EP0674701A1 - Wässrige textilweichmacher-dispersionen. - Google Patents
Wässrige textilweichmacher-dispersionen.Info
- Publication number
- EP0674701A1 EP0674701A1 EP94902704A EP94902704A EP0674701A1 EP 0674701 A1 EP0674701 A1 EP 0674701A1 EP 94902704 A EP94902704 A EP 94902704A EP 94902704 A EP94902704 A EP 94902704A EP 0674701 A1 EP0674701 A1 EP 0674701A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- fatty acid
- mole
- weight
- atoms
- ethylene oxide
- 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
- 239000006185 dispersion Substances 0.000 title claims abstract description 29
- 239000004753 textile Substances 0.000 title claims abstract description 20
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims abstract description 16
- 239000002270 dispersing agent Substances 0.000 claims abstract description 15
- 239000000194 fatty acid Substances 0.000 claims description 29
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 28
- 229930195729 fatty acid Natural products 0.000 claims description 28
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 16
- 150000004665 fatty acids Chemical class 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- -1 hydroxy fatty acid Chemical class 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 9
- 239000003792 electrolyte Substances 0.000 claims description 7
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 claims description 6
- 239000004014 plasticizer Substances 0.000 claims description 5
- 229920005862 polyol Polymers 0.000 claims description 5
- 150000002191 fatty alcohols Chemical class 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 3
- 239000002979 fabric softener Substances 0.000 claims description 3
- 229910001629 magnesium chloride Inorganic materials 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 239000003760 tallow Substances 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 150000003973 alkyl amines Chemical class 0.000 claims description 2
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000004744 fabric Substances 0.000 claims description 2
- 125000002811 oleoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 150000003077 polyols Chemical class 0.000 claims description 2
- 229940125810 compound 20 Drugs 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000004593 Epoxy Substances 0.000 description 3
- 238000007142 ring opening reaction Methods 0.000 description 3
- 239000003549 soybean oil Substances 0.000 description 3
- 235000012424 soybean oil Nutrition 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- RKHXDCVAPIMDMG-UHFFFAOYSA-N 9-hydroxyoctadecanoic acid Chemical compound CCCCCCCCCC(O)CCCCCCCC(O)=O RKHXDCVAPIMDMG-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 238000006735 epoxidation reaction Methods 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- AGNTUZCMJBTHOG-UHFFFAOYSA-N 3-[3-(2,3-dihydroxypropoxy)-2-hydroxypropoxy]propane-1,2-diol Chemical compound OCC(O)COCC(O)COCC(O)CO AGNTUZCMJBTHOG-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 235000021319 Palmitoleic acid Nutrition 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 1
- 125000001924 fatty-acyl group Chemical group 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 239000002351 wastewater Substances 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
- C11D3/0005—Other compounding ingredients characterised by their effect
- C11D3/001—Softening compositions
- C11D3/0015—Softening compositions liquid
-
- 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
- C11D1/38—Cationic compounds
- C11D1/62—Quaternary ammonium compounds
Definitions
- the present invention relates to aqueous fabric softener dispersions which, despite a particularly high content of fabric softening active ingredients, have a low viscosity which does not increase, or increases only insignificantly, even after prolonged storage.
- Aqueous textile plasticizer dispersions tend to thicken when stored for a long time, especially at temperatures below or above room temperature. This behavior is particularly pronounced in textile softener dispersions with a high active ingredient content.
- the commercial textile softener concentrates contain about 15 to 25% by weight of active ingredient.
- To produce storage-stable dispersions a very low starting viscosity is generally set using different electrolytes. With an even higher active ingredient content, however, a noticeable increase in viscosity is observed even in the presence of electrolyte during storage, which either occurs immediately after production or during storage.
- the object of the present invention was therefore to provide an aqueous textile plasticizer dispersion with a high active ingredient content, the viscosity of which is low and which does not increase significantly even during storage and which can easily be thinned further with cold water.
- the proportion of nonionic, non-textile softening dispersant should be as low as possible.
- the textile-softening cationic active ingredient should moreover be present in an amount of more than 15% by weight, it should impart good softness to the treated textiles, not impair the ability to reuse them and be easily and rapidly biodegraded in the waste water.
- the present invention accordingly relates to an aqueous textile softener dispersion containing quaternary ammonium compounds and nonionic dispersants which soften the textile, characterized in that the dispersion
- b) contains 0.001-0.5% by weight of nonionic dispersants which are selected from
- the quaternary ammonium compounds mentioned are readily and rapidly biodegradable because of the ester or acid groups contained in the long residues and have therefore recently gained interest.
- the compounds mentioned include, for example, the compounds known from DE-A-16 19058, DE-A-19 35499 or US Pat. No. 3,915,867 with 1, 2 or 3 fatty acyloxyalkyl radicals on the nitrogen atom. These compounds can be easily prepared, for example, by esterification of alkanolamines with fatty acid or by transesterification of fatty acid esters with alkanolamine and subsequent quaternization. Corresponding processes for the production on an industrial scale have also been known for a long time; Compounds produced by these processes are commercially available compounds.
- Compounds which are of particular interest with regard to the stability of the viscosity of the aqueous dispersions prepared therewith are those whose fatty acyl groups are wholly or partly unsaturated.
- Derive th fatty acids which are at least 30, preferably at least 55% in cis form.
- Suitable quaternary ammonium compounds are also known from US 5,066,414, EP 0293 953 A2, EP 0 309052 A2 and EP 0345842 A2.
- Suitable quaternary ammonium compounds also include those derived from dimethylaminopropanediol-1,2 with two ester groups. They are described, for example, in DE-A-27 28841. A manufacturing process leading to such products with a low pour point is the subject of EP-A-420465.
- the quaternary ammonium compounds mentioned can surprisingly also be processed into viscosity-stable aqueous dispersions if the content of quaternary ammonium compounds is particularly high, ie for example 15 to 60% by weight, based on the aqueous dispersion, preferably 20 to 40% by weight .-%. This has been achieved by the selection according to the invention of nonionic dispersants * even at contents of less than 0.5% by weight of the dispersants.
- Hydroxy fatty acids are understood in particular to mean ricinole fatty acid and 9-hydroxystearic acid. Also suitable as hydroxy fatty acids in the sense of this invention are hydroxyl-containing fatty acids which are obtained by epoxidation of palmitoleic acid, oleic acid or erucic acid and subsequent epoxy ring opening with protic reagents such as e.g. Water, alcohols or carboxylic acids are available.
- the adducts of 3-100 moles of ethylene oxide with 1 / mole of a polyol fatty alcohol ester include, for example, ethoxylates of fatty acids. remono- and -diglycerides, of sorbitan mono-, di- and sesquiesters of Ci2-C22 fatty acids, on mono- and di-fatty acid esters of di- and triglycerol as well as on triglycerides such as castor oil.
- ethylene oxide addition products on ring opening products of epoxidized triglycerides such as those e.g. are obtained by epoxidation of soybean oil, hydrogenation or reaction (epoxy ring opening) with protic compounds such as e.g. with H2O, carboxylic acids or alcohols with 1 - 10 C atoms and subsequent addition of ethylene oxide.
- protic compounds such as e.g. with H2O, carboxylic acids or alcohols with 1 - 10 C atoms and subsequent addition of ethylene oxide.
- Such products are e.g. known from DE 39 23 394 AI.
- ethylene oxide adducts of fatty acid (Ci2-C22) - me methyl ester are preferred.
- Ethylene oxide addition products which additionally contain 1-10 oxypropyl groups and which are obtained by addition of propylene oxide and ethylene oxide, simultaneously or in succession, are also suitable.
- the selected dispersants to be used according to the invention are already in an added amount of 0.001 to 0.1% by weight in preferred textile plasticizer dispersions capable of markedly reducing the viscosity and preventing subsequent thickening during storage to such an extent that the flow and Pourability and good further dilutability with water are maintained.
- RCO is an oleoyl residue derived from tallow fatty acid
- only 0.01-0.1% by weight of the dispersant is required to stabilize the viscosity of a dispersion containing 20-40% by weight of the quaternary ammonium compound.
- aqueous textile softener dispersions do not have a low initial viscosity, for example through the use of quaternary ammonium compounds of a suitable structure, it is advisable to set a low viscosity by adding an electrolyte.
- Suitable electrolytes are, for example, sodium chloride, sodium acetate, magnesium sulfate or calcium chloride and in particular magnesium chloride. Small amounts are also sufficient to set a low initial viscosity by adding an electrolyte.
- the electrolyte is present in the dispersion in concentrations of 0.01 to 3% by weight, based on the finished dispersion.
- the dispersions mentioned are distinguished by the fact that their initial viscosity does not increase or only increases slightly after production, even after prolonged storage in a wide temperature range, that they have a high active ingredient content, and that they can easily be diluted with cold water, which is particularly noticeable when washing it in automatic washing machines, and that the textiles treated with it do not only Chen grip but also have good rewettability, which is particularly important for textiles that are worn on the skin.
- aqueous textile plasticizer dispersions the 34% by weight of a compound of the formula I (Stepante ⁇ (R) - VS90 as a textile-softening, quaternary ammonium compound), an esterification product of triethanolamine quaternized with dimethyl sulfate with two Moles of tallow fatty acid), have high viscosity stability when very small amounts of non-ionic dispersants are added.
- the comparative batches without dispersant or with fatty alcohol ethoxylates with only 5 or 7 moles of ethylene oxide (example 9V, 10V) already show an unacceptable increase in viscosity after 1 week of storage.
- the viscosity (Pas) was measured in all cases using a Brookfield rotary viscometer with spindle 2 and 20 revolutions per minute at 20 ° C.
- the textile softener dispersions tested have the following composition:
- Viscosity (20 ° C)
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)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Colloid Chemistry (AREA)
Description
Claims
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4242480A DE4242480A1 (de) | 1992-12-16 | 1992-12-16 | Wäßrige Textilweichmacher-Dispersionen |
DE4242480 | 1992-12-16 | ||
PCT/EP1993/003441 WO1994013772A1 (de) | 1992-12-16 | 1993-12-07 | Wässrige textilweichmacher-dispersionen |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0674701A1 true EP0674701A1 (de) | 1995-10-04 |
EP0674701B1 EP0674701B1 (de) | 1997-06-18 |
Family
ID=6475439
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP94902704A Expired - Lifetime EP0674701B1 (de) | 1992-12-16 | 1993-12-07 | Wässrige textilweichmacher-dispersionen |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP0674701B1 (de) |
AT (1) | ATE154632T1 (de) |
DE (2) | DE4242480A1 (de) |
ES (1) | ES2102809T3 (de) |
WO (1) | WO1994013772A1 (de) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5916863A (en) | 1996-05-03 | 1999-06-29 | Akzo Nobel Nv | High di(alkyl fatty ester) quaternary ammonium compound from triethanol amine |
US5919750A (en) * | 1997-07-24 | 1999-07-06 | Akzo Nobel Nv | Fabric softener composition |
DE10134224B4 (de) * | 2001-07-13 | 2012-12-20 | Clariant Produkte (Deutschland) Gmbh | Additive zur Inhibierung der Gashydratbildung |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2482636A1 (fr) * | 1980-05-14 | 1981-11-20 | Lesieur Cotelle Et Associes Sa | Composition adoucissante concentree pour fibres textiles |
DE3218667A1 (de) * | 1982-05-18 | 1983-11-24 | Hoechst Ag, 6230 Frankfurt | Konzentrierte waescheweichspuelmittel |
DE3501521A1 (de) * | 1985-01-18 | 1986-07-24 | Henkel KGaA, 4000 Düsseldorf | Waessriges konzentriertes textilweichmachungsmittel |
GB8818593D0 (en) * | 1988-08-04 | 1988-09-07 | Albright & Wilson | Fabric conditioners |
GB8916307D0 (en) * | 1989-07-17 | 1989-08-31 | Unilever Plc | Fabric softening composition |
GB9115255D0 (en) * | 1991-07-15 | 1991-08-28 | Unilever Plc | Fabric softening composition |
-
1992
- 1992-12-16 DE DE4242480A patent/DE4242480A1/de not_active Withdrawn
-
1993
- 1993-12-07 AT AT94902704T patent/ATE154632T1/de active
- 1993-12-07 DE DE59306802T patent/DE59306802D1/de not_active Expired - Lifetime
- 1993-12-07 WO PCT/EP1993/003441 patent/WO1994013772A1/de active IP Right Grant
- 1993-12-07 EP EP94902704A patent/EP0674701B1/de not_active Expired - Lifetime
- 1993-12-07 ES ES94902704T patent/ES2102809T3/es not_active Expired - Lifetime
Non-Patent Citations (1)
Title |
---|
See references of WO9413772A1 * |
Also Published As
Publication number | Publication date |
---|---|
EP0674701B1 (de) | 1997-06-18 |
DE4242480A1 (de) | 1994-06-23 |
WO1994013772A1 (de) | 1994-06-23 |
ES2102809T3 (es) | 1997-08-01 |
ATE154632T1 (de) | 1997-07-15 |
DE59306802D1 (de) | 1997-07-24 |
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