EP0332270A2 - Wäscheweichmacherzusammensetzung - Google Patents

Wäscheweichmacherzusammensetzung Download PDF

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Publication number
EP0332270A2
EP0332270A2 EP19890200545 EP89200545A EP0332270A2 EP 0332270 A2 EP0332270 A2 EP 0332270A2 EP 19890200545 EP19890200545 EP 19890200545 EP 89200545 A EP89200545 A EP 89200545A EP 0332270 A2 EP0332270 A2 EP 0332270A2
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EP
European Patent Office
Prior art keywords
fabric
fabric conditioning
amine
conditioning composition
composition according
Prior art date
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Granted
Application number
EP19890200545
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English (en)
French (fr)
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EP0332270A3 (en
EP0332270B2 (de
EP0332270B1 (de
Inventor
John Robert Martin
William Frederick Soutar Neillie
Graham Andrew Turner
Douglas Wraige
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Unilever PLC
Unilever NV
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Unilever PLC
Unilever NV
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Application filed by Unilever PLC, Unilever NV filed Critical Unilever PLC
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Publication of EP0332270A3 publication Critical patent/EP0332270A3/en
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Classifications

    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88Ampholytes; Electroneutral compounds
    • C11D1/94Mixtures with anionic, cationic or non-ionic compounds
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66Non-ionic compounds
    • C11D1/75Amino oxides
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005Other compounding ingredients characterised by their effect
    • C11D3/001Softening compositions
    • C11D3/0015Softening compositions liquid
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38Cationic compounds
    • C11D1/40Monoamines or polyamines; Salts thereof
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38Cationic compounds
    • C11D1/62Quaternary ammonium compounds

Definitions

  • This invention relates to a fabric conditioning composition suitable for conditioning fabrics during the rinse step of a fabric laundry process or during the drying stage in a tumble dryer device.
  • anionic surface active materials carried over from the wash cycle of the fabric laundry process can have a detrimental effect on the effectiveness of fabric conditioning compositions containing fabric softening agents which are used in the rinse step or the drying step of the fabric laundry process.
  • This problem can be alleviated if the fabrics are thoroughly rinsed before they are treated with a fabric conditioner, alternatively this problem can possibly be overcome by using fabric conditioning compositions which are not as sensitive to the presence of anionic surface active agents.
  • European patent 63 899 (UNILEVER), to overcome the problem of anionic carry-over by the use of anionic scavengers, such as aluminium chlorohydrate.
  • the fabric conditioning article according to the invention can alternatively be liquid, semi-solid or solid.
  • Preferred embodiments of a fabric conditioning composition are aqueous liquid detergent compositions, fabric conditioning compositions, which are applied to a substrate for use in the tumble dryer, and solid powdered compositions for use in a tumble dryer.
  • the fabric conditioning composition is an aqueous liquid detergent composition
  • the weight of (i) is at least 20 %, the weight of (ii) is at least 5% and the weight of (iii) is at least 5%.
  • each component is present at a level of at least 5%.
  • Fabric conditioning compositions according to the present invention comprise at least the following three active ingredients:
  • the cationic fabric softening agent The cationic fabric softening agent
  • the cationic fabric softener material is a cationic material which is water-insoluble in that these materials have a solubility in water at pH 2.5 and 20°C of less than 10 g/l.
  • Highly preferred materials are cationic quaternary ammonium salts having two C12-24 hydrocarbyl chains.
  • R1 and R2 represent hydrocarbyl groups from about 12 to about 24 carbon atoms
  • R3 and R4 represent hydrocarbyl groups containing from 1 to about 4 carbon atoms
  • X is an anion, preferably selected from halide, methyl sulfate and ethyl sulfate radicals.
  • quaternary softeners include ditallow dimethyl ammonium chloride; ditallow dimethyl ammonium methyl sulfate; dihexadecyl dimethyl ammonium chloride; di(hydrogenated tallow) dimethyl ammonium methyl sulfate; dihexadecyl diethyl ammonium chloride; di(coconut) dimethyl ammonium chloride.
  • ditallow dimethyl ammonium chloride, di(hydrogenated tallow) dimethyl ammonium chloride, di(coconut) dimethyl ammonium chloride and di(coconut) dimethyl ammonium methosulfate are preferred.
  • Suitable materials also include dialkyl ethoxyl methyl ammonium methosulphate based on soft fatty acid, dialkyl ethoxyl methyl ammonium methosulphate based on hard fatty acid, and a material in which R3 and R4 represent methyl, R1 is C13 ⁇ 15, R2 is CH2CH2OCOR, where R is stearyl, and X is methosulphate.
  • R2, R3 and R4 each represent methyl, R1 is the group where R is hardened tallow and X is methosulphate are also suitable.
  • Ditallow dimethyl ammonium chloride, di(hydrogenated tallow alkyl) dimethyl ammonium chloride, di(coconut alkyl) dimethyl ammonium chloride and di(coconut alkyl) dimethyl ammonium methosulfate are preferred.
  • hydrocarbyl group refers to alkyl or alkenyl groups optionally substituted or interrupted by functional groups such as -OH, -O-, -CONH, -COO-, etc.
  • R5 being partially hardened tallow, which is available from Stepan under the tradename Stepantex VRH 90 and where R8, R9 and R10 are each alkyl or hydroxyalkyl groups containing from 1 to 4 carbon atoms, or a benzyl group.
  • R6 and R7 are each an alkyl or alkenyl chain containing from 11 to 23 carbon atoms, and X ⁇ is a water soluble anion, substantially free of the corresponding monoester.
  • hydrocarbylimidazolinium salts believed to have the formula: wherein R13 is a hydrocarbyl group containing from 1 to 4, preferably 1 or 2 carbon atoms, R11 is a hydrocarbyl group containing from 8 to 25 carbon atoms, R14 is an hydrocarbyl group containing from 8 to 25 carbon atoms and R12 is hydrogen or an hydrocarbyl containing from 1 to 4 carbon atoms and A ⁇ is an anion, preferably a halide, methosulfate or ethosulfate.
  • Preferred imidazolinium salts include 1-methyl-1-­(tallowylamido-) ethyl -2-tallowyl- 4,5-dihydro imidazolinium methosulfate and 1-methyl-1-­(palmitoylamido)ethyl -2-octadecyl-4,5- dihydro­imidazolinium chloride.
  • Other useful imidazolinium materials are 2-heptadecyl-1-methyl-1- (2-stearylamido)­ethyl-imidazolinium chloride and 2-lauryl-1-­hydroxyethyl-1-oleyl-imidazolinium chloride.
  • Also suitable herein are the imidazolinium fabric softening components of US patent No 4 127 489, incorporated by reference.
  • Representative commercially available materials of the above classes are the quaternary ammonium compounds Arquad 2HT (ex AKZO); Noramium M2SH (ex CEKA); Aliquat-­2HT (Trade Mark of General Mills Inc), Stepantex Q185 (ex Stepan); Stepantex VP85 (ex Stepan); Stepantex VRH90 (ex Stepan); Synprolam FS (ex ICI) and the imidazolinium compounds Varisoft 475 (Trade Mark of Sherex Company, Columbus Ohio) and Rewoquat W7500 (Trade Mark of REWO).
  • compositions according to the invention also contain in addition to cationic fabric softening agents, one or more amines.
  • R15 is a C6 to C24, hydrocarbyl group
  • R16 is a C1 to C24 hydrocarbyl group
  • R17 is a C1 to C10 hydrocarbyl group.
  • Suitable amines include those materials from which the quaternary ammonium compounds disclosed above are derived, in which R15 is R1, R16 is R2 and R17 is R3.
  • the amine is such that both R15 and R16 are C6-C20 alkyl with C16-C18 being most preferred and with R17 as C1 ⁇ 3 alkyl, or R15 is an alkyl or alkenyl group with at least 22 carbon atoms and R16 and R12 are C1 ⁇ 3 alkyl.
  • thee amines are protonated with hydrochloric acid, orthophosphoric acid (OPA), C1 ⁇ 5 carboxylic acids or any other similar acids, for use in the fabric conditioning compositions of the invention.
  • R18 is a C6 to C24 hydrocarbyl group
  • R19 is an alkoxylated group of formula -(CH2CH2O) y H, where y is within the range from 0 to 6
  • R20 is an alkoxylated group of formula -(CH2CH2O) z H where z is within the range from 0 to 6 and m is an integer within the range from 0 to 6, and is preferably 3.
  • m it is preferred that R18 is a C16 to C22 alkyl and that the sum total of z and y is within the range from 1 to 6, more preferably 1 to 3.
  • m is 1, it is preferred that R18 is a C16 to C22 alkyl and that the sum total of x and y and z is within the range from 3 to 10.
  • Representative commercially available materials of this class include Ethomeen (ex Armour) and Ethoduomeen (ex Armour).
  • the amines of type (ii) or (iii) are also protonated for use in the fabric conditioning compositions of the invention.
  • R22 and R23 are divalent alkenyl chains having from 1 to 3 carbons atoms
  • R24 is an acyclic aliphatic hydrocarbon chain having from 15 to 21 carbon atoms.
  • a commercially available material of this class is Ceranine HC39 (ex Sandoz).
  • the amphoteric fabric conditioning material is amphoteric fabric conditioning material
  • the amphoteric fabric conditioning material for use in a composition according to the invention should be a fabric substantive amphotheric material. Suitable amphoteric materials form a particulate dispersion at a concentration of less than 1 g/l at at least one temperature between 0 and 100°C.
  • a fabric substantive amphoteric material is preferably an amphoteric or zwitterionic tertiary or quaternary ammonium compound having either one single very long hydrocarbyl side chain or two long hydrocarbyl chains. From these compounds the use of amphoteric or zwitterionic ammonium compounds having two long hydrocarbyl chains is particularly preferred for many reasons including costs, ease of processing and better stability and performance.
  • Amphoteric or zwitterionic ammonium compounds preferably have two long hydrocarbyl chains, each chain having 8-24 C-atoms, preferably 10-20 C-atoms, most preferred around 16 C-atoms.
  • Suitable amphoteric fabric substantive materials for use in a fabric treatment composition according to the invention are for instance:
  • amphoteric fabric substantive materials are water insoluble and have a solubility in water at pH 2.5 at 20°C of less than 10 g/l.
  • the HLB of the amphoteric fabric substantive material is preferably less than 10.0.
  • amphoteric materials of the above groups and their method of preparation are given in our co-pending European patent application 89200113.2.
  • group V materials are preferred, especially those amine oxides containing two hydrocarbyl groups with at least 14 C-­atoms, such as dihardened tallow methyl amine oxide, or one hydrocarbyl group with at least 22 carbon atoms.
  • Amine oxides have been found to provide particularly advantageous softening effects, furthermore compositions comprising amine oxides are clearly preferred because they are generally easy to prepare, are stable and have an interesting creamy appearance.
  • compositions of the present invention contain substantially no anionic material, in particular no anionic surface active material. If such materials are present, the weight ratio of the cationic fabric softening agent to the anionic material should preferably be more than 5:1.
  • the composition can also contain one or more optional ingredients selected from non-aqueous solvents such as C1-C4 alkanols and polyhydric alcohols, pH buffering agents such as strong or weak acids eg. HCl, H2SO4, phosphoric, benzoic or citric acids (the pH of the liquid compositions ie preferably less than 5.0), rewetting agents, viscosity modifiers such as electrolytes, for example calcium chloride, antigelling agents, perfumes, perfume carriers, fluorescers, colourants, hydrotropes, antifoaming agents, antiredeposition agents, enzymes, optical brightening agents, opacifiers, stabilisers such as guar gum and polyethylene glycol, emulsifiers, anti-shrinking agents, anti-wrinkle agents, fabric crisping agents, anti-­spotting agents, soil-release agents, germicides, linear or branched silicones, fungicides, anti-oxidants, anti-­corrosion agents, preservatives such as Bro
  • compositions are each present at levels up to 5% by weight of the composition.
  • the pH of the composition is preferably 5 or below, or adjusted thereto.
  • Anti-redeposition agents particularly preferred in the compositions according to the invention are polymers.
  • Suitable polymers include alkyl and hydroxoyalkyl cellulose ethers, such as methyl cellulose, and polyvinylpyrrolidone.
  • Silicones can be included in the compositions as the ironing aid, rewetting agent or the antifoaming agent.
  • Suitable silicones for use in the compositions according to the invention include predominantly linear polydialkyl or alkylaryl siloxanes in which the alkyl groups contain one to five carbon atoms.
  • the siloxanes can be amido or amino substituted. When the siloxane is amine substituted the amine group may be quaternised.
  • compositions may also contain, in addition to the cationic fabric softening agent, other non-cationic fabric softening agents, such as nonionic fabric softening agents.
  • Suitable nonionic fabric softening agents include glycerol esters, such as glycerol mono­stearate, fatty alcohols, such as stearyl alcohol, alkoxylated fatty alcohols C9-C24 fatty acids and lanolin and derivatives thereof.
  • Suitable materials are disclosed in European Patent Application 88 520 (Unilever PLC/NV case C 1325), 122 141 (Unilever PLC/NV case C 1363) and 79 746 (Procter and Gamble), the disclosures of which are incorporated herein by reference. Typically such materials are included at a level within the range of from 0.5% to 10% by weight of the composition.
  • compositions according to the present invention are an aqueous liquid fabric conditioning composition comprising cationic fabric softener, the amine and the amphoteric softener material.
  • the amphoteric softener material is preferably an amine oxide.
  • the total level of the three ingredients in a liquid composition is preferably from 1 to 60% more preferred from 3 to 30% by weight of the composition.
  • the weight of the cationic softening agent is not more than 90%, preferably between 25 and 75 %, more preferred from 40 to 60 %. especially preferred about 50 %.
  • the weight of the amine is not more than 70%, preferably between 10 and 60%, more preferred between 15 and 40 %, especially preferred about 25 %.
  • the weight of the amphoteric material is not more than 60 %. If the amphoteric material is an amine oxide then this constitutes preferably less than 60 %, more preferred between 10 and 50 %, especially preferred between 15 and 40 %, most preferred about 25 % based on the weight of the three actives.
  • the optimum weight ratio of the three active components in the fabric conditioning composition depends on the level of anionic carried over from the wash cycle. We have found that a weight ratio of cationic fabric softener to amine to amine oxide of about 2:1:1 provides good results under most conditions of use.
  • liquid compositions according to the inventions may be prepared by a variety of methods.
  • One suitable method is to form a molten mixture of the cationic fabric softening agent, amine and amphoteric material, which is then added to water with stirring to form a dispersion and thereafter adding any optional ingredients.
  • the fabric conditioning composition of the invention may be added to a large volume of water to form a liquor with which the fabrics to be treated are contacted.
  • the total concentration of the cationic fabric softening agent, the amine and the amine oxide in this liquor will be between about 30 ppm and 500 ppm.
  • the weight ratio of the fabrics to liquor will generally be between 40:1 and 4:1.
  • compositions of the invention are added to water which contains high levels of anionic surface active materials, a further improvement can be obtained if the compositions contain anionic scavengers such as low molecular weight cationics.
  • Suitable materials include cationic compounds which have a solubility in water at pH 2.5 and 20°C of more than 5 g/l, preferably more than 10 g/l.
  • Arquad 18 is a particularly preferred material. (Arquad 18 is a commercially available form of hardened tallow trimethyl ammonium chloride).
  • Another preferred embodiment of the present invention involves the combination of a substrate and a mixture of active ingredients comprising a cationic fabric conditioner, an amine and an amphoteric material. Also in these compositions the amphoteric material is preferably an amine oxide.
  • the substrate for use in a fabric conditioning article according to the present invention may take any one of a variety of shapes such as blocks, rods, flakes, balls or sheets.
  • the conditioning article comprises one or more flexible sheet substrates.
  • Such substrates are well-known in the art and include woven and non-woven fibrous substrates, polymeric substrates, extruded substrates etc. Suitable substrates are for instance disclosed in CA 1 005 204 (Procter and Gamble).
  • Combinations of a substrate and a fabric conditioner according to the invention may be prepared by any suitable method for the application of active materials onto a substrate. Such a method may for instance include the coating or impregnation of the substrate with the fabric conditioner. When using such a method, it may be preferred to combine the active materials with a solvent for these, followed by applying the solution to the substrate and evaporating said solvent, for instance under low pressure conditions.
  • the add-on ratio of the fabric conditioning material to the substrate is between 20:1 and 1:20, more preferred between 1:1 and 10:1.
  • a combination of a substrate and a fabric conditioner material in which the total amount of conditioner material is 0.5 and 10 g, more preferred between 0.75 and 7.5 g, especially preferred between 1 and 5 g.
  • a fabric conditioning composition according to the present invention is a composition which is solid, preferably in the form of a powdered material. These materials are preferably used during the treatment of the fabrics in a tumble dryer. In this use they may for instance be contained in a sachet or another dispensing container. Suitable containers for use in the tumble dryer are for instance disclosed in EP 194 813 (Unilever N.V.).
  • the solid fabric conditioner composition according to the present invention are preferably used in amounts of between 0.5 and 10 g, preferably from 1 to 5 g, especially preferred from 1.5 to 3 g active material.
  • the fabric conditioner compositions for application to the substrate or for use in solid form comprise, based on the weight of the three active materials, more than 5 % fabric softener material, more than 5 % amine and more than 5 % amphoteric material.
  • the amount of fabric softener material is from 5 to 90 %, more preferred from 20 to 85%, especially preferred about 80 %.
  • the weight of the amine is preferably from 5 to 50 %, more preferred from 5 to 40 %, especially preferred from 5 to 35 %, most preferred about 10 %.
  • the weight of the amphoteric material is preferably from 5 to 90%, if the amphoteric material is an amine oxide, the weight of this material is preferably from 5 to 50%, more preferred from 5 to 35 %, especially preferred from 5 to 25 %, typically about 10%.
  • compositions were prepared according to the formulations in the following tables.
  • the compositions were prepared by comelting the cationic fabric softening agent, amine and amine oxide at 80°C. (When the amine was Armeen M2HT, the ortho phosphoric acid was added to the water prior to forming the co-melt. In contrast when Ceranine HC39 was used, the acid was added after the components were dispersed). The comelt thus formed was added to water at 80°C and then soniprobed for a few minutes to form a disperion which was then cooled to room temperature.
  • compositions were tested as follows - 40 grams of cotton terry toweling were washed for 5 minutes at 50°C with a commercially available washing powder product, UK Persil Automatic, in a litre of Wirral water (10°FH) in a tergotometer. 5 grams of the washing powder product was used. After separating the wash liquor, the fabric load was rinsed twice at 25°C with Wirral water. 4ml of a test composition was added to the second rinse. After line drying, the fabric load was assessed for softness by a panel of experts using a paired comparison test. EXAMPLE NO.
  • compositions 1A and 1B ie. the ternary system, containing the cationic, amine and amine oxide, gave the best softening.
  • compositions 2, 2A and 2B were compared.
  • compositions 1 and 2 were also compared. The results showed a preference for the product containing Ceranine HC39.
  • compositions were prepared according to the formulations in the table by the method described above.
  • Example 3 4 5 6 Arquad 2HT 2.5 2.5 2.5 2.5 2.5 Armeen M2HT (i) protonated with OPA 1.25 - - - (ii) not protanated - 1.25 - - DHTMAO 1.25 1.25 1.25 1.25 Ceranine HC39 (i) protonated with OPA - - 1.25 - (ii) not protanated - - - 1.25 OPA 0.25 - 0.25 - Water balance
  • compositions were tested according to the method described in Examples 1 and 2.
  • composition 3 which contained a protonated amine
  • compositions according to the invention were prepared by the method described above.
  • compositions according to the invention were prepared by the method described above Example 16 17 18 19 20 21 Arquad 2HT 7.5 6.75 7.50 8.5 7.5 5.1 Ceranine HC39 3.75 3.375 3.75 - - 8.5 Ceranine HCA - - - 4.25 3.75 - DHTMAO 3.75 3.375 3.75 4.25 3.75 3.4 Dobanol 25-9 - - 1.00 - - - OPA 0.75 0.22 0.75 0.85 0.75 0.70 Water balance
  • Tumble dryer sheet product were prepared as follows. Arquad 2HT, Ceranine HC39 and DHTMAO were used as the active materials. The active materials were melted together and about 3g of the mix was blended with 10 ml of chloroform. The active was absorbed on an apertured non-woven polyester substrate of 11 cm x 9 cm ex J.R. Crompton plc, the substrate was subsequently dried.
  • Example Weight of active on sheet (g) % active removed in drying ratio AO:HC39:2HT -score 22 2.44 22 8 : 1 : 1 2.99 23 2.49 27 6 : 2 : 2 3.79 24 2.22 37 1 : 1 : 1 3.90 25 2.52 42 1 :4.5:4.5 4.13 26 2.41 34 1 : 1 : 8 5.19 27 2.40 47 4.5:4.5:1 4.21 28 2.10 77 BOUNCE 2.87 29 - - - 1.96
  • Ternary active mixtures according to examples 22 - 29 were melted cooled and ground to obtain powdered softening compositions.
  • the powders were introduced in an apertured cup comprising a bottom compartment such as disclosed in Fig. 1 of EP 204 484 (Unilever N.V.).
  • the actives were extracted from a BOUNCE sheet using chloroform, followed by drying and grinding.
EP89200545A 1988-03-11 1989-03-06 Wäscheweichmacherzusammensetzung Expired - Lifetime EP0332270B2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB8805837 1988-03-11
GB888805837A GB8805837D0 (en) 1988-03-11 1988-03-11 Fabric conditioning composition

Publications (4)

Publication Number Publication Date
EP0332270A2 true EP0332270A2 (de) 1989-09-13
EP0332270A3 EP0332270A3 (en) 1990-05-16
EP0332270B1 EP0332270B1 (de) 1996-06-05
EP0332270B2 EP0332270B2 (de) 2001-07-04

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EP89200545A Expired - Lifetime EP0332270B2 (de) 1988-03-11 1989-03-06 Wäscheweichmacherzusammensetzung

Country Status (9)

Country Link
EP (1) EP0332270B2 (de)
JP (1) JP2551479B2 (de)
AU (1) AU620082B2 (de)
BR (1) BR8901135A (de)
CA (1) CA1341483C (de)
DE (1) DE68926584T3 (de)
ES (1) ES2087861T5 (de)
GB (1) GB8805837D0 (de)
ZA (1) ZA891845B (de)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0368383A2 (de) * 1988-11-09 1990-05-16 Unilever N.V. Textilweichmacher
EP0423894A2 (de) * 1989-10-16 1991-04-24 Colgate-Palmolive Company Weichspülerzusammensetzungen und Verfahren zu deren Herstellung und Verwendung
EP0443313A1 (de) * 1990-01-19 1991-08-28 Kao Corporation Flüssige Textilweichmacherzusammensetzung
WO1995013346A1 (en) * 1993-11-11 1995-05-18 Unilever Plc Fabric conditioning composition
WO1996013565A1 (en) * 1994-10-28 1996-05-09 The Procter & Gamble Company Hard surface cleaning compositions comprising protonated amines and amine oxide surfactants
US5554588A (en) * 1991-11-08 1996-09-10 Lever Brothers Company, Division Of Conopco, Inc. Perfume compositions
WO1999060082A1 (en) * 1998-05-18 1999-11-25 Unilever Plc Stable quaternary ammonium compositions
EP0990695A1 (de) * 1998-09-30 2000-04-05 Witco Surfactants GmbH Weichspülmittel mit farberhaltender Wirkung
EP1154067A1 (de) * 1999-11-12 2001-11-14 Kao Corporation Weichmacherzusammensetzung
WO2002092742A1 (en) * 2001-05-11 2002-11-21 Reckitt Benckiser N.V. Fabric softening composition
US6887542B2 (en) * 2002-12-11 2005-05-03 Kimberly-Clark Worldwide, Inc. Method for treating an elastomeric article
EP4177326A1 (de) 2021-11-05 2023-05-10 Nouryon Chemicals International B.V. Flüssige weichspülerzusammensetzungen mit hydroxypropylstärkephosphat

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2097503C (en) * 1991-02-08 1997-04-08 Albemarle Corporation Laundry rinses and dryer sheets
EP1017771A1 (de) * 1997-09-25 2000-07-12 The Procter & Gamble Company Chlorfänger scavenger enthaltende wäscheweichtrocknerzusatzzusammensetzung um farbe- und gewebeausehen-eigenschaften zubesitzen

Citations (10)

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DE2805767A1 (de) 1977-02-15 1978-08-17 Unilever Nv Textilkonditionierungsmittel, verfahren zu ihrer herstellung und ihre verwendung
US4238531A (en) 1977-11-21 1980-12-09 Lever Brothers Company Additives for clothes dryers
EP0026528A1 (de) * 1979-09-29 1981-04-08 THE PROCTER & GAMBLE COMPANY Reinigungsmittelzusammensetzungen
EP0125031A1 (de) 1983-04-08 1984-11-14 Unilever Plc Flüssige Gewebeweichmacher-Zusammensetzung
GB2160886A (en) * 1984-06-20 1986-01-02 Firmenich & Cie Detergent article having softening action and process for its preparation
EP0199382A2 (de) * 1985-03-28 1986-10-29 The Procter & Gamble Company Flüssiger Wäscheweichmacher
EP0210704A2 (de) * 1985-08-01 1987-02-04 Procter & Gamble European Technical Center Dispergierbare Wäscheweichmacher
FR2593517A1 (fr) * 1986-01-27 1987-07-31 Colgate Palmolive Co Composition detergente et assouplissante particulaire pour tissus, procede pour la preparer et son application au lavage des tissus
EP0239910A2 (de) 1986-04-02 1987-10-07 The Procter & Gamble Company Biologisch abbaubare Gewebeweichmacher
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US4238531A (en) 1977-11-21 1980-12-09 Lever Brothers Company Additives for clothes dryers
EP0026528A1 (de) * 1979-09-29 1981-04-08 THE PROCTER & GAMBLE COMPANY Reinigungsmittelzusammensetzungen
EP0125031A1 (de) 1983-04-08 1984-11-14 Unilever Plc Flüssige Gewebeweichmacher-Zusammensetzung
GB2160886A (en) * 1984-06-20 1986-01-02 Firmenich & Cie Detergent article having softening action and process for its preparation
EP0199382A2 (de) * 1985-03-28 1986-10-29 The Procter & Gamble Company Flüssiger Wäscheweichmacher
EP0210704A2 (de) * 1985-08-01 1987-02-04 Procter & Gamble European Technical Center Dispergierbare Wäscheweichmacher
FR2593517A1 (fr) * 1986-01-27 1987-07-31 Colgate Palmolive Co Composition detergente et assouplissante particulaire pour tissus, procede pour la preparer et son application au lavage des tissus
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DD251784A1 (de) 1986-08-01 1987-11-25 Bitterfeld Chemie Weichspueler fuer textile flaechenfasergebilde

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EP0368383A2 (de) * 1988-11-09 1990-05-16 Unilever N.V. Textilweichmacher
EP0368383A3 (de) * 1988-11-09 1991-07-03 Unilever N.V. Textilweichmacher
EP0423894A2 (de) * 1989-10-16 1991-04-24 Colgate-Palmolive Company Weichspülerzusammensetzungen und Verfahren zu deren Herstellung und Verwendung
GR900100745A (en) * 1989-10-16 1992-03-20 Colgate Palmolive Co New smoothing compositions and preparation method therefor
EP0423894A3 (en) * 1989-10-16 1992-04-22 Colgate-Palmolive Company New softening compositions and methods for making and using same
EP0443313A1 (de) * 1990-01-19 1991-08-28 Kao Corporation Flüssige Textilweichmacherzusammensetzung
US5554588A (en) * 1991-11-08 1996-09-10 Lever Brothers Company, Division Of Conopco, Inc. Perfume compositions
WO1995013346A1 (en) * 1993-11-11 1995-05-18 Unilever Plc Fabric conditioning composition
WO1996013565A1 (en) * 1994-10-28 1996-05-09 The Procter & Gamble Company Hard surface cleaning compositions comprising protonated amines and amine oxide surfactants
WO1999060082A1 (en) * 1998-05-18 1999-11-25 Unilever Plc Stable quaternary ammonium compositions
EP0990695A1 (de) * 1998-09-30 2000-04-05 Witco Surfactants GmbH Weichspülmittel mit farberhaltender Wirkung
EP1154067A1 (de) * 1999-11-12 2001-11-14 Kao Corporation Weichmacherzusammensetzung
EP1154067A4 (de) * 1999-11-12 2004-12-15 Kao Corp Weichmacherzusammensetzung
WO2002092742A1 (en) * 2001-05-11 2002-11-21 Reckitt Benckiser N.V. Fabric softening composition
US6887542B2 (en) * 2002-12-11 2005-05-03 Kimberly-Clark Worldwide, Inc. Method for treating an elastomeric article
EP4177326A1 (de) 2021-11-05 2023-05-10 Nouryon Chemicals International B.V. Flüssige weichspülerzusammensetzungen mit hydroxypropylstärkephosphat

Also Published As

Publication number Publication date
EP0332270A3 (en) 1990-05-16
AU620082B2 (en) 1992-02-13
ES2087861T3 (es) 1996-08-01
JPH026662A (ja) 1990-01-10
GB8805837D0 (en) 1988-04-13
DE68926584T3 (de) 2001-09-27
CA1341483C (en) 2005-05-17
DE68926584D1 (de) 1996-07-11
JP2551479B2 (ja) 1996-11-06
EP0332270B2 (de) 2001-07-04
BR8901135A (pt) 1989-10-31
ES2087861T5 (es) 2001-10-16
AU3124389A (en) 1989-09-14
DE68926584T2 (de) 1996-10-02
ZA891845B (en) 1990-11-28
EP0332270B1 (de) 1996-06-05

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