EP0178006B1 - Liquid detergent compositions - Google Patents
Liquid detergent compositions Download PDFInfo
- Publication number
- EP0178006B1 EP0178006B1 EP85201533A EP85201533A EP0178006B1 EP 0178006 B1 EP0178006 B1 EP 0178006B1 EP 85201533 A EP85201533 A EP 85201533A EP 85201533 A EP85201533 A EP 85201533A EP 0178006 B1 EP0178006 B1 EP 0178006B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- weight
- composition according
- detergent
- range
- active
- 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
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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/37—Mixtures of compounds all of which are anionic
-
- 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
- C11D1/02—Anionic compounds
- C11D1/04—Carboxylic acids or salts thereof
- C11D1/06—Ether- or thioether carboxylic acids
-
- 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
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
-
- 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
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic 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
- C11D1/02—Anionic compounds
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
- C11D1/29—Sulfates of polyoxyalkylene ethers
-
- 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 liquid detergent compositions and in particular to aqueous built liquid detergent compositions comprising a detergent active-based suspending system capable of suspending undissolved material.
- Aqueous built liquid detergent compositions are well known and a vast amount of formulations have been described in the prior art.
- Such compositions comprise one or more detergent-active compounds and one or more builder salts in an aqueous medium which is capable of suspending undissolved builder and/or adjuvant materials.
- compositions of the above type which have reduced sensitivity to electrolyte material and which tolerate larger quantities of such material without giving rise to unacceptable viscosities.
- FR 2 014 084 (Hoechst) describes unstructured detergent compositions which comprise fatty alcohol polyalkylene oxide carboxylate salts.
- the present invention provides an aqueous built liquid detergent composition capable of suspending particulate material, which comprises from 1% to 15% by weight of synthetic anion detergent-active material and from 5% to 30% by weight of electrolyte salts, characterized in that it comprises from 0.5-10% by weight of a fatty alcohol polyalkylene oxide carboxylate salt or a mixture of such salts according to the formula:
- R is an aliphatic hydrocarbon group having 8-20 carbon atoms or an aliphatic-aromatic hydrocarbon group having 4-20 carbon atoms in the aliphatic part; n is a number in the range of from 2 to 3 inclusive; x is a number in the range of from 1 to 16 inclusive; y is a number in the range of from 0 to 2 inclusive; and M is a cation.
- R will normally comprise a mixture of aliphatic hydrocarbon groups of different lengths which may be straight or branched, saturated or unsaturated.
- R is a straight saturated aliphatic hydrocarbon group having from 1-14 carbon atoms.
- the number of ethylene and/or propylene oxide units (x) ma range from 1-16, in particular from 1-12.
- the alkylene oxide portion comprises from 2-5 ethylene oxide units.
- M is a cation and is selected from the group of hydrogen, sodium, potassium, ammonium, mono-, di- and triethanol ammonium, the alkali metal cations being preferred.
- the fatty alcohol polyalkylene oxide carboxylate salt or a mixture of such salts is included in an amount of from 0.5-10%, partly replacing the synthetic anionic detergent-active material.
- the preferred amount depends on the rheology of the composition without the carboxylate salt compound, and the rheology which is aimed at. In general the best results are obtained when the fatty alcohol polyalkylene oxide carboxylate salt is included in an amount of from 2-5% by weight, replacing about an equivalent amount of synthetic anionic detergent active material.
- the invention relates to aqueous liquid built compositions on the basis of synthetic anionic detergent-active material and electrolyte salts.
- Suitable synthetic anionic detergent-active materials comprise the well-known anionic detergents of the alkylaryl sulphonate type, the alkyl- and alkylether sulphate type, the alkane- and alkene sulphonate type, etc. Numerous other examples can be found in Schwartz, Perry “Detergents and Surface-Active Agents", Vol. 11, 1958.
- alkylaryl sulphonates are used, in which the alkyl chain contains 10-18 carbon atoms, such as n-dodecyl benzene sulphonate, tetrapropylene benzene sulphonate, n-pentadecyl benzene sulphonate, and linear C, 2 --Cis alkylbenzene sulphonate in which the aliphatic group is obtained from cracked wax polymers, all in the form of their sodium or potassium salts.
- n-dodecyl benzene sulphonate such as n-dodecyl benzene sulphonate, tetrapropylene benzene sulphonate, n-pentadecyl benzene sulphonate, and linear C, 2 --Cis alkylbenzene sulphonate in which the aliphatic group is obtained from cracked wax polymers, all in the form of their sodium or potassium
- the total amount of synthetic anionic detergent active materials must lie within the range of 1-15% by weight, but preferably is 6-12% by weight of the total composition.
- Nonionic detergents usually consist of a hydrophobic moiety which has been reacted with an alkylene oxide.
- Suitable examples are primary or secondary, straight or branched chain Ca-Ge alcohols condensed with 1-30 moles of alkylene oxide; mono- or dialkyl phenols with an alkyl group of 9-18 carbon atoms condensed with 1-30 moles of alkylene oxide; Go-Ge fatty acid mono- or dialkylol amides condensed with 1-30 moles of alkylene oxide; block copolymers of different or identical alkylene oxides and so on.
- the alkylene oxide is ethylene oxide, but propylene oxide or a mixture of ethylene oxide and propylene oxide can also be used. Further suitable examples can be found in the text book of M. Schick "Nonionic Surfactants".
- the amount of nonionic detergent-active material which can be included in the composition ranges up to 5%, but such amounts should be less than the amount of synthetic anionic detergent active material.
- the electrolytes which are used in the present invention are those which cause partial salting out of the detergent active material.
- Typical examples are builder salts, such as the alkali metal ortho- and pyrophosphates, the alkali metal ammonium tripolyphosphates, such as sodium tripolyphosphate, the alkali metal citrates, alkyli metal salts of nitrilo triacetate and alkali metal salts of carboxy methyloxy succinate.
- builder salts such as the alkali metal ortho- and pyrophosphates, the alkali metal ammonium tripolyphosphates, such as sodium tripolyphosphate, the alkali metal citrates, alkyli metal salts of nitrilo triacetate and alkali metal salts of carboxy methyloxy succinate.
- Suitable examples of electrolytes are also buffering agents, such as the alkanol amines, in particular triethanol amine, alkali metal carbonates, alkali metal borates, alkali metal silicates, and so on.
- compositions of the invention may further contain all ingredients usually encountered in such products, such as alkali metal sulphites, for improving detergency; enzymes, either alone or in combination with enzyme stabilizers, such as polyalcohols or alkanol amines with borax; fluorescers, further builders, such as zeolites; abrasives, such as calcite; soil-suspending agents; anti-redeposition agents; hydrotropes, corrosion inhibitors; foam boosters or depressors; opacifying agents; perfumes; colouring agents; bleaching agents, optionally in combination with bleach precursors; fluorescers.
- enzymes either alone or in combination with enzyme stabilizers, such as polyalcohols or alkanol amines with borax
- fluorescers further builders, such as zeolites
- abrasives such as calcite
- soil-suspending agents such as calcite
- soil-suspending agents such as calcite
- anti-redeposition agents such as
- the products of the present invention can be prepared using conventional techniques. In this respect it has been found that it is advantageous to shear the product at the end of the production process to its maximum stable viscosity, e.g. by post-stirring or passing the product through a desintegrator or similar high-shear exerting equipment. Further shear exerted on the product thus treated during pumping and bottling does not affect the viscosity of the product.
- compositions were prepared according to the formulations listed in Table 1, having good physical stability and clearly showing the increased tolerance to high electrolyte levels.
- Akypo is the trade-name for a series of fatty alcohol polyglycolether carboxylates sold by Chem-Y, The Netherlands.
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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)
- Detergent Compositions (AREA)
Abstract
Description
- The present invention relates to liquid detergent compositions and in particular to aqueous built liquid detergent compositions comprising a detergent active-based suspending system capable of suspending undissolved material.
- Aqueous built liquid detergent compositions are well known and a vast amount of formulations have been described in the prior art. Generally such compositions comprise one or more detergent-active compounds and one or more builder salts in an aqueous medium which is capable of suspending undissolved builder and/or adjuvant materials.
- However, an important disadvantage of this type of conventional built liquid detergent is its extreme sensitivity to electrolyte level. This sensitivity results in formulation regions of physical stability and acceptable viscosity which greatly vary in magnitude and position as a function of the amount of dissolved electrolyte. In particular, sufficient quantities of the more soluble builders, such as NTA, are difficult to incorporate without rendering the liquid unstable and liable to precipitation or phase separation.
- It is therefore an object of invention to provide compositions of the above type which have reduced sensitivity to electrolyte material and which tolerate larger quantities of such material without giving rise to unacceptable viscosities.
- FR 2 014 084 (Hoechst) describes unstructured detergent compositions which comprise fatty alcohol polyalkylene oxide carboxylate salts.
- It has now been found that inclusion of relatively small quantities of specific fatty alcohol poly- glycoletherderived anionic surfactants, replacing part of the conventional anionic surfactant, reduces the sensitivity of the rheology to electrolyte materials, in particular, to builder and simple electrolyte salts.
- Accordingly, the present invention provides an aqueous built liquid detergent composition capable of suspending particulate material, which comprises from 1% to 15% by weight of synthetic anion detergent-active material and from 5% to 30% by weight of electrolyte salts, characterized in that it comprises from 0.5-10% by weight of a fatty alcohol polyalkylene oxide carboxylate salt or a mixture of such salts according to the formula:
- wherein R is an aliphatic hydrocarbon group having 8-20 carbon atoms or an aliphatic-aromatic hydrocarbon group having 4-20 carbon atoms in the aliphatic part; n is a number in the range of from 2 to 3 inclusive; x is a number in the range of from 1 to 16 inclusive; y is a number in the range of from 0 to 2 inclusive; and M is a cation.
- R will normally comprise a mixture of aliphatic hydrocarbon groups of different lengths which may be straight or branched, saturated or unsaturated. Preferably R is a straight saturated aliphatic hydrocarbon group having from 1-14 carbon atoms.
- The polyalkylene oxide portion (OCnH2n)x preferably comprises only ethylene oxide units (n=2) but also propylene oxide or mixtures of propylene oxide and ethylene oxide are suitable (2<ns3). The number of ethylene and/or propylene oxide units (x) ma range from 1-16, in particular from 1-12. Preferably the alkylene oxide portion comprises from 2-5 ethylene oxide units.
- The carboxylate portion ((CH2)y-COOM) preferably comprises no alkyl chain (y=0), but short alkyl chains such as methylene and ethylene are also suitable. M is a cation and is selected from the group of hydrogen, sodium, potassium, ammonium, mono-, di- and triethanol ammonium, the alkali metal cations being preferred.
- In the detergent compositions according to the present invention the fatty alcohol polyalkylene oxide carboxylate salt or a mixture of such salts is included in an amount of from 0.5-10%, partly replacing the synthetic anionic detergent-active material. The preferred amount depends on the rheology of the composition without the carboxylate salt compound, and the rheology which is aimed at. In general the best results are obtained when the fatty alcohol polyalkylene oxide carboxylate salt is included in an amount of from 2-5% by weight, replacing about an equivalent amount of synthetic anionic detergent active material.
- The invention relates to aqueous liquid built compositions on the basis of synthetic anionic detergent-active material and electrolyte salts. Suitable synthetic anionic detergent-active materials comprise the well-known anionic detergents of the alkylaryl sulphonate type, the alkyl- and alkylether sulphate type, the alkane- and alkene sulphonate type, etc. Numerous other examples can be found in Schwartz, Perry "Detergents and Surface-Active Agents", Vol. 11, 1958.
- Preferably alkylaryl sulphonates are used, in which the alkyl chain contains 10-18 carbon atoms, such as n-dodecyl benzene sulphonate, tetrapropylene benzene sulphonate, n-pentadecyl benzene sulphonate, and linear C,2--Cis alkylbenzene sulphonate in which the aliphatic group is obtained from cracked wax polymers, all in the form of their sodium or potassium salts.
- The total amount of synthetic anionic detergent active materials must lie within the range of 1-15% by weight, but preferably is 6-12% by weight of the total composition.
- Although the anionic materials are the major detergent-active constituents, small amounts of other detergent-active materials can be tolerated, in particular nonionic detergent-active materials. Nonionic detergents usually consist of a hydrophobic moiety which has been reacted with an alkylene oxide.
- Suitable examples are primary or secondary, straight or branched chain Ca-Ge alcohols condensed with 1-30 moles of alkylene oxide; mono- or dialkyl phenols with an alkyl group of 9-18 carbon atoms condensed with 1-30 moles of alkylene oxide; Go-Ge fatty acid mono- or dialkylol amides condensed with 1-30 moles of alkylene oxide; block copolymers of different or identical alkylene oxides and so on. Usually the alkylene oxide is ethylene oxide, but propylene oxide or a mixture of ethylene oxide and propylene oxide can also be used. Further suitable examples can be found in the text book of M. Schick "Nonionic Surfactants".
- The amount of nonionic detergent-active material which can be included in the composition ranges up to 5%, but such amounts should be less than the amount of synthetic anionic detergent active material. The electrolytes which are used in the present invention are those which cause partial salting out of the detergent active material.
- Typical examples are builder salts, such as the alkali metal ortho- and pyrophosphates, the alkali metal ammonium tripolyphosphates, such as sodium tripolyphosphate, the alkali metal citrates, alkyli metal salts of nitrilo triacetate and alkali metal salts of carboxy methyloxy succinate.
- Suitable examples of electrolytes are also buffering agents, such as the alkanol amines, in particular triethanol amine, alkali metal carbonates, alkali metal borates, alkali metal silicates, and so on.
- The compositions of the invention may further contain all ingredients usually encountered in such products, such as alkali metal sulphites, for improving detergency; enzymes, either alone or in combination with enzyme stabilizers, such as polyalcohols or alkanol amines with borax; fluorescers, further builders, such as zeolites; abrasives, such as calcite; soil-suspending agents; anti-redeposition agents; hydrotropes, corrosion inhibitors; foam boosters or depressors; opacifying agents; perfumes; colouring agents; bleaching agents, optionally in combination with bleach precursors; fluorescers.
- The products of the present invention can be prepared using conventional techniques. In this respect it has been found that it is advantageous to shear the product at the end of the production process to its maximum stable viscosity, e.g. by post-stirring or passing the product through a desintegrator or similar high-shear exerting equipment. Further shear exerted on the product thus treated during pumping and bottling does not affect the viscosity of the product.
- The invention will now be further illustrated by way of example, in which all percentages are by weight of the final composition.
-
- Akypo RLM 25 : sodium lauryl poly (2.5) ethylene oxide carboxylate
- Akypo RLM 45 : sodium lauryl poly (4.5.) ethylene oxide carboxylate
- Akypo RLM 100: sodium lauryl poly (10) ethylene oxide carboxylate
- Akypo L 140 : sodium lauryl poly (14) ethylene oxide carboxylate
- Akypo RLM 160: sodium lauryl poly (16) ethylene oxide carboxylate
- Akypo O 60: sodium oleyl poly (6) ethylene oxide carboxylate
Claims (9)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT85201533T ATE56470T1 (en) | 1984-10-12 | 1985-09-25 | LIQUID DETERGENT COMPOSITIONS. |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB8425785 | 1984-10-12 | ||
GB848425785A GB8425785D0 (en) | 1984-10-12 | 1984-10-12 | Liquid detergent compositions |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0178006A2 EP0178006A2 (en) | 1986-04-16 |
EP0178006A3 EP0178006A3 (en) | 1988-07-20 |
EP0178006B1 true EP0178006B1 (en) | 1990-09-12 |
Family
ID=10568081
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP85201533A Expired - Lifetime EP0178006B1 (en) | 1984-10-12 | 1985-09-25 | Liquid detergent compositions |
Country Status (9)
Country | Link |
---|---|
EP (1) | EP0178006B1 (en) |
JP (1) | JPS6197395A (en) |
AT (1) | ATE56470T1 (en) |
AU (1) | AU579191B2 (en) |
BR (1) | BR8505035A (en) |
CA (1) | CA1232817A (en) |
DE (1) | DE3579658D1 (en) |
GB (1) | GB8425785D0 (en) |
ZA (1) | ZA857798B (en) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4797225A (en) * | 1986-09-08 | 1989-01-10 | Colgate-Palmolive Company | Nonaqueous liquid nonionic laundry detergent composition containing an alkali metal dithionite or sulfite reduction bleaching agent and method of use |
DE3905938A1 (en) * | 1989-02-25 | 1990-08-30 | Huels Chemische Werke Ag | DETERGENT COMPOSITIONS WITH INCREASED VISCOSITY |
US7037884B2 (en) | 1994-02-23 | 2006-05-02 | Ecolab Inc. | Alkaline cleaners based on alcohol ethoxy carboxylates |
DE19581539B4 (en) * | 1994-02-23 | 2009-09-17 | Ecolab Inc., St. Paul | Alkaline cleaners based on alcohol ethoxy carboxylates |
NL9401510A (en) * | 1994-09-16 | 1996-05-01 | Chem Y | Surfactant composition, surfactant concentrate in liquid form, and aqueous bleaching agent having increased viscosity and cleaning activity |
TW294720B (en) * | 1994-09-30 | 1997-01-01 | Unilever Nv | |
DE19852973C1 (en) * | 1998-11-17 | 2000-07-20 | Cognis Deutschland Gmbh | Production of low-viscosity aqueous detergent preparations |
CN104159562B (en) * | 2012-03-02 | 2016-12-28 | 花王株式会社 | Composition of skin cleanser |
MY167793A (en) * | 2012-03-02 | 2018-09-26 | Kao Corp | Skin cleanser composition |
JP6121098B2 (en) * | 2012-03-07 | 2017-04-26 | 花王株式会社 | Skin cleanser composition |
WO2018127390A1 (en) * | 2017-01-06 | 2018-07-12 | Unilever N.V. | Stain removing composition |
WO2018206197A1 (en) * | 2017-05-10 | 2018-11-15 | Unilever Plc | Laundry detergent composition |
WO2018206202A1 (en) | 2017-05-10 | 2018-11-15 | Unilever Plc | Laundry detergent composition |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2014084A1 (en) * | 1968-07-31 | 1970-04-10 | Hoechst Ag | |
NL7201735A (en) * | 1971-02-16 | 1972-08-18 | ||
FR2436213A1 (en) * | 1978-09-13 | 1980-04-11 | Oreal | COMPOSITION FOR TREATING FIBROUS MATERIALS BASED ON CATIONIC AND ANIONIC POLYMERS |
US4443362A (en) * | 1981-06-29 | 1984-04-17 | Johnson & Johnson Baby Products Company | Detergent compounds and compositions |
-
1984
- 1984-10-12 GB GB848425785A patent/GB8425785D0/en active Pending
-
1985
- 1985-09-25 EP EP85201533A patent/EP0178006B1/en not_active Expired - Lifetime
- 1985-09-25 DE DE8585201533T patent/DE3579658D1/en not_active Expired - Fee Related
- 1985-09-25 AT AT85201533T patent/ATE56470T1/en active
- 1985-10-04 CA CA000492347A patent/CA1232817A/en not_active Expired
- 1985-10-07 AU AU48344/85A patent/AU579191B2/en not_active Ceased
- 1985-10-09 ZA ZA857798A patent/ZA857798B/en unknown
- 1985-10-10 BR BR8505035A patent/BR8505035A/en not_active IP Right Cessation
- 1985-10-11 JP JP60226672A patent/JPS6197395A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
BR8505035A (en) | 1986-07-29 |
GB8425785D0 (en) | 1984-11-21 |
AU579191B2 (en) | 1988-11-17 |
JPH0357958B2 (en) | 1991-09-03 |
ATE56470T1 (en) | 1990-09-15 |
ZA857798B (en) | 1987-06-24 |
CA1232817A (en) | 1988-02-16 |
DE3579658D1 (en) | 1990-10-18 |
JPS6197395A (en) | 1986-05-15 |
AU4834485A (en) | 1986-04-17 |
EP0178006A2 (en) | 1986-04-16 |
EP0178006A3 (en) | 1988-07-20 |
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