DE4403686A1 - Aq. fabric conditioner dispersions - Google Patents

Aq. fabric conditioner dispersions

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Publication number
DE4403686A1
DE4403686A1 DE4403686A DE4403686A DE4403686A1 DE 4403686 A1 DE4403686 A1 DE 4403686A1 DE 4403686 A DE4403686 A DE 4403686A DE 4403686 A DE4403686 A DE 4403686A DE 4403686 A1 DE4403686 A1 DE 4403686A1
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Germany
Prior art keywords
atoms
group
formula
alkyl
dispersions
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.)
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DE4403686A
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German (de)
Inventor
Fred Dr Schambil
Theodor Voelkel
Rolf Dr Puchta
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.)
Henkel AG and Co KGaA
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Henkel AG and Co KGaA
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Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Priority to DE4403686A priority Critical patent/DE4403686A1/en
Publication of DE4403686A1 publication Critical patent/DE4403686A1/en
Withdrawn legal-status Critical Current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
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • 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
    • D06M13/463Compounds containing quaternary nitrogen atoms derived from monoamines
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/08Sulfation or sulfonation products of fats, oils, waxes, or higher fatty acids or esters thereof with monovalent alcohols
    • 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
    • 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
    • D06M2200/00Functionality of the treatment composition and/or properties imparted to the textile material
    • D06M2200/50Modified hand or grip properties; Softening compositions

Landscapes

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

Abstract

Aq. fabric conditioner dispersions contain 1-10 wt.% of a dispersed cationic fabric conditioner of formula (I) and 0.1-5 wt.% of a dispersed cationic fabric conditioner of formula (II), where R1CO = satd. or unsatd. 12-22C acyl; R2 = R1CO(OCnH2n)z, 1-4C alkyl or 2-4C hydroxyalkyl; R3 = 1-4C alkyl or 2-4C hydroxyalkyl; n = 2 or 3; x, y and z = 1-4; A = halide or MeSO4; R4 = CH2COOR7 or (CnH2n)pCOR8; R5 and R6 = 1-4C alkyl or 2-4C hydroxyalkyl; R7 = 12-22C alkyl or alkenyl; COR8 = satd. or unsatd. 12-22C acyl; and p = 1-4. Pref. the dispersions contain 2-6% (I) and 0.1-3% (II).

Description

Die Erfindung betrifft die Herstellung von wäßrigen Textilweichma­ cher-Dispersionen auf Basis kationischer Textilweichmacher vom Typ der quartären Ammoniumverbindungen mit wenigstens zwei langen Al­ kyl-, Alkenyl- oder Acylgruppen die aufgrund einer speziell ausge­ wählten Kombination quartärer Ammoniumverbindungen eine erhöhte Viskosität und ein besonders günstiges Lagerverhalten aufweisen.The invention relates to the production of aqueous textile soft material cher dispersions based on cationic textile softeners of the type the quaternary ammonium compounds with at least two long Al kyl, alkenyl or acyl groups which have a specially formed selected combination of quaternary ammonium compounds an increased Have viscosity and a particularly favorable storage behavior.

Die in Wäschweichspülmitteln gebräuchlichen Textilweichmacher vom Typ der quartären Ammoniumverbindungen mit wenigstens zwei langket­ tigen Alkyl- oder Acylgruppen sind in Wasser wenig löslich und lie­ gen daher auch im Bereich niedriger Konzentrationen von weniger als z. B. 10 Gew.-% in Wasser als Dispersion vor. Diese Dispersionen ha­ ben die Eigenschaft, daß sie zwar bei höheren Konzentrationen von mehr als 15 Gew.-% in Wasser sehr hochviskos und wenig fließfähig sind, im Bereich niedrigerer Konzentrationen von z. B. unter 10 Gew.-%, also in dem für Haushalts-Wäscheweichspülmittel üblichen Konzentrationsbereich aber sind diese Dispersionen sehr dünnflüs­ sig. Die niedrige Viskosität dieser Dispersionen ist von Nachteil für die Lagerstabilität und erschwert auch die Handhabung und Do­ sierung der Produkte.The fabric softeners commonly used in fabric softeners from Type of quaternary ammonium compounds with at least two long chains term alkyl or acyl groups are sparingly soluble in water and lie therefore also in the range of low concentrations of less than e.g. B. 10 wt .-% in water as a dispersion. These dispersions ha have the property that they are at higher concentrations of more than 15% by weight in water very highly viscous and not very flowable are, in the range of lower concentrations of z. B. under 10 % By weight, that is to say in that customary for household fabric softening detergents  Concentration range, however, these dispersions are very thin sig. The low viscosity of these dispersions is disadvantageous for storage stability and also complicates handling and do products.

Es sind zwar schon verschiedene Möglichkeiten zur Verdickung solcher Dispersionen vorgeschlagen worden, z. B. durch Zusatz wasserlöslicher Polymeren. Solche Produkte haben jedoch den Nachteil, daß sie die gewebeweichmachende Wirkung beeinträchtigen, daß die Produkte oft nicht ausreichend biologisch abbaubar sind, und daß die Viskosität sich im Laufe längerer Lagerzeiten oft stark verändert.There are different ways to thicken such Dispersions have been proposed, e.g. B. by adding water-soluble Polymers. However, such products have the disadvantage that they Fabric softening effects often affect the products are not sufficiently biodegradable and that the viscosity often changes significantly over the course of longer storage times.

Insbesondere die gut biologisch abbaubaren kationischen Textilweichmacher vom Typ der quartären Ammoniumverbindungen mit zwei Fettacyl­ oxyalkylgruppen lassen sich ohne Hilfsmittel nur zu sehr dünnflüssi­ gen Dispersionen verarbeiten. Es bestand daher die Aufgabe, wäßrige Textilweichmacher-Dispersionen zu entwickeln, die gut biologisch abbaubar sind, eine hohe Weichspülleistung aufweisen und deren wäß­ rige Dispersion in niedrigen Konzentrationsbereichen eine befriedi­ gende Viskosität aufweist.In particular the readily biodegradable cationic fabric softeners of the type of quaternary ammonium compounds with two fatty acyls oxyalkyl groups can only be used in very thin liquids without auxiliary agents process dispersions. There was therefore the task of aqueous To develop textile softener dispersions that are good biological are degradable, have a high fabric softener performance and their aq dispersion in low concentration ranges a satisfactory has sufficient viscosity.

Gegenstand der Erfindung ist eine wäßrige Weichspülmittel-Dispersion mit einem Gehalt vonThe invention relates to an aqueous fabric softener dispersion grading

  • (A) 1-10 Gew.-% eines dispergierten kationischen Textilweichma­ chers der Formel I in der R¹CO- eine gesättigte oder ungesättigte Acylgruppe mit 12-22 C-Atomen, R² eine Gruppe R¹CO(OCnH2n)z-, eine Alkyl­ gruppe mit 1-4 C-Atomen oder eine Hydroxyalkylgruppe mit 2-4 C-Atomen und R³ eine Alkylgruppe mit 1-4 C-Atomen oder eine Hydroxyalkylgruppe mit 2-4 C-Atomen, n jeweils 2 oder 3, x, y und z jeweils eine Zahl von 1-4 und A⊖ ein Halogenid- oder CH₃OSO₃⊖-Anion ist und(A) 1-10% by weight of a dispersed cationic fabric softener of the formula I. in the R¹CO- a saturated or unsaturated acyl group with 12-22 C-atoms, R² a group R¹CO (OC n H 2n ) z -, an alkyl group with 1-4 C-atoms or a hydroxyalkyl group with 2-4 C-atoms and R³ is an alkyl group with 1-4 C atoms or a hydroxyalkyl group with 2-4 C atoms, n each 2 or 3, x, y and z each have a number from 1-4 and A⊖ is a halide or CH₃OSO₃⊖- Anion is and
  • (B) 0,1-5 Gew.-% eines dispergierten kationischen Textilweichma­ chers der Formel II in der R⁴ eine Gruppe -CH₂-COOR⁷ oder -(CnH2nO)p-COR⁸, R⁵ und R⁶ Alkylgruppen mit 1-4 C-Atomen oder Hydroxyalkylgruppen mit 2-4 C-Atomen sind, R⁷ eine Alkyl- oder Alkenylgruppe mit 12-22 C-Atomen und -COR⁸ eine gesättigte oder ungesättigte Acylgruppe mit 12-22 C-Atomen ist, n jeweils 2 oder 3 und p jeweils eine Zahl von 1-4 und A⊖ ein Halogenid- oder CH₃OSO₃⊖-Anion ist.(B) 0.1-5% by weight of a dispersed cationic fabric softener of the formula II in which R⁴ is a group -CH₂-COOR⁷ or - (C n H 2n O) p -COR⁸, R⁵ and R⁶ are alkyl groups with 1-4 C atoms or hydroxyalkyl groups with 2-4 C atoms, R⁷ is an alkyl or alkenyl group with 12-22 carbon atoms and -COR⁸ is a saturated or unsaturated acyl group with 12-22 carbon atoms, n is 2 or 3 and p each is a number from 1-4 and A⊖ is a halide or CH₃OSO₃⊖ anion .

Diese erfindungsgemäßen wäßrigen Textilweichmacher-Dispersionen wei­ sen auch ohne besondere Zusätze eine gegenüber den entsprechenden Dispersionen der Komponente (A) deutlich erhöhte Viskosität auf. Dies gilt insbesondere für relativ niedrig konzentrierte Dispersi­ onen, dieThese aqueous textile plasticizer dispersions according to the invention white one without any special additives compared to the corresponding ones Dispersions of component (A) have a significantly increased viscosity. This is particularly true for dispersions with a relatively low concentration ones that

  • (A) 2-6 Gew.-% eines Textilweichmachers der Formel I und(A) 2-6% by weight of a fabric softener of formula I and
  • (B) 0,01-3 Gew.-% eines Textilweichmachers der Formel II(B) 0.01-3% by weight of a textile softener of the formula II

enthalten.contain.

Die textilweichmachenden quartären Ammoniumverbindungen sind bekann­ te Stoffe und im Handel erhältlich. Sie haben textilweichmachende Wirkung und sind auch gut biologisch abbaubar. So sind z. B. quartäre Ammoniumverbindungen, die der Formel I entsprechen, aus DE 17 94 068 und DE 19 35 499 bekannt. Ein Handelsprodukt dieses Typs ist Stepan­ tex VS 90, ein Di-(talgfettacyl-oxyethyl)-2-hydroxyethyl-methyl­ methosulfat. Ein weiteres Handelsprodukt dieses Typs ist Armosoft DEAQ, ein Di-(C₁₆/C₁₈-acyl-oxyethyl)-dimethyl-ammonium-chlorid.The textile-softening quaternary ammonium compounds are known fabrics and commercially available. They have fabric softeners Effect and are also readily biodegradable. So z. B. quaternary Ammonium compounds corresponding to formula I from DE 17 94 068 and DE 19 35 499 known. A commercial product of this type is Stepan tex VS 90, a di (tallow fatty acyl oxyethyl) -2-hydroxyethyl methyl methosulfate. Another commercial product of this type is Armosoft DEAQ, a di (C₁₆ / C₁₈ acyl oxyethyl) dimethyl ammonium chloride.

Quartäre Ammoniumverbindungen der Formel II sind z. B. aus EP 21 431 A1 bekannt. Handelsprodukte dieses Typs sind z. B. Armosoft DMDQ, eine Verbindung der Formel II, in der R⁴ eine Gruppe -CH₂COOR⁷, R⁵ und R⁶ Methylgruppen, R⁷ eine C₁₆/C₁₈-Alkylgruppe und A⊖ ein Chlo­ rid-Anion ist. Ein weiteres Handelsprodukt ist Armosoft AEBE, eine Verbindung der Formel II, in der R⁴ eine Gruppe -CH₂-CH₂O-COR⁸, R⁵ und R⁶ Methylgruppen, -COR⁸ eine C₁₆/C₁₈-Acylgruppe und R⁷ eine C₁₆/C₁₈-Alkylgruppe und A⊖ ein Chlorid-Anion ist.Quaternary ammonium compounds of the formula II are e.g. B. from EP 21 431 A1 known. Commercial products of this type are e.g. B. Armosoft DMDQ, a compound of formula II in which R⁴ is a group -CH₂COOR⁷, R⁵ and R⁶ is a methyl group, R⁷ is a C₁₆ / C₁₈ alkyl group and A⊖ is a Chlo is rid anion. Another commercial product is Armosoft AEBE, a Compound of formula II in which R⁴ is a group -CH₂-CH₂O-COR⁸, R⁵ and R⁶ is methyl groups, -COR⁸ is a C₁₆ / C₁₈ acyl group and R⁷ is one C₁₆ / C₁₈ alkyl group and A⊖ is a chloride anion.

Neben den erfindungsgemäß einzusetzenden quartären Ammoniumverbin­ dungen der Formeln I und II können die wäßrigen Textilweichmacher- Dispersionen noch weitere, in Wäscheweichspülmitteln übliche Zusätze enthalten. Als solche sind z. B. weitere, zur Viskositätsbeeinflus­ sung geeignete Zusätze zu nennen, wie z. B. aliphatische Diole und Polyole oder Polyethylenglycole, die zur Verbesserung der Viskosi­ tätsstabilität gegenüber Scherbeanspruchung beitragen.In addition to the quaternary ammonium compound to be used according to the invention formulas I and II, the aqueous fabric softener Dispersions and other additives common in fabric softeners contain. As such, e.g. B. more, to influence viscosity solution to name suitable additives, such as. B. aliphatic diols and Polyols or polyethylene glycols that improve viscos stability against shear stress.

Weiterhin können auch anionische Sulfat- oder Sulfonat-Tenside, z. B. Fettalkoholsulfat, Natriumsalze auf Basis von C₁₂-C₁₈-Fettalkoholen bereits in kleinen Mengen die Viskosität der Dispersionen erhöhen. Auch Elektrolyte können zur Beeinflussung der rheologischen Eigen­ schaften eingesetzt werden. Darüber hinaus kann man den Wäscheweich­ spülern auch noch andere Hilfsmittel, z. B. Fettsäuren mit 12-22 C-Atomen, Fettsäurepartialglyceriden, Fettsäureoxethylate, Fett­ säureester, Fettalkoholpolyglycolether und andere Emulgatoren zu­ setzen. Auch Hilfsmittel, die eine antimikrobielle oder ölabweisende Ausrüstung der Textilfasern bewirken, können in die Weichspülmit­ tel-Formulierung eingearbeitet werden. Schließlich gehören Farbstof­ fe, optische Aufheller und Duftstoffe zu den üblichen Zusätzen in Wäscheweichspülmitteln.Furthermore, anionic sulfate or sulfonate surfactants, e.g. B. Fatty alcohol sulfate, sodium salts based on C₁₂-C₁₈ fatty alcohols  increase the viscosity of the dispersions even in small quantities. Electrolytes can also influence the rheological properties be used. You can also use the laundry soft also rinse other aids, e.g. B. fatty acids with 12-22 C atoms, fatty acid partial glycerides, fatty acid oxyethylates, fat acid esters, fatty alcohol polyglycol ethers and other emulsifiers put. Also aids that have an antimicrobial or oil repellent Finishing of the textile fibers can result in the fabric softener tel formulation are incorporated. After all, dye belongs Fe, optical brighteners and fragrances to the usual additives in Fabric softener.

Die folgenden Beispiele sollen den Erfindungsgegenstand näher er­ läutern: The following examples are intended to illustrate the subject matter of the invention purify:  

BeispieleExamples

Es wurden Weichspüler-Zusammensetzungen nach folgender Rahmenrezep­ tur hergestellt:There were fabric softener compositions according to the following general recipe door manufactured:

5 Gew.-% kationischer Textilweichmacher
4,475 ppm Farbstoff
0,3 Gew.-% Duftstoff
Rest (ad 100%) Wasser.
5% by weight cationic fabric softener
4.475 ppm dye
0.3% by weight of fragrance
Rest (ad 100%) water.

Der kationische Textilweichmacher war wie folgt zusammengesetzt:The cationic fabric softener was composed as follows:

Dabei wurden milchig aussehende, flüssige Dispersionen erhalten, die folgende Viskosität aufwiesen:Milky-looking liquid dispersions were obtained, which had the following viscosity:

Nach weiteren 10 Wochen Lagerung zeigten die Proben keinen weiteren Viskositätsanstieg.After a further 10 weeks of storage, the samples showed no further Viscosity increase.

Claims (3)

1. Wäßrige Weichspülmittel-Dispersion, enthaltend
  • (A) 1-10 Gew.-% eines dispergierten kationischen Textilweich­ machers der Formel I in der R¹CO- eine gesättigte oder ungesättigte Acylgruppe mit 12-22 C-Atomen, R² eine Gruppe R¹CO(OCnH2n)z-, eine Alkylgruppe mit 1-4 C-Atomen oder eine Hydroxyalkylgruppe mit 2-4 C-Atomen und R³ eine Alkylgruppe mit 1-4 C-Ato­ men oder eine Hydroxyalkylgruppe mit 2-4 C-Atomen, n je­ weils 2 oder 3, x, y und z jeweils eine Zahl von 1-4 und A⊖ ein Halogenid- oder CH₃OSO₃⊖- Anion ist und
  • (B) 0,1-5 Gew.-% eines dispergierten kationischen Textil­ weichmachers der Formel II in der R⁴ eine Gruppe -CH₂-COOR⁷ oder -(CnH2nO)p-COR⁸, R⁵ und R⁶ Alkylgruppen mit 1-4 C-Atomen oder Hydroxyal­ kylgruppen mit 2-4 C-Atomen sind, R⁷ eine Alkyl- oder Alkenylgruppe mit 12-22 C-Atomen und -COR⁸ eine gesät­ tigte oder ungesättigte Acylgruppe mit 12-22 C-Atomen ist, n jeweils 2 oder 3 und p jeweils eine Zahl von 1-4 und A⊖ ein Halogenid- oder CH₃OSO₃⊖-Anion ist.
1. Aqueous fabric softener dispersion containing
  • (A) 1-10% by weight of a dispersed cationic fabric softener of the formula I. in the R¹CO- a saturated or unsaturated acyl group with 12-22 C-atoms, R² a group R¹CO (OC n H 2n ) z -, an alkyl group with 1-4 C-atoms or a hydroxyalkyl group with 2-4 C-atoms and R³ is an alkyl group with 1-4 C-atoms or a hydroxyalkyl group with 2-4 C atoms, n each Weil 2 or 3, x, y and z each have a number of 1-4 and A⊖ is a halide or CH₃OSO₃⊖ - Anion is and
  • (B) 0.1-5% by weight of a dispersed cationic textile softener of the formula II in which R⁴ is a group -CH₂-COOR⁷ or - (C n H 2n O) p -COR⁸, R⁵ and R⁶ are alkyl groups with 1-4 C atoms or hydroxyal alkyl groups with 2-4 C atoms, R⁷ is an alkyl or Alkenyl group with 12-22 carbon atoms and -COR⁸ is a saturated or unsaturated acyl group with 12-22 carbon atoms, n is 2 or 3 and p each is a number from 1-4 and A⊖ is a halide or CH₃OSO₃⊖- Anion is.
2. Wäßrige Weichspüler-Dispersion gemäß Patentanspruch 1, dadurch gekennzeichnet, daß
  • (A) 2-6 Gew.-% eines Textilweichmachers der Formel I und
  • (B) 0,1-3 Gew.-% eines Textilweichmachers der Formel II
2. Aqueous softener dispersion according to claim 1, characterized in that
  • (A) 2-6% by weight of a fabric softener of formula I and
  • (B) 0.1-3% by weight of a textile softener of the formula II
enthalten sind.are included.
DE4403686A 1994-02-07 1994-02-07 Aq. fabric conditioner dispersions Withdrawn DE4403686A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
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Application Number Priority Date Filing Date Title
DE4403686A DE4403686A1 (en) 1994-02-07 1994-02-07 Aq. fabric conditioner dispersions

Publications (1)

Publication Number Publication Date
DE4403686A1 true DE4403686A1 (en) 1995-08-10

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DE4403686A Withdrawn DE4403686A1 (en) 1994-02-07 1994-02-07 Aq. fabric conditioner dispersions

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8026206B2 (en) 2005-05-18 2011-09-27 Stepan Company Low solids, high viscosity fabric softener compositions and process for making the same
EP2987905A1 (en) 2014-08-20 2016-02-24 Klaus Schmitt Beteiligungsgesellschaft mbH Means for hydrophilic coating of fabrics composed of hydrophobic thermoplastic materials, and the application of the same

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8026206B2 (en) 2005-05-18 2011-09-27 Stepan Company Low solids, high viscosity fabric softener compositions and process for making the same
EP2987905A1 (en) 2014-08-20 2016-02-24 Klaus Schmitt Beteiligungsgesellschaft mbH Means for hydrophilic coating of fabrics composed of hydrophobic thermoplastic materials, and the application of the same
DE102014111881A1 (en) 2014-08-20 2016-02-25 Klaus Schmitt Beteiligungsgesellschaft Mbh Aqueous waterproofing agent for fabrics of hydrophobic thermoplastic materials and products made therefrom

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