NO157334B - Organofilt leireglmiddel, fremgangsmaate for fremstilling derav og anvendelse derav. - Google Patents

Organofilt leireglmiddel, fremgangsmaate for fremstilling derav og anvendelse derav. Download PDF

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NO157334B
NO157334B NO820662A NO820662A NO157334B NO 157334 B NO157334 B NO 157334B NO 820662 A NO820662 A NO 820662A NO 820662 A NO820662 A NO 820662A NO 157334 B NO157334 B NO 157334B
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Wilbur S Mardis
Claude Malcolm Finlayson
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Nl Chemicals Inc
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    • CCHEMISTRY; METALLURGY
    • C01INORGANIC CHEMISTRY
    • C01BNON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
    • C01B33/00Silicon; Compounds thereof
    • C01B33/20Silicates
    • C01B33/36Silicates having base-exchange properties but not having molecular sieve properties
    • C01B33/38Layered base-exchange silicates, e.g. clays, micas or alkali metal silicates of kenyaite or magadiite type
    • C01B33/44Products obtained from layered base-exchange silicates by ion-exchange with organic compounds such as ammonium, phosphonium or sulfonium compounds or by intercalation of organic compounds, e.g. organoclay material
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D7/00Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40Additives
    • C09D7/43Thickening agents
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K8/00Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
    • C09K8/02Well-drilling compositions
    • C09K8/32Non-aqueous well-drilling compositions, e.g. oil-based
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M113/00Lubricating compositions characterised by the thickening agent being an inorganic material
    • C10M113/16Inorganic material treated with organic compounds, e.g. coated
    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08KUse of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00Use of inorganic substances as compounding ingredients
    • C08K3/34Silicon-containing compounds
    • C08K3/346Clay
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2201/00Inorganic compounds or elements as ingredients in lubricant compositions
    • C10M2201/14Inorganic compounds or elements as ingredients in lubricant compositions inorganic compounds surface treated with organic compounds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2215/02Amines, e.g. polyalkylene polyamines; Quaternary amines
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/042Sulfate esters
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/04Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions containing sulfur-to-oxygen bonds, i.e. sulfones, sulfoxides
    • C10M2219/044Sulfonic acids, Derivatives thereof, e.g. neutral salts
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10MLUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C10M2223/061Metal salts
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S507/00Earth boring, well treating, and oil field chemistry
    • Y10S507/901Organically modified inorganic solid
    • YGENERAL 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
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S507/00Earth boring, well treating, and oil field chemistry
    • Y10S507/926Packer fluid

Description

Fremgangsmåte til fremstilling av blandingsestere
som tjener som emulgatorer.
Oppfinnelsen vedrører en fremgangsmåte til fremstilling av som emulgatorer tjenende blandingsestere som spesielt er anvendbar ved fremstilling av nærings- og forstoffer.
Fremgangsmåten ifølge oppfinnelsen er karakterisert ved at man forestrer en i nærings- eller forstoffer fysiologisk tålbar organisk eller uorganisk flerbasisk syre ved en sur gruppe med en delester av en flerverdig alkohol med en fettsyre med 12 til 24 karbonatomer og ved en annen aur gruppe med en delester av en flerverdig alkohol med en karboksylsyre med 2 til 12 karbonatomer.
Det har vist seg fordelaktig at det som organisk syre med
2 til 12 C-atomer anvendes en oksysyre.
Som flerbasisk uorganisk syre egner det seg f.eks. orto-eller pyrofosforsyre,som organisk syre f.eks. sitronsyre, aconitsyre og trikarballylsyre, vinsyre, eplesyre, ravsyre, adipinsyre.
I mange tilfeller er det hensiktsmessig med en ikke for sur reaksjon av emulgatoren som er fremstilt ifolge oppfinnelsen. Da kan ved anvendelse av en minst trebasisk syre som utgangsprodukt for emulgatoren den uforestrede syregruppe eller -grupper etter forestringen ifolge oppfinnelsen den andre karboksylgruppen nøytraliseres med en base. Herved kan man f.eks. ved anvendelse av emulgatoren fra eksempel 1 til emulsjonsfremstilling opplose den sure ester i olje-fase og deretter tilsette til vannfasen et alkalisk reagerende stoff i en mengde som er ekvivalent med emulgatorens syretall. Ved sammen-blanding av de to faser får man en emulsjon med omtrent nSytral pH-verdi.
Emulgatorene fremstilt ifolge oppfinnelsen har vist seg som spesielt hensiktsmessig tilsetningsmiddel for deig for forbedring av deres bakeevne og ved tilsetning av emulgatoren fremstilt ifolge oppfinnelsen okes finportheten og bakevolum.
Videre er det mulig eksempelvis ved hjelp av ifolge oppfinnelsen fremstilte emulgatorer å fremstille selvemulgerende oljer som fortrinnsvis er meget interessante for formiddelfremstilling for-di man f.eks. ved hjelp av en slik tilsetning til soyaolje kan gjore denne selvemulgerende i mager melk.
Eksempel 1
400 vektdeler 90%-ig glycerinmonostearat oppvarmes med 192 vektdeler sitronsyre i ca. 1/2 time ved 130°C. Reaksjonsproduktet har et syretall på ca. 200 og oppvarmes deretter med 134 vektdeler glycerinmonoacetat i 1 3/4 time likeledes ved 130°C. Det myke vokslignende sluttprodukt har et syretall på 83. Utbytte 92 vektprosent av utgangsstoffet.
I sluttproduktet er en karboksylgruppe av sitronsyren for-estret med en primær hydroksylgruppe av glycerinmonostearatet og den annen karboksylgruppe med den primære hydroksylgruppe av glycerin-monoacetatet, mens den tredje karboksylgruppen av sitronsyren er bi-beholdt uforandret.
Eksempel 2
400 vektdeler 90$-ig glycerinmonostearat forestrés med 192 vektdeler sitronsyre som i eksempel 1 til et produkt med et syretall på 200 og oppvarmes deretter med 175 vektdeler glycerindiacetat i 2 timer ved 130°C. Det myke vokslignende sluttprodukt har et syretall fra 70 til 72. Utbytte: 92 til 93 vektprosent, referert til utgangsprodukt et.
Eksempel 3
Istedenfor glycerinmonostearat ifolge eksempel 1 anvendes
en blanding av partielle estere som ble fremstilt ved omforestring av storfetalg med glycerin. 400 vektdeler av denne blanding om-settes med 192 vektdeler sitronsyre og 135 vektdeler glycerinmonoacetat. Sluttproduktets syretall 82.
Utbytte: 92 vektprosent. Produktet er en seigtflytende halv-krystallinsk masse.
Eksempel 4
400 vektdeler smeltet S0%- ±g glycerinmonostearat blandes med en opplosning av 174 vektdeler akonitsyre i samme vektmengde vann umiddelbart for innlop i en tynnsjiktsfordamper som holdes under et vakuum på 600 mm Hg. Gjennomstromningshastigheten gjennom fordamperen reguleres således at reaksjonsproduktet forlater den med en temperatur på 130<0-> 135°c og et syretall på omtrent 200, nemlig en mengde på 556 vektdeler.
556 vektdeler av det således fremstilte fargelose voksaktige produkt videreoppvarmes med 134 vektdeler glycerinmonoacetat så lenge ved 130°C inntil syretallet er fallt til 8O-85. Sluttproduktet er en lysfarget og svakt plastisk vokslignende masse.
Utbytte: 670 vektdeler.
Eksempel 5
400 vektdeler S0%- ±g glycerinmonoester av smeltfettsyrer om-settes med en opplosning av 176 vektdeler trikarballylsyre i omtrent den dobbelte vannmengde i en tynnsjiktfordamper til et syretall av reaksjonsproduktet på omtrent 200.
Utbytte: 558 vektdeler av et omtrent fargelost vokslignende produkt.
558 vektdeler av den dannede ester videreoppvarmes med 176 vektdeler glycerindiacetat ved 130°-135°C inntil sluttproduktets syretall er fallt til 75-80. Produktet er av vaselinaktig konsistens.
Utbytte: 715 vektdeler = 95 vektprosent av utgangsmaterialet. Eksempel 6
400 vektdeler 90#-ig glycerinmonostearat oppvarmes med 134 vektdeler eplesyre ved 130°C og oppvarmningen fortsetter så lenge inntil reaksjonsproduktets syretall er fallt til omtrent 105-110, (omtrent 1 time). Deretter blandes reaksjonsproduktet med 134 vektdeler glycerinmonoacetat og oppvarmningen fortsetter inntil syretallet er fallt til 25-30* Sluttproduktet er en svakt gulaktig vokslignende masse, som er opploselig varmt i triglycerider. ;Utbytte 63O vektdeler = 94 vektprosent av utgangsmaterialet. Eksempel 7 80 vektdeler 90%-ig glycerinmonostearat oppvarmes med 20 vektdeler ravsyreanhydrid ved 120°C og oppvarmningen fortsetter l/2 time idet syretallet faller til IIO-II5. Til reaksjonsblandingen settes 35 deler glycerindiacetat og oppvarmningen fortsetter i 2 timer idet syretallet faller til 25-30. ;Utbytte: 130 deler av en svakt gulaktig vokslignende masse ;= 96 vektprosent av utgangsmaterialet. ;E ksempel 8 ;Til 400 vektdeler glycerinmonostearat settes 44 vektdeler fosforpentoksyd og blandingen oppvarmes il/2 time ved 120°C. Det herved dannede ovre sjikt adskilles fra den mindre nedre harpiks-lignende fase og etter ytterligere oppvarmning ved 70°C blandes med 11% fosforpertoksyd beregnet på væskens vekt. Herved inntrer en ekso-term reaksjon og temperaturen stiger til 100°C. Etter avkjOling til 70°C adskilles den ovre fase igjen fra den mindre bunnfase. ;Utbytte: ca. 43O vektdeler. ;430 vektdeler av den dannede monostearinglycerinfosforsyre-ester blandes med 176 vektdeler glycerindiacetat og oppvarmes under omroring i 20 minutter ved 100°C idet syretallet Siler til 90-95• Sluttproduktet (588 vektdeler) er en lys voks som i vann gir en kolloidal opplosning med sterkt sur reaksjon og er opplSselig i tri-glyceridoljer. ;Eksempel 9 ;400 vektdeler 90$-ig glycerinmonostearat oppvarmes med 146 vektdeler adipinsyre ved 130°C inntil syretallet er fallt til 105-110. Til dette reaksjon^produkt settes 134 vektdeler glycerinmonoacetat ;og oppvarmningen fortsettes inntil syretallet er fallt til 25-30. ;Utbytte: 642 vektdeler av en omtrent hvit vokslignende masse, hvilket tilsvarer 94 vektprosent av utgangsmaterialet. ;Eksempel 10 ;Ved anvendelse av en minst trebasisk karbonsyre som utgangsprodukt opploser man hensiktsmessig det sure esterprodukt i oljefasen og tilsetter til vannfasen en ekvivalent mengde alkali. Ved sammen-blanding av de to faser får man en nSytral emulsjon. ;Man kan imidlertid ved noytralisering av den sure gruppe på forhånd fremstille saltet, f.eks.: 100 vektdeler av sluttproduktet if5lge eksempel 1 blandes umiddelbart før innløp i en tynnsjiktsfordamper kontinuerlig med en oppløsning av 5>9 vektdeler natriumhyriroksyd i den dobbelte vannmengde. Gjennomstrømningshastighet, temperatur og vakuum reguleres således ;at vannet fordamper og reaksjonsproduktet forlater fordamperen med en temperatur på ca. 105°C. Sluttproduktet stivner til en hård, omtrent hvit masse som lett lar seg pulverisere og løser seg opp i vann. Reaksjonsproduktet kan, hvis ønsket, innstilles til svakt alkalisk eller svakt reaksjon ved valg av den riktige alkalimengde i forhold til esterens syretall. ;Eksempel 11. ;Glyserin kondenseres ved oppvarmning med små mengder natriumhydroksyd under karbondioksyd til 240°C til et kondensasjons-produkt som vesentlig inneholder di- ogtriglyserin. ;400- vektdeler av det dannede polyglyserin forestres ved oppvarmning til 240°C under vakuum i 3-4 timer med 600 vektdeler stearinsyre. Etter avkjøling vaskes med vann til pH ca. 5 til fjerning av uforestret polyglyserin og deretter tørkes. ;770 vektdeler av den vaskede ester blandes med 230 vektdeler sitronsyremonohydrat og blandingen oppvarmes under oppvarmning ved 150°C, inntil syretallet er falt til omtrent 80. Etter tilsetning av 130 g monoacetin videreforestres inntil syretallet er falt til 35-40. Produktet<*>er en myk voksaktig masse.
Eksempel 12.
Sorbitanmonostearat fremstilles i den kjente fremgangsmåte ved høytemperaturforestring av sorbitol med en blanding av stearin-og palmitinsyre. Produktet vaskes med vann til pH ca. 5 til fjerning av uforestret polyalkohol og tørkes deretter.
1000 g av dette produkt blandes med 420 g sitronsyremonohydrat og oppvarmes under omrøring ved 140-150°C inntil syretallet er falt til 160-65. Etter tjilsetning av 270 g monoacetin blir det videreforestret inntil syretallet er falt til omtrent 70-75. Produktet er en svakt brunaktig, myk, vokslignende masse.

Claims (4)

1. Fremgangsmåte til fremstilling av som emulgatorer tjenende blandingsestere, karakterisert ved at man forestrer en i nærings- eller forstoffer fysiologisk tålbar organisk eller uorganisk flerbasisk syre ved en sur gruppe med en delester av en flerverdig alkohol med en fettsyre med 12 til 24 karbonatomer og ved en annen sur gruppe med en delester av en flerverdig alkohol med
en karboksylsyre med 2 til 12 karbonatomer.
2. Fremgangsmåte ifølge krav 1, karakterisert ved at man som flerbasisk uorganisk syre anvender orto- eller pyrofosforsyre.
3. Fremgangsmåte ifølge krav 1 eller 2, karakterisert ved at man som syrekomponent for annen delester anvender en oksykarboksylsyre med 2 til 12 karbonatomer.
4. Fremgangsmåte ifølge krav 1 til 3»karakterisert ved at man ved anvendelse av en minst trebasisk syre nøytraliserer den fri syregruppe med en base etter forestringen av de to andre sure grupper.
NO820662A 1982-02-18 1982-03-03 Organofilt leireglmiddel, fremgangsmaate for fremstilling derav og anvendelse derav. NO157334C (no)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US06/348,641 US4517112A (en) 1982-02-18 1982-02-18 Modified organophilic clay complexes, their preparation and non-aqueous systems containing them

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NO820662L NO820662L (no) 1983-08-19
NO157334B true NO157334B (no) 1987-11-23
NO157334C NO157334C (no) 1988-03-02

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JP (1) JPS58153534A (no)
AU (1) AU551910B2 (no)
BE (1) BE892779A (no)
BR (1) BR8202246A (no)
CA (1) CA1179571A (no)
CH (2) CH655736A5 (no)
DE (1) DE3208052A1 (no)
DK (1) DK90482A (no)
FI (1) FI75101C (no)
FR (1) FR2521580B1 (no)
GB (1) GB2116157B (no)
GR (1) GR76110B (no)
IE (1) IE53365B1 (no)
IT (1) IT1151109B (no)
LU (1) LU84076A1 (no)
MX (2) MX172269B (no)
NL (1) NL187433C (no)
NO (1) NO157334C (no)
SE (1) SE455303B (no)
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CH655736A5 (de) 1986-05-15
JPS58153534A (ja) 1983-09-12
CA1179571A (en) 1984-12-18
AU551910B2 (en) 1986-05-15
IT8220357A0 (it) 1982-03-24
FI75101C (fi) 1988-05-09
BR8202246A (pt) 1983-11-22
NL187433C (nl) 1991-10-01
SE8201380L (sv) 1983-08-19
IT1151109B (it) 1986-12-17
IT8220357A1 (it) 1983-09-24
NL187433B (nl) 1991-05-01
DE3208052A1 (de) 1983-08-18
FR2521580B1 (fr) 1985-07-12
MX160755A (es) 1990-05-09
MX172269B (es) 1993-12-09
CH655511B (no) 1986-04-30
IE820468L (en) 1982-08-18
DE3208052C2 (no) 1993-09-09
JPH0357948B2 (no) 1991-09-03
SE455303B (sv) 1988-07-04
FI820750L (fi) 1983-08-19
NL8201038A (nl) 1983-09-16
NO820662L (no) 1983-08-19
GB2116157A (en) 1983-09-21
DK90482A (da) 1983-08-19
BE892779A (fr) 1982-08-02
NO157334C (no) 1988-03-02
GB2116157B (en) 1985-09-04
ZA821507B (en) 1983-01-26
LU84076A1 (fr) 1982-09-13
FI75101B (fi) 1988-01-29
AU8111882A (en) 1983-08-25
GR76110B (no) 1984-08-03
FR2521580A1 (fr) 1983-08-19
US4517112A (en) 1985-05-14
IE53365B1 (en) 1988-10-26

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