EP0293955A2 - Composés d'isopropylester ammonium quaternaires comme compositions de traitement pour les fibres et les matières textiles - Google Patents
Composés d'isopropylester ammonium quaternaires comme compositions de traitement pour les fibres et les matières textiles Download PDFInfo
- Publication number
- EP0293955A2 EP0293955A2 EP88200819A EP88200819A EP0293955A2 EP 0293955 A2 EP0293955 A2 EP 0293955A2 EP 88200819 A EP88200819 A EP 88200819A EP 88200819 A EP88200819 A EP 88200819A EP 0293955 A2 EP0293955 A2 EP 0293955A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- composition according
- softener
- fabric
- mixtures
- short
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- 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
Definitions
- the present invention relates to textile treatment compositions.
- textile treatment compositions for use in the rinse cycle of a textile laundering operation to provide fabric softening/static control benefits, the compositions being characterized by excellent storage stability and viscosity characteristics and biodegradability.
- the compositions herein can also be used to treat fabrics in hot air clothes dryers, and in hair conditioner compositions.
- rinse-added fabric softening compositions contain, as the active softening component, substantially water-insoluble cationic materials having two long alkyl chains. Typical of such materials are di-stearyl di-methyl ammonium chloride and imidazolinium compounds substituted with two stearyl groups.
- Cationic softener materials are normally supplied by the manufacturer in the form of a slurry containing about 70%-80% of active material in an organic liquid such as isopropanol, sometimes containing a minor amount of water (up to about 10%).
- Retail fabric softening compositions are then prepared by dispersion of the softener slurry in warm water under carefully controlled conditions.
- the physical form and dispersibility constraints of these industrial concentrates are such as to preclude their direct use by the domestic consumer; indeed, they can pose severe processing problems even for the industrial supplier of retail fabric softening compositions.
- European Patent 0,018,039, Clint, et al, March 7, 1984, relates to hydrocarbons plus soluble cationic or nonionic surfactants in softener concentrates to improve viscosity and stability characteristics.
- U.S. Patent 4,454,049 MacGilp, et al, June 12, 1984 discloses liquid textile treatment compositions in the form of isotropic solutions comprising water-insoluble di-C16-C24 optionally hydroxy-substituted alkyl, alkaryl or alkenyl cationic fabric softeners, at least about 70% of the fabric softener consisting of one or more components together having a melting completion temperature of less than about 20°C, a water-insoluble nonionic extender, especially C10-C40 hydrocarbons or esters of mono- or polyhydric alcohols with C8-C24 fatty acids, and a water-miscible organic solvent.
- the concentrates have improved formulation stability and dispersibility, combined with excellent fabric softening characteristics.
- U.S. Patent 4,476,031, Ooms, Oct. 9, 1984 teaches ethoxylated amines, or protonated derivatives thereof, in combination with ammonium, imadazolinium, and the like materials.
- alkoxylated amines, as a class, in softener compositions is known (see, for example, German Patent Applications Nos. 2829022 and 1,619,043 and U.S. Patent Nos. 4,076,632 and 4,157,307).
- fabric softener concentrates which contain a mixture of a fatty quaternary ammonium salt having at least one C8-C30 alkyl substituent and an oil or substantially water-insoluble compound having oily/fatty properties.
- the concentrates are said to be easily dispersed/emulsified in cold water to form fabric softening compositions.
- Concentrated dispersions of softener material can be prepared as described in European Patent Application No. 406 and U.K. Patent No. 1,601,360 by incorporating certain nonionic adjunct softening materials therein.
- each R substituent is a short-chain (C1-C6, preferably C1-C3) alkyl or hydroxyalkyl group, e.g., methyl (most preferred), ethyl, propyl, hydroxyethyl, and the like, or mixtures thereof; each R′ is a long-chain hydrocarbyl substituent, e.g., C13-C17, preferably C15 alkyl, or mixtures thereof; and R ⁇ is a short-chain (C1-C4) hydrocarbyl substituent, especially methyl.
- the counterion X ⁇ is not critical herein, and can be, for example, halide, methylsulfate, and the like. It will be understood that substituents R, R′ and R ⁇ may optionally be substituted with various groups such as alkoxyl, hydroxyl, or can be branched, but such materials are not preferred herein.
- the preferred compounds can be considered to be quaternized di-esters of di-isopropanol amines.
- ester moieties lend biodegradability to these compounds, whereas the chain branching of the isopropyl moiety provides sufficient hydrolytic stability that the compounds can be stably formulated as liquid compositions, under the conditions disclosed hereinafter.
- the desirable viscosity characteristics of the compounds which allows them to be formulated as concentrates are entirely unexpected. Since the compounds are cationic, they provide not only fiber and fabric softness, but also anti-static benefits.
- the present invention encompasses liquid fabric softening and antistatic compositions, comprising: a liquid carrier; and at least about 1% by weight of a fabric softener compound of the above-disclosed formula dissolved or, preferably, dispersed in said carrier.
- Such liquid compositions are most preferably formulated at a pH of from about 1.5 to about 5.0 to provide good storage stability.
- Such compositions will typically comprise from about 3% to about 15% by weight of the softener compound.
- the preferred liquid compositions herein have the softener compound present as particles dispersed in the carrier.
- the particles are preferably sub-micron size, generally having average diameters in the range of about 0.15-0.45 microns.
- Such particle dispersions can optionally be stabilized with emulsifiers.
- liquid compositions herein are substantially free (generally, less than 1%) of free (i.e., unprotonated) amines, since free amines can catalyze decomposition of the softener compounds, on storage. However, if minor amounts of amines are present, they should be protonated with acid during formulation of the compositions. Strong acids, such as H3PO4 and HCl, can be used for this purpose.
- the low viscosities exhibited by dispersions of particles of the compounds herein allows them to be formulated as water-dilutable fabric softener "high concentrates" which contain from about 16% to about 25% by weight of the fabric softener compound.
- high concentrates are conveniently packaged in pouches, which can be diluted with water to "single-strength" softeners (typically, 3-5% concentration of softener active) by the user.
- the compounds herein can also be formulated as solids, for example, in combination with particulate carriers as particulate fabric softening and antistatic compositions.
- particulate carriers as particulate fabric softening and antistatic compositions.
- the pH and presence or absence of amines are, of course, not as critical as with the liquid compositions, since stability to hydrolysis on storage is not so problematic.
- solid compositions herein have the compounds releasably affixed to sheet materials to provide fabric softening and antistatic compositions in sheet form which can be used in hot air clothes dryers.
- the invention also encompasses a method of softening fibers (including hair) or fabrics, or imparting an antistatic finish thereto, comprising contacting said fibers or fabrics with a compound of the above-disclosed type.
- the compounds used as the active softener and antistatic ingredient in the practice of this invention are prepared using standard reaction chemistry.
- an amine of the formula RN(CH2CHR ⁇ OH)2 is esterified at both hydroxyl groups with an acid chloride of the formula R′C(O)Cl, then quaternized with an alkyl halide, RX, to yield the desired reaction product (wherein R, R′ and R ⁇ are as defined in the above structural formula).
- RX alkyl halide
- stable liquid compositions herein are formulated at a pH in the range of about 1.5 to about 5.0, preferably about pH 3 ⁇ 0.5.
- the pH can be adjusted with standard acids, e.g., HCl, HBr, and the like; H3PO4 is preferred.
- liquid compositions herein should be substantially free (1%, or less, preferably 0.3%) of amines. While many fully-formulated fabric softener compositions comprise mixtures of various softener compounds, the amine softeners sometimes used in such art-disclosed compositions are preferably not used in the liquid compositions of this invention, since they can catalyze hydrolysis and thereby reduce storage stability. However, it should be appreciated that the liquid and solid compositions herein can optionally contain non-amine softener and antistatic materials, e.g., standard softener "quats" such as ditallow dimethyl ammonium chloride (“DTDMAC ⁇ ), C14-C18 imidazoliniums, etc., as auxiliary softener/antistat ingredients. Such optional ingredients can typically comprise 1%-10% of the present compositions.
- non-amine softener and antistatic materials e.g., standard softener "quats” such as ditallow dimethyl ammonium chloride (“DTDMAC ⁇ ), C14-C18 imidazolini
- the liquid compositions herein comprise a liquid carrier, which is typically water or a mixture of water and an alcohol such as ethanol or iso-propanol (typically 0.5-2.0%alcohol).
- a liquid carrier typically water or a mixture of water and an alcohol such as ethanol or iso-propanol (typically 0.5-2.0%alcohol).
- the softener compounds used in this invention are insoluble in such water-based carriers and, thus, are present as a dispersion of fine particles therein. These particles are, as noted above, preferably sub-micron in size and are conveniently prepared by high-shear mixing which disperses the compounds as fine particles. Preparation of a preferred dispersion is disclosed in detail in Example II, hereinafter. Again, since the compounds are hydrolytically labile, care should be taken to avoid the presence of base and to keep the processing temperatures in the range of about 65 to about 85°C, preferably 65-75°C.
- the particulate dispersions of the foregoing type can optionally be stabilized against settling by means of standard, non-base emulsifiers, especially nonionics such as the C14-18 ethoxylates (E08 ⁇ 15), typically used at concentrations of 0.1-2%, according to known practice in the formulation of liquid DTDMAC fabric softener dispersions.
- nonionics such as the C14-18 ethoxylates (E08 ⁇ 15), typically used at concentrations of 0.1-2%, according to known practice in the formulation of liquid DTDMAC fabric softener dispersions.
- fabrics or fibers are contacted with from about 3.0 g to about 9.0 g (per 3.5 kg of fiber or fabric being treated) of the compounds herein in an aqueous bath, or in a hot air clothes dryer.
- the amount used is at the discretion of the user, depending on fiber or fabric type, degree of softness desired, and the like.
- about 120 mls. of a 5% dispersion are used in a 25 l laundry rinse bath to soften and provide antistatic benefits to a 3.5 kg load of mixed fabrics.
- the reaction mixture is cooled to room temperature and diluted with chloroform (1500 mL).
- the chloroform solution of product is placed in a separatory funnel (4 L) and washed with sat. NaCl, dil. Ca(OH)2, 50% K2CO3, (3 times)*, and, finally, sat. NaCl.
- the organic layer is collected and dried over MgSO4 and filtered. Solvents are removed via rotary evaporation. Final drying is done under high vacuum (0.25 mm Hg). *Note: 50% K2CO3 layer will be below chloroform layer.
- the nonhydrolytic preparation of the composition of Example II is carried out as follows.
- the softener compound and the isopropyl alcohol are mixed and warmed (80 to 85°C) to form a fluidized "melt".
- the melt is then poured into the water (65 to 75°C) with high shear mixing (7000 rpm; 20-25 minutes) to submicronize the softener particles.
- the dye and minors are added, and the pH is adjusted with H3PO4.
- the resulting dispersion has a viscosity of about 40 centipoise and is used in standard fashion as a through-the-rinse fabric softener. All liquid compositions herein are prepared in substantially the same manner.
- the present compositions can be supplemented by all manner of optional components conventionally used in textile treatment compositions, for example, colorants, perfumes, preservatives, optical brighteners, opacifiers, viscosity modifiers, fabric conditioning agents, surfactants, stabilizers such as guar gum and polyethylene glycol, antishrinkage agents, antiwrinkle agents, fabric crisping agents, spotting agents, soil-release agents, germicides, fungicides, antioxidants such as butylated hydroxy toluene, anticorrosion agents, and the like.
- optional components conventionally used in textile treatment compositions for example, colorants, perfumes, preservatives, optical brighteners, opacifiers, viscosity modifiers, fabric conditioning agents, surfactants, stabilizers such as guar gum and polyethylene glycol, antishrinkage agents, antiwrinkle agents, fabric crisping agents, spotting agents, soil-release agents, germicides, fungicides, antioxidants such as butylated
- materials such as DTDMAC, the C16-C18 dialkylimidazoliniums, polydimethylsiloxanes, glycerol monostearate, and, as noted above, emulsifiers, especially ethoxylated nonionics, can optionally be used in the present compositions.
- amines such as TAMET (C18H37N[CH2CH2OH]2) can be present in relatively small amounts (typically 0.3-0.5%) if in the protonated form.
- Solid carrier materials can be used in place of liquids.
- the softener compounds can be adsorbed on particulate solids such as potassium sulfate, micronized silica, and the like, and added to a laundry rinse bath.
- the softeners can be releasably padded onto a sheet (e.g., paper toweling, nonwoven fabric, or the like) and tumbled with damp fabrics in a hot-air clothes dryer, in the manner of the BOUNCE brand dryer-added product known in commercial practice.
- a sheet e.g., paper toweling, nonwoven fabric, or the like
- tumbled with damp fabrics in a hot-air clothes dryer, in the manner of the BOUNCE brand dryer-added product known in commercial practice.
- such solid-form compositions will comprise 80-99% carrier and 1-20% softener.
- a dryer-additive sheet is prepared by warming 5 g. of the softener compound of Example I in 6 g. isopropanol to prepare a melt in the manner of Example II.
- the melt is evenly spread onto and into an ordinary, disposable paper hand towel (20 cm x 20 cm) and allowed to dry.
- the impregnated towel is commingled and tumbled with wet fabrics (5 kg load of fabrics, dry weight basis) in a standard hot air clothes dryer until the fabrics are dry, to provide a soft, antistatic finish.
- a liquid fabric softener as a particulate, sub-micron dispersion is prepared according to Example II, and has the following composition:
- a particulate softener comprises the following.
- Example V The composition of Example V is prepared by co-melting the softener compound, ethoxylated alcohol, and an equal weight of ethanol, with gentle warming, then spraying the melt uniformly onto the particulate silica/sodium sulfate.
- a high concentrate liquid fabric softener comprises the following.
- Example VI The composition of Example VI is prepared in the manner of Example II, as sub-micron particles suspended in liquid. In a convenient mode, the composition is packaged in a simple plastic pouch, which is opened and poured into 4X its volume of water prior to use to prepare a "single strength" softener composition, thereby saving on packaging and shipping costs and storage space.
- the single strength composition prepared from the concentrate of Example VI can be applied to human or animal hair, typically after shampooing, to provide a soft, lubricious feel.
- di-isopropanol amine feedstocks used herein may contain varying amounts of mono-isopropanol amines and tri-isopropanol amines.
- the commercial-grade ester reaction products will comprise, in addition to the di-ester softeners, various amounts of mono- and tri-esters.
- the preferred compounds herein function well at temperatures lower than many art-disclosed fabric softeners, making them more useful in hot air clothes dryers, as well as performing well when fabrics are line-dried.
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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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT88200819T ATE84566T1 (de) | 1987-05-01 | 1988-04-27 | Quaternaere isopropylesterammonium-verbindungen als faser- und gewebebehandlungsmittel. |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US4597687A | 1987-05-01 | 1987-05-01 | |
US45976 | 1987-05-01 |
Publications (3)
Publication Number | Publication Date |
---|---|
EP0293955A2 true EP0293955A2 (fr) | 1988-12-07 |
EP0293955A3 EP0293955A3 (en) | 1989-07-05 |
EP0293955B1 EP0293955B1 (fr) | 1993-01-13 |
Family
ID=21940877
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP88200819A Expired - Lifetime EP0293955B1 (fr) | 1987-05-01 | 1988-04-27 | Composés d'isopropylester ammonium quaternaires comme compositions de traitement pour les fibres et les matières textiles |
Country Status (4)
Country | Link |
---|---|
EP (1) | EP0293955B1 (fr) |
AT (1) | ATE84566T1 (fr) |
DE (1) | DE3877422T2 (fr) |
GB (1) | GB8810310D0 (fr) |
Cited By (32)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0413249A1 (fr) * | 1989-08-12 | 1991-02-20 | Witco Surfactants GmbH | Adoucissant pour textile |
WO1995004802A1 (fr) * | 1993-08-06 | 1995-02-16 | The Procter & Gamble Company | Compositions antistatiques et d'adoucissement des tissus activees lors du sechage en machine et contenant des composes biodegradables non satures |
EP0643038A2 (fr) * | 1993-07-15 | 1995-03-15 | Aranor, S.A. | Agents de surface polyfonctionels cationiques, compositions les contenant, procédé de préparation et usages |
WO1995025713A1 (fr) | 1994-03-18 | 1995-09-28 | Henkel Kommanditgesellschaft Auf Aktien | Procede de production d'esters quaternaires |
EP0773018A1 (fr) | 1995-11-09 | 1997-05-14 | Henkel Kommanditgesellschaft auf Aktien | Emulsions cosmétiques et/ou pharmaceutiques |
US5660759A (en) * | 1994-05-06 | 1997-08-26 | Henkel Kommanditgesellschaft Auf Aktien | Cationic formulations for oiling leathers and skins |
US5750490A (en) * | 1994-01-31 | 1998-05-12 | Henkel Kommanditgesellschaft Auf Aktien | Detergent mixtures |
US5783534A (en) * | 1993-11-20 | 1998-07-21 | Henkel Kommanditgesellschaft Auf Aktien | Process for the production of solid esterquats |
US5869716A (en) * | 1994-03-18 | 1999-02-09 | Henkel Kommanditgesellschaft Auf Aktien | Process for the production of esterquats |
US6022845A (en) * | 1995-11-03 | 2000-02-08 | The Procter & Gamble Co. | Stable high perfume, low active fabric softener compositions |
US6261346B1 (en) | 1996-11-28 | 2001-07-17 | Cognis Deutschland Gmbh | Method for protecting metal surfaces against corrosion in liquid or gaseous media |
US6384009B1 (en) | 1998-09-22 | 2002-05-07 | Cognis Deutschland Gmbh | Use of alkoxylated carboxylic acid esters for reducing viscosity of aqueous surfactant systems |
US6402976B1 (en) | 1996-08-16 | 2002-06-11 | Henkel Kommanditgesellschaft Auf Aktien | Textile finishing agent |
US6420330B1 (en) | 1997-09-24 | 2002-07-16 | Cognis Deutschland Gmbh | Use of quaternary carboxylic acid alkanolamine ester salts as microbicide agents |
US6602838B1 (en) | 1998-07-07 | 2003-08-05 | Cognis Deutschland Gmbh & Co. Kg | Hand dishwashing liquid comprising an alkoxylated carboxylic acid ester |
EP0640121B2 (fr) † | 1992-05-12 | 2003-08-27 | The Procter & Gamble Company | Compositions concentrees assouplissantes liquides contenant des produits assouplissants biodegradables |
WO2006113658A3 (fr) * | 2005-04-18 | 2008-01-31 | Procter & Gamble | Compositions pour l'entretien des textiles diluees contenant des agents epaississants et compositions pour l'entretien des textiles destinees a etre utilisees en presence de tensioactifs anioniques |
US20110203975A1 (en) * | 2008-11-07 | 2011-08-25 | Clariant Finance (Bvi) Limited | Mixture of an Amine Alkoxylate Ester and a Quaternary Ammonium Compound as a Collector for Minerals Containing Silicate |
WO2011123733A1 (fr) | 2010-04-01 | 2011-10-06 | The Procter & Gamble Company | Produit assouplissant thermiquement stable |
WO2011120822A1 (fr) | 2010-04-01 | 2011-10-06 | Evonik Degussa Gmbh | Composition active d'adoucissant pour étoffe |
WO2011123284A1 (fr) | 2010-04-01 | 2011-10-06 | The Procter & Gamble Company | Produit assouplissant thermostable |
US8361953B2 (en) | 2008-02-08 | 2013-01-29 | Evonik Goldschmidt Corporation | Rinse aid compositions with improved characteristics |
US8507425B2 (en) | 2010-06-29 | 2013-08-13 | Evonik Degussa Gmbh | Particulate fabric softener comprising ethylenediamine fatty acid amides and method of making |
US8563499B2 (en) | 2010-04-01 | 2013-10-22 | Evonik Degussa Gmbh | Fabric softener active composition |
US8883712B2 (en) | 2010-04-28 | 2014-11-11 | Evonik Degussa Gmbh | Fabric softening composition |
US8883713B2 (en) | 2012-01-30 | 2014-11-11 | Evonik Industries Ag | Fabric softener active composition |
US9441187B2 (en) | 2012-05-07 | 2016-09-13 | Evonik Degussa Gmbh | Fabric softener active composition and method for making it |
US9801797B2 (en) | 2013-03-22 | 2017-10-31 | Evonik Degussa Gmbh | Formulation comprising ester quats based on isopropanolamine |
EP2582780B1 (fr) | 2010-06-17 | 2018-01-24 | Henkel AG & Co. KGaA | Adoucissant textile épaissi |
US10011806B2 (en) | 2013-11-05 | 2018-07-03 | Evonik Degussa Gmbh | Method for making a tris-(2-hydroxyethyl)-methylammonium methylsulfate fatty acid ester |
US10113137B2 (en) | 2014-10-08 | 2018-10-30 | Evonik Degussa Gmbh | Fabric softener active composition |
US10815191B2 (en) | 2014-09-22 | 2020-10-27 | Evonik Operations Gmbh | Formulation comprising ester quats based on isopropanolamine and tetrahydroxypropyl ethylenediamine |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP4360617A1 (fr) | 2022-10-31 | 2024-05-01 | Evonik Operations GmbH | Formulation comprenant des esterquats à base de trialcanolamines |
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GB8410320D0 (en) * | 1984-04-19 | 1984-05-31 | Unilever Plc | Aqueous fabric softening composition |
GB8414944D0 (en) * | 1984-06-12 | 1984-07-18 | Ici Plc | Fabric conditioners |
DE3608093A1 (de) * | 1986-03-12 | 1987-09-17 | Henkel Kgaa | Konfektioniertes textilweichmacher-konzentrat |
DE3612479A1 (de) * | 1986-04-14 | 1987-10-15 | Henkel Kgaa | Waessriges konzentriertes textilweichmachungsmittel |
-
1988
- 1988-04-27 AT AT88200819T patent/ATE84566T1/de not_active IP Right Cessation
- 1988-04-27 DE DE8888200819T patent/DE3877422T2/de not_active Expired - Fee Related
- 1988-04-27 EP EP88200819A patent/EP0293955B1/fr not_active Expired - Lifetime
- 1988-04-29 GB GB888810310A patent/GB8810310D0/en active Pending
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EP0018039A1 (fr) | 1979-04-21 | 1980-10-29 | THE PROCTER & GAMBLE COMPANY | Composition adoucissante pour tissus |
US4339391A (en) | 1979-07-14 | 1982-07-13 | Hoechst Aktiengesellschaft | Quaternary ammonium compounds |
US4439330A (en) | 1981-01-16 | 1984-03-27 | The Procter & Gamble Company | Textile treatment compositions |
US4476031A (en) | 1981-01-16 | 1984-10-09 | The Procter & Gamble Company | Textile treatment compositions |
EP0059502A1 (fr) | 1981-02-28 | 1982-09-08 | THE PROCTER & GAMBLE COMPANY | Compositions pour le traitement de matières textiles |
US4422949A (en) | 1981-03-07 | 1983-12-27 | The Procter & Gamble Company | Textile treatment compositions and preparation thereof |
US4454049A (en) | 1981-11-14 | 1984-06-12 | The Procter & Gamble Company | Textile treatment compositions |
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US5180508A (en) * | 1989-08-12 | 1993-01-19 | Rewo Chemische Werke Gmbh | Fabric softener rinsing agents |
US5364542A (en) * | 1989-08-12 | 1994-11-15 | Rewo Chemische Werke Gmbh | Fabric softener rinsing agents |
EP0413249A1 (fr) * | 1989-08-12 | 1991-02-20 | Witco Surfactants GmbH | Adoucissant pour textile |
EP0640121B2 (fr) † | 1992-05-12 | 2003-08-27 | The Procter & Gamble Company | Compositions concentrees assouplissantes liquides contenant des produits assouplissants biodegradables |
EP0643038A2 (fr) * | 1993-07-15 | 1995-03-15 | Aranor, S.A. | Agents de surface polyfonctionels cationiques, compositions les contenant, procédé de préparation et usages |
EP0643038A3 (fr) * | 1993-07-15 | 1995-05-31 | Aranor Sa | Agents de surface polyfonctionels cationiques, compositions les contenant, procédé de préparation et usages. |
WO1995004802A1 (fr) * | 1993-08-06 | 1995-02-16 | The Procter & Gamble Company | Compositions antistatiques et d'adoucissement des tissus activees lors du sechage en machine et contenant des composes biodegradables non satures |
US5783534A (en) * | 1993-11-20 | 1998-07-21 | Henkel Kommanditgesellschaft Auf Aktien | Process for the production of solid esterquats |
US5750490A (en) * | 1994-01-31 | 1998-05-12 | Henkel Kommanditgesellschaft Auf Aktien | Detergent mixtures |
WO1995025713A1 (fr) | 1994-03-18 | 1995-09-28 | Henkel Kommanditgesellschaft Auf Aktien | Procede de production d'esters quaternaires |
US5869716A (en) * | 1994-03-18 | 1999-02-09 | Henkel Kommanditgesellschaft Auf Aktien | Process for the production of esterquats |
US5660759A (en) * | 1994-05-06 | 1997-08-26 | Henkel Kommanditgesellschaft Auf Aktien | Cationic formulations for oiling leathers and skins |
US6022845A (en) * | 1995-11-03 | 2000-02-08 | The Procter & Gamble Co. | Stable high perfume, low active fabric softener compositions |
EP0773018A1 (fr) | 1995-11-09 | 1997-05-14 | Henkel Kommanditgesellschaft auf Aktien | Emulsions cosmétiques et/ou pharmaceutiques |
US6402976B1 (en) | 1996-08-16 | 2002-06-11 | Henkel Kommanditgesellschaft Auf Aktien | Textile finishing agent |
US6261346B1 (en) | 1996-11-28 | 2001-07-17 | Cognis Deutschland Gmbh | Method for protecting metal surfaces against corrosion in liquid or gaseous media |
US6420330B1 (en) | 1997-09-24 | 2002-07-16 | Cognis Deutschland Gmbh | Use of quaternary carboxylic acid alkanolamine ester salts as microbicide agents |
US6602838B1 (en) | 1998-07-07 | 2003-08-05 | Cognis Deutschland Gmbh & Co. Kg | Hand dishwashing liquid comprising an alkoxylated carboxylic acid ester |
US6384009B1 (en) | 1998-09-22 | 2002-05-07 | Cognis Deutschland Gmbh | Use of alkoxylated carboxylic acid esters for reducing viscosity of aqueous surfactant systems |
WO2006113658A3 (fr) * | 2005-04-18 | 2008-01-31 | Procter & Gamble | Compositions pour l'entretien des textiles diluees contenant des agents epaississants et compositions pour l'entretien des textiles destinees a etre utilisees en presence de tensioactifs anioniques |
US8361953B2 (en) | 2008-02-08 | 2013-01-29 | Evonik Goldschmidt Corporation | Rinse aid compositions with improved characteristics |
US20110203975A1 (en) * | 2008-11-07 | 2011-08-25 | Clariant Finance (Bvi) Limited | Mixture of an Amine Alkoxylate Ester and a Quaternary Ammonium Compound as a Collector for Minerals Containing Silicate |
US9027757B2 (en) * | 2008-11-07 | 2015-05-12 | Clariant Finance (Bvi) Limited | Mixture of an amine alkoxylate ester and a quaternary ammonium compound as a collector for minerals containing silicate |
CN102834496B (zh) * | 2010-04-01 | 2014-01-15 | 赢创德固赛有限公司 | 织物柔软剂活性组合物 |
US8563499B2 (en) | 2010-04-01 | 2013-10-22 | Evonik Degussa Gmbh | Fabric softener active composition |
US8569224B2 (en) | 2010-04-01 | 2013-10-29 | Evonik Degussa Gmbh | Fabric softener active composition |
WO2011123733A1 (fr) | 2010-04-01 | 2011-10-06 | The Procter & Gamble Company | Produit assouplissant thermiquement stable |
JP2013524036A (ja) * | 2010-04-01 | 2013-06-17 | ザ プロクター アンド ギャンブル カンパニー | 熱安定性柔軟仕上げ剤 |
JP2013525617A (ja) * | 2010-04-01 | 2013-06-20 | ザ プロクター アンド ギャンブル カンパニー | 熱安定性柔軟仕上げ剤 |
US8183199B2 (en) | 2010-04-01 | 2012-05-22 | The Procter & Gamble Company | Heat stable fabric softener |
WO2011123284A1 (fr) | 2010-04-01 | 2011-10-06 | The Procter & Gamble Company | Produit assouplissant thermostable |
CN102834496A (zh) * | 2010-04-01 | 2012-12-19 | 赢创德固赛有限公司 | 织物柔软剂活性组合物 |
WO2011120822A1 (fr) | 2010-04-01 | 2011-10-06 | Evonik Degussa Gmbh | Composition active d'adoucissant pour étoffe |
US8883712B2 (en) | 2010-04-28 | 2014-11-11 | Evonik Degussa Gmbh | Fabric softening composition |
EP2582780B1 (fr) | 2010-06-17 | 2018-01-24 | Henkel AG & Co. KGaA | Adoucissant textile épaissi |
US8507425B2 (en) | 2010-06-29 | 2013-08-13 | Evonik Degussa Gmbh | Particulate fabric softener comprising ethylenediamine fatty acid amides and method of making |
US8883713B2 (en) | 2012-01-30 | 2014-11-11 | Evonik Industries Ag | Fabric softener active composition |
US9441187B2 (en) | 2012-05-07 | 2016-09-13 | Evonik Degussa Gmbh | Fabric softener active composition and method for making it |
US9801797B2 (en) | 2013-03-22 | 2017-10-31 | Evonik Degussa Gmbh | Formulation comprising ester quats based on isopropanolamine |
US10011806B2 (en) | 2013-11-05 | 2018-07-03 | Evonik Degussa Gmbh | Method for making a tris-(2-hydroxyethyl)-methylammonium methylsulfate fatty acid ester |
US10815191B2 (en) | 2014-09-22 | 2020-10-27 | Evonik Operations Gmbh | Formulation comprising ester quats based on isopropanolamine and tetrahydroxypropyl ethylenediamine |
US10113137B2 (en) | 2014-10-08 | 2018-10-30 | Evonik Degussa Gmbh | Fabric softener active composition |
Also Published As
Publication number | Publication date |
---|---|
EP0293955B1 (fr) | 1993-01-13 |
DE3877422T2 (de) | 1993-05-13 |
DE3877422D1 (de) | 1993-02-25 |
GB8810310D0 (en) | 1988-06-02 |
EP0293955A3 (en) | 1989-07-05 |
ATE84566T1 (de) | 1993-01-15 |
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