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WO1993013194A1 - Activateurs de blanchiment sous forme granulaire (ii) - Google Patents

Activateurs de blanchiment sous forme granulaire (ii) Download PDF

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Publication number
WO1993013194A1
WO1993013194A1 PCT/EP1992/002909 EP9202909W WO9313194A1 WO 1993013194 A1 WO1993013194 A1 WO 1993013194A1 EP 9202909 W EP9202909 W EP 9202909W WO 9313194 A1 WO9313194 A1 WO 9313194A1
Authority
WO
WIPO (PCT)
Prior art keywords
granulate
binder
granules
weight
bleach activator
Prior art date
Application number
PCT/EP1992/002909
Other languages
German (de)
English (en)
Inventor
Volker Bauer
Jochen Jacobs
Christiane Zeise
Uwe Fassbach
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Henkel Kommanditgesellschaft Auf Aktien filed Critical Henkel Kommanditgesellschaft Auf Aktien
Priority to DE59206759T priority Critical patent/DE59206759D1/de
Priority to KR1019940702218A priority patent/KR940703910A/ko
Priority to JP5511402A priority patent/JPH07502551A/ja
Priority to EP93901014A priority patent/EP0618960B1/fr
Publication of WO1993013194A1 publication Critical patent/WO1993013194A1/fr

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
    • C11D3/39—Organic or inorganic per-compounds
    • 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
    • C11D3/39—Organic or inorganic per-compounds
    • C11D3/3902—Organic or inorganic per-compounds combined with specific additives
    • C11D3/3905—Bleach activators or bleach catalysts
    • C11D3/3935—Bleach activators or bleach catalysts granulated, coated or protected
    • 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
    • C11D3/39—Organic or inorganic per-compounds
    • C11D3/3902—Organic or inorganic per-compounds combined with specific additives
    • C11D3/3905—Bleach activators or bleach catalysts
    • C11D3/3907—Organic compounds

Definitions

  • the invention relates to new pourable and free-flowing granules which contain bleach activators for textile washing embedded in a binder phase as the main component, the binder phase containing surfactants which are solid at room temperature and moderately elevated temperatures.
  • the invention further relates to a method for producing these new bleach activator granules.
  • Inorganic peroxy compounds which dissolve in water with the liberation of hydrogen peroxide have long been used as oxidizing agents for disinfection and bleaching purposes.
  • the oxidizing effect of these substances in dilute solutions depends strongly on the temperature.
  • a sufficiently rapid bleaching of soiled textiles can only be achieved with perborate in alkaline bleaching liquors at temperatures above 60 ° C.
  • the oxidation effect of the inorganic per compounds can be improved by adding activators, for which numerous proposals have become known in the literature.
  • the addition of these activators can increase the bleaching effect of aqueous peroxide liquors to such an extent that they are already active in the temperature range from 30 to 60 ° C., ie. H. at temperatures which are required for washing delicate textiles.
  • these activators are highly sensitive to hydrolysis, especially in the presence of the alkalis which are generally customary in detergents.
  • the problems derived from this for the storage stability of the textile detergents are exacerbated by the fact that the activators are often poorly soluble in water, so that finely powdered materials with rapid dispersibility should be used. This very finely divided form allows due to increased surface area the increased hydrolysis of the activators during their storage.
  • the bleach activator component in the form of separately produced granules to be added to the dry washing or cleaning agent mixtures, the agglomerates of very fine bleaching agent particles being coated with auxiliaries.
  • the most varied organic and inorganic substances have been proposed as granulation aids and coating materials for such activator granules.
  • surfactant compounds from the classes of anionic, cationic and / or nonionic surfactants, polymeric materials or waxes which are solid at room temperature is known in particular.
  • the earlier application P 40 24 759.7 relates to granules in which the finely divided bleach activator is embedded in a practically water-free phase serving as a binder from a mixture of anionic and nonionic surfactant compounds, these granules being produced by extrusion of the plasticized mixture at elevated temperature.
  • these granules either proved to be too slowly soluble at low temperatures or were so brittle that an unacceptably high proportion of fine-grained material was obtained when the granules were rounded.
  • the object of the present invention was therefore to avoid the above-mentioned disadvantages of the previous granules without giving up their advantages, in particular the high storage stability and the ease of manufacture.
  • the invention relates to a pourable and free-flowing granulate which contains bleach activators for textile washing as the main constituent as a finely disperse solid phase embedded in a practically anhydrous phase which penetrates the granule grain and serves as a binder and which is obtained by extrusion of a practically water-free mixture of bleach activator, Anionic surfactant, solubilization aids and, if appropriate, further additives is produced.
  • Another object of the invention is a process for the production of the granules, in which the finely divided bleach activator is premixed with the other components, the mixture of substances is homogenized at preferably elevated temperature to form an extrudable mass and extruded in extruded form using increased pressure, the emerging strands, if appropriate after cooling, cuts into short pieces and rounds off these pieces if necessary and, if desired, classified according to size.
  • the mixture of anionic surfactant and solubilizing aid which serves as the binder is preferably selected such that this mixture only softens at temperatures above the highest usual storage temperatures, ie above temperatures of about 35 to 40 ° C.
  • the granulation then takes place in the temperature range above it, and if temperature-sensitive bleach activators or granulate components are used, corresponding upper limit temperatures must be maintained. Preferred the working temperatures during the granulation are not above
  • the anionic surfactant component may be chosen as the larger proportion in the binder mixture. It is particularly preferred here to use corresponding anionic surfactant compounds which are solid at room temperature and granulate formation temperature and which can make up at least 55% by weight and up to 98% by weight of the binder mixture.
  • the anionic surfactant content is in the range from 60 to 95% by weight, in particular 60 to 85% by weight, based on the weight of the binder mixture. Based on the total weight of the granulate, the proportion is preferably 4 to 25% by weight, in particular 6 to 15% by weight.
  • Suitable solid anionic surfactants are the solid components known in detergent technology, in particular in the context of textile detergents, which belong in particular to the following classes of substances: alkyl sulfates, alkyl sulfonates, alkylarylsulfonates, sulfonated fatty acid esters and / or beefs.
  • Particularly suitable anionic surfactants are, for example, Ci2-Cl8 _f: etta alcohol sulfates, which can be present individually or in a mixture, such as lauryl sulfate, myristy sulfate and here in particular Ci6-C ⁇ s tallow alcohol sulfate.
  • benzene sulfonates having 9 to 13 carbon atoms in the alkyl chain, in particular Ci2-alkylbenzene zolsulfonat r detergent-active salts of sulfonated fatty acid methyl esters-alpha and / or sodium soaps of fatty acids, especially fatty acids having 12 up to 18 carbon atoms.
  • the salts of long-chain ester carboxylic acids such as those obtainable from fatty alcohols having 8 to 18 carbon atoms and di- or polycarboxylic acids, for example maleic anhydride or citric acid, may also be suitable.
  • the anionic surfactants are preferably used in the form of the sodium salts.
  • the compounds used as solubilization aids according to the invention are polyethylene and / or polypropylene glycols or derivatives of these compounds.
  • the average molecular weight of these polymers is preferably in the range between about 200 and about 12000.
  • Polyethylene glycols with an average molecular weight between 600 and 4000 are particularly preferred.
  • the derivatives of the polyalkylene glycols which are suitable according to the invention are polymers which are anionic at one or both terminal hydroxyl groups are modified.
  • the sulfates and / or in particular the disulfates of the abovementioned polyalkylene glycols are suitable.
  • the sulfosuccinates and / or disulfosuccinates of these polyalkylene glycols are also suitable.
  • anionic derivatives are preferably derived from polyglycols with average molecular weights between 600 and 6000, in particular from those with average molecular weights between 1000 and 4000.
  • the anionic derivatives can be present as salts of any cations e, but are preferably used as alkali metal salts, especially as sodium or potassium salts, as well as salts of organic amines, for example triethanolamine.
  • Mixtures of the polyalkylene glycol ethers and their anionically modified derivatives are preferably also used in any mixing ratio.
  • a mixture of polyalkylene glycol and the sulfosuccinates and / or disulfosuccinates of the polyalkylene glycols is preferred.
  • a mixture of polyalkylene glycol and the corresponding sulfates and / or disulfates and a mixture of polyalkylene glycol, the corresponding sulfates and / or disulfates and the corresponding sulfosuccinates and / or disulfosuccinates are also suitable.
  • the proportion of the solubilization aid in the granulate is preferably 0.5 to 15% by weight, in particular 1 to 6% by weight.
  • mixtures of anionic surfactant and solubilizing auxiliaries are used as binders which are highly effective plastifying agents at the working temperature of the granulation, so that the desired plasticized good quality can be set even with limited amounts of the binder.
  • the amounts of binder are preferably below about 50% by weight of the total mixture, and the bleach activator is preferably present in this total mixture in amounts of about 70 to 95% by weight.
  • Particularly suitable activator contents can range from about 75 to 90% by weight on the entire granulate.
  • the rest of the granulate is formed by the binder or at least to a substantial extent by this surfactant binder.
  • the granules contain at least about 3% by weight, preferably at least about 5% by weight, of the binder mixture, based in each case on the entire granulate, binder amounts in the range from about 7 to 25% by weight being particularly preferred can.
  • Suitable bleach activators for per compounds are accordingly 0- and / or N-acylated compounds such as pentaacetylglucose (PAG), pentapropionylglucose (PPG), tetraacetylethylenediamine (TAED), tetraacetylglycoluril (TAGU), triacetylethanolamine (TAEA), acylated triazine derivatives such as 1,5-di-acetyl-2,4-dioxohexahydro-l, 3,5-triazine (DADHT), carboxylic anhydrides such as succinic, benzoic or phthalic anhydride, mixed salts Anhydrides, such as sodium or magnesium diacetyl phosphate (NADAP or MGDAP), phenol esters
  • the process according to the invention for producing the bleach activator granules is characterized in that the multicomponent mixture is first mixed as uniformly as possible in a suitable mixing device in the range of room temperature or only moderately elevated temperatures. All customary devices, for example of the Lödige ploughshare mixer type, are suitable as the mixing device. This premix is then fed to the stage of homogenization and extrusion. Although basically any homogenizing and extrusion devices - for example linear screw extruders - are suitable, a processing device has proven to be particularly suitable for carrying out the method according to the invention. This is the extrusion by means of a pellet press.
  • thermo-controlled roller pressing roller
  • the material temperature in the working space of the pellet press can be set to predetermined values, the aforementioned temperature range up to a maximum of 90 ° C. and preferably from 45 to 70 ° C. being selected here.
  • the cut granulate is subjected to shock cooling. Air or cooled air can be used as the cooling medium. Additionally or alternatively, the primarily extruded and cut granulate can be superficially loaded with very finely divided solids. Examples include powdered zeolites, especially detergent grade zeolite NaA, talc, silica and the like.
  • auxiliaries or additives may be desirable or expedient to incorporate further auxiliaries or additives into the granulate in addition to the finely divided solid bleach activators and the binder.
  • the proportion of these additives is preferably not more than 10% by weight, based on the granules.
  • Particularly noteworthy in this context are finely divided, readily soluble alkali salts of inorganic or organic acids.
  • the addition of these substances can in individual cases further accelerate the release of the activator when the granules are introduced into water.
  • Particularly suitable salts are sodium carbonate, sodium sulfate and sodium citrate.
  • the proportion of these salts in the granules is preferably not more than 10% by weight, based on the total weight of the granules, in particular it is between about 0.5% by weight and about 5% by weight.
  • additives which may be used are, for example, dyes as are customary in the detergent sector. To incorporate these substances, it may be expedient to suspend or dissolve them in liquid granulate components before they are mixed in.
  • Preferred dyes are pigment dyes, such as copper phthalocyanine dyes.
  • the amount of water should not be more than 1% by weight, preferably not more than 0.5% by weight, based on the total weight of the granules.
  • suitable auxiliaries are disintegrants and lubricants.
  • compression ratios can be set such that the finished granules have bulk densities of at least 500 g / l.
  • Bulk weights in the range up to 1000 g / l are particularly suitable here, bulk weights in the range 600 to 900 g / l being preferred.
  • Preferred granules are either cylindrical or spherical.
  • the additional rounding of the cylindrical shapes can expediently take place immediately after being cut to length on the still sufficiently warm granulate.
  • Auxiliary devices suitable for rounding off are known, for example the Marumerizers used for this purpose.
  • the grain size of the granules is regulated in a manner known per se and is expediently set in the range from 0.7 to 3 mm.
  • the granules can be cut to the desired grain length of 0.7 to 3 mm or beyond, for example to a grain length of 5 m.
  • These cylindrical granules with lengths above 3 mm are then broken to a predetermined length and rounded, if necessary, so that a length of 3 m is not exceeded.
  • Cylindrical granules preferably have a length of up to 2 mm, while additionally rounded, preferably spherical granules have a particle diameter in the range from 0.4 mm to 1.6 mm. Examples
  • the respective constituents were mixed intensively for one minute in a ploughshare mixer (Lödige, Germany) in the mixing ratios shown in the table.
  • the premix obtained in this way was then fed continuously to a ring die press (pellet press, embodiment according to DE 38 16 842, Schlüter, Germany), the temperature-controlled roller (press roll) of which was heated to 50.degree.
  • a ring die press pellet press, embodiment according to DE 38 16 842, Schlüter, Germany
  • the temperature of the press roll not dropping below 45 ° C. and not rising above 60 ° C.
  • the diameter of the press channels with which the ring die was penetrated was 1.2 mm.
  • the distance between the press roller and the ring die was 1.5 mm.
  • the emerging strand was cut to a length of 1.5 mm by a knife attached to the outside of the ring die.
  • the bulk weights of the granules were between 630 and 700 g / l.
  • the cut-to-length granules were then rounded off in a Marumerizer-type rounding machine.
  • the proportion of good grain (sieve fraction between 0.4 and 1.6 mm) of the granules decreased only slightly.

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  • Chemical & Material Sciences (AREA)
  • Inorganic Chemistry (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

Il est décrit un granulat se présentant sous la forme d'un produit en vrac, apte à l'écoulement, renfermant, comme constituant principal, des activateurs de blanchiment pour le lavage des textiles, intégrés, sous la forme d'une phase solide finement dispersée, dans une phase pratiquement anhydre, essentiellement constituée de matières solides, traversant le grain du granulat et servant de liant. Cette phase servant de liant est formée d'un mélange homogénéisé d'agents tensioactifs anioniques et d'auxiliaires de solubilisation qui sont adaptés, dans leur proportions, de telle façon que la phase mixte de liant se ramollisse pour devenir liquide ou plastique, à la température de travail de la formation du granulat, et ceci, même sans addition d'eau. Les granulats activateurs de blanchiment sont obtenus par mélange préalable des activateurs finement divisés avec les constituants du liant et, éventuellement, avec d'autres adjuvants, après quoi le mélange de produits est homogénéisé, à des températures de préférence modérément élevées, en une masse qui peut être comprimée en forme de boudin, puis extrudée sous pression élevée, les boudins sortants étant tronçonnés pour donner des grains ayant la forme voulue, et éventuellement arrondis.
PCT/EP1992/002909 1991-12-24 1992-12-15 Activateurs de blanchiment sous forme granulaire (ii) WO1993013194A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
DE59206759T DE59206759D1 (de) 1991-12-24 1992-12-15 Bleichaktivatoren in granulatform (ii)
KR1019940702218A KR940703910A (ko) 1991-12-24 1992-12-15 미립형의 표백 활성화제(ii) (bleach activators in granular form(ii))
JP5511402A JPH07502551A (ja) 1991-12-24 1992-12-15 顆粒状の漂白活性剤（■）
EP93901014A EP0618960B1 (fr) 1991-12-24 1992-12-15 Activateurs de blanchiment sous forme granulaire (ii)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4143016A DE4143016A1 (de) 1991-12-24 1991-12-24 Bleichaktivatoren in granulatform (ii)
DEP4143016.6 1991-12-24

Publications (1)

Publication Number Publication Date
WO1993013194A1 true WO1993013194A1 (fr) 1993-07-08

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ID=6448159

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1992/002909 WO1993013194A1 (fr) 1991-12-24 1992-12-15 Activateurs de blanchiment sous forme granulaire (ii)

Country Status (6)

Country Link
EP (1) EP0618960B1 (fr)
JP (1) JPH07502551A (fr)
KR (1) KR940703910A (fr)
DE (2) DE4143016A1 (fr)
ES (1) ES2089781T3 (fr)
WO (1) WO1993013194A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995017498A1 (fr) * 1993-12-23 1995-06-29 The Procter & Gamble Company Procede de fabrication d'un activateur de blanchiment au lactame contenant des particules
WO1996034081A1 (fr) * 1995-04-28 1996-10-31 Henkel Kommanditgesellschaft Auf Aktien Granulat stable au stockage contenant des activateurs de blanchiment et son mode de production
WO1997013834A1 (fr) * 1995-10-12 1997-04-17 Henkel Kommanditgesellschaft Auf Aktien Activateurs de blanchiment sous forme de granules (iii)
WO1997027280A1 (fr) * 1996-01-29 1997-07-31 The Procter & Gamble Company Procede de fabrication d'activateurs de blanchiment particulaires
WO2004027009A1 (fr) * 2002-09-12 2004-04-01 Henkel Kommanditgesellschaft Auf Aktien Produits de lavage ou de nettoyage comprimes sous l'effet d'une pression

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1301295A (zh) * 1998-03-19 2001-06-27 宝洁公司 含有流动性增强的圆柱形漂白活化剂挤出物的洗涤剂组合物
DE19959002C2 (de) * 1999-12-08 2002-12-05 Henkel Kgaa Verfahren zur Herstellung von verdichteten Teilchen
EG23339A (en) 1999-12-20 2004-12-29 Procter & Gamble Bleach activators with improved solubility.
DE10134364A1 (de) * 2001-07-14 2003-01-23 Clariant Gmbh Verfahren zur Herstellung von Bleichaktivator-Granulaten
DE10136805A1 (de) * 2001-07-25 2003-02-13 Clariant Gmbh Verfahren zur Herstellung von Bleichaktivator-Granulaten
DE102006041292A1 (de) * 2006-09-01 2008-03-06 Henkel Kgaa Wasserstoffperoxid-Aktivierung mit N-Heterocyclen
WO2022212865A1 (fr) 2021-04-01 2022-10-06 Sterilex, Llc Désinfectant/agent d'assainissement pulvérulents sans matière quaternaire

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2224509A1 (de) * 1972-05-19 1973-12-13 Henkel & Cie Gmbh Verfahren zur herstellung eines zur verwendung in wasch- und bleichmitteln geeigneten bleichhilfsmittel
EP0106634A1 (fr) * 1982-10-08 1984-04-25 THE PROCTER & GAMBLE COMPANY Masses contenant des activateurs de blanchiment
US4486327A (en) * 1983-12-22 1984-12-04 The Procter & Gamble Company Bodies containing stabilized bleach activators
GB2178075A (en) * 1985-07-19 1987-02-04 Colgate Palmolive Co Bleach active detergent additive composition
WO1991002047A1 (fr) * 1989-08-09 1991-02-21 Henkel Kommanditgesellschaft Auf Aktien Fabrication de granules comprimes pour produits de lavage
EP0456109A2 (fr) * 1990-05-10 1991-11-13 BASF Aktiengesellschaft Procédé pour préparer une composition granulaire d'activateur de blanchiment
WO1992002608A1 (fr) * 1990-08-03 1992-02-20 Henkel Kommanditgesellschaft Auf Aktien Activateurs du blanchiment sous forme de granules

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2224509A1 (de) * 1972-05-19 1973-12-13 Henkel & Cie Gmbh Verfahren zur herstellung eines zur verwendung in wasch- und bleichmitteln geeigneten bleichhilfsmittel
EP0106634A1 (fr) * 1982-10-08 1984-04-25 THE PROCTER & GAMBLE COMPANY Masses contenant des activateurs de blanchiment
US4486327A (en) * 1983-12-22 1984-12-04 The Procter & Gamble Company Bodies containing stabilized bleach activators
GB2178075A (en) * 1985-07-19 1987-02-04 Colgate Palmolive Co Bleach active detergent additive composition
WO1991002047A1 (fr) * 1989-08-09 1991-02-21 Henkel Kommanditgesellschaft Auf Aktien Fabrication de granules comprimes pour produits de lavage
EP0456109A2 (fr) * 1990-05-10 1991-11-13 BASF Aktiengesellschaft Procédé pour préparer une composition granulaire d'activateur de blanchiment
WO1992002608A1 (fr) * 1990-08-03 1992-02-20 Henkel Kommanditgesellschaft Auf Aktien Activateurs du blanchiment sous forme de granules

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1995017498A1 (fr) * 1993-12-23 1995-06-29 The Procter & Gamble Company Procede de fabrication d'un activateur de blanchiment au lactame contenant des particules
US5534196A (en) * 1993-12-23 1996-07-09 The Procter & Gamble Co. Process for making lactam bleach activator containing particles
WO1996034081A1 (fr) * 1995-04-28 1996-10-31 Henkel Kommanditgesellschaft Auf Aktien Granulat stable au stockage contenant des activateurs de blanchiment et son mode de production
WO1997013834A1 (fr) * 1995-10-12 1997-04-17 Henkel Kommanditgesellschaft Auf Aktien Activateurs de blanchiment sous forme de granules (iii)
WO1997027280A1 (fr) * 1996-01-29 1997-07-31 The Procter & Gamble Company Procede de fabrication d'activateurs de blanchiment particulaires
WO2004027009A1 (fr) * 2002-09-12 2004-04-01 Henkel Kommanditgesellschaft Auf Aktien Produits de lavage ou de nettoyage comprimes sous l'effet d'une pression

Also Published As

Publication number Publication date
DE4143016A1 (de) 1993-07-01
EP0618960A1 (fr) 1994-10-12
DE59206759D1 (de) 1996-08-14
KR940703910A (ko) 1994-12-12
EP0618960B1 (fr) 1996-07-10
ES2089781T3 (es) 1996-10-01
JPH07502551A (ja) 1995-03-16

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