EP0507478B1 - Wäscheweichmacherzusammensetzung - Google Patents

Wäscheweichmacherzusammensetzung Download PDF

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Publication number
EP0507478B1
EP0507478B1 EP92302452A EP92302452A EP0507478B1 EP 0507478 B1 EP0507478 B1 EP 0507478B1 EP 92302452 A EP92302452 A EP 92302452A EP 92302452 A EP92302452 A EP 92302452A EP 0507478 B1 EP0507478 B1 EP 0507478B1
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EP
European Patent Office
Prior art keywords
composition
fabric softening
weight
agent
nonionic stabilising
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.)
Revoked
Application number
EP92302452A
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English (en)
French (fr)
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EP0507478A1 (de
Inventor
Simon Richard Unilever Research Ellis
Graham Andrew Unilever Research Turner
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.)
Unilever PLC
Unilever NV
Original Assignee
Unilever PLC
Unilever NV
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Application filed by Unilever PLC, Unilever NV filed Critical Unilever PLC
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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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/835—Mixtures of non-ionic with cationic compounds
    • 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
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/001—Softening compositions
    • C11D3/0015—Softening compositions liquid
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/72—Ethers of polyoxyalkylene glycols

Definitions

  • the present invention relates to fabric softening compositions, in particular the invention relates to aqueous dispersions of biodegradable fabric softening compositions comprising a water insoluble cationic fabric softening agent and a nonionic stabilising agent suitable as rinse-added fabric softener compositions.
  • Rinse added fabric softener compositions are well known. Typically such compositions contain a water insoluble quaternary ammonium fabric softening agent dispersed in water at a level of softening agent up to 7% by weight in which case the compositions are considered dilute, or at levels from 7% to 50% in which case the compositions are considered concentrates.
  • fabric softening compositions desirably have other benefits. One is the ability to confer soil release properties to fabrics, particularly those woven from polyester fibres.
  • viscosity control agents In the past physical stability of rinse added fabric softener compositions has been improved by the addition of viscosity control agents or anti-gelling agents.
  • viscosity control agents For example in EP 13780 (Procter and Gamble) viscosity control agents are added to certain concentrated compositions. The agents may include C 10 -C 18 fatty alcohols.
  • EP 280550 More recently in EP 280550 (Unilever) it has been proposed to improve the physical stability of dilute compositions comprising biodegradable, ester-linked quaternary ammonium compounds and fatty acid by the addition of nonionic surfactants.
  • compositions comprising biodegradable ester-linked quaternary ammonium compounds the problem of physical instability is more acute than with traditional quaternary ammonium compounds.
  • a nonionic emulsifier/stabiliser is added to a concentrate comprising an ester-linked quaternary ammonium compound to form a viscous gel.
  • the stabiliser is a C 12 to C 14 alcohol ethoxylated with 9 molecules of ethylene oxide. The degree of branching of the alcohol is not, however, mentioned.
  • EP-A-0,293,953 discloses mono-ester analogs of ditallow dimethyl ammonium chloride as fabric softeners. The presence of only one ester group is said to provide hydrolytic stability to the softeners.
  • the softeners may be stabilized with standard emulsifiers, including nonionics.
  • EP-A-0,309,052 discloses fabric softening compositions comprising a quaternary ammonium salt which has at least one ester linkage and a linear alkoxylated alcohol to stabilize against settling.
  • the alcohol is alkoxylated with between about 1 and 10, preferably 2 to 5, moles of ethylene or propylene oxide.
  • EP-A-0,346,634 discloses a liquid laundry conditioner containing a quaternary ammonium compound with two 2-acyloxyalkyl groups, and a fatty acid.
  • the composition may also include nonionic dispersing agents such as the condensation products of C 10-20 alcohols with from 4 to 40 moles of ethylene or propylene oxide. The degree of branching of the alcohols is not mentioned.
  • EP-A-0,331,237 discloses an aqueous fabric conditioning composition
  • a fabric softener which may be an ester-containing quaternary ammonium compound
  • a hydrophobically modified nonionic cellulose ether may also be included.
  • Certain nonionic stabilising agents not only stabilise concentrated compositions comprising biodegradable quaternary ammonium compounds but are also environmentally friendly, in that they show acceptable biodegradability and are not substantially toxic in aquatic systems.
  • Soil release properties are generally imparted to fabrics by the use of separate soil-release agents, usually a high molecular weight polymer, in a detergent composition or separate treatment.
  • separate soil-release agents usually a high molecular weight polymer
  • a cationic polymeric soil release agent for use in a fabric conditioning composition.
  • a disadvantage of such compositions is that the soil release agent increases the number of components in the formulation, increasing cost and making the product less environmentally acceptable.
  • fabric softening compositions comprising biodegradable ester-linked quaternary ammonium compounds may confer improved soil release properties to fabrics.
  • a fabric softening composition comprising a water insoluble cationic fabric softening agent and a nonionic stabilising agent characterised in that the water insoluble cationic fabric softening agent is a biodegradable quaternary ammonium material as defined below and the nonionic stabilising agent is
  • nonionic stabilising agent is a linear C 8 to C 22 alcohol alkoxylated with 10 to 20 moles of alkylene oxide
  • compositions of the invention are liquids comprising an aqueous base.
  • ester-linked quaternary ammonium material for use in the compositions according to the invention can be represented either by the formula: wherein each R 1 group is independently selected from C 1-4 alkyl, alkenyl or hydroxyalkyl groups; each R 2 group is independently selected from C 8-28 , preferably C 12-28 , alkyl or alkenyl groups; T is and n is an integer from 0-5, or by the formula: wherein R 1 , n and R 2 are as defined above.
  • Preferred materials of this class and their method of preparation are, for example, described in US 4 137 180 (Lever Brothers).
  • these materials comprise small amounts of the corresponding monoester as described in US 4 137 180 for example 1-tallowoxy, 2-hydroxytrimethyl ammonium propane chloride.
  • a fabric softening composition comprising a water insoluble cationic fabric softening agent which is a biodegradable quaternary ammonium material having at least one ester link, of a nonionic stabilising agent which is either:
  • the level of ester linked quaternary ammonium compounds, in the compositions of the invention is at least 1% by weight of the composition, more preferably more than 3% by weight of the composition; especially interesting are concentrated compositions which comprise more than 7% of ester-linked quaternary ammonium compound.
  • the level of ester-linked quaternary ammonium compounds preferably is between 1% and 80% by weight, more preferably 3% to 50%, most preferably 8% to 50%.
  • Suitable nonionic stabilisers which can be used include the condensation products of C 8 - C 22 primary linear alcohols with 10 to 20 moles of ethylene oxide.
  • linear alcohol means a primary alcohol attached directly to a hydrocarbon backbone structure.
  • An HLB of greater than about 12 gives rise to an acceptable acute aquatic toxicity value of >1mg/l;EC 50 48 hours for daphnia and algae and EC 50 96 hours for fish.
  • the selection of linear alcohols and the use of 20 moles or less of ethylene oxide gives acceptable biodegradability to the nonionic stabiliser.
  • the use of nonionic stabilisers with more than 20 ethylene oxide units will also provide the stability benefit .
  • the alcohols may be saturated or unsaturated.
  • the nonionic stabiliser has an HLB of between 10 and 20, more preferably 12 and 20.
  • the level of nonionic stabiliser is within the range from 0.1 to 10% by weight, more preferably from 0.5 to 5% by weight, most preferably from 1 to 4% by weight.
  • the mole ratio of the quaternary ammonium compound to the nonionic stabilising agent is within the range from 40:1 to about 1:1, preferably within the range from 18:1 to about 3:1.
  • the composition can also contain fatty acids for example C 8 - C 24 alkyl or alkenyl monocarboxylic acids or polymers thereof.
  • fatty acids for example C 8 - C 24 alkyl or alkenyl monocarboxylic acids or polymers thereof.
  • saturated fatty acids are used, in particular, hardened tallow C 16 -C 18 fatty acids.
  • the fatty acid is non-saponified, more preferably the fatty acid is free for example oleic acid, lauric acid or tallow fatty acid.
  • the level of fatty acid material is preferably more than 0.1% by weight, more preferably more than 0.2% by weight. Especially preferred are concentrates comprising from 0.5 to 20% by weight of fatty acid, more preferably 1% to 10% by weight.
  • the weight ratio of quaternary ammonium material to fatty acid material is preferably from 10:1 to 1:10.
  • compositions of the invention preferably have a pH of more than 2.0, more preferably less than 5.
  • the composition can also contain one or more optional ingredients, selected from non-aqueous solvents, pH buffering agents, perfumes, perfume carriers, fluorescers, colourants, hydrotropes, antifoaming agents, antiredeposition agents, enzymes, optical brightening agents, opacifiers, anti-shrinking agents, anti-wrinkle agents, anti-spotting agents, germicides, fungicides, anti-oxidants, anti-corrosion agents, drape imparting agents, antistatic agents and ironing aids.
  • optional ingredients selected from non-aqueous solvents, pH buffering agents, perfumes, perfume carriers, fluorescers, colourants, hydrotropes, antifoaming agents, antiredeposition agents, enzymes, optical brightening agents, opacifiers, anti-shrinking agents, anti-wrinkle agents, anti-spotting agents, germicides, fungicides, anti-oxidants, anti-corrosion agents, drape imparting agents, antistatic agents and ironing aids.
  • composition may also contain nonionic fabric softening agents such as lanolin and derivatives thereof.
  • Liquid fabric softening compositions were made as follows.
  • the cationic fabric softening agent, fatty acid and nonionic stabilising agent where appropriate were premixed and heated together to form a clear melt.
  • the molten mixture thus formed was added over a period of at least one minute, to water at 70°C to 80°C with constant stirring to form a dispersion.
  • the viscosity of the compositions was measured by Haake rotoviscometer following 21 days storage at ambient temperature or at 5°C.
  • composition A fabric softening compositions comprising conventional quaternary ammonium compounds do not show physical instability on short term storage at 5°C
  • compositions comprising ester-linked quaternaries and fatty acid composition E
  • composition E composition E
  • Liquid fabric softening compositions as given below were made as described in Example 1.
  • the soil release properties imparted to polyester test pieces by treatment with the compositions was assessed by measuring the change in reflectance following staining and a subsequent wash in a proprietary detergent composition.
  • the pieces were first rinsed for 5 minutes in 1 litre of 14°FH water containing 0.67 ml of either composition.
  • the pieces were then line dried and stained with 100 micro litres of olive oil containing 0.06% sudan red dye.
  • the stain was allowed to spread for a minimum of two days following which the reflectance of the stained piece (R 1 ) was measured using an ICS micromatch.
  • Formulation B corresponds to a commercially available fabric softening composition, currently sold in the UK by Lever under the trade mark COMFORT. 1, 2, 3 and 4 are as in Example 1.
  • composition B shows a smaller soil release benefit than compositions according to the invention (Composition A).
  • compositions according to the invention are as follows: Composition % by weight A B C HTTMAPC 2 11.6 11.6 11.6 Fatty acid 3 1.9 1.9 1.9 Tallow 11EO 4 - 2.5 - Tallow Alcohol 7 1.5 - - Tallow 15EO 8 - - 1.5 Isopropyl alcohol 1.6 1.6 1.6 Glycerol 1.6 1.6 1.6 Perfume, Dye + minors 0.8 0.8 0.8 Water to balance Notes 2, 3, 4 and 7 are as in Example 1 8. is tallow alcohol ethoxylated with 15 moles of ethylene oxide.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Claims (13)

  1. Textilweichmachendes Mittel, umfassend ein wasserunlösliches, kationisches, textilweichmachendes Mittel und ein nichtionisches, stabilisierendes Mittel, dadurch gekennzeichnet, daß das wasserunlösliche, kationische, textilweichmachende Mittel ein bioabbaubares, quaternäres Ammoniummaterial ist, wiedergegeben entweder durch die Formel
    Figure imgb0015
        worin jede Gruppe R1 unabhängig ausgewählt ist aus C1-4-Alkyl-, Alkenyl- oder Hydroxyalkylgruppen; jede Gruppe R2 unabhängig voneinander ausgewählt ist aus C8-28-Alkyl- oder Alkenylgruppen;
    Figure imgb0016
     darstellt und
       n eine ganze Zahl von 0 bis 5 ist
       oder durch die Formel:
    Figure imgb0017
        worin R1, n und R2 wie vorstehend definiert sind und dadurch, daß das nichtionische Stabilisierungsmittel
    i. ein linearer C8- bis C22-Alkohol, alkoxyliert mit 10 bis 20 Mol Alkylenoxid oder
    ii. ein C10- bis C20-Alkohol oder Gemische davon ist.
  2. Mittel nach Anspruch 1, wobei das nichtionische, stabilisierende Mittel ein linearer C8- bis C22-Alkohol, alkoxyliert mit 10 bis 20 Mol Alkylenoxid, ist.
  3. Mittel nach Anspruch 1 oder Anspruch 2, dadurch gekennzeichnet, daß das Mittel mindestens 1 Gew.-% des quaternären Ammoniummaterials umfaßt.
  4. Mittel nach einem vorangehenden Anspruch, dadurch gekennzeichnet, daß das Mittel 0,1 bis 10 Gew.-% des nichtionischen, stabilisierenden Mittels umfaßt.
  5. Mittel nach einem vorangehenden Anspruch, dadurch gekennzeichnet, daß das Mittel auch mehr als 0,1 Gew.-% eines Fettsäurematerials umfaßt.
  6. Mittel nach einem vorangehenden Anspruch, dadurch gekennzeichnet, daß das Mittel 3 bis 50 Gew.-% des quaternären Ammoniummaterials, 0,5 bis 5 Gew.-% des nichtionischen, stabilisierenden Mittels und 0,5 bis 20 Gew.-% des Fettsäurematerials umfaßt.
  7. Mittel nach einem vorangehenden Anspruch, dadurch gekennzeichnet, daß das nichtionische, stabilisierende Mittel einen HLB-Wert zwischen 10 und 20 aufweist.
  8. Mittel nach Anspruch 7, dadurch gekennzeichnet, daß das nichtionische, stabilisierende Mittel einen HLB-Wert zwischen 12 und 20 aufweist.
  9. Verfahren zur Herstellung eines flüssigen, textilweichmachenden Mittels nach einem der Ansprüche 1 bis 8, umfassend die Schritte
    i. Vermischen und Erwärmen des kationischen, textilweichmachenden Mittels und des nichtionischen, stabilisierenden Mittels unter Bildung einer Schmelze und
    ii. Dispergieren der Schmelze in Wasser.
  10. Verwendung in einem textilweichmachenden Mittel, umfassend ein wasserunlösliches, kationisches, textilweichmachendes Mittel, das ein bioabbaubares, quaternäres Ammoniummaterial mit mindestens einer Esterbindung ist, eines nichtionischen, stabilisierenden Mittels, das entweder:
    i. ein linearer C8- bis C22-Alkohol, alkoxyliert mit 10 bis 20 Mol Alkylenoxid oder
    ii. C10- bis C20-Alkohol oder Gemische davon ist, zur Verbesserung der Stabilität des Mittels unterhalb der Umgebungstemperatur.
  11. Verwendung nach Anspruch 10, wobei das nichtionische, stabilisierende Mittel ein C8- bis C22-Alkohol, alkoxyliert mit 10 bis 20 Mol Alkylenoxid, ist.
  12. Verwendung nach Anspruch 10 oder Anspruch 11, wobei das nichtionische, stabilisierende Mittel in dem Mittel bei einer Konzentration zwischen 0,1 und 10 Gew.-% verwendet wird.
  13. Verwendung nach einem der Ansprüche 10 bis 12, wobei das kationische, textilweichmachende Mittel wiedergegeben wird entweder durch die Formel:
    Figure imgb0018
        worin jede Gruppe R1 unabhängig ausgewählt ist aus C1-4-Alkyl-, Alkenyl- oder Hydroxyalkylgruppen; jede Gruppe R2 unabhängig voneinander ausgewählt ist aus C8-28-Alkyl- oder Alkenylgruppen;
    T
    Figure imgb0019
     darstellt und
       n eine ganze Zahl von 0 bis 5 ist
       oder durch die Formel:
    Figure imgb0020
        worin R1, n und R2 wie vorstehend definiert sind.
EP92302452A 1991-03-25 1992-03-20 Wäscheweichmacherzusammensetzung Revoked EP0507478B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB919106308A GB9106308D0 (en) 1991-03-25 1991-03-25 Fabric softening composition
GB9106308 1991-03-25

Publications (2)

Publication Number Publication Date
EP0507478A1 EP0507478A1 (de) 1992-10-07
EP0507478B1 true EP0507478B1 (de) 1996-06-05

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ID=10692165

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EP92302452A Revoked EP0507478B1 (de) 1991-03-25 1992-03-20 Wäscheweichmacherzusammensetzung
EP92302453A Expired - Lifetime EP0506312B1 (de) 1991-03-25 1992-03-20 Verwendung von Wäscheweichmachern

Family Applications After (1)

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EP92302453A Expired - Lifetime EP0506312B1 (de) 1991-03-25 1992-03-20 Verwendung von Wäscheweichmachern

Country Status (9)

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EP (2) EP0507478B1 (de)
JP (1) JP2937306B2 (de)
AU (1) AU652429B2 (de)
BR (1) BR9201017A (de)
CA (1) CA2063463C (de)
DE (2) DE69211203T2 (de)
ES (2) ES2083084T3 (de)
GB (1) GB9106308D0 (de)
ZA (1) ZA922173B (de)

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GB9115255D0 (en) * 1991-07-15 1991-08-28 Unilever Plc Fabric softening composition
GB9301728D0 (en) * 1993-01-28 1993-03-17 Unilever Plc Fabric softening composition
CZ276994A3 (en) * 1992-05-12 1995-04-12 Procter & Gamble Concentrated agent for softening fabrics and containing biodegradable fabric softeners
ATE150481T1 (de) * 1992-06-10 1997-04-15 Procter & Gamble Stabile, biologisch abbaubare gewebeweichmacherzusammensetzungen
CN1066188C (zh) * 1993-03-01 2001-05-23 普罗格特-甘布尔公司 浓的可生物降解季铵织物柔软剂组合物和含有中等碘值不饱和脂肪酸链的化合物
US5750491A (en) * 1993-08-02 1998-05-12 The Procter & Gamble Company Super concentrate emulsions with fabric actives
US6559117B1 (en) 1993-12-13 2003-05-06 The Procter & Gamble Company Viscosity stable concentrated liquid fabric softener compositions
US5413723A (en) * 1993-12-17 1995-05-09 Munteanu; Marina A. Use of special surfactants to control viscosity in fabric softeners
GB9406824D0 (en) * 1994-04-07 1994-06-01 Unilever Plc Fabric softening composition
AU702743B2 (en) * 1994-04-07 1999-03-04 Unilever Plc Fabric softening composition
AU2399295A (en) * 1994-04-29 1995-11-29 Procter & Gamble Company, The Cellulase fabric-conditioning compositions
WO1995031524A2 (en) * 1994-05-18 1995-11-23 The Procter & Gamble Company Concentrated biodegradable fabric softener compositions
US5445747A (en) * 1994-08-05 1995-08-29 The Procter & Gamble Company Cellulase fabric-conditioning compositions
US5503756A (en) * 1994-09-20 1996-04-02 The Procter & Gamble Company Dryer-activated fabric conditioning compositions containing unsaturated fatty acid
US5460736A (en) * 1994-10-07 1995-10-24 The Procter & Gamble Company Fabric softening composition containing chlorine scavengers
US5474690A (en) * 1994-11-14 1995-12-12 The Procter & Gamble Company Concentrated biodegradable quaternary ammonium fabric softener compositions containing intermediate iodine value fatty acid chains
GB9503596D0 (en) * 1995-02-23 1995-04-12 Unilever Plc Cleaning composition comprising quaternised poly-dimethylsiloxane and nonionic surfactant
GB9517433D0 (en) * 1995-08-25 1995-10-25 Unilever Plc Soil release agent and its use in fabric conditioning compositions
GB9526182D0 (en) * 1995-12-21 1996-02-21 Unilever Plc Fabric softening composition
GB2313379A (en) * 1996-05-23 1997-11-26 Unilever Plc A detergent composition comprising perfume
BR9701287A (pt) * 1997-03-14 1998-11-10 Unilever Nv Composição de tratamento de tecidos na lavagem e processo para tratar tecidos para proporcionar aos mesmos propriedades de repelência à sujeira
GB0121802D0 (en) 2001-09-10 2001-10-31 Unilever Plc Fabric conditioning compositions
EP1354872A1 (de) 2002-04-17 2003-10-22 Kao Corporation Aminsalze von Schwefelsäureestern, Aminsalze von Sulfonsäuren, ihre Herstellung und Weichspüler
DE602004015129D1 (de) * 2003-10-16 2008-08-28 Procter & Gamble Wässrige zusammensetzungen mit vesikeln mit gewisser vesikeldurchlässigkeit
US7655609B2 (en) 2005-12-12 2010-02-02 Milliken & Company Soil release agent
US9926516B2 (en) 2014-06-05 2018-03-27 The Procter & Gamble Company Mono alcohols for low temperature stability of isotropic liquid detergent compositions

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DE3818061A1 (de) * 1988-05-27 1989-12-07 Henkel Kgaa Fluessiges, waessriges waeschenachbehandlungsmittel

Also Published As

Publication number Publication date
ES2083084T3 (es) 1996-04-01
AU652429B2 (en) 1994-08-25
EP0506312A1 (de) 1992-09-30
CA2063463A1 (en) 1992-09-26
AU1312592A (en) 1992-10-01
DE69207624T2 (de) 1996-05-30
GB9106308D0 (en) 1991-05-08
CA2063463C (en) 1999-04-27
BR9201017A (pt) 1992-11-24
DE69207624D1 (de) 1996-02-29
ES2088542T3 (es) 1996-08-16
JPH05106166A (ja) 1993-04-27
ZA922173B (en) 1993-09-27
EP0506312B1 (de) 1996-01-17
DE69211203T2 (de) 1996-10-10
DE69211203D1 (de) 1996-07-11
EP0507478A1 (de) 1992-10-07
JP2937306B2 (ja) 1999-08-23

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