NO173663B - PROCEDURE FOR THE PREPARATION OF LACTULOSE BY EPIMERIZATION OF LACTOSE IN Aqueous SOLUTION IN THE PRESENTS OF SODIUM ALUMINATE - Google Patents
PROCEDURE FOR THE PREPARATION OF LACTULOSE BY EPIMERIZATION OF LACTOSE IN Aqueous SOLUTION IN THE PRESENTS OF SODIUM ALUMINATE Download PDFInfo
- Publication number
- NO173663B NO173663B NO89892105A NO892105A NO173663B NO 173663 B NO173663 B NO 173663B NO 89892105 A NO89892105 A NO 89892105A NO 892105 A NO892105 A NO 892105A NO 173663 B NO173663 B NO 173663B
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- Prior art keywords
- solution
- lactulose
- carried out
- sodium aluminate
- lactose
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- 238000000034 method Methods 0.000 title claims description 23
- 229960000511 lactulose Drugs 0.000 title claims description 20
- PFCRQPBOOFTZGQ-UHFFFAOYSA-N lactulose keto form Natural products OCC(=O)C(O)C(C(O)CO)OC1OC(CO)C(O)C(O)C1O PFCRQPBOOFTZGQ-UHFFFAOYSA-N 0.000 title claims description 20
- JCQLYHFGKNRPGE-FCVZTGTOSA-N lactulose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 JCQLYHFGKNRPGE-FCVZTGTOSA-N 0.000 title claims description 19
- ANBBXQWFNXMHLD-UHFFFAOYSA-N aluminum;sodium;oxygen(2-) Chemical compound [O-2].[O-2].[Na+].[Al+3] ANBBXQWFNXMHLD-UHFFFAOYSA-N 0.000 title claims description 14
- 229910001388 sodium aluminate Inorganic materials 0.000 title claims description 14
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 title claims description 12
- 239000008101 lactose Substances 0.000 title claims description 12
- 238000006345 epimerization reaction Methods 0.000 title claims description 8
- 239000007864 aqueous solution Substances 0.000 title claims description 4
- 239000000243 solution Substances 0.000 claims description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims description 13
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 238000006386 neutralization reaction Methods 0.000 claims description 10
- 238000000108 ultra-filtration Methods 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000003456 ion exchange resin Substances 0.000 claims description 5
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 230000001105 regulatory effect Effects 0.000 claims description 4
- 238000001471 micro-filtration Methods 0.000 claims description 3
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 claims 1
- 238000001354 calcination Methods 0.000 claims 1
- 235000011149 sulphuric acid Nutrition 0.000 claims 1
- 239000006188 syrup Substances 0.000 description 4
- 235000020357 syrup Nutrition 0.000 description 4
- 238000010908 decantation Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 150000002016 disaccharides Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229930182830 galactose Natural products 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000015872 dietary supplement Nutrition 0.000 description 1
- UQGFMSUEHSUPRD-UHFFFAOYSA-N disodium;3,7-dioxido-2,4,6,8,9-pentaoxa-1,3,5,7-tetraborabicyclo[3.3.1]nonane Chemical compound [Na+].[Na+].O1B([O-])OB2OB([O-])OB1O2 UQGFMSUEHSUPRD-UHFFFAOYSA-N 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 208000028774 intestinal disease Diseases 0.000 description 1
- 150000002681 magnesium compounds Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
Landscapes
- Medicinal Preparation (AREA)
- Saccharide Compounds (AREA)
Description
Oppfinnelsen vedrører en fremgangsmåte for fremstilling av laktulose ved epimerisering av laktose i vandig oppløsning i nærvær av natriumaluminat, som kan gjennomføres i en indu-striell målestokk. The invention relates to a method for the production of lactulose by epimerization of lactose in aqueous solution in the presence of sodium aluminate, which can be carried out on an industrial scale.
Laktulose er et syntetisk disaccharid som for tiden anvendes i syrupform for behandling av tarmlidelser, og i krystallinsk form som en søtningsmiddelerstatning for saccharin. Den brukes også som matvaretilskudd i pediatriske og geria-triske dietter. Lactulose is a synthetic disaccharide that is currently used in syrup form for the treatment of intestinal disorders, and in crystalline form as a sweetener substitute for saccharin. It is also used as a food supplement in pediatric and geriatric diets.
Det er kjent mange fremgangsmåter for fremstilling av laktulose som er et lett tilgjengelig naturlig disaccharid. Many methods are known for the production of lactulose, which is an easily available natural disaccharide.
Noen av disse fremgangsmåtene er basert hovedsakelig på epimeriseringen av laktose ved hjelp av sterke alkalier som f.eks. CafOH^/ NaOH og KOH, og sterke organiske baser. Some of these methods are based mainly on the epimerization of lactose by means of strong alkalis such as e.g. CafOH^/ NaOH and KOH, and strong organic bases.
Disse fremgangsmåténe har den ulempe at de fører til dannelse av en betydelig prosentandel vanskelig fraskill-bare, fargede biprodukter som sterkt reduserer laktuloseut-byttet og gjør det vanskelig både å bruke laktulosen i syrupformen og å fremstille den som et krystallinsk produkt. These methods have the disadvantage that they lead to the formation of a significant percentage of hard-to-separate, colored by-products which greatly reduce the lactulose yield and make it difficult both to use the lactulose in syrup form and to produce it as a crystalline product.
Ved en annen gruppe fremgangsmåter anvendes natrium-tetraborat og natriumalbinat som epimeriseringsmidler. In another group of methods, sodium tetraborate and sodium albinate are used as epimerizing agents.
Selv om disse fremgangsmåtene gir et høyere laktulcse-utbytte og et renere produkt, er de utilfredsstillende ut fra det industrielle aspekt, både på grunn av vanskeligheten med å filtrere bort aluminiumhydroxydet og på grunn av vanskeligheten med å fjerne borsyren kvantitativt. Although these methods give a higher lactulcse yield and a cleaner product, they are unsatisfactory from an industrial point of view, both because of the difficulty of filtering out the aluminum hydroxide and because of the difficulty of quantitatively removing the boric acid.
Andre fremgangsmåter hvor det anvendes sterkt alkalisk ionebytterharpikser for epimeriseringen, er for kostbare og gjør det ikke mulig å produsere laktulose til markedspriser. Other methods where strongly alkaline ion exchange resins are used for the epimerization are too expensive and do not make it possible to produce lactulose at market prices.
Fremgangsmåter for laktuloseepimerisering ved hjelp av magnesiumforbindelser er også kjent. Methods for lactulose epimerization using magnesium compounds are also known.
Disse fremgangsmåtene har ulempen ved at de krever svært These methods have the disadvantage that they are very demanding
store reaksjonsvolumer for å oppnå små mengder laktulose. large reaction volumes to obtain small amounts of lactulose.
Vi har nå oppfunnet en fremgangsmåte for fremstilling We have now invented a method of manufacture
av laktulose hvorved ulempene ved den kjente teknikk unngås. of lactulose, whereby the disadvantages of the known technique are avoided.
Nærmere bestemt har vi oppfunnet en fremgangsmåte som omfatter epimerisering av laktose med natriumaluminat, noe som gjør det mulig å frafiltrere aluminiumhydroxyd på en lettvint måte, og å utvinne natriumaluminatet på en lettvint måte for bruk i neste omgang. More specifically, we have invented a method that involves the epimerization of lactose with sodium aluminate, which makes it possible to easily filter out aluminum hydroxide, and to recover the sodium aluminate in an easy way for use in the next step.
Oppfinnelsen vedrører således en fremgangsmåte for fremstilling av laktulose ved epimerisering av laktose i vandig oppløsning i nærvær av natriumaluminat etterfulgt av nøytrali-sering av den vandige reaksjonsblanding med en vandig H2S04-oppløsning for å oppnå en pH-verdi mellom 4,5 og 8, fortrinnsvis mellom 6 og 7. The invention thus relates to a method for the production of lactulose by epimerization of lactose in aqueous solution in the presence of sodium aluminate followed by neutralization of the aqueous reaction mixture with an aqueous H 2 SO 4 solution to achieve a pH value between 4.5 and 8, preferably between 6 and 7.
Fremgangsmåten ifølge foreliggende oppfinnelse er kjennetegnet ved at: a) nøytraliseringen foretas kontinuerlig ved samtidig å føre blandingen og svovelsyreoppløsningen til en reaktor med en tilførselshastighet som er regulert for å oppnå den foran nevnte pH-verdi, b) aluminiumhydroxydet skilles fra den nøytraliserte blanding ved hjelp av et sentrifugedekanteringsapparat, c) oppløsningen erholdt i trinn b) underkastes ultrafiltrering eller mikrofiltrering, d) oppløsningen erholdt i trinn c) avioniseres ved hjelp av ionebytterharpikser, e) oppløsningen erholdt i trinn d) oppkonsentreres til en konsentrasjon på ca. 50 vekt% laktulose, f) det faste aluminiumhydroxyd erholdt i trinnene b) og The method according to the present invention is characterized by: a) the neutralization is carried out continuously by simultaneously feeding the mixture and the sulfuric acid solution to a reactor with a feed rate that is regulated to achieve the aforementioned pH value, b) the aluminum hydroxide is separated from the neutralized mixture using of a centrifuge decanter, c) the solution obtained in step b) is subjected to ultrafiltration or microfiltration, d) the solution obtained in step c) is deionized using ion exchange resins, e) the solution obtained in step d) is concentrated to a concentration of approx. 50% by weight lactulose, f) the solid aluminum hydroxide obtained in steps b) and
c) behandles med NaOH-oppløsning og c) treated with NaOH solution and
g) produktet fra trinn f) kalsineres, hvorved man får natriumaluminat som resirkuleres til reaksjons-trinnet. g) the product from step f) is calcined, whereby sodium aluminate is obtained which is recycled to the reaction step.
For å fremstille laktulose ved hjelp av fremgangsmåten ifølge foreliggende oppfinnelse fremstilles først en blanding av laktose og vann i et egnet blandeapparat under anvendelse av et vektforhold mellom vann og laktose på mellom 2:1 og 4:1. To produce lactulose using the method according to the present invention, a mixture of lactose and water is first prepared in a suitable mixing apparatus using a weight ratio between water and lactose of between 2:1 and 4:1.
Denne blandingen føres inn i en reaktor sammen med en This mixture is fed into a reactor together with a
35 - 45 vekt% natriumaluminatoppløsning, hvoretter massen homogeniseres ved omrøring og omsettes ved en temperatur mellom 50 og 70°C i et tidsrom mellom 30 og 60 minutter. 35 - 45% by weight sodium aluminate solution, after which the mass is homogenised by stirring and reacted at a temperature between 50 and 70°C for a period of between 30 and 60 minutes.
Natriumaluminatet brukes i et vektforhold til laktosen på mellom 0,3:1 og 1:1. The sodium aluminate is used in a weight ratio to the lactose of between 0.3:1 and 1:1.
Den erholdte oppløsning fra reaksjonen med natriumaluminat tilføres kontinuerlig samtidig med en svovelsyre-oppløsning med konsentrasjon mellom 1 og 5 N, til en nøytra-liseringsreaktor under anvendelse av slike tilførselshastig-heter som må til for å oppnå en oppholdstid mellom 20 og 60 minutter. Tilførselshastigheten reguleres slik at det fåes nøytralisering til den foran nevnte pH-verdi. The solution obtained from the reaction with sodium aluminate is fed continuously at the same time as a sulfuric acid solution with a concentration between 1 and 5 N to a neutralization reactor using such feed rates as are necessary to achieve a residence time of between 20 and 60 minutes. The supply rate is regulated so that neutralization is achieved to the aforementioned pH value.
I denne sammenheng har vi funnet at hvis det nøytraliseres til mindre enn pH 4,5, dannes det en gelatinaktig masse som er umulig å frafiltrere, mens dersom det nøytraliseres til mer enn pH 8, er utfellingen av aluminiumhydroxydet ufull-stendig. Ved å nøytralisere til pH 6 - 7 er bunnfall-karakteristikaene slik at suspensjon derav er tilstrekkelig flytende til å muliggjøre enkel filtrering. In this context, we have found that if it is neutralized to less than pH 4.5, a gelatinous mass is formed which is impossible to filter out, while if it is neutralized to more than pH 8, the precipitation of the aluminum hydroxide is incomplete. By neutralizing to pH 6 - 7, the sedimentation characteristics are such that suspension thereof is sufficiently fluid to enable easy filtration.
Suspensjonen som fås i nøytraliseringstrinnet, sepa-reres ved hjelp av sentrifugedekantering, hvorved det fås et fast stoff med et tørrstoffinnhold på ca. 30 vekt% og en væske som inneholder en liten mengde oppslemmet aluminiumhydroxyd. The suspension obtained in the neutralization step is separated by means of centrifuge decantation, whereby a solid is obtained with a dry matter content of approx. 30% by weight and a liquid containing a small amount of slurried aluminum hydroxide.
Denne væsken underkastes ultrafiltering eller mikrofiltrering for å fraskille det oppslemmede aluminiumhydroxyd. Det fås en fullstendig klar oppløsning som avionisere.s ved ionebytterharpikser ifølge kjente fremgangsmåter, hvoretter den oppkonsentreres til den påkrevde laktulosesyrup som har følgende vektsammensetning: This liquid is subjected to ultrafiltration or microfiltration to separate the suspended aluminum hydroxide. A completely clear solution is obtained which is deionized with ion exchange resins according to known methods, after which it is concentrated to the required lactulose syrup which has the following weight composition:
- laktulose: 45 - 55% - lactulose: 45 - 55%
- laktose: 1-3% - lactose: 1-3%
- galaktose: 2-6% - galactose: 2-6%
De faste stoffene fra sentrifugedekanterings- og ultrafiltreringstrinnene slås sammen, behandles med 48 vekt% natriumhydroxyd inntil pH 11 - 12 er nådd, og den erholdte blanding kalsineres ved 700 - 800°C for å brenne av de inne-holdte organiske forbindelser og utvinne natriumaluminatet, som resirkuleres til det første fremgangsmåtetrinn. The solids from the centrifuge decantation and ultrafiltration steps are combined, treated with 48% by weight sodium hydroxide until pH 11 - 12 is reached, and the resulting mixture is calcined at 700 - 800°C to burn off the contained organic compounds and extract the sodium aluminate, which is recycled to the first process step.
Eksemplet nedenunder er gjengitt for å illustrere oppfinnelsen nærmere. The example below is reproduced to illustrate the invention in more detail.
Eksempel 1 Example 1
1000 kg laktose ble blandet med 3000 kg vann og ført inn i en reaktor sammen med 1100 kg av en 40 vekt% natrium-aluminatoppløsning. 1000 kg of lactose was mixed with 3000 kg of water and fed into a reactor together with 1100 kg of a 40% by weight sodium aluminate solution.
Blandingen ble holdt under omrøring i 20 minutter, hvoretter den erholdte oppløsning ble pumpet gjennom en kontinuerlig reaktor ved en gjennomstrømningshastighet som gir en oppholdstid på 40 minutter, idet temperaturen ble holdt konstant ved 6 0°C. The mixture was kept under stirring for 20 minutes, after which the resulting solution was pumped through a continuous reactor at a flow rate giving a residence time of 40 minutes, the temperature being kept constant at 60°C.
Mens omsetningen fortsatte ble deretter oppløsningen ført kontinuerlig til en nøytraliseringsreaktor samtidig med at 4N svovelsyreoppløsning ble tilført den samme reaktor, idet gjennomstrømningshastighetene til de to oppløsningene ble regulert slik at det ble oppnådd en konstant pH på 6,5. While the reaction continued, the solution was then fed continuously to a neutralization reactor at the same time as 4N sulfuric acid solution was added to the same reactor, the flow rates of the two solutions being regulated so that a constant pH of 6.5 was achieved.
Det ble oppnådd en suspensjon som inneholdt 6,5 vekt% aluminiumhydroxyd og 12 vekt% laktulose. A suspension containing 6.5% by weight of aluminum hydroxide and 12% by weight of lactulose was obtained.
Mesteparten av aluminiumhydroxydet ble fraskilt i et sentrifugedekanteringsapparat, hvorved man fikk en opale-scerende oppløsning som inneholdt 0,7 vekt% aluminiumhydroxyd. Dette ble fjernet ved ultrafiltrering. Most of the aluminum hydroxide was separated in a centrifuge decanter, whereby an opalescent solution containing 0.7% by weight of aluminum hydroxide was obtained. This was removed by ultrafiltration.
Den erholdte oppløsning ble avionisert ved hjelp, av ionebytterharpikser av kjent type, og ble så oppkonsen-trert, hvorved man fikk 1250 kg laktulosesjrup med den følg-ende vektsammensetning; The obtained solution was deionized with the help of ion exchange resins of a known type, and was then concentrated, whereby 1250 kg of lactulose syrup with the following weight composition was obtained;
laktulose: ' 50% lactulose: ' 50%
laktose: 1,7% lactose: 1.7%
galaktose: 4,6% galactose: 4.6%
Aluminiumhydroxydet fra sentrifugedekanterings- og ultrafiltreringstrinnene ble slått sammen og behandlet med en 48 vekt% natriumhydroxydoppløsning inntil pH 11,5 ble oppnådd. Den resulterende oppløsning ble kalsinert ved 750°C, hvorved man fikk 400 kg 95% natriumaluminat som ble resirkulert til en etterfølgende syklus. The aluminum hydroxide from the centrifuge decantation and ultrafiltration steps was combined and treated with a 48% by weight sodium hydroxide solution until pH 11.5 was achieved. The resulting solution was calcined at 750°C, yielding 400 kg of 95% sodium aluminate which was recycled to a subsequent cycle.
Claims (5)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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NO892105A NO173663C (en) | 1989-05-25 | 1989-05-25 | Procedure for Preparation of Lactulose by Epimerization of Lactose in Aqueous Solution in the presence of Sodium Aluminum |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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NO892105A NO173663C (en) | 1989-05-25 | 1989-05-25 | Procedure for Preparation of Lactulose by Epimerization of Lactose in Aqueous Solution in the presence of Sodium Aluminum |
Publications (4)
Publication Number | Publication Date |
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NO892105D0 NO892105D0 (en) | 1989-05-25 |
NO892105L NO892105L (en) | 1990-11-26 |
NO173663B true NO173663B (en) | 1993-10-04 |
NO173663C NO173663C (en) | 1994-01-12 |
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Application Number | Title | Priority Date | Filing Date |
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NO892105A NO173663C (en) | 1989-05-25 | 1989-05-25 | Procedure for Preparation of Lactulose by Epimerization of Lactose in Aqueous Solution in the presence of Sodium Aluminum |
Country Status (1)
Country | Link |
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NO (1) | NO173663C (en) |
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1989
- 1989-05-25 NO NO892105A patent/NO173663C/en unknown
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Publication number | Publication date |
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NO892105L (en) | 1990-11-26 |
NO892105D0 (en) | 1989-05-25 |
NO173663C (en) | 1994-01-12 |
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