EP0434118B1 - Use of aminoxides as antistatic agents - Google Patents
Use of aminoxides as antistatic agents Download PDFInfo
- Publication number
- EP0434118B1 EP0434118B1 EP19900203230 EP90203230A EP0434118B1 EP 0434118 B1 EP0434118 B1 EP 0434118B1 EP 19900203230 EP19900203230 EP 19900203230 EP 90203230 A EP90203230 A EP 90203230A EP 0434118 B1 EP0434118 B1 EP 0434118B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- aminoxide
- fabrics
- alkyl
- carbon atoms
- weight
- 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
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 title claims description 34
- 239000002216 antistatic agent Substances 0.000 title description 8
- 239000004744 fabric Substances 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 229920000728 polyester Polymers 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- -1 alkyl aminoxide Chemical compound 0.000 claims description 5
- 239000002518 antifoaming agent Substances 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 229920002545 silicone oil Polymers 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 238000005406 washing Methods 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 3
- 125000001453 quaternary ammonium group Chemical group 0.000 description 3
- 235000013162 Cocos nucifera Nutrition 0.000 description 2
- 244000060011 Cocos nucifera Species 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- BACSFNBRIPFVDW-UHFFFAOYSA-N N-(2-methylheptadecan-2-yl)hydroxylamine Chemical compound CCCCCCCCCCCCCCCC(C)(C)NO BACSFNBRIPFVDW-UHFFFAOYSA-N 0.000 description 1
- HSOKJTAWWUMYPV-UHFFFAOYSA-N N-(2-methylpentadecan-2-yl)hydroxylamine Chemical compound CCCCCCCCCCCCCC(C)(C)NO HSOKJTAWWUMYPV-UHFFFAOYSA-N 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- SYELZBGXAIXKHU-UHFFFAOYSA-N dodecyldimethylamine N-oxide Chemical compound CCCCCCCCCCCC[N+](C)(C)[O-] SYELZBGXAIXKHU-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 238000009940 knitting Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 230000001050 lubricating effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229960001749 practolol Drugs 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/144—Alcohols; Metal alcoholates
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/388—Amine oxides
Definitions
- the present invention relates to the use of aminoxide as antistatic agents for reducing the propensity of fabrics to accumulate electrostatic charges.
- Electrostatic charges on fabrics is also undesirable in manufacturing processes of sheets, films, filaments, etc, as the charges tend to cause the articles to cling together or to the processing equipment. Electrostatic charges are particularly dangerous in the manufacturing process of integrated circuits, especially of the MOS-type, as these may be irreversibly damaged by such charges. It is therefore essential that the protective clothing which is worn by the laborers in this branch of industry is treated in such way that accumulation of electrostatic charges is prevented or effectively reduced.
- US-A-4014,800 corresponding to FR-A-2230790 discloses lubricating compositions for fibres for use in the manufacturing and processing of those fibres by such methods as knitting and weaving.
- the lubricant compositions incorporate amine oxides as anti-static agents.
- GB-A-1066763 discloses amine oxides and a number of uses of them including use as softening agents for textiles and as shampoos with anti-static effect.
- US-A-3447956 equivalent to FR-A-1545719 teaches a process of introducing amine oxide, which is dissolved in lower alkanols, into fibrous material and then causing the amine oxide to swell the fibres as a means of strengthening the material.
- the present invention relates to the use of aminoxides for treating fabrics in order to reduce the propensity of the fabrics to accumulate electrostatic charges, especially when the fabrics comprise polyester.
- the invention provides a method for reducing the propensity of fabrics to accumulate electrostatic charges which comprises treating the fabrics with an aqueous liquor formed by adding to water an aqueous antistatic composition which comprises 10-80% by weight of aminoxide and 2.5-20% by weight of a lower alkanol.
- the invention provides an aqueous antistatic composition comprising:
- Aminoxides are well-known surfactants having a cationic character at low and neutral pH and a noionic character at alkaline pH.
- Aminoxides which are advantageously used in the present invention correspond to the general formula: wherein R 1 and R 3 are independently CH 3 or C 2 H 4 OH and R 2 is an alkyl group having 12 to 18 carbon atoms.
- R 2 is an alkyl group having 14 to 16 carbon atoms.
- Such aminoxides are commercially available, for instance from AKZO Chemie under the trade name "Aromox”. They are supplied as solutions having an active content of 30 to 40% by weight in wa- ter/isopropanol (50/50) or in water.
- the antistatic compositions that are used in the process of the present invention are aqueous compositions comprising 10 to 80% by weight of aminoxide and 2.5 to 20% by weight of a lower alkanol, preferably isopropanol. Preferably they comprise 20 to 40% aminoxide and 5 to 10% isopropanol.
- compositions in which the aminoxide is a mixture of a dimethyl alkyl aminoxide and a bis-(2-hydroxyethyl) alkyl aminoxide, wherein the alkyl groups comprise 12 to 18 carbon atoms, exhibit a more pronounced antistatic effect than compositions which contain either one of these aminoxides alone.
- the antistatic compositions used according to the invention further comprise an anti-foam agent, preferably a silicone oil, in an amount of 0.01 to 1.0 wt%, calculated on the total composition.
- an anti-foam agent preferably a silicone oil
- compositions may be used after or in the rinse cycle of a wash process for the treatment of fabrics in an amount of 1 to 100 g, preferably 3 to 20 g per kg wash load.
- process of the present invention is primarily suitable for industrial applications, such as the industrial cleaning of overalls.
- the anti-static compositions may also be used in the pre-wash cycle of such a fabric washing process.
- the number of fluffs was significantly reduced. This proved to be a significant advantage for the washing of coloured linen for surgery rooms were conventional wash processes inevitably leave a large number of fluffs which have to be removed manually.
- Aromox T/12, DMCD and DM16D contain 40 % by weight of aminoxide in a solvent mixture consisting of 50 % isopropanol and 50 % water.
- Aromox DMMCD-W and DM14D-W contain 30 % by weight of aminoxide in water.
- the surface resistivity of the overalls was then determined by measuring the resistance of the fabric according to British Standard 5958:1980 using a Philips Model 262 resistivity meter. The results are also shown in Table I. In all cases, the chemical damage which the fabrics incurred after several washes was much less than when a conventional quaternary ammonium antistatic composition was used.
- Examples 1 to 21 all illustrate the use aspect of the present invention, Examples 1 to 9 illustrating the use of single aminoxides and Examples 10 to 21 illustrating the use of combinations of aminoxides which give rise to synergistic antistatic effects.
- Examples 10 to 13 and 16 to 21 are illustrative of antistatic compositions within the scope of the third, composition, aspect of the invention, the methods of use of these particular compositions being illustrative of methods within the scope of the second, method, aspect of the invention.
- an anti-static composition according to the invention was compared with the effect caused by a conventional anti-static agent of the quaternary ammonium type.
- Samples of three different types of polyester fabrics were soaked for 10 minutes at 40 °C and at a liquid to cloth ratio of 20 to 1, using 2 g anti- static agent per litre. Subsequently, the samples were dried for 20 minutes at 60 ° C. This procedure was repeated 25 times and then the tensile strength of a test cloth having a width of 5 cm was measured (in kg) on a Louis Schopper tensile strength meter Type MT34. The tensile strength is believed to be a good measure of the chemical damage due to the anti-static treatment.
- the results for three different polyester fabrics are shown below.
- Example 20 leads to less chemical damage on all three different types of polyester fabric then the conventional anti-static agent of the quaternary ammonium type.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
- The present invention relates to the use of aminoxide as antistatic agents for reducing the propensity of fabrics to accumulate electrostatic charges.
- Many types of fabric have a tendency to accumulate electrical charges. Clothes which are manufactured using such fabrics are then likely to become carriers of electrostatic charges. This is unpleasant for the person who is wearing the clothing, as the mutual attraction of oppositely charged surfaces may lead to lead to clinging of the clothing to the body and to undergarments. Furthermore, static charges may contribute to the soiling of garments, draperies and other textile products by attracting oppositely charged particles of dust and dirt from the atmosphere onto the charged fabric.
- The generation of electrostatic charges on fabrics is also undesirable in manufacturing processes of sheets, films, filaments, etc, as the charges tend to cause the articles to cling together or to the processing equipment. Electrostatic charges are particularly dangerous in the manufacturing process of integrated circuits, especially of the MOS-type, as these may be irreversibly damaged by such charges. It is therefore essential that the protective clothing which is worn by the laborers in this branch of industry is treated in such way that accumulation of electrostatic charges is prevented or effectively reduced.
- In order to reduce the propensity of fabrics to accumulate electrostatic charges it is known to provide the fabric with a finish of substances which have a high conductivity, such as quaternary ammonium compounds. Such antistatic agents may be added to the fabric in the rinse cycle of the fabric washing process and may provide a surface resistivity in the order of 109 ohm/square.
- However, it was found that the use of quaternary ammonium compounds as antistatic agents for fabrics may lead to serious chemical damage to the fabric upon repeated washing, especially if the fabric comprises polyester. This damage was found to increase with the amount of quaternary ammonium compound used, such that a compromise must be made between an effective antistatic treatment and an economically acceptable amount of damage to the protective clothing.
- We have now found that this damage may be reduced or obviated when an aminoxide is used for reducing the propensity of fabrics to accumulate electrostatic charges.
- US-A-4014,800 corresponding to FR-A-2230790 discloses lubricating compositions for fibres for use in the manufacturing and processing of those fibres by such methods as knitting and weaving. The lubricant compositions incorporate amine oxides as anti-static agents.
- GB-A-1066763 discloses amine oxides and a number of uses of them including use as softening agents for textiles and as shampoos with anti-static effect.
- US-A-3447956 equivalent to FR-A-1545719 teaches a process of introducing amine oxide, which is dissolved in lower alkanols, into fibrous material and then causing the amine oxide to swell the fibres as a means of strengthening the material.
- US-A-3501335 teaches the softening of fabrics with amine oxides.
- According to a first aspect, the present invention relates to the use of aminoxides for treating fabrics in order to reduce the propensity of the fabrics to accumulate electrostatic charges, especially when the fabrics comprise polyester.
- According to a second aspect, the invention provides a method for reducing the propensity of fabrics to accumulate electrostatic charges which comprises treating the fabrics with an aqueous liquor formed by adding to water an aqueous antistatic composition which comprises 10-80% by weight of aminoxide and 2.5-20% by weight of a lower alkanol.
- According to a third aspect, the invention provides an aqueous antistatic composition comprising:
- 10 to 80% by weight of aminoxide, and
- 2.5 to 20% by weight of a lower alkanol,
wherein the aminoxide is a mixture of a dimethyl alkyl aminoxide and a bis-(2-hydroxyethyl) alkyl aminoxide, in which the alkyl groups comprise 12 to 18 carbon atoms. - Aminoxides are well-known surfactants having a cationic character at low and neutral pH and a noionic character at alkaline pH. Aminoxides which are advantageously used in the present invention correspond to the general formula:
- Such aminoxides are commercially available, for instance from AKZO Chemie under the trade name "Aromox". They are supplied as solutions having an active content of 30 to 40% by weight in wa- ter/isopropanol (50/50) or in water.
- The antistatic compositions that are used in the process of the present invention are aqueous compositions comprising 10 to 80% by weight of aminoxide and 2.5 to 20% by weight of a lower alkanol, preferably isopropanol. Preferably they comprise 20 to 40% aminoxide and 5 to 10% isopropanol.
- Surprisingly, it was also found that such antistatic compositions in which the aminoxide is a mixture of a dimethyl alkyl aminoxide and a bis-(2-hydroxyethyl) alkyl aminoxide, wherein the alkyl groups comprise 12 to 18 carbon atoms, exhibit a more pronounced antistatic effect than compositions which contain either one of these aminoxides alone.
- It is advantageous when the antistatic compositions used according to the invention further comprise an anti-foam agent, preferably a silicone oil, in an amount of 0.01 to 1.0 wt%, calculated on the total composition.
- The compositions may be used after or in the rinse cycle of a wash process for the treatment of fabrics in an amount of 1 to 100 g, preferably 3 to 20 g per kg wash load. Although not exclusively, the process of the present invention is primarily suitable for industrial applications, such as the industrial cleaning of overalls.
- However, according to the invention, the anti-static compositions may also be used in the pre-wash cycle of such a fabric washing process. In that case it was surprisingly found that the number of fluffs was significantly reduced. This proved to be a significant advantage for the washing of coloured linen for surgery rooms were conventional wash processes inevitably leave a large number of fluffs which have to be removed manually.
- The invention will now be further illustrated by means of the following examples in which the amounts are given as % by weight, unless otherwise indicated. In the Examples, the following abbreviation is used:
- ISA : lsopropanol
- The following aminoxide products were used which are commercially available from Akzo Chemie: Aromox T/12 : bis-(2-hydroxyethyI) tallow aminoxide
- Aromox DMCD : dimethyl coconut aminoxide
- Aromox DM16D : dimethyl hexadecyl aminoxide
- Aromox DMMCD-W : dimethyl coconut aminoxide, purified
- Aromox DM14D-W : dimethyl tetradecyl aminoxide
- Aromox T/12, DMCD and DM16D contain 40 % by weight of aminoxide in a solvent mixture consisting of 50 % isopropanol and 50 % water. Aromox DMMCD-W and DM14D-W contain 30 % by weight of aminoxide in water.
- 28 kg overalls made of polyester comprising fabric were subjected to a conventional industrial fabric washing process in a Spencer O.E. washing machine. The dosage of detergent product was 5 g/kg and the water hardness was 0 degrees German Hardness. The process consisted of a prewash of 2.5 minutes at 40 °C, a main wash of 6.5 minutes at 55 ° C followed by two rinse cycles of 2.5 minutes each. After the last rinse cycle, the wash load was treated for 5 minutes at 18 °C with the amounts of the various antistatic compositions as indicated in Table I. After draining the overalls were removed and dried for 20 minutes in a tumble dryer at a temperature of 50 °C. The surface resistivity of the overalls was then determined by measuring the resistance of the fabric according to British Standard 5958:1980 using a Philips Model 262 resistivity meter. The results are also shown in Table I. In all cases, the chemical damage which the fabrics incurred after several washes was much less than when a conventional quaternary ammonium antistatic composition was used.
- In the Examples set out in Table I below, Examples 1 to 21 all illustrate the use aspect of the present invention, Examples 1 to 9 illustrating the use of single aminoxides and Examples 10 to 21 illustrating the use of combinations of aminoxides which give rise to synergistic antistatic effects. Examples 10 to 13 and 16 to 21 (but not Examples 1 to 9 and 14 and 15) are illustrative of antistatic compositions within the scope of the third, composition, aspect of the invention, the methods of use of these particular compositions being illustrative of methods within the scope of the second, method, aspect of the invention.
- The effect of an anti-static composition according to the invention was compared with the effect caused by a conventional anti-static agent of the quaternary ammonium type. Samples of three different types of polyester fabrics were soaked for 10 minutes at 40 °C and at a liquid to cloth ratio of 20 to 1, using 2 g anti- static agent per litre. Subsequently, the samples were dried for 20 minutes at 60 ° C. This procedure was repeated 25 times and then the tensile strength of a test cloth having a width of 5 cm was measured (in kg) on a Louis Schopper tensile strength meter Type MT34. The tensile strength is believed to be a good measure of the chemical damage due to the anti-static treatment. The results for three different polyester fabrics are shown below.
- These results show that the composition of Example 20 according to the invention leads to less chemical damage on all three different types of polyester fabric then the conventional anti-static agent of the quaternary ammonium type.
Claims (15)
wherein the aminoxide is a mixture of a dimethyl alkyl aminoxide and a bis-(2-hydroxyethyl) alkyl aminoxide, in which the alkyl groups comprise 12 to 18 carbon atoms.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8928512 | 1989-12-18 | ||
| GB898928512A GB8928512D0 (en) | 1989-12-18 | 1989-12-18 | Antistatic compositions |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| EP0434118A2 EP0434118A2 (en) | 1991-06-26 |
| EP0434118A3 EP0434118A3 (en) | 1991-09-11 |
| EP0434118B1 true EP0434118B1 (en) | 1995-11-22 |
| EP0434118B2 EP0434118B2 (en) | 1998-10-28 |
Family
ID=10668098
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP19900203230 Expired - Lifetime EP0434118B2 (en) | 1989-12-18 | 1990-12-07 | Use of aminoxides as antistatic agents |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP0434118B2 (en) |
| AU (1) | AU633166B2 (en) |
| CA (1) | CA2032184C (en) |
| DE (1) | DE69023747T3 (en) |
| ES (1) | ES2081345T5 (en) |
| FI (1) | FI98735C (en) |
| GB (1) | GB8928512D0 (en) |
| NZ (1) | NZ236496A (en) |
| ZA (1) | ZA9010182B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102015214056A1 (en) * | 2015-07-24 | 2017-01-26 | Henkel Ag & Co. Kgaa | Detergency enhancing hydroxyamine oxides |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB538711A (en) * | 1939-10-30 | 1941-08-13 | Tootal Broadhurst Lee Co Ltd | Improvements in treating materials with alkaline reagents and reagents therefor |
| GB1066763A (en) * | 1964-05-11 | 1967-04-26 | Marconi Products Ltd | Production and'use of amine oxide surface-active agents |
| US3501335A (en) * | 1965-11-26 | 1970-03-17 | Lever Brothers Ltd | Fabric conditioner |
| FR1545719A (en) * | 1966-09-02 | 1968-11-15 | Eastman Kodak Co | Improvement of the mechanical resistance of fibrous products, and new fibrous products with improved resistance |
| ES426477A1 (en) * | 1973-05-26 | 1976-07-01 | Hoechst Ag | Fiber-lubricating compositions |
-
1989
- 1989-12-18 GB GB898928512A patent/GB8928512D0/en active Pending
-
1990
- 1990-12-07 EP EP19900203230 patent/EP0434118B2/en not_active Expired - Lifetime
- 1990-12-07 ES ES90203230T patent/ES2081345T5/en not_active Expired - Lifetime
- 1990-12-07 DE DE1990623747 patent/DE69023747T3/en not_active Expired - Fee Related
- 1990-12-12 FI FI906100A patent/FI98735C/en not_active IP Right Cessation
- 1990-12-13 CA CA 2032184 patent/CA2032184C/en not_active Expired - Fee Related
- 1990-12-14 AU AU68067/90A patent/AU633166B2/en not_active Ceased
- 1990-12-17 NZ NZ23649690A patent/NZ236496A/en unknown
- 1990-12-18 ZA ZA9010182A patent/ZA9010182B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI906100A0 (en) | 1990-12-12 |
| CA2032184A1 (en) | 1991-06-19 |
| DE69023747T3 (en) | 1999-04-15 |
| GB8928512D0 (en) | 1990-02-21 |
| ES2081345T3 (en) | 1996-03-01 |
| EP0434118B2 (en) | 1998-10-28 |
| CA2032184C (en) | 1999-11-30 |
| EP0434118A2 (en) | 1991-06-26 |
| EP0434118A3 (en) | 1991-09-11 |
| AU6806790A (en) | 1991-06-20 |
| FI906100A (en) | 1991-06-19 |
| ZA9010182B (en) | 1992-08-26 |
| ES2081345T5 (en) | 1999-02-16 |
| FI98735B (en) | 1997-04-30 |
| DE69023747D1 (en) | 1996-01-04 |
| DE69023747T2 (en) | 1996-04-18 |
| AU633166B2 (en) | 1993-01-21 |
| NZ236496A (en) | 1992-08-26 |
| FI98735C (en) | 1997-08-11 |
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