EP0648835A1 - Utilisation de sels alcalins de polyammonium pour augmenter la densité cationique des adoussinants textiles - Google Patents

Utilisation de sels alcalins de polyammonium pour augmenter la densité cationique des adoussinants textiles Download PDF

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Publication number
EP0648835A1
EP0648835A1 EP93202884A EP93202884A EP0648835A1 EP 0648835 A1 EP0648835 A1 EP 0648835A1 EP 93202884 A EP93202884 A EP 93202884A EP 93202884 A EP93202884 A EP 93202884A EP 0648835 A1 EP0648835 A1 EP 0648835A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
polyammonium
present
cationic
fabric softening
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.)
Withdrawn
Application number
EP93202884A
Other languages
German (de)
English (en)
Inventor
Hugo Jean Marie Demeyere
Franciscus Joseph Madeleine De Block
Brian Joseph Pangrle
Jean-Pol Boutique
Michel Jean Hector Philippi
Jean-François Bodet
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 Co
Original Assignee
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 Co filed Critical Procter and Gamble Co
Priority to EP93202884A priority Critical patent/EP0648835A1/fr
Priority to PCT/US1994/011422 priority patent/WO1995010655A1/fr
Priority to CA 2172496 priority patent/CA2172496A1/fr
Priority to BR9407830A priority patent/BR9407830A/pt
Publication of EP0648835A1 publication Critical patent/EP0648835A1/fr
Withdrawn legal-status Critical Current

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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
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38Cationic compounds
    • C11D1/62Quaternary ammonium 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
    • 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
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16Organic compounds
    • C11D3/26Organic compounds containing nitrogen
    • C11D3/30Amines; Substituted amines ; Quaternized amines

Definitions

  • the invention relates to the use of a composition
  • a composition comprising cationic fabric softeners, preferably quaternary ammonium esters and (C3-C10) alkyl/aryl polyammonium salts.
  • polyammonium salts are used to replace partially or fully calcium chloride to aid the cationic fabric softeners in depositing on fabrics while reducing the inter-cationic interferences usually leading to low deposition densities.
  • compositions containing polyammonium salts and conventional fabric softeners are disclosed in US application 07/88/979. However, no mention of the use of these polyammonium salts as deposition density aid is disclosed in this document.
  • FR-A-1581392 discloses diamine salts falling within the definition of the polyammonium salts of the present invention. However, these diamine salts are disclosed in the context of washing powders including anionic detergents.
  • GB-A-2006237 discloses polymers comprising a monomere of alky-diamines. These monomeres also fall within the definition of the polyammonium salts of the present invention.
  • the compositions disclosed are used in hair care formulations and the polymers derived from the polyammonium monomeres are said to have improved compatibility with anionic surfactants.
  • EP-A-69948 and JP-A-90012203 disclose polyammonium compounds in the context of fabric treatment compositions. However, no indication of these compounds falling within the definition of the present invention has been found.
  • the problem underlying the present invention is to provide viscosity control and stability of fabric softening compositions, to increase the density of cations which can be deposited on a fabric fiber and, at the same time, to perform anionic scavenging for carry-over detergent from the main wash.
  • the present invention relates to the use of soluble polyammonium salts for viscosity control, deposition density aid and anionic scavenging in rinse added fabric softening compositions.
  • the fabric softening compositions comprise insoluble fabric softening agent and, at least 0.1 % by weight of a (C3-C10)alkyl or aryl polyammonium salt.
  • a (C3-C10)alkyl or aryl polyammonium salt a (C3-C10)alkyl or aryl polyammonium salt.
  • partially quaternized or non-quaternized polyammonia can be used provided the rinse added composition is used in an environment such that the non-quaternized or partially non-quaternized ammonia becomes protonated through acidic buffering of the rinse liquid.
  • Any useful acids buffering the rinse liquid can be used in this context and the ammonia can be seen as the precursor of quaternized ammoniums.
  • the cationic fabric softening compound The cationic fabric softening compound.
  • the essential fabric softening compound of the present invention is typically a non-soluble quaternized ammonium, preferably a di-ester quaternary ammonium.
  • the cationic fabric softening compound is present in a total amount of at least 15 %, more preferably in an amount of 15 % to 25 %, not accounting for optional cationic fabric softeners.
  • substituents R and R2 can optionally be substituted with various groups such as alkoxyl or hydroxyl groups, and/or can be saturated, unsaturated, straight and/or branched so long as the R2 groups maintain their basically lipophilic character.
  • the preferred compounds can be considered to be di-ester variations of ditallow dimethyl ammonium chloride(DTDMAC), which is a widely used fabric softener. At least 80% is in the di-ester form, and from 0 % to about 20% can be monoester.
  • DTDMAC ditallow dimethyl ammonium chloride
  • the di-ester when specified, it will include the monoester that is normally present, but not additional monoester that is added. For softening, the percentage of di-ester should be as high as possible, preferably more than 90%.
  • the above compounds used as the primary active softener ingredient in the practice of this invention can be prepared using standard reaction chemistry.
  • an amine of the formula RN(CH2CH2OH)2 is esterified at both hydroxyl groups with an acid chloride of the formula R2C(O)C1, then quaternized with an alkyl halide, RX, to yield the desired reaction product (wherein R and R2 are as defined herinbefore).
  • stable liquid compositions herein are formulated at a pH in the range of about 2 to about 5, preferably from about 2 to about 4.5, more preferably from about 2 to about 4.
  • Suitable Bronsted acids include the inorganic mineral acids, carboxylic acids, in particular the low molecular weight (C1-C5) carboxylic acids, and alkylsulfonic acids.
  • Suitable inorganic acids include HCl, H2SO4, HNO3 and H3PO4.
  • Suitable organic acids include formic, acetic, methylsulfonic and ethylsulfonic acid.
  • Preferred acids are hydrochloric and phosphoric acids. The presence of the aromatic acids which are useful in the present invention also helps to stabilize the di-ester compounds.
  • the preferred di-ester quaternary ammonium fabric softening compound can also have the general formula : wherein each R, R2 and X have the same meanings as before.
  • Such compounds include those having the formula : [CH3]3 N+[CH2CH(CH2OC(O)R2)OC(O)R2] Cl ⁇ where -OC(O)R2 is derived from soft or hard tallow, or mixtures thereof.
  • each R is a methyl or ethyl group and preferably each R2 is in the range of C15 to C19. Degrees of branching, substitution and/or non-saturation can be present in the alkyl chains.
  • the anion X ⁇ in the molecule is preferably the anion of a strong acid and can be, for example, chloride, bromide, iodide, sulfate and methyl sulfate; the anion can carry a double charge in which case X ⁇ represents half a group.
  • iodine value of above 30 up to 100, preferably above 50, has been found to be beneficial. Also beneficial, particularly if the iodine value is not above 70, are double bonds of the cis configuration due to their melting point difference vs trans double bonds.
  • cationic materials with ring structures such as alkyl imidazoline, imidazolinium, pyridine, and pyridinium salts having a single C12-C30 alkyl chain can also be used. Very low pH is required to stabilize, e.g. imidazoline ring structures.
  • alkyl imidazolinium salts useful in the present invention have the general formula : wherein Y2 is -C(O)-O-, -O-(O)-C-, -C(O)-N(R5), or -N(R5)-C(O)- in which R5 is hydrogen or a C1-C4 alkyl radical; R6 is a C1-C4 alkyl radical; R7 and R8 are each independently selected from R and R2 as defined hereinbefore for the single-chain cationic surfactant with only one being R2.
  • alkyl pyridinium salts useful in the present invention have the general formula : R2 - N+ X ⁇ wherein R2 and X ⁇ are as defined above.
  • a typical material of this type is cetyl pyridinium chloride.
  • Further optional cationic and other softening compounds have been described or referred to in PCT application US-93-04107 filed May 3, 1993.
  • the fabric softener compositions optionally further contain quaternary - di or poly - ammoniums as described in detail in EP-A-503155 and EP-A-507003. These ammoniums are non-soluble cationic fabric softeners.
  • (C3-C10) alkyl or aryl polyammonium salts, or the ammonia precursors in a protonating environment are used according to the present invention for viscosity control, as deposition density aid and for anionic scavenging in rinse added fabric softening compositions. They are present in the fabric softening compositions in amounts of at least 0.1 %, preferably from 0.1 % to 5 %, most preferably from 0.2 % to 1 % by weight of the composition.
  • polyammonium salts will be described with the nitrogen in its ammonium state but, as indicated above, they can be used with one or all nitrogens in their ammonia state, provided that they become protenated upon use. This in ensured by having sufficient protons available e.g. by the presence of an acid as described above.
  • Preferred polyammonium salts are (C3-C8) alkyl polyammonium salts, particularly di-ammonium salt. Examples of such salts are
  • This "partial individualisation of charges” can be compared for di-ammoniums with a model of two positive charges connected by a string which provides a high level of independence between the charges in comparison to a double charged calcium.
  • the density of the two charges connected by the string is higher than two independently charged molecules, since the string length is small relative to the distance which would be reached by electrical repellance for an even distribution of independently charged molecules on an identical number of charges.
  • polyammonium salts provides a better control of the viscosity of the composition in that the polyammonium salts allow lower and higher temperatures without unacceptable viscosity conditions (i.e. gelling at low temperatures, watery appearance at high temperatures) relative to a comparably formulated composition using CaCl2.
  • polyammonium salts allows better scavenging of carry over anionic surfactants (which is possibly due to the "partial individualisation of charges") and hence prevents depletion of the active cationic softening compound.
  • single long chain cationic surfactants which are water soluble, can be present in amounts of 0% up to 15%.
  • Such single long-chain-alkyl surfactants useful in the present invention are, preferably quaternary ammonium salts of the general formula: [R2N+R3] X ⁇ wherein the R2 group is C10-C22 hydrocarbon group, preferably C12-C18 alkyl group or the corresponding ester linkage interrupted group with a short alkylene (C1-C4) group between the ester linkage and the N, and having a similar hydrocarbon group, e.g.
  • a fatty acid ester of choline preferably C12-C14 (coco) choline ester and/or C16-C18 tallow choline ester.
  • Each R is a C1-C4 alkyl or substituted (e.g. hydroxy) alkyl, or hydrogen, preferably methyl, and the counterion X ⁇ is a softener compatible anion, for example, chloride, bromide, methyl sulfate, etc.
  • the ranges above represent the amount of the water soluble single-long-chain-alkyl cationic surfactant which is added to the composition of the present invention.
  • the ranges do not include the amount of monoester which is already present in the essential fabric softening compound.
  • the long chain group R2 of the single-long-chain-alkyl cationic surfactant typically contains an alkylene group having from about 10 to about 22 carbon atoms, preferably from about 12 to about 18 carbon atoms.
  • This R2 group can be attached to the cationic nitrogen atom through a group containing one, or more, ester, amide, ether, amine, etc., preferably ester, linking groups which can be desirable for increased hydrophilicity, biodegradability, etc.
  • Such linking groups are preferably within about three carbon atoms of the nitrogen atom.
  • Suitable biodegradable single-long-chain alkyl cationic surfactants containing an ester linkage between the nitrogen and the long chain are described in U.S. 4,840,738.
  • the main function of the water-soluble cationic surfactant is to lower the viscosity and/or increase the dispersibility of the essential fabric softener compound and it is not therefore, essential that the cationic surfactant itself have substantial softening properties, although this may be the case.
  • surfactants having only a single long alkyl chain presumably because they have greater solubility in water, can protect the essential fabric softener compound from interacting with anionic surfactants and/or detergent builders that are carried over into the rinse.
  • non-ionic surfactants Another optional compound improving the viscosity of highly concentrated fabric softening compositions are non-ionic surfactants.
  • Suitable non-ionic surfactants to serve as viscosity/dispersibility modifier include addition products of ethylene oxide and, optionally, propylene oxide, with fatty alcohols, fatty acids, fatty amines, etc.
  • any of the alkoxylated materials of the particular type described hereinafter can be used as the non-ionic surfactant.
  • the non-ionics are used at a level of from 0% to about 15%.
  • Suitable compounds are substantially water-soluble surfactants of the general formula : R9 - Y - (C2H4O) Z - C2H4OH wherein R9 is selected from the group consisting of primary, secondary and branched chain alkyl and/or acyl hydrocarbyl groups; primary, secondary and branched chain alkenyl hydrocarbyl groups; and primary, secondary and branched chain alkyl- and alkenyl-substituted phenolic hydrocarbyl groups; said hydrocarbyl groups having a hydrocarbyl chain length of from 8 to about 20, preferably from about 10 to about 18 carbon atoms.
  • the hydrocarbyl chain length is from 16 to 18 carbon atoms.
  • Y is typically -O-, -C(O)O-, -C(O)N(R)-, or -C(O)N(R9)R-, in which R9, and R, when present, have the meanings given hereinbefore, and/or R can be hydrogen, and z is at least about 8, preferably at least about 10-11. Performance and, usually, stability of the softener composition decrease when fewer ethoxylate groups are present.
  • non-ionic surfactants are disclosed in further detail in PCT application US-93-04107 filed May 3, 1993. All of the typical fabric softener compounds usual in the art may further be present in the compositions according to the present invention, in particular enzymes (protease, lipase, cellulase and amylase, especially cellulase), perfumes, dyes, solvents, polymers, bacterial and fungal stabilizers and other compounds.
  • enzymes prote, lipase, cellulase and amylase, especially cellulase
  • perfumes dyes, solvents, polymers, bacterial and fungal stabilizers and other compounds.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (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)
EP93202884A 1993-10-14 1993-10-14 Utilisation de sels alcalins de polyammonium pour augmenter la densité cationique des adoussinants textiles Withdrawn EP0648835A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP93202884A EP0648835A1 (fr) 1993-10-14 1993-10-14 Utilisation de sels alcalins de polyammonium pour augmenter la densité cationique des adoussinants textiles
PCT/US1994/011422 WO1995010655A1 (fr) 1993-10-14 1994-10-07 Utilisation de sels de polyammonium d'alcalene pour augmenter la densite cationique d'assouplissants pour textiles
CA 2172496 CA2172496A1 (fr) 1993-10-14 1994-10-07 Utilisation de sels de polyammonium d'alcalene pour augmenter la densite cationique d'assouplissants pour textiles
BR9407830A BR9407830A (pt) 1993-10-14 1994-10-07 Uso de sais de poliamônio alquileno para aumentar a densidade catiônica em amaciantes para tecidos

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP93202884A EP0648835A1 (fr) 1993-10-14 1993-10-14 Utilisation de sels alcalins de polyammonium pour augmenter la densité cationique des adoussinants textiles

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EP0648835A1 true EP0648835A1 (fr) 1995-04-19

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EP93202884A Withdrawn EP0648835A1 (fr) 1993-10-14 1993-10-14 Utilisation de sels alcalins de polyammonium pour augmenter la densité cationique des adoussinants textiles

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EP (1) EP0648835A1 (fr)
BR (1) BR9407830A (fr)
CA (1) CA2172496A1 (fr)
WO (1) WO1995010655A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6939844B2 (en) 1996-09-19 2005-09-06 The Procter & Gamble Company Concentrated, preferably biodegradable, quaternary ammonium fabric softener compositions containing cationic polymers and process for preparation
US7135451B2 (en) 2003-03-25 2006-11-14 The Procter & Gamble Company Fabric care compositions comprising cationic starch

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998050583A1 (fr) * 1997-05-02 1998-11-12 Gen-Probe Incorporated Hybridation en deux temps et capture d'un polynucleotide

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0060003A2 (fr) * 1981-03-07 1982-09-15 THE PROCTER & GAMBLE COMPANY Compositions pour le traitement de matières textiles et leur préparation
EP0069948A1 (fr) * 1981-07-10 1983-01-19 Hoechst Aktiengesellschaft Esters quaternaires d'un N-alkyl N,N',N'-polyoxyalkyl alpha oméga-diaminoalkylène avec des acides gras, leur procédé de préparation et leur utilisation
JPS58172308A (ja) * 1982-04-02 1983-10-11 Ajinomoto Co Inc 柔軟剤組成物
EP0165138A2 (fr) * 1984-05-16 1985-12-18 STEPAN EUROPE, Société anonyme dite: Compositions adoucissantes concentrées à base d'agents tensio-actifs cationiques d'ammonium quaternaire
EP0296995A1 (fr) * 1987-06-16 1988-12-28 Cotelle S.A. Compositions adoucissantes concentrées
EP0507003A2 (fr) * 1991-04-03 1992-10-07 REWO Chemische Werke GmbH Nouveaux composés d'ammonium, procédé pour leur préparation et leur utilisation comme agents de nettoyage, matériaux bruts pour cosmétiques et agents d'adoucissement, sûrtout comme agents de tissage pour textiles
WO1993016157A1 (fr) * 1992-02-07 1993-08-19 Henkel Kommanditgeselschaft Auf Aktien Procede de fabrication de concentres aqueux, de faible viscosite, d'esters quaternises

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0043622B1 (fr) * 1980-01-07 1984-11-21 THE PROCTER & GAMBLE COMPANY Composition d'adoucissement pour matières textiles
ATE13562T1 (de) * 1981-01-16 1985-06-15 Procter & Gamble Textilbehandlungsmittel.
US4497716A (en) * 1982-12-23 1985-02-05 Lever Brothers Company Fabric softening composition

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0060003A2 (fr) * 1981-03-07 1982-09-15 THE PROCTER & GAMBLE COMPANY Compositions pour le traitement de matières textiles et leur préparation
EP0069948A1 (fr) * 1981-07-10 1983-01-19 Hoechst Aktiengesellschaft Esters quaternaires d'un N-alkyl N,N',N'-polyoxyalkyl alpha oméga-diaminoalkylène avec des acides gras, leur procédé de préparation et leur utilisation
JPS58172308A (ja) * 1982-04-02 1983-10-11 Ajinomoto Co Inc 柔軟剤組成物
JPH0212203B2 (fr) * 1982-04-02 1990-03-19 Ajinomoto Kk
EP0165138A2 (fr) * 1984-05-16 1985-12-18 STEPAN EUROPE, Société anonyme dite: Compositions adoucissantes concentrées à base d'agents tensio-actifs cationiques d'ammonium quaternaire
EP0296995A1 (fr) * 1987-06-16 1988-12-28 Cotelle S.A. Compositions adoucissantes concentrées
EP0507003A2 (fr) * 1991-04-03 1992-10-07 REWO Chemische Werke GmbH Nouveaux composés d'ammonium, procédé pour leur préparation et leur utilisation comme agents de nettoyage, matériaux bruts pour cosmétiques et agents d'adoucissement, sûrtout comme agents de tissage pour textiles
WO1993016157A1 (fr) * 1992-02-07 1993-08-19 Henkel Kommanditgeselschaft Auf Aktien Procede de fabrication de concentres aqueux, de faible viscosite, d'esters quaternises

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
DATABASE WPI Week 8346, Derwent World Patents Index; AN 83-818125 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6939844B2 (en) 1996-09-19 2005-09-06 The Procter & Gamble Company Concentrated, preferably biodegradable, quaternary ammonium fabric softener compositions containing cationic polymers and process for preparation
US7135451B2 (en) 2003-03-25 2006-11-14 The Procter & Gamble Company Fabric care compositions comprising cationic starch

Also Published As

Publication number Publication date
BR9407830A (pt) 1997-05-13
WO1995010655A1 (fr) 1995-04-20
CA2172496A1 (fr) 1995-04-20

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