EP0383373A2 - A detergent composition in liquid form for the pretreatment of textiles - Google Patents
A detergent composition in liquid form for the pretreatment of textiles Download PDFInfo
- Publication number
- EP0383373A2 EP0383373A2 EP90200237A EP90200237A EP0383373A2 EP 0383373 A2 EP0383373 A2 EP 0383373A2 EP 90200237 A EP90200237 A EP 90200237A EP 90200237 A EP90200237 A EP 90200237A EP 0383373 A2 EP0383373 A2 EP 0383373A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- detergent composition
- composition according
- glycol
- enzymes
- water
- 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.)
- Ceased
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
- C11D3/28—Heterocyclic compounds containing nitrogen in the ring
-
- 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
- C11D3/26—Organic compounds containing nitrogen
- C11D3/30—Amines; Substituted amines ; Quaternized amines
-
- 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
- C11D3/38—Products with no well-defined composition, e.g. natural products
- C11D3/386—Preparations containing enzymes, e.g. protease or amylase
- C11D3/38663—Stabilised liquid enzyme compositions
Definitions
- the present invention relates to a detergent composition for the pretreatment of textiles, in particular to a liquid stain remover, which is especially suitable for local pretreatment of stains before washing the laundry in the conventional manner.
- a liquid stain remover which is especially suitable for local pretreatment of stains before washing the laundry in the conventional manner.
- the stains are increasingly given a pretreatment with a liquid stain remover, a so-called pre-spotter. As a result of this pretreatment the stains are better removed in the conventional washing treatment.
- nonionic surfactant e.g., ethoxylated nonyl phenyl
- sodium citrate sodium citrate
- products based on alkanes and isopropyl alcohol to which water and ethoxylated fatty alcohol are added.
- the object of the invention is to provide a universal detergent composition in liquid form for the pretreatment of textiles, which is suitable for substantially all types of stains, and which has a clearly improved activity over the known pretreatment compositions.
- This invention therefore comprises a detergent composition in liquid form for the preatreatment of textiles, comprising, calculated on the total detergent composition:
- the composition according to this invention has an excellent cleansing activity against all types of different stains.
- the composition should contain the prescribed amount of water in combination with enzyme, surfactant, and isopropanol-amine. The use of this combination results in an adequate removal of stains, for which the cohesion parameter of isopropanolamine in the system, combined with the other active components, is likely to be responsible.
- the cohesion parameter is a measure of a substance property which meets with increased use (see, e.g., A.F.M. Barton "Handbook of solubility parameters and other cohesion parameters", 1983, CRC Press, Inc. ISBN 0-8493-3295-8).
- the cohesion of a substance is connected with the intermolecular forces, such as dispersion forces, dipole interaction, induced dipole interaction, hydrogen bonds etc., in brief the van der Waals forces which effect the cohesion of a substance.
- the cohesion parameter is calculated as the root of the quotient of the energy content per mole and the molar volume. Substances having the same cohesion parameter excellently dissolve in each other.
- the value of the cohesion parameter can be determined by way of experiment, but can also be calculated from the atom group composition of the molecule (see Barton's above-cited Handbook, chapter 6).
- the detergent composition according to this invention may consist of the above-mentioned components, but a polyglycol and/or a polyglycol ether are preferably also incorporated in the detergent composition, because this will lead to further improved results.
- glycol and/or glycol ether employed are preferably dipropylene glycol and/or hexylene glycol and/or ethylene glycol, more in particular a mixture of these two compounds in a weight ratio of 0.5 to 2.
- stain remover components promoting the removal of a specific type of stains.
- oleic acid may be added, and more in particular, metal salts can be bound by using nitrilotriacetic acid.
- the total stain removing activity can be intensified by using, e.g., urea in the solution.
- the stain remover has a pH value ranging from 5 to 12, and more in particular from 6 to 9. At such a pH the activity is most satisfactory.
- This pH can be obtained by first dissolving all the components and then adapting the pH by addition of organic acid.
- organic acids are citric acid, formic acid and benzoic acid.
- the surfactant may be an anionic or a nonionic surfactant. Since according to the invention the content of metal ions in the detergent composition is preferably limited as much as possible in order to obtain a better cleansing effect and a stable product, the use of a nonionic surfactant, such as an alkanol ethoxylate, e.g., fat alcohol ethoxylate, is preferred. Preferably, use is made of a nonionic surfactant based on an ethylene oxide adduct having an average of preferably 7-9 ethoxylene oxide units per molecule. The amount of surfactant ranges from 0.01 to 5 wt.%, and 0.1-2 wt.% based on the total detergent composition gives the most satisfactory results. It is also possible to use an anionic surfactant. In view of the requirement of introducing as few metal ions as possible into the system, the cation preferably employed is a nitrogen base. Suitable nitrogen bases are amines, such as ethanolamine.
- the content of metal ions in the detergent composition preferably does not exceed 0.1 wt.%. At higher contents problems occur with the stain removing activity of the detergent composition.
- a sequestering agent may be incorporated in the detergent composition, such as nitrilotriacetic acid, in order to bind calcium and magnesium ions with the wash water.
- the amounts of sequestering agent may vary within wide limits. Suitable limits range from 0.1 to 4 wt.%.
- Enzyme concentrates are used in conventional amounts of from 0.001 to 2.0 wt.% based on the total weight.
- Suitable enzymes are selected from the group consisting of proteolytic enzymes, lipolytic enzymes, cellulytic enzymes, and amylytic enzymes. In general, proteolytic enzymes or proteases are preferred. It is also possible, however, to use a combination of lipolytic enzymes, cellulytic enzymes, and amylytic enzymes. These enzymes may be used in pure form, or as enzyme preparation.
- the detergent composition according to this invention may also contain other additives which may be present in amounts of maximally 5 wt.%. Special examples thereof are perfumes, colorants, bleaching agents, and thickening agents.
- the detergent composition according to this invention can be simply composed by dissolving the different components to be used. It is possible to bring the stain remover into paste form by adding gelling or paste-forming components in such an amount as to obtain a processable paste. This can be appropriately spread on the stain.
- compositions were compared with each other for activity with respect to stain removal.
- Basic composition Hexylene glycol 10.0% Ethylene glycol 10.0% Enzyme concentrate (protease) 0.5% Benzoic acid 0.1% Formic acid up to about 2.5% Aminoalkanol 4.0% Water up to 100 %.
- PK SUNAK EMPA 101 KREFELD EMPA 116 EMPA 111 AVERAGE only washing 0 0 0 0 0 0 0 0 0.0 basis with morpholine 12 2 -1 -2 -2 10 1 4 2.9 basis with monoethanolamine 13 0 5 -1 -1 12 1 5 4.3 basis with 1-aminopropanol-2 15 4 3 -1 -1 9 2 6 4.6 basis with 3-aminopropanol 12 1 2 0 -1 13 1 8 4.4 basis with diethanolamine 13 4 2 -2 -1 9 1 6 3.8 basis with triethanolamine 9 4 3 -4 -1 14 1 8 4.4 basis with 3-aminopropanediol 13 12 7 -1 0 12 1 -9 4.6
- Example 2 and comparative example.
Abstract
- a. at least 60 wt.% water,
- b. 0.001 to 2.0 wt.% enzyme,
- c. 0.01 to 5 wt.% nonionic and/or anionic surfactant,
- d. 0.1 to 5 wt.% propanolamine,
- e. at least one organic acid in an amount up to a pH ranging from 5 to 12,
- f. 0 to 30 wt.% liquid and/or water-soluble glycol, and, if desired,
- g. other additives in an amount of not more than 5 wt.%.
Description
- The present invention relates to a detergent composition for the pretreatment of textiles, in particular to a liquid stain remover, which is especially suitable for local pretreatment of stains before washing the laundry in the conventional manner. For the purpose of removing persistent stains on laundry the stains are increasingly given a pretreatment with a liquid stain remover, a so-called pre-spotter. As a result of this pretreatment the stains are better removed in the conventional washing treatment.
- These products are often based on a combination of a nonionic surfactant, e.g., ethoxylated nonyl phenyl, with sodium citrate and water. Also known are products based on alkanes and isopropyl alcohol to which water and ethoxylated fatty alcohol are added.
- A variety of such detergent compositions are known from the literature and the market. For instance, French patent publication 2,448,568 discloses a stain remover for removing greasy stains which consists of a large amount of nonionic surfactant, an organic solvent, water, an enzyme, and an alkanolamine. Such pretreatment compositions are specific, i.e. they are suitable for one type of stains only.
- The object of the invention is to provide a universal detergent composition in liquid form for the pretreatment of textiles, which is suitable for substantially all types of stains, and which has a clearly improved activity over the known pretreatment compositions.
- This invention therefore comprises a detergent composition in liquid form for the preatreatment of textiles, comprising, calculated on the total detergent composition:
- a. at least 60 wt.% water,
- b. 0.001 to 2.0 wt.% enzyme,
- c. 0.01 to 5 wt.% nonionic and/or anionic surfactant,
- d. 0.1 to 5 wt.% propanolamine, preferably isopropanolamine,
- e. at least one organic acid in an amount up to a pH ranging from 5 to 12,
- f. 0 to 30 wt.% liquid and/or water-soluble glycol, and, if desired,
- g. other additives in an amount of not more than 5 wt.%.
- Surprisingly, it has been found that the composition according to this invention has an excellent cleansing activity against all types of different stains. In this connection it is highly important that the composition should contain the prescribed amount of water in combination with enzyme, surfactant, and isopropanol-amine. The use of this combination results in an adequate removal of stains, for which the cohesion parameter of isopropanolamine in the system, combined with the other active components, is likely to be responsible.
- The cohesion parameter is a measure of a substance property which meets with increased use (see, e.g., A.F.M. Barton "Handbook of solubility parameters and other cohesion parameters", 1983, CRC Press, Inc. ISBN 0-8493-3295-8). The cohesion of a substance is connected with the intermolecular forces, such as dispersion forces, dipole interaction, induced dipole interaction, hydrogen bonds etc., in brief the van der Waals forces which effect the cohesion of a substance. The cohesion parameter is calculated as the root of the quotient of the energy content per mole and the molar volume. Substances having the same cohesion parameter excellently dissolve in each other.
- The value of the cohesion parameter can be determined by way of experiment, but can also be calculated from the atom group composition of the molecule (see Barton's above-cited Handbook, chapter 6).
- Important advantages of the detergent composition according to this invention are its simple composition, the fact that the detergent composition contains few if any components that may induce irritation of the skin, and also the absence of components in ecologically unsound amounts. The detergent composition is in principle also odourless, which in particular with agents for removing greasy stains is certainly not the case.
- The detergent composition according to this invention may consist of the above-mentioned components, but a polyglycol and/or a polyglycol ether are preferably also incorporated in the detergent composition, because this will lead to further improved results.
- The glycol and/or glycol ether employed are preferably dipropylene glycol and/or hexylene glycol and/or ethylene glycol, more in particular a mixture of these two compounds in a weight ratio of 0.5 to 2.
- It is also possible to incorporate in the stain remover components promoting the removal of a specific type of stains. For the removal of greasy stains oleic acid may be added, and more in particular, metal salts can be bound by using nitrilotriacetic acid. Finally, the total stain removing activity can be intensified by using, e.g., urea in the solution.
- In order to obtain a suitable activity, it is ensured that the stain remover has a pH value ranging from 5 to 12, and more in particular from 6 to 9. At such a pH the activity is most satisfactory.
- This pH can be obtained by first dissolving all the components and then adapting the pH by addition of organic acid. Suitable organic acids are citric acid, formic acid and benzoic acid.
- The surfactant may be an anionic or a nonionic surfactant. Since according to the invention the content of metal ions in the detergent composition is preferably limited as much as possible in order to obtain a better cleansing effect and a stable product, the use of a nonionic surfactant, such as an alkanol ethoxylate, e.g., fat alcohol ethoxylate, is preferred. Preferably, use is made of a nonionic surfactant based on an ethylene oxide adduct having an average of preferably 7-9 ethoxylene oxide units per molecule. The amount of surfactant ranges from 0.01 to 5 wt.%, and 0.1-2 wt.% based on the total detergent composition gives the most satisfactory results. It is also possible to use an anionic surfactant. In view of the requirement of introducing as few metal ions as possible into the system, the cation preferably employed is a nitrogen base. Suitable nitrogen bases are amines, such as ethanolamine.
- The content of metal ions in the detergent composition preferably does not exceed 0.1 wt.%. At higher contents problems occur with the stain removing activity of the detergent composition.
- In addition to the above-mentioned main components, a sequestering agent may be incorporated in the detergent composition, such as nitrilotriacetic acid, in order to bind calcium and magnesium ions with the wash water. The amounts of sequestering agent may vary within wide limits. Suitable limits range from 0.1 to 4 wt.%.
- Enzyme concentrates are used in conventional amounts of from 0.001 to 2.0 wt.% based on the total weight.
- Suitable enzymes are selected from the group consisting of proteolytic enzymes, lipolytic enzymes, cellulytic enzymes, and amylytic enzymes. In general, proteolytic enzymes or proteases are preferred. It is also possible, however, to use a combination of lipolytic enzymes, cellulytic enzymes, and amylytic enzymes. These enzymes may be used in pure form, or as enzyme preparation.
- The detergent composition according to this invention may also contain other additives which may be present in amounts of maximally 5 wt.%. Special examples thereof are perfumes, colorants, bleaching agents, and thickening agents.
- The detergent composition according to this invention can be simply composed by dissolving the different components to be used. It is possible to bring the stain remover into paste form by adding gelling or paste-forming components in such an amount as to obtain a processable paste. This can be appropriately spread on the stain.
- The invention will now be explained with reference to a few examples, which are for the purpose of elucidation only.
- A plurality of compositions were compared with each other for activity with respect to stain removal.
Basic composition: Hexylene glycol 10.0% Ethylene glycol 10.0% Enzyme concentrate (protease) 0.5% Benzoic acid 0.1% Formic acid up to about 2.5% Aminoalkanol 4.0% Water up to 100 %.
Soaking time: 5 min.
Washing time: 30 min.
Washing temperature: 30°C. - These products were tested on a plurality of test cloths.
- After the reflection had been measured on different cloths, samples thereof were soaked in the different products for 15 minutes, and after washing with a conventional main wash detergent composition in the linitester, the reflection was determined again.
PRE-SPOTTER VEKOPROP EMPA 112 KW YOVE PK. SUNAK EMPA 101 EMPA 116 KREFELD EMPA 111 AVERAGE pH a. Only washing -3 4 8 20 2 8 3 39 9.9 b. basis with morpholine 8 6 6 18 1 18 4 42 12.8 6.1 c. basis with monoethanolamine 9 4 13 20 1 20 4 44 14.3 5.9 I. basis with 1-aminopropanol-2 11 8 10 19 1 17 5 45 14.5 5.9 d. basis with 3-aminopropanol 8 5 9 20 2 20 4 46 14.3 6.0 e. basis with diethanolamine 9 7 10 18 1 17 4 45 13.8 6.0 f. basis with triethanolamine 6 8 11 16 1 22 4 46 14.3 6.1 g. basis with 3-aminopropanediol 10 16 15 19 2 20 4 30 14.5 7.0 Standard soiled cloth supplier type of soil 1. Vekoprop TNO Nederland fat, carbohydrate, egg white ,pigment 2. Kwijove-polyester-cotton id. quartz, iron oxide, oil, fat 3. Sunak id. sugar, wine 4. Empa 101 (ink/oil) Empa Switzerland ink, oil, egg white 5. Empa 111 (blood) id. blood 6. Empa 112 (cocoa) id. cocoa, egg white, fat 7. Empa 116 (standard) id. blood, milk, ink 8. Krefeld DWF, Krefeld, FRG kaolin, soot, iron oxide Literature: Detergency "Theory and Test methods" Part II, (Ed. W.G. Cutler and R.C. Davies), New York, 1975, page 539 PRE-SPOTTER VEKOPROP EMPA 112 KW. PK SUNAK EMPA 101 KREFELD EMPA 116 EMPA 111 AVERAGE only washing 0 0 0 0 0 0 0 0 0.0 basis with morpholine 12 2 -1 -2 -2 10 1 4 2.9 basis with monoethanolamine 13 0 5 -1 -1 12 1 5 4.3 basis with 1-aminopropanol-2 15 4 3 -1 -1 9 2 6 4.6 basis with 3-aminopropanol 12 1 2 0 -1 13 1 8 4.4 basis with diethanolamine 13 4 2 -2 -1 9 1 6 3.8 basis with triethanolamine 9 4 3 -4 -1 14 1 8 4.4 basis with 3-aminopropanediol 13 12 7 -1 0 12 1 -9 4.6 - All these examples clearly show that the formulation with isopropanol is superior.
- Three formulations were tested in a test starting from laundry from a number of households. The laundry was first sorted according to the number and nature of the stains, so that comparable stain numbers were present in each laundry charge. The stains were pretreated with a detergent composition in equal amounts. Then the laundry was washed with a mediocre detergent composition so as to show the differences more clearly. The results are listed in the table, together with the composition of the employed detergent compositions.
Table 1 Composition (wt.%) A B C isopropanolamine 2.5 - - morpholine - 2.5 - nonionic surfactant 2.0x 2.0x 8xx sodium citrate - - 2 enzyme 0.5 0.5 - ethylene glycol 10 10 - dipropylene glycol 10 10 - citric acid up to pH = 8 up to pH = 9 - thickening agent 1.0 1.0 - water up to 100% up to 100% up to 100% x 1 part of Synperonic A7, 1 part of amine oxide xx nonyl phenol-7 EO. Table 2 Composition A B C -x Stain removal with kitchen-cloths 17.7 11.8 10.4 8.7 x no treatment
Claims (15)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NL8900267 | 1989-02-03 | ||
NL8900267A NL8900267A (en) | 1989-02-03 | 1989-02-03 | LIQUID CLEANER. |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0383373A2 true EP0383373A2 (en) | 1990-08-22 |
EP0383373A3 EP0383373A3 (en) | 1990-08-29 |
Family
ID=19854068
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP90200237A Ceased EP0383373A3 (en) | 1989-02-03 | 1990-02-02 | A detergent composition in liquid form for the pretreatment of textiles |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP0383373A3 (en) |
JP (1) | JPH02289698A (en) |
AU (1) | AU622520B2 (en) |
NL (1) | NL8900267A (en) |
NO (1) | NO900497L (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1991013142A1 (en) * | 1990-03-01 | 1991-09-05 | Novo Nordisk A/S | Lipase containing liquid pre-spotter and use of such pre-spotter |
US5447649A (en) * | 1990-03-01 | 1995-09-05 | Novo Nordisk A/S | Lipase containing liquid pre-spotter and use of such pre-spotter |
EP0957155A2 (en) * | 1998-05-15 | 1999-11-17 | Ecolab Inc. | Removal of blood stains |
WO2007113241A1 (en) * | 2006-03-31 | 2007-10-11 | Novozymes A/S | A stabilized liquid enzyme composition |
US8071345B2 (en) | 2006-03-31 | 2011-12-06 | Novozymes A/S | Stabilized subtilisin composition |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
USB458819I5 (en) * | 1971-12-23 | 1976-04-13 | ||
FR2448568A1 (en) * | 1979-02-07 | 1980-09-05 | Unilever Nv | PRELIMINARY TREATMENT CLEANING COMPOSITION FOR LAUNDRY |
US4243546A (en) * | 1979-03-23 | 1981-01-06 | The Drackett Company | Stable aqueous compositions containing enzymes |
EP0151678A1 (en) * | 1983-08-12 | 1985-08-21 | THE PROCTER & GAMBLE COMPANY | Stable liquid detergent compositions |
-
1989
- 1989-02-03 NL NL8900267A patent/NL8900267A/en not_active Application Discontinuation
-
1990
- 1990-02-02 AU AU49038/90A patent/AU622520B2/en not_active Ceased
- 1990-02-02 NO NO90900497A patent/NO900497L/en unknown
- 1990-02-02 EP EP90200237A patent/EP0383373A3/en not_active Ceased
- 1990-02-03 JP JP2365090A patent/JPH02289698A/en active Pending
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
USB458819I5 (en) * | 1971-12-23 | 1976-04-13 | ||
FR2448568A1 (en) * | 1979-02-07 | 1980-09-05 | Unilever Nv | PRELIMINARY TREATMENT CLEANING COMPOSITION FOR LAUNDRY |
US4243546A (en) * | 1979-03-23 | 1981-01-06 | The Drackett Company | Stable aqueous compositions containing enzymes |
EP0151678A1 (en) * | 1983-08-12 | 1985-08-21 | THE PROCTER & GAMBLE COMPANY | Stable liquid detergent compositions |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1991013142A1 (en) * | 1990-03-01 | 1991-09-05 | Novo Nordisk A/S | Lipase containing liquid pre-spotter and use of such pre-spotter |
WO1991013141A1 (en) * | 1990-03-01 | 1991-09-05 | Novo Nordisk A/S | Lipase containing liquid pre-spotter and use of such pre-spotter |
US5447649A (en) * | 1990-03-01 | 1995-09-05 | Novo Nordisk A/S | Lipase containing liquid pre-spotter and use of such pre-spotter |
EP0957155A2 (en) * | 1998-05-15 | 1999-11-17 | Ecolab Inc. | Removal of blood stains |
EP0957155A3 (en) * | 1998-05-15 | 2000-01-05 | Ecolab Inc. | Removal of blood stains |
US6468954B2 (en) | 1998-05-15 | 2002-10-22 | Ecolab Inc. | Blood, coffee or fruit juice stain remover in an alkaline composition |
US6471728B2 (en) * | 1998-05-15 | 2002-10-29 | Ecolab Incorporated | Removal of blood stains |
WO2007113241A1 (en) * | 2006-03-31 | 2007-10-11 | Novozymes A/S | A stabilized liquid enzyme composition |
US8071345B2 (en) | 2006-03-31 | 2011-12-06 | Novozymes A/S | Stabilized subtilisin composition |
Also Published As
Publication number | Publication date |
---|---|
AU4903890A (en) | 1990-08-09 |
EP0383373A3 (en) | 1990-08-29 |
NO900497D0 (en) | 1990-02-02 |
NL8900267A (en) | 1990-09-03 |
AU622520B2 (en) | 1992-04-09 |
JPH02289698A (en) | 1990-11-29 |
NO900497L (en) | 1990-08-06 |
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