EP0052517A1 - Compositions concentrées d'adoucissants textiles - Google Patents

Compositions concentrées d'adoucissants textiles Download PDF

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Publication number
EP0052517A1
EP0052517A1 EP81305438A EP81305438A EP0052517A1 EP 0052517 A1 EP0052517 A1 EP 0052517A1 EP 81305438 A EP81305438 A EP 81305438A EP 81305438 A EP81305438 A EP 81305438A EP 0052517 A1 EP0052517 A1 EP 0052517A1
Authority
EP
European Patent Office
Prior art keywords
group
methylsulfate
alkyl
component
halide
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.)
Granted
Application number
EP81305438A
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German (de)
English (en)
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EP0052517B1 (fr
Inventor
Michael Eugene Burns
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Procter and Gamble Co
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Procter and Gamble Co
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Publication date
Application filed by Procter and Gamble Co filed Critical Procter and Gamble Co
Priority to AT81305438T priority Critical patent/ATE12947T1/de
Publication of EP0052517A1 publication Critical patent/EP0052517A1/fr
Application granted granted Critical
Publication of EP0052517B1 publication Critical patent/EP0052517B1/fr
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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
    • C11D1/38Cationic compounds
    • C11D1/645Mixtures of compounds all of which are cationic
    • 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
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating 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
    • D06M13/46Compounds containing quaternary nitrogen atoms

Definitions

  • This invention relates to fabric softening compositions and, in particular, to'compositions in aqueous medium which contain a relatively high proportion of cationic fabric softening ingredients.
  • Conventional rinse-added fabric softening compositions contain fabric softening agents which are substantially water-insoluble cationic materials usually having two long alkyl chains. Typical of such materials are distearyl dimethyl ammonium chloride and imidazolinium compounds substituted with two stearyl groups. These materials are normally prepared in the form of an aqueous dispersion or emulsion, and it is generally not possible to prepare such aqueous dispersions with more than about 6% of cationic materials without taking special precautions to ensure acceptable viscosity and stability characteristics. Indeed, with cationic levels in excess of about 8% the problems of physical instability and high viscosity become, in the case of . conventional fabric softening products, almost intractable. The formulation of fabric softener compositons with low levels of the active softener ingredients adds substantially to distribution and packaging costs.
  • a more concentrated fabric softening composition in addition to shipping and packaging economy, another advantage of a more concentrated fabric softening composition is that it permits the consumer to exercise choice in the type of performance desired, in that the concentrated product can either be used as such or can be diluted to a conventional concentration before use. This opens up the possibility of supplying the concentrated fabric softening composition in a more economically packaged form intended for making up by the consumer into a conventional bottle.
  • Paraffins are not essential components of the compositions of the present invention and are preferably absent therefrom.
  • Dutch Patent Application No. 6706178 relates to viscosity control in fabric softening compositions with up to 12% of cationic softener, and suggests the use of low molecular weight hydrocarbons for this purpose.
  • European Patent Application 0013780 discloses concentrated aqueous fabric softener compositions comprising a cationic softener and a viscosity control agent selected from the group consisting of hydrocarbons, fatty acids, fatty acid esters and fatty alcohols.
  • European Patent Application 0018039 published October 29, 1980, discloses concentrated aqueous fabric softening compositions comprising an insoluble cationic softener, a water-soluble nonionic or cationic surfactant and a hydrophobic adjunct selected from C 12 to'C20 paraffins and esters of C 12 to C 24 fatty acids and C 1 to C a fatty alcohols.
  • Water-insoluble fatty nonionic materials are not essential to the compositions herein and are preferably absent therefrom.
  • the object of the present invention is to provide'highly concentrated aqueous fabric softening compositions, based on cationic softener systems, which do not require substantial quantities of materials other than the cationic softeners to ensure physical stability and acceptable viscosity.
  • the invention relates to highly concentrated aqueous liquid fabric softener compositions which comprise a mixture of specific types of cationic softeners and an ionizable salt, wherein the mixture of cationic softeners has an Iodine Value of at least about 4.2.
  • compositions which contain in the order of 15% to 22.5% cationic softener ingredients.
  • the present invention is directed to concentrated aqueous fabric softener compositions which are pourable at 40°F, the said compositions comprising:
  • compositions of the invention are stable and pourable at normally encountered temperatures (40°-100°F) and are easily dispersible in water.
  • "pourable” means having a viscosity below about 5000 cP as measured by a B rookfield Synchro-lectric Viscometer with Spindle #4 at 60 rpm.
  • the compositions provide excellent fabric softening and antistatic performance in laundry rinse solutions containing from about 25 ppm to about 90 ppm of the combination of Components A, B and C.
  • the mono nitrogen quaternary ammonium salt softener of the compositions herein has'the structure: wherein R 1 and R 2 can be the same or different from each other and are selected from the group consisting of C 14 to C 20 alkyl and alkenyl groups and R 3 and R 4 are the same or different from each other and are selected from the group consisting of C1 to C 3 alkyls, or -(C n H 2n O) x H wherein n is 2 or 3, x is from 1 to about 3, and wherein X is halide, methylsulfate or ethylsulfate. It is preferred that X be halide, and the preferred halides are chloride and bromide.
  • R 1 and R 2 be alkyl, i.e., it is preferred that the unsaturation in the cationic active system come from Components B or C, or mixtures thereof.
  • Exemplary compounds are dimyristyldimethyl ammonium chloride, dipalmityldiethyl ammonium bromide, distearyldimethyl ammonium chloride, distearyldimethyl ammonium bromide, distearyldiisopropyl ammonium bromide, diar- achidyldimethyl ammonium chloride, distearyl-2-hydroxypropylmethyl ammonium chloride, oleylstearyldimethyl ammonium ethylsulfate and distearyl-2-hydroxyethylmethyl ammonium methylsulfate.
  • the R 1 and R 2 grbups are derived from tallow and the R 3 and R 4 groups are methyl.
  • the tallow can be hydrogenated or unhydrogenated. Hydrogenated (i.e., saturated) tallow is preferred, and halides are the preferred anions. Accordingly, preferred mono nitrogen quaternary ammonium salt softener compounds herein are dihydrogenatedtallowdimethyl ammonium chloride and dihydrogenatedtallowdimethyl ammonium bromide. Hydrogenated tallow often has some residual degree of unsaturation such that the Iodine Value of hydrogenated ditallowdimethyl ammonium salts can be up to about 5.
  • Exemplary commercial quaternary ammonium salts which are suitable for use as Component A in the compositions herein are dihydrogenatedtallowdimethyl ammonium chloride sold under the name Adogen 442, and ditallowdimethyl ammonium chloride (I.V. about 20-30) sold under the name Adogen 470, both from Sherex Chemical Company.
  • the quaternary ammonium salts are used in the compositions herein at levels of from about 2% to about 11%, preferably from about 5% to about 10%. (All percentages and proportions herein are "by weight” unless specified otherwise).
  • the di(2-amidoethyl) methyl quaternary ammonium salt of the invention herein has the structure wherein R 5 and R 6 are the same or different from each other and are selected from the group consisting of C 14 to C 20 alkyl and alkenyl groups, wherein R7is selected from H, methyl, ethyl and -(C n H 2n O) x H wherein n is 2 to 3 and x is from 1 to about 5 (preferably 3), and wherein X is an anion selected from halide, ethylsulfate or methylsulfate.
  • R 5 and R 6 are alkyl and R 7 is -(C n H 2n O) x H.
  • Exemplary compounds are di(2-hydrogenated- tallowamidoethyl) ethoxylated (2 ethoxy groups) methyl ammonium methylsulfate, di(2-hydrogenatedtallowamido- ethyl) dimethyl ammonium ethylsulfate, di(2-palmityl- amidoethyl) hydromethyl ammonium chloride, di(2-oleyl- amidoethyl) propoxylated (3 propoxy groups) methyl ammonium bromide, di(2-palmitoleylamidoethyl) dimethyl ammonium ethylsulfate and di(2-stearylamidoethyl) propoxylated (2 propoxy groups) methyl ammonium methylsulfate.
  • Exemplary commercial materials suitable for use as Component B herein are di(2-hydrogenatedtallow- amidoethyl) ethoxylated methyl ammonium methylsulfate sold under the name Varisoft 110, and di(2-tallowamido- ethyl) ethoxylated methyl ammonium methylsulfate (I.V. about 31) sold under the name Varisoft 222, both from Sherex Chemical Company.
  • Component C which is present at a level of from about 2% to about 13% (preferably from about 3% to about 10%) of the compositions of the present invention is a cationic softener selected from a group consisting of three different types of imidazolinium salts. These Component C materials are designated herein as C.(l), C .(2) and C. (3).
  • Component C.(l) has the formula: wherein R 8 and R 9 are the same or different from each other and are selected from the group consisting of C 14 to C 20 alkyl and alkenyl groups, wherein X is halide, ethylsulfate or methylsulfate.
  • R 8 and R 9 are a mixture of alkyl and alkenyl groups such that Component C.(l) has an I.V. of from about 25 to about 125, more preferably from about 25 to about 45.
  • Exemplary compounds of this type are: 1-methyl- l-tallowamidoethyl-2-tallowimidazolinium methylsulfate, 1-methyl-1-oleylamidoethyl-2-oleylimidazoliniuin chloride, l-methyl-l-palmitoleylamidoethyl-2-palmitoleylimidazo- linium ethylsulfate, 1-methyl-1-soyaamidoethyl-2-soya- imidazolinium methylsulfate and 1-methyl-l-hydrogenated- tallowamidoethyl-2-hydrogenatedtallowimidazolinium methylsulfate.
  • Exemplary commercial materials are 1-methyl-l-tallowamidoethyl-2-tallowimidazolinium methylsulfate (I.V. about 42) sold under the name Varisoft 475, and 1-methyl-1-hydrogenatedtallowamidoethyl-2-hydrogenatedtallowimidazolinium methylsulfate sold under the name Varisoft 445, both available from Sherex Chemical Company.
  • Component C.(2) has the formula: mixture of alkenyl and alkyl groups such that the compound has an I.V. of from about 25 to about 125.
  • Preferably Components A and B will be saturated compounds and the weight ratio of Component C to Components A + B will be at least about 0.2:1 and the sum of Components A + B + C will be from about 15% to about 21%.
  • the cationic active system in the composition has an Iodine Value (I.V.) of at least about 4.2, i.e., a substantial amount of unsaturation must be present.
  • I.V. Iodine Value
  • the compositions will gel and become unusable at room temperature and below.
  • the I.V. is at least about 10.5 and is most preferably from about 10.5 to about 34.
  • the unsaturation can come from Component A, B or C, or any combination thereof.
  • I.V. is a direct measure of the unsaturation and is based upon the reaction of iodine with unsaturated bonds in a molecule.
  • the I.V. is defined as the number of decigrams of iodine which will react with one gram of the cationic active system.
  • the standard technique for determining I.V. is well known in the art. If one knows the I.V. of the individual components which are used in the active system, then the I.V. of the system can simply be calculated by multiplying the I.V. of each component by the percentage of that component in the composition and then dividing by the total percentage of components in the composition.
  • the I.V. of the cationic active system is 10 (i.e., 5 x 40 T 20).
  • R 10 and R 11 can be the same or different from each other and are selected from the group consisting of C 14 to C 20 alkyl and alkenyl and X is halide, methylsulfate or ethylsulfate.
  • Exemplary compounds of this type are: 1-ethylene bis(2-stearyl, 1-methyl, imidazolinium methylsulfate), 1-ethylene bis(2-oleyl, 1-methyl, imidazolinium methylsulfate) and 1-ethylene bis(2-tallow, 1-methyl, imidazolinium methylsulfate).
  • the tallow derivative, in hydrogenated or unhydrogenated form, is commercially available from Sherex Chemical Company under the name Varisoft 6112.
  • the unhydrogenated material has an I.V. of about 29.
  • Component C.(3) has the formula: wherein R 12 . R 13' and R 14 are the same or different from each other and are selected from the group consisting of C 14 to C 20 alkyl or alkenyl, wherein X - is halide, methylsulfate or ethylsulfate.
  • Exemplary compounds of this type are: 1-methyl-2-stearyl-3[(stearylamidoethyl-stearylamino)ethylene]imidazolinium ethylsulfate, l-methyl-2-oleyl-3[(oleylamido- ethyl-oleylamino)ethylene]imidazolinium ethylsulfate and 1-methyl-2-tallow-3[tallowamidoethyl-tallowamino) ethylene]imidazolinium ethylsulfate.
  • the tallow derivative (I.V. about 32) is sold under the name Varisoft 3012 by the Sherex Chemical Company.
  • Components C.(l), C.(2) and C.(3) can be used singly or in mixtures with each other.
  • Component C in the compositions herein is Component C.(1), wherein R 8 and R 9 are a
  • compositions of the invention wherein the total cationic level and the source and amount of unsaturation are varied are illustrated in the following table.
  • ionizable salts can be used as Component D in the compositions herein.
  • the particular salt should be sufficiently soluble in the compositions to produce a concentration in solution of from about 500 to about 6000 ppm (preferably about 500 to about 4000 ppm)and should not adversely interact with the fabric softener compounds.
  • suitable salts are the halides of the Group lA and 2A metals of the Periodic Table of Elements, e.g., sodium chloride, potassium bromide, lithium chloride, calcium chloride and magnesium chloride.
  • the ionizable salts provide viscosity control, particularly during the process of mixing the ingredients to make the compositions herein.
  • the water used in the compositions herein is preferably distilled or deionized water and is generally present at levels of from about 76% to 84%.
  • compositions of the invention are those wherein Components A and B are substantially saturated and Component C is unsaturated and is of the type identified herein as C.(l). These preferred compositions can be defined as follows.
  • compositions herein Various optional materials such as are ordinarily used in fabric softening compositions can be used in the compositions herein. These include, for example, perfumes at 0.1% to 1.0%, antimicrobials at 0.01% to 0.1% and dyes at 0.001% to 0.01%.
  • the softening ingredients are normally sold to the formulator in the form of 70% to 90% pastes in which a lower alcohol is a diluent. It has been found that the compositions herein should preferably be substantially free of lower aliphatic alcohols, and that in any event these alcohols should not be present in said compositions at levels in excess of about 3%.
  • the softener ingredients are purchased as dispersions in amounts of alcohol which would produce alcohol levels in excess of about 3% in the finished compositions herein, some or all of the alcohol should be removed (e.g., by heat- assisted evaporation) before use in preparing the compositions herein.
  • Lower alcohols tend to cause viscosity increase during storage (particularly at higher storage temperatures) and if the alcohol is isopropanol, the odor imparted to the finished product. is undesirable.
  • freeze-thaw recovery agents are the di-polyetboxy monoalkyl amines of the formula wherein R 19 is an alkyl or alkenyl group of from about 14 to 20 carbon atoms and the sum of m + n is from about 10 to about 25.
  • a preferred material is sold under the name Varonic T220 by Sherex Chemical Company wherein R 19 is unhydrogenated tallow and the sum of m + n is about 20.
  • Freeze-thaw agents are used in the compositions herein at levels of about 1%.
  • a particularly preferred method of preparation is as follows. Components A, B and C (and dyes, if used) are heated and blended together to form a melt at about 175-185°F. This melt is then added gradually to 110°F water with vigorous agitation. A portion of the ionizable salt is added to the water concurrently with the melted softeners at a rate necessary to keep the aqueous mix fluid and stirrable. Upon completion of the addition of the melted softeners, the remainder of the ionizable salt is added to produce the desired viscosity.
  • Optional ingredients such as perfume, etc., are added after the viscosity of the mix has been reduced by the addition of most of the ionizable salt. After completion of the addition of ionizable salt the composition is cooled to room temperature before filling into containers.
  • compositions herein have a pH of from about 5.5 to about 6.5.
  • Acids such as hydrochloric, sulfuric or citric or bases such as sodium hydroxide or sodium carbonate can be added, as needed, to the compositions to achieve the desired pH. Normally, only very small amounts of such p H adjusting agents are required.
  • the Iodine Value of the total cationic active system was 10.5.
  • This composition exhibits excellent softening and antistatic performance and has excellent physical stability and pourability between 40°F and 100°F.
  • Another formula which exhibits comparable performance, physical stability and pourability is made as above except that the active system consists of 5% dihydrogenatedtallowdimethyl ammonium chloride, 10% di(2-hydrogenatedtallowamidoethyl) ethoxylated methyl,ammonium methylsulfate and 5% 1-methyl- l-tallowamidoethyl-2-tallbwimidazolinium methylsulfate (Varisoft 475).
  • This formula also has an Iodine Value of 10.5 for the total cationic active system.

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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)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)
EP81305438A 1980-11-18 1981-11-17 Compositions concentrées d'adoucissants textiles Expired EP0052517B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AT81305438T ATE12947T1 (de) 1980-11-18 1981-11-17 Konzentrierte textilweichmacherzusammensetzungen.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US20786280A 1980-11-18 1980-11-18
US207862 1998-12-08

Publications (2)

Publication Number Publication Date
EP0052517A1 true EP0052517A1 (fr) 1982-05-26
EP0052517B1 EP0052517B1 (fr) 1985-04-24

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EP81305438A Expired EP0052517B1 (fr) 1980-11-18 1981-11-17 Compositions concentrées d'adoucissants textiles

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EP (1) EP0052517B1 (fr)
JP (1) JPS57154463A (fr)
AT (1) ATE12947T1 (fr)
AU (1) AU544660B2 (fr)
DE (1) DE3170187D1 (fr)
MX (1) MX157118A (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0079643A2 (fr) * 1981-11-17 1983-05-25 THE PROCTER & GAMBLE COMPANY Compositions adoucissantes concentrées pour matières textiles
EP0275694A1 (fr) * 1986-12-24 1988-07-27 Unilever Plc Composition adoucissante liquide pour le tissu
EP0373696A2 (fr) * 1988-12-15 1990-06-20 The Procter & Gamble Company Adoucissant textile liquide
WO1993001265A1 (fr) 1991-07-05 1993-01-21 Unilever Plc Composition adoucissante pour tissus
WO1993016157A1 (fr) * 1992-02-07 1993-08-19 Henkel Kommanditgeselschaft Auf Aktien Procede de fabrication de concentres aqueux, de faible viscosite, d'esters quaternises
US5433869A (en) * 1992-12-22 1995-07-18 Colgate-Palmolive Co. Liquid fabric conditioning composition containing amidoamine softening compound
US5474690A (en) * 1994-11-14 1995-12-12 The Procter & Gamble Company Concentrated biodegradable quaternary ammonium fabric softener compositions containing intermediate iodine value fatty acid chains
US5545340A (en) * 1993-03-01 1996-08-13 The Procter & Gamble Company Concentrated biodegradable quaternary ammonium fabric softener compositions and compounds containing intermediate iodine value unsaturated fatty acid chains
EP0768369A1 (fr) * 1995-10-11 1997-04-16 The Procter & Gamble Company Compositions adoucissantes
EP0734433B1 (fr) * 1993-12-13 2000-03-22 The Procter & Gamble Company Compositions assouplissantes concentrees liquides, de viscosite stable

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU620785B3 (en) * 1990-04-26 1992-01-09 D.T.A. Pty Ltd Transmission sleeve for a down hole hammer
US6630441B2 (en) * 1997-07-29 2003-10-07 The Procter & Gamble Company Concentrated, stable, preferably clear, fabric softening composition containing amine fabric softener
EP2553068A1 (fr) * 2010-03-26 2013-02-06 The Procter & Gamble Company Procédés de production de produit assouplissant
JP7145741B2 (ja) * 2018-11-30 2022-10-03 花王株式会社 繊維製品の処理方法
JP7145787B2 (ja) * 2019-02-25 2022-10-03 花王株式会社 繊維製品の処理方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3681241A (en) * 1968-03-04 1972-08-01 Lever Brothers Ltd Fabric softening

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3583912A (en) * 1968-01-29 1971-06-08 Cpc International Inc Detergent compatible fabric softener
US3933871A (en) * 1973-11-12 1976-01-20 Armstrong Chemical Company, Inc. Fabric softener compound and processes for preparing and using the same
JPS5338794A (en) * 1976-09-17 1978-04-10 Kao Corp Composition for fabric softening agent
ATE4334T1 (de) * 1979-01-11 1983-08-15 The Procter & Gamble Company Konzentrierte textilweichmachungszusammensetzung.

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3681241A (en) * 1968-03-04 1972-08-01 Lever Brothers Ltd Fabric softening

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0079643A2 (fr) * 1981-11-17 1983-05-25 THE PROCTER & GAMBLE COMPANY Compositions adoucissantes concentrées pour matières textiles
EP0079643A3 (fr) * 1981-11-17 1984-07-04 THE PROCTER & GAMBLE COMPANY Compositions adoucissantes concentrées pour matières textiles
EP0275694A1 (fr) * 1986-12-24 1988-07-27 Unilever Plc Composition adoucissante liquide pour le tissu
AU633288B2 (en) * 1988-12-15 1993-01-28 Procter & Gamble Company, The Liquid fabric softener
EP0373696A3 (fr) * 1988-12-15 1990-07-18 The Procter & Gamble Company Adoucissant textile liquide
EP0373696A2 (fr) * 1988-12-15 1990-06-20 The Procter & Gamble Company Adoucissant textile liquide
WO1993001265A1 (fr) 1991-07-05 1993-01-21 Unilever Plc Composition adoucissante pour tissus
WO1993016157A1 (fr) * 1992-02-07 1993-08-19 Henkel Kommanditgeselschaft Auf Aktien Procede de fabrication de concentres aqueux, de faible viscosite, d'esters quaternises
US5433869A (en) * 1992-12-22 1995-07-18 Colgate-Palmolive Co. Liquid fabric conditioning composition containing amidoamine softening compound
US5545340A (en) * 1993-03-01 1996-08-13 The Procter & Gamble Company Concentrated biodegradable quaternary ammonium fabric softener compositions and compounds containing intermediate iodine value unsaturated fatty acid chains
EP0734433B1 (fr) * 1993-12-13 2000-03-22 The Procter & Gamble Company Compositions assouplissantes concentrees liquides, de viscosite stable
US5474690A (en) * 1994-11-14 1995-12-12 The Procter & Gamble Company Concentrated biodegradable quaternary ammonium fabric softener compositions containing intermediate iodine value fatty acid chains
EP0768369A1 (fr) * 1995-10-11 1997-04-16 The Procter & Gamble Company Compositions adoucissantes
EP0856045A1 (fr) * 1995-10-11 1998-08-05 The Procter & Gamble Company Compositions adoucissantes pour tissus
EP0856045A4 (fr) * 1995-10-11 1999-06-09 Procter & Gamble Compositions adoucissantes pour tissus

Also Published As

Publication number Publication date
MX157118A (es) 1988-10-28
AU7755981A (en) 1982-05-27
JPH0152507B2 (fr) 1989-11-09
EP0052517B1 (fr) 1985-04-24
DE3170187D1 (en) 1985-05-30
AU544660B2 (en) 1985-06-06
JPS57154463A (en) 1982-09-24
ATE12947T1 (de) 1985-05-15

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