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EP0404471B1 - Composition adoucissante pour le linge - Google Patents

Composition adoucissante pour le linge Download PDF

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Publication number
EP0404471B1
EP0404471B1 EP90306600A EP90306600A EP0404471B1 EP 0404471 B1 EP0404471 B1 EP 0404471B1 EP 90306600 A EP90306600 A EP 90306600A EP 90306600 A EP90306600 A EP 90306600A EP 0404471 B1 EP0404471 B1 EP 0404471B1
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EP
European Patent Office
Prior art keywords
acid
weight
fabric softening
fabric
materials
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.)
Revoked
Application number
EP90306600A
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German (de)
English (en)
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EP0404471A1 (fr
Inventor
David Machin
William Frederick Soutar Neillie
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.)
Unilever PLC
Unilever NV
Original Assignee
Unilever PLC
Unilever NV
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
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Publication of EP0404471A1 publication Critical patent/EP0404471A1/fr
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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
    • 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
    • D06M13/46—Compounds containing quaternary nitrogen atoms
    • 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
    • C11D3/0015—Softening compositions liquid
    • 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
    • C11D3/2075—Carboxylic acids-salts thereof

Definitions

  • the present invention relates to fabric softening compositions suitable for softening fabrics in the rinse step of a fabric laundry process.
  • compositions comprising a combination of fabric softening materials and organic acids, in specific polycarboxylic acids.
  • the compositions as disclosed in this document are of low active levels of up to about 10% by weight.
  • These compositions of low active level are of lamellar structure, wherein the molecules of the fabric softening material form an onion-like configuration comprising concentric bilayers of softening material, between which is trapped an aqueous phase containing the dissolved acid ingredient.
  • compositions unexpectedly are isotropic, they do not comprise a structure of active ingredients. These isotropic compositions are preferred over lamellar compositions in that they are more resistant to temperature fluctuations, and they allow a more flexible use of ingredients.
  • US-A-4,060,505 discloses a stable homogeneous liquid composition for souring and softening textiles, containing 0.5-25% by weight of a fatty amide softening agent of a specific structural formula and 7.5-75% by weight of a water soluble organic carboxylic acid containing about 1-20 carbon atoms.
  • liquid compositions are prepared containing 1.3% by weight of a fatty amide softening agent.
  • US-A-3,984,335 discloses a stable homogeneous liquid composition for souring and softening textiles, which includes about 0.5-25% by weight of a fatty amide softening agent and about 7.5-75% of a water soluble organic carboxylic acid.
  • liquid compositions are prepared containing 1.3% and 3% by weight of softening agent.
  • EP-A-0,043,622 describes a concentrated fabricsoftening composition comprising a water-insoluble cationic softener and a viscosity regulator system.
  • the viscosity regulator system includes two components, the first of which may be a C10-C24 fatty acid or ester thereof.
  • the softener is present in a concentration of between 8 and 22%, and the first regulator component in a concentration of between 0.5 and 6%. Of the Examples quoted in this document, only one contains a fatty acid (stearic acid), at a concentration of 2%.
  • EP-A-0,123,999 describes aqueous, free-flowing concentrates containing a fabric-softening quaternary ammonium compound and an alkali metal soap or the corresponding fatty acid (typically a C8- C20 acid).
  • the claims of the document refer to a softener concentration of at least 30 weight percent. Typical fatty acid concentrations are said to be between 1 and 10 weight percent. In the Examples quoted, fatty acid concentrations of 3% are used.
  • US-A-3,954,630 discloses a fabric treating composition including a cationic fabric softening agent and an organic "complexing acid".
  • the document relates to the use of such a composition during a rinse cycle treatment, the composition upon dilution containing between 0.01 and 0.1% by weight of the softening agent and between 0.01 and 0.1% by weight of the complexing acid.
  • the composition In its concentrated form, the composition contains from 0 to 25% by weight of the softener.
  • EP-A-0,346,634 is prior art under Article 54(3) and (4) EPC, for the purposes of Spain only. It describes a liquid laundry-conditioning agent containing, as a fabric softener, a quaternary ammonium compound having two 2-acyloxyalkyl groups. The agent also contains a (typically C8 - C24) fatty acid. The softener is present at a concentration of between 1.5 and 27 weight percent, and the fatty acid at a concentration of between 0.5 and 10 weight percent.
  • EP-A-0,387,064 also represents prior art for the purposes of Article 54(3) and (4) EPC only, for all states designated in the present application. It discloses a liquid fabric conditioner composition comprising an aqueous base, a cationic fabric softening material and ethylene glycol distearate.
  • the composition may also include a fatty acid material, preferably a C8 - C24 acid material.
  • the concentration of softener material ranges from 4.8 to 5.2% while a fatty acid is present at a concentration of 0.5 weight percent.
  • the present invention relates to isotropic liquid fabric softening compositions comprising
  • the isotropic compositions of the present invention are clear or translucent.
  • Softening compositions which are clear are sometimes particularly appreciated by the consumer, because of their fresh and natural appearance. Clear compositions can be made by ensuring that all ingredients of the composition are completely dissolved in the liquid phase.
  • Compositions according to the invention contain 30 to 50% by weight of a fabric softening material.
  • This material may be selected from cationic, nonionic and amphoteric softening materials, and mixtures thereof.
  • Suitable cationic fabric softener materials include water-insoluble cationic materials having a solubility in water at pH 2.5 and 20°C of less than 10g/l. Highly preferred materials are cationic quaternary ammonium salts having two C12 ⁇ 14 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 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 or R2 is methyl
  • R3 and R4 each represent where R is hardened tallow
  • R1 is CH2CH2OH and X is methosulphate
  • cationic softeners which have an active melting point (transition from Lb to L state) of less than 25°C, more preferred less than 20°C.
  • active melting point transition from Lb to L state
  • these materials are di-unhardened-tallow dimethyl ammonium chloride and di coconut dimethyl ammonium chloride.
  • hydrocarbyl group refers to alkyl or alkenyl groups optionally substituted or interrupted by functional groups such as -OH, -O-, -CONH, -COO-, etc.
  • R5 being talow, 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).
  • the fabric softening materials may also comprise instead of or 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.
  • these 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 a 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 13.
  • 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 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).
  • Alkoxylated fatty amides or amines may also be used as fabric softening materials in compositions of the invention. Suitable materials are for instance disclosed in EP 159 921 (Unilever) and EP 159 919 (Unilever).
  • the fabric softening material may also comprise instead of or in addition to the above mentioned softening materials one or more fabric substantive amphoteric fabric softening materials. Suitable amphoteric materials form a particulate dispersion at a concentration of less than 1g/l 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 zwitterionics 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: ampholytes, hydrocarbyl betaines, hydrocarbylamide betaines, glycinates, propionates and tertiary amine oxides. These materials are described in our co-pending patent application EP-0,332,270.
  • amphoteric softening materials are tertiary amine oxides of the following formula wherein:
  • amphoteric fabric substantive materials are water soluble and have a solubility in water at pH 2.5 at 20°C of less than 10g/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 EP-0,326,213.
  • compositions may also contain, instead of or in addition to the above mentioned fabric softening agents, non-cationic fabric softening agents, such as nonionic fabric softening agents.
  • nonionic fabric softening agents include glycerol esters, such as glycerol mono-stearate, fatty alcohols, such as stearyl alcohol, alkoxylated fatty alcohols C9-C24 fatty acids such as Dobanol 91-6 (SHELL) and lanolin and derivatives thereof.
  • Suitable materials are disclosed in European Patent Application 88 520 (Unilever PLC/NV case C1325), 122 141 (Unilever PLC/NV case C1363) and 79 746 (Procter and Gamble), the disclosure of which are incorporated herein by reference.
  • compositions of the invention contain at least some cationic fabric softening materials.
  • at least 50% of the fabric softening material is a cationic fabric softener material.
  • the total level of softening material is comprised between 30 and 50% by weight, preferably between 35 and 50% by weight, typically between 40 and 50% by weight of the composition.
  • 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 organic acid material is the organic acid material
  • the organic acid material for use in compositions of the present invention may be selected from the group of mono-, di-, tri- or polycarboxylic acids preferably having a total number of carbon atoms of 8 or less, preferably 4 or less.
  • Suitable organic acid materials are succinic acid, malic acid, tartaric acid, citric acid, glutaric acid, acetic acid, propionic acid, and lactic acid or mixtures thereof.
  • succinic acid malic acid, tartaric acid, citric acid, glutaric acid, acetic acid, propionic acid, and lactic acid or mixtures thereof.
  • lactic acid and acetic acid is preferred.
  • citric acid is preferred.
  • the level of acid material in the composition (calculated on an anhydrous basis) of the acid material is comprised between 5 and 40% by weight, preferably between 10 and 40% by weight, typically between 15% and 35% by weight of the composition.
  • 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, rewetting agents, viscosity modifiers such as electrolytes, for example calcium chloride, antigelling agents, perfumes, perfume carriers, fluorescers, colourants, hydrotropes, antifoaming agents, hydrocarbons, antiredeposition agents, enzymes, optical brightening agents, opacifiers, stabilisers such as guar gum and polyethylene glycol, emulsifiers, anti-shrinking agents, lanolin or lanolin like materials, 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 Bronopol (Trade Mark), a commercially available form of 2-bromo-2-nitropropane-1,3-diol,
  • These optional ingredients, if added, are each present at levels up to 5% by weight of the composition, except for the hydrocarbons and the non-aqueous solvents which may be included at levels of up to 30%.
  • the pH of the composition is preferably below the pK of the organic acid, more preferred at least one unit below the pK, typically between 2.0 and 5.0.
  • Soil-release agents particularly preferred in the compositions according to the invention are polymers.
  • Suitable polymers include alkyl and hydroxyalkyl 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.
  • Fatty acid materials or other nonionic extenders can also be included in compositions of the present invention. Suitable materials and their amounts are for instance disclosed in EP 13780 (P&G) and DE 29 43 606 (Unilever).
  • the balance of the composition is preferably water. Although water-free systems are also within the ambit of the invention, preferably the amount of water in the composition is more than 20% by weight, more preferred more than 25% by weight. Generally the water level will be less than 70%, more preferred less than 60%, most preferred less than 55%, typically between 55% and 25%.
  • the viscosity of the product is preferably less than 250 mPas at 106 s-1.
  • compositions of the present invention may be prediluted or dosed in concentrated form into the rinse-cycle of a fabric washing process.
  • the material is used at a concentration of between 0.01 and 2g/l, especially between 0.1 and 1g/l.
  • Fabric softening compositions containing water, tartaric acid (on a dry basis) and a cationic fabric softening material Prapagen 3445 (70% di-unhardened tallow di-methyl ammonium chloride 20% isopropylalcohol, 10% water) were prepared by mixing under light agitation.
  • Example 1 was repeated while tartaric acid was replaced by citric acid. The results are expressed in table 1 and figure 2.
  • COMPOSITION WATER/PRAPAGEN/CITRIC (%) RESULT 20. 80/10/10 lamellar/milky 21. 70/10/20 lamellar/milky 22. 60/10/30 lamellar/milky 23. 50/10/40 gel 24. 70/20/10 gel 25. 60/20/20 gel 26. 50/20/30 gel 27. 40/20/40 gel 28. 60/30/10 gel 29. 50/30/20 gel 30. 40/30/30 isotropic/clear 31. 30/30/40 phase separation 32. 50/40/10 isotropic/clear 33. 40/40/20 isotropic/clear 34. 30/40/30 isotropic/clear 35. 40/50/10 phase separation 36. 30/50/20 phase separation
  • compositions 30, 32, 33, 34 can be formulated by increasing the level of fabric softening materials. Especially interesting was the clear natural yellow appearance of the product, no decolouration was observed during storage.
  • Example I was repeated while replacing tartaric acid by acetic acid or by lactic acid.
  • acetic acid isotropic/clear compositions could be formulated even at levels of PRAPAGEN of 50% or more. At lower concentrations a similar behaviour as observed for tartaric acid was observed: lamellar systems at low concentrations, and gelled systems at intermediate concentrations of softening material.
  • Typical formulations are: Formulation % by weight A B C D Arquad 2T 40 40 40 40 Isopropylalcohol 0 5 11 0 Propylene glycol 10 10 0 Propionic acid 10 10 5 30 Water - - -- - balance - - - - -- -

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Textile Engineering (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Claims (10)

  1. Composition liquide isotrope adoucissante textile qui comprend :
    (i) de 30 à 50% en poids d'une matière adoucissante textile ; et
    (ii) de 5 à 40% en poids d'un acide organique.
  2. Composition selon la revendication 1, dont l'aspect est limpide.
  3. Composition selon la revendication 1 ou 2, dans laquelle la matière adoucissante textile comprend une matière cationique adoucissante textile.
  4. Composition selon une ou plusieurs des revendications précédentes, dans laquelle l'acide organique est un acide carboxylique ayant au total 8 atomes de carbone ou moins.
  5. Composition selon la revendication 4, dans laquelle l'acide organique contient au total 4 atomes de carbone ou moins.
  6. Composition selon la revendication 4, dans laquelle l'acide organique comprend l'acide propionique.
  7. Composition selon la revendication 4, dans laquelle l'acide comprend l'acide lactique ou l'acide acétique.
  8. Composition selon une ou plusieurs des revendications précédentes, qui comprend au moins 10% en poids d'acide organique.
  9. Composition selon l'une ou plusieurs des revendications précédentes, qui comprend au moins 20% en poids d'eau.
  10. Procédé de traitement du linge qui consiste à mettre en contact le linge avec une liqueur aqueuse comprenant de 0,01 à 2 g/l d'une composition selon l'une ou plusieurs des revendications précédentes.
EP90306600A 1989-06-19 1990-06-18 Composition adoucissante pour le linge Revoked EP0404471B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB8914054 1989-06-19
GB898914054A GB8914054D0 (en) 1989-06-19 1989-06-19 Fabric softening composition

Publications (2)

Publication Number Publication Date
EP0404471A1 EP0404471A1 (fr) 1990-12-27
EP0404471B1 true EP0404471B1 (fr) 1995-05-10

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EP90306600A Revoked EP0404471B1 (fr) 1989-06-19 1990-06-18 Composition adoucissante pour le linge

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EP (1) EP0404471B1 (fr)
JP (1) JP2562843B2 (fr)
KR (1) KR930008695B1 (fr)
AU (1) AU623019B2 (fr)
BR (1) BR9002886A (fr)
CA (1) CA2018789A1 (fr)
DE (1) DE69019236T2 (fr)
ES (1) ES2072981T3 (fr)
GB (1) GB8914054D0 (fr)
ZA (1) ZA904745B (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN108779417A (zh) * 2016-07-06 2018-11-09 汉高股份有限及两合公司 衣物干燥的加速

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8916306D0 (en) * 1989-07-17 1989-08-31 Unilever Plc Fabric softening composition
WO1992019714A1 (fr) * 1991-04-30 1992-11-12 The Procter & Gamble Company Produits assouplissants contenant de l'imidazoline substituee et des composes fortement ethoxyles
WO1993019156A1 (fr) * 1992-03-16 1993-09-30 The Procter & Gamble Company Procede de preparation de compositions de produit assouplissant concentre a base d'imidazoline
ATE245689T1 (de) * 1992-05-12 2003-08-15 Procter & Gamble Konzentrierte gewebeweichmacherzusammensetzungen mit biologisch abbaubaren gewebeweichmachern
WO1994004643A1 (fr) * 1992-08-21 1994-03-03 Colgate-Palmolive Company Assouplisseur de tissus pour le cycle de rinçage
DE4229649A1 (de) * 1992-09-04 1994-03-10 Henkel Kgaa Wäßrige Textilweichmacher-Dispersionen
PT687291E (pt) * 1993-03-01 2000-09-29 Procter & Gamble Composicoes concentradas e biodegradaveis amaciadoras de texteis a base de amonio quaternario e compostos contendo cadeias de acido gordo insaturado possuindo um valor de iodo intermedio
US5750491A (en) * 1993-08-02 1998-05-12 The Procter & Gamble Company Super concentrate emulsions with fabric actives
DE69406797T2 (de) * 1993-08-06 1998-06-10 The Procter & Gamble Co., Cincinnati, Ohio Trocken-aktivierte gewebekonditionierungs- und antistatische zusammensetzungen die biologisch abbaubare, ungesättigte verbindungen enthalten
US6559117B1 (en) 1993-12-13 2003-05-06 The Procter & Gamble Company Viscosity stable concentrated liquid fabric softener compositions
US5399272A (en) * 1993-12-17 1995-03-21 The Procter & Gamble Company Clear or translucent, concentrated biodgradable quaternary ammonium fabric softener compositions
US5427697A (en) * 1993-12-17 1995-06-27 The Procter & Gamble Company Clear or translucent, concentrated fabric softener compositions
SK284220B6 (en) * 1994-04-07 2004-11-03 Unilever Nv Fabric softening composition
GB9406824D0 (en) * 1994-04-07 1994-06-01 Unilever Plc Fabric softening composition
DE4439570A1 (de) * 1994-11-05 1996-05-09 Henkel Kgaa Wäschenachbehandlungsmittel
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CA2438655A1 (fr) * 1995-07-11 1997-01-30 Errol Hoffman Wahl Composition d'adoucisseur de tissus stable et concentre ayant une faible teneur en solvant organique
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CN108779417B (zh) * 2016-07-06 2021-10-29 汉高股份有限及两合公司 衣物干燥的加速

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AU5711990A (en) 1990-12-20
ES2072981T3 (es) 1995-08-01
ZA904745B (en) 1992-02-26
DE69019236T2 (de) 1995-10-05
KR910001155A (ko) 1991-01-30
DE69019236D1 (de) 1995-06-14
GB8914054D0 (en) 1989-08-09
JP2562843B2 (ja) 1996-12-11
BR9002886A (pt) 1991-08-20
EP0404471A1 (fr) 1990-12-27
JPH0327180A (ja) 1991-02-05
CA2018789A1 (fr) 1990-12-19
AU623019B2 (en) 1992-04-30
KR930008695B1 (ko) 1993-09-13

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