EP1115822B1 - Verwendung von kationischen materialien und zusammensetzungen - Google Patents

Verwendung von kationischen materialien und zusammensetzungen Download PDF

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Publication number
EP1115822B1
EP1115822B1 EP99950531A EP99950531A EP1115822B1 EP 1115822 B1 EP1115822 B1 EP 1115822B1 EP 99950531 A EP99950531 A EP 99950531A EP 99950531 A EP99950531 A EP 99950531A EP 1115822 B1 EP1115822 B1 EP 1115822B1
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Prior art keywords
fabric
cationic
use according
cationic material
residues
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French (fr)
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EP1115822A1 (de
Inventor
Keri Unilever Research Port Sunlight Futter
Gillian Unilever Research Port Sunlight MCHATTIE
Philip John Unilever Research Port Sunlight SAMS
Christopher Unilever Resear.Port Sunlight WHALEY
Michael Unilever Research Colworth York
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Unilever PLC
Unilever NV
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Unilever NV
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    • 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
    • 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

  • This invention relates to the use of cationic materials and compositions, in particular cationic fabric conditioning materials and compositions, to reduce skin irritancy. It also relates to a fabric laundering process which includes such use.
  • Detergents used to launder fabrics can leave residues, e.g. anionic materials, on the fabrics after the wash. If left untreated, or unremoved, these residues can cause undesirable effects when the fabric is subsequently worn.
  • fabric conditioning compositions many of which contain cationic materials, may be used in the post-wash rinsing or drying stage of a fabric laundering process, to soften fabrics and make them generally more comfortable to wear next to the skin.
  • GB 2039556 (Unilever) discloses a fabric conditioning composition comprising two or more cationic compounds which render the composition less sensitive to anionic carryover.
  • JP 7018571 (Lion Corporation) teaches an acid-neutralised amine compound which imparts flexibility to clothing in the presence of carried-over anionic surfactant.
  • EP 0323395 Cold-Palmolive discloses that anionic residues on washed fabrics can be reduced using selected nonionic rinse formulations.
  • the present invention seeks to address the above-identified problems.
  • cationic materials in particular cationic fabric conditioning materials, can reduce skin irritancy caused by anionic materials present on fabric after laundering.
  • the present invention provides the use of a cationic material to reduce skin irritancy of a material extractable from a fabric using water or an aqueous solution, as defined in claim 1.
  • 'use' is defined as the application of the cationic material to, and/or its contact with, the fabric.
  • 'Skin irritancy' is defined as the ability of a material to react chemically with (human) skin to cause a local inflammatory response following a single, repeated or continuous contact.
  • the irritant response may be characterised by symptoms such as erythema, oedema and/or skin dryness.
  • the cationic material may neutralise free anionic residues on washed fabrics (such as by forming chemical complexes with them) and can prevent, or at least hinder, the subsequent release of the residues from the fabrics.
  • the invention provides the use of the cationic material to reduce skin irritancy of a material extractable from a fabric using water or an aqueous solution in which the cationic material neutralises free anionic residues on washed fabrics.
  • extractable residues i.e., residues which can be extracted from a fabric by contact with water or an aqueous solution, for instance by contact with the wearer's sweat.
  • cationic materials can form chemical complexes with the free anionic residues. This can serve to reduce the extractability of the residues (the complexed residues being less likely to be soluble in water).
  • the invention provides the use of the cationic material to reduce skin irritancy of a material extractable from a fabric using water or an aqueous solution in which the cationic material forms chemical complexes with free anionic residues on a fabric.
  • cationic material may serve to reduce the extractability of the residues, i.e. prevent, or at least hinder, the subsequent release of the residues from the fabrics.
  • the invention provides the use of the cationic material to reduce skin irritancy of a material extractable from a fabric using water or an aqueous solution in which the cationic material prevents or at least hinders the subsequent release of free anionic residues from a fabric.
  • the mechanism for reducing irritancy which preferably involves interaction (e.g. complexation) of the cationic material with the anionic residues, is different from the mechanism of softening, which involves depositing a softening compound onto the fabric in a way which provides a lubricating layer between fabric and skin.
  • the phrase 'cationic material' encompasses a single cationic material as well as a mixture of two or more cationic materials.
  • the cationic material is preferably a cationic surfactant, more preferably a cationic surfactant having fabric conditioning, such as fabric softening, properties.
  • Suitable cationic surfactants for use in the present invention are known in the art - see in particular Schwartz, Perry and Berch, 'Surface Active Agents' (Volumes I and II); Davidson and Milwidsky, 'Synthetic Detergents', John Wiley & Sons; and 'Household Industrial Fabric Conditioners' (Noyes Data Corporation).
  • quaternary ammonium materials which comprise a polar head group and one or two alkyl or alkenyl chains.
  • the average chain length is at least C 14 , and more preferred that each chain has an average chain length of or greater than C 16 . More preferably still, at least 50% of the long chain alkyl or alkenyl groups have a chain length of C 18 or more.
  • long chain alkyl or alkenyl groups be predominantly linear.
  • Well known quaternary ammonium compounds of use in the invention include those having the formula: R 1 R 2 R 3 R 4 N + X - wherein R 1 and R 2 represent hydrocarbyl groups having from 12 to 24 carbon atoms; R 3 and R 4 represent hydrocarbyl groups containing from 1 to 4 carbon atoms; and X - is an anion, preferably a halide, methyl sulphate or ethyl sulphate anion.
  • quaternary ammonium materials having two long chain alkyl or alkenyl groups include di (tallow alkyl) dimethyl ammonium chloride; di(tallow alkyl) dimethyl ammonium methyl sulphate; dihexadecyl dimethyl ammonium chloride; di(hydrogenated tallow alkyl) dimethyl ammonium chloride (such as Arquad 2HT (trade mark)); di(hydrogenated tallow alkyl) dimethyl ammonium methyl sulphate; dioctadecyl dimethyl ammonium chloride; dihexadecyl diethyl ammonium chloride; and di(coconut alkyl) dimethyl ammonium chloride.
  • the cationic surfactant could alternatively be a quaternary ammonium material of a single long chain type, preferably having the formula: (R) 3 N + R 5 X - wherein each R group is independently selected from H or C 1- C 4 alkyl or hydroxyalkyl groups, R 5 is a C 8 -C 22 alkyl or alkenyl group, optionally interrupted by ester, amide, ether or amine functionality, and X - is as defined above.
  • Preferred compounds of this type are linear C 12 -C 18 alkyl or alkenyl trimethyl ammonium chlorides and choline esters of C 12 -C 18 fatty acids.
  • cationic surfactants contain esters or amide links, for example, those available under the trade names Accosoft 580, Varisoft 2202 and Stepantex.
  • the double long chain cationic materials of this type can be partially unsaturated (for instance tallow-derived materials like di(tallowoyloxyethyl) dimethyl ammonium chloride) or can contain long alkyl chains in the C 10 -C 18 range (e.g., di(cocoyloxyethyl) dimethyl ammonium chloride).
  • Particularly preferred cationic materials are quaternary ammonium materials having two C 12 -C 18 alkyl or alkenyl groups connected to the molecule via at least one ester link. It is more preferred if the material contains two ester links.
  • a preferred ester-linked quaternary ammonium material for use in the present invention is represented by the general formula: wherein each R 6 group is independently selected from C 1 -C 4 alkyl or hydroxyalkyl or C 2 -C 4 alkenyl groups; each R 7 group is independently selected from C 1 -C 4 straight- or branched-chain alkylene groups; each R 8 group is independently selected from C 8 -C 28 , preferably C 12 -C 18 , alkyl or alkenyl groups; and X - is as defined above.
  • a particularly preferred material of this class is the fabric softener di-[2-(tallowoyloxy)ethyl] dimethyl ammonium chloride and its hardened tallow analogue (see DE-1,619,058).
  • ester-containing quaternary ammonium material is represented by the formula: wherein R 6 , R 8 and X - are as defined above, and n is an integer from 0 to 5.
  • Preferred materials of this class such as 1,2 -bis- [tallowoyloxy]-3-trimethyl ammonium propane chloride or 1,2-bis-[hardened tallowoyloxy]-3-trimethyl ammonium propane chloride, are described for example in US-4,137,180, as is their method of preparation.
  • these materials include small amounts of the corresponding monoester, as also described in US-4,137,180, for example 1-tallowoyloxy-2-hydroxy trimethylammonium propane chloride.
  • Preferred cationic fabric softening compounds are substantially water insoluble.
  • Substantially water insoluble' surfactant compounds in the context of this invention are defined as compounds having a solubility less than 1 x 10 -3 wt% in demineralised water at 20°C.
  • the cationic surfactants have a solubility less than 1 x 10 -4 .
  • the cationic surfactants have a solubility at 20°C in demineralised water from 1 x 10 -8 to 1 x 10 -6 wt%.
  • the cationic material used in the present invention is biologically degradable.
  • the cationic material may be a polycationic oligomer, polymer or co-polymer, which materials have been found to be particularly effective at neutralising free anionic residues. Such materials may be either synthetically or naturally derived.
  • Cationic monomers which are suitable for inclusion in 'addition' polymers or, co-polymers include diallyldimethylammonium chloride and quaternised 2-(N,N-dimethylamino)ethyl methacrylate.
  • Other suitable cationic polymers include poly(ethylene imine) and derivatives thereof.
  • Such polycationic materials are preferably used together with one or more cationic surfactant(s), more preferably with one or more cationic fabric softening surfactant(s).
  • the cationic material can be included in a variety of fabric treatment compositions and products, of which the following are examples.
  • the cationic material may be used in a cationic fabric conditioning composition (such as a rinse conditioning composition).
  • a 'cationic fabric conditioning composition' is defined as one which contains at least one cationic fabric conditioning material.
  • the cationic material is used in the form of an aqueous dispersion, which may contain other materials with which the fabric is to be simultaneously treated.
  • the cationic fabric conditioning composition should be easily dispensable and easily dispersible in an aqueous rinse bath, and its viscosity is therefore preferably less than 300 mPa.s at 21 s -1 , more preferably less than 200 mPa.s at 21 s -1 .
  • the composition should preferably not have too low a viscosity - for instance no lower than 50 mPa.s at 21 s -1 , more preferably no lower than 100 mPa.s at 21 s -1 . (The viscosities quoted are measured at 20°C using a Haake RV20 rotoviscometer or similar equipment.)
  • the cationic material can be used in a fabric laundering process, preferably a domestic laundering process, during which it is conveniently contacted with a laundered fabric during a post-wash rinse.
  • the rinse may follow directly on from a machine or hand wash, or, it may be a separate fabric rinse which may even take place after the fabric has been both washed and dried.
  • composition's active fabric conditioning ingredients are cationic.
  • the cationic material may be applied directly to a fabric at any time, for instance by spraying or dipping, to reduce skin irritancy of material extractable from the fabric. It may be applied to a newly manufactured or treated fabric as part of a fabric finishing treatment. It may also be applied, for instance in the form of an aerosol spray, during ironing of a fabric.
  • the cationic material can be used in a fabric treatment composition (such as a spray or a dip), in order to reduce skin irritancy of material extractable from a fabric.
  • a fabric treatment composition such as a spray or a dip
  • the composition may include other materials with which the fabric is to be treated.
  • the cationic material may be contained in an automatic laundry dryer product, such as a product for use in a tumble dryer.
  • a suitable substrate such as a porous sheet or a sponge, may be impregnated with or coated with the cationic material, in a manner which allows the release of the material from the substrate during its use in an automatic dryer.
  • Tumble dryer sheets for instance, may be made of any suitable flexible material such as paper or a woven or non-woven cloth.
  • Such tumble dryer products can be designed for single or multiple use, a multiple use product comprising for instance a sponge substrate which releasably carries sufficient cationic material to impart the desired effect during several consecutive drying cycles.
  • the cationic material may, for instance, melt and leach out of the sponge during drying, thereby coming into contact with the fabric(s) being dried.
  • compositions and products in which the cationic material is included may also contain optional ingredients.
  • the fabric conditioning compositions may include other fabric conditioning materials such as nonionic fabric conditioners.
  • Preferred nonionic fabric conditioners include CPEs (cyclic polyols in which 4 or more of the hydroxyl groups are esterified and/or etherified and in which at least two or more of these ester or ether groups are independently of one another attached to a C 8 to C 22 alkyl or alkenyl chain) and RSEs (reduced saccharide in which 4 or more hydroxyl groups are esterified and/or etherified and in which at least two or more of these ester or ether groups are independently of one another attached to a C 8 to C 22 alkyl or alkenyl chain).
  • CPEs cyclic polyols in which 4 or more of the hydroxyl groups are esterified and/or etherified and in which at least two or more of these ester or ether groups are independently of one another attached to a C 8 to C 22 alkyl or alkenyl chain
  • RSEs reduced saccharide in which 4 or more hydroxyl groups are esterified and/or etherified and in which at
  • the C 8 to C 22 alkyl or alkenyl groups may be branched or linear carbon chains.
  • Examples of preferred cyclic polyols from which CPEs are derived include Inositol and all forms of saccharides.
  • Examples of preferred saccharides are monosaccharides and disaccharides.
  • Examples of monosaccharides include xylose, arabinose, galactose, fructose, sorbose and glucose.
  • Examples of disaccharides include maltose, lactose, cellobiose and sucrose.
  • An example of a reduced saccharide includes sorbitan.
  • CPEs examples include sucrose octaoleate, esters of alkyl(poly)glucosides, in particular alkyl glucoside esters having a degree of polymerisation from 1 to 2.
  • suitable saccharides esters include fatty acid esters of glucose, the ester groups comprising C 2 -C 18 alkyl or alkenyl chain and the degree of esterification being 5 and in particular saccharides having ester groups consisting essentially of a C 2 alkyl chain and a C 8 to C 12 straight alkyl chain, the molar ratio of short chain C 2 alkyl chains to C 8 to C 12 straight alkyl chains being from 2:1 to 1:2, more preferably about 1:1.
  • Materials which enhance deposition of the conditioning material(s) onto fabrics may also usefully be included in the composition.
  • Such materials are often polymeric; GB-2,266,100 for instance discloses certain cellulose ethers for this purpose, and also mentions earlier documents which proposed materials able to bring about or enhance deposition.
  • aqueous compositions containing a dispersion of the relevant fabric conditioning material(s) include pH buffering agents, perfumes, perfume carriers, fluorescers, colourants, hydrotropes, antifoaming agents, antiredeposition agents, polyelectrolytes, enzymes, optical brightening agents, anti-shrinking agents, anti-wrinkle agents, anti-spotting agents, germicides, fungicides, anti-corrosion agents, drape imparting agents, anti-static agents, ironing aids, dyes, fatty acids and polymeric thickeners.
  • cationic material For tumble dryer sheets and the like, other conventional ingredients which may be carried on the substrate with the cationic material include other fabric conditioning materials, perfumes, perfume carriers, drape imparting agents, anti-static agents, ironing aids and deposition aids.
  • the fabric on which the cationic material or cationic fabric conditioning composition is used will typically be an item of clothing, in particular a garment intended to be worn next to the skin, such as an item of underwear or a t-shirt.
  • the present invention may be used to reduce skin irritancy caused by many different types of anionic residues, especially detergents, which may be present on a fabric usually after washing.
  • Anionic surfactant residues which may, for instance, be treated using the invention include sulphonates, in particular alkyl-aryl sulphonates such as alkyl benzene sulphonates, alkane sulphonates, olefin sulphonates, fatty acid ester sulphonates, sulpho-carboxylates, isethionates, sulphosuccinates and taurates; sulphates, in particular primary and secondary alkyl sulphates, alkyl ether sulphates and alkyl phenol ether sulphates; carboxylates, in particular simple soaps such as sodium or potassium soaps, ethoxy carboxylates, phenol ethoxy carboxylates, sarcosinates, succinates and other multi-carboxy
  • the residues which are treated using the present invention are preferably those which are relatively water soluble, for instance having a solubility of at least 1% wt/wt in water at 20°C (which includes material existing in a micellar state in the solution).
  • the amount of free anionic residues on a fabric is reduced by at least 50%, more preferably by at least 75%, by the use of the cationic material to treat the fabric.
  • the amount of cationic material used should preferably be at least, more preferably in excess of, the molar amount of free anionic residues on the fabric to which it is applied. It is advantageous for the molar amount of cationic material applied to be over 5 times, preferably over 25 times, more preferably over 100 times, the amount of free anionic residues on the fabric.
  • the amount used will depend partly on the method of its application to the fabric.
  • the amount present in the rinse liquor should be in molar excess of the total concentration of anionic surfactant in the liquor - indeed, it is preferred that the molar amount of cationic material be in this case at least 5 times greater, more preferably at least 10 times greater, than the concentration of anionic surfactant in the rinse liquor.
  • these dosage guidelines depend upon the amount of anionic material present in a given situation, both on the fabric being treated and in its surrounding environment. However, for a typical European machine wash, it may be appropriate for the cationic material to be applied in the final rinse cycle at a concentration of 0.07 - 1.4 mmol/l, preferably 0.15 - 0.7 mmol/1.
  • the cationic material used was di-[2-(hardened tallowoyloxy)ethyl] dimethyl ammonium chloride, added cold to the SDS as a pre-prepared liposomal dispersion in water.
  • Test materials were placed onto patches constructed of Finn Chambers on Fixomull tape. The patches were applied for two 23-hour periods, separated by one hour. Assessment of the skin irritation response (erythema, oedema and dryness) was carried out by expert skin assessors 24, 48 and 72 hours after the first patch application.
  • the assessment was based on the principle that an unbroken skin barrier prevents dye penetration whereas an irritant damaged barrier allows penetration of the dye.
  • an irritant damaged barrier allows penetration of the dye.
  • the fabric used in the following examples was prepared using 25cm by 50cm of cotton t-shirt material.
  • Comparative patches (hereinafter referred to as patch 'a') were prepared as follows. Cotton fabric squares were washed twice in a solution formed using a commercially available washing powder followed by washing ten times in boiling water to form a preharshened fabric. The fabric was then affixed to patches.
  • the washing powder used contained sodium linear alkylbenzene sulphonate (an anionic surfactant), together with nonionic surfactants, detergency builder, a bleach system, enzymes and perfume.
  • test patches (hereinafter referred to as test patches 'b' to 'e') were prepared as follows. Cotton fabric squares were preharshened (as above), then washed in a solution formed using the commercially available washing powder (522g) and hard water (156° FH), and dried. The squares were then dipped into a tray containing various amounts of concentrated fabric conditioner in aqueous solution, gently agitated for 5 minutes, removed from the solution, line dried and then affixed to patches.
  • the fabric conditioner used contained a concentrated dispersion in water of the 'active' 1,2-bis-[hardened tallowoyloxy]-3-trimethyl ammonium propane chloride, which is a biodegradable cationic fabric softening surfactant.
  • Each panellist had a preharshened control patch 'a' applied to one arm and a test patch selected from patches 'b', 'c', 'd' or 'e' applied to the other arm, as shown in table 3.
  • Examples of the invention are denoted by a number and comparative examples are denoted by a letter.
  • the washing powder used contained sodium linear alkylbenzene sulphonate (an anionic surfactant), together with nonionic surfactants, detergency builder, a bleach system and perfume.
  • the fabric conditioner used was a concentrated dispersion in water of the 'active' 1,2- bis -[hardened tallowoyloxy]-3-trimethyl ammonium propane chloride, which is a biodegradable cationic fabric softening surfactant.

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Claims (13)

  1. Verwendung eines kationischen Materials zur Verminderung der Hautirritation durch ein unter Verwendung von Wasser oder einer wässerigen Lösung aus einem Gewebe extrahierbaren Materials, wobei das kationische Material aus
    (i) kationischen oberflächenaktiven Mitteln,
    (ii) polykationischen Oligomeren, Polymeren, Co-Polymeren oder Gemischen davon, oder
    (iii) Gemischen aus (i) und (ii)
    ausgewählt ist und das aus einem Gewebe extrahierbare Material ein oder mehrere anionische oberflächenaktive Mittel und/oder einen oder mehrere Seifenrückstände umfasst.
  2. Verwendung nach Anspruch 1, wobei das kationische Material in dem Gewebe vorliegende freie anionische Rückstände neutralisiert.
  3. Verwendung nach Anspruch 1, wobei das kationische Material chemische Komplexe mit freien anionischen Rückständen auf dem Gewebe ausbildet.
  4. Verwendung nach Anspruch 1, wobei das kationische Material die nachfolgende Freisetzung freier anionischer Rückstände aus dem Gewebe verhindert oder mindestens behindert.
  5. Verwendung nach einem der vorhergehenden Ansprüche, wobei das kationische Material ein kationisches oberflächenaktives Mittel ist.
  6. Verwendung nach Anspruch 5, wobei das kationische oberflächenaktive Mittel ein quaternäres Ammoniummaterial ist, das entweder durch die Formel (1)
    Figure imgb0007
     wobei jede Gruppe R6 unabhängig aus C1-C4-Alkyl- oder - Hydroxyalkyl- oder C2-C4-Alkenylgruppen ausgewählt ist, jede Gruppe R7 unabhängig aus geradkettigen oder verzweigten C1-C4-Alkylengruppen ausgewählt ist, jede Gruppe R8 unabhängig aus C8-C28-, vorzugsweise C12-C18-Alkyl- oder - Alkenylgruppen ausgewählt ist,
    Figure imgb0008
     ist, und X- ein kompatibles Gegenion ist, oder durch die Formel (2)
    Figure imgb0009
     dargestellt wird,
    wobei R6, R8 und X- wie vorstehend definiert sind, und n eine ganze Zahl von 0 bis 5 ist.
  7. Verwendung nach einem der Ansprüche 1 bis 4, wobei das kationische Material ein polykationisches Oligomer, Polymer oder Co-Polymer wie Poly(ethylenimin) und/oder ein Derivat davon und/oder ein Additionspolymer oder Co-Polymer von Diallyldimethylammoniumchlorid und/oder quaternisiertem 2-(N,N-Dimethylamino)ethylmethacrylat ist.
  8. Verwendung nach Anspruch 7, wobei das polykationische Material zusammen mit einem oder mehreren kationischen Gewebe-weichmachenden oberflächenaktiven Mitteln verwendet wird.
  9. Verwendung nach einem der vorhergehenden Ansprüche, wobei das kationische Material in einer/einem Gewebebehandlungszusammensetzung oder -produkt enthalten ist.
  10. Verwendung nach einem der vorhergehenden Ansprüche, wobei das kationische Material während dem Spülen nach dem Waschen in einem Gewebewaschverfahren mit einem gewaschenen Gewebe in Kontakt gebracht wird.
  11. Verwendung nach einem der Ansprüche 1 bis 9, wobei das kationische Material direkt auf das Gewebe in Form eines Sprays oder einem Eintauchprodukt aufgebracht wird.
  12. Verwendung nach einem der Ansprüche 1 bis 9, wobei das kationische Material in einem Produkt für automatische Wäschetrockner verwendet wird.
  13. Verwendung nach einem der Ansprüche 2 bis 4 oder der davon abhängigen Ansprüche 5 bis 12, wobei die Menge der freien anionischen Reste auf dem Gewebe um mindestens 75 % vermindert wird.
EP99950531A 1998-09-21 1999-09-14 Verwendung von kationischen materialien und zusammensetzungen Revoked EP1115822B1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GBGB9820554.5A GB9820554D0 (en) 1998-09-21 1998-09-21 Use of cationic materials and compositions
GB9820554 1998-09-21
PCT/EP1999/006993 WO2000017297A1 (en) 1998-09-21 1999-09-14 Use of cationic materials and compositions

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EP1115822A1 EP1115822A1 (de) 2001-07-18
EP1115822B1 true EP1115822B1 (de) 2006-01-11

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AR (1) AR024210A1 (de)
AT (1) ATE315625T1 (de)
AU (1) AU6328299A (de)
BR (1) BR9913987B1 (de)
CA (1) CA2343137C (de)
DE (1) DE69929451T2 (de)
ES (1) ES2255305T3 (de)
GB (1) GB9820554D0 (de)
ID (1) ID28491A (de)
TR (1) TR200100833T2 (de)
WO (1) WO2000017297A1 (de)
ZA (1) ZA200101372B (de)

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US20100050346A1 (en) 2008-08-28 2010-03-04 Corona Iii Alessandro Compositions and methods for providing a benefit
MX2011002151A (es) 2008-08-28 2011-03-29 Procter & Gamble Composiciones para el cuidado de las telas, proceso para elaborarlas y metodos de uso.
WO2019012013A1 (en) 2017-07-14 2019-01-17 Unilever Plc METHOD FOR EVALUATING TISSUE CONDITIONING AGENT

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DE2943606A1 (de) * 1978-11-03 1980-05-14 Unilever Nv Textilweichmacher und verfahren zu ihrer herstellung
DE2904876A1 (de) * 1979-02-09 1980-08-21 Henkel Kgaa Mittel und verfahren zum nachbehandeln gewaschener waesche
DE3205317A1 (de) * 1982-02-15 1983-08-25 Henkel KGaA, 4000 Düsseldorf Mittel und verfahren zum nachbehandeln gewaschener waesche
DE3926740C2 (de) * 1989-08-12 1997-05-15 Witco Surfactants Gmbh Wässrige Weichspülmittel und deren Verwendung
GB9208405D0 (en) * 1992-04-16 1992-06-03 Unilever Plc Fabric conditioning composition

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ZA200101372B (en) 2002-02-19
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AR024210A1 (es) 2002-09-25
GB9820554D0 (en) 1998-11-11
CA2343137A1 (en) 2000-03-30
WO2000017297A1 (en) 2000-03-30
BR9913987A (pt) 2001-06-19
ES2255305T3 (es) 2006-06-16
ID28491A (id) 2001-05-31
DE69929451T2 (de) 2006-07-20
ATE315625T1 (de) 2006-02-15
EP1115822A1 (de) 2001-07-18
TR200100833T2 (tr) 2001-08-21

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