WO1989007640A1 - Anhydrides in detergent compositions - Google Patents

Anhydrides in detergent compositions

Info

Publication number
WO1989007640A1
WO1989007640A1 PCT/GB1989/000131 GB8900131W WO8907640A1 WO 1989007640 A1 WO1989007640 A1 WO 1989007640A1 GB 8900131 W GB8900131 W GB 8900131W WO 8907640 A1 WO8907640 A1 WO 8907640A1
Authority
WO
WIPO (PCT)
Prior art keywords
detergent composition
composition according
bleach activator
formula
detergent
Prior art date
Application number
PCT/GB1989/000131
Other languages
English (en)
French (fr)
Inventor
Stephen Robert Hodge
Andrew Pearce
Original Assignee
Bp Chemicals Limited
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bp Chemicals Limited filed Critical Bp Chemicals Limited
Priority to BR898905583A priority Critical patent/BR8905583A/pt
Priority to KR1019890701863A priority patent/KR960006560B1/ko
Publication of WO1989007640A1 publication Critical patent/WO1989007640A1/en
Priority to DK490589A priority patent/DK490589A/da
Priority to NO893968A priority patent/NO174716C/no
Priority to FI894777A priority patent/FI91537C/fi

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/39—Organic or inorganic per-compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
    • C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
    • C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D265/24—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in positions 2 and 4
    • C07D265/26—Two oxygen atoms, e.g. isatoic anhydride
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/39—Organic or inorganic per-compounds
    • C11D3/3902—Organic or inorganic per-compounds combined with specific additives
    • C11D3/3905—Bleach activators or bleach catalysts
    • C11D3/3907—Organic compounds
    • C11D3/3917—Nitrogen-containing compounds
    • C11D3/392—Heterocyclic compounds, e.g. cyclic imides or lactames

Definitions

  • the present invention relates to the use of anhydrides as bleach activators, especially in detergent compositions.
  • TAED tetraacetyl ethylene diamine
  • the present invention is a detergent composition in aqueous solution comprising
  • a surfactant selected from anionic, nonionic, zwitterionic and cationic surfactants and mixtures thereof,
  • a precursor compound capable of giving rise to a peroxygen compound in the presence of water
  • a detergent builder characterised in that the bleach activator comprises one or more cyclic anhydrides containing at least one nitrogen atom in the alpha position with respect to at least one of the carbonyl functions in the anhydride and the activator is at least partially soluble in water.
  • Q is a divalent organic grouping such that Q and N together with the carbonyl and oxygen functions in the anhydride group form one or more cyclic structures, and R is H, an alkyl, aryl, halogen, a carboxylic or a carbonyl containing function.
  • R has an aryl, alkaryl or aralkyl containing functions, it is essential that such functions also carry a substituent capable of solubilising the activator in aqueous systems eg. a sulphonic acid group.
  • R is a halogen containing functions, the halogen is preferably chlorine or bromine.
  • R has the same significance as in formula (I) above, and R 1 , R 2 , R 3 and R 4 may be the same or different nuclear substituents and may be selected from H, halogen, alkyl, alkenyl, aryl, alkoxyl, amino, COOR 5 , (where R 5 is an H or an alkyl group) and carbonyl containing functions. Specific examples of such compounds include cases where:
  • R has the same significance as in formula (I) above, and R 6 and R 7 may be the same or different groups and may be any one of the groups listed in the context of R 1 to R 4 above and n has a value from 1-3.
  • R has the same significance as in formula (I) above, and R 3 and R 9 are the same or different groups and may be any one of the groups designated for the substituents R 1 -R 4 above except that both R 8 and R 9 should not be H, or which together form one or more cyclic structure with or without additional hetero atoms.
  • R 8 and R 9 together represent one or more benzene rings as in formula (III) above, or, where they together with the hydrocarbyl carbon atoms in the anhydride ring represent a pyridine, pyrazole, pyrimidine or an imidazole ring.
  • R has the same significance as in formula (I) above.
  • the bleach activator is at least partially soluble in water.
  • solubility is at least 0.01%w/w in water at ambient temperature, eg. 25oC.
  • the activators of the present invention preferentially react with the peroxygen compound, eg. hydrogen peroxide generated by contacting the precursor compound with water.
  • the bleach activators of the present invention can be used or in conjunction with other conventional activators such as TAED, phthalic anhydride, maleic anhydride, succinic anhydride isononanoyl oxybenzene sulphonate (also known as isonobs') and tetracetyl glycoluril (also known as "TAGU”) and the like or with mixtures of such known activators.
  • TAED succinic anhydride isononanoyl oxybenzene sulphonate
  • TAGU tetracetyl glycoluril
  • water soluble anionic surfactants include the salts of alkyl benzene sulphonates, paraffin sulphonates, alpha-olefin sulphonates, alkyl glyceryl ether sulphonates and 2-acyloxy alkane-1-sulphonate, and beta-alkyloxy alkane sulphonate.
  • salts of alkyl sulphates, alkyl polyalkoxy ether sulphates, alpha-sulpho-carboxylates and their esters, fatty acid monoglyceride sulphates and sulphonates and alkyl phenol polyalkoxy ether sulphates may also be used.
  • Suitable examples of the above surfactants are linear straight chain alkyl benzene sulphonates having alkyl groups with 8-16 carbon atoms and methyl branched alkyl sulphates having 8-16 carbon atoms which are also effective.
  • anionic detergent compounds suitable for use herein include the sodium alkyl glyceryl ether sulphonates derived from tallow and coconut oil; sodium fatty acid monoglyceride sulphonates and sulphates derived from coconut oil; and sodium or potassium salts of C 8 -C 12 alkyl phenol alkylene oxide ether sulphate containing up to 10 alkylene oxide units per molecule. Mixtures of anionic surfactants may also be used.
  • the nonionic surfactants which may be used in the present invention are condensates of an alkylene oxide e.g. ethylene oxide with a hydrophobic group to form a surfactant having an appropriate hydrophilic-lipophilic balance (HLB) in the range from 8 to 17, suitably from 9.5 to 13.5, preferably from 10 to 12.5.
  • HLB hydrophilic-lipophilic balance
  • the hydrophobic group may be an aliphatic or aromatic type and the length of the polyoxyethylene group condensed therewith can be readily adjusted to yield a water-soluble compound having the desired degree of HLB.
  • nonionic surfactants include: (a) The polyethylene oxide condensates of alkyl phenol in which the alkyl group e.g. contains from 6 to 12 carbon atoms and in which from 3 to 30 moles, preferably 5 to 14 moles of ethylene oxide are present. Other examples include a mole of dodecylphenol condensed with 9 moles of ethylene oxide, a mole of dinonylphenol condensed with 11 moles of ethylene oxide and a mole of nonylphenol and octadecylphenol condensed with 13 moles of ethylene oxide. (a) The nonionic surfactant may also be formed as a condensation product of a mole of primary or secondary C 8 -C 24 aliphatic alcohols with from 2 to 40 moles, preferably 2 to 9 moles of ethylene oxide.
  • nonionic surfactants useful for the purposes of the invention include the various grades of Dobanol (Registered Trade Mark, supplied by Shell) Lutensol (Registered Trade Mark, supplied by BASF) and Synperonics (Registered Trade Mark, supplied by ICI).
  • nonionic surfactants include the synthetic nonionic detergents available on the market under
  • Zwitterionic compounds such as betaines and sulphobetaines, particularly those with a C 8 -C 16 alkyl substituent on the nitrogen atom can also be used as surfactants.
  • cationic surfactants examples include e.g. quaternary ammonium surfactants and surfactants of a semi-polar nature, for example amine oxides.
  • Suitable quaternary ammonium surfactants are the mono C 8 -C 16 , N-alkyl or alkenyl ammonium surfactants in which remaining N valences are methyl, hydroxyethyl or hydroxypropyl groups.
  • Suitable examples of amine oxides are the mono C 8 -C 20 , N-alkyl or alkenyl amine oxides and the propylene-1,3-diamine dioxides in which the remaining N valences are methyl, hydroxyethyl or hydroxypropyl substituents.
  • the detergent compositions can comprise from 1 to 70% w/w, suitably from 1 to 20% w/w of the total composition.
  • clathrate materials are used as peroxygen source (bleach precursor), a separate source of alkalinity will be required and for stability reasons these are preferably stored separately from the hydrogen peroxide source.
  • the precursor compound (ii) acting as the hydrogen peroxide source can be present in an amount of from 1 to 40% w/w suitably from 5 to 35% by weight, preferably from 10 to 30% by weight of the total composition.
  • the molar ratio of peroxygen compound eg. hydrogen peroxide generated from a bleach precursor to bleach activator is suitably greater than 1.5:1, preferably at least 2.0. Under the usage conditions encountered in domestic laundry practice, the molar ratio of bleach precursor to bleach activator is generally greater than 5.0:1 and is most preferably greater than 10:1.
  • Suds suppressing agents which are useful in the detergent compositions of the invention are suitably selected from silicone, wax, vegetable and hydrocarbon oil and phosphate ester varieties.
  • Suitable silicone suds controlling agents include polydimethylsiloxanes having a molecular weight in the range from 200 to 200,000 and a kinematic viscosity in the range from 20 to 2,000,000 mm 2 /s (cSt), preferably from 3000 to 30,000 mm 2 /s (cSt),
  • Water-insoluble detergent builders can also be used.
  • a specific example of such builders are the zeolites especially the sodium type A zeolite typified by SASIL (Registered Trade Mark), and mixtures of siloxanes and hydrophobic silanated (e.g. trimethylsilanated) silica having a particle size in the range from 10 to 20 millimicrons and a specific surface area above 50 m 2 /g.
  • Suitable waxes include microcrystalline waxes having a melting point in the range from 65oC to 100oC, a molecular weight in the range from 4,000-10,000 and a penetration value of at least 6, measured at 77oC by ASTM-D1321 and also paraffin waxes, synthetic waxes and natural waxes.
  • Suitable phosphate esters include mono- and/or di-C 16 -C 22 alkyl or alkenyl phosphate esters, and the corresponding mono- and/or di alkyl or alkenyl ether phosphates containing up to 6 ethoxy groups per molecule.
  • Suds suppressors are normally present in an amount from 0.01 to 5% w/w of the total composition depending upon the type of suds suppressor used, and is preferably from 0.1 to 2% w/w.
  • a highly preferred component of detergent compositions in accordance with the invention is one or more detergent builder salts which may comprise up to 90% of the composition, more typically from 10 to 70% by weight thereof.
  • Suitable detergent builder salts useful herein can be of the polyvalent inorganic and polyvalent organic types or mixtures thereof.
  • suitable water-soluble, inorganic alkaline detergent builder salts include the alkali metal carbonates, borates, phosphates, pyrophosphates, tripolyphosphates and bicarbonates.
  • Suitable organic alkaline detergency builder salts are water-soluble polycarboxylates such as the salts of nitrilotriacetic acid, lactic acid, glycollic acid and ether derivatives thereof; succinic acid, malonic acid, (ethylenedioxy)diacetic acid, maleic acid, diglycollic acid, tartaric acid, tartronic acid and fumaric acid; citric acid, aconitic acid, citraconic acid, carboxymethyloxysuccinic acid, lactoxysuccinic acid, and 2-oxy-1,1,3propane tricarboxylic acid; oxydisuccinic acid, 1,1,2,2-ethane tetracarboxylic acid, 1,1,3,3-propane tetracarboxylic acid and 1,1,2,3-propane tetracarboxylic acid; cyclopentane cis, cis, cistetracarboxylic acid, cyclopentadiene pentacarbox
  • 1,2 ,3,4,5,6-hexanehexacarboxylic acid 1,2 ,3,4,5,6-hexanehexacarboxylic acid, mellitic acid, pyromellitic acid and the phthalic acid derivatives.
  • Chelating agents, soil suspending and anti-redeposition agents, optical brightening agents, enzymes, colours and perfumes may also be added to the detergent composition.
  • Chelating agents that can be incorporated include citric acid, nitrilotriacetic and ethylene diamine tetra acetic acids and their salts, organic phosphonate derivatives such as those disclosed in US Patent Nos. 3,213,030, 3,433,021, 3,292,121 and 2 , 599 , 807 and carboxylic acid builder salts such as those disclosed in US Patent No . 3 , 308 , 067 .
  • the chelating agents can be present in amounts ranging from 0.1 to 3%, suitably from 0.2 to 2% by weight of the total composition.
  • the detergent compositions containing the bleach activators of the present invention may contain, in addition, minor conventional additives such as fragrances perfumes and the like.
  • bleach activators of the present invention should find wide use in detergent compositions which use the inorganic bleach precursors.
  • the fact that these anhydrides activate the bleach precursors at relatively lower temperatures e.g. from 20-60°C than those used hitherto should enable a considerable energy saving to be achieved, when the detergents are used.
  • the present invention is further illustrated with reference to the accompanying Examples. Example 1
  • %SR L sample - L redwine ⁇ 100 L white - L redwine

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Detergent Compositions (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
PCT/GB1989/000131 1988-02-11 1989-02-09 Anhydrides in detergent compositions WO1989007640A1 (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
BR898905583A BR8905583A (pt) 1988-02-11 1989-02-09 Composicao detergente em solucao aquosa e anidridos como ativadores alvejantes,especialmente em composicoes detergentes
KR1019890701863A KR960006560B1 (ko) 1988-02-11 1989-02-09 세제 조성물용 무수물
DK490589A DK490589A (da) 1988-02-11 1989-10-05 Anhydrider i detergentblandinger
NO893968A NO174716C (no) 1988-02-11 1989-10-05 Detergentblanding inneholdende anhydrider som blekemiddelaktivatorer
FI894777A FI91537C (fi) 1988-02-11 1989-10-09 Anhydridejä valkaisuaineaktivaattoreina pesuainekoostumuksissa

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB8803113 1988-02-11
GB888803113A GB8803113D0 (en) 1988-02-11 1988-02-11 Anhydrides in detergent compositions

Publications (1)

Publication Number Publication Date
WO1989007640A1 true WO1989007640A1 (en) 1989-08-24

Family

ID=10631493

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1989/000131 WO1989007640A1 (en) 1988-02-11 1989-02-09 Anhydrides in detergent compositions

Country Status (21)

Country Link
US (1) US4973418A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
EP (1) EP0331300B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
JP (1) JPH02500199A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
KR (1) KR960006560B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
CN (1) CN1036788A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
AT (1) ATE79399T1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
AU (1) AU604401B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
BR (1) BR8905583A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
CA (1) CA1312254C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
DE (1) DE68902403T2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
DK (1) DK490589A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
ES (1) ES2042996T3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
FI (1) FI91537C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
GB (1) GB8803113D0 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
GR (1) GR3006157T3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
IE (1) IE62952B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
IN (1) IN175857B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
NO (1) NO174716C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
NZ (1) NZ227888A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
PT (1) PT89694B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
WO (1) WO1989007640A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8803114D0 (en) * 1988-02-11 1988-03-09 Bp Chem Int Ltd Bleach activators in detergent compositions
GB9323634D0 (en) * 1993-11-16 1994-01-05 Warwick Int Ltd Bleach activator compositions
WO1995014760A1 (en) * 1993-11-25 1995-06-01 Warwick International Group Limited Bleach activators
HUT75294A (en) * 1994-02-25 1997-05-28 Eka Nobel Ab Particles comprising a core and a coat, preparation thereof, use thereof as bleaching agent and composition containing such particles
US5437686A (en) * 1994-05-18 1995-08-01 Colgate-Palmolive Co. Peroxygen bleach composition activated by bi and tricyclic diketones
SK281152B6 (sk) * 1994-10-07 2000-12-11 Eka Chemicals Ab Častica obsahujúca peroxyzlúčeninu a prostriedok, ktorý ju obsahuje
CZ285638B6 (cs) * 1994-10-07 1999-10-13 Eka Chemicals Ab Částice obsahující peroxysloučeninu a prostředek, který je obsahuje
EP1337621B1 (en) * 2000-11-27 2006-09-27 The Procter & Gamble Company Dishwashing method

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CH575401A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * 1971-08-23 1976-05-14 Sherwin Williams Co
GB1436810A (en) * 1974-05-09 1976-05-26 Ici Ltd Preparation of iostoic anhydride and anthranilic acid
US3984406A (en) * 1972-11-28 1976-10-05 Basf Aktiengesellschaft Production of unsubstituted or substituted isatoic anhydride
EP0020969A1 (de) * 1979-06-20 1981-01-07 BASF Aktiengesellschaft Verfahren zur Herstellung eines Gemischs von 3-Chloranthranilsäurealkylester und 6-Chloranthranilsäurealkylester
EP0021043A1 (de) * 1979-06-22 1981-01-07 BASF Aktiengesellschaft Verfahren zur Herstellung von Isatosäureanhydriden

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DK128287A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * 1967-10-24
US3850920A (en) * 1967-10-30 1974-11-26 Dow Chemical Co N-halo-3-morpholinone
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DE2910402A1 (de) * 1979-03-16 1980-09-25 Basf Ag Farbstabilisierte, nichtionische tenside und alkalische reinigerformulierungen, die diese tenside enthalten
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DE3136808A1 (de) * 1981-09-16 1983-03-31 Bayer Ag, 5090 Leverkusen Triazolidin-3,5-dione
GB8803114D0 (en) * 1988-02-11 1988-03-09 Bp Chem Int Ltd Bleach activators in detergent compositions

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CH575401A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * 1971-08-23 1976-05-14 Sherwin Williams Co
US3984406A (en) * 1972-11-28 1976-10-05 Basf Aktiengesellschaft Production of unsubstituted or substituted isatoic anhydride
GB1436810A (en) * 1974-05-09 1976-05-26 Ici Ltd Preparation of iostoic anhydride and anthranilic acid
EP0020969A1 (de) * 1979-06-20 1981-01-07 BASF Aktiengesellschaft Verfahren zur Herstellung eines Gemischs von 3-Chloranthranilsäurealkylester und 6-Chloranthranilsäurealkylester
EP0021043A1 (de) * 1979-06-22 1981-01-07 BASF Aktiengesellschaft Verfahren zur Herstellung von Isatosäureanhydriden

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Chemical Abstracts, vol. 92, no. 15, 14 April 1980, (Columbus, Ohio, US), N.R. Naik et al.: "Synthesis and spectral study of 1-methyl-2(R)-1,4-dihydro-4-oxoquinazoline derivatives", see pages 726-727 *
Chemical Abstracts, vol. 94, no. 11, 16 March 1981, (Columbus, Ohio, US), see page 712 *

Also Published As

Publication number Publication date
DE68902403D1 (de) 1992-09-17
BR8905583A (pt) 1990-11-20
CN1036788A (zh) 1989-11-01
AU604401B2 (en) 1990-12-13
NZ227888A (en) 1990-10-26
IE890374L (en) 1989-08-11
DK490589D0 (da) 1989-10-05
GR3006157T3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1993-06-21
GB8803113D0 (en) 1988-03-09
EP0331300B1 (en) 1992-08-12
EP0331300A1 (en) 1989-09-06
IE62952B1 (en) 1995-02-20
PT89694B (pt) 1994-03-31
IN175857B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1995-09-30
KR900700584A (ko) 1990-08-16
FI91537C (fi) 1994-07-11
CA1312254C (en) 1993-01-05
NO174716C (no) 1994-06-22
FI91537B (fi) 1994-03-31
KR960006560B1 (ko) 1996-05-17
US4973418A (en) 1990-11-27
AU3059289A (en) 1989-09-06
ATE79399T1 (de) 1992-08-15
DE68902403T2 (de) 1993-03-04
NO174716B (no) 1994-03-14
ES2042996T3 (es) 1993-12-16
NO893968L (no) 1989-10-05
DK490589A (da) 1989-10-05
FI894777A0 (fi) 1989-10-09
PT89694A (pt) 1989-10-04
JPH0534396B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1993-05-21
JPH02500199A (ja) 1990-01-25
NO893968D0 (no) 1989-10-05

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