialkylamines are known for use in the oil phase.
  • U.S. Patent 3,546,151 describes u. a. the reaction products with excess di-tallow amine.
  • the wax-like succinic acid half-amine salts obtained can be used as corrosion inhibitors in water-repellent media.
  • the proposed alkanolamine salts of Cp to Cg alkenylsuccinic acid or maleinic acid are distinguished by the fact that they foam only slightly. However, the anti-corrosive properties are not satisfactory.
  • the alkanolamine salts of the alkenylsuccinic acid halamides of the general formulas (I) and (II) where R is an alkenyl radical having 6 to 18 carbon atoms and R I and R II 1 to 10 carbon atoms containing alkyl groups can be used as corrosion inhibitors in aqueous systems and have a comparatively excellent effectiveness.
  • the compounds mentioned have only a low tendency to foam, sufficient solubility in water and are therefore particularly suitable for use as rust inhibitors in aqueous media.
  • the compounds used can be prepared by reacting maleic anhydride with C 6 -C 18 -alkenes. Alkenylsuccinic anhydrides are obtained, which are added with dialkylamines each having 1 to 10 carbon atoms in the alkyl radical in a molar ratio of 1: 1 at about 70 to 90 ° C. the corresponding half amides are implemented.
  • the salts of the half-amides used are prepared by adding equimolar or excess amounts of alkanolamines.
  • alkanolamines preferably mono-, di- or triethanolamines, are expediently suitable.
  • the compounds are used which have an alkenyl radical R having 10 to 18 carbon atoms and in the amide group alkyl radical R' according to formulas I and II. R "with 3 to 8 carbon atoms.
  • olefins can be used to prepare the precursors alkenylsuccinic anhydride.
  • the reaction with the amines is carried out in equimolar proportions or with a slight excess of anhydride.
  • the dialkylamines can be straight-chain or branched.
  • the compounds that can be produced in this way are suitable alone or in combinations with other substances as water-soluble anticorrosive constituents in rust inhibitors, technical cleaning agents in metalworking and in cooling lubricants.
  • the agents according to the invention are used in concentrations of 0.01 to 15 percent by weight, preferably 0.05 to 1.0 percent by weight, each calculated as alkenylsuccinic acid halamide.
  • the half amide is converted into the alkanolamine salts by gentle heating with excess mono-, di- or triethanolamine in the presence of a little water.
  • Example 1 The compounds mentioned in Examples 1 and 2 were tested in the form of the mono-, di- and triethanolamine salts in a gray cast iron filter test in accordance with DIN 51360. Water with a hardness of 20 ° d according to the above DIN instructions was used as the test medium. Within the test series to be compared, testing was carried out at constant pH values (8.0 to 9.5).

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Organic Chemistry (AREA)
  • Preventing Corrosion Or Incrustation Of Metals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Lubricants (AREA)

Abstract

The C2-4-alkanolamine salts of alkenyl succinic acid dialkyl semiamides are used as corrosion inhibitors in aqueous systems.

Description

Gegenstand der Erfindung ist die Verwendung von Alkanolaminsalze von Alkenylbernsteinsäurehalbamiden als Korrosionsinhibitoren in wäßrigen Systemen.The invention relates to the use of alkanolamine salts of alkenylsuccinic acid halamides as corrosion inhibitors in aqueous systems.

Es sind bereits zahlreiche Derivate der Bernsteinsäure als Korrosionsschutzmittel vorgeschlagen worden. So sind aus der US-Patentschrift 2 490 744 Umsetzungsprodukte von Alkenylbernsteinsäureanhydriden mit primären Aminen im Molverhältnis von 1,25 bis 2 : 1 als Rostschutzmittel in Schmierölen bekannt, wobei die Gesamtzahl der Kohlenstoffatome im Reaktionsprodukt zwischen 28 und 50 liegen soll.Numerous derivatives of succinic acid have already been proposed as anti-corrosion agents. For example, US Pat. No. 2,490,744 shows reaction products of alkenylsuccinic anhydrides with primary amines in a molar ratio of 1.25 to 2: 1 as rust inhibitors in lubricating oils, the total number of carbon atoms in the reaction product being said to be between 28 and 50.

Desgleichen sind für den Einsatz in der Ölphase Umsetzungsprodukte von Alkenylbernsteinsäureanhydriden mit langkettigen Dialkylaminen bekannt. Die US-Patenschrift 3 546 151 beschreibt u. a. die Umsetzungsprodukte mit überschüssigem Di-talg-amin. Die erhaltenen wachsartigen Bernsteinsäure halbamid-aminsalze sind als Korrosionsinhibitoren im wasserabstoßenden Medien verwendbar.Likewise, reaction products of alkenylsuccinic anhydrides with long-chain dialkylamines are known for use in the oil phase. U.S. Patent 3,546,151 describes u. a. the reaction products with excess di-tallow amine. The wax-like succinic acid half-amine salts obtained can be used as corrosion inhibitors in water-repellent media.

Für rein wäßrige Systeme ist die rostschützende Verwendung von Alkanolaminsalzen von C8-bis Cg-Alkenylbernsteinsäure aus dem deutschen Patent 29 43 963 vorbekannt. Auch in der europäischen Patentschrift 2780 wird die Verwendung von Maleinamidsäurealkanolaminsalzen, die am Amidrest eine C8- bis C12-Isoalkylgruppe tragen, als Korrosionsschutzmittel in wäßrigen Systemen vorbeschrieben.For purely aqueous systems, the rust-protecting use of alkanolamine salts of C 8 to Cg-alkenyl succinic acid is previously known from German Patent 29 43 963. European patent specification 2780 also describes the use of maleamic acid alkanolamine salts which carry a C 8 to C 12 isoalkyl group on the amide residue as corrosion inhibitors in aqueous systems.

Die vorgeschlagenen Alkanolaminsalze der Cp- bis Cg-Alkenylbernsteinsäure beziehungsweise -Maleinamidsäure zeichnen sich dadurch aus, daß sie nur gering schäumen. Allerdings sind die antikorrosiven Eigenschaften nicht zufriedenstellend.The proposed alkanolamine salts of Cp to Cg alkenylsuccinic acid or maleinic acid are distinguished by the fact that they foam only slightly. However, the anti-corrosive properties are not satisfactory.

Es wurde nun gefunden, daß überraschenderweise die Alkanolaminsalze der Alkenylbernsteinsäurehalbamide der allgemeinen Formeln (I) und (II)

Figure imgb0001
Figure imgb0002
 wobei R einen Alkenylrest mit 6 bis 18 Kohlenstoffatomen und RI und RII 1 bis 10 Kohlenstoffatome enthaltende Alkylgruppen darstellen als Korrosionsinhibitoren in wäßrigen Systemen verwendet werden können und eine vergleichsweise hervorragende Wirksamkeit vorweisen. Darüber hinaus zeigen die genannten Verbindungen nur eine geringe Schaumneigung, eine ausreichende Wasserlöslichkeit und sind daher zum Einsatz als Rostschutzmittel in wäßrigen Medien besonders geeignet.It has now been found that, surprisingly, the alkanolamine salts of the alkenylsuccinic acid halamides of the general formulas (I) and (II)
Figure imgb0001
Figure imgb0002
 where R is an alkenyl radical having 6 to 18 carbon atoms and R I and R II 1 to 10 carbon atoms containing alkyl groups can be used as corrosion inhibitors in aqueous systems and have a comparatively excellent effectiveness. In addition, the compounds mentioned have only a low tendency to foam, sufficient solubility in water and are therefore particularly suitable for use as rust inhibitors in aqueous media.

Die Herstellung der verwendeten Verbindungen kann durch Umsetzung von Maleinsäureanhydrid mit C6- bis C18-Alkenen erfolgen- Dabei werden Alkenylbernsteinsäureanhydride erhalten, die mit Dialkylaminen mit jeweils 1 bis 10 Kohlenstoffatomen im Alkylrest im Molverhältnis 1 : 1 bei circa 70 bis 90°C zu den entsprechenden Halbamiden umgesetzt werden.The compounds used can be prepared by reacting maleic anhydride with C 6 -C 18 -alkenes. Alkenylsuccinic anhydrides are obtained, which are added with dialkylamines each having 1 to 10 carbon atoms in the alkyl radical in a molar ratio of 1: 1 at about 70 to 90 ° C. the corresponding half amides are implemented.

Die zur Anwendung gelangenden Salze der Halbamide werden durch Zugabe von äquimolaren beziehungsweise überschüssigen Mengen Alkanolaminen hergestellt. Zweckmäßigerweise kommen C2-bis C4-Alkanolamine, vorzugsweise Mono-, Di- oder Triethanolamine, in Betracht.The salts of the half-amides used are prepared by adding equimolar or excess amounts of alkanolamines. C 2 -C 4 -alkanolamines, preferably mono-, di- or triethanolamines, are expediently suitable.

Insbesondere werden auch die Verbindungen verwendet, die gemäß Formel I und II einen Alkenylrest R mit 10 bis 18 Kohlenstoffatomen und in der Amidgruppe Alkylrest R'bzw. R" mit 3 bis 8 Kohlenstoffatomen enthalten.In particular, the compounds are used which have an alkenyl radical R having 10 to 18 carbon atoms and in the amide group alkyl radical R'bzw according to formulas I and II. R "with 3 to 8 carbon atoms.

Zur Herstellung der Vorstufen Alkenylbernsteinsäureanhydrid können alle marktgängigen Olefine eingesetzt werden.α-Olefine, Olefine mit innenständiger Doppelbindung sowie Olefingemischen, die auch Vinylidenolefine enthalten, d. h.oL -Olefine mit zwei Substituenten am ß-C-Atom. Die Umsetzung mit den Aminen erfolgt in äquimolaren Verhältnissen oder auch mit geringem Überschuß an Anhydrid- Die Dialkylamine können geradkettig oder verzweigt sein.All commercially available olefins can be used to prepare the precursors alkenylsuccinic anhydride. Α-olefins, olefins with an internal double bond and olefin mixtures which also contain vinylidene olefins, i.e. h.oL olefins with two substituents on the ß-C atom. The reaction with the amines is carried out in equimolar proportions or with a slight excess of anhydride. The dialkylamines can be straight-chain or branched.

Die so herstellbaren Verbindungen eignen sich allein oder in Kombinationen mit anderen Stoffen als wasserlösliche antikorrosive Bestandteile in Rostschutzmitteln, technischen Reingigungsmitteln der Metallbearbeitung sowie in Kühlschmierstoffen.The compounds that can be produced in this way are suitable alone or in combinations with other substances as water-soluble anticorrosive constituents in rust inhibitors, technical cleaning agents in metalworking and in cooling lubricants.

Die erfindungsgemäßen Mittel kommen in Konzentrationen von 0,01 bis 15 Gewichtsprozent, vorzugsweise von 0,05 bis 1,0 Gewichtsprozent, jeweils berechnet als Alkenylbernsteinsäurehalbamid, zur Anwendung.The agents according to the invention are used in concentrations of 0.01 to 15 percent by weight, preferably 0.05 to 1.0 percent by weight, each calculated as alkenylsuccinic acid halamide.

Der Anmeldungsgegenstand wird durch die nachfolgenden Beispiele erläutert, ohne daß er hierauf beschränkt ist.The subject of the application is illustrated by the following examples, without being restricted thereto.

Beispiel 1example 1 HerstellungManufacturing

852 g (8,7 Mol) Maleinsäureanhydrid und 1830g (10,9 Mol) 1-Dodecen werden in Gegenwart von 9,1 g 2,6 Di-tert-butyl-4-methylphenol zunächst auf Rückfluß und anschließend so lange weiter erhitzt, bis eine Temperatur von circa 230 °C erreicht wird. Es wird circa 2 Stunden bei 230 °C nachgerührt, abgekühlt, das überschüssige Olefin im Vakuum abdestilliert und das als Rückstand verbleibende Dodecenylbernsteinsäureanhydrid durch Filtration von polymeren Partikeln befreit. Ausbeute: 1829 g (70 % der Theorie), Verseifungszahl 430.852 g (8.7 mol) of maleic anhydride and 1830 g (10.9 mol) of 1-dodecene are first heated to reflux in the presence of 9.1 g of 2,6-di-tert-butyl-4-methylphenol and then further heated until until a temperature of around 230 ° C is reached. The mixture is stirred for about 2 hours at 230 ° C., cooled, the excess olefin is distilled off in vacuo and the dodecenylsuccinic anhydride remaining as residue is freed from polymer particles by filtration. Yield: 1829 g (70% of theory), saponification number 430.

236 g (0,9 Mol nach Verseifungszahl) Lodecenylbernsteinsäureanhydrid werden unter N2-Atmosphäre auf 50 °C aufgewärmt und mit 116 g (0,9 Mol) Dibutylamin versetzt, wobei die Temperatur bis auf ca. 90 °C antsteigen kann. Nach beendeter Zugabe wird noch circa 1 Stunde bei 100 °C nachgerührt. Nach Abkühlung erhält man Dodecenylbernsteinsäure-mono-dibutylamid als eine klare, hochviskose Substanz. Ausbeute: 352 g (quantitativ), Säurezahl = 148 (Theorie: 143).236 g (0.9 mol according to the saponification number) of lodecenylsuccinic anhydride are warmed to 50 ° C. under an N 2 atmosphere and 116 g (0.9 mol) of dibutylamine are added, the temperature rising to about 90 ° C. After the addition is complete, stirring is continued at 100 ° C. for about 1 hour. After cooling, dodecenylsuccinic acid monodibutylamide is obtained as a clear, highly viscous substance. Yield: 352 g (quantitative), acid number = 148 (theory: 143).

Durch leichtes Erwärmen mit überschüssigem Mono-, Di- beziehungsweise Triethanolamin in Gegenwart von etwas wasser wird das Halbamid in die Alkanolamin-Salze überführt.The half amide is converted into the alkanolamine salts by gentle heating with excess mono-, di- or triethanolamine in the presence of a little water.

Beispiel 2Example 2

Auf analoge Weise wie die im Beispiel 1 beschriebene Herstellung von Dodecenylbernsteinsäure-mono-dibutylamid (laufende Nummer 2) werden die nachstehend genannten Bernsteinsäurehalbamide beziehungsweise deren Alkanolaminsalze dargestellt:

  • 1. Decenylbernsteinsäure-mono-diisopropylamid
  • 2. Dodecenylbernsteinsäure-mono-dibutylanid
  • 3. C14/16 -Alkenylbernsteinsäure-mono-dibutylamid
  • 4. C14/16 -Alkenylbernsteinsäure mono dipropylamid
  • 5- C14/16 -Alkenylbernsteinsäure-mono-di(2-ethylhexyl)amid
  • 6. Hexadecenylbernsteinsäure-mono-dibutilamid
  • 7. Isomer-C15/18 -alkenylbernsteinsäure-mono-dibutylamid
  • Ausgangsbasis α-C14/16-Olefine mit ca. 19% Vinylidenolefine
  • Olefin(gemisch) mit innenständiger Doppelbindung
The succinic acid halamides mentioned below and their alkanolamine salts are prepared in an analogous manner to the preparation of dodecenylsuccinic acid monodibutylamide (sequence number 2) described in Example 1:
  • 1. Decenylsuccinic acid monodisopropylamide
  • 2. Dodecenylsuccinic acid monodibutylanide
  • 3. C 14/16 alkenylsuccinic acid monodibutylamide
  • 4. C 14/16 alkenyl succinic acid mono dipropylamide
  • 5- C 14/16 alkenylsuccinic acid mono-di (2-ethylhexyl) amide
  • 6. Hexadecenylsuccinic acid monodibutilamide
  • 7. Isomer C 15/18 alkenyl succinic acid monodibutylamide
  • Starting point α-C 14/16 olefins with approx. 19% vinylidene olefins
  • Olefin (mixture) with internal double bond

Beispiel 3Example 3 Anwendungstechnische PrüfungApplication test

Die Prüfergebnisse sind den nachstehenden Tabellen zu entnehemn.The test results can be found in the tables below.

Die in den Beispielen 1 und 2 genannten Verbindungen wurden in Form der Mono-, Di- und Triethanolamin-Salze im Grauguß Filtertest nach DIN 51360 geprüft. Als Testmedium wurde Wasser mit einer Härte von 20°d entsprechend obiger DIN-ANweisung verwendet. Innerhalb der zu vergleichenden Testreihen wurde jeweils bei konstanten pH-Werten (8,0 bis 9,5) geprüft.The compounds mentioned in Examples 1 and 2 were tested in the form of the mono-, di- and triethanolamine salts in a gray cast iron filter test in accordance with DIN 51360. Water with a hardness of 20 ° d according to the above DIN instructions was used as the test medium. Within the test series to be compared, testing was carried out at constant pH values (8.0 to 9.5).

Die Bewertung erfolgte gemäß DIN 51360 unter Verwendung folgender Korrosionsgrade:

Figure imgb0003
Figure imgb0004
Figure imgb0005
Figure imgb0006
Figure imgb0007
 The evaluation was carried out in accordance with DIN 51360 using the following degrees of corrosion:
Figure imgb0003
Figure imgb0004
Figure imgb0005
Figure imgb0006
Figure imgb0007

Die Prüfungsergebnisse sind in der Tabelle wiedergegeben.

Figure imgb0008
Figure imgb0009
 The test results are shown in the table.
Figure imgb0008
Figure imgb0009

Claims (4)

1. Verwendung von Alkanolaminsalzen von Alkenylbernsteinsäurehalbamiden der allgemeinen Formeln I und II
Figure imgb0010
Figure imgb0011
wobei R einen Alkenylrest mit 6 bis 18 Kohlensteffatomen und R' und R" 1 bis 10 Kohlenstoffatome enthaltende Alkylgruppen darstellen als Korrosionsinhibitoren in wäßrigen Systemen.1. Use of alkanolamine salts of alkenylsuccinic acid halamides of the general formulas I and II
Figure imgb0010
Figure imgb0011
 where R is an alkenyl radical having 6 to 18 carbon atoms and R 'and R "are alkyl groups containing 1 to 10 carbon atoms as corrosion inhibitors in aqueous systems. 2. Verwendung gemäß Anspruch 1 in Konzentrationen von 0,01 bis 15 Gewichtsprozent, vorzugsweise von 0,05 bis 1 Gewichtsprozent.2. Use according to claim 1 in concentrations of 0.01 to 15 percent by weight, preferably from 0.05 to 1 percent by weight. 3. Verwendung gemäß Anspruch 1 und 2, wobei die Alkanolaminsalze Mono-, Di- und Triethanolaminsalze sind.3. Use according to claim 1 and 2, wherein the alkanolamine salts are mono-, di- and triethanolamine salts. 4- Verwendung gemäß Anspruch 1 bis 3, wobei gemäß Formeln I und II der Alkenylrest R 10 bis 18 Kohlenstoffatome und die Alkylreste R'und R" jeweils 3 bis 8 Kohlenstoffatome enthalten.4- Use according to claims 1 to 3, wherein according to formulas I and II the alkenyl radical R contains 10 to 18 carbon atoms and the alkyl radicals R 'and R "each contain 3 to 8 carbon atoms.
EP84113211A 1983-11-12 1984-11-02 Succinic monodialkyl amides as water-soluble corrosion inhibitors Expired EP0144738B1 (en)

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AT84113211T ATE35559T1 (en) 1983-11-12 1984-11-02 Succinic Mono-Dialkylamides As Water-Soluble Anticorrosive Agents.

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DE3341013 1983-11-12
DE19833341013 DE3341013A1 (en) 1983-11-12 1983-11-12 AMBER ACID MONO-DIALKYLAMIDES AS WATER-SOLUBLE CORROSION PROTECTORS

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EP0216280A2 (en) * 1985-09-27 1987-04-01 Hoechst Aktiengesellschaft Use of alkenylsuccinic monoamides as corrosion inhibitors
EP0359048A2 (en) * 1988-09-03 1990-03-21 Hoechst Aktiengesellschaft Amidoamine salts of alkenylsuccinic acid derivatives, method for their preparation and their use as corrosion inhibitors
EP0501368A1 (en) * 1991-02-26 1992-09-02 Hoechst Aktiengesellschaft Use of alkenylsuccinic acid half-amides
EP0584711A1 (en) * 1992-08-22 1994-03-02 Hoechst Aktiengesellschaft Alkenyl succinic acid derivatives as metal working agents

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JP5315551B2 (en) * 2007-01-10 2013-10-16 キレスト株式会社 Rust preventive
JP2009001879A (en) * 2007-06-22 2009-01-08 Sanyo Chem Ind Ltd Rust and/or corrosion preventive for copper

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Title
CHEMICAL ABSTRACTS, Band 97, Nr. 69. August 1982, Seite 217, Nr. 42468s, COLUMBUS, OHIO, (US). *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0216280A2 (en) * 1985-09-27 1987-04-01 Hoechst Aktiengesellschaft Use of alkenylsuccinic monoamides as corrosion inhibitors
EP0216280A3 (en) * 1985-09-27 1987-12-09 Hoechst Aktiengesellschaft Use of alkenylsuccinic monoamides as corrosion inhibitors
EP0359048A2 (en) * 1988-09-03 1990-03-21 Hoechst Aktiengesellschaft Amidoamine salts of alkenylsuccinic acid derivatives, method for their preparation and their use as corrosion inhibitors
EP0359048A3 (en) * 1988-09-03 1991-10-23 Hoechst Aktiengesellschaft Amidoamine salts of alkenylsuccinic acid derivatives, method for their preparation and their use as corrosion inhibitors
EP0501368A1 (en) * 1991-02-26 1992-09-02 Hoechst Aktiengesellschaft Use of alkenylsuccinic acid half-amides
EP0584711A1 (en) * 1992-08-22 1994-03-02 Hoechst Aktiengesellschaft Alkenyl succinic acid derivatives as metal working agents

Also Published As

Publication number Publication date
DE3472576D1 (en) 1988-08-11
AU3527684A (en) 1985-05-30
ZA848786B (en) 1985-06-26
ATE35559T1 (en) 1988-07-15
JPS60116791A (en) 1985-06-24
EP0144738B1 (en) 1988-07-06
US4705666A (en) 1987-11-10
DE3341013A1 (en) 1985-05-23
CA1259630A (en) 1989-09-19
AU565084B2 (en) 1987-09-03

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