NO169066B - DIACYLATION OF COMPOUNDS WITH TWO AROMATIC CORES - Google Patents

DIACYLATION OF COMPOUNDS WITH TWO AROMATIC CORES Download PDF

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NO169066B
NO169066B NO890658A NO890658A NO169066B NO 169066 B NO169066 B NO 169066B NO 890658 A NO890658 A NO 890658A NO 890658 A NO890658 A NO 890658A NO 169066 B NO169066 B NO 169066B
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general formula
compound
mol
acylating agent
diacylation
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NO890658A
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NO890658L (en
NO890658D0 (en
NO169066C (en
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Michel Devic
Jacques Kervennal
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Atochem
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Publication of NO169066C publication Critical patent/NO169066C/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/29—Saturated compounds containing keto groups bound to rings
    • C07C49/35—Saturated compounds containing keto groups bound to rings containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/782—Ketones containing a keto group bound to a six-membered aromatic ring polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/12—Polycyclic non-condensed hydrocarbons
    • C07C15/14—Polycyclic non-condensed hydrocarbons all phenyl groups being directly linked
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
    • C07C15/12—Polycyclic non-condensed hydrocarbons
    • C07C15/16—Polycyclic non-condensed hydrocarbons containing at least two phenyl groups linked by one single acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
    • C07C321/12—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms
    • C07C321/20—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/46—Friedel-Crafts reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Television Signal Processing For Recording (AREA)
  • Networks Using Active Elements (AREA)
  • Electrotherapy Devices (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Diacylation of compounds of general formula <IMAGE> with X : O, S, <IMAGE> or -CH2- R1, R2, R3 and R4, which are identical or different: H or an alkyl radical containing from 1 to 4 carbon atoms, by bringing the compound (I) into contact with HF, BF3 and at least 2 moles of an acylating agent per mole of (I) at a temperature of between -40 DEG C and 0 DEG C.

Description

Foreliggende oppfinnelse angår en fremgangsmåte for diacylering av forbindelser med 2 aromatiske kjerner i molekylet og med den generelle formel: The present invention relates to a method for the diacylation of compounds with 2 aromatic nuclei in the molecule and with the general formula:

der there

x er et oksygen- eller svovelatom, en gruppe x is an oxygen or sulfur atom, a group

eller -CH2-; or -CH2-;

Ri, R2» R3 °S R4» like eller forskjellige, betyr et hydrogen-atom eller en alkylgruppe med 1 til 4 karbonatomer. R1, R2, R3, R4, the same or different, means a hydrogen atom or an alkyl group with 1 to 4 carbon atoms.

Med diacylering menes her og i det følgende transformering av en forbindelse med den generelle formel (I) til en forbindelse med den generelle formel By diacylation is meant here and in the following the transformation of a compound of the general formula (I) into a compound of the general formula

der x, , R£, R3, R4 har den samme betydning som under (I); R er angitt som R^, R2, R3, R4; ved hjelp av et acyleringsmiddel med den generelle formel: where x, , R£, R3, R4 have the same meaning as under (I); R is indicated as R 1 , R 2 , R 3 , R 4 ; using an acylating agent of the general formula:

der there

Y er et halogenatom, en gruppe -0H, -OR eller Y is a halogen atom, a group -OH, -OR or

R hver gang er som angitt under (II). R each time is as indicated under (II).

Eksempler på acyleringsmidler er således definert som i EP-069597. Examples of acylating agents are thus defined as in EP-069597.

Forbindelsene med formel (III) benyttes i industrien som mellomprodukter, for eksempel for å komme frem til polymerer av polyestertypen. Dette er spesielt tilfelle for de der R befinner seg i 4 og 4' stilling slik som i 4,4'-diacetyldifenyleter: Det er kjent å acylere difenyleter for for eksempel å fremstille 4-fenoksyacetofenon The compounds of formula (III) are used in industry as intermediate products, for example to arrive at polymers of the polyester type. This is especially the case for those where R is in the 4 and 4' position, such as in 4,4'-diacetyldiphenyl ether: It is known to acylate diphenyl ether to, for example, prepare 4-phenoxyacetophenone

som for eksempel beskrevet i det nevnte europeiske patent. as, for example, described in the aforementioned European patent.

Dette patent angir at acylering i nærvær av fluss-syre, HF, så og si utelukker diacylering, en diacylering som imidlertid antydes gjennomførbar ved hjelp av aluminiumklorid AICI3. This patent states that acylation in the presence of hydrofluoric acid, HF, so to speak excludes diacylation, a diacylation which, however, is suggested to be feasible with the aid of aluminum chloride AICI3.

Det er kjent mangler I forbindelse med anvendelse av denne sistnevnte forbindelse, mangler som i vesentlig grad berenser den industrielle interesse. There are known deficiencies in connection with the use of this last-mentioned compound, deficiencies which to a significant extent detract from the industrial interest.

Foreliggende oppfinnelse tillater å unngå et slikt valg og fører til produkter med formel (II) som har en høy renhet og med et høyt kjemisk utbytte, således et høyt diacylerings-utbytte av forbindelsen med den generelle formel (I). The present invention allows avoiding such a choice and leads to products of formula (II) which have a high purity and with a high chemical yield, thus a high diacylation yield of the compound of the general formula (I).

Foreliggende oppfinnelse angår således en fremgangsmåte for diacylering av forbindelser med den generelle formel (I) til forbindelser med den generelle formel (II) ved kontakt i vannfritt medium mellom en forbindelse med den generelle formel (I) med et acyleringsmiddel med den generelle formel (III), og denne fremgangsmåte karakteriserees ved at gjennomføringen består i at kontakten gjennomføres ved en temperatur mellom -40 og 0°C i nærvær av fluss-syre HF, borfluorid BF3 og minst 2 mol av et acyleringsmiddel med den generelle formel (III) pr. mol forbindelse med den generelle formel (I). The present invention thus relates to a method for the diacylation of compounds of the general formula (I) to compounds of the general formula (II) by contact in an anhydrous medium between a compound of the general formula (I) with an acylating agent of the general formula (III) ), and this method is characterized by the implementation consisting in the contact being carried out at a temperature between -40 and 0°C in the presence of hydrofluoric acid HF, boron fluoride BF3 and at least 2 mol of an acylating agent with the general formula (III) per mol of compound with the general formula (I).

Det mål foreliggende oppfinnelse tar sikte på, diacylering av en forbindelse med den generelle formel (I), oppnås mere generelt når 1 til 25 mol HF og 5 til 20 mol BF3 er tilstede pr. mol av den nevnte forbindelse. The goal of the present invention, diacylation of a compound of the general formula (I), is more generally achieved when 1 to 25 mol HF and 5 to 20 mol BF 3 are present per moles of the said compound.

Molforholdet BF3 :HF som er mest hensiktsmessig ligger mellom 10 : 1 og 0,5 : 1. The molar ratio BF3:HF that is most appropriate is between 10:1 and 0.5:1.

Molforholdet acyleringsmiddel : forbindelse med formel (I) er fortrinnsvis begrenset til en verdi som ikke går ut over 5 : 1. The molar ratio of acylating agent: compound of formula (I) is preferably limited to a value that does not exceed 5:1.

Syreklorider og syreannhydrider er de hyppigste acyleringsmidler, spesielt fortrekkes acetylklorid og eddiksyreanhydrid. Acid chlorides and acid anhydrides are the most frequent acylating agents, acetyl chloride and acetic anhydride are particularly preferred.

Nærværet av et oppløsningsmiddel i acyleringsmediet kan være brukbart, spesielt for å lette oppløseliggjøring av forbindelsen med den generelle formel (I) og kontakte mellom mediets bestanddeler. The presence of a solvent in the acylation medium may be useful, in particular to facilitate solubilization of the compound of general formula (I) and contact between the constituents of the medium.

Oppløsningmidlet velges således blant de som i og for seg er kjente for reaksjoner av Friedel-krafts typen, altså midler av typen diklormetan, nitrometan eller karbondisulfid. The solvent is thus chosen from among those known in and of themselves for reactions of the Friedel-kraft type, i.e. agents of the type dichloromethane, nitromethane or carbon disulphide.

Gjennomføring av fremgangsmåten ifølge oppfinnelsen kan skje i enhver form for utstyr som motstår trykk og påvirkning av HF og BF3 under de ovenfor angitte betingelser, en autoklav av rustfritt stål kan med fordel benyttes. Implementation of the method according to the invention can take place in any type of equipment that resists pressure and the influence of HF and BF3 under the conditions stated above, a stainless steel autoclave can be advantageously used.

Tidsrommet for gjennomføring av oppfinnelsen fremgangsmåte er generelt meget kort og varigheten er generelt innen rammen 1 time. The time frame for carrying out the invention method is generally very short and the duration is generally within the framework of 1 hour.

De følgende eksempler skal illustrere oppfinnelsen uten å begrense den. The following examples are intended to illustrate the invention without limiting it.

For alle eksempler gjelder: For all examples apply:

Forbindelsen med den generelle formel (I), acyleringsmidlet, HF, BF3 og eventuelt metylenklorid som benyttes som opp-løsningsmiddel, bringes i kontakt i en omrørt autoklav av rustfritt stål i 1 time; The compound with the general formula (I), the acylating agent, HF, BF3 and optionally methylene chloride which is used as solvent, are brought into contact in a stirred stainless steel autoclave for 1 hour;

med renhet menes den som uttrykkes i vekt-56 av forbindelsen med den generelle formel (II) som oppstår ved tilsetning av vann og natriumhydroksyd fulgt av en filtrering med vasking med vann og tørking under undertrykk ved 80°C; by purity is meant that expressed in weight-56 of the compound of the general formula (II) resulting from the addition of water and sodium hydroxide followed by a filtration with washing with water and drying under reduced pressure at 80°C;

med kjemisk utbytte menes antallmol, uttrykt 1 prosent, av forbindelsen med den generelle formel (I) som er overført til forbindelsen med den generelle formel (II). by chemical yield is meant the number of moles, expressed as 1 percent, of the compound of the general formula (I) which has been transferred to the compound of the general formula (II).

Eksempel 1: Example 1:

Difenyleter Diphenyl ether

bringes, ved -40°C og pr. mol difenyleter, i kontakt med 2,2 mol eddiksyreanhydrid, 10 mol HF og 15 mol BF3. brought, at -40°C and per mol of diphenyl ether, in contact with 2.2 mol of acetic anhydride, 10 mol of HF and 15 mol of BF3.

Renheten for den oppnådde 4,4'-diacetyldifenyleter samt det kjemiske utbytte er over 98 #. The purity of the obtained 4,4'-diacetyldiphenyl ether as well as the chemical yield is above 98 #.

Eksempel 2: Example 2:

Difenylsufid Diphenylsulfide

bringes ved 0°C og pr. mol difenylsulfid i kontakt med 3 mol acetylklorid, 10 mol HF, 7,5 mol BF3 og 200 g metylenklorid. brought at 0°C and per mol of diphenyl sulphide in contact with 3 mol of acetyl chloride, 10 mol of HF, 7.5 mol of BF3 and 200 g of methylene chloride.

Renheten for det oppnådde 4,4'-diacetyldifenylsulfid er lik 96 % og det kjemiske utbytte er lik 90 #. The purity of the obtained 4,4'-diacetyldiphenyl sulfide is equal to 96% and the chemical yield is equal to 90#.

Eksempel 3; Example 3;

P.difenylbenzen P.diphenylbenzene

bringes ved 0°C og pr. mol p.fenylbenzen i kontakt med 3 mol acetylfluorid, 20 mol HF, 15 mol BF3 og 400 g metylenklorid. brought at 0°C and per mol of p.phenylbenzene in contact with 3 mol of acetyl fluoride, 20 mol of HF, 15 mol of BF3 and 400 g of methylene chloride.

Renheten for det oppnådde 4,4'-diacetyldifenylbenzen er over 98 % og det kjemiske utbyttet er lik 92 %. The purity of the obtained 4,4'-diacetyldiphenylbenzene is over 98% and the chemical yield is equal to 92%.

Eksempel 4: Example 4:

DifenyImetan DiphenyImetane

bringes ved -20°C og pr.mol difenylmetan i kontakt med 2,2 mol eddiksyreanhydrid, 2,5 mol HF, 15 mol BF3 og 200 g metylenklorid. is brought at -20°C and per mol of diphenylmethane into contact with 2.2 mol of acetic anhydride, 2.5 mol of HF, 15 mol of BF3 and 200 g of methylene chloride.

Renheten for det oppnådde 4,4'-diacetyldifenylmetan er lik 90 % og det kjemiske utbytte er lik 20 %. The purity of the 4,4'-diacetyldiphenylmethane obtained is equal to 90% and the chemical yield is equal to 20%.

Eksempel 5: Example 5:

M.benzyltoluen M.benzyltoluene

bringes ved 0°C og pr. mol m.benzyltoluen i kontakt med 3 mol acetylklorid, 2,5 mol HF og 15 mol BF3. brought at 0°C and per mol m.benzyltoluene in contact with 3 mol acetyl chloride, 2.5 mol HF and 15 mol BF3.

Det kjemiske utbyttet er 80 # og det oppnådde produkt har en renhet på 90 % av diacetylerte forbindelser, særlig slike som er diacetylert i 4 og 4'-stilling. The chemical yield is 80 # and the product obtained has a purity of 90% of diacetylated compounds, especially those which are diacetylated in the 4 and 4' position.

Claims (8)

1. Fremgangsmåte for diacylering av forbindelser med 2 aromatiske kjerner i sitt molekyl der molekylet har den generelle formel der x er et oksygen- eller svovelatom, en gruppe eller -CHo-: Ri, R2, R3 og R4, like eller forskjellige, betyr et hydrogen-atom eller en alkylgruppe med 1 til 4 karbonatomer. Med diacylering menes her og i det følgende transformering av en forbindelse med den generelle formel (I) til en forbindelse med den generelle formel der x, Ri, R2, R3, R4 har den samme betydning som under (I); R er angitt som Ri, R2, R3, R4; ved hjelp av et acyleringsmiddel med den generelle formel: der Y er et halogenatom, en gruppe -0H, -OR eller R hver gang er som angitt under (II), ved kontakt mellom et vannfritt medium av en forbindelse med den generelle formel (I) og et acyleringsmiddel med den generelle formel (III), karakterisert ved at kontakten gjennomføres ved en temperatur mellom -40 og 0°C i nærvær av fluss-syre HF, bortrifluorid BF3 og minst 2 mol acyleringsmiddel med formel (III) pr. mol forbindelse med den generelle formel (I).1. Method for the diacylation of compounds with 2 aromatic nuclei in their molecule where the molecule has the general formula there x is an oxygen or sulfur atom, a group or -CHo-: R 1 , R 2 , R 3 and R 4 , the same or different, mean a hydrogen atom or an alkyl group of 1 to 4 carbon atoms. By diacylation is meant here and in the following the transformation of a compound of the general formula (I) into a compound of the general formula there x, R 1 , R 2 , R 3 , R 4 have the same meaning as under (I); R is indicated as R 1 , R 2 , R 3 , R 4 ; using an acylating agent of the general formula: there Y is a halogen atom, a group -OH, -OR or R each time is as indicated under (II), in the case of contact between an anhydrous medium of a compound of the general formula (I) and an acylating agent of the general formula (III), characterized in that the contact is carried out at a temperature between -40 and 0°C in the presence of hydrofluoric acid HF, boron trifluoride BF3 and at least 2 mol of acylating agent with formula (III) per mol of compound with the general formula (I). 2. Fremgangsmåte ifølge krav 1, karakterisert ved at man anvender 1 til 25 mol HF og 5 til 20 mol BF3 pr. mol forbindelse med formel (I).2. Method according to claim 1, characterized in that 1 to 25 mol HF and 5 to 20 mol BF3 are used per mol of compound of formula (I). 3. Fremgangsmåte ifølge krav 1 eller 2, karakterisert ved at man anvender et molforhold BF3 : HF på mellom 10 : 1 og 0,5 : 1.3. Method according to claim 1 or 2, characterized in that a BF3 : HF molar ratio of between 10 : 1 and 0.5 : 1 is used. 4. Fremgangsmåte ifølge et hvilket som helst av kravene 1 til 3, karakterisert ved at man anvender et molforhold acyleringsmiddel : forbindelse med formel (I) som ikke overskrider 5:1.4. Method according to any one of claims 1 to 3, characterized in that a molar ratio of acylating agent: compound of formula (I) which does not exceed 5:1 is used. 5. Fremgangsmåte ifølge et hvilket som helst av kravene 1 til 4, karakterisert ved at man som acyleringsmiddel anvender acetylklorid.5. Process according to any one of claims 1 to 4, characterized in that acetyl chloride is used as acylating agent. 6. Fremgangsmåte Ifølge hvilket som helst av kravene 1 til 4, karakterisert ved at man som acyleringsmiddel anvender eddiksyreanhydrid.6. Method According to any one of claims 1 to 4, characterized in that acetic anhydride is used as acylating agent. 7. Fremgangsmåte ifølge et hvilket som helst av kravene 1 til 6, karakterisert ved at man anvender et vannfritt medium som omfatter et oppløsningsmiddel.7. Method according to any one of claims 1 to 6, characterized in that an anhydrous medium is used which comprises a solvent. 8. Fremgangsmåte ifølge krav 7, karakterisert ved at man som oppløsningsmiddel velger metylenklorid.8. Method according to claim 7, characterized in that methylene chloride is chosen as solvent.
NO890658A 1988-02-18 1989-02-16 DIACYLATION OF COMPOUNDS WITH TWO AROMATIC CORES NO169066C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR8802192A FR2627486B1 (en) 1988-02-18 1988-02-18 PROCESS FOR THE DIACYLATION OF COMPOUNDS COMPRISING TWO AROMATIC CORES

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NO890658D0 NO890658D0 (en) 1989-02-16
NO890658L NO890658L (en) 1989-08-21
NO169066B true NO169066B (en) 1992-01-27
NO169066C NO169066C (en) 1992-05-06

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EP (1) EP0340117B1 (en)
JP (1) JPH023619A (en)
KR (1) KR950008286B1 (en)
CN (1) CN1020718C (en)
AT (1) ATE78019T1 (en)
AU (1) AU619523B2 (en)
DE (1) DE68902005T2 (en)
DK (1) DK73389A (en)
ES (1) ES2043072T3 (en)
FI (1) FI890798A (en)
FR (1) FR2627486B1 (en)
GR (1) GR3005886T3 (en)
IE (1) IE890498L (en)
IL (1) IL89128A0 (en)
NO (1) NO169066C (en)
PT (1) PT89752B (en)
ZA (1) ZA891212B (en)

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DE3927772A1 (en) * 1989-08-23 1991-02-28 Bayer Ag METHOD FOR PRODUCING AROMATIC DICARBONIC ACIDS AND NEW AROMATIC DICARBONIC ACIDS
JP4937435B2 (en) * 1998-11-05 2012-05-23 修一 広野 Novel compounds and their pharmaceutical uses
JP2002534488A (en) 1999-01-12 2002-10-15 クラリアント・インターナシヨナル・リミテツド Benzophenone and its use as a photopolymerization initiator
EP1211235A3 (en) * 2000-11-30 2004-01-02 JFE Chemical Corporation Preparation process of 4,4'-Dicarboxydiphenyl ethers or derivatives thereof
CN1297530C (en) * 2004-05-17 2007-01-31 河南大学 Process for preparing n-hexylic acid by oxidation of sec- octyl alcohol with nitric acid and its special device
CN1332923C (en) * 2005-11-16 2007-08-22 陕西师范大学 2-(9-anthryl)-2-carbonylethyl acetate solid phase synthesis method

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JPS5929178B2 (en) * 1978-04-08 1984-07-18 丸善石油化学株式会社 Process for producing 2-alkyl-6-acylnaphthalene
ES8306085A1 (en) * 1981-07-08 1983-05-01 Raychem Corp Preparation of aromatic ketones.
FR2519974A1 (en) * 1982-01-21 1983-07-22 Rhone Poulenc Spec Chim PROCESS FOR THE ACYLATION OF HALOGENO OR TRIHALOGENOMETHYLBENZENES
ES8700647A1 (en) * 1984-10-11 1986-11-16 Raychem Corp Preparation of aromatic carbonyl compounds.
EP0189266A3 (en) * 1985-01-18 1986-10-08 The Dow Chemical Company Purification of haloacetyl derivatives of aromatic hydrocarbons
FR2577220B1 (en) * 1985-02-08 1987-05-29 Rhone Poulenc Spec Chim PROCESS FOR ACETOACETYLATION OF AROMATIC COMPOUNDS
FR2580276B1 (en) * 1985-04-16 1988-08-12 Rhone Poulenc Spec Chim PROCESS FOR THE PREPARATION OF ACYLBIPHENYLES

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CN1035105A (en) 1989-08-30
ES2043072T3 (en) 1993-12-16
DE68902005D1 (en) 1992-08-13
NO890658L (en) 1989-08-21
DE68902005T2 (en) 1993-01-14
CN1020718C (en) 1993-05-19
IE890498L (en) 1989-08-18
EP0340117A1 (en) 1989-11-02
DK73389D0 (en) 1989-02-17
PT89752A (en) 1989-10-04
FR2627486A1 (en) 1989-08-25
NO890658D0 (en) 1989-02-16
ZA891212B (en) 1989-11-29
IL89128A0 (en) 1989-08-15
AU3006689A (en) 1989-08-24
NO169066C (en) 1992-05-06
EP0340117B1 (en) 1992-07-08
JPH023619A (en) 1990-01-09
AU619523B2 (en) 1992-01-30
KR890012929A (en) 1989-09-20
PT89752B (en) 1994-03-31
FR2627486B1 (en) 1991-03-22
DK73389A (en) 1989-08-19
FI890798A (en) 1989-08-19
KR950008286B1 (en) 1995-07-27
FI890798A0 (en) 1989-02-17
ATE78019T1 (en) 1992-07-15
GR3005886T3 (en) 1993-06-07

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