EP0663003A1 - Procede de fabrication de melanges de detergents se presentant sous forme de poudre ou de granules - Google Patents

Procede de fabrication de melanges de detergents se presentant sous forme de poudre ou de granules

Info

Publication number
EP0663003A1
EP0663003A1 EP93920769A EP93920769A EP0663003A1 EP 0663003 A1 EP0663003 A1 EP 0663003A1 EP 93920769 A EP93920769 A EP 93920769A EP 93920769 A EP93920769 A EP 93920769A EP 0663003 A1 EP0663003 A1 EP 0663003A1
Authority
EP
European Patent Office
Prior art keywords
acid
carbon atoms
formula
mixtures
fatty
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.)
Withdrawn
Application number
EP93920769A
Other languages
German (de)
English (en)
Inventor
Oriol Ponsati Obiols
Nuria Bonastre
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
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 AG and Co KGaA filed Critical Henkel AG and Co KGaA
Publication of EP0663003A1 publication Critical patent/EP0663003A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2003—Alcohols; Phenols
    • C11D3/2006—Monohydric alcohols
    • C11D3/201—Monohydric alcohols linear
    • C11D3/2013—Monohydric alcohols linear fatty or with at least 8 carbon atoms in the alkyl chain
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/0216—Solid or semisolid forms
    • A61K8/022—Powders; Compacted Powders
    • A61K8/0225—Granulated powders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/39—Derivatives containing from 2 to 10 oxyalkylene groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/416—Quaternary ammonium compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/45—Derivatives containing from 2 to 10 oxyalkylene groups
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • 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
    • C11D1/66—Non-ionic compounds
    • C11D1/835—Mixtures of non-ionic with cationic 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
    • C11D11/00—Special methods for preparing compositions containing mixtures of detergents
    • C11D11/02—Preparation in the form of powder by spray drying
    • 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
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/06—Powder; Flakes; Free-flowing mixtures; Sheets
    • 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
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/22—Carbohydrates or derivatives thereof
    • C11D3/221—Mono, di- or trisaccharides or derivatives thereof
    • 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
    • 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
    • C11D1/66—Non-ionic compounds
    • C11D1/662—Carbohydrates or derivatives
    • 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
    • C11D1/66—Non-ionic compounds
    • C11D1/667—Neutral esters, e.g. sorbitan esters
    • 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
    • C11D1/66—Non-ionic compounds
    • C11D1/72—Ethers of polyoxyalkylene glycols

Definitions

  • the invention relates to a process for the production of powdery or granular detergent mixtures, in which mixtures of quaternized difatty acid trialkanolamine ester salts and hydroxy compounds are dried in a manner known per se and brought into solid form.
  • German patent DE 19 22 046 relates to detergents containing fatty acid condensation products which contain fatty acid glycerides with a dispersing action; In the German patent DE 19 22 047 these substances are also described as textile softeners for liquid laundry aftertreatment agents in particular. These and similar agents can be dispersed in water by placing them in hot water and usually applying high shear forces, or by dispersing the condensation product, which has still been melted, in water. Because of the effort required, the manufacturer therefore usually carries out the dispersion and supplies the user with the dispersions, which is associated with the storage and transport of considerable amounts of water and is therefore not economically viable.
  • the cold water dispersibility of the cationic surfactants mentioned can also be improved, but this advantage will however, often overcompensated by the fact that the mixtures of cationic surfactant and dispersant have comparatively poorer application properties. Notwithstanding this decisive disadvantage, the mixtures of the prior art can also be processed to low-water concentrates, but in the production of powders or granules the advantage of improved cold water dispersibility that has just been obtained is often lost again.
  • the object of the invention was therefore to develop a new process for the production of powdery or granular detergent mixtures, by means of which products with good conditioning properties and satisfactory cold water dispersibility can be made available.
  • the invention relates to a process for the preparation of powdery or granular detergent mixtures, in which mixtures containing
  • R ⁇ -CO represents an aliphatic acyl radical having 12 to 22 carbon atoms and 0, 1, 2 or 3 double bonds, n represents 2 or 3 and X represents halide, methosulphate or methophosphate and
  • hydroxy compounds selected from the group formed by fatty alcohols, fatty alcohol polyglycol ethers, partial polyol fatty acid esters and carbohydrates,
  • the cold water dispersibility of quaternized difatty acid trialkanolamine ester salts can be significantly improved by addition of the hydroxy compounds mentioned, without the application properties of the products being adversely affected by this measure.
  • the invention includes the knowledge that low-water concentrates of these mixtures can be processed into powders or granules without any problems and that the resulting solids in turn also have satisfactory dispersibility in cold water.
  • Quaternized difatty acid trialkanolamine ester salts are known cationic surfactants which can be obtained by the relevant methods of preparative organic chemistry.
  • a process for their preparation consists, for example, in reacting fatty acids with triethanolamine in the presence of reducing agents and with passage of air and then quaternizing the diester with dimethyl sulfate or methyl chloride [WO 91/01295, Henkel]. Since these are technical products, quaternized mono- and triesters are always contained as by-products in the ester quats.
  • Typical examples of the fatty acid components of these compounds are caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, arachic acid, gadoleic acid, behenic acid, and technical acid and mixtures, erucic acid as they occur, for example, in the splitting of vegetable oils or animal fats.
  • Quaternized difatty acid trialkanolamine ester salts of the formula (I) are preferably used in which R 1 CO is an aliphatic acyl radical having 16 to 18 carbon atoms, n is 2 and X is methosulfate or chloride. Esterquats based on stearic acid, tallow fatty acid or technical grade elaidic acid are particularly preferred.
  • Hydroxy compounds of the following type are suitable as dispersants:
  • R2 represents an optionally hydroxy-substituted alkyl and / or alkenyl radical having 12 to 22 carbon atoms.
  • Typical examples are lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, isostearyl alcohol, oleyl alcohol, elaidyl alcohol, petroselinyl alcohol, linolyl alcohol, linolenyl alcohol, ricinolyl alcohol, 12-hydroxystearyl alcohol, arachyl alcohol, Gadoleyl alcohol, behenyl alcohol and erucyl alcohol and their technical mixtures, such as those obtained in the hydrogenation of technical fatty acid methyl ester fractions or aldehydes from Roelen's oxosynthesis.
  • Technical C12 / I8 coconut fatty alcohol or Ci2 / 18 ⁇ Ta l9f etta lk ° ° l are preferably used.
  • R3 represents an optionally hydroxy-substituted alkyl and / or alkenyl radical having 12 to 22 carbon atoms
  • R ⁇ represents hydrogen or a methyl group
  • m represents numbers from 1 to 40.
  • Typical examples are addition products of 1 to 40, preferably 10 to 25, moles of ethylene and / or propylene oxide onto the alcohols mentioned under a).
  • Addition products of an average of 10 to 25 moles of ethylene oxide with fatty alcohols having 16 to 18 carbon atoms, which may have a conventional or narrow homolog distribution, are preferably used.
  • partial polyol fatty acid esters this includes mono- and / or diesters of polyols with fatty acids of the formula (IV),
  • Typical examples are mono- and / or diesters of caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, palmoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, arachidic acid, gadoleic acid, behenic acid and erucic acid and erucic acid and erucic acid and erucic acid and erucic acid and erucic acid and erucic acid and erucic acid and erucic acid technical mixtures with polyols selected from the group formed by glycerol, diglycerol, triglycerol, trimethylolpropane, pentaeryth
  • d) carbohydrates typical examples are glucose and in particular sorbitol.
  • the quaternized difatty acid trialkanola inester salts and the hydroxy compounds can be used in a weight ratio of 1.5: 1 to 2.0: 1. Products with particularly good water dispersibility and excellent leveling properties are obtained if a weight ratio of 1.6: 1 to 1.9: 1 is set between the components.
  • mixtures of hydroxy compounds which have a sorbitol content of 1 to 10, preferably 2 to 5% by weight, based on the mixture of the hydroxy compounds.
  • the mixing of the components is a purely mechanical process; a chemical reaction does not take place.
  • the water content of the mixtures is largely uncritical for the production of the powders or granules.
  • the more or less water-containing detergent mixtures can be converted into solid forms by methods known per se.
  • One possibility is to subject the mixtures to spray drying, as is known for the production of powder detergents.
  • spray drying as is known for the production of powder detergents.
  • a variant of this process for the particularly gentle production of powdered detergent compositions is water vapor drying.
  • the detergent mixtures can be spray dried at normal pressure using superheated steam as a hot gas stream. In this way, powders are obtained, the grain of which is distinguished by a particularly high surface area and therefore slight water solubility.
  • German patent application DE-Al 40 30 688 Heenkel.
  • the detergent mixtures can also be provided in the form of granules, for example flakes. The granulation can - if appropriate in the presence of solid carriers such as zeolites or inorganic salts - z. B. in an extruder, a high-speed mixer or a roller granulator.
  • the detergent mixtures can also contain further ingredients typical of detergents and cleaning agents, such as. B. contain builders or actuators.
  • the residual water content in the spray-dried or steam-dried products is practically zero; in products which have been produced by granulation, it can be up to 20, preferably up to 15% by weight, based on the mixtures.
  • the powdery or granular detergent mixtures obtainable by the process according to the invention are notable for good cold water dispersibility and excellent softening properties in relation to the feel of fibers and textiles and the wet and dry combability of hair.
  • Another object of the invention therefore relates to the use of the detergent mixtures for the production of conditioners and fabric softeners and hair care products, such as, for example, hair shampoos or hair rinses, in which they are used in amounts of 1 to 50, preferably 10 to 30,% by weight moved to the means - may be included.
  • conditioners and fabric softeners and hair care products such as, for example, hair shampoos or hair rinses, in which they are used in amounts of 1 to 50, preferably 10 to 30,% by weight moved to the means - may be included.
  • detergent mixtures were produced, which were processed in a high-speed mixer into granules with a residual water content of 15% by weight.
  • dispersions of the granules in water (16 ° C., 20 ° C.) were prepared and stirred at a speed of 500 rpm until a homogeneous distribution was achieved.
  • the dispersions were stored at 20 ° C. and their stability was assessed over a period of 14 days.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Wood Science & Technology (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Veterinary Medicine (AREA)
  • Organic Chemistry (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Emergency Medicine (AREA)
  • Molecular Biology (AREA)
  • Detergent Compositions (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

Pour obtenir des mélanges de détergents présentant une bonne dispersibilité à l'eau froide, sous forme de poudre ou de granulés, on utilise des mélanges contenant a) des sels quaternaires d'esters de trialkamyne de diacide gras de la formule (I) dans laquelle R1CO désigne un reste acyle aliphatique ayant 12 à 22 atomes de carbone et 0, 1, 2 ou 3 liaisons doubles, n vaut 2 ou 3 et X désigne hydrocarbure halogéné, méthosulfate ou méthophosphate et b) des composés hydroxy, choisis dans le groupe constitué par les alcools gras, les polyglycoléthers d'alcool gras, les esters partiels d'acide gras de polyol et d'hydrates de carbone. On sèche et on solidifie lesdits mélanges, selon des procédés connus. Ces produits conviennent à la fabrication d'agents d'avivage, de produits de rinçage assouplissants pour le linge et de produits de soins capillaires.
EP93920769A 1992-09-28 1993-09-20 Procede de fabrication de melanges de detergents se presentant sous forme de poudre ou de granules Withdrawn EP0663003A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19924232448 DE4232448A1 (de) 1992-09-28 1992-09-28 Verfahren zur Herstellung pulverförmiger oder granularer Detergensgemische
DE4232448 1992-09-28
PCT/EP1993/002536 WO1994007978A1 (fr) 1992-09-28 1993-09-20 Procede de fabrication de melanges de detergents se presentant sous forme de poudre ou de granules

Publications (1)

Publication Number Publication Date
EP0663003A1 true EP0663003A1 (fr) 1995-07-19

Family

ID=6469015

Family Applications (1)

Application Number Title Priority Date Filing Date
EP93920769A Withdrawn EP0663003A1 (fr) 1992-09-28 1993-09-20 Procede de fabrication de melanges de detergents se presentant sous forme de poudre ou de granules

Country Status (3)

Country Link
EP (1) EP0663003A1 (fr)
DE (1) DE4232448A1 (fr)
WO (1) WO1994007978A1 (fr)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4326975A1 (de) * 1993-08-11 1995-02-16 Henkel Kgaa Verfahren zur Herstellung von wasserfreien stickstoffhaltigen Verbindungen
GB9319566D0 (en) * 1993-09-22 1993-11-10 Unilever Plc Rinse conditioner
DE4400927A1 (de) * 1994-01-14 1995-07-20 Henkel Kgaa Wäßrige Lösungen von quaternierten Fettsäuretriethanolaminester-Salze
DE4430721A1 (de) * 1994-08-30 1996-03-07 Hoechst Ag Autoglanztrocknungsmittel
DE4437032A1 (de) * 1994-10-17 1996-04-18 Henkel Kgaa Textile Weichmacher-Konzentrate
DE4439076A1 (de) * 1994-11-02 1996-05-09 Henkel Kgaa Avivagemittel mit verbessertem Wiederbenetzungsvermögen
DE19732015C1 (de) * 1997-07-25 1998-07-23 Henkel Kgaa Selbstemulgierende Zubereitungen
US6002932A (en) * 1997-11-26 1999-12-14 Ericsson Inc. System and method for mobile terminal positioning
DE19810122C2 (de) * 1998-03-09 2000-04-06 Goldwell Gmbh Haarbehandlungsmittel
CN1182232C (zh) * 1998-07-27 2004-12-29 Lg化学株式会社 分子中含有酯基的阳离子表面活性剂的制备
KR100696704B1 (ko) * 2000-12-08 2007-03-20 주식회사 엘지생활건강 분자 내에 에스테르기를 갖는 양이온성 계면활성제의 제조 방법
US6984618B2 (en) 2001-12-05 2006-01-10 The Procter & Gamble Company Softening-through-the wash composition
GB0207484D0 (en) 2002-03-28 2002-05-08 Unilever Plc Solid fabric conditioning compositions
ES2596325T3 (es) 2002-12-04 2017-01-05 Clariant International Ltd Composición de amonio cuaternario
KR101894960B1 (ko) 2015-06-26 2018-09-05 에이케이켐텍 주식회사 생분해성 지방산계 계면활성제의 제조방법

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0021491A1 (fr) * 1979-06-18 1981-01-07 THE PROCTER & GAMBLE COMPANY Composition détergente contenant un mélange non-ionique et cationique d'agents tensioactifs et un mélange d'agents renforçateurs
DE3720332A1 (de) * 1987-06-19 1988-12-29 Huels Chemische Werke Ag Verfahren zur herstellung von trialkanolamindifettsaeureestern und deren verwendung
JPH02139480A (ja) * 1988-11-21 1990-05-29 Kao Corp 柔軟仕上剤
AU4712189A (en) * 1989-01-03 1990-07-12 Amway Corporation Nonionic laundry detergent composition
DE4138630A1 (de) * 1991-11-25 1993-05-27 Henkel Kgaa Saure haarpflegemittel
US5259964A (en) * 1991-12-18 1993-11-09 Colgate-Palmolive Co. Free-flowing powder fabric softening composition and process for its manufacture

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9407978A1 *

Also Published As

Publication number Publication date
WO1994007978A1 (fr) 1994-04-14
DE4232448A1 (de) 1994-03-31

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