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WO1995004810A1 - Procede de preparation de composes contenant de l'azote et exempts d'eau - Google Patents

Procede de preparation de composes contenant de l'azote et exempts d'eau Download PDF

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Publication number
WO1995004810A1
WO1995004810A1 PCT/EP1994/002574 EP9402574W WO9504810A1 WO 1995004810 A1 WO1995004810 A1 WO 1995004810A1 EP 9402574 W EP9402574 W EP 9402574W WO 9504810 A1 WO9504810 A1 WO 9504810A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkyl
fatty acid
carbon atoms
numbers
containing compounds
Prior art date
Application number
PCT/EP1994/002574
Other languages
German (de)
English (en)
Inventor
Bernd Fabry
Wilfried Rähse
Johann Friedrich Fues
Oriol Ponsati Obiols
Nuria Bonastre
Joaquim Bigorra Llosas
Ester Prat Queralt
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 JP7506214A priority Critical patent/JPH09501706A/ja
Priority to KR1019960700372A priority patent/KR960704021A/ko
Priority to EP94926144A priority patent/EP0712440A1/fr
Publication of WO1995004810A1 publication Critical patent/WO1995004810A1/fr

Links

Classifications

    • 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
    • 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
    • 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
    • A61Q5/12—Preparations containing hair conditioners
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D1/00—Evaporating
    • B01D1/16—Evaporating by spraying
    • B01D1/18—Evaporating by spraying to obtain dry solids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C07C209/82—Purification; Separation; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/10—Separation; Purification; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/22—Separation; Purification; Stabilisation; Use of additives
    • 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
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/528—Carboxylic amides (R1-CO-NR2R3), where at least one of the chains R1, R2 or R3 is interrupted by a functional group, e.g. a -NH-, -NR-, -CO-, or -CON- group
    • 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
    • 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
    • D06M13/402—Amides imides, sulfamic acids
    • 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
    • D06M13/46—Compounds containing quaternary nitrogen atoms
    • D06M13/463—Compounds containing quaternary nitrogen atoms derived from monoamines
    • 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
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • 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
    • D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/50—Modified hand or grip properties; Softening compositions

Definitions

  • the invention relates to a process for the preparation of anhydrous nitrogen-containing compounds with improved cold water solubility or dispersibility, in which aqueous or alcoholic solutions of quaternary ammonium compounds, ester quats or fatty acid amides are subjected to superheated steam drying, and the use of the dried material for the production of surface-active agents.
  • Quaternary ammonium compounds such as, for example, distaeryldimethylammonium chloride (DSDMAC) or increasingly quaternized fatty acid triethanolamine ester salts, so-called "esterquats", are generally suitable as active ingredients for this.
  • DMDMAC distaeryldimethylammonium chloride
  • esterquats increasingly quaternized fatty acid triethanolamine ester salts
  • US Pat. No. 2,340,881 describes aqueous dispersions of condensation products, prepared from a hydroxyalkyl polyamine and a fatty acid glyceride, which improve the lubricity and the softness of the textiles treated therewith.
  • the US 34 54 494 relates to fatty acid condensation products with an addition of dispersing polyglycol ethers.
  • the German patent DE-PS 19 22 046 describes detergents with a Content of fatty acid condensation products which contain fatty acid glycerides with a dispersing action; in the German patent DE-PS 19 22 047 these substances are also described as textile softeners for liquid laundry aftertreatment agents in particular.
  • the dispersibility of such substances can be increased by adding suitable dispersion accelerators, for example glucose, Improve sorbitol, mannitol, pentaerythritol, alkyl polyglucosides, sorbitan esters, gelatin and unsaturated fatty alcohols and fatty acids.
  • suitable dispersion accelerators for example glucose, Improve sorbitol, mannitol, pentaerythritol, alkyl polyglucosides, sorbitan esters, gelatin and unsaturated fatty alcohols and fatty acids.
  • ester quats with improved solubility or dispersibility in cold water are the skillful selection of the fatty acid component and the use of emulsifiers or dispersants (e.g. fatty alcohols or nonionic surfactants) as solvents instead of isopropyl alcohol in the alkoxylation and are the subject of previously unpublished patent applications .
  • emulsifiers or dispersants e.g. fatty alcohols or nonionic surfactants
  • nitrogen-containing compounds produced by the methods of the prior art cannot be dissolved or dispersed, or can only be insufficiently dispersed.
  • This uncertainty with regard to product quality represents a considerable economic disadvantage which limits the usability of the substances mentioned, for example as a sought-after textile treatment agent.
  • Another problem is that even those prior art products that have satisfactory solubility or dispersibility often lose irreversibly when stored in air.
  • the object of the invention was therefore to provide a new process for the preparation of anhydrous nitrogen-containing compounds with improved cold water solubility or dispersibility and storage stability, which is free from the disadvantages described.
  • the invention relates to a process for the preparation of anhydrous nitrogen-containing compounds having improved solubility or dispersibility in cold water, in which aqueous and / or alcoholic solutions or dispersions of quaternized ammonium compounds, esterquats or fatty acid amides are subjected to spray drying in the presence of superheated steam.
  • spray drying of the substances mentioned in the presence of superheated steam leads to a particularly advantageous grain structure which is free-flowing, low-dust and extremely water-soluble or water-dispersible.
  • comparable dry products that are manufactured using conventional processes are significantly exceeded in their properties.
  • drying can also be used to separate non-aqueous solvents without pluming and thus without any environmental pollution, since the process allows a completely closed procedure.
  • the invention also includes the knowledge that drying also deodorises and purifies the nitrogen-containing compounds, since disturbing contaminants which are volatile in water vapor, such as traces of unreacted alkylating agents, alkyl ethers and odor carriers, are removed virtually quantitatively.
  • the resulting dry material is very stable in storage and also meets the highest quality requirements, such as those desired for cosmetic products.
  • QAV Quaternized ammonium compounds
  • Suitable quaternized ammonium compounds are quaternized tetraalkylammonium salts of the formula (I)
  • R 1 and R 2 independently of one another are aliphatic alkyl radicals having 6 to 22 carbon atoms or benzyl radicals
  • R 3 is an alkyl or hydroxyalkyl radical having 1 to 4 carbon atoms
  • R 4 is a methyl group
  • X is halide, alkyl sulfate or alkyl phosphate.
  • the substances of the formula (I) are preferably classic cationic surfactants which have two fatty alkyl radicals having 6 to 22, preferably 16 to 18, carbon atoms and two methyl groups.
  • the most important example is distearyldimethylammonium chloride.
  • Substances of the formula (II) are suitable as quaternized fatty acid triethanolamine ester salts (esterquats),
  • R 5 CO represents an acyl radical having 6 to 22 carbon atoms
  • R 6 and R 7 independently of one another are hydrogen or R 1 CO
  • R 8 represents an alkyl radical having 1 to 4 carbon atoms or a (CH 2 CH 2 O) q H- Group
  • m, n and p in total stands for 0 or numbers from 1 to 12
  • X for halide, alkyl sulfate or alkyl phosphate.
  • ester quats examples include caproic acid, caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, isostearic acid, stearic acid, oleic acid, elaidic acid, arachic acid, behenic acid and erucic acid and their technical mixtures, such as those used in Pressure splitting of natural fats and oils occur.
  • Ester quats based on technical C 12/18 coconut fatty acids and in particular partially hardened C 16/18 tallow or palm fatty acids and C 16/18 fatty acid cuts rich in elaidic acid are preferably used and dried.
  • the fatty acids and the triethanolamine can be used in a molar ratio of 1.1: 1 to 3: 1 to produce the quaternized esters.
  • an application ratio of 1.2: 1 to 2.2: 1, preferably 1.5: 1 to 1.9: 1 has proven to be particularly advantageous.
  • the preferred esterquats are technical mixtures of mono-, di- and triesters with an average degree of esterification of 1.5 to 1.9 and are derived from technical C 16/18 tallow or palm fatty acid (iodine number 0 to 40).
  • Suitable fatty acid amides are compounds which follow the formula (III)
  • R 9 CO represents an aliphatic acyl radical with 8 to 22 carbon atoms and 0 and / or 1 to 3 double bonds
  • R 10 represents hydrogen, a methyl, ethyl, hydroxyethyl or a - (CH 2 ) n -NHR 11 - Group
  • R 11 for hydrogen, a methyl, Ethyl or hydroxyethyl group
  • x stands for numbers from 2 to 4 and y for numbers from 1 to 4.
  • fatty acid amides of the formula (III) in which R 9 is CO for a saturated and / or monounsaturated acyl radical having 16 to 18 carbon atoms, R 10 for a hydroxyethyl or
  • the fatty acids or their esters and the polyvalent amines can be used in a molar ratio of 1: 1 to 2.5: 1, preferably 1.3: 1 to 1.7: 1.
  • the components are heated over a period of 0.5 to 5, preferably 1 to 2 h to a temperature of 170 to 210, preferably 180 to 200 ° C. until the fatty acid or the fatty acid ester has been virtually completely reacted, and the mixture is then left to further React for 5 to 60, preferably 15 to 30, minutes at the reaction temperature.
  • a reducing agent e.g. B. hypophosphorous acid to perform.
  • the unreacted amino groups are neutralized with low molecular weight organic carboxylic acids, hydroxycarboxylic acids or inorganic acids, such as.
  • organic carboxylic acids such as acetic acid, lactic acid or phosphoric acid
  • acetic acid lactic acid or phosphoric acid
  • the acid used for salt formation can be used in amounts such as are required for 20 to 80, preferably 30 to 60, mol% neutralization.
  • superheated steam drying or “steam drying” is based on the principle that condensation of the superheated steam on the cooler feed and release of the heat of condensation to the material to be dried spontaneously heats the aqueous drop to the boiling point of the water under working conditions at normal pressure So at temperatures of about 100 ° C takes place. This boiling temperature is maintained as a minimum temperature in the droplet during the entire drying period.
  • a desired effect of the superheated steam drying of nitrogen-containing compounds can be seen in the fact that a dried material with a high inner surface is obtained which is particularly easy to dissolve or disperse in water.
  • the anhydrous nitrogen-containing compounds are obtained as low-dust, free-flowing powders with a bulk density of at least 150 g / l.
  • Drying with superheated steam can be carried out in the presence of further auxiliaries and additives, the amount used being 0.5 to 15, preferably 1 to 10% by weight, based on the solids content of the material to be dried.
  • Examples include dispersion accelerators such as addition products of an average of 1 mol of ethylene oxide and 2 mol of propylene oxide, 2 mol of ethylene oxide and 4 mol of propylene oxide, 5 mol of ethylene oxide and 1 mol of propylene oxide and 2 to 3 mol of propylene oxide with C 12/18 - coconut oil alcohol , C 16 / 18 - Taig fatty alcohol or C 16/18 palm fatty alcohol, monosaccharides of the aldose and ketose type, the polyhydroxy compounds derived therefrom by hydrogenation, pentaerythritol, trimethylolpropane, alkyl oligoglucosides, sorbitan esters, polysorbates as well as hydrophilic polymers based on carbohydrates or unsaturated alcohols or carboxylic acids.
  • dispersion accelerators such as addition products of an average of 1 mol of ethylene oxide and 2 mol of propylene oxide, 2 mol of ethylene oxide and 4 mol of propylene oxide, 5 mol of ethylene oxide
  • the anhydrous nitrogen-containing compounds obtainable by the process according to the invention are free-flowing, low-dust and outstandingly water-soluble or water-dispersible. They are suitable for the production of surface-active agents, in particular fabric softeners, hair and fiber conditioners and antistatic agents, in which they can be present in amounts of 1 to 75, preferably 3 to 50% by weight, based on the agent.
  • the product obtained had a dry matter content of 98.9% by weight and a bulk volume of 350 g / l.

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

Abstract

Pour obtenir des composés contenant de l'azote et exempts d'eau présentant une meilleure solubilité et une meilleure dispersibilité dans l'eau froide, on soumet à une opération de séchage par pulvérisation des solutions ou des dispersions aqueuses et/ou alcooliques de composés d'ammonium quaternaires, d'esters quaternaires ou d'amides d'acide gras en présence de vapeur d'eau surchauffée.
PCT/EP1994/002574 1993-08-11 1994-08-03 Procede de preparation de composes contenant de l'azote et exempts d'eau WO1995004810A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP7506214A JPH09501706A (ja) 1993-08-11 1994-08-03 水を含まない窒素含有化合物の製造方法
KR1019960700372A KR960704021A (ko) 1993-08-11 1994-08-03 무수 질소함유 화합물의 제조방법(process for preparing water-free nitrogenated compounds)
EP94926144A EP0712440A1 (fr) 1993-08-11 1994-08-03 Procede de preparation de composes contenant de l'azote et exempts d'eau

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4326975A DE4326975A1 (de) 1993-08-11 1993-08-11 Verfahren zur Herstellung von wasserfreien stickstoffhaltigen Verbindungen
DEP4326975.3 1993-08-11

Publications (1)

Publication Number Publication Date
WO1995004810A1 true WO1995004810A1 (fr) 1995-02-16

Family

ID=6494956

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1994/002574 WO1995004810A1 (fr) 1993-08-11 1994-08-03 Procede de preparation de composes contenant de l'azote et exempts d'eau

Country Status (6)

Country Link
EP (1) EP0712440A1 (fr)
JP (1) JPH09501706A (fr)
KR (1) KR960704021A (fr)
CN (1) CN1129012A (fr)
DE (1) DE4326975A1 (fr)
WO (1) WO1995004810A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE19515646A1 (de) * 1995-04-28 1996-10-31 Henkel Kgaa Avivagemittel

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2108420A5 (fr) * 1970-07-18 1972-05-19 Unilever Nv
DE4030688A1 (de) * 1990-09-28 1992-04-02 Henkel Kgaa Verfahren zur spruehtrocknung von wertstoffen und wertstoffgemischen unter verwendung von ueberhitztem wasserdampf
WO1992018685A1 (fr) * 1991-04-10 1992-10-29 Henkel Kommanditgesellschaft Auf Aktien Produit de traitement des textiles a dispersibilite amelioree dans l'eau
EP0547722A1 (fr) * 1991-12-18 1993-06-23 Colgate-Palmolive Company Composition adoucissante pour le linge sous forme de poudre s'écoulant librement et procédé pour sa fabrication
WO1993015812A1 (fr) * 1992-02-12 1993-08-19 Henkel Kommanditgesellschaft Auf Aktien Procede de fabrication de granulats convenant comme agents mouillants, detergents et/ou nettoyants
WO1994007978A1 (fr) * 1992-09-28 1994-04-14 Henkel Kommanditgesellschaft Auf Aktien Procede de fabrication de melanges de detergents se presentant sous forme de poudre ou de granules

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2108420A5 (fr) * 1970-07-18 1972-05-19 Unilever Nv
DE4030688A1 (de) * 1990-09-28 1992-04-02 Henkel Kgaa Verfahren zur spruehtrocknung von wertstoffen und wertstoffgemischen unter verwendung von ueberhitztem wasserdampf
WO1992018685A1 (fr) * 1991-04-10 1992-10-29 Henkel Kommanditgesellschaft Auf Aktien Produit de traitement des textiles a dispersibilite amelioree dans l'eau
EP0547722A1 (fr) * 1991-12-18 1993-06-23 Colgate-Palmolive Company Composition adoucissante pour le linge sous forme de poudre s'écoulant librement et procédé pour sa fabrication
WO1993015812A1 (fr) * 1992-02-12 1993-08-19 Henkel Kommanditgesellschaft Auf Aktien Procede de fabrication de granulats convenant comme agents mouillants, detergents et/ou nettoyants
WO1994007978A1 (fr) * 1992-09-28 1994-04-14 Henkel Kommanditgesellschaft Auf Aktien Procede de fabrication de melanges de detergents se presentant sous forme de poudre ou de granules

Also Published As

Publication number Publication date
KR960704021A (ko) 1996-08-31
CN1129012A (zh) 1996-08-14
EP0712440A1 (fr) 1996-05-22
JPH09501706A (ja) 1997-02-18
DE4326975A1 (de) 1995-02-16

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