EP0335584A2 - Bleaching composition - Google Patents
Bleaching composition Download PDFInfo
- Publication number
- EP0335584A2 EP0335584A2 EP19890302882 EP89302882A EP0335584A2 EP 0335584 A2 EP0335584 A2 EP 0335584A2 EP 19890302882 EP19890302882 EP 19890302882 EP 89302882 A EP89302882 A EP 89302882A EP 0335584 A2 EP0335584 A2 EP 0335584A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- composition
- foam
- bleaching
- agent
- foaming
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 66
- 238000004061 bleaching Methods 0.000 title claims abstract description 20
- 238000005187 foaming Methods 0.000 claims abstract description 25
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 23
- 239000000271 synthetic detergent Substances 0.000 claims abstract description 15
- WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 9
- 239000007844 bleaching agent Substances 0.000 claims description 15
- 238000012856 packing Methods 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 150000001340 alkali metals Chemical group 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 3
- 125000005270 trialkylamine group Chemical group 0.000 claims description 3
- 238000003860 storage Methods 0.000 abstract description 9
- 239000006260 foam Substances 0.000 abstract description 7
- 230000000881 depressing effect Effects 0.000 abstract 1
- -1 alkali metal hypochlorite Chemical class 0.000 description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000005708 Sodium hypochlorite Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 239000003599 detergent Substances 0.000 description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
- SYELZBGXAIXKHU-UHFFFAOYSA-N dodecyldimethylamine N-oxide Chemical group CCCCCCCCCCCC[N+](C)(C)[O-] SYELZBGXAIXKHU-UHFFFAOYSA-N 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- 239000004150 EU approved colour Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000249 desinfective effect Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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
- C11D3/37—Polymers
- C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/373—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicones
-
- 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
- C11D3/0026—Low foaming or foam regulating compositions
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/395—Bleaching agents
- C11D3/3956—Liquid compositions
Definitions
- the present invention relates to an aqueous bleaching composition suitable for laundry and general domestic bleaching and disinfecting purposes. More particularly, it relates to an aqueous bleaching composition which also contains a synthetic detergent which is soluble in the composition thereby to impart a foaming capacity to the composition.
- the preferred bleaching agent is alkali metal hypochlorite.
- Such an aqueous alkali metal hypochlorite composition comprising a foam-imparting synthetic detergent is known in the art, e.g. from British Patent Specification 886,084. This specification describes inter alia the use of betaine-type quaternary ammonium detergent surfactants in aqueous alkali metal hypochlorite compositions.
- foam-imparting synthetic detergents are the trialkylamine oxides, containing one C12-C18 alkyl group and two C1-C3 alkyl groups.
- compositions while having the required foaming characteristics, present a problem, however, in that, during manufacture and packing of the composition the foaming of the composition makes it difficult to fill the containers properly; the composition foams out of the bottle, resulting in messy bottles which are not filled with the proper filling weight.
- the invention provides a process for the production of an aqueous bleaching composition
- an aqueous bleaching composition comprising an aqueous mixture of a bleaching agent and a foaming synthetic detergent, characterised by including a foam-depressing agent which is not stable in the mixture, packing the composition in containers while the foam-depressing agent remains effective, and optionally then storing the containers.
- the invention provides a bleaching composition obtainable by including a foam-depressing agent in an aqueous mixture of a bleaching agent and a foaming synthetic detergent, which foam-depressing agent is not stable therein, packing the composition in containers while the said foam-depressing agent remains effective, and optionally then storing the containers.
- composition in the containers will change during storage. Initially it will be temporarily low-foaming or non-foaming, with a latent foaming property. As time passes the foam-depressing agent is replaced by products of its decomposition and the foaming property will appear.
- this invention provides an aqueous bleaching composition
- a bleaching agent a foaming synthetic detergent and an additional component which is
- the invention extends of course to containers of the bleaching composition.
- a preferred feature made possible by this invention is that the containers are filled substantially full with the composition.
- the foam-depressing agent must be unstable in the composition.
- Foam-depressing agents which have been found very effective are silicones (more correctly polysiloxanes). These may be used in an amount which is at least 0.001% by weight of the composition. Amounts greater than 0.01% by weight will normally not be necessary, although amounts somewhat in excess of this may be used if desired, for instance up to 0.5% by weight of the composition.
- Polysiloxanes which can be employed as antifoam agents have the structure wherein R and R′, which may be the same or different, are alkyl or aryl groups having from 1 to 6 carbon atoms; and x is an integer of at least 20.
- the preferred polysiloxanes are polydimethylsiloxanes where both R and R′ are methyl groups. Usually the molecular weight is from 500 to 200 000.
- the composition will generally contain from 1 to 15% by weight of the bleaching agent.
- the preferred bleaching agent is alkali metal hypochlorite, for example sodium hypochlorite.
- Other bleaching agents may be used, for example hydrogen peroxide.
- the time taken for the composition to regain its foaming properties will of course depend on the rate of reaction between the bleaching agent and the silicone. Thus, hydrogen peroxide would take somewhat longer than a like amount of hypochlorite to degrade the silicone but this merely necessitates some increase in the time for which the composition is stored after packing.
- the synthetic detergents preferably used in this invention are amine oxides, more preferably trialkyl amine oxides in which one alkyl group has from 8 to 20 carbon atoms while the other two have from 1 to 4 carbon atoms.
- An example is lauryl dimethyl amine oxide.
- the amount of surfactant included in the composition typically lies in the range from 0.05 to 1.5% by weight of the composition. Amounts somewhat greater than 1.5% by weight may be used if desired, for instance up to 5% by weight.
- composition usually contains free alkali to provide a required alkaline pH.
- Other additives can be included, such as perfumes and colouring agents.
- compositions were assessed by shaking a quantity of each composition in accordance with a standardised procedure and then observing the height of foam generated.
- the compositions were analysed for residual bleaching agent after a period of storage. These test results are included in the Table below.
Landscapes
- 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
A foam-depressing agent, preferably silicone, is introduced into a bleaching composition, preferably hypochlorite, containing foaming synthetic detergent, prior to filling containers with the composition. The foam depressing agent then decomposes during storage, thus giving containers of a foaming composition while avoiding difficulties of foaming during filling of the containers.
Description
- The present invention relates to an aqueous bleaching composition suitable for laundry and general domestic bleaching and disinfecting purposes. More particularly, it relates to an aqueous bleaching composition which also contains a synthetic detergent which is soluble in the composition thereby to impart a foaming capacity to the composition. The preferred bleaching agent is alkali metal hypochlorite.
- Such an aqueous alkali metal hypochlorite composition comprising a foam-imparting synthetic detergent is known in the art, e.g. from British Patent Specification 886,084. This specification describes inter alia the use of betaine-type quaternary ammonium detergent surfactants in aqueous alkali metal hypochlorite compositions. Another suitable type of foam-imparting synthetic detergents are the trialkylamine oxides, containing one C₁₂-C₁₈ alkyl group and two C₁-C₃ alkyl groups.
- Such compositions, while having the required foaming characteristics, present a problem, however, in that, during manufacture and packing of the composition the foaming of the composition makes it difficult to fill the containers properly; the composition foams out of the bottle, resulting in messy bottles which are not filled with the proper filling weight.
- We have now found that this problem can be overcome by adding a suitable foam-depressing agent to the composition. We have found that if a foam-depressing agent is added which is not stable in the aqueous bleaching composition, the foam produced during manufacture and packing of the composition is significantly reduced. It may be reduced to an almost negligible level. However, the foaming capacity of the composition is restored upon storage of the packed composition owing to the instability of the foam-depressing agent in the composition, thus resulting in a foaming composition after storage thereof.
- The features of this invention can be stated in several ways. In a first aspect the invention provides an aqueous bleaching composition alkali metal hypochlorite composition comprising a foaming synthetic detergent with a controlled foaming behaviour, characterised in that it has been obtained by the addition thereto of a foam-depressing agent which is not stable in the composition.
- In a second aspect the invention provides a process for the production of an aqueous bleaching composition comprising an aqueous mixture of a bleaching agent and a foaming synthetic detergent, characterised by including a foam-depressing agent which is not stable in the mixture, packing the composition in containers while the foam-depressing agent remains effective, and optionally then storing the containers.
- In another aspect the invention provides a bleaching composition obtainable by including a foam-depressing agent in an aqueous mixture of a bleaching agent and a foaming synthetic detergent, which foam-depressing agent is not stable therein, packing the composition in containers while the said foam-depressing agent remains effective, and optionally then storing the containers.
- The composition in the containers will change during storage. Initially it will be temporarily low-foaming or non-foaming, with a latent foaming property. As time passes the foam-depressing agent is replaced by products of its decomposition and the foaming property will appear.
- Thus in a yet further aspect this invention provides an aqueous bleaching composition comprising a bleaching agent, a foaming synthetic detergent and an additional component which is
- (i) a foam-depressing agent or
- (ii) decomposition products thereof or
- (iii) a mixture of (i) and (ii).
- The invention extends of course to containers of the bleaching composition. A preferred feature made possible by this invention is that the containers are filled substantially full with the composition.
- The foam-depressing agent must be unstable in the composition. Foam-depressing agents which have been found very effective are silicones (more correctly polysiloxanes). These may be used in an amount which is at least 0.001% by weight of the composition. Amounts greater than 0.01% by weight will normally not be necessary, although amounts somewhat in excess of this may be used if desired, for instance up to 0.5% by weight of the composition.
- Polysiloxanes which can be employed as antifoam agents have the structure
- The preferred polysiloxanes are polydimethylsiloxanes where both R and R′ are methyl groups. Usually the molecular weight is from 500 to 200 000.
- Examples of suitable commercially available polydimethylsiloxanes are the "Silicone 200 Fluids", available from Dow Corning.
- The composition will generally contain from 1 to 15% by weight of the bleaching agent. As mentioned, the preferred bleaching agent is alkali metal hypochlorite, for example sodium hypochlorite. Other bleaching agents may be used, for example hydrogen peroxide. The time taken for the composition to regain its foaming properties will of course depend on the rate of reaction between the bleaching agent and the silicone. Thus, hydrogen peroxide would take somewhat longer than a like amount of hypochlorite to degrade the silicone but this merely necessitates some increase in the time for which the composition is stored after packing.
- Various foam-imparting detergents are available. Synthetic detergents are described in "Surface Active Agents" by Schwartz and Perry (Interscience 1949) and Volume II by Schwartz, Perry and Berch (Interscience 1958).
- The synthetic detergents preferably used in this invention are amine oxides, more preferably trialkyl amine oxides in which one alkyl group has from 8 to 20 carbon atoms while the other two have from 1 to 4 carbon atoms. An example is lauryl dimethyl amine oxide.
- The amount of surfactant included in the composition typically lies in the range from 0.05 to 1.5% by weight of the composition. Amounts somewhat greater than 1.5% by weight may be used if desired, for instance up to 5% by weight.
- Usually the composition also contains free alkali to provide a required alkaline pH. Other additives can be included, such as perfumes and colouring agents.
- The following Example illustrates the invention.
- Four bleaching compositions as set out in the Table below were prepared. The proportions stated in this Table are percentages by weight based on the whole composition as prepared.
- The foaming characteristics of the compositions were assessed by shaking a quantity of each composition in accordance with a standardised procedure and then observing the height of foam generated. The compositions were analysed for residual bleaching agent after a period of storage. These test results are included in the Table below.
Table sodium hypochlorite 5 5 5 5 lauryl dimethyl amine oxide 0.4 0.4 0.4 0.4 sodium hydroxide 0.5 0.5 0.5 0.5 perfume 0.06 0.06 0.06 0.06 silicone oil 0.01 0.005 0.001 - water q.s q.s q.s q.s Foam height (initial) 0 10 70 200 Foam height (after 1 week storage at room temperature) 75 70 85 125 Foam height (after 2 weeks storage at room temperature) 150 175 200 150 % sodium hypochlorite left after 8 weeks storage at 37°C 68 68 68 70 - This example shows that the initial foaming is significantly reduced, but that the foaming characteristics reappear after 1-2 weeks storage, while there is no substantial loss of bleaching agent.
Claims (10)
1. A bleaching composition obtainable by including a foam-depressing agent in an aqueous mixture of a bleaching agent and a foaming synthetic detergent, which foam-depressing agent is not stable therein, packing the composition in containers and optionally then storing the containers.
2. An aqueous bleaching composition comprising a bleaching agent, a foaming synthetic detergent and an additional component which is
(i) a foam-depressing agent or
(ii) decomposition products thereof or
(iii) a mixture of (i) and (ii).
3. A bieaching composition according to claim 1 or claim 2 wherein the bleaching agent is an alkali metal hypochlorite.
4. A bleaching composition according to any one of the preceding claims wherein the foam-depressing agent is a silicone.
5. A bleaching composition according to any one of the preceding claims wherein the synthetic detergent is a trialkyl amine oxide.
6. A bleaching composition according to any one of the preceding claims containing from 1% to 15% by weight of the bleaching agent, 0.05 to 1.5% by weight of the synthetic detergent and at least 0.001% of the foam-depressing agent.
7. A container of bleaching composition according to any one of the preceding claims.
8. A process for the production of an aqueous bleaching composition comprising an aqueous mixture of a bleaching agent and a foaming synthetic detergent, characterised by including a foam-depressing agent which is not stable in the mixture, and packing the composition in containers while foaming is inhibited by the presence of the foam-depressing agent.
9. A process according to claim 8 followed by storing the containers with the composition therein.
10. A container of bleaching composition produced and packed by the process of claim 8 or claim 9.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8807752 | 1988-03-31 | ||
| GB888807752A GB8807752D0 (en) | 1988-03-31 | 1988-03-31 | Bleaching composition |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP0335584A2 true EP0335584A2 (en) | 1989-10-04 |
| EP0335584A3 EP0335584A3 (en) | 1990-11-22 |
| EP0335584B1 EP0335584B1 (en) | 1994-11-30 |
Family
ID=10634470
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP89302882A Revoked EP0335584B1 (en) | 1988-03-31 | 1989-03-22 | Bleaching composition |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0335584B1 (en) |
| JP (1) | JPH01289900A (en) |
| AU (1) | AU616951B2 (en) |
| BR (1) | BR8901474A (en) |
| DE (1) | DE68919500T2 (en) |
| ES (1) | ES2065371T3 (en) |
| GB (1) | GB8807752D0 (en) |
| TR (1) | TR24043A (en) |
| ZA (1) | ZA892355B (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994024259A1 (en) * | 1993-04-15 | 1994-10-27 | Unilever Plc | Hygienic cleaning composition and apparatus for spraying said composition |
| US6537958B1 (en) | 1999-11-10 | 2003-03-25 | The Procter & Gamble Company | Bleaching compositions |
| WO2018052946A1 (en) * | 2016-09-15 | 2018-03-22 | Reoxcyn Innovation Group, Llc | Hypochlorite-based hand or medical instrument sanitizer |
| US10471003B2 (en) | 2016-05-18 | 2019-11-12 | Reoxcyn, Llc | Lubricant formulations |
| US10485827B2 (en) | 2016-01-19 | 2019-11-26 | Rdg Holdings, Inc. | Topical eye serum compositions, methods or preparing, and methods of use |
| US10543230B2 (en) | 2013-10-07 | 2020-01-28 | Rdg Holding, Inc. | Redox signaling gel formulation |
| US11857674B2 (en) | 2016-05-18 | 2024-01-02 | Reoxcyn, Llc | Lubricant formulations |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE755338A (en) * | 1969-08-29 | 1971-02-26 | Unilever Nv | BLEACHING COMPOSITIONS |
| EP0110544A1 (en) * | 1982-11-02 | 1984-06-13 | Imperial Chemical Industries Plc | Bleaching compositions |
| JPS6295365A (en) * | 1985-10-21 | 1987-05-01 | Mitsubishi Yuka Fine Chem Co Ltd | Printing ink cleaning liquid |
| US4752409A (en) * | 1985-06-14 | 1988-06-21 | Colgate-Palmolive Company | Thixotropic clay aqueous suspensions |
| JP2843027B2 (en) * | 1985-06-28 | 1999-01-06 | 花王株式会社 | Mold remover composition |
| GB8608292D0 (en) * | 1986-04-04 | 1986-05-08 | Unilever Plc | Thickened liquid bleaching composition |
| JPH0672239B2 (en) * | 1986-08-21 | 1994-09-14 | タイホ−工業株式会社 | Polishing cleaning method |
| NZ226174A (en) * | 1987-09-23 | 1991-03-26 | Colgate Palmolive Co | Aqueous cleaning composition; no- or low-phosphorus built mixture |
-
1988
- 1988-03-31 GB GB888807752A patent/GB8807752D0/en active Pending
-
1989
- 1989-03-22 EP EP89302882A patent/EP0335584B1/en not_active Revoked
- 1989-03-22 DE DE68919500T patent/DE68919500T2/en not_active Expired - Fee Related
- 1989-03-22 ES ES89302882T patent/ES2065371T3/en not_active Expired - Lifetime
- 1989-03-24 TR TR89/0251A patent/TR24043A/en unknown
- 1989-03-29 AU AU32231/89A patent/AU616951B2/en not_active Ceased
- 1989-03-30 JP JP1080233A patent/JPH01289900A/en active Pending
- 1989-03-30 ZA ZA892355A patent/ZA892355B/en unknown
- 1989-03-30 BR BR898901474A patent/BR8901474A/en active Search and Examination
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994024259A1 (en) * | 1993-04-15 | 1994-10-27 | Unilever Plc | Hygienic cleaning composition and apparatus for spraying said composition |
| US6537958B1 (en) | 1999-11-10 | 2003-03-25 | The Procter & Gamble Company | Bleaching compositions |
| US10543230B2 (en) | 2013-10-07 | 2020-01-28 | Rdg Holding, Inc. | Redox signaling gel formulation |
| US10485827B2 (en) | 2016-01-19 | 2019-11-26 | Rdg Holdings, Inc. | Topical eye serum compositions, methods or preparing, and methods of use |
| US12318404B2 (en) | 2016-01-19 | 2025-06-03 | Reoxcyn LLC | Hypochlorite formulations for wound healing |
| US10471003B2 (en) | 2016-05-18 | 2019-11-12 | Reoxcyn, Llc | Lubricant formulations |
| US11083689B2 (en) | 2016-05-18 | 2021-08-10 | Reoxcyn, Llc | Lubricant formulations |
| US11857674B2 (en) | 2016-05-18 | 2024-01-02 | Reoxcyn, Llc | Lubricant formulations |
| WO2018052946A1 (en) * | 2016-09-15 | 2018-03-22 | Reoxcyn Innovation Group, Llc | Hypochlorite-based hand or medical instrument sanitizer |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0335584A3 (en) | 1990-11-22 |
| ES2065371T3 (en) | 1995-02-16 |
| JPH01289900A (en) | 1989-11-21 |
| DE68919500T2 (en) | 1995-05-04 |
| AU3223189A (en) | 1989-10-05 |
| EP0335584B1 (en) | 1994-11-30 |
| ZA892355B (en) | 1990-12-28 |
| BR8901474A (en) | 1989-11-14 |
| TR24043A (en) | 1991-02-07 |
| GB8807752D0 (en) | 1988-05-05 |
| DE68919500D1 (en) | 1995-01-12 |
| AU616951B2 (en) | 1991-11-14 |
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