EP0059502B1 - Textile treatment compositions - Google Patents

Textile treatment compositions Download PDF

Info

Publication number
EP0059502B1
EP0059502B1 EP82200194A EP82200194A EP0059502B1 EP 0059502 B1 EP0059502 B1 EP 0059502B1 EP 82200194 A EP82200194 A EP 82200194A EP 82200194 A EP82200194 A EP 82200194A EP 0059502 B1 EP0059502 B1 EP 0059502B1
Authority
EP
European Patent Office
Prior art keywords
composition
weight
fabric softener
general formula
alkyl
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.)
Expired
Application number
EP82200194A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0059502A1 (en
Inventor
John Christopher Turner
Anthony Dovey
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.)
Procter and Gamble Ltd
Procter and Gamble Co
Original Assignee
Procter and Gamble Ltd
Procter and Gamble Co
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 Procter and Gamble Ltd, Procter and Gamble Co filed Critical Procter and Gamble Ltd
Priority to AT82200194T priority Critical patent/ATE14027T1/de
Publication of EP0059502A1 publication Critical patent/EP0059502A1/en
Application granted granted Critical
Publication of EP0059502B1 publication Critical patent/EP0059502B1/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/001—Softening compositions
    • C11D3/0015—Softening compositions liquid
    • 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 present invention relates to textile treatment compositions.
  • it relates to aqueous compositions suitable for use in the rinse cycle of a textile laundering operation to provide softening/static control benefits, the compositions being characterised by excellent physical characteristics on storage.
  • rinse-added fabric softening compositions contain, as the active softening component, substantially water-insoluble cationic materials having two long alkyl chains. Typical of such materials are di-stearyl dimethyl ammonium chloride and imidazolinium compounds substituted with two stearyl groups.
  • cationic compounds are highly effective softeners when applied in a rinse solution, there are certain disadvantages associated with their use.
  • the cationic compounds having long alkyl chains are very sensitive to carry over of anionic detergent into the rinse.
  • carry over of anionic detergent tends to neutralize the softening effect because the anionic-cationic complex tends to precipitate out of solution.
  • certain cationic surfactant compounds are expensive and in short supply and it is therefore desirable, for commercial reasons, to provide softening compositions having a reduced amount of cationic surfactant compound.
  • GB-A-1550205 and GB-A-1550206 disclose the use of certain cationic surfactants for enhancing the deposition of fatty acid ester softening materials onto fabrics.
  • US-A-4233164 and EP-A-21476 disclose the use of a protonated di-poly-ethoxy monoalkylamine containing from 10 to 40 ethylenoxy groups for improving the freeze-thaw recovery of a fabric conditioning composition containing cationic fabric conditioner and a fatty acid ester.
  • EP-A-18039 and US-A-4,149,978 describe fabric softening compositions containing a hydrophobic adjunct and a water-soluble cationic surfactant, especially a polyethoxylated diammonium compound.
  • US ⁇ A ⁇ 3,974,076 relates to fabric softening compositions containing a polyethoxylated quaternary ammonium compound and a fatty alcohol.
  • the present invention thus provides textile treatment composition having improved softening characteristics, particularly under hard water wash/rinse conditions, and improved formulation viscosity characteristics under long term storage together with excellent phase stability characteristics.
  • the present invention provides an aqueous textile treatment composition
  • an aqueous textile treatment composition comprising from 2% to 11 % by weight of composition of an active mixture comprising from 1% to 10% by weight of composition of a substantially water-insoluble cationic fabric softener having the general formula I wherein R 1 and R 2 represent alkyl or alkenyl groups of from 12 to 24 carbon atoms; R 3 and R 4 represent hydrogen or alkyl, alkenyl or hydroxyalkyl groups containing from 1 to 4 carbon atoms; and X is an equivalent amount of a counterion; and from 0.5% to 5% of a substantially water-insoluble nonionic fabric softener selected from C l6- C 24 non-cyclic hydrocarbons and fatty acid esters, having a total of from 10 to 40 carbon atoms, characterized in that the active mixture additionally comprises from 0.1% to 2% by weight of composition of an alkoxylated ammonium surfactant having the general formula 11 wherein R s is a C16-C22
  • the textile treatment compositions contain from 2% to 8% by weight, more preferably from 2.5% to 6% by weight of the cationic fabric softener, from 0.4% to 1.5% by weight, more preferably from 0.5% to 1.2% by weight of the alkoxylated ammonium surfactant, and from 1% to 3% by weight, more preferably from 1% to 2% by weight of the nonionic fabric softener.
  • These levels of active materials are preferred from the viewpoint of obtaining optimal product viscosity and stability characteristics.
  • the alkoxylated ammonium surfactant component herein has the general formula II wherein R 5 is a C 167 -C 22 alkyl or alkenyl group, n is 2 and x, y are each a number average in the range from 0 to 6, preferably 0 to 3, and the sum total of x and y is in the range from 1 to 6, preferably 1 to 3 and wherein X is as defined above.
  • R 5 is a C 167 -C 22 alkyl or alkenyl group
  • n is 2 and x
  • y are each a number average in the range from 0 to 6, preferably 0 to 3, and the sum total of x and y is in the range from 1 to 6, preferably 1 to 3 and wherein X is as defined above.
  • x, y each represent the weight averaged number of moles of alkylene oxide in the corresponding polyoxyalkylene moiety of the surfactant.
  • the alkoxylated ammonium surfactant may be present in the composition in partially deprotonated form. In such cases, all weight percentages and ratios herein are expressed in terms of the corresponding fully protonated salt.
  • compositions of the invention are generally formulated so as to have a slightly acidic pH, preferably from about 3.5 to 7, more preferably from about 4 to 6; moreover, it is desirable that the final formulation pH be lower than the acidity constant (pK a ) of the amine so that the amine exists predominantly in the form of its protonated or ammonium derivative.
  • the compositions take the form of a particulate dispersion of the cationic and nonionic fabric softeners in an aqueous continuum containing at least some of the alkoxylated ammonium surfactant.
  • a highly preferred composition comprises:
  • the nonionic fabric softener materials herein are C IO -C 24 non-cyclic hydrocarbons and fatty acid esters having a total of 10 to 40 carbon atoms.
  • a particularly preferred material is glyceryl monostearate.
  • the present invention also provides a method of making the textile treatment compositions generally described above by the steps of:
  • compositions of the invention preferably are stable to separation in a centrifuge at 3000 r.p.min for 16 hours and have a dynamic viscosity in the range from about (0.35 Pa.s) (350 cp) to about (0.07 Pa.s) (70 cp), preferably from about (0.2 Pa.s) (200 cp) to about (0.1 Pa.s) (100 cp) measured in a Brookfield (RTM) Viscometer, using Spindle No. 2 at 60 r.p.min and at 21°C.
  • RVTM Brookfield
  • the water-insoluble cationic fabric softener is preferably a fabric-substantive cationic compound which, in pure form as a strong acid salt (e.g. chloride), has a solubility in distilled water at pH 2.5 and 20°C of less than 1 g/l, or can be a mixture of such compounds.
  • the soluble fraction of the surfactant is taken to be that material which cannot be separated from water by centrifugal action and which passes a 100 nm Nucleopore filter (Registered Trade Mark).
  • the cationic softener desirably has a monomer solubility (as measured by critical micelle concentration or C.M.C.) such that the C.M.C. of the material under the conditions defined above is less than about 50 p.p.min, preferably less than about 20 p.p.min.
  • Literature C.M.C. values are taken where possible, especially surface tension, conductimetric or dye adsorption values.
  • the substantially water-insoluble cationic fabric softeners are the quaternary ammonium and amine salt compounds having the formula:-
  • R 1 and R 2 represent alkyl or alkenyl groups of from 12 to 24 carbon atoms
  • R 3 and R 4 represent hydrogen, alkyl, alkenyl or hydroxyalkyl groups containing from 1 to 4 carbon atoms
  • X is the salt counteranion, preferably selected from halide, methyl sulfate, ethyl sulfate, benzoate, acetate, propionate and phosphate radicals.
  • Representative -examples of these quaternary softeners include ditallow dimethyl ammonium chloride; ditallow dimethyl ammonium methyl sulfate; dihexadecyl dimethyl ammonium chloride; di(hydrogenated tallow alkyl) dimethyl ammonium chloride; dioctadecyl dimethyl ammonium chloride, dieicosyl dimethyl anionic chloride, didocosyl dimethyl ammonium chloride; di(hydrogenated tallow) - dimethyl ammonium methyl sulfate; dihexadecyl diethyl ammonium chloride; di(coconut alkyl) dimethyl ammonium chloride, and di(coconut alkyl) dimethyl ammonium methosulfate. Of these ditallow dimethyl ammonium chloride and di(hydrogenated tallow alkyl) dimethyl ammonium chloride are preferred.
  • alkoxylated ammonium surfactant component these are defined as protonated mono- or di-polyethoxy primary alkyl amines wherein the amine contains from 16 to 22 carbon atoms in the alkyl chain, and wherein the average number of ethoxy groups per polyethoxy chain is from 0 to 6, preferably from 0 to 3, and wherein the sum total of polyethoxy groups per molecule is from 1 to 6, preferably from 1 to 3.
  • Preferred water-insoluble nonionic fabric softeners of the fatty acid ester class are C, o -C 24 fatty acid esters of mono- or poly-hydroxy alcohols containing 1 to 12 carbon atoms.
  • the alcohol has from 1 to 8 carbon atoms, and the fatty acid ester has at least 1, more preferably at least 2, free (i.e., unesterfied) hydroxyl groups.
  • the mono or poly-hydric alcohol portion of the ester can be represented by methanol, isobutanol, 2-ethyl-hexanol, isopropanol, ethylene glycol and polyethylene glycol with a maximum of 5 ethylene glycol units, glycerol, diglycerol, polyglycerol, xylitol, erythritol, pentaerythritol, sorbitol or sorbitan, sugars such as glucose, fructose, galactose, mannose, xylose, arabinose, ribose, 2-deoxy-ribose, sedoheptulose and sucrose.
  • Ethylene glycol, glycerol, and sorbitan esters are particularly preferred, especially the monoesters of glycerol.
  • the fatty acid portion of the ester normally comprises a fatty acid having from 10 to 24 (preferably 12 to 22) carbon atoms, typical examples being lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, oleic acid and linoleic acid.
  • the glycerol esters are very highly preferred. These are the mono-, di- or tri-esters of glycerol and fatty acids of the class described above. Commercial glyceryl mono-stearate, which may contain a proportion of di- and tri-stearate, is suitable. Also useful are mixtures of saturated and unsaturated esters of glycerol derived from mixed saturated and unsaturated fatty acids.
  • nonionic fabric conditioning agents are the C 10 to C 24 fatty acid esters of sorbitan such as those described in US ⁇ A ⁇ 4,085,052.
  • Sorbitan mono- and di-esters of lauric, myristic, palmitic, stearic, arachidic or behenic, oleic or linoleic acids are particularly useful as softening agents and can also provide antistatic benefits.
  • Sorbitan esters are commercially available, for instance, under the trade name Span (RTM).
  • RTM trade name for the purpose of the present invention, it is preferred that a significant amount of di- and tri-sorbitan esters are present in the ester mixture. Ester mixtures having from 20%-50% mono-ester, 25%-50% di-ester and 10%-35% of tri- and tetra-esters are preferred.
  • Preferred nonionic fabric softeners of the hydrocarbon class are paraffins or olefins containing from 14 to 22 carbon atoms.
  • Materials known generally as paraffin oil, soft paraffin wax and petrolatum are especially suitable. Examples of specific materials are tetradecane, hexadecane, octadecane and octadecene.
  • Preferred commercially-available paraffin mixtures include spindle oil and light oil, technical grade mixtures of C 14 /C 17 n-paraffins and C 18 /C 20 n-paraffins and refined white oil.
  • the present compositions can be supplemented by all manner of optional components conventionally used in textile treatment compositions, for example, colorants, perfumes, preservatives, optical brighteners, opacifiers, pH buffers, viscosity modifiers, fabric conditioning agents, surfactants, stabilizers, such as guar gum and polyethylene glycol, anti-shrinkage agents, anti-wrinkle agents, fabric crisping agents, nonionic softening agents, spotting agents, soil- release agents, germicides, fungicides, antioxidants such as butylated hydroxy toluene, anti-corrosion agents etc.
  • the level of these optional ingredients should, if necessary, be controlled so as not to deleteriously effect the physical stability and viscosity characteristics of the product.
  • Another optional ingredient is a water-soluble non-alkoxylated quaternary ammonium surfactant having the general formula III wherein Rg represents a C 8 -C 24 alkyl or alkenyl group, and R io , R 11 , R 12 independently represent a C 1- C 4 alkyl or alkenyl group or an aryl group and wherein X is as defined earlier.
  • Suitable materials of this general type include the tallow trimethyl ammonium salts, cetyl trimethyl ammonium salts, myristyl trimethyl ammonium salts and coconutalkyl trimethyl ammonium salts.
  • compositions may contain other textile treatment or conditioning agents.
  • agents include silicones, as for example described in DE-A-2631 419.
  • the optional silicone component can be used in an amount of from 0.1 % to 6%, preferably from 0.2% to 2% of the softener composition.
  • Another optional ingredient of the present compositions is a water-soluble cationic polymer having a molecular weight in the range from 2000 to 250,000, preferably from 5000 to 150,000 and containing an average of from 100 to 1000, preferably from about 150 to 700 monomer units per molecule.
  • Molecular weights are specified as viscosity average molecular weights and can be determined as described in F. Daniels et al Experimental Physical Chemistry, pp. 71-74, 242-246, McGraw-Hill (1949), at 25°C using an Ostwald viscometer.
  • the polymers are preferably soluble in distilled water to the extent of 0.5% by weight at 20°C.
  • Suitable polymers of this type include polyethyleneimine having an average molecular weight of from 10,000 to 35,000, ethoxylated polyethyleneimine wherein the weight ratio of polyethyleneimine to ethyleneoxide is at least 1:1 and wherein the molecular weight is from 20,000 to 70,000, and quaternised polyethyleneimines sold under the Trade Name Alcostat (RTM) by Allied Colloids.
  • Suitable preservatives for use in the present compositions include 2-nitro-2-bromo-propane-1,3-diol, glutaraldehyde and 2-methyl-4-isothiazolin-3-one and its 5-chloro derivative.
  • the textile treatment compositions of the invention can be used by adding to the rinse cycle of a conventional home laundry operation.
  • rinse water has a temperature of from 5°C to 60°C.
  • concentration of the total active ingredients is generally from 2 ppm to 1000 ppm, preferably from 10 ppm to 500 ppm, by weight of the aqueous rinsing bath.
  • Aqueous textile treatment compositions are prepared having the following formulae:-
  • compositions are prepared by forming a molten premix of the water-insoluble cationic and nonionic fabric softeners and alkoxylated ammonium surfactants, and where present, silicone and non-alkoxylated water-soluble surfactant, at a temperature of about 65°C.
  • the molten premix is then injected into a water seat containing minor ingredients, apart from perfume, held at about 45°C and this is stirred for about 5 minutes. Thereafter, the dispersion is passed through a heat exchanger to bring the temperature down to about 25°C and finally perfume is added.
  • the products thus prepared are stable dispersions displaying excellent viscosity characteristics at both low and high temperatures over prolonged periods of storage; they deliver excellent softening and antistatic performance across the range of natural and synthetic fabrics in both hard and soft water and they also display excellent dispensing and dissolving characteristics in cold rinse water.

Landscapes

  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Textile Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Processes Of Treating Macromolecular Substances (AREA)
EP82200194A 1981-02-28 1982-02-18 Textile treatment compositions Expired EP0059502B1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT82200194T ATE14027T1 (de) 1981-02-28 1982-02-18 Textilbehandlungszusammenstellungen.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB8106418 1981-02-28
GB8106418 1981-02-28

Publications (2)

Publication Number Publication Date
EP0059502A1 EP0059502A1 (en) 1982-09-08
EP0059502B1 true EP0059502B1 (en) 1985-06-26

Family

ID=10520058

Family Applications (1)

Application Number Title Priority Date Filing Date
EP82200194A Expired EP0059502B1 (en) 1981-02-28 1982-02-18 Textile treatment compositions

Country Status (8)

Country Link
EP (1) EP0059502B1 (enrdf_load_html_response)
JP (1) JPS57205580A (enrdf_load_html_response)
AT (1) ATE14027T1 (enrdf_load_html_response)
CA (1) CA1206705A (enrdf_load_html_response)
DE (1) DE3264359D1 (enrdf_load_html_response)
ES (1) ES509979A0 (enrdf_load_html_response)
GR (1) GR75151B (enrdf_load_html_response)
IE (1) IE52564B1 (enrdf_load_html_response)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4454049A (en) * 1981-11-14 1984-06-12 The Procter & Gamble Company Textile treatment compositions
DE3204165A1 (de) * 1982-02-06 1983-08-11 Hoechst Ag, 6230 Frankfurt Konzentrierte waescheweichspuelmittel
DE3218667A1 (de) * 1982-05-18 1983-11-24 Hoechst Ag, 6230 Frankfurt Konzentrierte waescheweichspuelmittel
NZ207932A (en) * 1983-05-11 1986-03-14 Colgate Palmolive Co Fabric softener compositions containing quaternary ammonium compounds
GB8410321D0 (en) * 1984-04-19 1984-05-31 Unilever Plc Aqueous concentrated fabric softening composition
GB8410320D0 (en) * 1984-04-19 1984-05-31 Unilever Plc Aqueous fabric softening composition
JP2522659B2 (ja) * 1987-03-31 1996-08-07 ライオン株式会社 柔軟剤組成物
DE3877422T2 (de) 1987-05-01 1993-05-13 Procter & Gamble Quaternaere isopropylesterammonium-verbindungen als faser- und gewebebehandlungsmittel.
ATE105331T1 (de) * 1987-06-16 1994-05-15 Cotelle Sa Konzentrierte weichmacher.
GB8722540D0 (en) * 1987-09-24 1987-10-28 Unilever Plc Composition for softening fabrics
GB8827697D0 (en) * 1988-11-28 1988-12-29 Unilever Plc Fabric-treatment composition
EP0990695A1 (de) * 1998-09-30 2000-04-05 Witco Surfactants GmbH Weichspülmittel mit farberhaltender Wirkung
GB0014891D0 (en) 2000-06-16 2000-08-09 Unilever Plc Fabric softening compositions
ES2309593T3 (es) * 2003-10-16 2008-12-16 THE PROCTER & GAMBLE COMPANY Composiciones acuosas que comprenden vesiculas que tienen cierta permeabilidad de vesicula.
WO2011119796A1 (en) * 2010-03-26 2011-09-29 The Procter & Gamble Company Methods of making fabric softener

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3974076A (en) * 1974-01-11 1976-08-10 The Procter & Gamble Company Fabric softener

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3959157A (en) * 1973-06-04 1976-05-25 Colgate-Palmolive Company Non-phosphate detergent-softening compositions
GB1601360A (en) * 1977-07-12 1981-10-28 Procter & Gamble Textile treatment composition
EP0018039B2 (en) * 1979-04-21 1988-08-24 THE PROCTER & GAMBLE COMPANY Fabric softening composition
US4233164A (en) * 1979-06-05 1980-11-11 The Proctor & Gamble Company Liquid fabric softener

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3974076A (en) * 1974-01-11 1976-08-10 The Procter & Gamble Company Fabric softener

Also Published As

Publication number Publication date
IE52564B1 (en) 1987-12-09
EP0059502A1 (en) 1982-09-08
GR75151B (enrdf_load_html_response) 1984-07-13
JPS57205580A (en) 1982-12-16
ES8303517A1 (es) 1983-02-01
ES509979A0 (es) 1983-02-01
IE820426L (en) 1982-08-28
CA1206705A (en) 1986-07-02
ATE14027T1 (de) 1985-07-15
DE3264359D1 (en) 1985-08-01
JPH0215664B2 (enrdf_load_html_response) 1990-04-12

Similar Documents

Publication Publication Date Title
EP0060003B1 (en) Textile treatment compositions and preparation thereof
EP0056695B2 (en) Textile treatment compositions
US5066414A (en) Stable biodegradable fabric softening compositions containing linear alkoxylated alcohols
EP0309052B1 (en) Stable biodegradable fabric softening compositions containing linear alkoxylated alcohols
US4789491A (en) Method for preparing biodegradable fabric softening compositions
US4386000A (en) Fabric softening composition
EP0021476B1 (en) Liquid fabric softener containing a quaternary ammonium salt and method of conditioning fabrics
EP0018039B2 (en) Fabric softening composition
US6004913A (en) High di(alkyl fatty ester) quaternary ammonium compound in esteramine from triethanolamine
US4126562A (en) Textile treatment compositions
EP0059502B1 (en) Textile treatment compositions
US5093014A (en) Fabric treatment composition and the preparation thereof
EP0507478B1 (en) Fabric softening composition
EP0293953B1 (en) Quaternary mono-ester ammonium compounds as fibre and fabric treatment compositions
US5409621A (en) Fabric softening composition
EP0032267A1 (en) Concentrated textile treatment compositions and method for preparing them
EP0295739A2 (en) Method for preparing biodegradable fabric treatment compositions
CA1232414A (en) Aqueous fabric softening composition
JPH08505905A (ja) 繊維製品柔軟化組成物
EP0803283B1 (en) Cationic compositions containing hydroxyester
EP0159919A2 (en) Aqueous concentrated fabric softening composition
EP0159196A2 (en) Aqueous concentrated fabric softening composition
CA1192003A (en) Fabric softening composition

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Designated state(s): AT BE CH DE FR GB IT NL

17P Request for examination filed

Effective date: 19830224

ITF It: translation for a ep patent filed
GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Designated state(s): AT BE CH DE FR GB IT LI NL

REF Corresponds to:

Ref document number: 14027

Country of ref document: AT

Date of ref document: 19850715

Kind code of ref document: T

REF Corresponds to:

Ref document number: 3264359

Country of ref document: DE

Date of ref document: 19850801

ET Fr: translation filed
PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT

26N No opposition filed
ITTA It: last paid annual fee
PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 19940210

Year of fee payment: 13

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: AT

Payment date: 19940214

Year of fee payment: 13

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: CH

Payment date: 19940215

Year of fee payment: 13

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 19940228

Year of fee payment: 13

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: BE

Payment date: 19940408

Year of fee payment: 13

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: AT

Effective date: 19950218

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: LI

Effective date: 19950228

Ref country code: CH

Effective date: 19950228

Ref country code: BE

Effective date: 19950228

BERE Be: lapsed

Owner name: THE PROCTER & GAMBLE CY

Effective date: 19950228

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Effective date: 19950901

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Effective date: 19951031

NLV4 Nl: lapsed or anulled due to non-payment of the annual fee

Effective date: 19950901

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: GB

Payment date: 19960209

Year of fee payment: 15

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 19960227

Year of fee payment: 15

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Effective date: 19970218

GBPC Gb: european patent ceased through non-payment of renewal fee

Effective date: 19970218

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Effective date: 19971101