EP0128231B1 - Stabile konzentrierte wässrige Dispersionen von wasserunlöslichen kationischen Verbindungen und deren Zubereitung - Google Patents

Stabile konzentrierte wässrige Dispersionen von wasserunlöslichen kationischen Verbindungen und deren Zubereitung Download PDF

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Publication number
EP0128231B1
EP0128231B1 EP19830105693 EP83105693A EP0128231B1 EP 0128231 B1 EP0128231 B1 EP 0128231B1 EP 19830105693 EP19830105693 EP 19830105693 EP 83105693 A EP83105693 A EP 83105693A EP 0128231 B1 EP0128231 B1 EP 0128231B1
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Prior art keywords
alkoxylated
mols
water
weight
amine
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EP19830105693
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English (en)
French (fr)
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EP0128231A1 (de
Inventor
Joaquim M. Barba
Joan Cáliz
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Camp Fabrica de Jabones SA
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Camp Fabrica de Jabones SA
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Priority to EP19830105693 priority Critical patent/EP0128231B1/de
Priority to DE8383105693T priority patent/DE3373492D1/de
Priority to ES523600A priority patent/ES8500988A1/es
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/835—Mixtures of non-ionic with cationic compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/42—Amino alcohols or amino ethers
    • C11D1/44—Ethers of polyoxyalkylenes with amino alcohols; Condensation products of epoxyalkanes with amines
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/001—Softening compositions
    • C11D3/0015—Softening compositions liquid
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/72—Ethers of polyoxyalkylene glycols

Definitions

  • This present invention deals with concentrated aqueous dispersions or emulsions of insoluble cationic compounds, used as fabric softeners, with an improved stability with time, and in regards to temperature variations in relation to the viscosity and dispersibility in water of the said dispersions. It also deals with the adequate preparation methods for the obtention of the said dispersions.
  • non-ionic alkoxylated surfactants for diluted compositions, and has been applied in concentrated compositions, for instance in the German Patent No. 29 11 198, in the French Patent No. 2 482 636 and in the US-Patent No. 3,947,076, although its utilization has not been sufficiently specified as far as the types of products are concerned, nor as to the effect produced therewith, and, nevertheless, their stabilizing action on viscosity has little effectivity at high temperatures, so it also has to be considered as only a partial answer.
  • the part played by the alkoxylated amines in the compositions described by the documents above cited are both of fabric softening and of enhancing the stability of the dispersion, but all of them are referred to diluted softener compositions, and, moreover, the stabilizing action of the alkoxylated amine has to be concurrent with the joint action of other additives, like urea or alcohols.
  • European Patent Application No. 56 695 is introduced for the first time the concept of the action of alkoxylated amines as factors to achieve a proper viscosity, as well as a satisfactory stability, in concentrated softener compositions, provided that it is associateed to the addition of low levels of electrolyte.
  • the invention herein solves these problems, as in a surprising way unexpected results are achieved in good characteristics of viscosity and a good dispersibility in water of concentrated aqueous dispersions of insoluble cationic compounds, as well as an extended stabilization thereof in ranges of temperatures between 0° and 50°C, by means of the addition of amines with a high degree of alkoxylation in union with a precise and definite system of two non-ionic components. Also, surprisingly, the dispersions described in the invention herein exhibit an excellent adaptability in the maintenance of their physical properties versus abrupt and wide changes of temperature. Also inherent difficulties to the process of obtention of aqueous concentrated dispersions of cationic softeners are solved.
  • the fundamental object of the invention herein is to achieve concentrated aqueous dispersions of insoluble cationic softeners with adequate viscosity and dispersibility and an improved stability in storage and in abrupt temperature changes. Another aim of the invention is the achievement of more economically profitable concentrated softener compositions. Another aim of the invention herein is to develop a process to obtain the compositions hereof, easy and dependable in its results.
  • the invention herein relates to fabric softener compositions which are basically constituted by a cationic fabric softener, an alkoxylated amine and nonionic surfactant characterized in that the mixtures contain:
  • an electrolyte preferably salts of strong acids and divalent metals, the effect of which is very beneficial on the viscosity parameter.
  • the most adequate proportions of the said electrolyte range between 0.02% and 0.15%. Below the inferior limit, the electrolyte action is very unsubstantial, and above the upper limit, there is risk that undesirable phenomena may appear, undermining the stability of the compositions, due to problems of phase disruption.
  • insoluble cationic compounds of the invention herein belong to the type usually used in aqueous dispersions with softening activities on textile fabrics, preferably those belonging to the following groups:
  • alkoxylated tertiary amines with a number of mols of alkylene oxide of 20 to 100 per mol of amine, are highly important to achieve a viscosity between 50 and 900 mPas with a good stability, during long storage terms.
  • the said amines can be used in proportions ranging from 0.1 % to 3% by weight, the preferred proportions are those from 0.5% to 1.5%, with a view to achieve a good balance between the desired effect of viscosity reduction and the final cost of the composition.
  • non-ionic surfactants herein shows itself to be effective to achieve compatibility of the alkoxylated amine with a high degree of alkoxylation with the formulation in presence of small amounts of electrolyte, and it is also basic to confer on the dispersion its qualities of elasticity versus temperature changes during storage.
  • These non-ionic surfactants are selected from amongst the group of alkoxylated fatty alcohols or alkoxylated alkylphenols with a general formula: wherein R 2 represents an alk(en)ylic group between C 8 and C 20 or phenylalkyl from C, to C io , n is an integer from 1 to 4, and z is a number between 1 and 75.
  • the proportion between A and B can have a range between 10:1 to 1:10, the preferable proportion is between a range of 3:1 to 1:3.
  • the process of obtention has also a great importance to obtain good results in viscosity, dispersibility in water, and stability.
  • the temperature during the said process has to be maintained with decreasing rhythm between 60° and 30°C, but the most important factor is the order and rate of addition of the different components. So, for example, it is convenient to add to the water, in the first place, a molten mixture of the alkoxylated amine together with the system of non-ionic surfactants, and to adjust the pH by means of a strong acid between 3 and 5.
  • the addition of the insoluble cationic compound is performed in a fractionated way, alternating with additions, also in a fractioned way, of the electrolyte. Small variations in the order of addition are the cause of dispersions with a very high initial viscosity or with a bad performance versus temperature variations.
  • the insoluble cationic compounds are the active softening matter, and can be selected from amongst the following groups:
  • Methyl-1-(hydrogenated tallow) amido ethyl-2-(hydrogenated tallow) imidazolinium methyl sulfate methyl-1-tallow amido ethyl-2 tallow imidazolinium methyl sulfate; methyl-l-oleyl amido ethyl-2-oleyl imidazolinium chloride; 1-ethylene bis(2-tallow, 1-methyl imidazolinium methyl sulfate).
  • Preferred compounds are methyl-1-(hydrogenated tallow) amido-ethyl-2-(hydrogenated tallow) imidazolinium methyl sulfate, marketed by Sherex Chemical Company under the designation Varisoft® 445, and 3-methylethyl-1-(hydrogenated tallow) amido ethyl-2-(hydrogenated tallow) imidazolinium methyl sulfate, marketed by Rewo Chemische under the designation Rewoquat e W7500H.
  • the alkoxylated amines have the general formula I, wherein R 1 represents an alkyl or alkenyl group having from 10 to 20 carbon atoms, those corresponding to coconut, oleic, tallow, hydrogenated tallow, and hydrogenated tallow being preferred; n is an integer from 1 to 4, value 2 being preferred, which corresponds to ethoxylated amines.
  • the values of x and y range between 10 and 50 in such a way that the total sum thereof ranges from 20 to 100, this is to say, the number of mols of ethylene oxide per amine mol must range from 20 to 100, although the preferred values of x + y range from 20 to 50.
  • Etilenox® Pulcra
  • Ethomeen® Akzo
  • Genamin@ Hoechst
  • Non-ionic surfactants have the general formula II, wherein R 2 represents an alkyl group of from 8 to 20 carbon atoms, for example, those corresponding to fatty alcohols like lauric, myristic, palmitic or stearic alchols, or the mixtures thereof, or an alkyl phenyl group with 7 to 10 carbons, as those corresponding to the alkyl phenols with 8 and 9 carbon atoms.
  • the preferred groups are those corresponding to the lauric alcohol and nonylphenol.
  • the value of n can be from 1 to 4, being the preferred value that of 2, and, therefore, the ethoxylated products. According to the invention herein, a binary system of non-ionic oxyethylenated surfactants is necessary in function of the Z value:
  • binary system nonylphenol with 30 mols of ethylene oxide together with nonylphenol with 1.5 moles of ethylene oxide, with a weight ratio ranging from 3:1 to 1:3.
  • compositions of the invention herein which are conventionally used in the field of fabric softeners, like dyes, perfumes, supplementary viscosity modifiers, emulgents, optical brighteners, antioxidants, germicides, fungicides, moisteners, etc.
  • electrolytes as salts of divalent metals with strong acids, in weight ratios ranging between 200 and 1,500 ppm.
  • electrolytes are calcium chloride and magnesium sulfate.
  • auxiliary in viscosity control are linear or branched short chain alcohols from 1 to 4 carbon atoms.
  • Isopropyl alcohols particularly, may be present in a proportion between 1 % and 4%, but not in a bigger proportion that may cause lack of stability.
  • Optional components indicated to improve the water absorbancy of the fabrics treated with the softeners are the emulsified silicones, such as DC-347, DC-346 and DC-HV490, marketed by Dow Corning. Small amounts, of an order of 0.01% to 0.3% in active matter, are employed.
  • Optical brighteners can also be employed, like, for example, derivatives of stilbene and distyrylbiphenyl, marketed by Ciba-Geigy as Tinopal®.
  • 1.5 parts of ethoxylated hydrogenated tallow amine with 25 mols of ethylene oxide per mol of amine are mixed, at a temperature of 55°C, together with 1 part of ethoxylated nonylphenol with 30 mols of ethylene oxide per mol of nonylphenol and 1 part of ethoxylated nonylphenol with 1.5 mols of ethylene oxide per mol of nonylphenol.
  • the said molten mixture is added to 70 parts of deionized water, at a temperature of 50° to 60°C, and with strong stirring. Hydrochloric acid 1 N is added until a pH of 3 to 4 is reached.
  • the sample is again placed in the refrigerator, for another four days, and then it is removed, left to stabilize for one day at room temperature, and then the viscosity is tested at 20°C.
  • the values of viscosity that have been found are:
  • Dispersibility in water is approximate and orientative.
  • a graduate cylinder is filled with a liter of water at 20°C ⁇ 5°C of temperature, and with a hardness of 20°FH.
  • 0 means total dispersion and 10 no dispersion.
  • the volume of water to which the dispersion has not arrived is measured, so that the optimal volume is that of 0 ml, and the worst one is that of 1000 ml.
  • a dispersion is prepared with the following ingredients:
  • the dispersion exhibits the following characteristics, determined according to the criteria established in example I:
  • a dispersion is prepared with the following ingredients:
  • the dispersion value exhibits the following characteristics, determined according to the criteria established in example I:
  • a dispersion is prepared with the following ingredients:
  • the dispersion exhibits the following characteristics, determined according to the criteria established in example I:
  • the dispersions described in the examples I to IV exhibit excellent viscosity, dispersibility and stability characteristics during storage and in extreme temperature conditions for their use as fabric concentrated softeners.

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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)

Claims (9)

1. Konzentrierte Weichspülerzusammensetzungen mit guter Viskosität und Dispergierbarkeit in Wasser und verbesserter Stabilität über lange Lagerdauer und gegen Temperaturschwankungen, deren wichtige Bestandteile ein kationischer Weichspüler, ein alkoxyliertes Amid und nichtionische, oberflächenaktive Substanzen bilden, dadurch gekennzeichnet, daß die Zusammensetzungen enhalten:
A. 10 bis 20 Gew.-% einer wasserunlöslichen, kationischen Verbindung mit weichmachender Wirkung für Gewebe oder einer Mischung solcher Verbindungen,
B. 0,1 bis 3 Gew.% eines tertiären Amids oder dessen Ammoniumsalzes der allgemeinen Formel:
Figure imgb0019
worin R1 eine Alkyl- oder Alkenylgruppe mit 10 bis 20 Kohlenstoffatomen ist, n eine ganze Zahl von 1 bis 4 ist und x und y Zahlen zwischen 10 und 50 darstellen, deren Summe 20 bis 100 beträgt (x + y = 20 bis 100).
C. 0,5 b is 5 Gew.-% einer Mischung aus zwei nichtionischen, oberflächenaktiven Substanzen, die zu folgenden Gruppen gehören:
1.-alkoxylierte C8- bis C2o-Fettalkohole oder alkoxylierte C7- bis Clo-Alkylphenole mit einer Molanzahl eines Ci- bis C4-Alkylenoxids von 25 bis 75 pro Mol Alkohol oder Phenol,
ii.-alkoxylierte C8- bis C20-Fettalkohole oder alkoxylierte C7- bis C10-Alkylphenole mit einer Molanzahl eines C1- bis C4-Alkylenoxids von 1 bis 5,

so daß das Gewichtsverhältnis dieser Mischung aus nichtionischen, oberflächenaktiven Substanzen zwischen 10:1 und 1:10 liegt,

wobei die genannten Bestandteile in Wasser bei einem pH-Wert zwischen 3 und 5 gelöst oder dispergiert werden.
2. Zussamensetzungen nach Anspruch 1, dadurch gekennzeichnet, daß der wasserunlösliche, kationische Bestandteil oder die wasserunlöslichen, kationischen Bestandteile aus einer der folgenden Gruppen ausgewählt sind:
A. Nichtzyklische, quaternäre Ammoniumsalze der allgemeinen Formel:
Figure imgb0020
worin R3 und R4 C10- bis C20-Alkyl- oder -Alkenylgruppen, R5 und R6 kurzkettige C1- bis C4-Alkenylgruppen sind, und A- das Anion einer starken Säure darstellt,
B. quaternäre Imidazoliniumsalze de allgemeinen Formeln:
Figure imgb0021
Figure imgb0022
worin R7, R8, Rg und R10 gesättigte ode ungesättigte Alkylgruppen mit Ketten von 10 bis 20 Kohlenstoffatomen sind und A- das Anion einer starken Säure ist.
3. Zusammensetzungen nach einem der Ansprüche 1 und 2, dadurch gekennzeichnet, daß der wasserunlösliche, kationische Bestandteile oder die wasserunlöslichen, kationischen Bestandteile Di(hydrierter Talg) dimethylammoniumchlorid und/oder 3-Methyl-1-(hydrierter Talg) amidoethyl-2-(hydrierter Talg) imidazolmethylsulfat ist/sind.
4. Zusammensetzungen nach einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, daß das tertiäre alkoxylierte Amin ethoxyliertes (hydrierter Talg) Amin mit 25 Molen Ethylenoxid oder ethoxyliertes (hydrierter Talg) Amin mit 50 Molen Ethylenoxid ist.
5. Zusammensetzungen nach einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, daß der Bestandteil der hoch alkoxylierten nichtionischen oberflächenaktiven Substanz aus der Gruppe aus ethoxyliertem Nonylphenol mit 30 Molen Ethylenoxid oder ethoxyliertem Laurinalkohol mit 50 Molen Ethylenoxid ausgewählt wird und die nichtionische oberflächenaktive Substanz mit geringer Alkoxylierung aus der Gruppe aus ethoxyliertem Nonylphenol mit 1,5 Molen Ethylenoxid oder ethoxyliertem Laurinalkohol mit 2,7 Molen Ethylenoxid ausgewählt wird.
6. Zusammensetzungen nach einem der vorangeganenen Ansprüche, dadurch gekennzeichnet, daß ein Elektrolyt, welcher zu den Salzen der zweiwertigen Metalle mit starken Säuren gehört, als Mittel zur Verbesserung des Viskositätswerts in einem Gewichtsverhältnis von 0,02% bis 0,15%, bezogen auf das Gesamtgewicht der Zusammensetzung, zugegeben wird.
7. Zusammensetzungen nach einem der vorangegangenen Ansprüche, dadurch gekennzeichnet, daß sie die folgenden Bestandteile aufweisen:
A. 11 bis 16 Gew.-% eines wasserunlöslichen, kationischen Weichmachers oder einer Mischung solcher Weichmacher
B. 0,5 bis 1,5 Gew.-% eines alkoxylierten, tertiären Amins der allgemeinen Formel I mit 20 bis 100 Molen Alkylenoxid pro Mol Amin,
C. 1 bis 3, Gew.-% einer Mischung aus zwei nichtionischen, oberflächenaktiven Substanzen, die zu den folgenden Gruppen gehören:
i.-alkoxylierte C8- bis C20-Fettalkohole oder alkoxylierte C,- bis C10-Alkylphenole mit einer Molanzahl eines Ci- bis C4-Alkylenoxids von 25 bis 75 pro Mol Alkohol oder Phenol,
ii.-alkoxylierte Ca- bis C20-Fettalkohole oder alkoxylierte C7- bis C10-Alkylphenole mit einer Anzahl an C1- bis C4-Alkylenoxidmolen von 1 bis 5 pro Mol Alkohol oder Phenol,

wobei das Gewichtsverhältnis der beiden nichtionischen, oberflächenaktiven Substanzen zwischen 3:1 und 1:3 liegt,
D. 0,03 bis 0,15 Gew.-% eines Elektrolyten, welcher zu den Salzen der zweiwertigen Metalle mit starken Säuren gehört,

wobei die genannten Bestandteile in Wasser bei einem pH-Wert zwischen 3,5 und 4,5 gelöst oder dispergiert werden.
8. Verfahren zur Herstellung der Zusammensetzungen nach einem der vorangeganenen Ansprüche, dadurch gekennzeichnet, daß in einem ersten Schritt eine flüssige Mischung aus nichtionischen Bestandteilen und dem alkoxylierten Amin unter Rühren zu entionisiertem Wasser bei einer Temperatur zwsichen 50°C und 60°C sowie eine starke Säure mit einem pH-Wert zwischen 3 und 5 zugegeben wird, und in einem zweiten Schritt eine fraktionierte Zugabe des wasserunlöslichen kationischen Bestandteils im Wechsel mit fraktionierten Zugaben des Elektrolyten unter Rühren bei einer Temperatur zwischen 45°C und 55°C erfolgt, wobei die Herstellung de Verbindung nach Abkühlen auf 30°C bis 40°C und Einstellen des pH-Werts auf 3 bis 5 unter Zugabe der wahlweisen Bestandteile beendet wird.
9. Verfahren nach Anspruch 8, gekennzeichnet durch die Zugabe der wasserunlöslichen, kationischen Verbindung in zwei Fraktionen, wobei die erste 70% des Gesamtanteils und die zweite 30% des Gesamtanteils ausmacht, im Wechsel mit der Zugabe des Elektrolyten ebenfalls in zwei Fraktionen, wobei die erste 30% des Gesamtanteils und die zweite 70% des Gesamtanteils ausmacht.
EP19830105693 1983-06-10 1983-06-10 Stabile konzentrierte wässrige Dispersionen von wasserunlöslichen kationischen Verbindungen und deren Zubereitung Expired EP0128231B1 (de)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP19830105693 EP0128231B1 (de) 1983-06-10 1983-06-10 Stabile konzentrierte wässrige Dispersionen von wasserunlöslichen kationischen Verbindungen und deren Zubereitung
DE8383105693T DE3373492D1 (en) 1983-06-10 1983-06-10 Stable concentrated aqueous dispersions of water-insoluble cationic compounds and preparation thereof
ES523600A ES8500988A1 (es) 1983-06-10 1983-06-27 Procedimiento para la obtencion de suavizantes concentrados para textiles

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EP19830105693 EP0128231B1 (de) 1983-06-10 1983-06-10 Stabile konzentrierte wässrige Dispersionen von wasserunlöslichen kationischen Verbindungen und deren Zubereitung

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB8410322D0 (en) * 1984-04-19 1984-05-31 Unilever Plc Aqueous concentrated fabric softening composition
DE3603579A1 (de) * 1986-02-06 1987-08-13 Henkel Kgaa Verwendung ethoxylierter fettamine als loesungsvermittler
US5145608A (en) * 1986-02-06 1992-09-08 Ecolab Inc. Ethoxylated amines as solution promoters
DE3643934A1 (de) * 1986-12-22 1988-06-23 Henkel Kgaa Verwendung ausgewaehlter alkyl- und/oder alkenyl-diethanolaminverbindungen als loesungsvermittler fuer schaumarme tenside
JPH06506992A (ja) * 1991-04-30 1994-08-04 ザ、プロクター、エンド、ギャンブル、カンパニー 置換イミダゾリンおよび高度にエトキシル化された化合物を含む布帛柔軟化剤
MY108928A (en) * 1992-12-22 1996-11-30 Colgate Palmolive Co Liquid fabric softening composition containing amidoamine softening compound
GB0014891D0 (en) * 2000-06-16 2000-08-09 Unilever Plc Fabric softening compositions
US8916512B2 (en) * 2010-06-21 2014-12-23 Basf Se Surfactant component and a composition including the same
KR102268819B1 (ko) 2013-03-14 2021-06-25 바스프 에스이 핫 멜트 접착제 및 그의 형성 방법
US10487292B2 (en) 2016-08-31 2019-11-26 The Procter & Gamble Company Fabric enhancer composition
US20190264136A1 (en) * 2018-02-28 2019-08-29 The Procter & Gamble Company Fabric enhancer composition

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4157307A (en) * 1978-08-07 1979-06-05 The Procter & Gamble Company Liquid fabric softener
US4233164A (en) * 1979-06-05 1980-11-11 The Proctor & Gamble Company Liquid fabric softener
ATE13562T1 (de) * 1981-01-16 1985-06-15 Procter & Gamble Textilbehandlungsmittel.
US4383063A (en) * 1981-04-09 1983-05-10 E. I. Du Pont De Nemours And Company Polyvinyl alcohol based size composition
BE888535A (fr) * 1981-04-23 1981-08-17 Lesieur Cotelle Compositions adoucissantes liquides pour textiles,
DE3135013A1 (de) * 1981-09-04 1983-03-24 Hoechst Ag, 6000 Frankfurt "waescheweichspuelmittel"

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DE3373492D1 (en) 1987-10-15
ES523600A0 (es) 1984-11-01
ES8500988A1 (es) 1984-11-01

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