EP0542677B1 - Lagerstabile Formulierung von optischen Aufhellermischungen - Google Patents

Lagerstabile Formulierung von optischen Aufhellermischungen Download PDF

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Publication number
EP0542677B1
EP0542677B1 EP92810830A EP92810830A EP0542677B1 EP 0542677 B1 EP0542677 B1 EP 0542677B1 EP 92810830 A EP92810830 A EP 92810830A EP 92810830 A EP92810830 A EP 92810830A EP 0542677 B1 EP0542677 B1 EP 0542677B1
Authority
EP
European Patent Office
Prior art keywords
weight
liquid storage
whitener formulation
stable
formulation according
Prior art date
Legal status (The legal status 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 status listed.)
Expired - Lifetime
Application number
EP92810830A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0542677A1 (de
Inventor
Werner Dr. Fringeli
Josef Zelger
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF Schweiz AG
Original Assignee
Ciba Geigy AG
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 Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of EP0542677A1 publication Critical patent/EP0542677A1/de
Application granted granted Critical
Publication of EP0542677B1 publication Critical patent/EP0542677B1/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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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
    • C11D3/395—Bleaching agents
    • 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
    • C11D3/40—Dyes ; Pigments
    • C11D3/42—Brightening agents ; Blueing agents
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
    • D06L4/60—Optical bleaching or brightening
    • D06L4/614—Optical bleaching or brightening in aqueous solvents
    • D06L4/621—Optical bleaching or brightening in aqueous solvents with anionic brighteners
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06L—DRY-CLEANING, WASHING OR BLEACHING FIBRES, FILAMENTS, THREADS, YARNS, FABRICS, FEATHERS OR MADE-UP FIBROUS GOODS; BLEACHING LEATHER OR FURS
    • D06L4/00—Bleaching fibres, filaments, threads, yarns, fabrics, feathers or made-up fibrous goods; Bleaching leather or furs
    • D06L4/60—Optical bleaching or brightening
    • D06L4/664—Preparations of optical brighteners; Optical brighteners in aerosol form; Physical treatment of optical brighteners

Definitions

  • the present invention relates to storage-stable liquid optical brightener formulations, a process for their preparation and their use.
  • Optical brighteners are usually marketed preferably in the form of aqueous solutions or suspensions.
  • aqueous solutions or suspensions e.g. the wet filter cake or the dry powder slurried with water.
  • the suspensions thus obtained are then mixed with dispersing and thickening agents to increase homogeneity, wettability and stability.
  • An electrolyte is often added as a further auxiliary.
  • the auxiliaries used hitherto could not prevent sedimentation of the brighteners and / or a high increase in viscosity, especially at high storage temperatures, over a longer period of time.
  • Such formulations preferably contain anionic optical brighteners which contain at least one sulfonic acid residue.
  • optical brighteners are:
  • the secondary and tertiary amine are, for example, unsubstituted or mono- or polysubstituted phenylamine, morpholine, piperidine, methylamine, ethylamine, propylamine, butylamine, ⁇ -hydroxyethylamine, or with C1-C4alkyl, C1-C4alkoxy, sulfo, halogen, cyano, or carboxy.
  • ⁇ -hydroxypropylamine ⁇ -cyano-ethylamine, dimethylamine, diethylamine, dipropylamine, bis- ⁇ -hydroxyethylamine, N-methyl-N-ethylamine, N-methyl-N- ⁇ -hydroxyethylamine, N-ethyl-N- ⁇ -hydroxyethylamine, N-methyl-N- ⁇ -hydroxypropylamine, N-ethyl-N- ⁇ -hydroxypropylamine, benzylamine, N- ⁇ -hydroxyethyl-benzylamine, cyclohexylamine, N-ethyl-cyclohexylamine, 2-methoxy-ethylamine, 2-ethoxy-ethylamine, N-methyl-2-methoxyethylamine and 3-methoxypropylamine in question.
  • unsubstituted, mono- or disubstituted alkoxy examples include methoxy, ethoxy, n-propoxy, i-propoxy, butoxy, ⁇ -hydroxy-ethoxy, ⁇ -methoxy-ethoxy and ⁇ -ethoxy-ethoxy.
  • optical brighteners of the formula (1) in which X and Y, which may be the same or different, are a phenylamino group which is optionally mono- or di-substituted by alkyl radicals having 1 or 2 carbon atoms; the morpholino group; an alkylamino group having 1 to 4 carbon atoms, which may be substituted by hydroxyl radicals; or represent an alkoxy group having 1 to 4 carbon atoms; and M represents hydrogen or a salt-forming cation.
  • Optical brighteners of the formula (1) are furthermore preferred, in which X and Y, which may be identical or different, are phenylamino, morpholino, an alkylamino group having 1 to 4 carbon atoms, which may be substituted by hydroxyl radicals, and M is hydrogen or a salt-forming cation.
  • X and Y which may be identical or different, are phenylamino, morpholino, an alkylamino group having 1 to 4 carbon atoms, which may be substituted by hydroxyl radicals, and M is hydrogen or a salt-forming cation.
  • the morpholino and the N-methyl-N-ethanolamino groups are particularly preferred.
  • optical brighteners of the formulas (2) where M is an alkali metal ion in the case of this optical brightener a content of 2 to 25% by weight, based on the total weight of the slurry, of a strong electrolyte is expediently present; and (3) where M denotes an alkali metal ion.
  • A is a sulfonic acid residue, hydrogen, C1-C4-alkyl, C1-C4-alkoxy or halogen and B is hydrogen, C1-C4-alkyl, C1-C4-alkoxy or halogen, with the condition that at least one substituent A is a sulfonic acid residue is and m, n, o, p independently of one another represent a number 1 or 2.
  • Particularly preferred compounds are compounds of the formulas and where A, B and n have the above meaning and M is a salt-forming cation.
  • halogens are fluorine, chlorine and bromine, but especially chlorine.
  • C1-C4 alkyl radicals are unbranched and branched alkyl radicals such as the methyl, ethyl, n- and iso-propyl, n-, sec- and tert-butyl radical. These C1-C4 alkyl radicals can in turn be substituted with e.g. Aryl (phenyl, naphthyl), C1-C4 alkoxy, OH, halogen, sulfo or CN groups.
  • Salt-forming cations M are e.g. Alkali metal, ammonium or amine salt ions.
  • Amine salt ions are preferred those of the formula H+NR1R2R3 in which R1, R2 and R3 independently of one another are hydrogen, alkyl, alkenyl, hydroxyalkyl, cyanoalkyl, halogenoalkyl or phenylalkyl or in which R1 and R2 together are the addition to a 5-7-membered saturated Represent nitrogen heterocycle, which may additionally contain a nitrogen or oxygen atom as a ring member, for example a piperidine, piperazine, pyrrolidine, imidazoline or morpholine ring, while R3 is hydrogen.
  • Preferred salt-forming cations are akali metal salts, Na+ and K+ being particularly preferred.
  • Preferred distyrylbiphenyl compounds of the formula (4) are those in which the cation M is an alkali metal, ammonium or amine ion, potassium and sodium being of particular importance for practical reasons.
  • Preferred mixtures each consist of 5 to 30% by weight, based on the total weight, but not more than 45% by weight, of two, three or four brighteners of the formulas (2), (3), (7) and (8) ,
  • the ratio of the optical brighteners to one another is between 1: 9 and 9: 1, preferably between 1: 4 and 4: 1.
  • electrolyte e.g. one or more alkali metal salts and salts of lower carboxylic acids
  • electrolytes are sodium chloride, sodium sulfate, sodium phosphate, sodium carbonate, sodium formate or one of the corresponding potassium salts and mixtures of these electrolytes.
  • Sodium chloride and the formates are preferred.
  • the amount of electrolyte can be 0.1 to 25% by weight, preferably 0.5 to 20% by weight and particularly preferably 0.5-15% by weight, based on the total weight of the formulation.
  • anionic polysaccharides which can be used according to the invention belong to the group of modified polysaccharides which can be derived from cellulose, starch or from the heteropolysaccharides, with further monosaccharides such as e.g. Mannose and glucuronic acid can be included.
  • examples of anionic polysaccharides are sodium alginate, carboxymethylated guar, carboxymethyl cellulose, carboxymethyl starch, carboxymethylated locust bean gum and, particularly preferably, xanthan.
  • the amount of polysaccharide is 0.01 to 1% by weight, a range from 0.05 to 0.5% by weight being preferred and a range from 0.05-0.2% by weight being particularly preferred, based in each case on the total weight of the formulation. However, with very highly concentrated or very low concentrated formulations, these ranges can be exceeded.
  • the brightener formulation according to the invention can optionally contain additives; Preservatives such as chloroacetamide or aqueous formaldehyde solution, Mg / Al silicates, odor improvers and antifreezes may be mentioned as examples.
  • Mg / Al silicates examples are bentonite, montmorillonite, zeolites and highly disperse silicas. They are usually added in an amount of 0.2-1% by weight, based on the total weight of the brightener formulation.
  • Dispersants which can be used are those of the anionic or nonionic type. Examples include alkyl benzene, alkyl or Alkenylethersulfonatsalze, saturated or unsaturated fatty acids, alkyl or Alkylenethercarboxylsalze, sulfofatty or esters, Phosphatester, polyoxyethylene alkyl or alkenyl, polyoxyethylene alkyl vinyl ether, polyoxypropylene alkyl or alkenyl, Polyoxybutylenalkyl - or alkenyl ether, higher fatty acid or Alkylene oxide adducts, sucrose / fatty acid esters, fatty acid / glycol monoesters, alkylamine oxides and condensation products of aromatic sulfonic acids with formaldehyde as well as lignin sulfonates or mixtures of the above-mentioned dispersants.
  • condensation products of aromatic sulfonic acids with formaldehyde and lignin sulfonates are preferred.
  • Condensation products of naphthalene sulfonic acids with formaldehyde and ditolyl ether sulfonic acids with formaldehyde are particularly preferred.
  • the content of dispersant is 0.2 to 20% by weight, based on the total weight of the formulation, preferably 0.1 to 10% by weight and particularly preferably 0.2 to 5% by weight.
  • Formulations according to the invention are obtained by adding the moist presscakes or the dry powders of at least two anionic optical brighteners which contain at least one sulfonic acid residue in an amount of 15 to 45% by weight, preferably 15 to 40% by weight and particularly preferably 19 -40% by weight, based on the total weight of the formulation; with 0.01 to 1% by weight of anionic polysaccharide; 0.1 to 25% by weight electrolyte; 0.2 to 20 wt% dispersant; if necessary with further additives; and mixed with water and homogenized at room temperature.
  • the desired content of anionic optical brighteners in the suspension can be adjusted either by adding water, aqueous electrolyte, or further dry powder to the moist filter cake. This setting can be made before, during or after the addition of the anionic polysaccharide.
  • the new optical brightener formulations are used primarily in the incorporation into detergents, e.g. B. by inflowing the required amount of the optical brightener formulation according to the invention, from a container into a mixing device which contains a suspension of the detergent or the dispersant.
  • the present invention accordingly also relates to a process for the production of solid and liquid detergents, and to the detergents obtained thereafter, characterized in that a suspension for detergents of conventional detergents, mixed with an inventive suspension of brighteners, and dried.
  • the drying process can e.g. done by a spray drying process.
  • the brightener formulation according to the invention can advantageously be used for the production of liquid detergents.
  • Percentages refer to the total weight of the formulation.
  • the brightener formulations obtained remain liquid and do not form any deposits after standing for two months at -5 ° C., room temperature and 40 ° C.
  • the components listed in Table 2 are stirred with 1% by weight, based on the total weight of the brightener formulation, of the condensation product of ditolyl ether sulfonic acids with formaldehyde; 0.15% by weight of xanthan and water mixed and homogenized.
  • the brightener formulations remain liquid and do not form any deposits after standing for several weeks at room temperature and 40 ° C.
  • the brightener formulations remain liquid and do not form any deposits after standing for several weeks at room temperature and 40 ° C.

Landscapes

  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Textile Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Paints Or Removers (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)
  • Cosmetics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
EP92810830A 1991-11-07 1992-10-28 Lagerstabile Formulierung von optischen Aufhellermischungen Expired - Lifetime EP0542677B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH3245/91 1991-11-07
CH3245/91A CH682748A5 (de) 1991-11-07 1991-11-07 Lagerstabile Formulierung von optischen Aufhellermischungen.

Publications (2)

Publication Number Publication Date
EP0542677A1 EP0542677A1 (de) 1993-05-19
EP0542677B1 true EP0542677B1 (de) 1996-03-13

Family

ID=4251796

Family Applications (1)

Application Number Title Priority Date Filing Date
EP92810830A Expired - Lifetime EP0542677B1 (de) 1991-11-07 1992-10-28 Lagerstabile Formulierung von optischen Aufhellermischungen

Country Status (17)

Country Link
US (1) US5518657A (el)
EP (1) EP0542677B1 (el)
JP (1) JP3286358B2 (el)
KR (1) KR100249743B1 (el)
AT (1) ATE135423T1 (el)
AU (1) AU653271B2 (el)
BR (1) BR9204316A (el)
CA (1) CA2082202C (el)
CH (1) CH682748A5 (el)
DE (1) DE59205674D1 (el)
DK (1) DK0542677T3 (el)
ES (1) ES2084977T3 (el)
GR (1) GR3019312T3 (el)
MX (1) MX9206384A (el)
MY (1) MY110095A (el)
NZ (1) NZ245027A (el)
TW (1) TW234145B (el)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1764714B (zh) * 2003-03-24 2011-01-12 西巴特殊化学品控股有限公司 洗涤剂组合物

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH686959A5 (de) * 1992-12-22 1996-08-15 Ciba Geigy Ag Lagerstabile Formulierung von optischen Aufhellern.
GB9610832D0 (en) * 1996-05-23 1996-07-31 Ciba Geigy Ag Stilbene compounds and their use
GB9617322D0 (en) * 1996-08-17 1996-09-25 Ciba Geigy Ag Triazine derivatives and their use
JPH1081889A (ja) * 1996-09-06 1998-03-31 Bridgestone Corp 電気粘性流体用粉体
EP0835906B1 (de) * 1996-10-10 2003-11-05 Ciba SC Holding AG Dispersionen von optischen Aufhellern
GB2318360A (en) * 1996-10-15 1998-04-22 Ciba Geigy Ag Fluorescent whitening agent formulation
DE19751860C1 (de) * 1997-11-22 1999-08-19 Henkel Ecolab Gmbh & Co Ohg Waschverfahren und Zubereitung zu seiner Durchführung
GB0100610D0 (en) * 2001-01-10 2001-02-21 Clariant Int Ltd Improvements in or relating to organic compounds
WO2002097193A1 (en) * 2001-05-29 2002-12-05 Ciba Specialty Chemicals Holding Inc. A composition for the fluorescent whitening of paper
ATE540157T1 (de) * 2003-06-11 2012-01-15 Basf Se Lagerstabile, optische aufheller-formulierungen
US7666963B2 (en) * 2005-07-21 2010-02-23 Akzo Nobel N.V. Hybrid copolymers
US20070085026A1 (en) * 2005-10-14 2007-04-19 Langseder Neal E Invisible eyemark and method for orienting squeeze tube
US8674021B2 (en) * 2006-07-21 2014-03-18 Akzo Nobel N.V. Sulfonated graft copolymers
NO20073821L (no) * 2006-07-21 2008-01-22 Akzo Nobel Chemicals Int Bv Podede kopolymerer med lav molekylvekt
KR100876368B1 (ko) 2006-09-23 2008-12-29 연세대학교 산학협력단 저전압구동형 전기 형광소자 및 이의 용도
JP5564808B2 (ja) * 2009-03-24 2014-08-06 東レ株式会社 白色反射フィルム
WO2011025624A1 (en) 2009-07-31 2011-03-03 Akzo Nobel N.V. Graft copolymers
EP2665856B1 (en) * 2011-01-20 2017-03-01 Huntsman Advanced Materials (Switzerland) GmbH Formulations of fluorescent whitening agents in dispersed form
US8853144B2 (en) 2011-08-05 2014-10-07 Ecolab Usa Inc. Cleaning composition containing a polysaccharide graft polymer composition and methods of improving drainage
US8841246B2 (en) 2011-08-05 2014-09-23 Ecolab Usa Inc. Cleaning composition containing a polysaccharide hybrid polymer composition and methods of improving drainage
US8679366B2 (en) 2011-08-05 2014-03-25 Ecolab Usa Inc. Cleaning composition containing a polysaccharide graft polymer composition and methods of controlling hard water scale
US8636918B2 (en) 2011-08-05 2014-01-28 Ecolab Usa Inc. Cleaning composition containing a polysaccharide hybrid polymer composition and methods of controlling hard water scale
EP2773320B1 (en) 2011-11-04 2016-02-03 Akzo Nobel Chemicals International B.V. Hybrid dendrite copolymers, compositions thereof and methods for producing the same
MX2014005089A (es) 2011-11-04 2014-08-08 Akzo Nobel Chemicals Int Bv Copolimeros de dendrita de injerto, y metodos para producir los mismos.
US8945314B2 (en) 2012-07-30 2015-02-03 Ecolab Usa Inc. Biodegradable stability binding agent for a solid detergent
US9365805B2 (en) 2014-05-15 2016-06-14 Ecolab Usa Inc. Bio-based pot and pan pre-soak

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Publication number Priority date Publication date Assignee Title
EP0033913A2 (de) * 1980-02-07 1981-08-19 Hoechst Aktiengesellschaft Verfahren zur Herstellung von Pigmentpräparationen und ihre Verwendung

Family Cites Families (14)

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DE1902445A1 (de) * 1969-01-18 1970-07-30 Hoechst Ag Optische Aufhellungsmittel
GB1337583A (en) * 1970-03-24 1973-11-14 Ciba Geigy Uk Ltd Treatment of optical brightening agents
DE2646273A1 (de) * 1976-10-14 1978-04-20 Ciba Geigy Ag Verfahren zur herstellung von feinkristallinen aufhellern der bis- triazinylamino-stilbenreihe in der beta-kristallform
DE2834224C2 (de) * 1978-08-04 1980-02-21 Hoechst Ag, 6000 Frankfurt Farbstabile Präparationen von Waschmittelaufhellern
DE2850382A1 (de) * 1978-11-21 1980-06-04 Hoechst Ag Farbstabile waschmittelaufheller
US4363744A (en) * 1979-09-10 1982-12-14 Hoechst Aktiengesellschaft Mixtures of optical brighteners and their use for the optical brightening
EP0235080A1 (de) * 1986-01-31 1987-09-02 Ciba-Geigy Ag Färbereihilfsmittel und seine Verwendung beim Färben oder optischen Aufhellen von synthetischen stickstoffhaltigen Fasermaterialien
EP0252009B1 (de) * 1986-07-01 1990-08-01 Ciba-Geigy Ag 1,4-Distryrylbenzolverbindungen und deren Mischungen mit anderen 1,4-Distryrylbenzolverbindungen
US5035825A (en) * 1987-11-26 1991-07-30 Ciba-Geigy Corporation Stable bleaching detergents containing stilbene fluorescent whitening agents
ES2053807T3 (es) * 1987-11-27 1994-08-01 Ciba Geigy Ag Dispersion blanqueadora acuosa y procedimiento para su preparacion.
EP0321393B1 (de) * 1987-11-27 1993-02-17 Ciba-Geigy Ag Aufhellerdispersion
US5030244A (en) * 1988-06-08 1991-07-09 Ciba-Geigy Corporation Preparation of granules of dyes, optical whiteners or photoactivators from an aqueous suspension of naphthalene sulfonic acid-formaldehyde condensate dispersant
BR9000850A (pt) * 1989-02-28 1991-02-05 Ciba Geigy Ag Formulacao aclaradora estavel a armazenagem,processo para sua preparacao e aplicacao
EP0427670A1 (de) * 1989-11-07 1991-05-15 Ciba-Geigy Ag Flüssigwaschmittel

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0033913A2 (de) * 1980-02-07 1981-08-19 Hoechst Aktiengesellschaft Verfahren zur Herstellung von Pigmentpräparationen und ihre Verwendung

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1764714B (zh) * 2003-03-24 2011-01-12 西巴特殊化学品控股有限公司 洗涤剂组合物

Also Published As

Publication number Publication date
MX9206384A (es) 1993-05-01
US5518657A (en) 1996-05-21
JP3286358B2 (ja) 2002-05-27
KR100249743B1 (ko) 2000-03-15
MY110095A (en) 1998-01-27
JPH05239768A (ja) 1993-09-17
AU2820792A (en) 1993-05-13
ES2084977T3 (es) 1996-05-16
DK0542677T3 (da) 1996-04-01
CA2082202C (en) 2003-07-29
CH682748A5 (de) 1993-11-15
NZ245027A (en) 1994-10-26
EP0542677A1 (de) 1993-05-19
TW234145B (el) 1994-11-11
ATE135423T1 (de) 1996-03-15
BR9204316A (pt) 1993-05-11
CA2082202A1 (en) 1993-05-08
AU653271B2 (en) 1994-09-22
GR3019312T3 (en) 1996-06-30
KR930010170A (ko) 1993-06-22
DE59205674D1 (de) 1996-04-18

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