EP0212723A2 - Built liquid detergents - Google Patents
Built liquid detergents Download PDFInfo
- Publication number
- EP0212723A2 EP0212723A2 EP86201319A EP86201319A EP0212723A2 EP 0212723 A2 EP0212723 A2 EP 0212723A2 EP 86201319 A EP86201319 A EP 86201319A EP 86201319 A EP86201319 A EP 86201319A EP 0212723 A2 EP0212723 A2 EP 0212723A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- succinate
- citrate
- weight
- composition according
- builder
- 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.)
- Granted
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
- C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
-
- 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
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2075—Carboxylic acids-salts thereof
- C11D3/2082—Polycarboxylic acids-salts thereof
-
- 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
- C11D1/08—Polycarboxylic acids containing no nitrogen or sulfur
-
- 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
- C11D3/16—Organic compounds
- C11D3/20—Organic compounds containing oxygen
- C11D3/2075—Carboxylic acids-salts thereof
- C11D3/2086—Hydroxy carboxylic acids-salts thereof
Definitions
- the subject matter of this invention relates to liquid laundry detergent compositions which contain alkyl-or alkenyl-succinates, in combination with citrates, as detergency builder ingredients.
- UK 1.293.753 describes solid laundry detergent compositions preferably comprising 20 % to 40 % of such succinates as builders.
- carboxylate materials of various types in solid and liquid cleaners are well-known; see UK 1.514.276 for amine soap mixtures; UK 1.429.143 for zeolite/polycarboxylate mixtures: US 2.264.103 for citrate and other carboxylate plus soap mixtures; US 3.634.392 for polysaccharidic carboxylate detergency builders; US 3.898.187 for various sulfur-succinates in dishwashing detergents; and UK 1.400.898 for use with clay softeners.
- the present invention relates to homogeneous detergent compositions designed especially for laundering fabrics.
- Said compositions are commonly referred to as “heavy-duty liquids” or “HDL's”, since they are designed to remove even the "heaviest” soil loads from fabrics when used in a conventional laundering operation.
- compositions herein comprise fluid carrier medium, a detersive surfactant or mixtures of detersive surfactants, and optionally, detersive enzymes and other conventional detersive ingredients, characterized in that said compositions contain:
- the invention comprises a method for laundering fabrics by agitating said fabrics in a aqueous laundering liquor, said liquor containing at least 0.05 % by weight of a composition of the foregoing type.
- the essential components of the present compositions are the alkyl- or alkenyl-succinate, the citrate builder, and the detersive surfactant.
- the optional detersive adjunct ingredients, as well as the fluid carrier medium, etc., are all well-known to workers in this field.
- Succinate Builder The preferred builders herein are of the general formula R-CH(COOH)CH2(COOH), i.e., derivatives of succinic acid, wherein R is C10-C16 alkyl or alkenyl, preferably C12-C16.
- succinate builders are preferably used in the form of their water-soluble salts, including the sodium, potassium, ammonium and alkanolammonium salts (e.g., mono-, di-, or tri-ethanolammonium).
- succinate builders include: lauryl succinate, myristyl succinate, palmityl succinate, 2-dodecenyl succinate (preferred), 2-tetradecenyl succinate, and the like.
- the citrate builder employed in the practice of this invention includes any water-soluble salt of citric acid.
- Such salts include, for example, sodium, potassium, ammonium or alkanolammonium salts, as in the case of the succinate builders already described.
- the citrate builders are unique in their ability to prevent undue fabric build-up by the succinate builders.
- a highly preferred HDL composition herein comprises a mixture of 3.7 % citrate (specified as citric acid) and 10.4 % 2-dodecenyl succinate as the builder, and is formulated at a pH range of 7.3 to 8.6.
- the detergent compositions of this invention will contain organic surface-active agents ("surfactants") to provide the cleaning benefits associated with the use of such materials.
- HDL which contains an effective amount of detersive surfactant.
- the HDL's it is highly desirable for the HDL's to contain at least 5 % , preferably 7 % to 12 % of an anionic surfactant to give true "heavy-duty" laundering performance on a wide spectrum of soils and stains.
- Anionic detersive surfactants useful herein include the well-known synthetic alkyl benzene sulfonates (which are highly preferred in the present HDL's) alkyl- and alkylether sulfates, paraffin sulfonates, olefin sulfonates, alpha-sulfonates of fatty acids and of fatty acid esters, and the like, which are well-known from the detergency art.
- detersive surfactants contain an alkyl group in the C9-C18 range; the anionic detersive surfactants can be used in the form of their sodium, potassium, ammonium or alkanaolammonium salts.
- Highly preferred HDL compositions comprising anionic detersive surfactants typically contain :
- compositions comprise, besides the mixture of succinate and citrate builders noted, from 7 % to 12 % of the anionic (especially alkyl benzene sulfonate) detersive surfactant and from 10 % to 20 % of the aforesaid ethoxylated alcohol nonionic surfactant.
- compositions with mixed anionic/nonionic surfactants are formulated at pH 7.0 - 9.0, preferably 7.3 - 8.6 Most preferably, the composition contains no more than 16 % of the citrate/succinate builder, as noted above.
- the fuild carrier for the present composition can comprise water; mixtures of water-ethanol; water-glycol mixtures, and the like, all well-known to formulators of HDL's.
- Typically and HDL will comprise 20 % to 40 % fluid carrier, said carrier comprising 80 % water, and 20 % ethanol.
- compositions herein can contain other ingredients which aid in their cleaning performance.
- laundry compositions herein also contain enzymes to enhance their through-the-wash cleaning performance on a variety of soils and stains.
- Amylase and protease enzymes suitable for use in detergents are well-known in the art and in commercially available liquid detergents.
- Commercial detersive enzymes preferably a mixture of amylase and protease are typically used at levels of 0.001 % to 2 %, and higher, in the present compositions.
- compositions herein can contain, in addition to ingredients already mentioned, various other optional ingredients typically used in commercial products to provide aesthetic or additional product performance benefits.
- Typical ingredients include pH regulants, perfumes, dyes, optical brighteners, soil suspending agents, hydrotropes and gel-control agents, freeze-thaw stabilizers, bactericides, preservatives, suds control gents, and the like.
- the compositions are typically used at a concentration of at least 500 ppm, preferably 0.10 % to 2.5 %, in an aqueous laundry bath a pH 7-11 to launder fabrics.
- the laundering can be carried out by agitating fabrics with the present compositions over the range from 5°C to the boil, with excellent results.
- a preferred HDL is as follows:
Abstract
Description
- The subject matter of this invention relates to liquid laundry detergent compositions which contain alkyl-or alkenyl-succinates, in combination with citrates, as detergency builder ingredients.
- The patent literature describes the use of alkyl- and alkenyl-succinates as surfactants: US 2.283.214; detergency boosters UK 1.293.753; in various liquid cleaners UK 1.528.171, US 4.277.378; builders US 2.462.758 and the like. See also US 3.784.486.
- UK 1.293.753 describes solid laundry detergent compositions preferably comprising 20 % to 40 % of such succinates as builders.
- A variety of substituted succinates and "sulfur-succinates" are described for various similar uses; US 3.912.663, US 4.152.515 and US 3.725.286.
- The use of various succinates in combination with certain detergency ingredients is also known; see EPO 79191 and EPO 70190, as well as German 32 05 791 and German 33 17 337.
- Indeed, the use of carboxylate materials of various types in solid and liquid cleaners is well-known; see UK 1.514.276 for amine soap mixtures; UK 1.429.143 for zeolite/polycarboxylate mixtures: US 2.264.103 for citrate and other carboxylate plus soap mixtures; US 3.634.392 for polysaccharidic carboxylate detergency builders; US 3.898.187 for various sulfur-succinates in dishwashing detergents; and UK 1.400.898 for use with clay softeners.
- It has now been discovered that the formulation of homogeneous liquid detergents containing alkyl- or alkenyl-succinates is fraught with difficulty. Formulations containing above about 17.5 % of the succinate are unstable, or can only be stabilized by decreasing the level of detersive surfactant. Too low a surfactant level, or surfactants of the wrong kind, can give problems with the formulations' greasy stain removal performance. Moreover, too much of the succinate in such formulations can result in excessive deposition of the succinate builder onto fabric surfaces.
- It is a major object and advantage of the present invention that superior overall product performance is achieved from a liquid detergent product by the proper, and heretofore unrecognized, combination of various known alkyl- and alkenyl succinate builders with citrate builders and surfactants, all properly balanced to achieve the desired cleaning function without excessive fabric build-up.
- The present invention relates to homogeneous detergent compositions designed especially for laundering fabrics. Said compositions are commonly referred to as "heavy-duty liquids" or "HDL's", since they are designed to remove even the "heaviest" soil loads from fabrics when used in a conventional laundering operation.
- The compositions herein comprise fluid carrier medium, a detersive surfactant or mixtures of detersive surfactants, and optionally, detersive enzymes and other conventional detersive ingredients, characterized in that said compositions contain:
- a) from 6 % to 12 % by weight of an anionic detersive surfactant;
- b) from 2 % to 6% by weight of a citrate detergency builder; and
- c) from 8% to 13 % by weight of an alkyl or alkenyl succinate detergency builder selected from the C₁₀-C₁₆ alkyl or alkenyl succinates.
- In a method aspect, the invention comprises a method for laundering fabrics by agitating said fabrics in a aqueous laundering liquor, said liquor containing at least 0.05 % by weight of a composition of the foregoing type.
- All percentages, ratios or proportions of ingredients disclosed herein are by weight, unless otherwise specified.
- The essential components of the present compositions are the alkyl- or alkenyl-succinate, the citrate builder, and the detersive surfactant. The optional detersive adjunct ingredients, as well as the fluid carrier medium, etc., are all well-known to workers in this field.
- Succinate Builder : The preferred builders herein are of the general formula R-CH(COOH)CH₂(COOH), i.e., derivatives of succinic acid, wherein R is C₁₀-C₁₆ alkyl or alkenyl, preferably C₁₂-C₁₆.
- These succinate builders are preferably used in the form of their water-soluble salts, including the sodium, potassium, ammonium and alkanolammonium salts (e.g., mono-, di-, or tri-ethanolammonium).
- Specific examples of succinate builders include: lauryl succinate, myristyl succinate, palmityl succinate, 2-dodecenyl succinate (preferred), 2-tetradecenyl succinate, and the like.
- Citrate Builder : The citrate builder employed in the practice of this invention includes any water-soluble salt of citric acid. Such salts include, for example, sodium, potassium, ammonium or alkanolammonium salts, as in the case of the succinate builders already described. As will be seen hereinafter, the citrate builders are unique in their ability to prevent undue fabric build-up by the succinate builders.
- In this regard, a highly preferred HDL composition herein comprises a mixture of 3.7 % citrate (specified as citric acid) and 10.4 % 2-dodecenyl succinate as the builder, and is formulated at a pH range of 7.3 to 8.6.
- Detersive Surfactants - The detergent compositions of this invention will contain organic surface-active agents ("surfactants") to provide the cleaning benefits associated with the use of such materials.
- As noted hereinabove, it is difficult to formulate a stable, homogeneous HDL which contains an effective amount of detersive surfactant. Importantly, however, it is highly desirable for the HDL's to contain at least 5 % , preferably 7 % to 12 % of an anionic surfactant to give true "heavy-duty" laundering performance on a wide spectrum of soils and stains.
- Anionic detersive surfactants useful herein include the well-known synthetic alkyl benzene sulfonates (which are highly preferred in the present HDL's) alkyl- and alkylether sulfates, paraffin sulfonates, olefin sulfonates, alpha-sulfonates of fatty acids and of fatty acid esters, and the like, which are well-known from the detergency art. In general, such detersive surfactants contain an alkyl group in the C₉-C₁₈ range; the anionic detersive surfactants can be used in the form of their sodium, potassium, ammonium or alkanaolammonium salts. Standard texts such as the McCutcheon's Index contain detailed listings of such typical detersive surfactants. While the C₁₀-C₁₄ alkyl benzene sulfonates are especially preferred herein, the C₁₂-C₁₈ paraffin-sulfonates and C₁₁-C₁₈ alkyl sulfates may also be used in HDL compositions of the present type.
- Highly preferred HDL compositions comprising anionic detersive surfactants typically contain :
- a) from 7 % to 12 % by weight of a C₁₀-C₁₄ alkyl benzene sulfonate anionic detersive surfactant;
- b) from 2 % to 6 % by weight of a citrate detergency builder; and
- c) from 8 % to 13 % by weight of an alkyl or alkenyl succinate detergency builder selected from the salts of C₁₀-C₁₆ alkyl or alkenyl succinates, especially 2-dodecenyl succinate, said composition having a pH of 7.3 to 8.6.
- In order to enhance the detergency performance of the HDL's of this invention, it is preferred that they also contain a nonionic surfactant of the ethoxylated alcohol type, especially the C₁₀-C₁₅ alcohols ethoxylated with 4 to 7 EO groups. Such compositions comprise, besides the mixture of succinate and citrate builders noted, from 7 % to 12 % of the anionic (especially alkyl benzene sulfonate) detersive surfactant and from 10 % to 20 % of the aforesaid ethoxylated alcohol nonionic surfactant. As before, such compositions with mixed anionic/nonionic surfactants are formulated at pH 7.0 - 9.0, preferably 7.3 - 8.6 Most preferably, the composition contains no more than 16 % of the citrate/succinate builder, as noted above.
- Fluid Carrier Medium - The fuild carrier for the present composition can comprise water; mixtures of water-ethanol; water-glycol mixtures, and the like, all well-known to formulators of HDL's. Typically and HDL will comprise 20 % to 40 % fluid carrier, said carrier comprising 80 % water, and 20 % ethanol.
- Detersive Adjuncts - The compositions herein can contain other ingredients which aid in their cleaning performance. For example, it is highly preferred that the laundry compositions herein also contain enzymes to enhance their through-the-wash cleaning performance on a variety of soils and stains. Amylase and protease enzymes suitable for use in detergents are well-known in the art and in commercially available liquid detergents. Commercial detersive enzymes (preferably a mixture of amylase and protease) are typically used at levels of 0.001 % to 2 %, and higher, in the present compositions.
- Moreover, the compositions herein can contain, in addition to ingredients already mentioned, various other optional ingredients typically used in commercial products to provide aesthetic or additional product performance benefits. Typical ingredients include pH regulants, perfumes, dyes, optical brighteners, soil suspending agents, hydrotropes and gel-control agents, freeze-thaw stabilizers, bactericides, preservatives, suds control gents, and the like.
- In a through-the-wash laundry mode, the compositions are typically used at a concentration of at least 500 ppm, preferably 0.10 % to 2.5 %, in an aqueous laundry bath a pH 7-11 to launder fabrics. The laundering can be carried out by agitating fabrics with the present compositions over the range from 5°C to the boil, with excellent results.
- The following example is typical of the preferred compositions of this invention, but is not intended to limit the scope of the invention.
-
Claims (11)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT86201319T ATE68523T1 (en) | 1985-08-15 | 1986-07-25 | STRENGTHENED LIQUID DETERGENT. |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB08520489A GB2179669B (en) | 1985-08-15 | 1985-08-15 | Built liquid detergents |
GB8520489 | 1985-08-15 |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0212723A2 true EP0212723A2 (en) | 1987-03-04 |
EP0212723A3 EP0212723A3 (en) | 1988-08-31 |
EP0212723B1 EP0212723B1 (en) | 1991-10-16 |
Family
ID=10583826
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP86201319A Expired - Lifetime EP0212723B1 (en) | 1985-08-15 | 1986-07-25 | Built liquid detergents |
Country Status (9)
Country | Link |
---|---|
EP (1) | EP0212723B1 (en) |
JP (1) | JPS62109899A (en) |
KR (1) | KR870002240A (en) |
AT (1) | ATE68523T1 (en) |
AU (1) | AU6117986A (en) |
DE (1) | DE3681999D1 (en) |
GB (1) | GB2179669B (en) |
GR (1) | GR862134B (en) |
IE (1) | IE59407B1 (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0476212A1 (en) * | 1990-09-17 | 1992-03-25 | The Procter & Gamble Company | Liquid detergent compositions |
US5916865A (en) * | 1996-08-30 | 1999-06-29 | Clariant Gmbh | Liquid bleaching agent suspension |
US6352966B1 (en) | 2000-05-19 | 2002-03-05 | Albemarle Corporation | Cleansing bars |
WO2003022968A1 (en) * | 2001-09-13 | 2003-03-20 | Johnsondiversey, Inc. | Low foam producing cleaning-in-place composition |
US6953507B2 (en) | 2003-03-21 | 2005-10-11 | Ecolab Inc. | Low temperature cleaning |
WO2007141527A1 (en) | 2006-06-07 | 2007-12-13 | Reckitt Benckiser N. V. | Detergent composition |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ATE69260T1 (en) * | 1986-03-31 | 1991-11-15 | Procter & Gamble | LIQUID DETERGENTS CONTAINING AN ANIONIC SURFACE ACTIVE AGENT, A Succinic Acid Builder SALT AND A FATTY ACID. |
JP2559448B2 (en) * | 1988-02-26 | 1996-12-04 | 花王株式会社 | Liquid detergent composition |
US4965013A (en) * | 1989-05-01 | 1990-10-23 | Miles Inc. | Method of high temperature laundering using sodium citrate and an anionic |
JP3606390B2 (en) * | 1994-12-21 | 2005-01-05 | 株式会社小松製作所 | Mold protector for hydraulic press |
JP4864598B2 (en) * | 2006-08-11 | 2012-02-01 | 花王株式会社 | Cleaning composition for hard surface |
EP2713692B1 (en) * | 2011-05-27 | 2016-08-10 | CNH Industrial Belgium nv | Low profile sickle drive |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2149500A1 (en) * | 1971-08-17 | 1973-03-30 | Unilever Nv | |
US3898187A (en) * | 1972-12-26 | 1975-08-05 | Procter & Gamble | Liquid detergent compositions |
GB1528171A (en) * | 1975-01-06 | 1978-10-11 | Diamond Shamrock Europ | Foaming hard surface cleaner formulations |
US4152515A (en) * | 1973-04-06 | 1979-05-01 | Lever Brothers Company | Builders for detergent compositions |
GB2047264A (en) * | 1979-03-23 | 1980-11-26 | Mira Lanza Spa | Detergent compositions having a low phosphorus content |
GB2049723A (en) * | 1979-04-20 | 1980-12-31 | Kao Corp | Detergent composition |
-
1985
- 1985-08-15 GB GB08520489A patent/GB2179669B/en not_active Expired
-
1986
- 1986-07-25 DE DE8686201319T patent/DE3681999D1/en not_active Expired - Fee Related
- 1986-07-25 AT AT86201319T patent/ATE68523T1/en not_active IP Right Cessation
- 1986-07-25 EP EP86201319A patent/EP0212723B1/en not_active Expired - Lifetime
- 1986-08-13 GR GR862134A patent/GR862134B/en unknown
- 1986-08-14 AU AU61179/86A patent/AU6117986A/en not_active Abandoned
- 1986-08-14 KR KR1019860006706A patent/KR870002240A/en not_active Application Discontinuation
- 1986-08-14 IE IE218986A patent/IE59407B1/en not_active IP Right Cessation
- 1986-08-14 JP JP61191169A patent/JPS62109899A/en active Pending
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2149500A1 (en) * | 1971-08-17 | 1973-03-30 | Unilever Nv | |
US3898187A (en) * | 1972-12-26 | 1975-08-05 | Procter & Gamble | Liquid detergent compositions |
US4152515A (en) * | 1973-04-06 | 1979-05-01 | Lever Brothers Company | Builders for detergent compositions |
GB1528171A (en) * | 1975-01-06 | 1978-10-11 | Diamond Shamrock Europ | Foaming hard surface cleaner formulations |
GB2047264A (en) * | 1979-03-23 | 1980-11-26 | Mira Lanza Spa | Detergent compositions having a low phosphorus content |
GB2049723A (en) * | 1979-04-20 | 1980-12-31 | Kao Corp | Detergent composition |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0476212A1 (en) * | 1990-09-17 | 1992-03-25 | The Procter & Gamble Company | Liquid detergent compositions |
WO1992005238A1 (en) * | 1990-09-17 | 1992-04-02 | The Procter & Gamble Company | Liquid detergent compositions |
US5229028A (en) * | 1990-09-17 | 1993-07-20 | The Procter & Gamble Company | Liquid detergent compositions |
TR26008A (en) * | 1990-09-17 | 1993-11-01 | Procter & Gamble | EFFECTIVE IMPACT ON LIQUID DETERGENT COMPOUNDS CI NEW SYSTEM |
US5916865A (en) * | 1996-08-30 | 1999-06-29 | Clariant Gmbh | Liquid bleaching agent suspension |
US6352966B1 (en) | 2000-05-19 | 2002-03-05 | Albemarle Corporation | Cleansing bars |
WO2003022968A1 (en) * | 2001-09-13 | 2003-03-20 | Johnsondiversey, Inc. | Low foam producing cleaning-in-place composition |
US6953507B2 (en) | 2003-03-21 | 2005-10-11 | Ecolab Inc. | Low temperature cleaning |
WO2007141527A1 (en) | 2006-06-07 | 2007-12-13 | Reckitt Benckiser N. V. | Detergent composition |
Also Published As
Publication number | Publication date |
---|---|
IE862189L (en) | 1987-02-15 |
GR862134B (en) | 1986-11-06 |
DE3681999D1 (en) | 1991-11-21 |
IE59407B1 (en) | 1994-02-23 |
GB2179669B (en) | 1988-12-29 |
EP0212723A3 (en) | 1988-08-31 |
JPS62109899A (en) | 1987-05-21 |
GB2179669A (en) | 1987-03-11 |
ATE68523T1 (en) | 1991-11-15 |
GB8520489D0 (en) | 1985-09-18 |
EP0212723B1 (en) | 1991-10-16 |
KR870002240A (en) | 1987-03-30 |
AU6117986A (en) | 1987-02-19 |
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